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CN114364660B - 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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CN114364660B
CN114364660B CN202080061109.XA CN202080061109A CN114364660B CN 114364660 B CN114364660 B CN 114364660B CN 202080061109 A CN202080061109 A CN 202080061109A CN 114364660 B CN114364660 B CN 114364660B
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CN114364660A (en
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许东旭
洪性佶
韩美连
尹俊
尹正民
尹喜敬
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LG Chem Ltd
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Abstract

The present specification provides 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. 10-2019-0150327, filed in the korean patent office on 11/21 in 2019, the entire contents of which are included in the present specification.
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 (exciton) are formed, and light is emitted when the excitons re-transition to the ground state.
There is a continuing need to develop new materials for use in organic light emitting devices as described above.
[ Prior Art literature ]
(Patent document 1) KR10-1787195B1
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,
R1 is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
Ar1 and Ar2 are the same as or different from each other, each independently a substituted or unsubstituted monocyclic, bicyclic, tetracyclic or more ring aryl group, or any one of the following formulae A1 to A4,
[ Chemical formula A1]
[ Chemical formula A2]
[ Chemical formula A3]
[ Chemical formula A4]
In the above chemical formulas A1 to A4,
X1 is N or CR11, X2 is N or CR12, X3 is N or CR13, X4 is N or CR14, X5 is N or CR15,
At least one of X1 to X5 is N,
Y is O, S or NR23, and the like,
R11 to R15 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
R21 and R22 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
One of R23, G1 and G2 is linked to formula 1, and the others are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
R1 is an integer of 0 to 14,
M and n are each an integer of 1 to 5,
N21 is an integer of 0 to 7,
N22 is an integer of 0 to 5,
G2 is an integer of 0 to 4,
When r1, m, n21, n22 and g2 are each 2 or more, substituents in parentheses of 2 or more are the same or different from each other,
The dotted line is the portion connected to chemical formula 1.
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. According to the compound of at least one embodiment, the thermal stability of the molecule is improved, and an improvement in efficiency, a low driving voltage, and/or an improvement in lifetime characteristics can be achieved 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, compared to the existing organic light emitting device, it has the effects of low driving voltage, high efficiency, or long life.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device in which a substrate 1, an anode 2, a light-emitting layer 5, and a cathode 7 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 injection and transport layer 6, and a cathode 7 are stacked in this order.
[ Description of symbols ]
1: Substrate board
2: Anode
3: Hole injection layer
4: Hole transport layer
5: Light-emitting layer
6: Electron injection and transport layers
7: Cathode electrode
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, and not 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 specification, examples of substituents are described below, but are not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom or the like 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 1 or 2 or more substituents selected from deuterium, halogen group, nitrile group (-CN), 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 2 or more substituents selected from the above exemplified substituents, or does not have any substituent. 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 groups, nitrile groups, alkoxy groups, aryloxy groups, alkyl groups, cycloalkyl groups, aryl groups, and heterocyclic groups, or substituted with 2 or more substituents selected from the above-exemplified substituents, 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 the chemical formula of-SiY aYbYc, and the above Y a、Yb and Y c may each 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 the chemical formula of-BY dYe, and the above Y d and Y e may each 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-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, 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, and the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, a combination thereof, and the like may be substituted on the above-mentioned amine group. 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 group, dimethylamino group, ethylamino group, diethylamino group, phenylamino group, 9-dimethylfluorenylphenylamino group, pyridylphenylamino group, diphenylamino group, phenylpyridylamino group, naphthylamino group, biphenylamino group, anthracenyl amino group, dibenzofuranylphenylamino group, 9-methylanthrenylamino group, phenylnaphthylamino group, xylylamino group, phenyltolylamino group and the like.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. In the above aryl group, the monocyclic aryl group may be phenyl, biphenyl, terphenyl, tetrabiphenyl, or the like, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, and the like,A group, a fluorenyl group, 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 the case where the above fluorenyl group is substituted, it may beAn 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 heterocyclic group is a ring group containing 1 or more hetero atoms of 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. 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 aromatic, and the above description of the heterocyclic group can be applied thereto.
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 aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from the cycloalkyl or aryl group as exemplified above, except for the 2-valent group.
In this specification, the meaning of a ring formed by bonding adjacent groups to each other is 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 a condensed ring thereof is 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 means a ring containing 1 or more 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 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 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-Alkane (1, 4-dioxane), pyrrolidine, piperidine, morpholine (morpholine), oxepane, azacyclooctane, thiacyclooctane, 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, isoOxazole, thiazole, isothiazole, triazole,Diazoles, thiadiazoles, dithiazoles, tetrazoles, pyrans, thiopyrans, pyridazines,Oxazine, thiazide, twoAlkene, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, naphthyridine, triazaindene, indole, indolizine, benzothiazole, benzoOxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoneOxazine, 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 present specification provides a compound represented by the following chemical formula 1. The compound represented by the following chemical formula 1 improves thermal stability of molecules, and thus, when used in an organic layer of an organic light emitting device, not only improves efficiency of the organic light emitting device, but also has a low driving voltage and excellent lifetime characteristics.
Next, the above chemical formula 1 will be described in detail.
[ Chemical formula 1]
In the above-mentioned chemical formula 1,
R1 is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
Ar1 and Ar2 are the same as or different from each other, each independently a substituted or unsubstituted monocyclic, bicyclic, tetracyclic or more ring aryl group, or any one of the following formulae A1 to A4,
[ Chemical formula A1]
[ Chemical formula A2]
[ Chemical formula A3]
[ Chemical formula A4]
In the above chemical formulas A1 to A4,
X1 is N or CR11, X2 is N or CR12, X3 is N or CR13, X4 is N or CR14, X5 is N or CR15,
At least one of X1 to X5 is N,
Y is O, S or NR23, and the like,
R11 to R15 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
R21 and R22 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
One of R23, G1 and G2 is linked to formula 1, and the others are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
R1 is an integer of 0 to 14,
M and n are each an integer of 1 to 5,
N21 is an integer of 0 to 7,
N22 is an integer of 0 to 5,
G2 is an integer of 0 to 4,
When r1, m, n21, n22 and g2 are each 2 or more, substituents in parentheses of 2 or more are the same or different from each other,
The dotted line is the portion connected to chemical formula 1.
In one embodiment of the present specification, R1 is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, R1 is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 3 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.
In one embodiment of the present specification, R1 is hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 15 carbon atoms, a substituted or unsubstituted alkynyl group having 3 to 15 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.
In one embodiment of the present specification, R1 is hydrogen or deuterium.
In one embodiment of the present specification, R1 is hydrogen.
In an embodiment of the present specification, the above Ar1 and Ar2 are the same or different from each other, each independently is a substituted or unsubstituted monocyclic, bicyclic, tetracyclic or more ring aryl group, or any one of the above formulas A1 to A4.
In an embodiment of the present specification, ar1 and Ar2 described above are the same or different from each other, and each is independently a substituted or unsubstituted monocyclic, bicyclic, tetracyclic or more-ring aryl group having 6 to 60 carbon atoms, or any one of the chemical formulas A1 to A4 described above.
In an embodiment of the present specification, ar1 and Ar2 described above are the same or different from each other, and each is independently a substituted or unsubstituted monocyclic, bicyclic, tetracyclic or more-ring aryl group having 6 to 30 carbon atoms, or any one of the chemical formulas A1 to A4 described above.
In an embodiment of the present specification, ar1 and Ar2 described above are the same or different from each other, and each is independently a substituted or unsubstituted monocyclic, bicyclic, tetracyclic or more-ring aryl group having 6 to 20 carbon atoms, or any one of the chemical formulas A1 to A4 described above.
In an embodiment of the present specification, the above Ar1 and Ar2 are the same or different from each other, each independently is a substituted or unsubstituted monocyclic, bicyclic, or tetracyclic aryl group, or any one of the above formulas A1 to A4.
In an embodiment of the present specification, each of Ar1 and Ar2 which are the same or different from each other, is an optionally substituted monocyclic, bicyclic or tetracyclic aryl group substituted or unsubstituted by 1 or more groups selected from the group consisting of deuterium, nitrile, alkyl and heterocyclic groups or by 2 or more groups selected from the group consisting of the above groups, or any one of the above chemical formulas A1 to A4.
According to an embodiment of the present specification, each of the above Ar1 and Ar2 is the same or different from each other, and is a monocyclic, bicyclic, or tetracyclic aryl group substituted or unsubstituted with 1 or more groups selected from deuterium, a nitrile group, an alkyl group having 1 to 20 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms containing N, O or S, or a group selected from 2 or more groups connected in the above group, or any one of the above chemical formulas A1 to A4.
In an embodiment of the present specification, each of the above Ar1 and Ar2 is the same or different from each other, and is an aryl group substituted or unsubstituted with 1 or more groups selected from the group consisting of deuterium, nitrile group, ethyl group and benzimidazole group, or groups formed by joining 2 or more groups selected from the group, or any one of the above chemical formulas A1 to A4.
In an embodiment of the present specification, the above Ar1 and Ar2 are the same or different from each other, and each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluoranthenyl group, or any one of the above chemical formulas A1 to A4.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and each is independently a phenyl group substituted or unsubstituted with 1 or more groups selected from the group consisting of deuterium, nitrile group, alkyl group, and heterocyclic group, or 2 or more groups selected from the group consisting of the above groups; biphenyl groups substituted or unsubstituted with 1 or more groups selected from the group consisting of deuterium, nitrile groups, alkyl groups and heterocyclic groups, or 2 or more groups selected from the group consisting of the above groups; a naphthyl group which is substituted or unsubstituted with 1 or more groups selected from the group consisting of deuterium, nitrile group, alkyl group and heterocyclic group, or 2 or more groups selected from the group consisting of the above groups; or a fluoranthenyl group substituted or unsubstituted with 1 or more groups selected from the group consisting of deuterium, nitrile group, alkyl group and heterocyclic group or 2 or more groups selected from the above group, or any one of the above chemical formulas A1 to A4.
According to an embodiment of the present specification, the above Ar1 and Ar2 are the same or different from each other, and each is independently a benzimidazolyl group substituted with an alkyl group or a phenyl group substituted with a nitrile group or unsubstituted, a biphenyl group substituted with a nitrile group or unsubstituted, a naphthyl group, or a fluoranthenyl group, or any one of the above chemical formulas A1 to A4.
In an embodiment of the present specification, the above Ar1 and Ar2 are the same or different from each other, and each is independently a benzoimidazolyl group substituted with an ethyl group or a nitrile group or an unsubstituted phenyl group, a biphenyl group substituted with a nitrile group or an unsubstituted naphthyl group, or a fluoranthenyl group, or any one of the above chemical formulas A1 to A4.
In one embodiment of the present specification, when Ar1 and Ar2 are substituted or unsubstituted monocyclic, bicyclic or tetracyclic or more aryl groups, the substituted or unsubstituted monocyclic, bicyclic or tetracyclic or more aryl groups are represented by any one of the following structural formulae.
In the above structural formula, a dotted line indicates a portion connected to the above chemical formula 1.
In an embodiment of the present specification, the above Ar1 and Ar2 are the same or different from each other, and each is independently a phenyl group substituted or unsubstituted with a benzimidazolyl group substituted with an ethyl group or a nitrile group, a biphenyl group substituted or unsubstituted with a nitrile group, or a fluoranthenyl group, or any one of the above chemical formulas A1 to A4.
In an embodiment of the present specification, the above Ar1 and Ar2 are the same or different from each other, and each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluoranthenyl group, or any one of the above chemical formulas A1 to A4.
In an embodiment of the present specification, the above Ar1 and Ar2 are the same or different from each other, and each is independently a benzimidazolyl group substituted with an ethyl group or a nitrile group or an unsubstituted phenyl group, a biphenyl group substituted with a nitrile group or an unsubstituted biphenyl group, or a fluoranthenyl group, or any one of the above chemical formulas A1 to A4.
In one embodiment of the present disclosure, X1 is N, and X2 to X5 are CR12 to CR15.
In one embodiment of the present specification, X2 is N, and X1 and X3 to X5 are CR11 and CR13 to CR15, respectively.
In one embodiment of the present specification, X3 is N, and X1, X2, X4, and X5 are CR11, CR12, CR14, and CR15, respectively.
In one embodiment of the present specification, X1 and X3 are N, and X2, X4 and X5 are CR12, CR14 and CR15, respectively.
In one embodiment of the present specification, X1 and X2 are N, and X3 to X5 are CR13 to CR15, respectively.
In one embodiment of the present specification, X1 and X3 are N, and X2, X4 and X5 are CR12, CR14 and CR15, respectively.
In one embodiment of the present specification, X1 and X5 are N, and X2 to X4 are CR12 to CR14, respectively.
In one embodiment of the present disclosure, X1, X3 and X5 are N, and X2 and X4 are CR12 and CR14, respectively.
In one embodiment of the present specification, X1, X2 and X5 are N, and X3 and X4 are CR13 and CR14, respectively.
In one embodiment of the present specification, X1, X2, X4 and X5 are N, and X3 is CR13.
In one embodiment of the present specification, the chemical formula A1 is represented by any one of the following structural formulas.
In the above structural formula, the definitions of R11 to R15 are the same as those in the chemical formula A1, and the dotted line represents a site connected to the above chemical formula 1.
In one embodiment of the present specification, the chemical formula A1 is represented by any one of the following structural formulas.
In the above structural formula, the definitions of R11 to R15 are the same as those in the chemical formula A1, and the dotted line represents a site bonded to the above chemical formula 1.
In an embodiment of the present specification, the above R11 to R15 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, R11 to R15 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 30 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.
In one embodiment of the present specification, R11 to R15 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 20 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.
In an embodiment of the present specification, R11 to R15 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.
In an embodiment of the present specification, R11 to R15 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms and containing N, O or S.
In an embodiment of the present specification, each of R11 to R15 is the same or different from each other, and is independently hydrogen, deuterium, fluoro, nitrile, substituted or unsubstituted methyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, or substituted or unsubstituted benzimidazolyl.
In an embodiment of the present specification, each of the above R11 to R15 is the same or different from each other, and is independently hydrogen, deuterium, fluoro, nitrile, methyl, phenyl substituted or unsubstituted with alkyl, biphenyl substituted or unsubstituted with alkyl, naphthyl substituted or unsubstituted with alkyl, pyridinyl substituted or unsubstituted with alkyl, or benzimidazolyl substituted or unsubstituted with alkyl.
In an embodiment of the present specification, each of R11 to R15 is the same as or different from each other, and is independently hydrogen, deuterium, fluoro, nitrile, methyl, phenyl substituted or unsubstituted with methyl, biphenyl, naphthyl, pyridyl substituted or unsubstituted with methyl, or benzimidazolyl substituted or unsubstituted with ethyl.
In one embodiment of the present specification, R11 to R15 are the same or different from each other and each is independently hydrogen, deuterium, nitrile group, methyl group, phenyl group, or a pyridyl group substituted or unsubstituted with methyl group.
In one embodiment of the present specification, R11 to R15 are the same or different from each other and each is independently hydrogen, nitrile group, methyl group, phenyl group, or pyridyl group substituted or unsubstituted with methyl group.
In one embodiment of the present specification, the chemical formula A1 is represented by any one of the following structural formulas.
In the above structural formula, the dotted line refers to a portion bonded to chemical formula 1.
In one embodiment of the present specification, R21 and R22 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In an embodiment of the present specification, R21 and R22 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 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.
In one embodiment of the present specification, R21 and R22 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 15 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.
In one embodiment of the present specification, R21 and R22 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted hetero ring having 2 to 20 carbon atoms.
In one embodiment of the present specification, R21 and R22 are the same or different from each other, and each is independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted methyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted furyl group.
In one embodiment of the present specification, R21 and R22 are the same or different from each other, and each is independently hydrogen, deuterium, methyl, phenyl, naphthyl or furyl.
In one embodiment of the present specification, R21 and R22 are the same or different from each other, and each is independently hydrogen, deuterium, a nitrile group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted methoxy group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.
In one embodiment of the present specification, the above chemical formula A2 is represented by the following chemical formula A2-1.
[ Chemical formula A2-1]
In the above chemical formula A2-1, R21 and n21 are as defined in the above chemical formula A2.
In one embodiment of the present specification, R21 is hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.
In one embodiment of the present specification, R21 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
In one embodiment of the present specification, R21 is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In one embodiment of the present specification, R21 is hydrogen, deuterium, a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group.
In one embodiment of the present specification, R21 is hydrogen, deuterium, methyl or phenyl.
In one embodiment of the present specification, R21 is hydrogen, methyl or phenyl.
In one embodiment of the present specification, n21 is 0 or 1.
In one embodiment of the present specification, the chemical formula A2 is represented by any one of the following structural formulas.
In the above structural formula, the dotted line indicates a portion bonded to the above chemical formula 1.
In one embodiment of the present specification, the above formula A3 is represented by the following formula A3-1 or A3-2.
[ Chemical formula A3-1]
[ Chemical formula A3-2]
In the above chemical formulas A3-1 and A3-2, R22 and n22 are as defined in the above chemical formula A3.
In one embodiment of the present specification, R22 is hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, R22 is hydrogen, deuterium, 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.
In one embodiment of the present specification, R22 is hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
In one embodiment of the present specification, R22 is hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted furyl.
In one embodiment of the present specification, R22 is hydrogen, deuterium, phenyl, naphthyl or furyl.
In one embodiment of the present specification, R22 is hydrogen, phenyl, naphthyl or furyl.
In one embodiment of the present disclosure, n22 is 0 or 1.
In one embodiment of the present specification, the chemical formula A3 is represented by any one of the following structural formulas.
In the above structural formula, the dotted line indicates a portion bonded to the above chemical formula 1.
In one embodiment of the present specification, one of R23, G1 and G2 is connected to formula 1, and the others are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In one embodiment of the present specification, one of R23, G1 and G2 is connected to formula 1, and the others are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 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.
In one embodiment of the present specification, one of R23, G1 and G2 is connected to formula 1, and the others are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 15 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.
In one embodiment of the present specification, one of R23, G1 and G2 is connected to formula 1, and the others are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.
In one embodiment of the present specification, one of R23, G1 and G2 is connected to formula 1, and the others are the same or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, or substituted or unsubstituted aryl.
In one embodiment of the present specification, one of R23, G1 and G2 is connected to formula 1, and the others are the same or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted ethyl, substituted or unsubstituted methoxy, or substituted or unsubstituted phenyl.
In one embodiment of the present specification, one of R23, G1 and G2 is connected to formula 1, and the others are the same or different from each other, and each is independently hydrogen, deuterium, ethyl, methoxy or phenyl.
In one embodiment of the present specification, one of R23, G1 and G2 is connected to formula 1, and the others are the same or different from each other, and each is independently hydrogen, deuterium, ethyl or phenyl.
In one embodiment of the present specification, R23 is ethyl or phenyl.
In one embodiment of the present specification, R23 is connected to formula 1.
In one embodiment of the present specification, G1 is connected to chemical formula 1.
In one embodiment of the present specification, G1 is attached to formula 1, and R23 is hydrogen, deuterium, ethyl, methoxy, or phenyl.
In one embodiment of the present specification, G2 is hydrogen or deuterium.
In one embodiment of the present specification, G2 is hydrogen.
In one embodiment of the present specification, G1 and G2 not connected to the above chemical formula 1 are hydrogen.
In one embodiment of the present specification, the above chemical formula A4 is represented by any one of the following chemical formulas A4-1 to A4-3.
[ Chemical formula A4-1]
[ Chemical formula A4-2]
[ Chemical formula A4-3]
In the above formulas A4-1 to A4-3,
Y1 is O or S, and the total number of the components is equal to or less than zero,
R23 to R27 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
N24, n26 and n27 are integers from 0 to 4, and when n24, n26 and n27 are each 2 or more, substituents in brackets of 2 or more are the same or different from each other.
The dotted line is the portion connected to chemical formula 1.
In an embodiment of the present specification, R23 to R27 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 6 to 60 carbon atoms.
In an embodiment of the present specification, R23 to R27 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 15 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 6 to 30 carbon atoms.
In an embodiment of the present specification, R23 to R27 are the same or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 6 to 20 carbon atoms.
In one embodiment of the present specification, the above R23 to R27 are the same or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryl group.
In one embodiment of the present specification, R23 to R27 are the same or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted ethyl, substituted or unsubstituted methoxy, or substituted or unsubstituted phenyl.
In one embodiment of the present specification, the above R23 to R27 are the same or different from each other, and each is independently hydrogen, deuterium, ethyl, methoxy, or phenyl.
In one embodiment of the present specification, R23 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryl group.
In one embodiment of the present specification, R23 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
In one embodiment of the present specification, R23 is a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 15 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In one embodiment of the present specification, R23 is a substituted or unsubstituted ethyl group, a substituted or unsubstituted methoxy group, or a substituted or unsubstituted phenyl group.
In one embodiment of the present specification, R23 is ethyl, methoxy or phenyl.
In one embodiment of the present specification, R23 is ethyl or phenyl.
In one embodiment of the present specification, R24 is hydrogen or deuterium.
In one embodiment of the present specification, R24 is hydrogen.
In one embodiment of the present specification, n24 is 0 or 1.
In one embodiment of the present specification, the chemical formula A4-1 is represented by any one of the following structural formulas.
In the above structural formula, a dotted line indicates a portion bonded to the above chemical formula 1.
In one embodiment of the present specification, R25 is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryl group.
In one embodiment of the present specification, R25 is hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
In one embodiment of the present specification, R25 is hydrogen, a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 15 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
In one embodiment of the present specification, R25 is hydrogen, substituted or unsubstituted ethyl, substituted or unsubstituted methoxy, or substituted or unsubstituted phenyl.
In one embodiment of the present specification, R25 is hydrogen, ethyl, methoxy, or phenyl.
In one embodiment of the present specification, R26 is hydrogen or deuterium.
In one embodiment of the present specification, R26 is hydrogen.
In one embodiment of the present specification, n26 is 0 or 1.
In one embodiment of the present specification, the chemical formula A4-2 is represented by any one of the following structural formulas.
In the above structural formula, a dotted line indicates a portion bonded to the above chemical formula 1.
In one embodiment of the present specification, Y1 is O.
In one embodiment of the present specification, Y1 is S.
In one embodiment of the present specification, R27 is hydrogen or deuterium.
In one embodiment of the present specification, R27 is hydrogen.
In one embodiment of the present specification, n27 is 0 or 1.
In one embodiment of the present specification, the above chemical formula A4-3 is represented by any one of the following structural formulas.
In the above structural formula, the dotted line indicates a portion bonded to chemical formula 1.
In an embodiment of the present specification, the above Ar1 and Ar2 are the same or different from each other, each independently is a substituted or unsubstituted monocyclic, bicyclic, tetracyclic or more ring aryl group, or any one of the above formulas A1 and A4.
In an embodiment of the present specification, ar1 and Ar2 described above are the same as or different from each other, each independently is a substituted or unsubstituted monocyclic, bicyclic, tetracyclic or more cyclic aryl group, or any one of the above formulas A1 to A3, A4-1 and A4-3.
In one embodiment of the present specification, ar1 and Ar2 are the same as each other.
In one embodiment of the present specification, ar1 and Ar2 are different from each other.
In an embodiment of the present specification, ar1 is a substituted or unsubstituted monocyclic, bicyclic, tetracyclic or more ring aryl group, and Ar2 is any one of the above chemical formulas A1 to A4.
In one embodiment of the present specification, ar1 and Ar2 mentioned above are the same or different from each other, and each is independently a substituted or unsubstituted monocyclic, bicyclic, tetracyclic or more cyclic aryl group.
In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and each is independently any one of the chemical formulas A1 to A4.
In one embodiment of the present specification, at least one of Ar1 and Ar2 described above is a substituted or unsubstituted monocyclic, bicyclic, tetracyclic or more aromatic group.
In one embodiment of the present specification, at least one of Ar1 and Ar2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted fluoranthenyl group.
In one embodiment of the present specification, at least one of Ar1 and Ar2 is any one of the chemical formulas A1 to A4.
In one embodiment of the present specification, ar1 may be represented by-L11-Ar 11.
In one embodiment of the present specification, ar2 may be represented by-L12-Ar 12.
In one embodiment of the present specification, L11 and L12 are the same or different from each other, and each is independently a direct bond, a phenylene group, or a 2-valent pyridyl group.
In an embodiment of the present specification, the definitions of Ar11 and Ar12 described above may be applied to the definitions of Ar1 and Ar2 described above.
In one embodiment of the present specification, ar1 and Ar2 are selected from the following structural formulas.
In the above structural formula, a dotted line indicates a portion bonded to the above chemical formula 1.
In one embodiment of the present specification, r1 is 0.
In one embodiment of the present specification, r1 is 1.
In one embodiment of the present specification, m is 1.
In one embodiment of the present specification, n is 1.
In one embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 2.
[ Chemical formula 2]
In the above chemical formula 2, ar1 and Ar2 are defined as in chemical formula 1.
In one embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 3.
[ Chemical formula 3]
In the above chemical formula 3, ar11 and Ar12 are defined as the same as Ar1 and Ar2 in the above chemical formula 1.
In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following compounds.
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 compound represented by the above chemical formula 1, 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 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 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, 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 injecting and transporting layer as an organic layer. 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 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 layer, an electron injection and transport layer, or a hole blocking layer, and the electron injection layer, the electron transport layer, the electron injection and transport layer, or the hole blocking layer may include a compound represented by chemical formula 1.
In an embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport 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 may include a 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.
According to one example, the thickness of the organic layer containing the compound of formula 1 isTo the point ofPreferably isTo the point of
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.
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 one embodiment of the present specification, the organic light emitting device includes an anode, a cathode, and 2 or more organic layers disposed between the anode and the cathode, wherein at least one of the 2 or more organic layers includes a compound represented by 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 organic layer of 2 or more layers may be two or more selected from the group consisting of a light-emitting layer, an electron transport layer, an electron injection and transport layer, an electron modulation 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 an embodiment of the present specification, the compound represented by the above chemical formula 1 may be included in 1 layer of the above 2 or more electron transport layers, and may be included in each of the 2 or more electron transport layers.
In addition, in an embodiment of the present specification, when the above compound is included in each of the 2 or more electron transport layers, materials other than the compound represented by the above 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 injecting and transporting layer, the electron injecting layer, or the electron injecting and transporting 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. That is, the electron transport layer, the electron injection layer, or the electron injection and transport 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, and may be contained in each of the 2 or more hole transport layers.
In addition, in one embodiment of the present specification, when the compound represented by the above chemical formula 1 is contained 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 have a reverse structure (inverted type (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
The structure of the organic light emitting device of the present specification may have the structure shown in fig. 1 and 2, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 5, and a cathode 7 are sequentially stacked. In the structure shown above, the above-described compound may be contained in the above-described light-emitting layer 5.
Fig. 2 illustrates a structure 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 injection and transport layer 6, and a cathode 7 are sequentially stacked. In the structure shown above, the above-described compound may be contained in the hole injection layer 3, the hole transport layer 4, the light-emitting layer 5, or the electron injection and transport layer 6.
For example, the organic light emitting device according to the present specification may be manufactured as follows: an anode is formed by vapor deposition of a metal or a metal oxide having conductivity or an alloy thereof on a substrate by PVD (physical vapor deposition: physical vapor deposition) such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation), then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer is formed on the anode, and then a substance usable as a cathode is vapor deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
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 and transport 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. Specific examples of the anode material that can be used in the present invention 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); a combination of metals such as Al or SnO 2 and Sb with oxides; conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ] (PEDOT), polypyrrole and polyaniline, etc., but are 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; a multilayer structure such as LiF/Al or LiO 2/Al, but 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 metalloporphyrin (porphyrine), 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, but are not limited thereto. The thickness of the hole injection layer may be 1 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 movement of holes can be prevented.
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.
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 electron blocking layer may use the above-mentioned compound or a material known in the art.
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. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3); 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, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
When the light-emitting layer emits red light, as a light-emitting dopant, a phosphor such as PIQIr (acac) (bi (1-phenylisoquinoline) acetylacetonateiridium, iridium bis (1-phenylisoquinoline) acetylacetonate), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium, iridium bis (1-phenylquinoline) acetylacetonate), PQIr (tris (1-phenylquinoline) iridium, tris (1-phenylquinoline) iridium), ptOEP (octaethylporphyrin platinum, platinum octaethylporphyrin), or a phosphor such as Alq 3 (tris (8-hydroxyquinolino) aluminum, tris (8-hydroxyquinoline) aluminum) may be used, but is not limited thereto. When the light-emitting layer emits green light, a phosphorescent substance such as Ir (ppy) 3 (fac tris (2-PHENYLPYRIDINE) irium), a fluorescent substance such as Alq 3 (tris (8-hydroxyquinoline) aluminum), or the like can be used as the light-emitting dopant, but is not limited thereto. When the light-emitting layer emits blue light, a phosphorescent material such as (4, 6-F 2ppy)2 Irpic) or a fluorescent material such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), distyrylbenzene (DSB), distyrylarylene (DSA), PFO polymer or PPV polymer may be used as the light-emitting dopant, but is not limited thereto.
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. Specific examples include, but are not limited to, the above-mentioned compounds or Al complexes of 8-hydroxyquinoline, complexes containing Alq 3, organic radical compounds, hydroxyflavone-metal complexes, and the like. The thickness of the electron transport layer may be 1 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 improving the movement of electrons can be prevented when the thickness of the electron transport layer is too thick.
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 the like,Azole (S),Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The 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.
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 being limited to the embodiments described in detail below. Embodiments of the present application are provided to more fully explain the present description to those skilled in the art.
Synthesis example 1 Synthesis of Compound P2
1) Synthesis of Compound P1
After the above compound P-SM (100 g,0.312 mol) was dissolved in 1000ml of acetonitrile under a nitrogen atmosphere, potassium carbonate (129.4 g,0.936 mol) was dissolved in 400ml of water and added thereto, 1,2, 3, 4-nonafluorobutane-1-sulfonyl fluoride (207 g,0.687 mmol) was slowly added dropwise, followed by stirring for 1 hour. The aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure to give the above-mentioned compound P1 (242 g, yield: 91%).
MS[M+H]+＝853
2) Synthesis of Compound P2
P1 (100 g,117.3 mmol) and bis (pinacolato) diboron (59.6 g,234.6 mmol) are added to 2000ml of di under a nitrogen atmosphereIn an alkane (Diox), stirring and refluxing. Then, potassium phosphate (74.7 g,351.9 mmol) was charged, and after stirring thoroughly, bis (dibenzylideneacetone) palladium (2 g,3.5 mmol) and tricyclohexylphosphine (2 g,7 mmol) were charged. After 4 hours of reaction, the reaction mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was dissolved in 634mL of chloroform 10 times again, washed with water 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to yield compound P2 (34.2 g, 54%) as a white solid.
MS[M+H]+＝541
Production example 1: production of Compound E1
P2 (20 g,37 mmol) and E1-A (19.8 g,74 mmol) were added to 400ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (15.3 g,111 mmol) was dissolved in 15ml of water and charged, and after stirring well, tetrakis (triphenylphosphine) palladium (1.3 g,1.1 mmol) was charged. After 1 hour of reaction, the mixture was cooled to room temperature, and the organic layer was separated from the aqueous layer and distilled. This was dissolved in 556mL of chloroform again, washed with water 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, and the mixture was stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to yield compound E1 (14.2 g,51% yield) as a white solid.
MS:[M+H]+＝751
Production example 2: production of Compound E2
The E2 compound was produced by the same method as the production method of production example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H]+＝799
Production example 3: production of Compound E3
The E3 compound was produced by the same method as that of production example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H]+＝597
Production example 4: production of Compound E4
The E4 compound was produced by the same method as the production method of production example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H]+＝541
Production example 5: production of Compound E5
The E5 compound was produced by the same method as that of production example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H]+＝541
Production example 6: production of Compound E6
The E6 compound was produced by the same method as the production method of production example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H]+＝807
Production example 7: production of Compound E7
The E7 compound was produced by the same method as the production method of production example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H]+＝555
Production example 8: production of Compound E8
1) Synthesis of Compound E8-P1
E8-P1-A (10.4 g,37 mmol) was added to 400ml of tetrahydrofuran under nitrogen, stirred and refluxed. Then, potassium carbonate (15.3 g,111 mmol) was dissolved in 15ml of water and charged, and after stirring well, tetrakis (triphenylphosphine) palladium (1.3 g,1.1 mmol) was charged. P2 (10 g,18.5 mmol) was added dropwise, and after reacting for 1 hour, the organic layer was separated from the aqueous layer after cooling to room temperature, and the organic layer was distilled. This was dissolved in 488mL of chloroform 20 times again, washed with water 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, and after stirring, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare white solid compound E8-P1 (12.2 g,50% yield).
MS:[M+H]+＝555
2) Synthesis of Compound E8
The E8 compound was produced by the same method as the synthesis of the compound E8-P1, except that each starting material was used as in the above reaction formula.
MS:[M+H]+＝685
Production example 9: production of Compound E9
The E9 compound was produced by the same method as that of production example 8, except that each starting material was used as in the above reaction formula.
MS:[M+H]+＝740
Production example 10: production of Compound E10
The E10 compound was produced by the same method as the production method of production example 8, except that each starting material was used as in the above reaction formula.
MS:[M+H]+＝646
Production example 11: production of Compound E11
The E11 compound was produced by the same method as that of production example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H]+＝523
Production example 12: production of Compound E12
The E12 compound was produced by the same method as the production method of production example 1, except that each starting material was used as in the above reaction formula.
MS:[M+H]+＝577
Production example 13: production of Compound E13
The E13 compound was produced by the same method as that of production example 8, except that each starting material was used as in the above reaction formula.
MS:[M+H]+＝658
Example 1-1
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 he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode thus prepared, the following compound [ HI-A ] was usedAnd performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, hexanitrile hexaazabenzophenanthrene (hexaazatriphenylene, HAT) of the following chemical formulaAnd the following compound [ HT-A ]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-deposited at a weight ratio of 25:1 to form a light-emitting layer.
On the light-emitting layer, the compound E1 produced according to production example 1 and the following compound [ LiQ ] (lithium quinolinolato) were vacuum-evaporated at a weight ratio of 1:1 to give a light-emitting layerForm an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added toTo the thickness of aluminumAnd 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 cathodeIs maintained by aluminumDuring vapor deposition, the vacuum degree was maintained at 1×10 -7～5×10-8 torr, thereby producing an organic light-emitting device.
Examples 1-2 to 1-13
An organic light emitting device was manufactured in the same manner as in example 1-1 except that the compound of the following table 1 was used instead of the compound E1 in example 1-1 described above.
Comparative examples 1-1 to 1-16
An organic light emitting device was manufactured in the same manner as in example 1-1 except that the compound of the following table 1 was used instead of the compound E1 in example 1-1 described above.
The organic light-emitting device was measured for driving voltage and light-emitting efficiency at a current density of 10mA/cm 2, and for a time of 90% relative to the initial luminance at a current density of 20mA/cm 2 (T 90). The results are shown in table 1 below.
TABLE 1
TABLE 1
As shown in the above table 1, the compound represented by chemical formula 1 according to the present invention may be used in an electron injection and transport layer of an organic light emitting device.
According to the chemical formula 1 of the present invention, since the adamantyl group between the phenyl groups improves the thermal stability of the molecule, and the aryl group or the heterocyclic group represented by the chemical formulas A1 to A4 is included as the substituent (Ar 1, ar 2), the electron injection and transport are smooth, and thus the result of improving the voltage, efficiency and/or lifetime characteristics in the organic light emitting device is shown.
Therefore, the above examples 1-11 to 1-13 were confirmed to exhibit excellent voltage, efficiency and life characteristics as compared with comparative examples 1-1 to 1-10 containing no adamantyl group and comparative examples 1-11 to 1-16 containing no substituent of chemical formula 1.

Claims (11)

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,
R1 is hydrogen or deuterium, and the hydrogen is hydrogen,
Ar1 and Ar2 are the same as or different from each other, and each is independently a phenyl group substituted or unsubstituted with a nitrile group or a benzimidazolyl group substituted with an ethyl group, a biphenyl group substituted or unsubstituted with a nitrile group, or a fluoranthenyl group, or any one of the following chemical formulas A1, A3 and A4,
Chemical formula A1
Chemical formula A3
Chemical formula A4
In the chemical formulas A1, A3 and A4,
X1 is N or CR11, X2 is N or CR12, X3 is N or CR13, X4 is N or CR14, X5 is N or CR15,
At least one of X1 to X5 is N,
Y is O, S or NR23, and the like,
R11 to R15 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a methyl group, a phenyl group substituted or unsubstituted with a methyl group, a biphenyl group, a naphthyl group, a pyridyl group substituted or unsubstituted with a methyl group, or a benzimidazolyl group substituted or unsubstituted with an ethyl group,
R22 is hydrogen, deuterium, phenyl, naphthyl or furyl,
One of R23, G1 and G2 is connected with chemical formula 1, and the others are the same or different from each other, each is independently hydrogen, deuterium, ethyl, methoxy, or phenyl,
R1 is an integer of 0 to 14,
M and n are each an integer of 1 to 5,
N22 is an integer of 0 to 5,
G2 is an integer of 0 to 4,
When r1, m, n22 and g2 are each 2 or more, the substituents in parentheses of 2 or more are the same or different from each other,
The dotted line is the portion connected to chemical formula 1.
2. The compound of claim 1, wherein the chemical formula 1 is represented by the following chemical formula 2:
chemical formula 2
In the chemical formula 2, ar1 and Ar2 are defined as in chemical formula 1.
3. The compound of claim 1, wherein the formula A4 is represented by any one of the following formulas A4-1 to A4-3:
formula A4-1
Formula A4-2
Formula A4-3
In the chemical formulas A4-1 to A4-3,
Y1 is O or S, and the total number of the components is equal to or less than zero,
R23 to R27 are the same or different from each other and are each independently hydrogen, deuterium, ethyl, methoxy, or phenyl,
N24, n26 and n27 are integers of 0 to 4, and when n24, n26 and n27 are each 2 or more, substituents in brackets of 2 or more are the same or different from each other,
The dotted line is the portion connected to chemical formula 1.
4. The compound of claim 1, wherein at least one of Ar1 and Ar2 is any one of the formulas A1, A3, and A4.
5. The compound of claim 1, wherein the chemical formula 1 is represented by any one of the following compounds:
6. an organic light emitting device comprising:
An anode;
A cathode; and
More than 1 organic layer arranged between the anode and the cathode,
Wherein 1 or more of the organic layers comprises the compound according to any one of claims 1 to 5.
7. The organic light-emitting device of claim 6, wherein the organic layer comprises an electron injection layer, an electron transport layer, or an electron injection and transport layer, the electron injection layer, electron transport layer, or electron injection and transport layer comprising the compound.
8. The organic light emitting device of claim 7, wherein the electron injection layer, electron transport layer, or electron injection and transport layer further comprises an n-type dopant or an organometallic compound.
9. The organic light emitting device of claim 8, wherein the n-type dopant or organometallic compound is LiQ.
10. An organic light-emitting device according to claim 6 wherein the organic layer comprises a hole blocking layer comprising the compound.
11. The organic light-emitting device according to claim 6, wherein the organic layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, the hole injection layer, the hole transport layer, or the hole injection and transport layer containing the compound.
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