CN117616024A - Compound and organic light emitting device comprising the same - Google Patents

Compound and organic light emitting device comprising the same Download PDF

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CN117616024A
CN117616024A CN202380012748.0A CN202380012748A CN117616024A CN 117616024 A CN117616024 A CN 117616024A CN 202380012748 A CN202380012748 A CN 202380012748A CN 117616024 A CN117616024 A CN 117616024A
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group
chemical formula
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许东旭
尹正民
尹俊
尹喜敬
李在卓
韩修进
洪性佶
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LG Chem Ltd
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    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/08—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
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    • C07—ORGANIC CHEMISTRY
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    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
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    • C07D253/06—1,2,4-Triazines
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    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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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]
    • H10K50/14—Carrier transporting layers
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    • H10K50/14—Carrier transporting layers
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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Abstract

The present specification relates to a compound represented by chemical formula 1 and an organic light emitting device including the same.

Description

Compound and organic light emitting device comprising the same
Technical Field
The present application claims priority from korean patent application No. 10-2022-0030012, filed to the korean patent office on 3 months 10 of 2022, the entire contents of the disclosure of which are incorporated herein by reference. The present specification relates to a compound and an organic light emitting device including the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, 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. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons transition to the ground state again.
There is a continuing need to develop new materials for use in organic light emitting devices as described above.
Disclosure of Invention
Technical problem
The present specification provides compounds and organic light emitting devices comprising the same.
Solution to the problem
An embodiment of the present specification provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
l1 and L2 are the same or different from each other and are each independently a substituted or unsubstituted arylene group,
ar1 and Ar2 are the same as or different from each other and are each independently represented by the following chemical formula A,
the part of the benzene ring without the indicated substituent is replaced by hydrogen or deuterium,
[ chemical formula A ]
In the above-mentioned chemical formula a,
x1 is N or CR1, X2 is N or CR2, X3 is N or CR3, X4 is N or CR4, X5 is N or CR5,
at least 2 of X1 to X5 are N,
r1 to R5 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with each other with the adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring,
the position of the bond with the above chemical formula 1 is shown.
In addition, an embodiment of the present specification provides an organic light emitting device, including: an anode, a cathode, and 1 or more organic layers provided between the anode and the cathode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
Effects of the invention
The compounds described in the present specification can be used as materials for organic layers of organic light-emitting devices. The compound according to at least one embodiment of the present specification may achieve an improvement in efficiency, a lower driving voltage, and/or an improvement in lifetime characteristics in an organic light emitting device. In particular, the compounds described in this specification can be used as a material for hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection. In addition, it has effects of low driving voltage, high efficiency and/or long life compared to the existing organic light emitting device.
Drawings
Fig. 1 illustrates an example of an organic light emitting device in which a substrate 1, an anode 2, an organic layer 10, and a cathode 9 are stacked in this order.
Fig. 2 illustrates an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 9 are stacked in this order.
Fig. 3 illustrates an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4-1, a second hole transport layer 4-2, a light-emitting layer 5, an electron transport and injection layer 8, and a cathode 9 are stacked in this order.
Fig. 4 illustrates an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport and injection layer 8, and a cathode 9 are stacked in this order.
[ description of the symbols ]
1: substrate board
2: anode
3: hole injection layer
4: hole transport layer
4-1: a first hole transport layer
4-2: a second hole transport layer
5: light-emitting layer
6: electron transport layer
7: electron injection layer
8: electron transport and injection layers
9: cathode electrode
10: organic layer
Detailed Description
The present specification will be described in more detail below.
In the present specification, when a certain component is referred to as "including/comprising" a certain component, unless otherwise specified, it means that other components may be further included, rather than excluded.
In this specification, when it is stated that a certain member is located "on" another member, it includes not only the case where the certain member is connected to the other member but also the case where another member exists between the two members.
In the present description of the invention,or the dotted line indicates the location of the binding to the chemical formula or compound.
In the present specification, examples of substituents are described below, but are not limited thereto.
The term "substituted" as used herein means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.
In the present specification, the term "substituted or unsubstituted" means substituted with a member selected from deuterium, halogen group, cyano (-CN), nitro, hydroxy, alkyl, cycloalkyl, alkoxy, phosphino, aryloxy, alkylthioArylthio groupsAlkylsulfonyl->Arylsulfonyl->1 or 2 or more substituents selected from the group consisting of alkenyl, silyl, boron, amino, aryl and heterocyclic groups are substituted, or a substituent obtained by linking 2 or more substituents selected from the above-exemplified substituents is substituted, or no substituent is present. 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 term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, halogen group, cyano group, nitro group, hydroxyl group, amino group, silyl group, boron group, alkoxy group, aryloxy group, alkyl group, cycloalkyl group, aryl group, and heterocyclic group, or substituted with a substituent in which 2 or more substituents among the above exemplified substituents are linked, or does not have any substituent.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, cyano, alkyl, cycloalkyl, aryl, and heterocyclic groups, or substituted with a substituent in which 2 or more substituents out of the above-exemplified substituents are linked, or does not have any substituent.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, alkyl, cycloalkyl, and aryl, or substituted with a substituent in which 2 or more substituents out of the above-exemplified substituents are linked, or does not have any substituent.
Examples of the above substituents are described below, but are not limited thereto.
In the present specification, as examples of the halogen group, there are fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
In the present specification, the silyl group may be represented by-SiY a Y b Y c The chemical formula of (A) is shown in the specification, Y is shown in the specification a 、Y b And Y c Each may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The silyl group is specifically, but 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 may be represented BY-BY d Y e The chemical formula of (A) is shown in the specification, Y is shown in the specification d And Y e Each may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Examples of the boron group include trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but are not limited thereto.
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 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the above alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 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, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, and the like.
In this specification, the above description of the alkyl group may be applied to the arylalkyl group other than the aryl group.
In the present specification, the above-mentioned alkoxy group may be a straight chain, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decyloxy and the like are possible, but not limited thereto.
The alkyl groups, alkoxy groups, and other substituents containing an alkyl moiety described in this specification are all included in straight or branched chain forms.
In the present specification, the alkenyl group may be a straight chain or 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-phenylethylen-1-yl, 2-diphenylethylene-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene-1-yl, 2-bis (diphenyl-1-yl) ethylene-1-yl, styryl and the like, but are not limited thereto.
In the present specification, the alkynyl group is a substituent group including a triple bond between carbon atoms, and may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkynyl group has 2 to 20 carbon atoms. According to another embodiment, the above alkynyl group has 2 to 10 carbon atoms.
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, cyclohexyl, cycloheptyl, cyclooctyl and the like, but not limited thereto.
In the present specification, the amine group is-NH 2 The amine group may be substituted with the alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, or a combination thereof. The number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the amine group has 1 to 20 carbon atoms. According to one embodiment, the amine group has 1 to 10 carbon atoms. Specific examples of the substituted amine group include, but are not limited to, methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, 9-dimethylfluorenylphenylamino, pyridylphenylamino, diphenylamino, phenylpyridylamino, naphthylamino, biphenylamino, anthracenylamino, dibenzofuranylphenylamino, 9-methylanthracenylamino, diphenylamino, phenylnaphthylamino, xylylamino, phenyltolylamino, and diphenylamino.
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.
In the present specification, the aryl group may be an aryl group formed of a single ring, or a polycyclic aryl group (an aryl group having two or more rings). The aryl group having a single ring may be a phenyl group or a group formed by connecting 2 or more phenyl groups. The aryl group having a single ring may be a phenyl group, a biphenyl group, a terphenyl group, a tetrabiphenyl group, or the like, but is not limited thereto. Polycyclic aryl groups may be groups obtained by fusing 2 or more single rings such as naphthyl and phenanthryl. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, and the like,A group, a fluorenyl group, a triphenylene group, and the like, 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 this case, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.
In the case where the above fluorenyl group is substituted, it may be An isospirofluorenyl group;(9, 9-dimethylfluorenyl) and +.>(9, 9-diphenylfluorenyl) and the like. However, the present invention is not limited thereto.
In the present specification, the aryl group in the aryloxy group may be applied to the above description about the aryl group.
In the present specification, the above-mentioned alkyl groups in the alkylthio group and the alkylsulfonyl group may be applied to the above-mentioned explanation about the alkyl group.
In the present specification, the above-described aryl groups in the arylthio group and the arylsulfonyl group can be applied to the above-described description about the aryl group.
In the present specification, the heterocyclic group is a ring group containing 1 or more heteroatoms in N, O, P, S, si and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to one embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of the heterocyclic group include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, quinolinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuranyl, benzonaphthothienyl, indenocarzolyl, triazinyl, and the like.
In this specification, the heteroaryl group is not aromatic, and the above description about the heterocyclic group can be applied.
In the present specification, the arylene group is not limited to 2, and the description of the aryl group may be applied.
In this specification, the heterocyclic ring having 2 valences may be applied to the above description of the heterocyclic group, except that the heterocyclic ring has 2 valences.
In this specification, unless the heteroarylene group is 2-valent, the above description of heteroaryl groups may be applied.
In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, the "ring" means a hydrocarbon ring or a heterocyclic ring.
The hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a condensed ring of an aromatic group and an aliphatic ring, and may be selected from the examples of cycloalkyl groups and aryl groups.
In the present specification, the meaning of forming a ring by bonding adjacent groups to each other means that a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic heterocyclic ring, or condensed rings thereof are formed by bonding adjacent groups to each other. The hydrocarbon ring refers to a ring composed of only carbon and hydrogen atoms. The heterocyclic ring is a ring containing 1 or more elements selected from N, O, P, S, si and Se. In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring, and the aromatic heterocyclic ring may be monocyclic or polycyclic.
In the present specification, the aliphatic hydrocarbon ring means a ring which is not aromatic and is composed of only carbon atoms and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1, 4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like.
In the present specification, an aromatic hydrocarbon ring means an aromatic ring composed of only carbon atoms and hydrogen atoms. Examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, and,Pentacene, fluorene, indene, acenaphthylene, benzofluorene, spirofluorene, and the like, but is not limited thereto. In the present specification, an aromatic hydrocarbon ring can be interpreted as having the same meaning as an aryl group.
In the present specification, an aliphatic heterocyclic ring means an aliphatic ring containing 1 or more hetero atoms. Examples of aliphatic heterocycles include ethylene oxide (oxalane), tetrahydrofuran, and 1, 4-di-Alkyl (1, 4-dioxane), pyrrolidine, piperidine, morpholine, oxepane> Azacyclooctane->Thiocyclooctane->And the like, but is not limited thereto.
In the present specification, an aromatic heterocycle means an aromatic ring containing 1 or more hetero atoms. Examples of the aromatic heterocyclic ring include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, and the like, Azole, i->Oxazole, thiazole, isothiazole, triazole, < >>Diazoles, thiadiazoles, dithiazoles, tetrazoles, pyrans, thiopyrans, pyridazines,/->Oxazine, thiazide, di->Alkene, triazine, tetrazine, isoquinoline, quinoline, quinol, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, naphthyridine, triazaindene, indole, indolizine, benzothiazole, benzo->Oxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, pheno->Oxazine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.
Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiment of the present invention may be modified into various forms, and the scope of the present invention is not limited to the embodiment described below.
The compound represented by chemical formula 1 according to the present invention is characterized in that 2N-containing ring groups represented by chemical formula a are linked to a biphenyl group including a cyano group through a linking group, and since 2N-containing ring groups in a molecule increase electron mobility, efficiency of an organic light emitting device increases, and 1 cyano group is included in a molecule to adjust electron injection characteristics, thereby exhibiting an effect of increasing lifetime of the organic light emitting device.
Accordingly, when the compound represented by the above chemical formula 1 is applied to an organic light emitting device, an organic light emitting device having high efficiency, low voltage, and/or long life characteristics can be obtained.
Chemical formula 1 will be described in detail below.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
l1 and L2 are the same or different from each other and are each independently a substituted or unsubstituted arylene group,
ar1 and Ar2 are the same as or different from each other and are each independently represented by the following chemical formula A,
the part of the benzene ring without the indicated substituent is replaced by hydrogen or deuterium,
[ chemical formula A ]
In the above-mentioned chemical formula a,
x1 is N or CR1, X2 is N or CR2, X3 is N or CR3, X4 is N or CR4, X5 is N or CR5,
at least 2 of X1 to X5 are N,
r1 to R5 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with each other with the adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring,
the position of the bond with the above chemical formula 1 is shown.
In one embodiment of the present specification, L1 and L2 are the same or different from each other, each independently being a substituted or unsubstituted arylene group.
In one embodiment of the present specification, L1 and L2 are the same or different from each other, and are each independently a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
In one embodiment of the present specification, L1 and L2 are the same or different from each other, and are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
In one embodiment of the present specification, L1 and L2 are the same or different from each other, and are each independently a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
In one embodiment of the present specification, L1 and L2 are the same or different from each other, and are each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted naphthylene group.
In one embodiment of the present specification, L1 and L2 are the same or different from each other, and are each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.
In one embodiment of the present specification, L1 and L2 are the same or different from each other, and are each independently a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.
In one embodiment of the present specification, L1 and L2 are the same or different from each other, and are each independently a phenylene group substituted or unsubstituted with deuterium, or a naphthylene group substituted or unsubstituted with deuterium.
In one embodiment of the present specification, L1 and L2 are the same or different from each other, and are each independently phenylene, biphenylene or naphthylene.
In one embodiment of the present specification, L1 and L2 are the same or different from each other and are phenylene or naphthylene.
In one embodiment of the present description, L1 and L2 are the same and are substituted or unsubstituted phenylene.
In one embodiment of the present description, L1 and L2 are the same and are substituted or unsubstituted naphthylene.
In one embodiment of the present specification, L1 and L2 are the same or different from each other, and each is independently represented by any one of the following structural formulas.
In the above structural formula, the broken line indicates the bonding position.
In one embodiment of the present specification, L1 and L2 are the same or different from each other, and each is independently represented by any one of the following structural formulas.
In the above structural formula, the broken line indicates the bonding position.
In one embodiment of the present specification, L1 and L2 are the same or different from each other, and each is independently represented by any one of the following structural formulas.
In the above structural formula, the broken line indicates the bonding position.
In one embodiment of the present specification, ar1 and Ar2 are the same as or different from each other, each independently represented by the following chemical formula A,
[ chemical formula A ]
In the above-mentioned chemical formula a,
x1 is N or CR1, X2 is N or CR2, X3 is N or CR3, X4 is N or CR4, X5 is N or CR5,
at least 2 of X1 to X5 are N,
r1 to R5 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with each other with the adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring,
the position of the bond with the above chemical formula 1 is shown.
In one embodiment of the present disclosure, X1 and X2 are N, X3 is CR3, X4 is CR4, and X5 is CR5.
In one embodiment of the present disclosure, X1 and X3 are N, X2 is CR2, X4 is CR4, and X5 is CR5.
In one embodiment of the present disclosure, X1 and X5 are N, X2 is CR2, X3 is CR3, and X4 is CR4.
In one embodiment of the present disclosure, X1, X3 and X5 are N, X2 is CR2, and X4 is CR4.
In one embodiment of the present disclosure, X1, X4 and X5 are N, X2 is CR2, and X3 is CR3.
In one embodiment of the present disclosure, X1, X2, X4 and X5 are N and X3 is CR3.
In one embodiment of the present specification, 2 to 4 of X1 to X5 are N.
In one embodiment of the present specification, 2 of X1 to X5 are N.
In one embodiment of the present specification, 3 of X1 to X5 are N.
In one embodiment of the present specification, 4 of X1 to X5 are N.
In one embodiment of the present specification, R1 to R5 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl, or are combined with each other with adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring.
In one embodiment of the present specification, R1 to R5 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms.
In one embodiment of the present specification, R1 to R5 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.
In one embodiment of the present specification, R1 to R5 are the same or different from each other, each independently hydrogen; deuterium; alkyl having 1 to 20 carbon atoms; cycloalkyl having 3 to 30 carbon atoms; aryl groups of 6 to 30 carbon atoms substituted or unsubstituted with alkyl, aryl or cycloalkyl groups; or a heterocyclic group having 2 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group, an aryl group or a cycloalkyl group, or adjacent groups are bonded to each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group, an aryl group or a cycloalkyl group.
In one embodiment of the present specification, R1 to R5 are the same or different from each other, each independently is hydrogen, deuterium, a substituted or unsubstituted methyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted pyridyl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted benzene ring.
In one embodiment of the present specification, R1 to R5 are the same or different from each other, each independently hydrogen; deuterium; a methyl group; an isopropyl group; a cyclohexyl group; phenyl substituted or unsubstituted with deuterium, alkyl, cycloalkyl; biphenyl substituted or unsubstituted with deuterium or cyano; a naphthyl group substituted or unsubstituted with deuterium; or a pyridyl group substituted or unsubstituted with deuterium or alkyl group, or adjacent groups are bonded to each other to form a benzene ring substituted or unsubstituted with deuterium.
In one embodiment of the present specification, R1 to R5 are the same or different from each other, each independently hydrogen; deuterium; a methyl group; an isopropyl group; a cyclohexyl group; phenyl substituted or unsubstituted with deuterium, methyl, tert-butyl or cyclohexyl; biphenyl substituted or unsubstituted with deuterium or cyano; a naphthyl group substituted or unsubstituted with deuterium; or a pyridyl group substituted or unsubstituted with deuterium or methyl, or adjacent groups combine with each other to form a benzene ring substituted or unsubstituted with deuterium.
In one embodiment of the present specification, R1 to R5 are the same or different from each other, each independently hydrogen; deuterium; a methyl group; an isopropyl group; a cyclohexyl group; phenyl substituted or unsubstituted with methyl, tert-butyl or cyclohexyl; biphenyl substituted or unsubstituted with cyano; a naphthyl group; or a pyridyl group substituted or unsubstituted with a methyl group, or adjacent groups are bonded to each other to form a benzene ring.
In one embodiment of the present specification, R1 to R5 are the same or different from each other, each independently hydrogen; a methyl group; a tertiary butyl group; or phenyl substituted or unsubstituted with cyano; biphenyl substituted or unsubstituted with cyano; or pyridyl, or adjacent groups are bonded to each other to form a benzene ring.
In one embodiment of the present description, R3 and R4 combine with each other to form a benzene ring.
In one embodiment of the present description, R4 and R5 combine with each other to form a benzene ring.
In one embodiment of the present disclosure, at least 2 of R1 to R5 are not hydrogen when adjacent groups of R1 to R5 are bonded to each other without forming a substituted or unsubstituted aromatic hydrocarbon ring.
In one embodiment of the present disclosure, at least 2 of R1 to R5 are not hydrogen or deuterium when adjacent groups of R1 to R5 are bonded to each other without forming a substituted or unsubstituted aromatic hydrocarbon ring.
In one embodiment of the present disclosure, at least 3 of R1 to R5 are not hydrogen when adjacent groups of R1 to R5 are bonded to each other without forming a substituted or unsubstituted aromatic hydrocarbon ring.
In one embodiment of the present disclosure, at least 3 of R1 to R5 are not hydrogen or deuterium when adjacent groups of R1 to R5 are bonded to each other without forming a substituted or unsubstituted aromatic hydrocarbon ring.
In one embodiment of the present specification, the above formula a is represented by any one of the following structural formulas a-1 to a-8.
In the above structural formulae A-1 to A-8, R2 to R5 are as defined in the above structural formula A,
R' is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl,
m is an integer of 0 to 4, and when m is 2 or more, 2 or more R's are the same or different from each other,
the position of the bond with the above chemical formula 1 is shown.
In one embodiment of the present specification, ar1 and Ar2 are the same as or different from each other, and each is independently represented by any one of the above structural formulas A-1 to A-8.
In one embodiment of the present specification, ar1 and Ar2 are the same as or different from each other, and are each independently represented by any one of the above structural formulas A-1 to A-4, A-7 and A-8.
In one embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-6.
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
In the above chemical formulas 1-1 to 1-6, the definitions of L1, L2, ar1 and Ar2 are the same as those in the above chemical formula 1,
the part of the benzene ring not marked with substituent is replaced by hydrogen or deuterium.
In one embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 2-1 to 2-6.
[ chemical formula 2-1]
[ chemical formula 2-2]
[ chemical formulas 2-3]
[ chemical formulas 2-4]
[ chemical formulas 2-5]
[ chemical formulas 2-6]
In the above chemical formulas 2-1 to 2-6, the definitions of X1 to X5, L1 and L2 are the same as those in the above chemical formula 1,
y1 is N or CR11, Y2 is N or CR12, Y3 is N or CR13, Y4 is N or CR14, Y5 is N or CR15,
at least 2 of Y1 to Y5 are N,
r11 to R15 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
r 'and R' are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
m and n are each integers of 0 to 4, and when m and n are each 2 or more, 2 or more R 'and R' are the same or different from each other,
the part of the benzene ring not marked with substituent is replaced by hydrogen or deuterium.
In one embodiment of the present specification, the above chemical formula 1 is represented by any one of the following chemical formulas 3-1 to 3-3.
[ chemical formula 3-1]
[ chemical formula 3-2]
[ chemical formula 3-3]
In the above chemical formulas 3-1 to 3-3, the definitions of L1, L2, ar1 and Ar2 are the same as those in the above chemical formula 1,
The part of the benzene ring not marked with substituent is replaced by hydrogen or deuterium.
In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following compounds.
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The compound represented by chemical formula 1 according to an embodiment of the present specification may manufacture a core structure by a method represented by the following general formula 1 or 2. The substituents may be bonded by methods known in the art, and the kinds, positions or numbers of the substituents may be changed according to techniques known in the art.
[ general formula 1]
In the above reaction formula 1, the definitions other than L, ar and Y are the same as those described above, L is L1 or L2, ar is Ar1 or Ar2, and Y is a halogen group, preferably a bromine group or a chlorine group.
The above reaction is a suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the suzuki coupling reaction may be varied according to techniques known in the art. The above-described production method can be more specifically described in the production example described later.
If the production formula described in the examples of the present specification and the above intermediate are appropriately combined based on common technical knowledge, all the compounds of the above chemical formula 1 described in the present specification can be produced.
At this time, the compound belonging to the range of the above chemical formula 1 may be synthesized using starting materials, intermediate materials, and the like known in the art and by synthetic methods known in the art.
In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by the above chemical formula 1. In addition, in the present specification, by introducing various substituents into the core structure of the structure shown above, HOMO and LUMO energy levels of the compound can also be adjusted.
In addition, the present specification provides an organic light emitting device including the above-mentioned compound.
In this specification, when it is indicated that a certain member is located "on" another member, it includes not only the case where the certain member is in contact with the other member but also the case where another member exists between the two members.
In the present specification, when a certain component is referred to as "including" or "comprising" a certain component, unless otherwise specified, it means that other components may be further included, and not excluded.
The organic light emitting device according to the present specification is characterized by comprising: an anode, a cathode, and 1 or more organic layers provided between the anode and the cathode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
The organic light emitting device of the present specification can be manufactured by a general method and material for manufacturing an organic light emitting device, except that the organic layer is formed by using the compound of chemical formula 1.
The compound may be used not only in the vacuum vapor deposition method but also in the solution coating method to form an organic layer in the production of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
The organic layer of the organic light-emitting device of the present specification may be formed of a single-layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including 1 or more of a hole transporting layer, a hole injecting layer, an electron blocking layer, a hole transporting and injecting layer, an electron transporting layer, an electron injecting layer, a hole blocking layer, and an electron transporting and injecting layer as an organic layer. However, the structure of the organic light emitting device of the present specification is not limited thereto, and may include a smaller or larger number of organic layers.
In the organic light emitting device of the present specification, the organic layer may include a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer may include a compound represented by chemical formula 1 described above.
In the organic light emitting device of the present specification, the organic layer may include a hole transporting layer or a hole injecting layer, and the hole transporting layer or the hole injecting layer may include a compound represented by chemical formula 1.
In an embodiment of the present specification, the organic layer may include an electron injection layer, an electron transport and injection layer, or a hole blocking layer, and the electron injection layer, the electron transport and injection layer, or the hole blocking layer may include a compound represented by chemical formula 1.
In the organic light emitting device of the present specification, the organic layer includes an electron transporting layer, an electron injecting layer, or an electron transporting and injecting layer, and the electron transporting layer, the electron injecting layer, or the electron transporting and injecting layer may include the compound represented by chemical formula 1.
In one embodiment of the present specification, the organic layer includes an electron modulation layer, and the electron modulation layer may include a compound represented by chemical formula 1.
In one embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer includes a compound represented by chemical formula 1.
In the organic light emitting device of the present specification, the organic layer is an electron transporting and injecting layer including the compound represented by chemical formula 1.
In one embodiment of the present specification, the thickness of the organic layer including the compound of formula 1 isTo->Preferably +.>To->More preferably +.>To->
In one embodiment of the present specification, the organic layer includes a light emitting layer including the compound represented by chemical formula 1.
In one embodiment of the present specification, the organic layer includes a light emitting layer including the compound represented by chemical formula 1 as a main body.
In one embodiment of the present specification, the organic layer includes a light emitting layer including the compound represented by chemical formula 1 as a dopant.
In another embodiment, the organic layer may contain other organic compounds, metals, or metal compounds in addition to the compound represented by the chemical formula 1.
In an organic light emitting device according to an embodiment of the present specification, the light emitting layer further includes a fluorescent dopant or a phosphorescent dopant. At this time, the dopant in the light emitting layer includes 1 to 50 parts by weight with respect to 100 parts by weight of the host.
As another example, the organic layer includes a light-emitting layer including the compound represented by the chemical formula 1 as a host, and may further include another host.
In one embodiment of the present specification, the dopant includes an arylamine compound, a boron and nitrogen-containing heterocyclic compound, an Ir complex, or the like.
The organic light emitting device of the present specification may further include 1 or more organic layers among a hole transporting layer, a hole injecting layer, an electron blocking layer, an electron transporting and injecting layer, an electron transporting layer, an electron injecting layer, a hole blocking layer, and a hole transporting and injecting layer.
In an embodiment of the present specification, the organic light emitting device includes: an anode, a cathode, and at least 2 organic layers disposed between the anode and the cathode, wherein at least one of the at least 2 organic layers contains a compound represented by the chemical formula 1.
In one embodiment of the present specification, the organic layer of 2 or more layers may be two or more selected from the group consisting of a light-emitting layer, a hole-transporting layer, a hole-injecting layer, a hole-transporting and injecting layer, and an electron blocking layer.
In one embodiment of the present specification, the 2 or more organic layers may be two or more selected from the group consisting of a light-emitting layer, an electron transporting layer, an electron injecting layer, an electron transporting and injecting layer, an electron adjusting layer, and a hole blocking layer.
In one embodiment of the present specification, the organic layer includes 2 or more electron transport layers, and at least one of the 2 or more electron transport layers includes a compound represented by chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by chemical formula 1 may be contained in 1 layer of the 2 or more electron transport layers, or may be contained in each of the 2 or more electron transport layers.
In addition, in an embodiment of the present specification, when the compound is included in each of the 2 or more electron transport layers, materials other than the compound represented by the chemical formula 1 may be the same as or different from each other.
When the organic layer containing the compound represented by the above chemical formula 1 is an electron transporting layer, an electron injecting layer, or an electron transporting and injecting layer, the electron transporting layer, the electron injecting layer, or the electron transporting and injecting layer may further contain an n-type dopant or an organometallic compound. The n-type dopant or the organometallic compound may use materials known in the art, for example, a metal or a metal complex may be used.
For example, the n-type dopant or the organometallic compound may be LiQ, and is not limited thereto. The electron transporting layer, the electron injecting layer, or the electron transporting and injecting layer including the compound represented by the above chemical formula 1 may further include LiQ (Lithium Quinolate, lithium quinolinolate).
According to one example, the compound represented by chemical formula 1 above and the n-type dopant or organometallic compound above may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4. According to one example, the compound represented by chemical formula 1 above and the n-type dopant or the organometallic compound described above may be included in a weight ratio of 1:1.
In one embodiment of the present specification, the organic layer includes 2 or more hole transport layers, and at least one of the 2 or more hole transport layers includes a compound represented by chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by chemical formula 1 may be contained in 1 layer of the above-described 2 or more hole transport layers, or may be contained in each of the 2 or more hole transport layers.
In addition, in an embodiment of the present specification, when the compound represented by the above chemical formula 1 is included in each of the 2 or more hole transport layers, materials other than the compound represented by the above chemical formula 1 may be the same or different from each other.
In one embodiment of the present specification, the organic layer may include a hole injection layer or a hole transport layer including a compound including an arylamine group, a carbazole group, or a benzocarbazole group, in addition to the organic layer including the compound represented by the chemical formula 1.
In one embodiment of the present specification, the organic light-emitting device may have a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate.
In one embodiment of the present specification, the organic light emitting device may be an organic light emitting device having a reverse structure (inverted type) in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate.
In the organic light emitting device of the present invention, the organic layer may include an electron blocking layer, and the electron blocking layer may use materials known in the art.
For example, the above-described organic light emitting device may have a laminated structure as shown below, but is not limited thereto.
(1) Anode/hole transport layer/light emitting layer/cathode
(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode
(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode
(4) Anode/hole transport layer/light emitting layer/electron transport layer/cathode
(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode
(7) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode
(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(10) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(11) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(12) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(13) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(14) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode
(15) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode
(16) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode
(17) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode
(18) Anode/hole injection layer/first hole transport layer/second hole transport layer/light emitting layer/electron injection and transport layer/cathode
(19) Anode/hole injection layer/first hole transport layer/second hole transport layer/light emitting layer/hole blocking layer/electron injection and transport layer/cathode
(20) Anode/hole injection layer/hole transport layer/light emitting layer/electron injection and transport layer/cathode
The structure of the organic light emitting device of the present specification may have the structure shown in fig. 1 to 4, but is not limited thereto.
Fig. 1 illustrates an example of an organic light emitting device in which a substrate 1, an anode 2, an organic layer 10, and a cathode 9 are stacked in this order. In the structure described above, the above-described compound may be contained in the above-described light-emitting layer 5.
Fig. 2 illustrates an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 9 are stacked in this order. In the structure described above, the above-described compound may be contained in the above-described hole injection layer 3, hole transport layer 4, light-emitting layer 5, electron transport layer 6, or electron injection layer 7.
Fig. 3 illustrates an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4-1, a second hole transport layer 4-2, a light-emitting layer 5, an electron transport and injection layer 8, and a cathode 9 are stacked in this order. In the structure described above, the above-mentioned compound may be contained in the above-mentioned hole injection layer 3, the first hole transport layer 4-1, the second hole transport layer 4-2, the light-emitting layer 5, or the electron transport and injection layer 8.
Fig. 4 illustrates an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport and injection layer 8, and a cathode 9 are stacked in this order. In the structure described above, the above-described compound may be contained in the above-described hole injection layer 3, hole transport layer 4, light-emitting layer 5, or electron transport and injection layer 8.
In an embodiment of the present disclosure, the electron transporting and injecting layer and the light emitting layer may be disposed adjacent to each other.
In an embodiment of the present disclosure, the electron transport layer and the light emitting layer may be disposed adjacent to each other.
In an embodiment of the present disclosure, the electronic adjusting layer and the light emitting layer may be disposed adjacent to each other.
In an embodiment of the present disclosure, the hole blocking layer and the light emitting layer may be disposed adjacent to each other.
In an embodiment of the present disclosure, the hole blocking layer and the electron transporting layer may be disposed adjacent to each other.
The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that 1 or more of the organic layers include the above compound, i.e., the compound represented by chemical formula 1.
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 device according to the present specification may be manufactured as follows: PVD (physical vapor deposition) such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation) 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, an electron blocking layer, an electron transport layer, and an electron injection layer is formed on the anode, and then a substance that can function as a cathode is vapor deposited on the organic layer to manufacture the anode. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
The organic layer may further include one or more of a hole transporting layer, a hole injecting layer, an electron blocking layer, an electron transporting and injecting layer, an electron transporting layer, an electron injecting layer, a hole blocking layer, and a hole transporting and injecting layer.
The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, or the like, but is not limited thereto, and may have a single-layer structure. The organic layer may be formed into a smaller number of layers by a solvent process (solvent process) other than vapor deposition, such as spin coating, dip coating, knife coating, screen printing, ink jet printing, or thermal transfer printing, using various polymer materials.
The anode is an electrode for injecting holes, and is preferably a substance having a large work function as an anode substance in order to allow holes to be smoothly injected into the organic layer. As the anode material which can be used in the present inventionSpecific examples of (a) 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, indium Zinc Oxide); 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.
The cathode is an electrode for injecting electrons, and is preferably a substance having a small work function as a cathode substance 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 functions to smooth injection of holes from the anode to the light-emitting layer, and the hole injection substance is a substance that can well receive holes from the anode at a low voltage, and preferably has a HOMO (highest occupied molecular orbital ) interposed between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substance, hexanitrile hexaazabenzophenanthrene-based organic substance, quinacridone-based organic substance, perylene-based organic substance, anthraquinone, polyaniline, and polythiophene-based conductive polymer. The thickness of the hole injection layer may be 1nm to 150nm. When the thickness of the hole injection layer is 1nm or more, there is an advantage that the degradation of the hole injection characteristic can be prevented, and when the thickness of the hole injection layer is 150nm or less, there is an advantage that the increase of the driving voltage for improving the migration of holes can be prevented.
In one embodiment of the present specification, the hole injection layer may include a diamine compound including an aryl group or a heteroaryl group. According to one example, the amine compound may have a structure in which an amine group is bonded to a spiroacridine fluorene structure.
The hole transport layer can function to smooth the transport of holes. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring the holes to the light-emitting layer, and a substance having a large mobility to the holes is suitable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
In one embodiment of the present specification, the hole transport layer may contain 1 or more cyano group-containing N-polycyclic compound or carbazolyl group-containing amine compound. In this case, the N-containing polycyclic compound may be 1,4,5,8,9,11-hexaazabenzophenanthrene hexacarbonitrile (1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile, HATCN). According to one example, the hole transport layer may contain 2 or more kinds of the above-mentioned compounds alone or in combination. According to another example, the HATCN may be vapor-deposited to serve as the first hole transport layer, and the amine compound containing a carbazolyl group may be vapor-deposited to serve as the second hole transport layer.
A hole buffer layer may be further provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.
An electron blocking layer may be disposed between the hole transport layer and the light emitting layer. The above-mentioned compounds or materials known in the art may be used in the above-mentioned electron blocking layer.
The light-emitting layer may emit red, green, or blue light, and may be formed of a phosphorescent material or a fluorescent material. The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. Specifically, there are 8-hydroxy-quinoline 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.
Examples of the host material of the light-emitting layer include an aromatic condensed ring derivative and a heterocyclic compound. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds Pyrimidine derivatives, etc., but are not limited thereto.
When the light-emitting layer emits red light, as a light-emitting dopant, a phosphorescent substance such as PIQIr (acac) (bi (1-phenylisoquinoline) acetylacetonide), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium), bis (1-phenylquinoline) acetylacetonate iridium), PQIr (tris (1-phenylquinoline) irium, tris (1-phenylquinoline) iridium), ptOEP (octaethylporphyrin platinum, platinum octaethylporphyrin), or Alq may be used 3 Fluorescent substances such as (tris (8-hydroxyquinoline) aluminum, etc., but not limited thereto. When the light emitting layer emits green light, ir (ppy) can be used as a light emitting dopant 3 Phosphorescent substances such as (factris (2-phenylpyridine) iridium, planar tris (2-phenylpyridine) iridium), or Alq 3 Fluorescent substances such as (tris (8-hydroxyquinoline) aluminum), but are not limited thereto. When the light-emitting layer emits blue light, as the light-emitting dopant, (4, 6-F 2 ppy) 2 Examples of the fluorescent substance include, but are not limited to, phosphorescent substances such as Irpic, fluorescent substances such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), distyrylbenzene (DS B), distyrylarylene (DSA), PFO-based polymers, and PPV-based polymers.
In one embodiment of the present disclosure, the light-emitting layer may include an anthracene compound substituted with an aryl group or a heterocyclic group as a host, and may include a pyrene compound substituted with an amine group as a dopant. According to one example, the anthracene compound is a structure in which carbon number 9 and carbon number 10 are substituted with an aryl or heterocyclic group. The host and dopant may be included in a suitable weight ratio, and according to one example, the host and dopant may be included in a weight ratio of 100:1 to 100:10, respectively.
A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.
The electron transport layer can play a role in enabling electron transport to be smooth. The electron transporting substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having high mobility of electrons. As specific examples, there are the above-mentioned compounds or Al complexes of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The thickness of the electron transport layer may be 1nm to 50nm. When the thickness of the electron transport layer is 1nm or more, there is an advantage that the degradation of the electron transport property can be prevented, and when it is 50nm or less, there is an advantage that the increase of the driving voltage for the purpose of improving the electron transfer can be prevented when the thickness of the electron transport layer is too thick.
In an embodiment of the present specification, the electron transport layer may include the compound represented by chemical formula 1 of the present invention, and may further include an n-type dopant or an organometallic compound. According to one example, the above n-type dopant or organometallic compound may be LiQ, and the compound represented by chemical formula 1 of the present invention and the above n-type dopant (or organometallic compound) may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.
The electron injection layer can perform a function of smoothly injecting electrons. As the electron injecting substance, the following compounds are preferable: 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,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 hole blocking layer is a layer that prevents holes from reaching the cathode, and can be formed generally under the same conditions as those of the hole injection layer. Specifically, there areThe diazole derivative, triazole derivative, phenanthroline derivative, BCP, aluminum complex (aluminum complex), and the like, but are not limited thereto.
The organic light emitting device according to the present invention may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
The organic light emitting device according to the present specification may be included in various electronic apparatuses to be used. For example, the electronic device may be a display panel, a touch panel, a solar module, a lighting device, or the like, but is not limited thereto.
Modes for carrying out the invention
In the following, examples will be given to explain the present specification in detail. However, the embodiments according to the present specification may be modified into various forms, and the scope of the present application is not to be construed as limited to the embodiments described in detail below. The embodiments of the present application are provided to more fully explain the present description to those skilled in the art.
Synthesis example
Synthesis example 1: production of Compound E1
E1-A (20 g,59.3 mmol) and E1-B (48.4 g,118.6mm mol) were added to 400ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (24.6 g,178 mmol) was dissolved in 25ml of water and added thereto, and after stirring well, tetrakis (triphenylphosphine palladium) (2.1 g,1.8 mmol) was added thereto. After 3 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. This was again poured into 878mL of chloroform and dissolved, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to yield compound E1 (29.9 g, 68%) as a white solid.
MS:[M+H] + ＝740
Synthesis example 2: production of Compound E2
The compound E2 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝794
Synthesis example 3: production of Compound E3
The compound E3 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝792
Synthesis example 4: production of Compound E4
The compound E4 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H]+＝794
Synthesis example 5: production of Compound E5
The compound E5 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H]+＝794
Synthesis example 6: production of Compound E6
The compound E6 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H]+＝794
Synthesis example 7: production of Compound E7
The compound E7 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝850
Synthesis example 8: production of Compound E8
The compound E8 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝958
Synthesis example 9: production of Compound E9
The compound E9 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝792
Synthesis example 10: production of Compound E10
The compound E10 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝894
Synthesis example 11: production of Compound E11
The compound E11 was produced by the same method as the production method of synthesis example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝796
Synthesis example 12: production of Compound E12
E12-A (20 g,50.4 mmol) and E12-B (16.3 g,50.4 mmol) were added to 400ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (20.9 g,151.2 mmol) was dissolved in 21ml of water and charged, and after stirring well, tetrakis (triphenylphosphine palladium) (1.7 g,1.5 mmol) was charged. After 2 hours of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. This was again poured into 563mL of chloroform and dissolved, and after washing with water 2 times, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to yield compound E12 (14.9 g, 53%) as a white solid.
MS:[M+H] + ＝559
Synthesis example 13: production of Compound E13
The compound E13 was produced by the same method as the production method of synthesis example 12, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝794
Synthesis example 14: production of Compound E14
The compound E14 was produced by the same method as the production method of synthesis example 12, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝794
Synthesis example 15: production of Compound E15
The compound E15 was produced by the same method as the production method of synthesis example 12, except that each starting material was used as in the above reaction formula.
MS:[M+H] + ＝767
Experimental example
Experimental example 1
ITO (indium tin oxide) toThe glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei-hill (fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbox (millipore co.). After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, the following compound HI-A was usedAnd performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, hexanitrile hexaazatriphenylene (HAT,) of the formula>) And the following compounds->Vacuum evaporation is sequentially performed to form a hole transport layer.
Then, on the hole transport layer, the film thickness is set to beThe following compounds BH and BD were vacuum-evaporated at a weight ratio of 25:1 to form a light-emitting layer.
On the light-emitting layer, the compound E1 produced in Synthesis example 1 and the following compound [ LiQ ]]Vacuum evaporation was performed at a weight ratio of 1:1 to obtain a solution of lithium quinolineForm electron transport and injection layers. On the electron transport and injection layer, lithium fluoride (LiF) is added in sequence +.>Is made of aluminum +.>And vapor deposition is performed to form a cathode.
In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride maintenance of cathode/sec->Vapor deposition rate per second, aluminum maintenance->Vapor deposition rate per second, vacuum degree was maintained at 1×10 during vapor deposition -7 ～5×10 -8 The support is thus fabricated into an organic light emitting device.
Experimental examples 2 to 15
An organic light emitting device was manufactured by the same method as in experimental example 1, except that the compound of table 1 below was used instead of the compound E1 of experimental example 1.
Comparative examples 1 to 8
An organic light emitting device was manufactured by the same method as in experimental example 1, except that the compound of table 1 below was used instead of the compound E1 of experimental example 1. The compounds of ET-1 to ET-8 used in table 1 below are shown below.
The organic light-emitting devices manufactured in the above experimental examples and comparative experimental examples were subjected to a temperature of 10mA/cm 2 The driving voltage, luminous efficiency and color coordinates were measured at a current density of 20mA/cm 2 The time (T) at which the initial luminance was 90% was measured at the current density of (2) 90 ). The results are shown in table 1 below.
TABLE 1
As described in the above table 1, it was confirmed that the organic light emitting device using the compound represented by chemical formula 1 of the present invention was excellent in voltage, efficiency and/or lifetime (T 90 ) The composition exhibits excellent characteristics.
Specifically, the compound represented by chemical formula 1 of the present invention is characterized in that an N-containing ring group represented by chemical formula a is attached to a benzene ring containing a cyano group through a linking group, and the electron mobility is increased due to 2N-containing ring groups in the molecule, so that the efficiency of the organic light emitting device is increased, and the preferred LUMO level is formed as an electron transporting and injecting layer by the above-described N-containing ring group being attached to the parent structure not directly but through a linking group, and thus the electron injecting effect into the light emitting layer is increased, and 1 cyano group is contained in the molecule to adjust the electron injecting characteristics, thereby showing the result of increasing the lifetime of the organic light emitting device.
Comparing experimental examples 1 to 15 of table 1 with comparative experimental examples 1 to 2, it was confirmed that the organic light emitting device including the compound of chemical formula 1 of the present invention showed significantly superior characteristics in terms of efficiency and lifetime compared to the case where the number of N-ring groups is 1.
Comparing experimental examples 1 to 15 of table 1 with comparative experimental examples 3 to 5, it was confirmed that the organic light emitting device including the compound of chemical formula 1 of the present invention showed significantly excellent characteristics in terms of efficiency and lifetime compared to the compound in which biphenylene is not substituted with cyano.
Comparing experimental examples 1 to 15 of table 1 with comparative experimental examples 6 to 7, it was confirmed that the organic light emitting device including the compound of chemical formula 1 of the present invention showed significantly superior characteristics in efficiency and lifetime compared to the compound in which the parent nucleus structure is not substituted with biphenylene but is substituted with naphthalene.
Comparing experimental examples 1 to 15 of table 1 with comparative experimental example 8, it was confirmed that the organic light emitting device including the compound of chemical formula 1 of the present invention showed significantly superior characteristics in efficiency and lifetime compared to the compound having an N-ring group represented by chemical formula a directly connected thereto.

Claims (12)

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,
l1 and L2 are the same or different from each other and are each independently a substituted or unsubstituted arylene group,
ar1 and Ar2 are the same as or different from each other and are each independently represented by the following chemical formula A,
the part of the benzene ring without the indicated substituent is replaced by hydrogen or deuterium,
[ chemical formula A ]
In the chemical formula a, in which the amino acid is represented by the formula a,
x1 is N or CR1, X2 is N or CR2, X3 is N or CR3, X4 is N or CR4, X5 is N or CR5,
at least 2 of X1 to X5 are N,
r1 to R5 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or are combined with each other with the adjacent groups to form a substituted or unsubstituted aromatic hydrocarbon ring,
represents the position bound to the chemical formula 1.
2. The compound of claim 1, wherein the formula a is represented by any one of the following structural formulas a-1 to a-8:
in the structural formulae A-1 to A-8, R2 to R5 are as defined in the structural formula A,
r' is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl,
m is an integer of 0 to 4, and when m is 2 or more, 2 or more R's are the same or different from each other,representation and representationThe position where the chemical formula 1 binds.
3. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-6:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
In the chemical formulas 1-1 to 1-6, the definitions of L1, L2, ar1 and Ar2 are the same as those in the chemical formula 1,
the part of the benzene ring not marked with substituent is replaced by hydrogen or deuterium.
4. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 2-1 to 2-6:
[ chemical formula 2-1]
[ chemical formula 2-2]
[ chemical formulas 2-3]
[ chemical formulas 2-4]
[ chemical formulas 2-5]
[ chemical formulas 2-6]
In the chemical formulas 2-1 to 2-6, the definitions of X1 to X5, L1 and L2 are the same as those in the chemical formula 1,
y1 is N or CR11, Y2 is N or CR12, Y3 is N or CR13, Y4 is N or CR14, Y5 is N or CR15,
at least 2 of Y1 to Y5 are N,
r11 to R15 are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
R 'and R' are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
m and n are each integers of 0 to 4, and when m and n are each 2 or more, 2 or more R 'and R' are the same or different from each other,
the part of the benzene ring not marked with substituent is replaced by hydrogen or deuterium.
5. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 3-1 to 3-3:
[ chemical formula 3-1]
[ chemical formula 3-2]
[ chemical formula 3-3]
In the chemical formulas 3-1 to 3-3, the definitions of L1, L2, ar1 and Ar2 are the same as those in the chemical formula 1,
the part of the benzene ring not marked with substituent is replaced by hydrogen or deuterium.
6. The compound of claim 1, wherein L1 and L2 are phenylene substituted or unsubstituted with deuterium.
7. The compound of claim 1, wherein the chemical formula 1 is represented by any one of the following compounds:
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/>
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8. an organic light emitting device, comprising: an anode, a cathode, and 1 or more organic layers disposed between the anode and the cathode, the 1 or more of the organic layers comprising the compound of any one of claims 1 to 7.
9. The organic light-emitting device of claim 8, wherein the organic layer comprises an electron transport layer, an electron injection layer, or an electron transport and injection layer, the electron transport layer, electron injection layer, or electron transport and injection layer comprising the compound.
10. The organic light emitting device of claim 9, wherein the electron transport layer, electron injection layer, or electron transport and injection layer further comprises an n-type dopant or an organometallic compound.
11. The organic light emitting device of claim 10, wherein the compound and the n-type dopant or organometallic compound are included in a weight ratio of 2:8 to 8:2.
12. The organic light-emitting device according to claim 8, wherein the organic layer further comprises 1 or more of a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer.
CN202380012748.0A 2022-03-10 2023-03-10 Compound and organic light emitting device comprising the same Pending CN117616024A (en)

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