CN110785406A - Compound and organic light emitting device including the same - Google Patents
Compound and organic light emitting device including the same Download PDFInfo
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- CN110785406A CN110785406A CN201880041595.1A CN201880041595A CN110785406A CN 110785406 A CN110785406 A CN 110785406A CN 201880041595 A CN201880041595 A CN 201880041595A CN 110785406 A CN110785406 A CN 110785406A
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- C07D209/56—Ring systems containing three or more rings
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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Abstract
The present specification relates to a compound of chemical formula 1 and an organic light emitting device including the same.
Description
Technical Field
The present application claims priority to korean patent application No. 10-2017-0160620, filed on 28.11.2017 and korean patent application No. 10-2018-0147707, filed on 26.11.2018, all of which are incorporated herein by reference.
The present specification relates to a compound and an organic light emitting device including the same.
Background
For commercialization of organic light emitting devices, it is required to improve the efficiency of light emitting materials, and for this reason, research into phosphorescent and delayed fluorescent materials is being actively conducted. However, the phosphorescent material has a problem that a metal complex required for realizing phosphorescence is expensive and has a short lifetime, although high efficiency can be achieved.
In The case of Delayed Fluorescence materials, The concept of Thermally Activated Delayed Fluorescence (TADF) has recently been introduced, and a high-efficiency green fluorescent material which is both a fluorescent material and has high external quantum efficiency has been published. The concept of thermally activated delayed fluorescence refers to a phenomenon in which fluorescence emission is achieved by reverse energy transfer from an excited triplet state to an excited singlet state due to thermal activation, and is called delayed fluorescence in that light emission having a long lifetime is generally generated by light emission through a triplet state pathway. Since both of the fluorescent emission and the phosphorescent emission can be used as the delayed fluorescent material, the problem of external quantum efficiency of the conventional fluorescent material can be solved, and the problem of the price of the phosphorescent material can be solved since the fluorescent material may not contain a metal complex.
Disclosure of Invention
Technical subject
The present specification provides compounds and organic light emitting devices comprising the same.
Means for solving the problems
According to one embodiment of the present specification, there is provided a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the chemical formula 1 described above,
a1 to a5, equal to or different from each other, are each independently hydrogen; a halogen group; a cyano group; a haloalkyl group; an alkyl group; an alkenyl group; a haloalkoxy group; aryl substituted or unsubstituted with a halogen group, cyano, haloalkyl, alkyl, or haloalkoxy; or a heteroaryl group, or adjacent groups are bonded to each other to form an aromatic ring,
r1 to R8 and R11 to R18, which are the same or different from each other, are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amide group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryloxy group; substituted or unsubstituted alkylthio (
Alkyl thio xy); substituted or unsubstituted arylthio(s) ((s))
Aryl thio), alkyl (Aryl thio) and (C) alkyl (Aryl thio) alkylSubstituted or unsubstituted alkylsulfonyl (
Alkyl sulfoxy), substituted or unsubstituted arylsulfonyl(s) ((s)
Aryl sulfoxy), a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylphosphyl group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted Aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring,
n is 1 or 2, and n is a hydrogen atom,
when n is 2, the structures in parentheses are the same or different from each other,
when n is 1 and any one of the above-mentioned A1 to A5 is heteroaryl, the remainder are hydrogen.
In addition, according to an embodiment of the present specification, there is provided an organic light emitting device including: the organic light-emitting device includes a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include the compound.
Effects of the invention
The organic light emitting device including the compound represented by chemical formula 1 according to an embodiment of the present specification can achieve an improvement in efficiency, a low driving voltage, and/or an improvement in lifetime characteristics.
Drawings
Fig. 1 illustrates an organic light emitting device according to an embodiment of the present specification.
< description of symbols >
10: organic light emitting device
20: substrate
30: a first electrode
40: luminescent layer
50: second electrode
Detailed Description
The present specification will be described in more detail below.
According to an embodiment of the present specification, there is provided a compound represented by the above chemical formula 1.
The compound represented by chemical formula 1 according to one embodiment of the present specification is bonded with 2 cyano groups at a para position (para) with a benzene nucleus as a center, and thus emits light in a specific wavelength region, and an organic light emitting device including the same has high efficiency characteristics.
In addition, 2 carbazole derivatives and 1 or 2 aryl groups are combined centering on the benzene nucleus of chemical formula 1 of the present application, so that the charge balance injected into the light emitting layer is adjusted, and the organic light emitting device including the same can achieve low driving voltage, efficiency, and lifetime improvement.
In the present specification, when a part is referred to as "including" a certain component, unless specifically stated to the contrary, it means that the other component may be further included, and the other component is not excluded.
In the present specification, examples of the substituent are described below, but the substituent is not limited thereto.
The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the substituted position is not limited as long as the hydrogen atom can be substituted, that is, the substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same as or different from each other.
The term "substituted or unsubstituted" in the present specification means substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, a cyano group, a nitro group, an imide group, an amide group, a carbonyl group, an ester group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylphosphine group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, or a substituent formed by connecting 2 or more substituents among the above-exemplified substituents, or do not have any substituents. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.
In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30. Specifically, the compound may have the structure shown below, but is not limited thereto.
In the amide group, the nitrogen of the amide group may be replaced by hydrogen; a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms; or aryl having 6 to 30 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 30. Specifically, the compound may have the structure shown below, but is not limited thereto.
In the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, and is preferably 1 to 30. Specific examples thereof include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methylbutyl group, 1-ethylbutyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2-dimethylheptyl group, 1-ethylpropyl group, 1-dimethylpropyl group, isohexyl group, 2-methylpentyl group, 2, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 30 carbon atoms, specifically, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a2, 3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a2, 3-dimethylcyclohexyl group, a3, 4, 5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but is not limited thereto.
In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but the number of carbon atoms is preferably 1 to 30. Specifically, it may be 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-decoxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited thereto.
In the present specification, the amine group may be selected from-NH
2An alkylamino group,The number of carbon atoms of the N-alkylarylamino, arylamino, N-arylheteroarylamino, N-alkylheteroarylamino and heteroarylamino group is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include, but are not limited to, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, an anthrylamino group, a 9-methylanthrylamino group, a diphenylamino group, an N-phenylnaphthylamino group, a ditolylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-phenylbiphenylamino group, an N-phenylnaphthylamino group, an N-biphenylnaphthylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrylamino group, an N-phenylfluorenylamino group, an N-phenylterphenylamino group, an N-phenanthrenylfluorenylamino group, and an N-biphenylfluorenylamino group.
In the present specification, an N-alkylarylamino group means an amino group in which an alkyl group and an aryl group are substituted on N of the amino group.
In the present specification, N-arylheteroarylamino represents an amino group in which an aryl group and a heteroaryl group are substituted on N of the amino group.
In the present specification, an N-alkylheteroarylamino group means an amino group in which an alkyl group and a heteroaryl group are substituted on N of the amino group.
In the present specification, the alkyl group in the alkylamino group, N-arylalkylamino group, alkylthio group, alkylsulfonyl group, and N-alkylheteroarylamino group is the same as that exemplified above for the alkyl group. Specifically, examples of the alkylthio group include methylthio, ethylthio, tert-butylthio, hexylthio, octylthio, and the like; examples of the alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, and a butylsulfonyl group, but are not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, styryl and the like.
In the present specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In this specification, the boron group may be-BR
100R
101R is as defined above
100And R
101The same or different, may be each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted monocyclic or polycyclic cycloalkyl group of carbon number 3 to 30, substituted or unsubstituted linear or branched alkyl group of carbon number 1 to 30, substituted or unsubstituted monocyclic or polycyclic aryl group of carbon number 6 to 30, and substituted or unsubstituted monocyclic or polycyclic heteroaryl group of carbon number 2 to 30.
In the present specification, specific examples of the phosphine oxide group include a diphenylphosphine oxide group, a dinaphthylphosphine oxide group and the like, but the phosphine oxide group is not limited thereto.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.
When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30. Specifically, the polycyclic aryl group may be a naphthyl group, an anthryl group, a phenanthryl group, a triphenyl group, a pyrenyl group, a phenalenyl group, a perylenyl group, a perylene group,
examples of the group include a fluorenyl group and a fluoranthenyl group.
In the present specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.
In the case where the above-mentioned fluorenyl group is substituted, it may be
And the like, but is not limited thereto.
In the present specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to an atom substituted with the substituent, a substituent sterically closest to the substituent, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted at the ortho (ortho) position in the phenyl ring and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as groups "adjacent" to each other.
In the present specification, the aryl group in the aryloxy group, the arylthio group, the arylsulfonyl group, the N-arylalkylamino group, the N-arylheteroarylamino group, and the arylphosphoryl group is exemplified by the same aryl group as described above. Specifically, the aryloxy group includes, but is not limited to, phenoxy, p-tolyloxy, m-tolyloxy, 3, 5-dimethylphenoxy, 2,4, 6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthracenyloxy, 2-anthracenyloxy, 9-anthracenyloxy, 1-phenanthrenyloxy, 3-phenanthrenyloxy, 9-phenanthrenyloxy, and the like, and the arylthio group includes phenylthio, 2-methylphenylthio, 4-tert-butylphenylthio, and the like, and the arylsulfonyl group includes benzenesulfonyl, p-toluenesulfonyl, and the like.
In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group and a substituted or unsubstituted diarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing 2 or more of the above-mentioned aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or may contain both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group can be selected from the examples of the aryl group described above.
In the present specification, the heteroaryl group contains 1 or more heteroatoms other than carbon atoms, specifically, the heteroatoms may contain 1 or more atoms selected from O, N, Se, S and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Azolyl group,
Oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, phenyl
In the present specification, as examples of the heteroarylamino group, there may be mentioned a substituted or unsubstituted monoheteroarylamino group, or a substituted or unsubstituted diheteroarylamino group. Heteroarylamine groups comprising more than 2 of the above-described heteroaryls may comprise a monocyclic heteroaryl, a polycyclic heteroaryl, or may comprise both a monocyclic heteroaryl and a polycyclic heteroaryl. For example, the heteroaryl group in the heteroarylamino group can be selected from the examples of the heteroaryl group described above.
In this specification, examples of the heteroaryl group in the N-arylheteroarylamino group and the N-alkylheteroarylamino group are the same as those of the heteroaryl group described above.
In the present specification, a substituted or unsubstituted ring formed by bonding adjacent groups to each other, and a "ring" refers to a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.
In the specification, the hydrocarbon ring may be aromatic, aliphatic, or a fused ring of aromatic and aliphatic, and may be selected from the cycloalkyl groups and the aryl groups described above, in addition to the above being not 1-valent.
In the present specification, the aromatic ring may be a monocyclic ring or a polycyclic ring, and may be selected from the above-mentioned examples of aryl groups except for having a valence of 1.
In the present specification, the heterocyclic ring contains 1 or more heteroatoms other than carbon atoms, specifically, the heteroatoms may contain 1 or more atoms selected from O, N, Se, S and the like. The heterocyclic ring may be monocyclic or polycyclic, may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from the heteroaryl groups and heterocyclic groups described above except for having a valence of 1.
According to an embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 1-1 or 1-2.
[ chemical formula 1-1]
[ chemical formulas 1-2]
In the above chemical formulas 1-1 and 1-2,
a1 to A5, R1 to R8 and R11 to R18 are as defined above in chemical formula 1,
a11 to a15, equal to or different from each other, are each independently hydrogen; a halogen group; a cyano group; a haloalkyl group; an alkyl group; an alkenyl group; a haloalkoxy group; aryl substituted or unsubstituted with a halogen group, cyano, haloalkyl, alkyl, or haloalkoxy; or a heteroaryl group, or adjacent groups are bonded to each other to form an aromatic ring.
According to an embodiment of the present disclosure, in the chemical formula 1, R1 to R8 and R11 to R18 are the same or different from each other, and each is independently hydrogen or a substituted or unsubstituted alkyl group.
According to an embodiment of the present disclosure, in the chemical formula 1, R1 to R8 and R11 to R18 are the same or different from each other, and each is independently hydrogen or an alkyl group.
According to an embodiment of the present disclosure, in the chemical formula 1, R1 to R8 and R11 to R18 are the same or different from each other, and each is independently hydrogen or methyl.
According to an embodiment of the present disclosure, in the above chemical formula 1, adjacent groups among R1 to R8 and R11 to R18 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.
According to an embodiment of the present disclosure, in the chemical formula 1, adjacent groups among R1 to R8 and R11 to R18 are bonded to each other to form a hydrocarbon ring substituted with 1 or more alkyl groups.
According to one embodiment of the present disclosure, in chemical formula 1, adjacent groups among R1 to R8 and R11 to R18 are bonded to each other to form an aromatic ring substituted with 1 or more alkyl groups.
According to an embodiment of the present disclosure, in the chemical formula 1, adjacent groups among R1 to R8 and R11 to R18 are combined with each other to form an indene ring substituted with 1 or more alkyl groups.
According to an embodiment of the present disclosure, in the chemical formula 1, adjacent groups among R1 to R8 and R11 to R18 are combined with each other to form an indene ring substituted with 1 or more methyl groups.
According to an embodiment of the present disclosure, in the chemical formula 1, R2 and R3 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.
According to an embodiment of the present disclosure, in chemical formula 1, R2 and R3 are combined with each other to form a hydrocarbon ring substituted with 1 or more alkyl groups.
According to one embodiment of the present disclosure, in chemical formula 1, R2 and R3 are bonded to each other to form an aromatic ring substituted with 1 or more alkyl groups.
According to an embodiment of the present disclosure, in chemical formula 1, R2 and R3 combine with each other to form an indene ring substituted with 1 or more alkyl groups.
According to an embodiment of the present disclosure, R2 and R3 combine with each other to form an indene ring substituted with 1 or more methyl groups in chemical formula 1.
According to an embodiment of the present disclosure, in the chemical formula 1, any one of R2 and R3 is a substituted or unsubstituted aryl group, and the rest is a substituted or unsubstituted alkyl group, and R2 and R3 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.
According to an embodiment of the present disclosure, in the chemical formula 1, any one of R2 and R3 is a substituted or unsubstituted phenyl group, and the rest is a substituted or unsubstituted alkyl group, and R2 and R3 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.
According to an embodiment of the present disclosure, in the chemical formula 1, R3 is a substituted or unsubstituted phenyl group, R2 is a substituted or unsubstituted alkyl group, and R2 and R3 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.
According to an embodiment of the present disclosure, in chemical formula 1, R3 is a phenyl group, R2 is an isopropyl group, and R2 and R3 are combined with each other to form an indene ring substituted with 2 methyl groups.
According to an embodiment of the present disclosure, in the chemical formula 1, R6 and R7 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.
According to an embodiment of the present disclosure, in chemical formula 1, R6 and R7 are combined with each other to form a hydrocarbon ring substituted with 1 or more alkyl groups.
According to one embodiment of the present disclosure, in chemical formula 1, R6 and R7 are bonded to each other to form an aromatic ring substituted with 1 or more alkyl groups.
According to an embodiment of the present disclosure, in chemical formula 1, R6 and R7 combine with each other to form an indene ring substituted with 1 or more alkyl groups.
According to one embodiment of the present disclosure, in chemical formula 1, R6 and R7 combine with each other to form an indene ring substituted with 1 or more methyl groups.
According to an embodiment of the present disclosure, in the chemical formula 1, any one of R6 and R7 is a substituted or unsubstituted aryl group, and the rest is a substituted or unsubstituted alkyl group, and R6 and R7 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.
According to an embodiment of the present disclosure, in the chemical formula 1, any one of R6 and R7 is a substituted or unsubstituted phenyl group, and the rest is a substituted or unsubstituted alkyl group, and R6 and R7 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.
According to an embodiment of the present disclosure, in the chemical formula 1, R6 is a substituted or unsubstituted phenyl group, R7 is a substituted or unsubstituted alkyl group, and R6 and R7 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.
According to an embodiment of the present disclosure, in chemical formula 1, R6 is a phenyl group, R7 is an isopropyl group, and R6 and R7 are combined with each other to form an indene ring substituted with 2 methyl groups.
According to an embodiment of the present disclosure, in the chemical formula 1, R12 and R13 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.
According to an embodiment of the present disclosure, in chemical formula 1, R12 and R13 are combined with each other to form a hydrocarbon ring substituted with 1 or more alkyl groups.
According to one embodiment of the present disclosure, in chemical formula 1, R12 and R13 are bonded to each other to form an aromatic ring substituted with 1 or more alkyl groups.
According to one embodiment of the present disclosure, in chemical formula 1, R12 and R13 combine with each other to form an indene ring substituted with 1 or more alkyl groups.
According to one embodiment of the present disclosure, in chemical formula 1, R12 and R13 combine with each other to form an indene ring substituted with 1 or more methyl groups.
According to an embodiment of the present disclosure, in the chemical formula 1, any one of R12 and R13 is a substituted or unsubstituted aryl group, and the rest is a substituted or unsubstituted alkyl group, and R12 and R13 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.
According to an embodiment of the present disclosure, in the chemical formula 1, any one of R12 and R13 is a substituted or unsubstituted phenyl group, and the rest is a substituted or unsubstituted alkyl group, and R12 and R13 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.
According to an embodiment of the present disclosure, in the chemical formula 1, R13 is a substituted or unsubstituted phenyl group, R12 is a substituted or unsubstituted alkyl group, and R12 and R13 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.
According to an embodiment of the present disclosure, in chemical formula 1, R13 is a phenyl group, R12 is an isopropyl group, and R12 and R13 are combined with each other to form an indene ring substituted with 2 methyl groups.
According to an embodiment of the present disclosure, in the chemical formula 1, R16 and R17 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.
According to an embodiment of the present disclosure, in chemical formula 1, R16 and R17 are combined with each other to form a hydrocarbon ring substituted with 1 or more alkyl groups.
According to one embodiment of the present disclosure, in chemical formula 1, R16 and R17 are bonded to each other to form an aromatic ring substituted with 1 or more alkyl groups.
According to an embodiment of the present disclosure, in chemical formula 1, R16 and R17 combine with each other to form an indene ring substituted with 1 or more alkyl groups.
According to one embodiment of the present disclosure, in chemical formula 1, R16 and R17 combine with each other to form an indene ring substituted with 1 or more methyl groups.
According to an embodiment of the present disclosure, in the chemical formula 1, any one of R16 and R17 is a substituted or unsubstituted aryl group, and the rest is a substituted or unsubstituted alkyl group, and R16 and R17 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.
According to an embodiment of the present disclosure, in the chemical formula 1, any one of R16 and R17 is a substituted or unsubstituted phenyl group, and the rest is a substituted or unsubstituted alkyl group, and R16 and R17 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.
According to an embodiment of the present disclosure, in the chemical formula 1, R16 is a substituted or unsubstituted phenyl group, R17 is a substituted or unsubstituted alkyl group, and R16 and R17 are combined with each other to form a substituted or unsubstituted hydrocarbon ring.
According to an embodiment of the present disclosure, in chemical formula 1, R16 is a phenyl group, R17 is an isopropyl group, and R16 and R17 are combined with each other to form an indene ring substituted with 2 methyl groups.
According to an embodiment of the present description, a1 to a5 and a11 to a15, equal to or different from each other, are each independently hydrogen; a halogen group; a cyano group; a haloalkyl group; an alkyl group; an alkenyl group; a haloalkoxy group; aryl substituted or unsubstituted with a halogen group, cyano, haloalkyl, alkyl, or haloalkoxy; or a heteroaryl group.
According to an embodiment of the present description, a1 to a5 and a11 to a15, equal to or different from each other, are each independently hydrogen; fluorine; a cyano group; a trifluoromethyl group; a methyl group; isopropyl group; a tertiary butyl group; a trifluoromethoxy group; aryl substituted or unsubstituted with fluoro, cyano, trifluoromethyl, methyl, or trifluoromethoxy; or a polycyclic heteroaryl group.
According to an embodiment of the present description, a1 to a5 and a11 to a15, equal to or different from each other, are each independently hydrogen; fluorine; a cyano group; a trifluoromethyl group; a methyl group; isopropyl group; a tertiary butyl group; a trifluoromethoxy group; phenyl unsubstituted or substituted by fluoro, cyano, trifluoromethyl, methyl, or trifluoromethoxy; or a carbazolyl group.
According to an embodiment of the present specification, adjacent groups of a1 to a5 are bonded to each other to form an aromatic ring.
According to an embodiment of the present specification, adjacent groups of a1 to a5 are bonded to each other to form a benzene ring.
According to an embodiment of the present specification, adjacent groups of a11 to a15 are bonded to each other to form an aromatic ring.
According to an embodiment of the present specification, adjacent groups of a11 to a15 are bonded to each other to form a benzene ring.
According to an embodiment of the present description, a1 and a5 combine with each other to form an aromatic ring.
According to an embodiment of the present specification, a1 and a5 combine with each other to form a benzene ring.
According to an embodiment of the present specification, a1 and a5 are each a substituted or unsubstituted alkenyl group, which combine with each other to form a substituted or unsubstituted benzene ring.
According to one embodiment of the present disclosure, a1 and a5 are vinyl groups (ethenyl groups), respectively, which combine with each other to form a benzene ring.
According to an embodiment of the present description, a2 and A3 combine with each other to form an aromatic ring.
According to an embodiment of the present specification, a2 and A3 combine with each other to form a benzene ring.
According to an embodiment of the present specification, a2 and A3 are each a substituted or unsubstituted alkenyl group, which combine with each other to form a substituted or unsubstituted benzene ring.
According to one embodiment of the present specification, a2 and A3 are each a vinyl group, and are bonded to each other to form a benzene ring.
According to an embodiment of the present description, A3 and a4 combine with each other to form an aromatic ring.
According to an embodiment of the present specification, A3 and a4 combine with each other to form a benzene ring.
According to an embodiment of the present specification, A3 and a4 are each a substituted or unsubstituted alkenyl group, which combine with each other to form a substituted or unsubstituted benzene ring.
According to one embodiment of the present specification, A3 and a4 are each a vinyl group, and are bonded to each other to form a benzene ring.
According to an embodiment of the present description, a4 and a5 combine with each other to form an aromatic ring.
According to an embodiment of the present specification, a4 and a5 combine with each other to form a benzene ring.
According to an embodiment of the present specification, a4 and a5 are each a substituted or unsubstituted alkenyl group, which combine with each other to form a substituted or unsubstituted benzene ring.
According to one embodiment of the present specification, a4 and a5 are each a vinyl group, and are bonded to each other to form a benzene ring.
According to an embodiment of the present description, a11 and a12 combine with each other to form an aromatic ring.
According to an embodiment of the present specification, a11 and a12 combine with each other to form a benzene ring.
According to an embodiment of the present specification, a11 and a12 are each a substituted or unsubstituted alkenyl group, which combine with each other to form a substituted or unsubstituted benzene ring.
According to one embodiment of the present specification, a11 and a12 are each a vinyl group, and are bonded to each other to form a benzene ring.
According to an embodiment of the present description, a12 and a13 combine with each other to form an aromatic ring.
According to an embodiment of the present specification, a12 and a13 combine with each other to form a benzene ring.
According to an embodiment of the present specification, a12 and a13 are each a substituted or unsubstituted alkenyl group, which combine with each other to form a substituted or unsubstituted benzene ring.
According to one embodiment of the present specification, a12 and a13 are each a vinyl group, and are bonded to each other to form a benzene ring.
According to an embodiment of the present description, a13 and a14 combine with each other to form an aromatic ring.
According to an embodiment of the present specification, a13 and a14 combine with each other to form a benzene ring.
According to an embodiment of the present specification, a13 and a14 are each a substituted or unsubstituted alkenyl group, which combine with each other to form a substituted or unsubstituted benzene ring.
According to one embodiment of the present specification, a13 and a14 are each a vinyl group, and are bonded to each other to form a benzene ring.
According to an embodiment of the present description, a14 and a15 combine with each other to form an aromatic ring.
According to an embodiment of the present specification, a14 and a15 combine with each other to form a benzene ring.
According to an embodiment of the present specification, a14 and a15 are each a substituted or unsubstituted alkenyl group, which combine with each other to form a substituted or unsubstituted benzene ring.
According to one embodiment of the present specification, a14 and a15 are each a vinyl group, and are bonded to each other to form a benzene ring.
According to an embodiment of the present disclosure, in the chemical formula 1, when n is 1 and any one of a1 to a5 is a polycyclic heteroaryl group, the rest is hydrogen.
According to an embodiment of the present disclosure, in chemical formula 1, when n is 1 and any one of a1 to a5 is a carbazolyl group, the remainder is hydrogen.
According to an embodiment of the present disclosure, the chemical formula 1 is selected from the following compounds.
According to an embodiment of the present specification, the compound represented by the above chemical formula 1 is a delayed fluorescence compound.
In a general organic light emitting device, the number of excitons generated in the singlet state and the triplet state is set to 25: the ratio of 75 (singlet: triplet) is generated, and the ratio can be classified into fluorescence emission, phosphorescence emission, and thermally activated delayed fluorescence emission according to the emission form in which excitons move. The phosphorescence refers to the transition of excitons in a triplet excited state to a ground state (ground state) to emit light, the fluorescence refers to the transition of excitons in a singlet excited state to a ground state to emit light, and the thermally activated delayed fluorescence refers to the transition of excitons in a singlet excited state to a ground state induced by the induction of reverse intersystem crossing from the triplet excited state to the singlet excited state to cause fluorescence.
The above-mentioned thermally activated delayed fluorescence emission is distinguished from fluorescence emission in that the peak position of the emission spectrum is the same as fluorescence but the decay time (decay) is long, and S is present in the peak position of the emission spectrum in comparison with phosphorescence spectrum in the case that the decay time is long
1-T
1The difference in energy is distinguished from phosphorescence. At this time, S
1At singlet (singlets) energy level, T
1Is the triplet (triplet) energy level.
According to an embodiment of the present specification, there is provided an organic light emitting device including: the organic light-emitting device includes a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include the compound.
According to one embodiment of the present description, the organic layer of the organic light-emitting device of the present description may be formed of a single layer structure, or may be formed of a multilayer structure in which two or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and may include fewer or more organic layers.
For example, the structure of the organic light emitting device of the present specification may have a structure as shown in fig. 1, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. Fig. 1 illustrates an exemplary structure of an organic light emitting device according to an embodiment of the present disclosure, and may further include another organic layer.
According to one embodiment of the present disclosure, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.
According to one embodiment of the present disclosure, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound as a dopant of the light-emitting layer.
According to an embodiment of the present disclosure, the maximum light emission wavelength of the dopant is 480nm to 570 nm.
According to an embodiment of the present disclosure, the dopant is a green dopant.
According to one embodiment of the present specification, the light-emitting substance of the light-emitting layer 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 the light-emitting layer may contain the compound as a dopant of the light-emitting layer, and may contain, as a host, an organic compound having a higher value of at least one of excited singlet energy and excited triplet energy than a light-emitting material of the compound, a hole-transporting ability and an electron-transporting ability, and having a high glass transition temperature to prevent a wavelength of light emission.
According to one embodiment of the present disclosure, the organic layer includes a light-emitting layer, and the light-emitting layer includes a host.
According to one embodiment of the present disclosure, the organic layer includes a light-emitting layer, and the light-emitting layer includes at least one selected from an aromatic fused ring derivative and a heterocyclic ring-containing compound as a main component of the light-emitting layer.
According to one embodiment of the present specification, the aromatic fused ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, and a pentacene derivativeExamples of the heterocyclic ring-containing compound include carbazole derivatives, dibenzofuran derivatives and ladder-type furan compounds
Pyrimidine derivatives, etc., but are not limited thereto.
According to an embodiment of the present disclosure, the main body may include any one or more selected from the following compounds, but is not limited thereto.
According to one embodiment of the present disclosure, the organic layer includes a light emitting layer, the light emitting layer includes a compound represented by the chemical formula 1 as a dopant of the light emitting layer, and the light emitting layer includes a host including at least one selected from the group consisting of an aromatic fused ring derivative and a heterocyclic ring-containing compound as a light emitting layer.
According to one embodiment of the present disclosure, the light emitting layer includes the dopant and the host at a weight ratio of 1:99 to 50: 50.
According to one embodiment of the present disclosure, the organic layer includes a light emitting layer including a dopant including a compound represented by the chemical formula 1 and a host including at least one selected from the aromatic fused ring derivative and the heterocyclic ring-containing compound at a weight ratio of 1:99 to 50: 50.
The organic light emitting device of the present specification may be manufactured by a material and a method known in the art, except that the compound of the present specification, that is, the compound represented by the above chemical formula 1, is included as a dopant of the light emitting layer.
When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
For example, the organic light emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be produced as follows: the organic el device is manufactured by forming a first electrode by depositing metal, a conductive metal oxide, or an alloy thereof on a substrate by a Physical Vapor Deposition (PVD) method such as a sputtering method or an electron beam evaporation method, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the first electrode, and then depositing a substance that can be used as a second electrode on the organic layer. In addition to this method, the second electrode material, the organic layer, and the first electrode material may be sequentially deposited on the substrate to manufacture the organic light-emitting device. In addition, the heterocyclic compound represented by the above chemical formula 1 may form an organic layer not only by a vacuum evaporation method but also by a solution coating method in manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
According to an embodiment of the present disclosure, the first electrode is an anode, and the second electrode is a cathode.
In another embodiment of the present disclosure, the first electrode is a cathode, and the second electrode is an anode.
The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; zinc oxide, Indium Tin Oxide (ITO), indium tin oxideMetal oxides such as Indium Zinc (IZO); ZnO: al or SnO
2: a combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO
2Multilayer structure materials such as/Al, Mg/Ag, etc., but not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: the organic light-emitting device has the ability to transport holes, has a hole injection effect from the anode, has an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and has excellent thin film formation ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is a material that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and is preferably a material having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
The electron transport layer receives electrons from the electron injection layer and transports the electrons to the light emitting layerThe layer of the layer is a substance capable of receiving electrons from the cathode and transferring the electrons to the light-emitting layer as an electron-transporting substance, and is preferably a substance having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq
3Organic radical compounds, hydroxyl brass-metal complexes, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode substances are, in particular, the customary substances having a low work function and accompanied by an aluminum or silver layer, in particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum or silver layer.
The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound of: has an ability to transport electrons, an electron injection effect from a cathode, an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and is excellent in thin-film formability. Specifically, there are fluorenone, anthraquinone dimethane (Anthraquinodimethane), diphenoquinone, thiopyran dioxide, and,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.
The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
Modes for carrying out the invention
Hereinafter, examples will be described in detail to specifically describe the present specification. However, the embodiments described herein may be modified into various forms, and the scope of the present description is not to be construed as being limited to the embodiments described in detail below. The embodiments of the present description are provided to more fully describe the present description to those skilled in the art.
[ examples ]
Production example 1
Production of Compound P2
27.2g of 1, 4-dibromo-2, 5-difluorobenzene (P1) and 24g of trimethylchlorosilane (TMSCl) were mixed with 200ml of Tetrahydrofuran (THF) under nitrogen and cooled to-78 ℃. Then, 220ml of lithium diisopropylamide (LDA, 2M) was slowly added dropwise thereto, and after stirring at-78 ℃ for 1 hour, the temperature was slowly raised to normal temperature. After the reaction was completed, it was extracted with 3% dilute hydrochloric acid and dichloromethane, dried over anhydrous sodium sulfate and filtered. After methylene chloride was distilled under reduced pressure, it was washed with cold methanol to obtain 33.3g of a white solid.
Then, 33g of the compound obtained in the above reaction was mixed with 1320ml of chloroform, followed by stirring for 30 minutes under a nitrogen atmosphere, and the temperature of the reaction product was cooled to-78 ℃. 317ml of 1mol of iodine monochloride (ICl) was slowly added dropwise thereto, and after stirring at the same temperature for 1 hour, the temperature was raised to room temperature and stirred for 2 hours. After the reaction is finished, sodium thiosulfate (Na) is used
2S
2O
3) The aqueous solution was quenched, extracted, dried over anhydrous sodium sulfate and filtered. Recrystallization from ethanol and drying gave 36.5g of Compound P2.
Production of Compound P3
The compound P2(1, 4-dibromo-2, 5-di-tert-butyl ether)Fluoro-3, 6-diiodobenzene) (26.18g, 50mmol) and phenylboronic acid (12.2g, 100mmol) were dissolved in 800ml of Tetrahydrofuran (THF). Adding sodium carbonate (Na) thereto
2CO
3)2M solution (500mL) and tetrakis (triphenylphosphine) palladium (Pd (PPh)
3)
44.6g, 4mmol) under reflux for 12 hours. After the reaction was completed, the reaction mixture was cooled to normal temperature, and the resultant mixture was extracted with water and toluene 3 times. After the toluene layer was separated, the filtrate dried over magnesium sulfate (magnesium sulfate) and filtered was distilled under reduced pressure. The concentrated compound was subjected to column chromatography using a solution in which hexane and ethyl acetate were mixed at a volume ratio of 4:1, to thereby obtain 20.2g of compound P3. After drying in a vacuum oven for 24 hours, the resulting solid (P3) was confirmed by mass spectrometry to have a peak at M/Z422.
Preparation of Compound P4
The above compound P3(14.0g, 33.1mmol) was dissolved in 600ml of N, N-dimethylformamide. To this was added copper cyanide (CuCN, 6g, 67mmol) and refluxed under nitrogen. After the reaction, the reaction mixture was cooled to room temperature, and the resulting mixture was extracted with water and ethyl acetate. The ethyl acetate layer was separated, distilled under reduced pressure, and the compound was concentrated. Then, it was recrystallized from tetrahydrofuran, thereby obtaining 10.4g of compound P4. The peak at M/Z316 was confirmed by mass spectrometry of the obtained solid.
Preparation of Compound 1
9H-carbazole (2.8g, 17mmol), potassium carbonate (2.4g, 17mmol) and 40ml of dimethyl sulfoxide were mixed, and stirred under nitrogen at room temperature for 1 hour. Compound P4(2.6g, 8.3mmol) was added to the reaction mixture and stirred at 50 ℃ for 16 hours. Cooling to normal temperature, dripping distilled water and filtering. The resulting solid was dissolved in dichloromethane, and the organic layer was separated, dried over magnesium sulfate, filtered through silica gel, and concentrated. Recrystallization from methylene chloride and ethanol produced 2g of compound 1. The peak at M/Z610 was confirmed by mass spectrometry of the obtained solid.
Production example 2
Production of Compound 2
1.6g of Compound 2 was produced in the same manner as for Compound 1, except that 3.3g and 17mmol of 3, 6-dimethyl-9H-carbazole were used instead of 9H-carbazole. The peak at 666M/Z was confirmed by mass spectrometry of the obtained solid.
Production example 3
Production of Compound 3
1.8g of Compound 3 was produced in the same manner as in Compound 1 except that 4.8g of 17mmol of 7, 7-dimethyl-5, 7-dihydroindeno [2,1-b ] carbazole was used in place of 9H-carbazole. The peak at M/Z842 was confirmed by mass spectrometry of the obtained solid.
Production example 4
Production of Compound P5
22.8g of Compound P5 was produced by the same method as the synthesis of Compound P3, except that [1,1' -biphenyl ] -2-ylboronic acid (19.8g, 100mmol) was used in place of phenylboronic acid. The obtained solid was measured by mass spectrometry to confirm a peak at M/Z574.
Production of Compound P6
Production was carried out in the same manner as the synthesis of compound P4 except that compound P5(19.1g, 33.1mmol) was used instead of compound P3, whereby 11.8g of compound P6 was obtained. The peak at M/Z468 was confirmed by mass spectrometry of the obtained solid.
Preparation of Compound 4
1.6g of Compound 4 was obtained by the same method as the synthesis of Compound 1, except that P6(3.9g, 8.3mmol) was used in place of P4. The peak at M/Z762 was confirmed by mass spectrometry of the obtained solid.
Production example 5
Production of Compound 5
2.2g of compound 5 was produced by the same method as that for compound 4, except that 3.3g and 17mmol of 3, 6-dimethyl-9H-carbazole were used instead of 9H-carbazole. The peak at 818 was confirmed by mass spectrometry of the obtained solid.
Production example 6
Production of Compound 6
2.2g of Compound 6 was produced in the same manner as in Compound 4 except that 4.8g of 17mmol of 7, 7-dimethyl-5, 7-dihydroindeno [2,1-b ] carbazole was used in place of 9H-carbazole. The peak at M/Z994 was confirmed by mass spectrometry of the obtained solid.
Production example 7
Production of Compound P7
Preparation was carried out in the same manner as for the synthesis of compound P3, except that (4-fluorophenyl) boronic acid (14.0g, 100mmol) was used instead of phenylboronic acid, thereby preparing 20.6g of compound P7. The solid obtained was measured by mass spectrometry to confirm the peak at M/Z458.
Production of Compound P8
The preparation was carried out in the same manner as the synthesis of the compound P4 except that the compound P7(15.2g, 33.1mmol) was used instead of the compound P3, whereby 9.6g of the compound P8 was obtained. The peak at M/Z352 was confirmed by mass spectrometry of the obtained solid.
Preparation of Compound 7
1.2g of Compound 7 was obtained by the same method as the synthesis of Compound 1 except that Compound P8(2.9g, 8.3mmol) was used in place of Compound P4. The peak at M/Z646 was confirmed by mass spectrometry of the obtained solid.
Production example 8
Production of Compound 8
2.2g of compound 8 was produced by the same method as that for compound 7, except that 3, 6-dimethyl-9H-carbazole (3.3g, 17mmol) was used instead of 9H-carbazole. The peak at M/Z702 was confirmed by mass spectrometry of the obtained solid.
Production example 9
Production of Compound 9
2.2g of Compound 9 was produced in the same manner as in Compound 7 except that 4.8g of 17mmol of 7, 7-dimethyl-5, 7-dihydroindeno [2,1-b ] carbazole was used in place of 9H-carbazole. The peak at M/Z878 was confirmed by mass spectrometry of the obtained solid.
Production example 10
Production of Compound P9
Preparation was carried out in the same manner as for the synthesis of compound P3, except that (4-cyanophenyl) boronic acid (14.7g, 100mmol) was used instead of phenylboronic acid, thereby preparing 20.0g of compound P9. The obtained solid was measured by mass spectrometry to confirm a peak at M/Z472.
Production of Compound P10
The preparation was carried out in the same manner as in the synthesis of compound P4 except that P9(15.7g, 33.1mmol) was used instead of P3, whereby 10.2g of compound P10 was obtained. The peak at M/Z366 was confirmed by mass spectrometry of the obtained solid.
Preparation of Compound 10
1.4g of Compound 8 was obtained by the same method as the synthesis of Compound 1, except that P10(3.0g, 8.3mmol) was used in place of P4. The peak at M/Z660 was confirmed by mass spectrometry of the obtained solid.
Production example 11
Production of Compound 11
2.0g of compound 11 was produced in the same manner as in compound 10, except that 3.3g and 17mmol of 3, 6-dimethyl-9H-carbazole were used instead of 9H-carbazole. The peak at M/Z716 was confirmed by mass spectrometry of the obtained solid.
Production example 12
Production of Compound 12
2.4g of Compound 12 was produced in the same manner as in Compound 10 except that 4.8g of 17mmol of 7, 7-dimethyl-5, 7-dihydroindeno [2,1-b ] carbazole was used in place of 9H-carbazole. The peak at M/Z892 was confirmed by mass spectrometry of the obtained solid.
Production example 13
Production of Compound P11
The preparation was carried out in the same manner as the synthesis of compound P3 except that (4- (tert-butyl) phenyl) boronic acid (17.8g, 100mmol) was used instead of phenylboronic acid, thereby preparing 20.4g of compound P11. The obtained solid was measured by mass spectrometry to confirm the peak at M/Z534.
Production of Compound P12
The preparation was carried out in the same manner as in the synthesis of compound P4 except that P11(15.7g, 33.1mmol) was used instead of P3, whereby 10.4g of compound P12 was obtained. The peak at 428 was confirmed by mass spectrometry of the obtained solid.
Preparation of Compound 13
The preparation was carried out in the same manner as the synthesis of Compound 1 using P12(3.6g, 8.3mmol) in place of P4, whereby 1.4g of Compound 13 was obtained. The peak at M/Z722 was confirmed by mass spectrometry of the obtained solid.
Production example 14
Production of Compound 14
2.0g of compound 14 was produced by the same method as that for compound 13, except that 3.3g and 17mmol of 3, 6-dimethyl-9H-carbazole were used instead of 9H-carbazole. The peak at M/Z778 was confirmed by mass spectrometry of the obtained solid.
[ example 1]
Fabrication of organic light emitting devices
First, a glass substrate having an ITO electrode attached thereto, which was 40mm × 40mm × 0.5mm in thickness, was ultrasonically washed with isopropyl alcohol, acetone, and deionized Water (DI Water) for 5 minutes, and then dried in an oven at 100 ℃. After the substrate was washed, O was performed in a vacuum state
2The substrate was plasma-treated for 2 minutes and transported to a deposition chamber for depositing another layer thereon. At about 10
-7An organic material layer was deposited on ITO on a glass substrate by evaporation from a heating boat under vacuum in the following order. At this time, the deposition rate of the organic materialSet to 10 nm/s.
1. Hole Injection Layer (HIL) HAT-CN with a thickness of 10nm
2. Hole Transport Layer (HTL): NPB of 75nm thickness
3. Electron Blocking Layer (EBL): mCBP, thickness 15nm
4. Luminescent substance layer (EML): 90% by weight of TH1, 10% by weight of Compound 1, thickness 35nm
5. Hole Blocking Layer (HBL): b3PYMPM with a thickness of 10nm
6. Electron Transport Layer (ETL) TPBi with a thickness of 25nm
7. Electron Injection Layer (EIL): LiF with a thickness of 80nm
8. Cathode: al, thickness 100nm
After forming a CPL (capping layer) into a film, the film is sealed with glass. After the deposition of such a layer, the film is transferred from the deposition chamber into a drying oven to form a coating film, and then encapsulated with a UV curable epoxy resin and a water absorbent (getter).
[ example 2]
As a dopant of the light emitting layer, compound 2 was used instead of compound 1, thereby manufacturing an organic light emitting device.
[ example 3]
As a dopant of the light-emitting layer, compound 3 was used instead of compound 1, thereby manufacturing an organic light-emitting device.
[ example 4]
As a dopant of the light-emitting layer, compound 4 was used instead of compound 1, thereby manufacturing an organic light-emitting device.
[ example 5]
As a dopant of the light-emitting layer, compound 5 was used instead of compound 1, thereby producing an organic light-emitting device.
[ example 6]
As a dopant of the light-emitting layer, compound 6 was used instead of compound 1, thereby producing an organic light-emitting device.
[ example 7]
As a dopant of the light-emitting layer, compound 8 was used instead of compound 1, thereby producing an organic light-emitting device.
[ example 8]
As a dopant of the light-emitting layer, compound 9 was used instead of compound 1, thereby producing an organic light-emitting device.
[ example 9]
As a dopant of the light-emitting layer, compound 10 was used instead of compound 1, thereby producing an organic light-emitting device.
[ example 10]
As a dopant of the light-emitting layer, compound 13 was used instead of compound 1, thereby manufacturing an organic light-emitting device.
[ example 11]
As a dopant of the light-emitting layer, compound 14 was used instead of compound 1, thereby producing an organic light-emitting device.
Comparative example 1
As a dopant of the light-emitting layer, compound D1 was used instead of compound 1, thereby producing an organic light-emitting device.
Comparative example 2
As a dopant of the light-emitting layer, compound D2 was used instead of compound 1, thereby producing an organic light-emitting device.
Comparative example 3
As a dopant of the light-emitting layer, compound D3 was used instead of compound 1, thereby producing an organic light-emitting device.
Comparative example 4
As a dopant of the light-emitting layer, compound D4 was used instead of compound 1, thereby producing an organic light-emitting device.
Comparative example 5
As a dopant of the light-emitting layer, compound D5 was used instead of compound 1, thereby producing an organic light-emitting device.
Comparative example 6
As a dopant of the light-emitting layer, compound D6 was used instead of compound 1, thereby producing an organic light-emitting device.
[ Experimental example 1]
The properties were measured for the organic light-emitting devices produced in examples 1 to 11 and comparative examples 1 to 6, which were produced with the thickness of the light-emitting layer doped with the delayed fluorescence dopant at 10 wt% being 35 nm. Device characteristics were evaluated at room temperature using a power supply (KEITHLEY) and a photometer (PR 650). Measured at 10mA/cm for each organic light emitting device
2The drive voltage (V), the current efficiency (cd/A), the power efficiency (lm/W), and the luminance (cd/m) measured at the current density of (1)
2) Time (T) required for reducing luminance from 3000nit to 95%
95). The measurement results are shown in table 1 below.
[ Table 1]
The devices of examples 1 to 11 using the heterocyclic compound of the present invention have a low driving voltage, a high current efficiency, a high power efficiency, a high luminance, and a high life characteristic, as compared with the devices of comparative examples 1 to 6.
Claims (14)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1, the metal oxide is represented by,
a1 to a5, equal to or different from each other, are each independently hydrogen; a halogen group; a cyano group; a haloalkyl group; an alkyl group; an alkenyl group; a haloalkoxy group; aryl substituted or unsubstituted with a halogen group, cyano, haloalkyl, alkyl or haloalkoxy; or a heteroaryl group, or adjacent groups are bonded to each other to form an aromatic ring,
r1 to R8 and R11 to R18 are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amide group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted arylphosphorus group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or adjacent groups are combined with each other to form a substituted or unsubstituted ring,
n is 1 or 2, and n is a hydrogen atom,
when n is 2, the structures in parentheses are the same or different from each other,
when n is 1 and any one of the A1-A5 is heteroaryl, the remainder are hydrogen.
2. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-1 or 1-2:
chemical formula 1-1
Chemical formula 1-2
In the chemical formulas 1-1 and 1-2,
a1 to A5, R1 to R8 and R11 to R18 are as defined in said chemical formula 1,
a11 to a15, equal to or different from each other, are each independently hydrogen; a halogen group; a cyano group; a haloalkyl group; an alkyl group; an alkenyl group; a haloalkoxy group; aryl substituted or unsubstituted with a halogen group, cyano, haloalkyl, alkyl, or haloalkoxy; or a heteroaryl group, or adjacent groups are bonded to each other to form an aromatic ring.
3. The compound of claim 1, wherein the R1-R8 and R11-R18 are the same or different from each other, each independently being hydrogen or alkyl.
4. The compound of claim 1, wherein adjacent ones of the R1-R8 and R11-R18 combine with each other to form a hydrocarbon ring substituted with an alkyl group.
5. The compound of claim 1, wherein the compound of formula 1 is selected from the group consisting of:
6. the compound according to claim 1, wherein the compound represented by the chemical formula 1 is a delayed fluorescence compound.
7. An organic light emitting device, comprising: a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound according to any one of claims 1 to 6.
8. The organic light emitting device of claim 7, wherein the organic layer comprises a light emitting layer comprising the compound.
9. The organic light-emitting device according to claim 7, wherein the organic layer comprises a light-emitting layer containing the compound as a dopant of the light-emitting layer.
10. An organic light-emitting device according to claim 9 wherein the dopant has a maximum light emission wavelength of 480nm to 570 nm.
11. The organic light-emitting device according to claim 7, wherein the organic layer comprises a light-emitting layer containing, as a host of the light-emitting layer, any one or more selected from an aromatic fused ring derivative and a heterocyclic ring-containing compound.
12. The organic light-emitting device according to claim 11, wherein the host contains any one or more selected from the following compounds:
13. the organic light-emitting device according to claim 7, wherein the organic layer comprises a light-emitting layer containing the compound as a dopant of the light-emitting layer and containing any one or more selected from an aromatic fused ring derivative and a heterocyclic ring-containing compound as a host of the light-emitting layer.
14. The organic light emitting device according to claim 13, wherein the light emitting layer comprises the dopant and the host in a weight ratio of 1:99 to 50: 50.
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| KR1020180147707A KR102181841B1 (en) | 2017-11-28 | 2018-11-26 | Compound and organic light-emitting device comprising the same |
| PCT/KR2018/014859 WO2019107932A1 (en) | 2017-11-28 | 2018-11-28 | Compound and organic light emitting device comprising same |
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