CN110606824B - Compound and organic light-emitting element comprising same - Google Patents
Compound and organic light-emitting element comprising same Download PDFInfo
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- CN110606824B CN110606824B CN201910505660.8A CN201910505660A CN110606824B CN 110606824 B CN110606824 B CN 110606824B CN 201910505660 A CN201910505660 A CN 201910505660A CN 110606824 B CN110606824 B CN 110606824B
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
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- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
Abstract
The present specification provides a compound represented by chemical formula 1 and an organic light emitting element including the same. In the chemical formula 1, L1 and L2 are the same or different from each other, each is independently a single bond, or a substituted or unsubstituted arylene group, a is a group represented by the following chemical formula 2, B is hydrogen, or a substituted or unsubstituted aryl group, in the chemical formula 2, at least one of X1 to X3 is N, the others are each independently CR, R is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and Ar1 and Ar2 are the same or different from each other, each is independently hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. Chemical formula 1Chemical formula 2
Description
Technical Field
The present application claims priority based on korean patent application No. 10-2018-0068199 filed 14 months 2018 to the korean patent office and korean patent application No. 10-2019-0031036 filed 03 months 19 to the korean patent office, the entire contents of which are included in the present specification.
The present application relates to a compound represented by chemical formula 1 and an organic light emitting element including the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic substance. An organic light emitting element utilizing an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to improve efficiency and stability of the organic light-emitting element, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting element, if a voltage is applied between both electrodes, holes are injected from the anode to the organic layer, electrons are injected from the cathode to the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, 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 elements as described above.
Prior art literature
Patent literature
Patent document 1: international patent application publication No. 2003/012890
Disclosure of Invention
The present application provides a compound represented by chemical formula 1 and an organic light emitting element including the same.
The present application provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the chemical formula 1, the chemical formula is shown in the drawing,
l1 and L2 are the same or different from each other and are each independently a single bond, or a substituted or unsubstituted arylene group,
a is a group represented by the following chemical formula 2,
b is hydrogen, or substituted or unsubstituted aryl,
[ chemical formula 2]
In the above-mentioned chemical formula 2,
at least one of X1 to X3 is N, the others are each independently CR,
r is hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,
ar1 and Ar2 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In addition, the present application provides an organic light emitting element, including: a first electrode, a second electrode provided opposite to 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 contains the compound.
An organic light emitting element using the compound according to an embodiment of the present application can achieve low driving voltage, high light emitting efficiency, or long life.
Drawings
Fig. 1 illustrates an example of an organic light-emitting element in which a substrate 1, an anode 2, a light-emitting layer 3, a hole-suppressing layer 4, and a cathode 5 are stacked in this order.
Fig. 2 illustrates an example of an organic light-emitting element in which a substrate 1, an anode 2, a hole injection layer 6, a hole transport layer 7, an electron suppression layer 8, a light-emitting layer 3, a hole suppression layer 4, an electron injection and transport layer 9, and a cathode 5 are stacked in this order.
Symbol description
1: substrate board
2: anode
3: light-emitting layer
4: hole-inhibiting layer
5: cathode electrode
6: hole injection layer
7: hole transport layer
8: electron suppression layer
9: electron injection and transport layers
Detailed Description
The present specification will be described in more detail below.
The present specification provides a compound represented by the above chemical formula 1.
According to an embodiment of the present application, the compound represented by the above chemical formula 1 may exhibit long life and high efficiency characteristics by having a parent nucleus structure as described above, thereby having an advantage of being able to adjust a triplet level.
Examples of substituents in the present specification are described below, but are not limited thereto.
The term "substituted" refers to a compound in which a hydrogen atom bonded to a carbon atom is replaced with another substituent, and the substituted position is not limited as long as it is a position where the hydrogen atom is substituted, that is, a position where the 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 that the substituted or unsubstituted member is substituted with 1 or 2 or more substituents selected from the group consisting of hydrogen, a halogen group, a nitrile group, a nitro group, a hydroxyl group, an ester group, a carbonyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, or is substituted or unsubstituted with a substituent in which 2 or more substituents selected from the above-described exemplified substituents are linked, 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.
Examples of halogen radicals in this specification are fluorine, chlorine, bromine or iodine.
In the present specification, the number of carbon atoms of the ester group is not particularly limited, and is preferably 1 to 50. 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, and is preferably 1 to 50 carbon atoms. Specifically, the compound may have the following structure, but is 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 50. Specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but cycloalkyl having 3 to 60 carbon atoms is preferable. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but the present invention is not limited thereto.
In the present specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic group. 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, benzyloxy, p-methylbenzyloxy and the like are possible, but not limited thereto.
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. 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, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25. Specifically, the monocyclic aryl group may be phenyl, biphenyl, terphenyl, or the like, but is not limited thereto.
In the case where the above aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, and the number of carbon atoms is preferably 10 to 24. Specifically, the polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl,A group, a fluorenyl group, etc., but is not limited thereto.
In the present specification, the above fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
In the case where the fluorenyl group is substituted, it may be that However, the present invention is not limited thereto.
In this specification, the heterocyclic group contains one or more non-carbon atoms, i.e., hetero atoms, and specifically, the hetero atoms may contain one or more selected from O, N, se and S. The number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo- >Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), thiazolyl, and iso ∈>Azolyl, (-) -and (II) radicals>Diazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In this specification, the heteroarylene group is a 2-valent group, and the above description of the heterocyclic group can be applied thereto.
In this specification, arylene is a 2-valent group, and the above description of aryl can be applied thereto.
In the present description of the invention,represents different substituents or the site of attachment to the binding moiety.
According to an embodiment of the present application, the above-mentioned L1 and L2 are the same or different from each other, and each is independently a single bond, or a substituted or unsubstituted arylene group.
According to an embodiment of the present application, the above-mentioned L1 and L2 are the same or different from each other, and are each independently a single bond, or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
According to an embodiment of the present application, the above-mentioned L1 and L2 are the same or different from each other, and are each independently a single bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
According to an embodiment of the present application, the above-mentioned L1 and L2 are the same or different from each other, and are each independently a single bond, or a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.
According to an embodiment of the present application, L1 and L2 are the same or different from each other, and each is independently a single bond or is selected from any one of the following structural formulas.
According to an embodiment of the present application, L1 and L2 are the same or different from each other, and each is independently a single bond or is selected from any one of the following structural formulas.
According to an embodiment of the present application, a is represented by the following chemical formula 2.
[ chemical formula 2]
In the chemical formula 2, the chemical formula is shown in the drawing,
at least one of X1 to X3 is N, the others are each independently CR,
r is hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,
ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
According to an embodiment of the present application, R is hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl of 1 to 30 carbon atoms, substituted or unsubstituted aryl of 6 to 60 carbon atoms, or substituted or unsubstituted heterocyclyl of 2 to 60 carbon atoms.
According to an embodiment of the present application, R is hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl of 1 to 15 carbon atoms, substituted or unsubstituted aryl of 6 to 30 carbon atoms, or substituted or unsubstituted heterocyclyl of 2 to 30 carbon atoms.
According to an embodiment of the present application, R is hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl of 1 to 10 carbon atoms, substituted or unsubstituted aryl of 6 to 15 carbon atoms, or substituted or unsubstituted heterocyclyl of 2 to 15 carbon atoms.
According to an embodiment of the present application, R is hydrogen or deuterium.
According to an embodiment of the present application, R is hydrogen.
According to an embodiment of the present application, ar1 and Ar2 are the same or different from each other, and are each independently 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.
According to an embodiment of the present application, ar1 and Ar2 are the same or different from each other, and are each independently 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.
According to an embodiment of the present application, ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.
According to an embodiment of the present application, ar1 and Ar2 are the same or different from each other and are each independently hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorene, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted naphthobenzofuranyl, or substituted or unsubstituted naphthobenzothienyl.
According to an embodiment of the present application, ar1 and Ar2 are the same or different from each other and are each independently hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, or substituted or unsubstituted carbazolyl.
According to an embodiment of the present application, ar1 and Ar2 are the same or different from each other, each independently being any one selected from the following structural formulae.
According to an embodiment of the present application, ar1 and Ar2 are the same or different from each other, each independently being any one selected from the following structures.
According to an embodiment of the present application, ar1 and Ar2 are the same or different from each other, each independently hydrogen or any one group selected from the following structures.
According to one embodiment of the present application, B is a substituted or unsubstituted aryl group.
According to one embodiment of the present application, B is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
According to one embodiment of the present application, B is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to one embodiment of the present application, B is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.
According to an embodiment of the present application, B is hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, or substituted or unsubstituted spirobifluorenyl.
According to an embodiment of the present application, B is phenyl, biphenyl, naphthyl, fluorenyl substituted with methyl, fluorenyl substituted with phenyl, or spirobifluorenyl.
According to an embodiment of the present application, B is hydrogen or any one selected from the following structures.
According to an embodiment of the present application, B is any one selected from the following structures.
According to an embodiment of the present application, the above chemical formula 2 is represented by any one of the following chemical formulas 3 to 7.
[ chemical formula 3]
[ chemical formula 4]
[ chemical formula 5]
[ chemical formula 6]
[ chemical formula 7]
In the above chemical formulas 3 to 7,
r1 to R6 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, cyano, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group,
ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
According to an embodiment of the present application, the definitions of Ar1 and Ar2 of the above chemical formulas 3 to 7 are the same as those of Ar1 and Ar2 of chemical formula 2.
According to an embodiment of the present application, R1 to R6 are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano 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.
According to an embodiment of the present application, R1 to R6 are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl 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.
According to an embodiment of the present application, R1 to R6 are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.
According to an embodiment of the present application, in the above chemical formula 1, L1 and L2 are the same or different from each other, and each is independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
According to an embodiment of the present application, in the above chemical formula 1, L1 and L2 are the same or different from each other, and each is independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
According to an embodiment of the present application, L1 is a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.
According to one embodiment of the present application, L1 is a single bond, a substituted or unsubstituted phenylene group.
According to one embodiment of the present application, L1 is a single bond or phenylene.
According to one embodiment of the present application, L1 is a single bond.
According to one embodiment of the present application, L1 is phenylene.
According to one embodiment of the present application, L1 is biphenylene.
According to an embodiment of the present application, L2 is a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.
According to an embodiment of the present application, L2 is a single bond, or a substituted or unsubstituted phenylene group.
According to one embodiment of the present application, L2 is a single bond or phenylene.
According to one embodiment of the present application, L2 is a single bond.
According to an embodiment of the present application, the compound represented by the above chemical formula 1 is any one selected from the following structural formulas.
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In addition, the present application provides an organic light-emitting element comprising the above-described compound.
In one embodiment of the present application, there is provided an organic light emitting device, including: a first electrode, a second electrode provided opposite to 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 contains the compound.
In this application, when it is stated that a certain member is located "on" another member, it includes not only the case where the certain member is in contact with the other member but also the case where the other member exists between the two members.
In the present application, when a certain component is indicated as being "included" in a certain portion, unless otherwise stated, it means that other components may be further included, and not excluded.
The organic layer of the organic light-emitting element of the present application 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 element of the present invention may have a structure including a hole injection layer, a hole transport layer, a hole suppression layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like as an organic layer. However, the structure of the organic light emitting element is not limited thereto, and may include a smaller number of organic layers.
In one embodiment of the present application, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.
In one embodiment of the present application, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.
In one embodiment of the present application, the organic layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer includes the compound.
In one embodiment of the present application, the organic layer includes a hole-suppressing layer, and the hole-suppressing layer includes the compound.
In one embodiment of the present application, the organic light-emitting element may further include one or more layers selected from a hole injection layer, a hole transport layer, an electron injection layer, an electron suppression layer, and a hole suppression layer.
The light emitting layer may include a dopant material. The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include dibenzofuran derivatives and ladder-type furan compounds Pyrimidine derivatives, etc., but are not limited thereto.
In one embodiment of the present application, the thickness of the organic layer containing the compound of formula 1 isTo the point of
In one embodiment of the present application, the organic light emitting device includes: a first electrode, a second electrode provided opposite to the first electrode, a light-emitting layer provided between the first electrode and the second electrode, and two or more organic layers provided between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode, wherein at least one of the two or more organic layers contains the compound. In one embodiment of the present application, the two or more organic layers may be selected from two or more of an electron-suppressing layer, a hole-injecting layer, and a hole-transporting layer.
In one embodiment of the present application, the organic layer includes a hole injection layer or a hole transport layer containing another compound in addition to the organic layer containing the compound, and the other compound includes an arylamino group, a carbazole group, or a benzocarbazole group.
In another embodiment, the organic light-emitting element may be a standard structure (normal type) organic light-emitting element in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.
In another embodiment, the organic light-emitting element may be an organic light-emitting element having a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.
For example, a structure of an organic light emitting element according to an embodiment of the present application is illustrated in fig. 1 and 2.
Fig. 1 illustrates a structure of an organic light-emitting element in which a substrate 1, an anode 2, a light-emitting layer 3, a hole-suppressing layer 4, and a cathode 5 are stacked in this order. In the structure described above, the above-described compound may be contained in the above-described hole-suppressing layer 4.
Fig. 2 illustrates an example of an organic light-emitting element in which a substrate 1, an anode 2, a hole injection layer 6, a hole transport layer 7, an electron suppression layer 8, a light-emitting layer 3, a hole suppression layer 4, an electron injection and transport layer 9, and a cathode 5 are stacked in this order. In the above-described structure, the compound may be contained in one or more of the light-emitting layer 3, the hole-suppressing layer 4, the electron-injecting and transporting layer 9, and the hole-injecting layer 6.
The organic light-emitting element of the present application may be manufactured by materials and methods well known in the art, except that one or more of the organic layers contains the compound of the present application, i.e., the above compound.
When the organic light emitting element includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
The organic light-emitting element of the present application may be manufactured using materials and methods well known in the art, except that one or more of the organic layers contains the compound represented by the above chemical formula 1.
For example, the organic light emitting element of the present application can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, it can be manufactured as follows: PVD (physical Vapor Deposition) such as sputtering (sputtering) or electron beam evaporation (physical vapor deposition) is used to deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is deposited on the organic layer. In addition to this method, an organic light-emitting element may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
In addition, in the case of manufacturing an organic light-emitting device, the compound of chemical formula 1 may be used to form an organic layer not only by a vacuum vapor deposition method but also by a solution coating method. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting element can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (international patent application publication No. WO 2003/012890). However, the manufacturing method is not limited thereto.
In one embodiment of the present application, the first electrode is an anode, and the second electrode is a cathode.
In another embodiment, the first electrode is a cathode, and the second electrode is an anode.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, and the like, or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), and the like; such as ZnO, al or SnO 2 A combination of metals such as Sb and oxides; such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene)]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate electron injection 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; such as LiF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that injects holes from an electrode, and the following compounds are preferable as the hole injection substance: the light-emitting device has a hole transporting capability, a hole injecting effect from an anode, an excellent hole injecting effect for a light-emitting layer or a light-emitting material, prevention of migration of excitons generated in the light-emitting layer to the electron injecting layer or the electron injecting material, and an excellent thin film forming capability. The HOMO (highest occupied molecular orbital ) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophenes, arylamine-based organic substances, carbazole-based organic substances, cyanide-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, and mixtures of two or more compounds in the above examples.
The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and as a hole-transporting substance, a substance that can receive holes from the anode or the hole-injecting layer and transport the holes to the light-emitting layer, and a substance having a large hole mobility is suitable. Specific examples thereof include, but are not limited to, arylamine-based organic substances, carbazole-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
The light-emitting substance is a substance capable of receiving holes and electrons from the hole-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, anthracene-based compounds, arylamine-based compounds, or a mixture of two or more compounds in the above examples, and the like, but is not limited thereto.
The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and as an electron transporting substance, a substance that can well inject electrons from the cathode and transfer the electrons to the light emitting layer, and a substance having a large electron mobility is suitable. Specific examples include, but are not limited to, al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavone-metal complexes, triazine-based compounds, liQ, and mixtures of two or more compounds of the above examples. The electron transport layer may be used with any desired cathode material as used in the art. In particular, examples of suitable cathode materials are the usual materials having a low work function accompanied by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a silver layer.
The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound as follows: has an electron transporting ability, an electron injecting effect from a cathode, an excellent electron injecting effect 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 has an excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane (Anthraquinone), diphenoquinone, thiopyran dioxide, Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethane, anthrones, derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, triazine-based compounds, liQ, and mixtures of two or more compounds in the above examples.
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 electron suppression layer is a layer that prevents holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer, and can improve the lifetime and efficiency of the element, and may be formed at an appropriate portion between the light emitting layer and the electron injection layer using a known material, if necessary.
The hole-suppressing layer is a layer that prevents holes from reaching the cathode, and can be formed under the same conditions as the hole-injecting layer. Specifically, there are The diazole derivative, triazole derivative, phenanthroline derivative, triazine compound, pyrimidine compound, pyridine compound, BCP, aluminum complex (aluminum complex), and the like, but are not limited thereto.
The organic light emitting element according to the present application may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
The production of the compound represented by the above chemical formula 1 and the organic light-emitting element including the same is specifically described in the following examples. However, the following examples are given by way of illustration of the present specification, and the scope of the present specification is not limited thereto.
< production example >
Production example A-1 ]
Compound A-1 was produced according to the following reaction scheme.
< production example A-2>
Compound A-2 was produced according to the following reaction scheme.
Production example A-3 ]
Compound A-3 was produced according to the following reaction scheme.
Production example A-4 ]
Compound A-4 was produced according to the following reaction scheme.
Production example A-5 ]
Compound A-5 was produced according to the following reaction scheme.
< production example A-6>
Compound A-6 was produced according to the following reaction scheme.
< production example B-1>
Compound B-1 was produced according to the following reaction scheme.
< production example B-2>
Compound B-2 was produced according to the following reaction scheme.
< production example B-3>
Compound B-3 was produced according to the following reaction scheme.
< production example B-4>
Compound B-4 was produced according to the following reaction scheme.
< production example B-5>
Compound B-5 was produced according to the following reaction scheme.
< production example B-6>
Compound B-6 was produced according to the following reaction scheme.
Production example 1. Production of Compound 1 described below
After compound A-1 (4.67 g,13.82 mmol) and a-1 (7.41 g,14.51 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.48 g,0.41 mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 160ml of tetrahydrofuran to give compound 1 (7.16 g, 75%).
MS[M+H] + ＝688
Production example 2 production of the following Compound 2
After compound A-2 (5.12 g,13.20 mmol) and a-2 (6.03 g,13.86 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.46 g,0.40 mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 210ml of tetrahydrofuran to give compound 2 (6.11 g, 70%).
MS[M+H] + ＝662
Production example 3 production of the following Compound 3
After compound A-3 (5.34 g,13.76 mmol) and a-3 (6.29 g,14.45 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.48 g,0.41 mmol) was added, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 230ml of ethyl acetate to give compound 3 (6.78 g, 74%).
MS[M+H] + ＝662
Production example 4 production of the following Compound 4
After compound A-4 (5.34 g,12.90 mmol) and a-4 (5.88 g,13.54 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.45 g,0.39 mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 250ml of ethyl acetate to give compound 4 (5.96 g, 69%).
MS[M+H] + ＝687
Production example 5> production of the following Compound 5
After compound A-5 (4.56 g,10.41 mmol) and a-5 (4.73 g,10.93 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.36 g,0.31 mmol) was added, and the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 230ml of ethyl acetate to give compound 5 (4.87 g, 66%).
MS[M+H] + ＝710
Production example 6 production of the following Compound 6
After compound A-6 (5.73 g,12.62 mmol) and a-6 (5.75 g,13.25 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.44 g,0.38 mmol) was added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 210ml of ethyl acetate to give compound 6 (6.67 g, 73%).
MS[M+H] + ＝727
Production example 7 production of the following Compound 7
After compound B-1 (5.37 g,15.66 mmol) and B-1 (7.07 g,16.44 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.54 g,0.47 mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 210ml of tetrahydrofuran to give compound 7 (4.92 g, 51%).
MS[M+H] + ＝612
Production example 8 production of the following Compound 8
After compound B-2 (8.99 g,18.74 mmol) and B-2 (6.37 g,17.84 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.62 g,0.54 mmol) was added, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 210ml of tetrahydrofuran to give compound 8 (7.34 g, 61%).
MS[M+H] + ＝676
Production example 9> production of the following Compound 9
After compound B-3 (8.27 g,17.23 mmol) and B-3 (6.12 g,16.41 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.57 g,0.49 mmol) was added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 220ml of ethyl acetate to produce compound 9 (6.09 g, 54%).
MS[M+H] + ＝692
Production example 10 production of the following Compound 10
After compound B-4 (7.61 g,15.05 mmol) and B-4 (5.26 g,14.33 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.50 g,0.43 mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 230ml of ethyl acetate to give compound 10 (7.16 g, 70%).
MS[M+H] + ＝712
Production example 11 production of the following Compound 11
After compound B-5 (7.43 g,14.02 mmol) and B-5 (5.77 g,13.36 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.46 g,0.40 mmol) was added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 220ml of ethyl acetate to give compound 11 (6.27 g, 59%).
MS[M+H] + ＝801
Production example 12 production of the following Compound 12
After compound B-6 (9.95 g,18.23 mmol) and B-6 (4.67 g,17.36 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis (triphenylphosphine) palladium (0.60 g,0.52 mmol) was added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 240ml of ethyl acetate to give compound 12 (4.67 g, 41%).
MS[M+H] + ＝652
Experimental example 1-1 ]
Will be as followsThe glass substrate coated with ITO (indium tin oxide) was put into distilled water in which a detergent was dissolved, and washed with ultrasonic waves. At this time, the detergent was a product of fei he hill (Fischer co.) and the distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, it was subjected to ultrasonic washing with distilled water twice for 10 minutes. 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 as an anodeThe hole injection layer was formed by thermal vacuum evaporation of the compound HI1 and the compound HI2 in a ratio of 98:2 (molar ratio). On the hole injection layer, a compound represented by the following formula HT1 is added>Vacuum evaporation is performed to form a hole transport layer. Next, on the hole transport layer, the film thickness is +.>Electron inhibition by vacuum evaporation of EB1 compoundsA layer. Next, the electron suppression layer is formed with a film thickness +.>A compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD were vacuum-evaporated at a weight ratio of 50:1 to form a light-emitting layer. On the above-mentioned light-emitting layer, the film thickness is +.>The compound 1 was vacuum-evaporated to form a hole-suppressing layer. Next, on the hole-suppressing layer, a compound represented by the following chemical formula ET1 and a compound represented by the following chemical formula LiQ were vacuum-evaporated at a weight ratio of 1:1 to give ≡>Form an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added +.>Is made of aluminum +. >The thickness was evaporated to form a cathode. />
In the above process, the vapor deposition rate of the organic matter is maintainedLithium fluoride maintenance of cathodeIs kept at>Is to maintain a vacuum degree of 2X 10 during vapor deposition -7 ～5×10 -6 The support is then fabricated to produce an organic light emitting device.
Experimental examples 1-2 ]
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 2 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 3
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 3 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 4
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 4 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 5
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 5 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 6
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 6 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 7
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 7 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 8
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 8 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 9
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 9 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 10
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 10 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 11
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 11 was used instead of compound 1 in example 1-1.
Experimental examples 1 to 12
An organic light-emitting device was produced in the same manner as in example 1-1 except that compound 12 was used instead of compound 1 in example 1-1.
Comparative examples 1 to 1 ]
An organic light-emitting device was produced in the same manner as in example 1-1 except that the following HB1 compound was used in place of compound 1 in example 1-1.
Comparative examples 1 to 2
An organic light-emitting device was produced in the same manner as in example 1-1 except that the following HB2 compound was used in place of compound 1 in example 1-1.
Comparative examples 1 to 3
An organic light-emitting device was produced in the same manner as in example 1-1 except that the following HB3 compound was used in place of compound 1 in example 1-1.
Comparative examples 1 to 4 ]
An organic light-emitting device was produced in the same manner as in example 1-1 except that the following HB4 compound was used in place of compound 1 in example 1-1.
Comparative examples 1 to 5 ]
An organic light-emitting device was produced in the same manner as in example 1-1 except that the following HB5 compound was used in place of compound 1 in example 1-1.
The compounds of HB1, HB2, HB3, HB4 and HB5 are as follows.
When a current was applied to the organic light emitting elements fabricated in experimental examples 1-1 to 1-12 and comparative examples 1-1 to 1-5, the voltage, efficiency, color coordinates and lifetime were measured, and the results are shown in table 1 below. T95 represents the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.
[ Table 1 ]
As shown in table 1 above, when an organic light-emitting element manufactured by using as a hole-suppressing layer a compound of the present invention having an aryl group at the 1-position and a structure having a triazine-based substituent at the 3-position of the triphenylene core structure, the compound exhibits excellent characteristics in terms of efficiency, driving voltage and/or stability, compared with comparative examples 1-1 and 1-4 in which HB1 and HB4 substituted with a triazine-based substituent at the 2-position of the triphenylene core are used as a hole-suppressing layer, which have been widely used conventionally.
When compared with comparative examples 1-2 and 1-3 in which HB2 and HB3 having a structure in which a triazine-based substituent is substituted at the 1-position of the triphenylene core were used as the hole-suppressing layer, the voltage and efficiency were at similar levels, but the lifetime characteristics were increased by 30% or more.
When compared with comparative examples 1 to 5, which used HB5 having a structure in which a phenyl group was substituted at the 2-position and a triazine-based substituent was substituted at the 7-position of the triphenylene core, as a hole-suppressing layer, very excellent characteristics were exhibited in terms of efficiency, driving voltage, and/or stability.
While the preferred embodiment (hole-suppressing layer) of the present invention has been described above, the present invention is not limited thereto, and it is within the scope of the invention as claimed and the detailed description of the invention that the present invention can be modified into various forms and implemented, and the present invention is also within the scope of the invention.
Claims (4)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1, the chemical formula is shown in the drawing,
l1 is a single bond, phenylene, or biphenylene,
l2 is a single bond, and is a single bond,
a is a group represented by the following chemical formula 2,
b is phenyl, biphenyl, naphthyl, phenanthryl, or fluorenyl substituted or unsubstituted with methyl,
chemical formula 2
In the chemical formula 2 described above, the chemical formula,
at least one of X1 to X3 is N, the others are each independently CR,
r is hydrogen, and the R is hydrogen,
ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group substituted or unsubstituted with a methyl group, a dibenzofuranyl group, a dibenzothienyl group, or a carbazolyl group substituted or unsubstituted with a phenyl group.
2. The compound according to claim 1, wherein the chemical formula 2 is any one of the following chemical formulas 3 to 7:
chemical formula 3
Chemical formula 4
Chemical formula 5
Chemical formula 6
Chemical formula 7
In the chemical formulas 3 to 7, R1 to R6 are each independently hydrogen,
ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group substituted or unsubstituted with a methyl group, a dibenzofuranyl group, a dibenzothienyl group, or a carbazolyl group substituted or unsubstituted with a phenyl group.
3. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the following structural formulas:
4. an organic light emitting element, comprising: a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein the organic layers include a hole-suppressing layer, an electron-transporting layer, or an electron-injecting layer, and the hole-suppressing layer, the electron-transporting layer, or the electron-injecting layer includes the compound according to any one of claims 1 to 3.
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| KR10-2018-0068199 | 2018-06-14 | ||
| KR1020190031036A KR102235989B1 (en) | 2018-06-14 | 2019-03-19 | Compound and organic light emitting device comprising the same |
| KR10-2019-0031036 | 2019-03-19 |
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| KR20100045587A (en) * | 2008-10-24 | 2010-05-04 | 주식회사 이엘엠 | Organic light emitting material and organic light emitting diode having the same |
| KR20140057687A (en) * | 2011-12-30 | 2014-05-13 | 제일모직주식회사 | Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode |
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| KR102490887B1 (en) * | 2015-09-11 | 2023-01-25 | 삼성디스플레이 주식회사 | Organic light emitting device |
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| KR20140057687A (en) * | 2011-12-30 | 2014-05-13 | 제일모직주식회사 | Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode |
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