CN112912370A - Polycyclic compound and organic light-emitting element comprising same - Google Patents
Polycyclic compound and organic light-emitting element comprising same Download PDFInfo
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- CN112912370A CN112912370A CN202080005755.4A CN202080005755A CN112912370A CN 112912370 A CN112912370 A CN 112912370A CN 202080005755 A CN202080005755 A CN 202080005755A CN 112912370 A CN112912370 A CN 112912370A
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- -1 Polycyclic compound Chemical class 0.000 title claims description 52
- 239000000126 substance Substances 0.000 claims abstract description 108
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- 239000010410 layer Substances 0.000 claims description 200
- 125000004432 carbon atom Chemical group C* 0.000 claims description 77
- 229910052805 deuterium Inorganic materials 0.000 claims description 70
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 59
- 239000012044 organic layer Substances 0.000 claims description 56
- 125000001424 substituent group Chemical group 0.000 claims description 55
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 46
- 238000002347 injection Methods 0.000 claims description 44
- 239000007924 injection Substances 0.000 claims description 44
- 125000005843 halogen group Chemical group 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 40
- 125000000623 heterocyclic group Chemical group 0.000 claims description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
- 230000005525 hole transport Effects 0.000 claims description 30
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 239000002019 doping agent Substances 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 21
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- RFWPGPDEXXGEOQ-UHFFFAOYSA-N tert-butyl(methyl)boron Chemical group C[B]C(C)(C)C RFWPGPDEXXGEOQ-UHFFFAOYSA-N 0.000 description 1
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- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
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- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- H10K50/00—Organic light-emitting devices
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- 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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Abstract
The present specification provides a compound represented by chemical formula 1 and an organic light emitting device including the same.
Description
Technical Field
The specification claims priority of korean patent application No. 10-2019-0013525, filed on 1.2.2019 from the korean patent office, the entire contents of which are incorporated herein.
The present specification relates to a compound and an organic light emitting device including the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure composed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. In the structure of such an organic light emitting device, if a voltage is applied between the electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and excitons (exiton) are formed when the injected holes and electrons meet each other, and light is emitted when the excitons transition to the ground state again.
The substances used in organic light-emitting devices are mostly pure organic substances or complex compounds of organic substances and metals. The materials used in the organic light emitting device may be classified into a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, and the like according to the use. Here, as the hole injecting substance or the hole transporting substance, an organic substance having a p-type property, that is, an organic substance which is easily oxidized and has an electrochemically stable state at the time of oxidation is mainly used. On the other hand, as the electron injecting substance or the electron transporting substance, an organic substance having an n-type property, that is, an organic substance which is easily reduced and has an electrochemically stable state at the time of reduction is mainly used. As the light-emitting layer material, a material having both p-type and n-type properties, that is, a material having a stable form in both an oxidized and reduced state is preferable, and when an exciton is formed, a material having high light-emitting efficiency for converting it into light is preferable.
In order to fully utilize the excellent characteristics of the organic light emitting device, development of a substance constituting an organic layer in the device is continuously required.
(patent document 1) Korean patent laid-open publication No. 10-2016-
Disclosure of Invention
Technical subject
The present specification describes a compound and an organic light-emitting device including the same.
Means for solving the problems
One embodiment of the present specification provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-described chemical formula 1,
x is O, S or Si,
Ar1to Ar4The same or different from each other, each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combines with adjacent groups to form a substituted or unsubstituted carbazole,
R1to R8Are the same or different from each other, each being independentAnd R is independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, R is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or1To R81 or more of (a) is deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In addition, the present invention provides an organic light emitting device, comprising: the organic light emitting device includes a first electrode, a second electrode, and 1 or more organic layers between the first electrode and the second electrode, wherein 1 or more of the organic layers include a compound represented by the chemical formula 1.
Effects of the invention
The compound described in the present specification is not only easy to produce, but also, when included as a material of an organic layer of an organic light-emitting device, can give an organic light-emitting device having a low driving voltage and excellent efficiency and life characteristics.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4.
1: substrate
2: anode
3: luminescent layer
4: cathode electrode
5: hole injection layer
6: hole transport layer
7: luminescent layer
8: electron transport layer
Detailed Description
The present specification will be described in more detail below.
The present specification provides a compound represented by the following chemical formula 1. The compound represented by the following chemical formula 1 is not only easy to manufacture, but also has 2 amine groups bound to specific positions of a five-ring fused heterocycle, compared to a core structure in which amine groups are substituted at different positions, and thus, when applied to an organic light emitting device, a device having excellent device efficiency, light emitting efficiency, and lifetime characteristics can be obtained.
In addition, according to one embodiment of the present specification, when the compound represented by the following chemical formula 1 is applied as a dopant of a light emitting layer in an organic light emitting device, energy transfer (energy transfer) with a host is easy, and thus a device having high light emitting efficiency and long life characteristics can be obtained. In the following chemical formula 1, a compound including 1 amine group or not including an amine group not only has an emission wavelength unsuitable for use as a dopant of an emission layer but also has very low emission Efficiency when applied to a device, and the compound of the following chemical formula 1 has a high Quantum Efficiency (QE) compared to a compound of chemical formula 1 in which a condensed position of a benzene ring to which an amine group is bonded is different, and thus has an advantage of showing high emission Efficiency when applied to a device.
In addition, the compound represented by the following chemical formula 1 includes 1 or more substituents other than hydrogen in the fused heterocyclic ring of the pentacyclic ring, thereby being electronically stable, and thus, when applied to a device, a device having excellent lifetime characteristics can be obtained, and when applied to a dopant of a light emitting layer, wavelength adjustment is easy, and thus, excellent light emitting efficiency and hue are exhibited.
[ chemical formula 1]
In the above-described chemical formula 1,
x is O, S or Si,
Ar1to Ar4Are the same or different from each other and are each independently hydrogen, deuterium, substitutedOr unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, or combine with each other with adjacent groups to form a substituted or unsubstituted carbazole,
R1to R8The same or different from each other, each independently is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, R1To R81 or more of (a) is deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
In the present specification, when a part of "includes" a certain component is referred to, unless otherwise stated, it means that the other component may be further included without excluding the other component.
In the present specification, when it is stated that a certain member is "on" another member, it includes not only a case where the certain member is in contact with the other member but also a case where the other member exists between the two members.
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.
In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, a cyano group (-CN), a nitro group, a hydroxyl group, a silyl group, a boryl group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, a cycloalkyl group, an aryl group, and a heterocyclic group, or a substituent in which 2 or more substituents among the above-exemplified substituents are linked, or does not have any substituent. The "substituent comprising 2 or more substituents bonded to each other" may be a phenylnaphthyl group. That is, a phenylnaphthyl group can be an aryl group, and can also be interpreted as a substitution of a phenyl group on the naphthyl group.
Examples of the above-mentioned substituent are described below, but the substituent is not limited thereto.
In the present specification, as examples of the halogen group, there are fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
In the present specification, the silyl group may be represented by-SiYaYbYcThe above-mentioned chemical formula is Ya、YbAnd YcMay each be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, an ethyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In this specification, the boron group may be represented BY-BYdYeThe above-mentioned chemical formula is YdAnd YeMay each be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl. The boron group is not limited to, but specifically, a dimethylboron group, a diethylboron group, a tert-butylmethylboron group, a diphenylboron group, a phenylboron group, and the like.
In the present specification, the number of carbon atoms of the alkyl group is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms.
Specific examples of the above alkyl group include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl and the like, and the above alkyl group may be straight or branched, and according to one example, propyl includes n-propyl and isopropyl, and butyl includes n-butyl, isobutyl and tert-butyl.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl (adamantane,
) And the like, but is not limited thereto.
In the present specification, the alkyl group of the alkoxy group can be applied to the above description about the alkyl group.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylene group, a triphenyl group, a perylene group,
Examples of the group include, but are not limited to, a fluorenyl group, a fluoranthenyl group, and a triphenylenyl group.
In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure.
When the fluorenyl group is substituted, the compound may be
Spirofluorene groups such as (spiroadamantane fluorene);
(9, 9-dimethylfluorenyl); and
and substituted fluorenyl groups such as (9, 9-diphenylfluorenyl) and the like. But is not limited thereto.
In the present specification, the heterocyclic group is a cyclic group containing 1 or more of N, O, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include, but are not limited to, pyridyl, quinolyl, thienyl, dibenzothienyl, furyl, dibenzofuryl, naphthobenzofuryl, carbazolyl, benzocarbazolyl, naphthobenzothienyl and the like.
In the present specification, the heteroaryl group may be aromatic, and the above description about the heterocyclic group may be applied.
In the present specification, the hydrocarbon ring may be an aromatic, aliphatic, or aromatic and aliphatic fused ring, the aromatic hydrocarbon ring may have the aromatic group described above in addition to the 2-valent ring, and the aliphatic hydrocarbon ring may have the cycloalkyl group described above in addition to the 2-valent ring.
According to an embodiment of the present specification, X is O, S or Si. When X is O, S or Si, since it is more thermally stable than a compound in which X is C, sublimation purification and device deposition are facilitated, and the life characteristics of the device can be improved.
According to an embodiment of the present disclosure, R is1To R8The same or different from each other, each independently is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl groupSubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclyl, R1To R81 or more of (a) is deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
According to another embodiment, R is as defined above1To R8The same or different from each other, each independently is hydrogen, deuterium, a substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms, R1To R81 or more of (a) is deuterium, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
In another embodiment, R is as defined above1To R8The same or different from each other, each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, R1To R81 or more of (a) are deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms.
According to another embodiment, R is as defined above1To R8The same or different from each other, each independently is hydrogen, deuterium, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclopentyl group, or a substituted or unsubstituted cyclohexyl group, R1To R81 or more of (a) is deuterium, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclopentyl group, or a substituted or unsubstituted cyclohexyl group.
In another embodiment, R is as defined above1To R8Are the same or different from each other, eachIndependently hydrogen, deuterium, ethyl, isopropyl, tert-butyl, cyclopentyl or cyclohexyl, R1To R81 or more of deuterium, ethyl, isopropyl, tert-butyl, cyclopentyl or cyclohexyl.
According to an embodiment of the present disclosure, R is1And R61 or more of them are deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and the others are hydrogen.
According to another embodiment, R is as defined above1And R61 or more of (A) is deuterium, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms, and the remainder is hydrogen.
According to another embodiment, R is as defined above1And R61 or more of them are deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, and the remainder are hydrogen.
According to another embodiment, R is as defined above1And R61 or more of deuterium, a substituted or unsubstituted ethyl group, a substituted or unsubstituted isopropyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclopentyl group, or a substituted or unsubstituted cyclohexyl group, and the balance of hydrogen.
According to another embodiment, R is as defined above1And R6More than 1 of the compounds are deuterium, ethyl, isopropyl, tert-butyl, cyclopentyl or cyclohexyl, and the rest are hydrogen.
In another embodiment, R is as defined above1Deuterium, ethyl, isopropyl, tert-butyl, cyclopentyl or cyclohexyl.
According to another embodiment, R is as defined above6Deuterium, ethyl, isopropyl, tert-butyl, cyclopentyl or cyclohexyl.
In another embodiment, R is as defined above1And R6Are the same or different from each otherEach independently is deuterium, ethyl, isopropyl, tert-butyl, cyclopentyl or cyclohexyl.
According to an embodiment of the present specification, Ar is1To Ar4Are the same or different from each other, each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 40 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 and containing O, S or N as a heteroatom, or a substituted or unsubstituted carbazole may be formed by bonding adjacent groups to each other.
In another embodiment, Ar is as described above1To Ar4Are the same or different from each other, each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 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 and containing O, S or N as a heteroatom, or a substituted or unsubstituted carbazole may be formed by bonding adjacent groups to each other.
In another embodiment, Ar is as described above1To Ar4The same or different from each other, each independently is an alkyl group of 1 to 20 carbon atoms; an aryl group having 6 to 60 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 20 carbon atoms, a trialkylsilyl group having 3 to 20 carbon atoms, and a cycloalkyl group having 3 to 30 carbon atoms; or a heterocyclic group of carbon number 2 to 60 containing O, S or N as a hetero atom, which is substituted or unsubstituted with 1 or more substituents selected from an alkyl group of carbon number 1 to 20, a cycloalkyl group of carbon number 3 to 30, and an aryl group of carbon number 6 to 30, which is substituted or unsubstituted with an alkyl group of carbon number 1 to 20, or a carbazole substituted or unsubstituted with an alkyl group of carbon number 1 to 20 is formed in combination with adjacent groups.
According to another embodiment, Ar is as described above1To Ar4The same or different from each other, each independently is a substituted or unsubstituted ethyl group, a substituted or unsubstituted phenyl groupSubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted spiroadamantanfluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl, or selected from Ar1And Ar2And Ar3And Ar41 or more of them are bonded to each other to form a substituted or unsubstituted carbazole. The above "substituted or unsubstituted" means that the substituted or unsubstituted group is substituted with 1 or more substituents selected from deuterium, a halogen group, a cyano group, a linear or branched alkyl group having 1 to 20 carbon atoms, a trialkylsilyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms.
In another embodiment, Ar is as described above1To Ar4The same or different from each other, each independently is a substituted or unsubstituted ethyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or the following chemical formula a, or combines with adjacent groups to each other to form a substituted or unsubstituted carbazole. The above "substituted or unsubstituted" means that the substituted or unsubstituted group is substituted with 1 or more substituents selected from deuterium, a halogen group, a cyano group, a linear or branched alkyl group having 1 to 20 carbon atoms, a trialkylsilyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms.
[ chemical formula A ]
In the above-mentioned chemical formula a,
R30is hydrogen, deuterium, halogen radicalA cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
n1 is an integer of 0 to 7, when n1 is 2 or more, 2 or more R30Are the same as or different from each other,
represents the position of the bond.
According to another embodiment, Ar is as described above1To Ar4Are the same or different from each other and are each independently an ethyl group; phenyl which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl; biphenyl substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl, and cyclohexyl; terphenyl group substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, cyano group, methyl group, isopropyl group, tert-butyl group, trimethylsilyl group, cyclopentyl group and cyclohexyl group; naphthyl substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl; phenanthryl substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl, and cyclohexyl; fluorenyl group substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen group, cyano group, methyl group, isopropyl group, tert-butyl group, trimethylsilyl group, cyclopentyl group and cyclohexyl group; benzofluorenyl group which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, cyano group, methyl group, isopropyl group, tert-butyl group, trimethylsilyl group, cyclopentyl group and cyclohexyl group; spiroadamantane fluorenyl substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, cyano, methyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl; selected from methyl, tert-butylDibenzofuranyl substituted or unsubstituted with 1 or more substituents selected from the group consisting of tert-butylphenyl, cyclopentyl and cyclohexyl; dibenzothienyl substituted or unsubstituted with 1 or more substituents selected from the group consisting of methyl, tert-butyl, tert-butylphenyl, cyclopentyl and cyclohexyl; or carbazolyl which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of methyl, t-butyl, t-butylphenyl, cyclopentyl and cyclohexyl, or Ar1And Ar2And Ar3And Ar41 or more of them are bonded to each other to form a carbazole substituted or unsubstituted with a butyl group.
According to an embodiment of the present specification, Ar is1To Ar4The same or different from each other, each independently selected from an alkyl group having 1 to 10 carbon atoms and the following structure, or combined with adjacent groups to form a substituted or unsubstituted carbazole.
In the above-described structure, the first and second electrodes,
w is O, S or NR103，
R101To R103The same or different from each other, each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
the above structure may be further substituted with 1 or more substituents selected from deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, and a substituted or unsubstituted aryl group,
in the above structure, represents the bonding position.
According to an embodiment of the present specification, the above structure may be further substituted with 1 or more substituents selected from deuterium, a halogen group, a cyano group, a trialkylsilyl group having 3 to 20 carbon atoms, a linear or branched alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, and an aryl group having 6 to 30 carbon atoms.
According to another embodiment, the above structure may be further substituted with 1 or more substituents selected from deuterium, a halogen group, a cyano group, a trimethylsilyl group, a methyl group, an isopropyl group, a tert-butyl group, a cyclopentyl group, and a cyclohexyl group.
According to an embodiment of the present disclosure, R is101To R103The same or different from each other, each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.
In another embodiment, R is as defined above101To R103The same or different from each other, each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
According to another embodiment, R is as defined above101To R103The same or different from each other, each independently is hydrogen, deuterium, a linear or branched alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.
In another embodiment, R is as defined above101To R103The same or different from each other, each independently is hydrogen, deuterium, methyl, isopropyl, tert-butyl, or phenyl substituted or unsubstituted with tert-butyl.
According to an embodiment of the present disclosure, the above-mentioned-N (Ar)1)(Ar2) and-N (Ar)3)(Ar4) Are the same as or different from each other, and are each independently represented by the following chemical formula 1-A or 1-B.
[ chemical formula 1-A ]
[ chemical formula 1-B ]
In the above chemical formulas 1-A and 1-B,
R11and R12The same or different from each other, each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
R20to R27The same or different from each other, each independently is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
in the above structure, represents the bonding position.
According to an embodiment of the present disclosure, R is11And R12Are the same or different from each other, each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 40 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 which contains O, S or N as a heteroatom.
In another embodiment, R is as defined above11And R12Are the same or different from each other, each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 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 which contains O, S or N as a heteroatom.
In another embodiment, R is as defined above11And R12The same or different from each other, each independently is an alkyl group of 1 to 20 carbon atoms; an aryl group having 3 to 60 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, a cyano group, an alkyl group having 1 to 20 carbon atoms, a trialkylsilyl group having 3 to 20 carbon atoms, and a cycloalkyl group having 3 to 30 carbon atoms; or by an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or an alkyl group having 1 to 20 carbon atomsA heterocyclic group having O, S or N as a hetero atom, which is substituted or unsubstituted with 1 or more substituents selected from among aryl groups having 6 to 30 carbon atoms and which is substituted or unsubstituted with a carbon atom number of 2 to 60.
According to another embodiment, R is as defined above11And R12The same or different from each other, each independently is a substituted or unsubstituted ethyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted spiroadamantane fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.
According to another embodiment, R is as defined above11And R12Are the same or different from each other and are each independently an ethyl group; phenyl which is substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl; biphenyl substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl, and cyclohexyl; (ii) terphenyl group substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, cyano group, methyl group, isopropyl group, tert-butyl group, trimethylsilyl group, cyclopentyl group and cyclohexyl group; naphthyl substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl; phenanthryl substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl, and cyclohexyl; fluorenyl group substituted or unsubstituted with 1 or more substituents selected from deuterium, halogen group, cyano group, methyl group, isopropyl group, tert-butyl group, trimethylsilyl group, cyclopentyl group and cyclohexyl group; is selected from deuterium, halogen radicals, cyano, methyl, isopropyl, tert-butyl, trimethylsilyl, cyclopentyl and cyclohexyl1 or more substituents among the above groups substituted or unsubstituted benzofluorenyl; spiroadamantane fluorenyl group substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, cyano group, methyl group, isopropyl group, tert-butyl group, trimethylsilyl group, cyclopentyl group and cyclohexyl group; dibenzofuranyl substituted or unsubstituted with 1 or more substituents selected from methyl, tert-butyl, tert-butylphenyl, cyclopentyl and cyclohexyl; dibenzothienyl substituted or unsubstituted with 1 or more substituents selected from the group consisting of methyl, tert-butyl, tert-butylphenyl, cyclopentyl and cyclohexyl; or a carbazolyl group which is unsubstituted or substituted with 1 or more substituents selected from the group consisting of a methyl group, a tert-butyl group, a tert-butylphenyl group, a cyclopentyl group and a cyclohexyl group.
According to an embodiment of the present disclosure, R is20To R27The alkyl groups are the same or different from each other, and each independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
According to another embodiment, R is as defined above20To R27The same or different from each other, each independently is hydrogen, or a substituted or unsubstituted tert-butyl group.
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,
X、R1to R8And Ar1To Ar3Is the same as defined in the above chemical formula 1,
R30and R30' the same or different from each other, each independently is hydrogen, deuterium, a halogen group, cyanogenA nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
n1 and n1 'are each an integer of 0 to 7, and when n1 and n1' are each 2 or more, structures in parentheses of 2 or more are the same as or different from each other.
According to an embodiment of the present disclosure, R is30And R30' is hydrogen.
In one embodiment of the present specification, n1 and n1' are each 0 or 1.
According to an embodiment of the present disclosure, the above-mentioned-N (Ar)1)(Ar2) and-N (Ar)3)(Ar4) The same or different from each other, and each independently represented by any one of the following structures.
In the above structure, represents the bonding position.
According to an embodiment of the present specification, the compound represented by the above chemical formula 1 is represented by any one of the following compounds.
The core structure of the compound represented by chemical formula 1 of the present specification may be produced as shown in the following reaction formulas 1 to 4, and amine groups may be bound to the following intermediates E-1 to E-4 through amination reaction known in the art. In addition, additional substituents may be incorporated using methods known in the art, and the type, position and number of substituents may be varied according to techniques known in the art.
< reaction formula 1>
1)
Mixing the intermediate A-1(56.1g, 175mmol) and 3-bromonaphthalene-2, 7-diol [ 3-bromonaphthalene-2, 7-diol](44g，184mmol)、K2CO3(145g, 1050mmol) was charged into 1, 4-bis
Alkane/water (4:1) (1500 mL). 2g of tetrakis (triphenylphosphine) palladium (TTP) was added under reflux with stirring, and then refluxed and stirred for 12 hours. At the end of the reaction, the temperature was lowered to normal temperature, and then extraction was performed with water and ethyl acetate and the organic layer was separated. For organic layersAfter treatment with anhydrous magnesium sulfate, the mixture was filtered and concentrated under reduced pressure. The solid was recrystallized from chloroform to give intermediate B-1. (43.2g, yield 70%, MS: [ M + H ]]+＝353)
2)
The intermediate B-1(43.5g, 135.6mmol) and CH were charged3SO2After OH (60mL), the mixture was stirred for 5 hours. After cooling to normal temperature, the reaction product was poured into water, the resulting solid was filtered, and the resulting solid was recrystallized from chloroform and ethanol, thereby producing the above intermediate C-1. (36.3g, yield 88%, MS: [ M + H ]]+＝335)
3)
The above intermediate C-1(36.3g, 108mmol) and isopropylboronic acid [ isopropylboronic acid ]](10.5g，119mmol)、K2CO3(74.6g, 540mmol) was charged into the 1, 4-bis
Alkane/water (4:1) (1500 mL). 2g of tetrakis (triphenylphosphine) palladium (TTP) and 2g of DPPF (1,1 '-bis (diphenylphosphino) ferrocene [1,1' -Ferrocendiylbis (diphenylp hosphine) ] were added under reflux with stirring]) After that, reflux and stirring were carried out for 12 hours. At the end of the reaction, the temperature was lowered to normal temperature, and then extracted with water and ethyl acetate and the organic layer was separated. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The solid was recrystallized from chloroform to give intermediate D-1. (19.6g, yield 53%, MS: [ M + H ]]+＝343)
4)
Intermediate D-1(19.6g, 57.3mmol) was put into tetrahydrofuran (1000mL), stirred for 1 hour, and then K was added2CO3(23.7g, 172mmol), 1,2,2,3,3,4,4, 4-nonafluorobutane-1-sulfonylfluoride [1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride](52g, 172mmol) and then stirred for a further 24 hours. At the end of the reaction, water and tetrahydrofuran were further added, and the organic layer was extracted and separated. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The solid was recrystallized from chloroform and ethanol to produce the intermediate E-1. (42.6g, yield 85%, MS: [ M + H ]]+＝915)
< reaction formula 2>
1)
Mixing the above compound A-1(56.1g, 175mmol) and 3-bromonaphthalene-2, 7-diol [ 3-bromonaphthalene-2, 7-diol](44g，184mmol)、K2CO3(145g, 1050mmol) was charged into 1, 4-bis
Alkane/water (4:1) (1500 mL). 2g of tetrakis (triphenylphosphine) palladium (TTP) was added under reflux with stirring, and then refluxed and stirred for 12 hours. At the end of the reaction, the temperature was lowered to normal temperature, and then extracted with water and ethyl acetate and the organic layer was separated. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The solid was recrystallized from chloroform to give intermediate B-2. (43.2g, yield 70%, MS: [ M + H ]]+＝353)
2)
The intermediate B-2(48.1g, 124.2mmol) and CH were charged3SO2After OH (70mL), the mixture was stirred for 5 hours. After cooling to normal temperature, the reaction product was poured into water, the resulting solid was filtered, and the resulting solid was recrystallized from chloroform and ethanol, thereby producing the above intermediate C-2. (37.1g, yield 81%, MS: [ M + H ]]+＝370)
3)
The above intermediate C-2(37.1g, 100.6mmol) and cyclohexylboronic acid [ Cyclohexylboronic acid ]](28.3g，221.3mmol)、K2CO3(111.2g, 804.8mmol) was charged into 1, 4-bis
Alkane/water (4:1) (1500 mL). 4g of tetrakis (triphenylphosphine) palladium (TTP) and 4g of DPPF (1,1 '-bis (diphenylphosphino) ferrocene [1,1' -Ferrocendiylbis (diphenylphosphine) ] are added under reflux with stirring]) After that, reflux and stirring were carried out for 12 hours. At the end of the reaction, the temperature was lowered to normal temperature, and then extracted with water and ethyl acetate and the organic layer was separated. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The solid was recrystallized from chloroform to give intermediate D-2. (25.7g, yield 55%, MS: [ M + H ]]+＝465)
4)
Intermediate D-2(25.7g, 55.3mmol) was put into tetrahydrofuran (1000mL), stirred for 1 hour, and then K was added2CO3(23g, 165.9mmol), 1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride [1,1,2,2,3,3,4,4, 4-fluorobutane-1-sulfonyl fluoride](52g, 172mmol) and then stirred for a further 24 hours. At the end of the reaction, water and tetrahydrofuran were further added, extraction was performed, and the organic layer was separated. Anhydrous sulfuric acid for organic layerAfter magnesium treatment, filtration and concentration under reduced pressure were carried out. The solid was recrystallized from chloroform and ethanol to produce the intermediate E-2. (49.6g, yield 90%, MS: [ M + H ]]+＝997)
< reaction formula 3>
1)
The intermediate C-2(37.1g, 100.6mmol) and 2,4,4,5,5-pentamethyl-1,3, 2-dioxolane [2,4,4,5,5-pentamethyl-1,3,2-dioxaborolane](31.4g，221.3mmol)、K2CO3(111.2g, 804.8mmol) was charged into 1, 4-bis
Alkane/water (4:1) (1500 mL). 4g of tetrakis (triphenylphosphine) palladium (TTP) and 4g of DPPF (1,1 '-bis (diphenylphosphino) ferrocene [1,1' -Ferrocendiylbis (diphenylphosphine) ] are added under reflux with stirring]) After that, reflux and stirring were carried out for 12 hours. At the end of the reaction, the temperature was lowered to normal temperature, and then extracted with water and ethyl acetate and the organic layer was separated. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The solid was recrystallized from chloroform to give intermediate D-3. (15.8g, yield 48%, MS: [ M + H ]]+＝329)
2)
Intermediate D-3(18.2g, 55.3mmol) was put into tetrahydrofuran (1000mL), stirred for 1 hour, and then K was added2CO3(23g, 165.9mmol), 1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride [1,1,2,2,3,3,4,4, 4-fluorobutane-1-sulfonyl fluoride](52g, 172mmol) and then stirred for a further 24 hours. At the end of the reaction, water and tetrahydrofuran were further added, extraction was performed, and the organic layer was separated. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Chloroform and ethyl for solidThe alcohol is recrystallized to produce the intermediate E-3. (44.9g, yield 91%, MS: [ M + H ]]+＝893)
< reaction formula 4>
1)
The intermediate C-2(37.1g, 100.6mmol) and 2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolan [2-isopropyl-4,4,5, 5-tetramethylol-1, 3,2-dioxaborolan](37.6g，221.3mmol)、K2CO3(111.2g, 804.8mmol) was charged into 1, 4-bis
Alkane/water (4:1) (1500 mL). 4g of tetrakis (triphenylphosphine) palladium (TTP) and 4g of DPPF (1,1 '-bis (diphenylphosphino) ferrocene [1,1' -Ferrocendiylbis (diphenylphosphin) were put into a vessel under reflux with stirring]) After that, reflux and stirring were carried out for 12 hours. At the end of the reaction, the temperature was lowered to normal temperature, and then extracted with water and ethyl acetate and the organic layer was separated. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The solid was recrystallized from chloroform to give intermediate D-4. (19.3g, yield 50%, MS: [ M + H ]]+＝385)
2)
Intermediate D-4(21.3g, 55.3mmol) was put into tetrahydrofuran (1000mL), stirred for 1 hour, and then K was added2CO3(23g, 165.9mmol), 1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride [1,1,2,2,3,3,4,4, 4-fluorobutane-1-sulfonyl fluoride](52g, 172mmol) and then stirred for a further 24 hours. At the end of the reaction, further addingWater and tetrahydrofuran were added, extraction was performed and the organic layer was separated. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The solid was recrystallized from chloroform and ethanol to produce the intermediate E-4. (44.6g, yield 85%, MS: [ M + H ]]+＝949)
Compounds having various energy band gaps can be synthesized by introducing various substituents into the compound represented by the above chemical formula 1. In the present specification, various substituents are introduced into the core structure having the above-described structure, whereby the HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) levels of the compound can be adjusted.
In the present specification, "energy level" refers to the magnitude of energy. Therefore, even when the energy level is expressed in the negative (-) direction from the vacuum level, the energy level is interpreted as referring to the absolute value of the energy value. For example, the HOMO (highest occupied molecular orbital) energy level refers to the distance from the vacuum level to the highest occupied molecular orbital. Further, the LUMO (lowest unoccupied molecular orbital) level refers to a distance from the vacuum level to the lowest unoccupied molecular orbital.
According to an embodiment of the present specification, the compound represented by the above chemical formula 1 may have a band gap energy (band gap energy) of 2.6eV to 2.9 eV. When the compound is applied as a blue dopant in a light-emitting layer of an organic light-emitting device, a device having high efficiency can be obtained by having an appropriate emission wavelength value. The band gap energy can be measured by the method of experimental example 1 described later.
Specifically, the band gap energy (band gap energy) value refers to the difference between the HOMO (highest occupied molecular orbital) energy level and the LUMO (lowest unoccupied molecular orbital) energy level, which can be measured as described below.
To determine the molecular structure of a chemical substance, the input structure is optimized using the Density Functional Theory (DFT). For the DFT calculation, the BPW91 algorithm (beck exchange function and per correlation function) and the DNP (double numerical basis of polarization function) basis set (basis set) are used. The BPW91 algorithm is disclosed in the paper "a.d. becke, phys.rev.a,38,3098 (1988)", and "j.p. perew and y.wang, phys.rev.b,45,13244 (1992)", the DNP basis set is disclosed in the paper "b.delley, j.chem. phys.,92,508 (1990)".
To perform the calculation by the density functional method, package (package) of "DMol 3" available from Biovia corporation may be used. When the optimum molecular structure is determined by the method given above, the energy level that can be occupied by electrons can be obtained as a result. The HOMO energy is an orbital energy of a highest energy level in a molecular orbital filled with electrons when energy of a neutral state is obtained, and the LUMO energy corresponds to an orbital energy of a lowest energy level in a molecular orbital not filled with electrons.
HOMO/LUMO calculation
Experimentally, the HOMO level is measured by an IP (Ionization Potential) value (the following formula-1) measured by an UPS (ultraviolet photoelectron spectroscopy) or the like, and the LUMO level is generally obtained by subtracting an Optical Gap (Optical Gap) from the HOMO level (the following formula-2).
[ formula-1 ]
HOMO ═ IP (ionization potential)
[ formula-2 ]
LUMO ═ IP-optical bandgap
Computationally, the HOMO and LUMO in the neutral state (theoretical state) together with the values actually measured in the corresponding experiment are provided, and the values are calculated by the following two methods.
Method 1) method of utilizing IP and optical energy gap
The IP and optical energy gap of the X molecule were determined by the following formulas-3 and-4 according to the calculation method in the experiment.
[ formula-3 ]
IP (ionization potential) ═ Ex+ Cation(s)-Ex Neutral property
[ formula-4 ]
Optical gapES1 S0-ES0 S0
In the above-mentioned formula-3,
refers to a structure in which the geometry is optimized to be cationic (cation), anionic (anion) or neutral (neutral), and the charge (charge) is 0, X+Or X-The energy of (a). That is, the electron affinity is a difference from the most stable structure energy of the neutral structure to the most stable energy of the anion, and may be energy released when one electron is added in the neutral state.
In the above formula-4, S0 denotes a singlet state of a ground state (ground state), S1 denotes a singlet state of a first excited state (exit state), ES1 S0Is the difference between the singlet energy of the ground state and the singlet energy of the first excited state, ES0 S0Refers to the energy difference within the singlet state of the ground state. At this time, ES0 S0Refers to the energy difference caused by the change in geometry (geometry) inside the singlet state of the ground state. Further, assuming that the structures of S0 and S1 do not change much, the energy of absorption (absorbance) is similar to the fluorescence (fluorescence) value. Thus, the optical bandgap corresponds to the S0-S1 bandgap (gap). The energies of the ground state and the excited state are based on values calculated by a density functional.
Method 2) method of utilizing Solid state (Solid state) IP and optical energy gap
Since the layer is in a non-monomolecular solid state (solid state), the effect at that time can be corrected as shown in the following formula-5 in consideration of the molecular shape or the like to obtain a HOMO calculation (HOMO calc.) value, and the LUMO level can be obtained by substituting the HOMO calculation value into the IP value of the formula-2. But transition metal (transition metal) cannot be calculated.
[ formula-5 ]
HOMO calculation IP + delta (solid/molecule)
In the above formula-5, Δ (solid/molecule) means the difference in energy between a monomolecular state (Molecular state) and a solid state (solid state), and the Asphericity (acidity), Radius of gyration (Radius of gyration), Molecular weight (Molecular weight), and the like may have an influence.
An organic light-emitting device according to the present specification is characterized by comprising: the organic light emitting device includes a first electrode, a second electrode, and 1 or more organic layers between the first electrode and the second electrode, wherein 1 or more of the organic layers include a compound represented by the above-mentioned chemical formula 1.
The organic light emitting device of the present specification can be manufactured by using a general method and material for manufacturing an organic light emitting device, in addition to forming one or more organic layers using the compound represented by the above chemical formula 1.
The organic layer including the compound represented by chemical formula 1 may be formed not only by a vacuum evaporation method but also by a solution coating method in the manufacture of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
The organic layer of the organic light-emitting device in the present specification may have a single-layer structure, or may have a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light-emitting device of the present specification may have a structure including a hole injection layer, a hole transport layer, a layer which performs hole transport and hole injection simultaneously, an electron suppression layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer which performs electron transport and electron injection simultaneously, or the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller or greater number of organic layers may be included.
In the organic light emitting device of the present specification, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include the compound represented by the above chemical formula 1.
In the organic light emitting device of the present specification, the organic layer may include a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer may include the compound represented by the above chemical formula 1.
In the organic light emitting device of the present specification, the organic layer includes a light emitting layer including the compound represented by the above chemical formula 1.
According to another embodiment, the organic layer includes a light emitting layer, the light emitting layer includes the compound represented by the chemical formula 1 as a dopant of the light emitting layer, and the dopant has a maximum light emitting wavelength of 430nm to 470 nm. The compound of the present invention contains 2 amine groups and thus has the maximum light emission wavelength in the above range, but the compound containing 1 amine group has the maximum light emission wavelength in the range of about 410nm to 430 nm.
The light emitting layer may further include a host having a maximum light emitting wavelength of 400nm to 440nm, and the compound of the present invention including 2 amine groups easily performs energy transfer (energy transfer) in the relationship with the host to have excellent efficiency, but the compound including 1 amine group does not smoothly perform energy transfer in the relationship with the host, and thus the efficiency of the device is lowered. The maximum luminescence wavelength can be determined by dissolving the compound to be measured at 1x10 in toluene solution-5M/L was diluted and measured at room temperature. The maximum emission peak of the above-mentioned compound was measured by FP-8600 of JASCO corporation, the emission spectrum at an excitation (excitation) wavelength of 300nm was 430nm to 470nm, and HPLC grade anhydrous Toluene (HPLC grade anhydrous Toluene) was used as the solvent.
According to an embodiment of the present specification, the compound represented by the above chemical formula 1 is included in a light emitting layer of an organic light emitting device as a blue dopant.
According to another embodiment, the compound represented by the above chemical formula 1 is included in a light emitting layer of an organic light emitting device as a Thermal Activated Delayed Fluorescence (TADF) device fluorescent dopant. In this case, the compound is thermally activated to delay fluorescence in the light-emitting layer. The thermally activated delayed fluorescence is a fluorescence emission caused by inducing reverse intersystem crossing from a triplet excited state to a singlet excited state, and moving excitons in the singlet excited state to a ground state, and a high-efficiency organic light-emitting device can be obtained.
According to an embodiment of the present invention, the compound represented by the above chemical formula 1 is included as a dopant of the light emitting layer, and a host of an anthracene compound having the following structure may be included, but the present invention is not limited thereto.
In another embodiment, the organic layer includes a light emitting layer, and the light emitting layer includes a compound represented by the above chemical formula 1 as a dopant of the light emitting layer, and further includes a fluorescent host or a phosphorescent host, and may include other organic compounds, metals, or metal compounds as a dopant.
As another example, the organic layer includes a light emitting layer, and the light emitting layer includes a compound represented by the above chemical formula 1 as a dopant of the light emitting layer, and further includes a fluorescent host or a phosphorescent host, and may be used together with an iridium (Ir) dopant.
According to another embodiment, the organic layer includes a light emitting layer, and the light emitting layer may include the compound represented by the chemical formula 1 as a host of the light emitting layer.
As another example, the organic layer includes a light emitting layer, and the light emitting layer includes the compound represented by the chemical formula 1 as a host of the light emitting layer and may further include a dopant.
The light emitting layer includes a host and a dopant, and the dopant may be included in an amount of 1 to 20 parts by weight, and more preferably 1 to 5 parts by weight, based on 100 parts by weight of the host.
In one embodiment of the present disclosure, 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.
For example, the organic light emitting device may have a stacked structure as shown below, but is not limited thereto.
(1) Anode/hole transport layer/light emitting layer/cathode
(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode
(3) Anode/hole transport layer/light emitting layer/electron transport layer/cathode
(4) Anode/hole transport layer/luminescent layer/electron transport layer/electron injection layer/cathode
(5) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode
(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(7) Anode/hole transport layer/electron inhibiting layer/light emitting layer/electron transport layer/cathode
(8) Anode/hole transport layer/electron inhibiting layer/light emitting layer/electron transport layer/electron injection layer/cathode
(9) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode
(10) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode
(11) Anode/hole transport layer/light-emitting layer/hole inhibiting layer/electron transport layer/cathode
(12) Anode/hole transport layer/light-emitting layer/hole inhibiting layer/electron transport layer/electron injection layer/cathode
(13) Anode/hole injection layer/hole transport layer/light-emitting layer/hole inhibiting layer/electron transport layer/cathode
(14) Anode/hole injection layer/hole transport layer/light-emitting layer/hole inhibiting layer/electron transport layer/electron injection layer/cathode
The structure of the organic light emitting device of the present specification may have the structure shown in fig. 1 and 2, but is not limited thereto.
Fig. 1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above light emitting layer 3.
Fig. 2 illustrates a structure of an organic light-emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in 1 or more layers among the above hole injection layer 5, hole transport layer 6, light emitting layer 7, and electron transport layer 8.
For example, the organic light emitting device according to the present specification may be manufactured as follows: the organic el display device is manufactured by forming an anode by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate by a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron suppression layer, an electron transport layer, and an electron injection layer on the anode, and depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic electronic device.
The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a layer that performs both electron injection and electron transport, an electron suppression layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that performs both electron injection and electron transport, a hole suppression layer, and the like, but is not limited thereto and may have a single-layer structure. The organic layer can be produced as a smaller number of layers by a solvent process (solvent process) other than the vapor deposition method, for example, spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method, using various polymer materials.
Each layer constituting the organic light emitting device described below may be formed of 1 layer or 2 or more layers, and the 2 or more layers may be formed of the same substance or may be formed of substances different from each other.
The anode is an electrode for injecting holes, and the anode material is preferably a work function so that holes can be injected into the organic layer smoothlyLarge substances. 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; metal oxides such as Zinc Oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO-Al or SnO2A 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 is an electrode for injecting electrons, and a substance having a small work function is generally preferable as a cathode substance 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 LiO2And a multilayer structure material such as Al, but not limited thereto.
The hole injection layer is a layer that functions to smoothly inject holes from the anode into the light-emitting layer, and the hole injection substance is a substance that can inject holes from the anode well at a low voltage, and preferably, the HOMO (highest occupied molecular orbital) of the hole injection substance is interposed 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 (porphyrine), 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 can function to smooth the transport of holes. The hole-transporting substance is a substance capable of receiving holes from the anode or the hole-injecting layer and transferring the holes to the light-emitting layer, and is preferably a substance 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.
An electron inhibiting layer may be provided between the hole transport layer and the light emitting layer. The electron-suppressing layer may be made of a material known in the art.
The light-emitting layer may emit red, green or blue light, and may be formed of a phosphorescent substance or a fluorescent substance. The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As an example, there is an 8-hydroxyquinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is
Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.
As a host material of the light-emitting layer, there are aromatic fused ring derivatives, heterocyclic ring-containing compounds, and the like. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene derivatives, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds: (
) And pyrimidine derivatives, but are not limited thereto.
When the light-emitting layer emits red light, as a light-emitting dopant, a phosphorescent material such as piqir (acac) (bis (1-phenylisoquinoline) acetylacetonatoiridium, bis (1-phenylisoquinoline) acetylacetonatoiridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonatoiridium, bis (1-phenylquinoline) acetylacetonatoiridium), PQIr (tris (1-phenylquinoline) iridium, tris (1-phenylquinoline) iridium), PtOEP (octylporphyrin, platinum octaethylporphyrin), or Alq (r) may be used3(tris (8-hydroxyquinolino) aluminum), etc., but is not limited thereto. When the luminescent layer emits greenIn light, Ir (ppy) can be used as a light-emitting dopant3Phosphorescent substances such as fac tris (2-phenylpyridine) iridium, and Alq tris (2-phenylpyridine) iridium3(tris (8-hydroxyquinolino) aluminum), etc., but is not limited thereto. When the light-emitting layer emits blue light, (4, 6-F) may be used as the light-emitting dopant2ppy)2Examples of the fluorescent substance include phosphorescent substances such as Irpic and fluorescent substances such as spiro-DPVBi (spiro-DPVBi), spiro-6P (spiro-6P), Distyrylbenzene (DSB), Distyrylarylene (DSA), PFO-based polymers, and PPV-based polymers, but the fluorescent substances are not limited thereto.
A hole-inhibiting layer may be provided between the electron-transporting layer and the light-emitting layer, and any material known in the art may be used.
The electron transport layer can play a role in smoothly transporting electrons. The electron transport material is a material capable of injecting electrons from the cathode and transferring the electrons to the light-emitting layer, and is preferably a material having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq3The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto.
The electron injection layer can perform a function of smoothly injecting electrons. As the electron-injecting substance, the following compounds are preferred: a compound having an ability to transport electrons, having an effect of injecting electrons from a cathode, having an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and having an excellent thin-film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives thereofHowever, the present invention is 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 specification 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
< Synthesis example >
Synthesis example 1.
Intermediate E-3(13.4g, 15.0mmol) and intermediate 1(6.8g, 30.1mmol) were placed in xylene (200 mL). NatBuO (4.3g) and bis (tri-tert-butylphosphino) palladium [ BTP ] were added](0.2g), stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized from ethyl acetate 3 times to produce the above-mentioned compound 1. (4.7g, yield 42%, MS: [ M + H ]]+＝744)
Synthesis example 2.
Intermediate E-3(13.4g, 15.0mmol) and intermediate 2(8.5g, 30.1mmol) were placed in xylene (200 mL). NatBuO (4.3g) and BTP (0.2g) were charged, stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized from ethyl acetate 3 times to produce the above-mentioned compound 2. (6.4g, yield 50%, MS: [ M + H ]]+＝856)
Synthesis example 3.
Intermediate E-4(14.2g, 15.0mmol) and intermediate 3(8.6g, 30.1mmol) were placed in xylene (200 mL). NatBuO (4.3g) and BTP (0.2g) were charged, stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized from ethyl acetate 3 times to produce the above-mentioned compound 3. (7.0g, yield 51%, MS: [ M + H ]]+＝920)
Synthesis example 4.
Intermediate E-3(13.4g, 15.0mmol) and intermediate 4(8.7g, 30.1mmol) were placed in xylene (200 mL). NatBuO (4.3g) and BTP (0.2g) were charged, stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized from ethyl acetate 3 times to produce the above-mentioned compound 4. (7.2g, yield 55%, MS: [ M + H ]]+＝874)
Synthesis example 5.
Intermediate E-1(15.0g, 17.2mmol) and intermediate 5(6.4g, 34.3mmol) were placed in xylene (200 mL). NatBuO (5.0g) and BTP (0.2g) were charged, stirred and refluxed for 5 hours. After cooling to room temperature, the reaction mixture was filtered, and the resulting solid was recrystallized from ethyl acetate 3 times to produce the above-mentioned compound 5. (5.9g, yield 50%, MS: [ M + H ]]+＝681)
Synthesis example 6.
Intermediate E-2(15.0g, 15.0mmol) and intermediate 6(5.8g, 30.1mmol) were placed in xylene (200 mL). NatBuO (4.3g) and BTP (0.2g) were charged, stirred and refluxed for 5 hours. After cooling to room temperature, the reaction mixture was filtered, and the resulting solid was recrystallized from ethyl acetate 3 times to produce the above-mentioned compound 6. (7.1g, yield 58%, MS: [ M + H ]]+＝818)
In the above synthesis examples, the synthesis processes of the compounds 1 to 6 are exemplified, but intermediates having various types of substituents bonded thereto may be synthesized by reactions known in the art, or compounds other than the above compounds 1 to 6 may be synthesized using commercially available intermediates.
< Experimental example 1>
The simulation results of compound 1, compound 1-1, comparative compound 1 and comparative compound 2 measured using the apparatus and conditions described below are shown in table 4 below. Based on the results of table 4 below, it can be predicted that the band gap energy (band gap energy) of compound 1 and compound 1-1 has a value suitable for use as a blue dopant of the light emitting layer, but the light emitting wavelength ranges of comparative compounds 1 and 2, in which the band gap energy exceeds 2.9eV, are not suitable for use as a blue dopant, and thus the light emitting efficiency will be very low.
DFT calculation (DFT calculation): BPW91/DND (DMol3)
Geometric optimization (Geometry optimization): single point energy calculation (Single point energy calculation)
UV calculation (UV calculation): ZINDO (G03)
Band gap calculation (Band gap calculation): TD (G03)
Solid state IP calculation (Solid state IP calculation): QSPR (Adriana )
[ Table 4]
< Experimental example 2>
Example 1.
ITO (indium tin oxide) is added
The glass substrate (corning 7059 glass) coated with a thin film was put in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent used was a product of Fisher Co, and the distilled water used was distilled water obtained by twice filtering with a Filter (Filter) manufactured by Millipore Co. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, ultrasonic washing was performed in the order of solvents of isopropyl alcohol, acetone, and methanol, and then dried.
On the ITO transparent electrode thus prepared, HAT described below was added
The hole injection layer is formed by thermal vacuum deposition. On the hole injection layer, as a hole transport layer, the following HT-A was vacuum-deposited
The following HT-B was vapor-deposited
As a light emitting layer, the following compound 1 as a dopant was doped with 4 wt% to the following H-A as a host, and
the thickness is vacuum evaporated. Then, ET-A and Liq were deposited at a ratio of 1:1
On it, the vapor deposition is performed in sequence
Thickness doped with 10 wt% silver (A)g) Magnesium (Mg) and
the cathode is formed of aluminum in a thickness, thereby fabricating an organic light emitting device.
In the above process, the evaporation speed of the organic material is maintained
Maintenance of LiF
Deposition rate of (3), aluminum maintenance
To
The deposition rate of (3).
Examples 2 to 21 and comparative examples 1 to 9
An organic light-emitting device was produced in the same manner as in example 1, except that in example 1, compounds described in tables 1 to 3 below were used instead of H — a as the host of the light-emitting layer, and that in example 1, compounds described in tables 1 to 3 below were used instead of compound 1 as the dopant of the light-emitting layer.
For the organic light emitting devices of the above examples 1 to 21 and comparative examples 1 to 9, at 10mA/cm2The driving voltage and the luminous efficiency were measured at a current density of 20mA/cm2The time (LT95) was measured at a current density of 95% relative to the initial luminance. The results are shown in tables 1 to 3 below.
[ Table 1]
[ Table 2]
[ Table 3]
Based on the above tables 1 to 3, it can be confirmed that the devices of examples 1 to 21 of the present application have a low driving voltage, and are excellent in efficiency and life, as compared to comparative examples 1 to 9.
Specifically, each of comparative examples 1 and 3 to 7 uses the compound D-1, the compound D-3, the compound D-4, the compound D-5, or the compound D-6, in which pyrene, naphthobenzofuran, fluorene, dibenzofluorene, or dinaphthofuran is bonded between 2 amine groups, as a dopant of the light-emitting layer, but it was confirmed that the performance was decreased as compared with the device using the compound of the present application.
In comparative examples 2 and 8, the compound D-2 having a different amino group binding site from that of the compound of the present application was used, and it was confirmed that the device performance was lowered and, in particular, the device life was extremely low as compared with the device using the compound of the present application.
In comparative example 9, in which compound D-7 was used, the core structure and the amino group were bonded at the same position as the compound of the present application, but no substituent other than the amino group was bonded to dinaphthofuran as the core structure, and it was confirmed that the driving voltage was higher and the efficiency and the lifetime were reduced as compared with the device using the compound of the present application.
Claims (13)
1. A compound represented by the following chemical formula 1:
chemical formula 1
Wherein, in the chemical formula 1,
x is O, S or Si,
Ar1to Ar4Are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or combine with each other with adjacent groups to form a substituted or unsubstituted carbazole, and
R1to R8The same or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and R is1To R81 or more of (a) is deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.
2. The compound of claim 1, wherein said-N (Ar)1)(Ar2) and-N (Ar)3)(Ar4) Are the same as or different from each other, and are each independently represented by the following chemical formula 1-A or 1-B:
chemical formula 1-A
Chemical formula 1-B
Wherein, in the chemical formulas 1-A and 1-B,
R11and R12The same or different from each other, and each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
R20to R27The same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and
wherein in said structure, represents the position of the bond.
3. The compound of claim 1, wherein said Ar is1To Ar4The same or different from each other, and each independently is a substituted or unsubstituted ethyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or the following formula A, or combines with adjacent groups to each other to form a substituted or unsubstituted carbazole,
chemical formula A
Wherein, in the chemical formula A,
R30is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,
n1 is an integer of 0 to 7, and when n1 is 2 or more, 2 or more R30Are the same as or different from each other, and
represents the position of the bond.
4. 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
Wherein, in the chemical formulas 1-1 and 1-2,
X、R1to R8And Ar1To Ar3Is the same as that in said chemical formula 1,
R30and R30' may be the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boryl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, and
n1 and n1 'are each an integer of 0 to 7, and when n1 and n1' are each 2 or more, the structures in parentheses of 2 or more are the same as or different from each other.
5. The compound of claim 1, wherein said Ar is1To Ar4The same or different from each other and each independently selected from an alkyl group having 1 to 10 carbon atoms and the following structure, or combined with adjacent groups to form a substituted or unsubstituted carbazole,
wherein, in the structure described above,
w is O, S or NR103，
R101To R103Are the same or different from each other and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
the structure may be further substituted with 1 or more substituents selected from deuterium, a halogen group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, and a substituted or unsubstituted aryl group,
wherein in said structure, represents the position of the bond.
6. The compound of claim 1, wherein said-N (Ar)1)(Ar2) and-N (Ar)3)(Ar4) Are the same or different from each other, and are each independently represented by any one of the following structures:
wherein in said structure, represents the position of the bond.
7. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is represented by any one of the following compounds:
8. an organic light emitting device, comprising: a first electrode, a second electrode, and an organic layer having 1 or more layers between the first electrode and the second electrode, wherein 1 or more layers of the organic layer contain the compound according to any one of claims 1 to 7.
9. The organic light emitting device according to claim 8, wherein the organic layer comprises a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer contains the compound.
10. The organic light emitting device of claim 8, wherein the organic layer comprises an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer comprises the compound.
11. The organic light emitting device of claim 8, wherein the organic layer comprises a light emitting layer and the light emitting layer comprises the compound.
12. The organic light-emitting device according to claim 8, wherein the organic layer comprises a light-emitting layer containing the compound as a dopant of the light-emitting layer, and the dopant has a maximum light-emitting wavelength of 430nm to 470 nm.
13. The organic light-emitting device according to claim 12, wherein the light-emitting layer further comprises a host having a maximum light-emitting wavelength of 400nm to 440 nm.
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