CN112204042B - Novel compound and organic light-emitting element using same - Google Patents

Novel compound and organic light-emitting element using same Download PDF

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CN112204042B
CN112204042B CN201980034898.5A CN201980034898A CN112204042B CN 112204042 B CN112204042 B CN 112204042B CN 201980034898 A CN201980034898 A CN 201980034898A CN 112204042 B CN112204042 B CN 112204042B
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CN112204042A (en
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河宰承
金性昭
千民承
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LG Chem Ltd
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    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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    • 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
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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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    • 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

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Abstract

The application provides a novel compound and an organic light-emitting element using the same.

Description

Novel compound and organic light-emitting element using same
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2018-0098139, 8/22/2018, the entire contents of the disclosure of which are incorporated as part of the present specification.
The present application relates to a novel compound and an organic light-emitting element 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 element utilizing 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 element 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 element, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In such a structure of an organic light-emitting element, 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, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons transition again to the ground state.
For the organic matter used for the organic light emitting element as described above, development of new materials is continuously demanded.
Prior art literature
Patent literature
(patent document 1) Korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Problems to be solved
The present invention relates to a novel compound and an organic light-emitting element 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,
L 1 and L 2 Each independently is a single bond, phenylene, biphenylene, or naphthylene,
Ar 1 to Ar 3 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S 2-60 A heteroaryl group, which is a group,
a is any one of the groups represented by the following chemical formulas 2-1 to 2-3,
in the above chemical formulas 2-1 to 2-3,
Z 1 to Z 7 Each independently is hydrogen; deuterium; halogen; cyano group; a nitro group; an amino group; substituted or unsubstituted C 1-60 An alkyl group; substituted or unsubstituted C 1-60 A haloalkyl group; substituted or unsubstituted C 1-60 An alkoxy group; substituted or unsubstituted C 1-60 Haloalkoxy, substituted or unsubstituted C 3-60 Cycloalkyl; substituted or unsubstituted C 2-60 Alkenyl groups; substituted or unsubstituted C 6-60 An aryl group; substituted or unsubstituted C 6-60 An aryloxy group; or substituted or unsubstituted C comprising one or more selected from N, O and S 2-60 A heteroaryl group, which is a group,
n1 and n2 are each independently integers from 0 to 4,
n3 is an integer of 0 to 3,
when n1 to n3 are each 2 or more, structures in parentheses of 2 or more are the same or different from each other,
* L represents the same as the formula 1 2 The position of the connection is determined by the position of the connection,
R 1 to R 4 Each independently is hydrogen, or substituted or unsubstituted C 1-60 An alkyl group.
In addition, the present invention provides an organic light emitting element, including: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
Effects of the invention
The compound represented by the above chemical formula 1 can be used as a material for an organic layer of an organic light-emitting element, and in the organic light-emitting element, improvement of efficiency, lower driving voltage, and/or improvement of life characteristics can be achieved.
Drawings
Fig. 1 illustrates an example of an organic light-emitting element including 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 element constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4.
Detailed Description
In the following, the invention will be described in more detail in order to aid understanding thereof.
In the present description of the invention,represents a bond to other substituents, a single bond being defined by L 1 And L 2 The indicated portion is free of other atoms.
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 amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio (alkylthio); arylthio (aryl thio); alkylsulfonyl (alkyl sulfoxy); arylsulfonyl (aryl sulfonyl); 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 1 or more of N, O and 1 or more of the heteroaryl groups of S atoms is substituted or unsubstituted, or a substituent linked with 2 or more of the above-exemplified substituents is substituted or unsubstituted. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, in the ester group, oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. According to another embodiment, the above alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but the present invention is not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as phenyl, biphenyl, and terphenyl, but is not limited thereto. As the polycyclic aryl group, there may be mentionedIs naphthyl, anthryl, phenanthryl, pyrenyl, perylene,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 heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo- >Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), iso>Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present specification, the aryl 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 the present specification, the heteroaryl group in the heteroarylamine group may be applied to the above description about 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.
In another aspect, the present invention provides an anthracene derivative compound represented by the above chemical formula 1. Such a compound has both silyl groups and benzimidazolyl groups, and thus high efficiency, low driving voltage, long lifetime, and the like of an organic light-emitting element using a compound having only silyl groups or benzimidazolyl groups can be achieved.
In the above chemical formula 1, L 1 And L 2 May each independently be any one selected from a single bond and the following groups:
in addition, ar 1 To Ar 3 Each independently is phenyl, biphenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl,
wherein Ar is 1 To Ar 3 Unsubstituted; or may be substituted with 1 or 2 substituents each independently selected from methyl, phenyl, dibenzofuranyl and dibenzothiophenyl.
Specifically, ar 1 To Ar 3 May each independently be any one selected from the group consisting of:
of the above-mentioned groups, the group,
x is O, S, C (methyl) 2 Or N (phenyl).
In addition, in the above chemical formulas 2-1 to 2-3,
Z 1 to Z 7 Can each independently be hydrogen, C 1-4 Alkyl, C 6-10 Aryl, or C containing 1 or 2N atoms 2-10 Heteroaryl groups.
Specifically, Z 1 To Z 7 May each independently be hydrogen, methyl, ethyl, isopropyl, phenyl, naphthyl, pyridinyl, or quinolinyl.
For example, Z 1 To Z 4 Each independently is hydrogen, methyl, ethyl, isopropyl, phenyl, naphthyl, pyridinyl, or quinolinyl,
Z 5 to Z 7 May each independently be hydrogen, methyl, ethyl, or phenyl.
In addition, R 1 To R 4 Are all hydrogen, or
R 1 And R is 2 Each independently is C 1-4 Alkyl, R 3 And R is 4 Is hydrogen or
R 1 And R is 2 Is hydrogen, R 3 And R is 4 Can each independently be C 1-4 An alkyl group.
At this time, R 1 And R is 2 Can be identical to each other, R 3 And R is 4 May be identical to each other.
For example, R 1 To R 4 Are all hydrogen, or
R 1 And R is 2 Is methyl, ethyl, or tert-butyl, R 3 And R is 4 Is hydrogen or
R 1 And R is 2 Is hydrogen, R 3 And R is 4 May be methyl, ethyl, or tert-butyl.
In addition, the above compound may be represented by any one of the following chemical formulas 1-1 to 1-3:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
In the above chemical formulas 1-1 to 1-3,
for L 1 、L 2 、Ar 1 To Ar 3 、R 1 To R 4 And Z 1 To Z 6 The description of (a) is the same as that of the above chemical formula 1,
for Z 5 ' and Z 6 The description of' refer to Z respectively 5 And Z 6 Is described in (2).
For example, the above compound may be any one selected from the following compounds:
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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]
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In the above reaction formula 1, X is halogen, preferably bromine or chlorine, and the definition of the remaining substituents is the same as the above description. The above reaction is a reaction for producing the compound represented by chemical formula 1 by subjecting the compound F2 and the compound G or H to a suzuki coupling reaction, preferably in the presence of a palladium catalyst and a base, and the reactive group for the suzuki coupling reaction can be modified according to a technique known in the art. Such a manufacturing method can be more concretely described in a manufacturing example described later.
As an example, the compound F2 of the above-mentioned reaction formula 1 can be produced by the method shown in the following reaction formula 2. Specifically, at L 1 When the compound is not a single bond, the compound F2 can be produced by the reaction step shown in (1), and the compound is represented by L 1 In the case of a single bond, compound F2 can be produced by the reaction step shown in (2).
[ reaction type 2]
In the above reaction formula 2, X is each independently halogen, preferably bromine or chlorine, and the definition of the remaining substituents is the same as the above description. Each of the above steps 1-1 and 1' -1 is preferably carried out in the presence of a strong base as a nucleophilic substitution reaction. The above-mentioned steps 1-2 are steps of introducing a boric acid substituent into the above-mentioned compound a by boronation (borylation), and the above-mentioned steps 1-3 and 1' -2 are steps of producing an intermediate compound F1 by combining the compound SM4 into the intermediate compound by suzuki coupling reaction, respectively. In addition, the above steps 1 to 4 are steps for producing the compound F2 by boronation after introducing a bromine group into the compound F1.
As an example, the compound G of the above reaction formula 1 can be produced by the reaction step shown in the following reaction formula 3 (1), and the compound H of the above reaction formula 1 can be produced by the reaction step shown in the following reaction formula 3 (2).
[ reaction type 3]
In the above reaction formula 3, X is each independently halogen, and the definition of the remaining substituents is the same as the above description. Each of the above (1) and (2) is a step of producing compounds G and H by a cyclization removal reaction after producing an amide by a reaction of a nitro compound and a carbonyl halide.
In another aspect, the present invention provides an organic light emitting element including the compound represented by the above chemical formula 1. As one example, the present invention provides an organic light emitting element, including: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
The organic layer of the organic light-emitting element of the present invention may be formed of a single-layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light-emitting element 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, or the like as an organic layer. However, the structure of the organic light emitting element is not limited thereto, and may include a smaller number of organic layers.
The organic layer may include a light-emitting layer including the compound represented by chemical formula 1.
The organic layer may include a light emitting layer, an electron transporting layer, and an electron injecting layer, and the electron transporting layer may include a compound represented by chemical formula 1.
The organic layer of the organic light-emitting element of the present invention may be formed of a single-layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light-emitting element 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 element is not limited thereto, and may include a smaller or larger number of organic layers.
The organic light-emitting element according to the present invention may have a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate. The organic light-emitting element according to the present invention may have a reverse structure (inverted type) in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure of an organic light emitting element 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 element including 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 element constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in 1 or more layers among the above hole injection layer, hole transport layer, light emitting layer, and electron transport layer.
The organic light emitting element according to the present invention may be manufactured using materials and methods known in the art, except that 1 or more of the organic layers contain the compound represented by 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 material or different materials.
For example, the organic light emitting element according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, it can be manufactured as follows: PVD (physical Vapor Deposition) process such as sputtering (sputtering) or electron beam evaporation (physical vapor deposition) is used to vapor-deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting element may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
In addition, the compound represented by the above chemical formula 1 may be used not only in the vacuum deposition method but also in the solution coating method to form an organic layer in the production of an organic light-emitting element. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting element 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); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides;poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that injects holes from an electrode, and the following compounds are preferable as the hole injection substance: a compound which has a hole transporting ability, has an effect of injecting holes from the anode, has an excellent hole injecting effect for the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from migrating to the electron injecting layer or the electron injecting material, and has an excellent thin film forming ability. The HOMO (highest occupied molecular orbital ) of the hole injection species is preferably between the work function of the anode species and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers.
The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and a hole-transporting substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer is preferable, and a substance having a large mobility to the holes is preferable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
The light-emitting substance is a substance capable of receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining them to emit light in the visible light region, and is preferably fluorescent or phosphorA substance having high quantum efficiency of light. As a specific example, there is 8-hydroxyquinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
The light emitting layer may include a host material and a dopant material as described above. The host material may further contain an aromatic condensed ring derivative, a heterocyclic compound, or the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, 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,And bisindenopyrene, etc., wherein the styrylamine compound is a compound in which at least 1 arylvinyl group is substituted in 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.
The electron transport layer is a layer which receives electrons from the electron injection layer and transports the electrons to the light emitting layer, and the electron transport material is a material capable of transporting electronsA substance that can well receive electrons from the cathode and transfer them to the light-emitting layer is suitable for a substance having high mobility of electrons. As the electron-transporting substance, a compound represented by the above chemical formula 1 can be used. Alternatively, the compound represented by the above chemical formula 1 may be used together with an electron transporting substance which is generally used. Specific examples of the electron-transporting material that is usually used include metal complex compounds, al complexes of 8-hydroxyquinoline, and Alq-containing materials 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The electron transport layer may be used with any desired cathode material as used in the art. In particular, examples of suitable cathode materials are the usual materials having a low work function accompanied by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a silver layer.
The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound as follows: a compound which has an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole injection layer, and has excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The organic light emitting element 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.
The compound represented by the above chemical formula 1 may be contained in an organic solar cell or an organic transistor in addition to the organic light-emitting element.
The production of the compound represented by the above chemical formula 1 and the organic light-emitting element including the same is specifically described in the following examples. However, the following examples are given by way of illustration of the present specification, and the scope of the present invention is not limited thereto.
Synthesis example 1: production of intermediate Compounds F2-1 to F2-14
Step 1-1: production of intermediate Compounds A1 to A8
To produce intermediate compounds A1 to A8, respectively, the starting material 1 (1 equivalent) of table 1 below was dissolved in THF (excess), the temperature was reduced to-78 degrees, and then 2.5M n-BuLi (0.95 equivalent) was added dropwise, thereby obtaining a reactant 1. In another flask, after the starting material 2 (1 equivalent) of the following table 1 was dissolved in THF (excessive amount), the temperature was lowered to-78 ℃, and then 2.5M n-BuLi (1 equivalent) was added dropwise and stirred for 3 hours, the starting material 3 (1 equivalent) of the following table 1 was added, thereby producing a reactant 2. To the resultant reaction product 2, the above-mentioned first-produced reaction product 1 was added dropwise, and the mixture was slowly heated to room temperature and stirred for 10 hours. After completion of the reaction, water was added to separate the layers and remove the solvent, and the residue was subjected to silica gel column chromatography (ethyl acetate/hexane 1:15), whereby the following products A1 to A8 of table 1 were obtained, and the respective yields and MS data are shown below.
[ Table 1 ]
Step 1-2: production of intermediate Compounds B1 to B8
To produce intermediate compounds B1 to B8, respectively, one (1 equivalent) of the intermediate compounds A1 to A8 produced in the above step 1-1 was dissolved in THF (excess), the temperature was lowered to-78 degrees, 2.5M n-BuLi (1.5 equivalent) was then added dropwise, triisopropyl borate (1.3 equivalent) was added after 30 minutes, and stirring was carried out for 1 hour after rising to RT. 1N HCl (excess) was added, and after stirring for 30 minutes, the solvent was removed by layer separation, and then after purification with ethyl acetate, the resulting solid was added to acetic acid (excess), and then 1ml sulfuric acid was added dropwise, and stirring and refluxing were performed. The temperature was lowered to room temperature, neutralized with water, and the filtered solid was recrystallized from ethyl acetate and hexane to obtain the following products B1 to B8 in table 2, the respective yields and MS data are shown below.
[ Table 2 ]
Step 1-3: production of intermediate Compounds F1-1 to F1-11
To prepare intermediate compounds F1-1 to F1-11, respectively, starting material 1 (1 equivalent) in Table 3 below and starting material 2 in Table 3 below were added to THF (excess), 2M aqueous potassium carbonate solution (30 vol% relative to THF) was added, tetrakis (triphenylphosphine) palladium (2 mol%) was added, and the mixture was heated and stirred for 10 hours. The temperature was lowered to room temperature, and after the reaction was completed, the aqueous potassium carbonate solution was removed and the layers were separated. After the solvent was removed, vacuum distillation was performed, and recrystallization was performed with THF and ethyl acetate, whereby the following F1-1 to F1-11 of table 3 were obtained, and the respective yields and MS data are shown below.
[ Table 3 ]
Step 1' -1: production of intermediate compound C1
To produce intermediate compound C1, starting material 1 (1 equivalent) of table 4 below was dissolved in THF (excess), the temperature was reduced to-78 ℃, 2.5M n-BuLi (0.95 equivalent) was then added dropwise, starting material 2 (1 equivalent) of table 4 below was added dropwise, and the mixture was slowly warmed to room temperature and stirred for 10 hours. After completion of the reaction, water was added to separate the layers and remove the solvent, and the residue was subjected to silica gel column chromatography (ethyl acetate/hexane 1:15), whereby the product C1 shown in table 4 was obtained, and the yield and MS data thereof were as follows.
[ Table 4 ]
Step 1' -2: production of intermediate Compounds F1-12 to F1-14
To prepare intermediate compounds F1-12 to F1-14, starting material 2 of Table 5 below was dissolved in THF (in excess), the temperature was lowered to-78℃and then 2.5M n-BuLi (1.5 eq) was added dropwise, starting material 1 of Table 5 below (1.05 eq) was added after 30 minutes, and stirring was continued for 1 hour after rising to RT. 1N HCl (excess) was added, and after stirring for 30 minutes, the solvent was removed by layer separation, followed by recrystallization from THF and ethyl acetate, whereby the following products F-12 to F1-14 of Table 5 were obtained, and the respective yields and MS data are shown below.
[ Table 5 ]
Step 1-4: production of intermediate Compounds F2-1 to F2-14
To produce intermediate compounds F2-1 to F2-14, respectively, one (1 equivalent) of F1-1 to F1-14 produced in the above steps 1-3 and 1' -2 was dissolved in chloroform, and N-bromosuccinimide (NBS, 1.01 equivalent) was dissolved in chloroform and added dropwise. After completion of the reaction, 1N HCl (excess) was added, and after extraction, the solid obtained by distillation under reduced pressure was dried in a vacuum oven for 24 hours, thereby obtaining a white solid. After dissolving the above solid in THF (excess), the temperature was reduced to-78 ℃, then 2.5M n-BuLi (1.5 eq) was added dropwise, after 30 minutes triisopropyl borate (1.3 eq) was added, and after rising to RT, stirring was carried out for 1 hour. After adding 1N HCl (excess), stirring for 30 minutes, separating the layers to remove the solvent, purifying with ethyl acetate, adding the obtained solid to acetic acid (excess), adding 1ml sulfuric acid dropwise, stirring and refluxing. The temperature was lowered to room temperature, neutralized with water, and the filtered solid was recrystallized from chloroform and ethyl acetate to obtain the following products F2-1 to F2-14 in table 6, the respective yields and MS data are shown below.
[ Table 6 ]
/>
Synthesis example 2: production of intermediate compounds G1 to G8 and H1 to H7
Step 2-1: production of intermediate Compounds D1-1 to D1-5
To produce intermediate compounds D1-1 to D1-5, respectively, starting material 1 (1 equivalent), starting material 2 (1.5 equivalent) and 8.8g (2.5 equivalents) of sodium acetate of table 7 below were heated and stirred at 160 ℃ for 9 hours under nitrogen atmosphere. The reaction solution was cooled to room temperature, diluted with ethyl acetate and filtered. After concentrating the filtrate, purification was performed by silica gel column chromatography (hexane), thereby obtaining the following products D1-1 to D1-5 of table 7, the respective yields and MS data are shown below.
[ Table 7 ]
Step 2-2 and 2-3: production of intermediate Compounds G1 to G8
To produce intermediate compounds G1 to G8, respectively, 9.9G (33.8 mmol) of the starting material 1 (1 equivalent) of table 8 below was dissolved in 75ml of THF, and a solution of sodium bisulphite (5.5 equivalents)/water (25% v/v%) was added dropwise while stirring at room temperature under a nitrogen atmosphere. Excess methanol was further added and stirred for 3 hours. Then, ethyl acetate (5 eq) was added and sodium bicarbonate (excess) was added. Further, the starting material 2 (1 equivalent) in table 8 below was prepared as a solution of ethyl acetate (25% v/v%) and was added dropwise, followed by stirring at room temperature for 5 hours. The above solution was extracted with ethyl acetate, washed successively with water, 10% aqueous potassium carbonate and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed by evaporation under reduced pressure to obtain a solid (intermediate D2 of table 8 below), which was added with p-toluenesulfonic acid monohydrate (0.3 equivalent) in xylene solvent, heated under reflux for 5 hours and azeotropically dehydrated. After completion of the reaction, the reaction mixture was cooled, the solvent was distilled off under reduced pressure, and the solid was washed with ethanol to obtain the following products G1 to G8 in table 8, and the yields and MS data are shown below.
[ Table 8 ]
Step 3-1: production of intermediate Compounds E1-1 to E1-6
The same procedure as in step 2-1 was used except that starting materials 1 and 2 of Table 9 below were used instead of starting materials 1 and 2 of Table 7 above in order to produce intermediate compounds E1-1 to E1-6, respectively, to obtain products E1-1 to E1-6 of Table 9 below, the respective yields and MS data being shown below.
[ Table 9 ]
Steps 3-2 and 3-3: production of intermediate compounds H1 to H6
To produce intermediate compounds H1 to H5, respectively, the same procedure as in steps 2-2 and 2-3 was used except that starting materials 1 and 2 of table 10 below were used instead of starting materials 1 and 2 of table 8 above, thereby obtaining H1 to H6 of table 10 below, and the respective yields and MS data are shown below.
[ Table 10 ]
Production of intermediate compound H7
10.0g (41 mmol) of 4-iodobenzoic acid are suspended in 100ml of 1, 2-dichloroethane, and 3 drops of N, N-dimethylformamide are added. 7.3g (61 mmol) of thionyl chloride was further added and heated under reflux for 2 hours. Subsequently, the solvent was removed by evaporation, the residue was dissolved in 100ml of N-methylpyrrolidone, 5.0g (41 mmol) of N-ethyl-1, 2-phenylenediamine was added under ice cooling, and stirred at room temperature for 5 hours. After completion of the reaction, water was added, and the precipitated solid was filtered, and then ethyl acetate and water were added to the obtained solid to extract an organic layer (insoluble matter was separated by filtration). The organic layer was washed with 5% aqueous potassium carbonate, water and brine, and dried over sodium sulfate. The solvent was removed by evaporation to give 11g of a mixture of crude 4-iodo-N- (2-ethylamino-phenyl) benzamide and crude N- (2-aminophenyl) -4-iodo-N-ethylbenzamide.
11g (31 mmol) of the obtained mixture and 1.75g (9 mmol) of p-toluenesulfonic acid monohydrate were dispersed in 100ml of xylene and heated under reflux for 7 hours. After the completion of the reaction, the mixture was cooled, 5% aqueous potassium carbonate and toluene were added thereto, and the organic layer was extracted. The organic layer was washed with 5% aqueous potassium carbonate, water and brine, and dried over sodium sulfate. The solvent was removed by evaporation, and the obtained brown oil was purified by silica gel column chromatography (developer: n-hexane/ethyl acetate=3/1), whereby H7 (2.7 g, yield: 20%) was obtained.
MS[M+H] + ＝349.19
Production example 1: production of Compound 1
After F2-1 (1 equivalent) produced in Synthesis example 1 and G1 (1.02 equivalent) produced in Synthesis example 2 were added to THF (excess), a 2M aqueous potassium carbonate solution (30 vol% based on THF) was added, tetrakis (triphenylphosphine) palladium (2 mol%) was added, and the mixture was heated and stirred for 10 hours. The temperature was lowered to room temperature, and after the reaction was completed, the aqueous potassium carbonate solution was removed to conduct layer separation. After removal of the solvent, vacuum distillation was performed and recrystallization was performed with THF and ethyl acetate, thereby producing the title compound.
Production example 2: production of Compound 2
The title compound was produced in the same manner as in production example 1 except that compound G4 was used instead of compound G1.
Production example 3: production of Compound 3
The title compound was produced in the same manner as in production example 1, except that compound F2-2 was used instead of compound F2-1 and compound G2 was used instead of compound G1.
Production example 4: production of Compound 4
The title compound was produced in the same manner as in production example 1, except that compound F2-3 was used instead of compound F2-1 and compound G5 was used instead of compound G1.
Production example 5: production of Compound 5
The title compound was produced in the same manner as in production example 1 except that compound F2-12 was used instead of compound F2-1 and compound G7 was used instead of compound G1.
Production example 6: production of Compound 6
The title compound was produced in the same manner as in production example 1 except that compound F2-13 was used instead of compound F2-1 and compound G6 was used instead of compound G1.
Production example 7: production of Compound 7
The title compound was produced in the same manner as in production example 1 except that compound F2-4 was used instead of compound F2-1 and compound G2 was used instead of compound G1.
Production example 8: production of Compound 8
The title compound was produced in the same manner as in production example 1, except that compound F2-5 was used instead of compound F2-1 and compound G3 was used instead of compound G1.
Production example 9: production of Compound 9
The title compound was produced in the same manner as in production example 1, except that compound F2-6 was used instead of compound F2-1 and compound G5 was used instead of compound G1.
Production example 10: production of Compound 10
The title compound was produced in the same manner as in production example 1 except that compound F2-7 was used instead of compound F2-1 and compound G4 was used instead of compound G1.
Production example 11: production of Compound 11
The title compound was produced in the same manner as in production example 1 except that compound F2-8 was used instead of compound F2-1 and compound G2 was used instead of compound G1.
Production example 12: production of Compound 12
The title compound was produced in the same manner as in production example 1 except that compound F2-9 was used instead of compound F2-1 and compound G8 was used instead of compound G1.
Production example 13: production of Compound 13
The title compound was produced in the same manner as in production example 1, except that compound F2-4 was used instead of compound F2-1 and compound H2 was used instead of compound G1.
Production example 14: production of Compound 14
The title compound was produced in the same manner as in production example 1 except that compound H4 was used instead of compound G1.
Production example 15: production of Compound 15
The title compound was produced in the same manner as in production example 1, except that compound F2-14 was used instead of compound F2-1 and compound H3 was used instead of compound G1.
Production example 16: production of Compound 16
The title compound was produced in the same manner as in production example 1, except that compound F2-14 was used instead of compound F2-1 and compound H5 was used instead of compound G1.
Production example 17: production of Compound 17
The title compound was produced in the same manner as in production example 1, except that compound F2-10 was used instead of compound F2-1 and compound H6 was used instead of compound G1.
Production example 18: production of Compound 18
The title compound was produced in the same manner as in production example 1, except that compound F2-11 was used instead of compound F2-1 and compound H7 was used instead of compound G1.
The yields and MS data of the compounds 1 to 18 produced in the above production examples 1 to 18 are shown in table 11 below.
[ Table 11 ]
Example 1
As anode, 70/1000 +.The substrate on which ITO/Ag/ITO was deposited was cut into a size of 50 mm. Times.50 mm. Times.0.5 mm, and the substrate was put into distilled water in which a detergent was dissolved, and washed with ultrasonic waves. The detergent was a product of fei-hill co., and the distilled water was filtered 2 times by a Filter (Filter) manufactured by millbore co., ltd. 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 was completed, ultrasonic washing was performed with solvents of isopropyl alcohol, acetone, and methanol in this order, and drying was performed.
On the anode thus prepared, the following compound HI-1 was usedForming a hole injection layer by thermal vacuum deposition, wherein HT1 as a hole transporting substance is formed on the hole injection layer to a thickness +.>Vacuum evaporation is performed to form a hole transport layer. Next, the following compound HT 2->A hole-regulating layer is formed, and then the host BH1 and the dopant BD1 (2 wt.%) are added +.>And vacuum vapor deposition is performed to the thickness of the substrate to form a light-emitting layer. Then, the compound 1 and Liq produced in production example 1 were mixed at 5:5 to form a thickness +.>Electron transport of (a)A layer. In turn, willMagnesium and lithium fluoride (LiF) of a thickness as electron injection layers are formed into films and then as cathodes to give +.>A magnesium and silver (1:4) layer was formed, then +.>CP1 was evaporated, thereby completing the element. In the above process, the vapor deposition rate of the organic matter is maintained +.>/sec.
Examples 2 to 27 and comparative examples 1 to 7
An organic light-emitting device was manufactured in the same manner as in example 1 above, except that the compounds described in table 12 below were used as the electron-transporting layer material and the host material, and the electron-regulating layer was further provided between the electron-transporting layer and the light-emitting layer in examples 25 to 27.
The compounds used in examples 1 to 27 and comparative examples 1 to 7 described above are shown below.
Experimental example 1
When electric current was applied to the organic light emitting elements manufactured in examples 1 to 27 and comparative examples 1 to 7, voltage, efficiency, color coordinates, and lifetime were measured, and the results thereof are shown in table 12 below. T95 refers to the time required for the luminance to decrease from the initial luminance to 95%.
[ Table 12 ]
Example 28
As an anode, will beThe substrate on which the ITO was deposited was cut into a size of 50 mm. Times.50 mm. Times.0.5 mm, and the substrate was put into distilled water in which a detergent was dissolved, and washed with ultrasonic waves. The detergent was a product of fei-hill co., and the distilled water was filtered 2 times by a Filter (Filter) manufactured by millbore co., ltd. 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 was completed, ultrasonic washing was performed with solvents of isopropyl alcohol, acetone, and methanol in this order, and drying was performed.
On the anode thus prepared, HI-1 was reacted withForming a hole injection layer by thermal vacuum deposition, wherein HT3 as a hole transporting substance is formed on the hole injection layer to a thickness +.>Vacuum evaporation is performed to form a hole transport layer. Next, HT 4- >A hole-regulating layer is formed, and then the host BH1 and the dopant BD1 (2 wt.%) are added +.>And vacuum vapor deposition is performed to the thickness of the substrate to form a light-emitting layer. Then, using the compound 1 produced in production example 1, a thickness +.>Is provided. In turn, at ET6 +.>Co-evaporating lithium (2 wt%) to obtain a film electron injection layer, and using aluminum as cathode>Vapor deposition was performed to complete the element. In the course of the above-described process,the vapor deposition rate of the organic matters is maintained>/sec.
Examples 29 to 54 and comparative examples 8 to 13
An organic light-emitting device was manufactured in the same manner as in example 28 above, except that the compounds described in table 13 below were used as the electron-transporting material and the host material, and that an electron-regulating layer was further provided between the electron-transporting layer and the light-emitting layer in examples 52 to 54.
Experimental example 2
When electric current was applied to the organic light emitting elements manufactured in examples 28 to 54 and comparative examples 8 to 13, voltage, efficiency, color coordinates, and lifetime were measured, and the results thereof are shown in table 13 below. T95 refers to the time required for the luminance to decrease from the initial luminance to 95%.
[ Table 13 ]
As shown in tables 12 and 13 above, it was confirmed that the organic light-emitting element using the compound of the present invention as an electron transporting layer material exhibited excellent characteristics in terms of driving voltage, efficiency and stability by smoothly injecting electrons into the light-emitting layer, adjusting smooth transport of carriers, and balancing holes and electrons of the organic light-emitting element according to the chemical structure, as compared with the organic light-emitting element using the compound of the comparative example as an electron transporting layer material.
Symbol description
1: substrate 2: anode
3: light emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: light emitting layer 8: an electron transport layer.

Claims (8)

1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
R 1 to R 4 Each independently is hydrogen, or C 1-10 An alkyl group, a hydroxyl group,
L 1 and L 2 Each independently is a single bond, phenylene, biphenylene, or naphthylene,
Ar 1 to Ar 3 Each independently is phenyl, biphenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl, and
wherein Ar is 1 To Ar 3 Unsubstituted; or by 1 or 2 substituents each independently selected from methyl, phenyl, dibenzofuranyl and dibenzothiophenyl,
a is any one of the groups represented by the following chemical formulas 2-1 to 2-3,
in the chemical formulas 2-1 to 2-3,
Z 1 to Z 7 Each independently is hydrogen, C 1-4 Alkyl, C 6-10 Aryl, or C containing 1 or 2N atoms 2-10 A heteroaryl group, which is a group,
n1 and n2 are each independently integers from 0 to 4,
n3 is an integer of 0 to 3,
when n1 to n3 are each 2 or more, structures in parentheses of 2 or more are the same or different from each other,
* L represents the same as the formula 1 2 The location of the connection.
2. The compound of claim 1, wherein L 1 And L 2 Each independently is selected from a single bond and any one of the following groups:
3. the compound of claim 1, wherein Ar 1 To Ar 3 Each independently is any one selected from the following groups:
of the above-mentioned groups, the group,
x is O, S, C (methyl) 2 Or N (phenyl).
4. The compound according to claim 1, wherein, in the chemical formulas 2-1 to 2-3,
Z 1 to Z 4 Each independently is hydrogen, methyl, ethyl, isopropyl, phenyl, naphthyl, pyridinyl, or quinolinyl,
Z 5 to Z 7 Each independently is hydrogen, methyl, ethyl, or phenyl.
5. The compound of claim 1, wherein R 1 To R 4 Are all hydrogen, or
R 1 And R is 2 Each independently is C 1-4 Alkyl, R 3 And R is 4 Is hydrogen or
R 1 And R is 2 Is hydrogen, R 3 And R is 4 Each independently is C 1-4 An alkyl group.
6. A compound according to claim 1, wherein the compound is represented by any one of the following chemical formulas 1-1 to 1-3:
chemical formula 1-1
Chemical formula 1-2
Chemical formulas 1-3
In the chemical formulas 1-1 to 1-3,
L 1 、L 2 、Ar 1 to Ar 3 、R 1 To R 4 And Z 1 To Z 6 As defined in claim 1,
Z 5 ' and Z 6 ' is defined separately from Z in claim 1 5 And Z 6 Is the same as defined in the following.
7. The compound of claim 1, wherein the compound is any one selected from the group consisting of:
8. an organic light emitting element, comprising: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 7.
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