CN117460728A - Novel compound and organic light emitting device comprising the same - Google Patents

Novel compound and organic light emitting device comprising the same Download PDF

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Publication number
CN117460728A
CN117460728A CN202280040511.9A CN202280040511A CN117460728A CN 117460728 A CN117460728 A CN 117460728A CN 202280040511 A CN202280040511 A CN 202280040511A CN 117460728 A CN117460728 A CN 117460728A
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substituted
compound
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徐尚德
金旼俊
金永锡
金东熙
吴重锡
李多情
李东勋
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LG Chem Ltd
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LG Chem Ltd
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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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H—ELECTRICITY
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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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers

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Abstract

The present invention provides a novel compound and an organic light emitting device using the same.

Description

Novel compound and organic light emitting device comprising the same
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2021-0075599, 6/10/2021, the entire contents of the disclosure of which are incorporated as part of the present specification.
The present invention relates to novel compounds and organic light emitting devices comprising 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 has a wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons transition to the ground state again.
As for the organic matter used for the organic light emitting device as described above, development of new materials is continuously demanded.
Prior art literature
Patent literature
(patent document 0001) Korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Technical problem
The present invention relates to novel compounds and organic light emitters comprising the same.
Solution to the problem
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-mentioned chemical formula 1,
two adjacent R 1 Are combined with each other to form a benzene ring, and the benzene ring is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group is substituted and the substituted heteroaryl group is substituted,
the rest R 1 Is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
R 2 is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
R a 、R b and R is c Each independently is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
n1 and n2 are each an integer of 0 to 3,
n3 is an integer of 0 to 4,
L 1 and L 2 Each independently is a single bond; substituted or unsubstituted C 6-60 Arylene groups; or (b)Substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroarylene group,
Ar 1 and Ar is a group 2 One of them is represented by the following chemical formula 2, and the others are substituted or unsubstituted C 6-60 An aryl group,
[ chemical formula 2]
In the above-mentioned chemical formula 2,
x is O or S, and the X is O or S,
R d each independently is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
n4 is an integer from 0 to 7.
In addition, the present invention provides an organic light emitting device, wherein comprising: a first electrode, a second electrode provided opposite to the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
Effects of the invention
The compound represented by the above chemical formula 1 may be used as a material of an organic layer of an organic light emitting device in which improvement of efficiency, lower driving voltage, and/or improvement of lifetime characteristics may be achieved. In particular, the compound represented by the above chemical formula 1 may be used as a material for hole injection, hole transport, hole injection and transport, electron blocking, light emission, hole blocking, electron transport, electron injection, or electron injection and transport.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device constituted by 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 constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, an electron injection and transport layer 8, and a cathode 4.
Detailed Description
In the following, the invention will be described in more detail in order to aid understanding thereof.
In the present description of the invention,represents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means that it is selected from deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; alkylthio groupArylthio->Alkylsulfonyl->Arylsulfonyl->A silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; or a substituent comprising N, O and 1 or more substituents in the heterocyclic group containing 1 or more of S atoms is substituted or unsubstituted, or a substituent bonded by 2 or more substituents in the above-exemplified substituents is substituted or unsubstituted. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, in the ester group, oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. According to another embodiment, the above alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but the present invention is not limited thereto.
In the present specification, the 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 phenyl, biphenyl, and terphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, and the like,A group, a fluorenyl group, etc., but is not limited thereto.
In this specification, a fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. In the case where the above fluorenyl group is substituted, it may beEtc. However, the present invention is not limited thereto.
In this specification, the heterocyclic group is a heterocyclic group containing 1 or more of O, N, si and S as a hetero element, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo- >Oxazolyl, benzimidazolyl, benzothiazolyl, and benzeneCarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthroline (phenanthrinyl), and iso +.>Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present specification, the aryl groups in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group are the same as those exemplified for the aryl groups described above. In the present specification, the alkyl group in the aralkyl group, alkylaryl group, and alkylamino group is the same as the above-mentioned alkyl group. In this specification, the heteroaryl group in the heteroaryl amine may be as described above with respect to the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-described examples of alkenyl groups. In this specification, arylene is a 2-valent group, and the above description of aryl can be applied in addition to this. In this specification, the heteroarylene group is a 2-valent group, and the above description of the heterocyclic group can be applied thereto. In this specification, the hydrocarbon ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the aryl group or cycloalkyl group can be applied. In this specification, a heterocyclic ring is not a 1-valent group but a combination of 2 substituents, and the above description of a heterocyclic group can be applied thereto.
The present invention provides a compound represented by the above chemical formula 1.
The compound represented by the above chemical formula 1 can improve the characteristics of an organic light emitting device using the same by bonding a heterocyclic ring containing O or S to nitrogen atoms of a benzocarbazole ring and a carbazole ring in a parent nucleus structure in which a carbazole group is bonded to a specific position of a benzocarbazole group.
In particular, the compound represented by the above chemical formula 1 has a structure including dibenzofuran or dibenzothiophene attached to a nitrogen atom of a carbazole or benzocarbazole structure, thereby facilitating hole transport and injection, and can block electron migration because there is no unit that attracts electrons.
In addition, in the substituent of chemical formula 1, adjacentR of (2) 1 The benzocarbazole formed by fusing to each other at a specific position of (a) has an appropriate HOMO level and triplet energy as a p-type host, and thus has a structure in which energy is smoothly transferred to the red dopant by mixing with other hosts.
Therefore, compared with a case where an electron blocking layer which is in contact with a light emitting layer to inject holes or a host which transfers holes in the light emitting layer is applied, a better light emitting characteristic can be exhibited, whereby quantum efficiency and lifetime can be improved together with low voltage characteristics.
Specifically, the present invention provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
two adjacent R 1 Are combined with each other to form a benzene ring, and the benzene ring is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group is substituted and the substituted heteroaryl group is substituted,
the rest R 1 Is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
R 2 is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
R a 、R b and R is c Each independently is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
n1 and n2 are each an integer of 0 to 3,
n3 is an integer of 0 to 4,
L 1 and L 2 Each independently is a single bond, or a substituted or unsubstituted C 6-60 An arylene group,
Ar 1 and Ar is a group 2 One of them is represented by the following chemical formula 2, and the others are substituted or unsubstituted C 6-60 An aryl group,
[ chemical formula 2]
In the above-mentioned chemical formula 2,
x is O or S, and the X is O or S,
R d each independently is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
n4 is an integer from 0 to 7.
More specifically, in the above chemical formula 1, the compound represented by the above chemical formula 1 may be represented by the following chemical formula 1-1 or 1-2 according to the specific position of the naphthalene ring bonded to the benzocarbazole group:
[ chemical formula 1-1]
[ chemical formulas 1-2]
In the above chemical formulas 1-1 and 1-2,
R a 、R b 、R c 、L 1 、L 2 、Ar 1 and Ar is a group 2 As defined in claim 1,
each R' is independently hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted inclusionC selected from any one or more of N, O and S heteroatoms 2-60 A heteroaryl group, which is a group,
n' is an integer from 0 to 6.
In addition, the compound represented by the above chemical formula 1 may be represented by any one of the following chemical formulas 1-3 to 1-10:
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
[ chemical formulas 1-7]
[ chemical formulas 1-8]
[ chemical formulas 1-9]
[ chemical formulas 1-10]
In the above chemical formulas 1-3 to 1-10,
R a 、R b 、R c 、L 1 、L 2 、Ar 1 、Ar 2 r 'and n' are as defined in the above chemical formulas 1-1 and 1-2.
More specifically, the compound represented by the above chemical formula 1 may be represented by the following chemical formulas 1 to 11 or 1 to 12:
[ chemical formulas 1-11]
[ chemical formulas 1-12]
In the above chemical formulas 1 to 11 and 1 to 12,
R a 、R b 、R c 、L 1 、L 2 、Ar 1 、Ar 2 r 'and n' are as defined in the above chemical formulas 1-1 and 1-2.
In addition, the compound represented by the above chemical formula 1 may be represented by any one of the following chemical formulas 1-11a to 1-11c and chemical formulas 1-12a to 1-12 c:
[ chemical formulas 1-11a ]
[ chemical formulas 1-11b ]
[ chemical formulas 1-11c ]
[ chemical formulas 1-12a ]
[ chemical formulas 1-12b ]
[ chemical formulas 1-12c ]
In the above chemical formulas 1-11a to 1-11c and chemical formulas 1-12a to 1-12c,
L 1 、L 2 、Ar 1 and Ar is a group 2 As defined in the above chemical formulas 1-1 and 1-2,
R e each independently of the other is hydrogen or deuterium,
R f each independently is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 Heteroaryl groups.
On the other hand, in the above chemical formula 1, specifically, two adjacent R 1 Are combined with each other to form a benzene ring, which may be hydrogen; deuterium; substituted or unsubstituted C 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-12 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 5-30 Heteroaryl, or C 8-20 Heteroaryl, or C 12-18 Heteroaryl substitution.
In addition, R 1 Wherein benzene rings are not formedThe remaining one may be hydrogen; deuterium; substituted or unsubstituted C 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-12 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 5-30 Heteroaryl, or C 8-20 Heteroaryl, or C 12-18 Heteroaryl groups.
Preferably, in the above chemical formula 1, two adjacent R' s 1 Combine with each other to form a benzene ring substituted by hydrogen or deuterium, the remainder R 1 May be hydrogen or deuterium.
On the other hand, in the above chemical formula 1, specifically, R 2 May be hydrogen; deuterium; substituted or unsubstituted C 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-12 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 5-30 Heteroaryl, or C 8-20 Heteroaryl, or C 12-18 Heteroaryl groups.
Preferably, in the above chemical formula 1, R 2 May be hydrogen, deuterium, phenyl, or phenyl substituted with deuterium.
On the other hand, in the above chemical formula 1 and chemical formulas 1-1 to 1-12, specifically, R a 、R b And R is c Each may be hydrogen; deuterium; substituted or unsubstituted C 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-12 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 5-30 Heteroaryl, or C 8-20 Heteroaryl, or C 12-18 Heteroaryl groups.
Preferably, in the above chemical formula 1 and chemical formulas 1-1 and 1-12, R a 、R b And R is c Each may be hydrogen, deuterium, phenyl or phenyl substituted with deuterium.
In addition, n1 and n2 may each be an integer of 0 to 2, or 0 or 1.
In addition, n3 may be an integer of 0 to 3, an integer of 0 to 2, or 0 or 1.
Another partyIn the above chemical formulas 1-1 to 1-12, specifically, each of R' may be hydrogen; deuterium; substituted or unsubstituted C 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-12 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 5-30 Heteroaryl, or C 8-20 Heteroaryl, or C 12-18 Heteroaryl groups.
Preferably, in the above chemical formulas 1-1 to 1-12, each R' may be hydrogen, deuterium, phenyl, or phenyl substituted with deuterium.
In addition, in the above chemical formulas 1-1 to 1-12, n' may be an integer of 0 to 5, or an integer of 0 or 4, or an integer of 0 to 3, an integer of 0 to 2, or 0 or 1.
On the other hand, in the above chemical formula 1 and chemical formulas 1-1 to 1-12, chemical formulas 1-11a to 1-11c and chemical formulas 1-12a to 1-12c, specifically, L 1 And L 2 Each may be a single bond; or substituted or unsubstituted C 6-30 Arylene group, or C 6-28 Arylene group, or C 6-25 Arylene group, or C 6-12 Arylene groups.
More specifically, L 1 And L 2 Each may be a single bond; or phenylene, biphenylene, terphenylene, tetra-biphenylene or naphthylene.
As an example, L 1 And L 2 Each may be a single bond or may be represented by any one selected from the following groups.
Preferably L 1 And L 2 Each may be a single bond, or phenylene or naphthylene.
On the other hand, in the above chemical formula 1 and chemical formulas 1-1 to 1-12, chemical formulas 1-11a to 1-11c and chemical formulas 1-12a to 1-12c, specifically, ar 1 And Ar is a group 2 One of them is represented by the above chemical formula 2, ar 1 And Ar is a group 2 The remainder of (a) may be substituted or unsubstitutedC of (2) 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-12 Aryl groups.
In the chemical formula 2, R is d Each may be hydrogen; deuterium; substituted or unsubstituted C 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-12 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 5-30 Heteroaryl, or C 8-20 Heteroaryl, or C 12-18 Heteroaryl groups.
Preferably, in the above chemical formula 2, R d Each may be hydrogen or deuterium.
Specifically, n4 may be an integer of 0 to 7, or an integer of 0 to 4, an integer of 0 to 2, or 0 or 1.
More specifically, ar 1 And Ar is a group 2 One of them is dibenzofuranyl, dibenzothienyl, dibenzofuranyl substituted with deuterium, or dibenzothienyl substituted with deuterium represented by the above chemical formula 2, ar 1 And Ar is a group 2 The remainder of (2) may be substituted or unsubstituted C 6-30 Aryl groups.
Preferably Ar 1 And Ar is a group 2 One of them is dibenzofuranyl, dibenzothienyl, dibenzofuranyl substituted with deuterium, or dibenzothienyl substituted with deuterium, and the others may be phenyl, phenyl substituted with naphthyl, biphenyl, naphthyl substituted with phenyl, phenyl substituted with deuterium.
On the other hand, in the above chemical formulas 1-11a to 1-11c and chemical formulas 1-12a to 1-12c, R e Each hydrogen or deuterium.
In addition, in the above chemical formulas 1-11a to 1-11c and chemical formulas 1-12a to 1-12c, specifically, R f Each may be hydrogen; deuterium; substituted or unsubstituted C 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-12 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 5-30 Heteroaryl, or C 8-20 Heteroaryl, or C 12-18 Heteroaryl groups.
Preferably, R f Each may be hydrogen, deuterium, phenyl, or phenyl substituted with deuterium.
On the other hand, the compound represented by the above chemical formula 1 may be a compound substituted with no deuterium or 1 to 44 deuterium. As an example, the compound represented by the above chemical formula 1 may be unsubstituted or substituted with 2 to 42, or 2 to 40, or 2 to 36, or 3 to 32, or 3 to 25, or 3 to 20, or 3 to 10 deuterium.
As an example, in the compound represented by the above chemical formula 1, each of the dibenzofuranyl group substituted with deuterium or the dibenzothienyl group substituted with deuterium may be substituted with 3 to 7 pieces of deuterium, and the phenyl group substituted with deuterium may be substituted with 5 pieces of deuterium.
Representative examples of the compound represented by the above chemical formula 1 are shown below.
On the other hand, when the compound represented by the above chemical formula 1 is used in an organic light emitting device, it may be used together with the compound represented by the following chemical formula 3.
[ chemical formula 3]
In the above-mentioned chemical formula 3, a compound represented by formula 1,
R 3 and R is 4 Each independently is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
p is an integer of 0 to 10,
q is an integer of 0 to 7,
L 1 and L 2 Each independently is a single bond, or a substituted or unsubstituted C 6-60 An arylene group,
Ar 1 and Ar is a group 2 One of them is represented by the following chemical formula 4 or 5, and the remainder are substituted or unsubstituted C 6-60 An aryl group,
[ chemical formula 4]
[ chemical formula 5]
In the above-mentioned chemical formulas 4 and 5,
R 5 and R is 6 Each independently is a substituted or unsubstituted C 6-60 Aryl groups.
In particular, when the compound represented by the above chemical formula 3 is used in an organic light-emitting device together with the compound represented by the above chemical formula 1, an exciplex (exciplex) is advantageously formed, and the effect of low voltage, high efficiency, and long life characteristics can be more greatly exhibited.
Specifically, in the above chemical formula 3, R 3 And R is 4 Each independently may be hydrogen; deuterium; substituted or unsubstituted C 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-12 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 5-30 Heteroaryl, or C 8-20 Heteroaryl, or C 12-18 Heteroaryl groups.
Preferably, in the above chemical formula 1, R 3 And R is 4 Each may be hydrogen, deuterium, phenyl, or phenyl substituted with deuterium.
In addition, p may be an integer of 0 to 8, or an integer of 0 to 5, or an integer of 0 to 4, or an integer of 0 to 3, or an integer of 0 to 2, or 0 or 1.
In addition, q may be an integer of 0 to 6, or an integer of 0 to 5, or an integer of 0 to 4, or an integer of 0 to 3, or an integer of 0 to 2, or 0 or 1.
Specifically, in chemical formula 3, ar 3 And Ar is a group 4 One of them is represented by the above chemical formula 4 or 5, ar 3 And Ar is a group 4 The remainder of (2) may be substituted or unsubstituted C 6-30 Aryl, or C 6-28 Aryl or C 6-25 Aryl, or C 6-12 Aryl groups.
More specifically, ar 3 And Ar is a group 4 One of them is quinazoline or quinazoline substituted with deuterium, ar 3 And Ar is a group 4 The remainder of (2) may be substituted or unsubstituted C 6-30 Aryl groups.
Preferably Ar 3 And Ar is a group 4 One of them is quinazoline or quinazoline substituted with deuterium, and the others may be phenyl, phenyl substituted with naphthyl, biphenyl, naphthyl substituted with phenyl, naphthyl substituted with deuterium.
Representative examples of the compound represented by the above chemical formula 3 are shown below.
In addition, when the compound represented by the above chemical formula 1 is used in an organic layer of 1 or more layers of an organic light emitting device together with the compound represented by the above chemical formula 3, the weight ratio of the compound represented by the above chemical formula 1 to the compound represented by the above chemical formula 3 may be 20:80 to 80:20, or 30:70 to 70:30, or 35:65 to 65:35, or 40:60 to 60:40, preferably 45:55 to 55:45, or 50:50.
On the other hand, the compound represented by the above chemical formula 1 can be produced by a method shown in the following reaction formula 1 or reaction formula 2. The above-described production method may be more specifically described in the synthesis examples described below.
[ reaction type 1]
[ reaction type 2]
In the above equations 1 and 2, R 1 、R 2 、R a 、R b 、R c 、L 1 、L 2 、Ar 1 、Ar 2 N1, n2 and n3 are as defined in formula 1 above, Q 1 And Q 2 Each is a halogen group, preferably Cl, br or I, more preferably Cl or Br.
Specifically, the reactions of equations 1 and 2 above utilize a Buchwald-Hartwig reaction, which can be performed in, for example, bis (tri- (tert-butyl) phosphine) palladium (0) (bis (tri- (tert-butyl) phosphine) palladium (0), pd (P-tBu) 3 ) 2 ) Or tetrakis (triphenylphosphine) palladium (0) (tetrakis (triphenylphosphine) paladium (0), pd (PPh) 3 ) 4 ) The palladium catalyst (Pd catalyst) is carried out in the presence of a Pd catalyst compound.
The reaction may be carried out with sodium tert-butoxide (NaOtBu) and potassium carbonate (potassium carbonate, K) in the presence of 1 or more organic solvents (organic solvents) such as dichloromethane, ethyl acetate, diethyl ether, acetonitrile, isopropanol, propanol, tetrahydrofuran (THF), N-Dimethylformamide (DMF), dimethyl sulfoxide (DMSO), toluene or xylene 2 CO 3 ) Cesium carbonate (Cs) 2 CO 3 ) And 1 or more basic catalysts (base activators) are carried out together.
In another aspect, the present invention provides an organic light emitting device including the compound represented by the above chemical formula 1. As one example, the present invention provides an organic light emitting device, including: a first electrode, a second electrode provided opposite to the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains a compound represented by the chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure or a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.
On the other hand, the organic light emitting device according to the present invention may further include the compound represented by the above chemical formula 3 together with the compound represented by the above chemical formula 1. As one example, an organic light emitting device according to the present invention includes: the organic light-emitting device may further include a first electrode, a second electrode disposed opposite to the first electrode, and 1 or more organic layers disposed between the first electrode and the second electrode, wherein the 1 or more organic layers may include a compound represented by the chemical formula 3 together with the compound represented by the chemical formula 1.
The organic layer may include a hole injection layer, a hole transport layer, or a layer that performs hole injection and transport simultaneously, and the hole injection layer, the hole transport layer, or the layer that performs hole injection and transport simultaneously may include a compound represented by chemical formula 1.
The organic layer may include an electron blocking layer including a compound represented by chemical formula 1.
The organic layer may include a light-emitting layer including the compound represented by chemical formula 1. For example, the compound represented by the above chemical formula 1 may be contained as a host material of the light-emitting layer.
On the other hand, the light-emitting layer may further include a compound represented by chemical formula 3 together with the compound represented by chemical formula 1. At this time, the weight ratio of the compound represented by the above chemical formula 1 to the compound represented by the above chemical formula 3 is as described above.
In addition, the light-emitting layer further includes a dopant compound.
In addition, the light emitting layer includes a compound of chemical formula 1 and a dopant.
The light-emitting layer contains a compound of chemical formula 1, a compound of chemical formula 3, and a dopant.
As one example, the light emitting layer includes the compound of chemical formula 1 and the dopant at a weight ratio of 100:1 to 1:1.
In addition, the light emitting layer includes the compound of chemical formula 1 and the compound of chemical formula 3, and the dopant, and includes the weight of the compound of chemical formula 1 and the compound of chemical formula 3 added to the weight of the dopant in a weight ratio of 100:1 to 1:1.
In addition, the light emitting layer includes the compound of chemical formula 1 and the dopant in a weight ratio of 100:1 to 2:1.
In addition, the light emitting layer includes the compound of chemical formula 1 and the compound of chemical formula 3, and the dopant, and includes the weight of the compound of chemical formula 1 and the compound of chemical formula 3 added together and the weight of the dopant in a weight ratio of 100:1 to 2:1.
In addition, the light emitting layer includes the compound of chemical formula 1 and the dopant in a weight ratio of 100:1 to 5:1.
In addition, the light emitting layer includes the compound of chemical formula 1 and the compound of chemical formula 3, and the dopant in a weight ratio of 100:1 to 5:1, including the weight of the compound of chemical formula 1 added to the weight of the compound of chemical formula 3 and the weight of the dopant.
In addition, the light emitting layer includes the compound of chemical formula 1 and the dopant in a weight ratio of 100:1 to 95:5.
In addition, the light emitting layer includes the compound of chemical formula 1 and the compound of chemical formula 3, and the dopant in a weight ratio of 100:1 to 95:5, including the weight of the compound of chemical formula 1 added to the compound of chemical formula 3 and the weight of the dopant.
As an example, the dopant is a metal complex.
Specifically, the dopant is an iridium complex.
The organic layer includes a light-emitting layer, the light-emitting layer includes a dopant, and the dopant is selected from the following structural formulas.
The above-described explicit structure is a dopant compound, and is not limited thereto.
The organic layer may include a hole blocking layer including a compound represented by chemical formula 1.
The organic layer may include an electron transport layer, an electron injection layer, or a layer that performs electron injection and transport at the same time, and the electron transport layer, the electron injection layer, or the layer that performs electron injection and transport at the same time may include the compound represented by chemical formula 1.
In addition, the organic layer includes a light emitting layer and an electron blocking layer, and the light emitting layer or the electron blocking layer may include a compound represented by the chemical formula 1.
In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure of an organic light emitting device according to an embodiment of the present invention is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above light emitting layer.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, an electron injection and transport layer 8, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in 1 or more of the above hole injection layer, hole transport layer, electron blocking layer, light emitting layer, and electron injection and transport layer. Specifically, the compound represented by the above chemical formula 1 may be contained in the above light-emitting layer or the electron blocking layer, and for example, may be contained as a host material of the light-emitting layer or a material of the electron blocking layer.
The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that 1 or more of the above organic layers include the compound represented by chemical formula 1. In addition, when the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be manufactured as follows: an anode is formed by vapor deposition of a metal or a metal oxide having conductivity or an alloy thereof on a substrate by PVD (physical Vapor Deposition) method such as sputtering (sputtering) or electron beam evaporation (e-beam evaporation), then an organic layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like is formed on the anode, and then a substance that can function as a cathode is vapor deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
In addition, the compound represented by the above chemical formula 1 may be used not only in a vacuum deposition method but also in a solution coating method to form an organic layer in the production of an organic light-emitting device. In particular, the compound represented by the above chemical formula 1 has excellent solubility to a solvent used for the solution coating method, so that the solution coating method is easily applicable. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
The present invention provides a compound represented by the above chemical formula 1 and a coating composition containing a solvent.
The solvent is not particularly limited as long as it can dissolve or disperse the compound according to the present invention, and examples thereof include chlorine-based solvents such as chloroform, methylene chloride, 1, 2-dichloroethane, 1, 2-trichloroethane, chlorobenzene, and o-dichlorobenzene; tetrahydrofuran, twoEther solvents such as alkanes; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; ketone solvents such as acetone, methyl ethyl ketone, and cyclohexanone; ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; polyhydric alcohols such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, and 1, 2-hexanediol, and derivatives thereof; alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide; benzoate solvents such as butyl benzoate and methyl 2-methoxybenzoate; tetrahydronaphthalene, 3-phenoxy-toluene (3-phenoxy-toluene), and the like. In addition, in the case of the optical fiber, The above solvents may be used singly or in combination of two or more.
The viscosity of the coating composition is preferably 1cP to 10cP, and the coating composition is easily applied in the above range. Furthermore, the concentration of the compound according to the invention in the above-mentioned coating composition is preferably 0.1 to 20wt/v%.
The present invention also provides a method for forming a functional layer using the above-described coating composition. Specifically, the method comprises the following steps: a step of applying the above-described coating composition according to the present invention through a solution process; and a step of heat-treating the above-mentioned coated coating composition.
In the above heat treatment step, the heat treatment temperature is preferably 150 ℃ to 230 ℃. Further, the heat treatment time is 1 minute to 3 hours, more preferably 10 minutes to 1 hour. The heat treatment is preferably performed under an inert gas atmosphere such as argon or nitrogen.
As an example, the first electrode may be an anode, the second electrode may be a cathode, or the first electrode may be a cathode, and the second electrode may be an anode.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); znO of Al or SnO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole and polyaniline, but not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; liF/Al or LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that injects holes from an electrode, and the following compounds are preferable as the hole injection substance: a compound which has a hole transporting ability, has an effect of injecting holes from the anode, has an excellent hole injecting effect for the light emitting layer or the light emitting material, prevents excitons generated in the light emitting layer from migrating to the electron injecting layer or the electron injecting material, and has an excellent thin film forming ability. The HOMO (highest occupied molecular orbital ) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and a hole-transporting substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer is preferable, and a substance having a large mobility to the holes is preferable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. Specifically, there are 8-hydroxyquinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (EAzole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
The light-emitting layer may comprise a host materialA material and a dopant material. The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds Pyrimidine derivatives, etc., but are not limited thereto. Preferably, as the above-mentioned host material, the compound according to the present invention is used. Further, as the above-mentioned host material, the compound represented by the above-mentioned chemical formula 3 may be contained together with the compound represented by the above-mentioned chemical formula 1 according to the present invention.
Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene having an arylamino group,Bisindenopyrene, and the like, and a styrylamine compound is a compound in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like. Preferably, an iridium-based metal complex is used as the dopant material.
The light-emitting layer may be a red light-emitting layer, and when the compound according to the present invention is used as a host material, stability against electrons and holes increases, energy transfer from the host to the red dopant is well formed, and characteristics related to a driving voltage, light-emitting efficiency, and lifetime of the organic light-emitting device can be improved.
The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can well receive electrons from the cathode and transfer the electrons to the light emitting layer, and is preferably a substance having high mobility for electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The electron transport layer may be used with any desired cathode (cathode) material as used in the art. In particular, examples of suitable cathode materials are the usual materials having a low work function accompanied by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a silver layer.
The electron injection layer is a layer that injects electrons from an electrode, and preferably the following compound is used: a compound which has an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole injection layer, and has excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like, Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The organic light emitting device according to the present invention may be a bottom emission (bottom emission) device, a top emission (top emission) device, or a bi-directional light emitting device, and in particular, may be a bottom emission device requiring relatively high light emitting efficiency.
In addition, the compound according to the present invention may be contained in an organic solar cell or an organic transistor in addition to the organic light emitting device.
The production of the compound represented by the above chemical formula 1 and the organic light emitting device including the same is specifically illustrated in the following examples. However, the following examples are given by way of illustration of the present invention, and the scope of the present invention is not limited thereto.
Synthesis example
Synthesis example 1 Synthesis of Compound 1
Step 1) Synthesis of Compound 1-1
Under nitrogen atmosphere, (11-phenyl-11H-benzo [ a ]]Carbazol-8-yl) boronic acid ((11-phenyl-11H-benzol [ a)]carbazol-8-yl) carboxylic acid (15.0 g,44.5 mmol) and 3-bromo-9H-carbazole (3-bromoo-9H-carbazol) (12.0 g,48.9 mmol) were added to 300mL of Tetrahydrofuran (THF), stirred and refluxed. Then, potassium carbonate (K) 2 CO 3 24.6g,177.9mm ol) was dissolved in 74mL of water and the mixture was stirred sufficiently, and tetrakis (triphenylphosphine) palladium (0) (Pd (PPh) 3 ) 4 1.5g,1.3 mmol). After reacting for 8 hours, cooling to normal temperature, separating the organic layer from the water layer, and distilling the organic layer. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, whereby 14.9g of compound 1-1 was produced. (yield 73%, MS: [ M+H)] + ＝460)
Step 2) Synthesis of Compound 1
Compounds 1-1 (15.0 g,31.0 mmol) and 2-bromodibenzo [ b, d ] were reacted under nitrogen]Furan (2-bromoibendzo [ b, d ]]Furan) (8.4 g,34.1 mmol) was added to 300mL of toluene (tolene), stirred and refluxed. Then, sodium t-butoxide (NaOBu, 4.5g,46.5 mmol) and bis (tri-t-butylphosphine) palladium (0) (bis (tris-tert-butylphosphine) palladium (0)) (0.5 g,0.9 mmol) were charged. After the reaction for 6 hours, the mixture was cooled to room temperature, and the organic layer was separated from the water by chloroform and distilled. It was dissolved in chloroform again, washed with water for 2 times, and then the organic layer was separated, anhydrous magnesium sulfate was added, followed by filtration under stirring, and the filtrate was distilled under reduced pressure. After purifying the concentrated compound by silica gel column chromatography, 7.6g of compound 1 was produced by sublimation purification. (yield 39%, MS: [ M+H) ] + ＝626)
Synthesis example 2 Synthesis of Compound 2
In Synthesis example 1, (11-phenyl-11H-benzo [ a ]]Modification of carbazol-8-yl) boronic acid to (11- ([ 1,1' -biphenyl)]-4-yl) -11H-benzo [ a ]]Carbazol-8-yl) boronic acid ((11- ([ 1,1' -biphenyl) acid]-4-yl)-11H-benzo[a]carbazol-8-yl) carbonic acid), 2-bromodibenzo [ b, d]Modification of furan to 1-chlorodibenzo [ b, d]Furan (1-chlorodibenzzo [ b, d ]]Furan) was used, and compound 2 was produced in the same manner as in Synthesis example 1. (MS: [ M+H ]] + ＝702)
Synthesis example 3 Synthesis of Compound 3
In synthetic example 1, (11-phenyl-11H-benzo [ a ] carbazol-8-yl) boric acid was changed to (5- (naphthalen-2-yl) -5H-benzo [ b ] carbazol-2-yl) boric acid ((5- (naphthalen-2-yl) -5H-benzol [ b ] carbazol-2-yl) benzoic acid), and 2-bromodibenzo [ b, d ] furan was changed to 3-bromodibenzo [ b, d ] furan (3)
-bromodibenzo[b,d]Furan) was used, and compound 3 was produced in the same manner as in Synthesis example 1. (MS: [ M+H ]] + ＝676)
Synthesis example 4 Synthesis of Compound 4
In Synthesis example 1, (11-phenyl-11H-benzo [ a ]]Modification of carbazol-8-yl) boronic acid to (5- ([ 1,1' -biphenyl)]-3-yl) -5H-benzo [ b]Carbazol-2-yl) boronic acid ((5- ([ 1,1' -biphenyl) acid]-3-yl)-5H-benzo[b]carbazol-2-yl) benzoic acid), and 2-bromodibenzo [ b, d]Modification of furan to 4-chlorodibenzo [ b, d ]Thiophene (4-chlorodibenzzo [ b, d ]]thiophene) was used, and compound 4 was produced in the same manner as in synthesis example 1. (MS: [ M+H ]] + ＝718)
Synthesis example 5 Synthesis of Compound 5
In Synthesis example 1, (11-phenyl-11H-benzo [ a ]]Modification of carbazol-8-yl) boronic acid to (6-phenyl-11- (phenyl-d 5) -11H-benzo [ a ]]Carbazole-8-yl) boronic acid ((6-phenyl-11- (phenyl-d 5) -11H-benzol [ a)]carbazol-8-yl) carboxylic acid) was used, and compound 5 was produced in the same manner as in synthesis example 1. (MS: [ M+H ]] + ＝707)
Synthesis example 6 Synthesis of Compound 6
In Synthesis example 1, 3-bromo-9H-carbazole was changed to 3-bromo-5-phenyl-9H-carbazole (3-bromo-5-phenyl-9H-carbazole), and 2-bromodibenzo [ b ],d]Modification of furan to 3-bromodibenzo [ b, d ]]Thiophene (3-bromoibizo [ b, d ]]thiophene) was used, and compound 6 was produced in the same manner as in synthesis example 1. (MS: [ M+H ]] + ＝718)
Synthesis example 7 Synthesis of Compound 7
In Synthesis example 1, (11-phenyl-11H-benzo [ a ]]Carbazole-8-yl) boric acid is changed to (9-phenyl-9H-carbazol-3-yl) boric acid ((9-phenyl-9H-carbazol-3-yl) boric acid), and 3-bromo-9H-carbazole is changed to 8-bromo-11H-benzo [ a ]]Carbazole (8-bromoo-11H-benzol [ a ] ]carbazole), 2-bromodibenzo [ b, d]Modification of furan to 4-chlorodibenzo [ b, d]Furan (4-chlorodibenzzo [ b, d ]]Furan) was used, and compound 7 was produced in the same manner as in Synthesis example 1. (MS: [ M+H ]] + ＝626)
Synthesis example 8 Synthesis of Compound 8
In Synthesis example 1, (11-phenyl-11H-benzo [ a ]]Carbazole-8-yl) boric acid was changed to (9- (naphthalen-1-yl) -9H-carbazol-3-yl) boric acid ((9- (naphthalen-1-yl) -9H-carbazol-3-yl) boronic ac id), and 3-bromo-9H-carbazole was changed to 2-bromo-5H-benzo [ b ]]Carbazole (2-bromoo-5H-benzol [ b ]]carbazole), 2-bromodibenzo [ b, d]Modification of furan to 2-bromodibenzo [ b, d ]]Thiophene (2-bromod ibenzo [ b, d ]]thiophene) was used, and compound 8 was produced in the same manner as in synthesis example 1. (MS: [ M+H ]] + ＝692)
Synthesis example 9 Synthesis of Compound 9
In Synthesis example 1, (11-phenyl-11H-benzo [ a ]]Modification of carbazol-8-yl) boronic acid to (79-diphenyl-9H-carbazol-3-yl) boronic acid ((7, 9-diphenyl-9H-carbazol-3-yl) boronic), modification of 3-bromo-9H-carbazole to 2-bromo-5H-benzo [ b ]]Carbazole, 2-bromodibenzo [ b, d ]]Modification of furan to 1-chlorodibenzo [ b, d]Thiophene (1-chlorodibenzzo [ b, d ]]thiophene) was used, and compound 9 was produced in the same manner as in synthesis example 1. (MS: [ M+H ] ] + ＝718)
Synthesis example 10 Synthesis of Compound 10
In Synthesis example 1, (11-phenyl-11H-benzo [ a ]]Carbazole-8-yl) boric acid is changed to (9-phenyl-9H-carbazol-3-yl) boric acid ((9-phenyl-9H-carbazol-3-yl) boric acid), and 3-bromo-9H-carbazole is changed to 2-bromo-5H-benzo [ b ]]Carbazole, 2-bromodibenzo [ b, d ]]Modification of furan to 1- (3-chlorophenyl) dibenzo [ b, d]Furan (1- (3-chlorophenyl) dibenzo [ b, d)]Furan) was used, and compound 10 was produced in the same manner as in Synthesis example 1. (MS: [ M+H ]] + ＝702)
Examples (example)
Example 1-1
ITO (Indium Tin Oxide) is added to 1400 angstromangstrom), and the glass substrate coated with the film in thickness was put into distilled water in which a detergent was dissolved, and washed with ultrasonic waves. In this case, decon (Fisher Co.) from Fei Hill was used as the detergent TM The product of CON705, distilled water was filtered twice using a 0.22 μm sterile filter (sterilizing filter) manufactured by Millipore Co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing was completed, ultrasonic washing was performed for 10 minutes with solvents of isopropyl alcohol, acetone and methanol, respectively, and dried, and then, the resultant was transferred to a plasma cleaning machine. In addition, after the substrate was cleaned for 5 minutes by oxygen plasma, the substrate was transferred to true An air evaporation machine.
On the ITO transparent electrode thus prepared, the following compounds HI-A and LG-101 were sequentially and respectively usedAnd performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, as a hole transport layer, the following compound HT-A was used as +.>After vacuum evaporation, the following compound EB-A was used as an electron blocking layer>Is subjected to thermal vacuum evaporation. Next, on the EB-ase:Sub>A vapor deposited film, ase:Sub>A mixture of the following compound RH-ase:Sub>A and compound 1 in ase:Sub>A weight ratio of 1:1 was used as ase:Sub>A light emitting layer host, the following compound RD-ase:Sub>A was used as ase:Sub>A dopant, and the host and dopant were mixed in ase:Sub>A weight ratio of 98:2 and +.>Vacuum vapor deposition is performed to the thickness of (2) to form a red light-emitting layer. Next, as an electron injection and transport layer, the following compound ET-A and compound Liq were added in a ratio of 1:1 +.>Is subjected to thermal vacuum evaporation, and then the following compound Liq is added +.>Vacuum evaporation was performed on the thickness of (c). Magnesium and silver are sequentially added in a ratio of 10:1 and +.>Is vapor deposited with the thickness of aluminum +.>And vapor deposition is performed to form a cathode.
In the above process, the vapor deposition rate of the organic matter is maintained Second to->Lithium fluoride maintenance of cathode/sec->Vapor deposition rate per second, aluminum maintenance->Vapor deposition rate per second, vacuum degree was maintained at 2×10 during vapor deposition -7 To 5x10 -6 The support is thus fabricated into an organic light emitting device. />
Examples 1-2 to 1-10
Organic light-emitting devices of examples 1-2 to 1-10 were fabricated in the same manner as in example 1-1 above, except that compounds 2 to 10 described in table 1 below were used in place of compound 1 in the organic light-emitting device of example 1-1 above, respectively. At this time, a mixture of any one of the above compounds 2 to 10 and the above compound RH-a at a weight ratio of 1:1 is used as a host of the light-emitting layer, and the parenthesis in table 1 below refers to the weight ratio between the host compounds.
Comparative examples 1-1 to 1-5
Organic light-emitting devices of comparative examples 1-1 to 1-5 were manufactured in the same manner as in example 1-1 described above, except that compounds a to E described in table 1 below were used in place of compound 1 in the organic light-emitting devices of example 1-1, respectively. At this time, a mixture of any one of the above compounds a to E and the above compound RH-a at a weight ratio of 1:1 is used as a host of the light-emitting layer, and the parenthesis in table 1 below refers to the weight ratio between the host compounds. Further, compound A, B, C, D, E used in table 1 below is shown below.
Examples 2-1 to 2-10
In the organic light-emitting devices of example 1-1, the organic light-emitting devices of examples 2-1 to 2-10 were manufactured by the same method as in example 1-1 except that the compounds 1 to 10 described in the following table 2 were used as electron blocking layers instead of the above-described compound EB-ase:Sub>A, and only the above-described compound RH-ase:Sub>A which was not mixed with the compound 1 was used as ase:Sub>A main body of the light-emitting layer.
Comparative examples 2-1 to 2-5
In the organic light-emitting devices of example 1-1, organic light-emitting devices of comparative examples 2-1 to 2-5 were produced in the same manner as in example 1-1 except that the compounds ase:Sub>A to E described in table 2 below were used as electron blocking layers instead of the compound EB-ase:Sub>A described above, and only the compound RH-ase:Sub>A described above, which was not mixed with the compound 1, was used as ase:Sub>A main body of the light-emitting layer.
Experimental example
Experimental example 1
The organic light emitting devices fabricated in examples 1-1 to 1-10 and comparative examples 1-1 to 1-5 were subjected to current application, and voltage, efficiency and lifetime were measured, and the results are shown in table 1 below. At this time, the voltage and the efficiency were 10mA/cm applied 2 LT97 means a current density of 20mA/cm 2 The time (hr) required for the initial brightness (6000 nit) to decrease to 97% at the current density of (2).
TABLE 1
As shown in table 1 above, in the case of an organic light-emitting device manufactured using the compound of the present invention as a material of a light-emitting layer, excellent characteristics are exhibited in terms of efficiency, driving voltage, and/or stability (lifetime) of the organic light-emitting device.
An organic light emitting device according to an embodiment of the present invention is an organic light emitting device manufactured by bonding a heterocycle including O or S to a nitrogen atom of a parent nucleus structure formed by bonding a carbazole group at a specific position corresponding to a benzene ring in a benzocarbazole group, thereby reducing a driving voltage to a low voltage as compared with a material for a light emitting layer using a compound a having a carbazole group attached to a position corresponding to a naphthalene ring in a benzocarbazole group, a compound B not bonded to a heterocycle, or a compound C not bonded to a heterocycle including O or S but further bonded to an N-containing carbazole ring, or a compound D having a benzofuran ring included in a connecting group between a benzocarbazole group and a carbazole group, or a compound E having a different position of a naphthalene ring in a parent nucleus structure of a benzocarbazole group, while exhibiting characteristics of high efficiency and long lifetime.
Experimental example 2
The voltage, efficiency and lifetime of the organic light emitting devices fabricated in examples 2-1 to 2-10 and comparative examples 2-1 to 2-5 were measured by applying a current to the organic light emitting devices, and the results are shown in table 2 below. At this time, the voltage and the efficiency were 10mA/cm applied 2 LT97 is measured at 20mA/cm 2 The time (hr) required for the initial brightness (6000 nit) to decrease to 97%.
TABLE 2
As shown in table 2 above, in the case of an organic light-emitting device manufactured using the compound of the present invention as a material of an electron blocking layer, excellent characteristics are exhibited in terms of efficiency, driving voltage, and/or stability (lifetime) of the organic light-emitting device.
An organic light emitting device according to an embodiment of the present invention is an organic light emitting device manufactured by bonding a heterocycle including O or S to a nitrogen atom of a parent nucleus structure formed by bonding a carbazole group at a specific position corresponding to a benzene ring in a benzocarbazole group, thereby reducing a driving voltage to a low voltage as compared with a material in which a compound a having a carbazole group attached to a position corresponding to a naphthalene ring in a benzocarbazole group, a compound B not bonded to a heterocycle, or a compound C not bonded to a heterocycle including O or S but further bonded to an N-containing carbazole ring, or a compound D having a benzofuran ring included in a connecting group between a benzocarbazole group and a carbazole group, or a compound E having a different position of a naphthalene ring in a parent nucleus structure of a benzocarbazole group is used as an electron blocking layer, while exhibiting characteristics of high efficiency and long lifetime.
[ description of the symbols ]
1: substrate 2: anode
3: light emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: electron blocking layer 8: electron injection and transport layers.

Claims (12)

1. A compound represented by the following chemical formula 1:
[ chemical formula 1]
In the chemical formula 1 described above, a compound having the formula,
two adjacent R 1 Are combined with each other to form a benzene ring, which is hydrogen-bonded; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group is substituted and the substituted heteroaryl group is substituted,
the rest R 1 Is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstitutedComprising C selected from any one or more of N, O and S heteroatoms 2-60 A heteroaryl group, which is a group,
R 2 is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
R a 、R b and R is c Each independently is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
n1 and n2 are each an integer of 0 to 3,
n3 is an integer of 0 to 4,
L 1 and L 2 Each independently is a single bond, or a substituted or unsubstituted C 6-60 An arylene group,
Ar 1 and Ar is a group 2 One of them is represented by the following chemical formula 2, and the others are substituted or unsubstituted C 6-60 An aryl group,
chemical formula 2
In the chemical formula 2 described above, the chemical formula,
x is O or S, and the X is O or S,
R d each independently is hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
n4 is an integer from 0 to 7.
2. The compound according to claim 1, wherein the compound represented by 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 chemical formulas 1-1 and 1-2,
R a 、R b 、R c 、L 1 、L 2 、Ar 1 and Ar is a group 2 As defined in claim 1,
each R' is independently hydrogen; deuterium; substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C comprising one or more hetero atoms selected from N, O and S 2-60 A heteroaryl group, which is a group,
each n' is independently an integer from 0 to 6.
3. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is represented by any one of the following chemical formulas 1-3 to 1-10,
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
[ chemical formulas 1-7]
[ chemical formulas 1-8]
[ chemical formulas 1-9]
[ chemical formulas 1-10]
In the chemical formulas 1 to 3 of 1 to 10,
R a 、R b 、R c 、L 1 、L 2 、Ar 1 、Ar 2 r 'and n' are as defined in claim 2.
4. The compound of claim 1, wherein two adjacent R 1 Combine with each other to form a benzene ring substituted by hydrogen or deuterium, the remainder R 1 Hydrogen or deuterium.
5. The compound of claim 1, wherein R 2 Is hydrogen, deuterium, or substituted or unsubstituted C 6-30 Aryl groups.
6. The compound of claim 1, wherein R a 、R b And R is c Each hydrogen, deuterium, or substituted or unsubstitutedUnsubstituted C 6-30 Aryl groups.
7. The compound of claim 1, wherein L 1 And L 2 Each being a single bond, or a substituted or unsubstituted C 6-30 Arylene groups.
8. The compound of claim 1, wherein R d Each hydrogen or deuterium.
9. The compound of claim 1, wherein Ar 1 And Ar is a group 2 One of them is dibenzofuranyl, dibenzothienyl, dibenzofuran substituted with deuterium, or dibenzothienyl substituted with deuterium, ar 1 And Ar is a group 2 The remainder of (a) being substituted or unsubstituted C 6-30 Aryl groups.
10. The compound according to claim 1, wherein the compound represented by chemical formula 1 is any one selected from the group consisting of:
11. an organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 10.
12. The organic light-emitting device according to claim 11, wherein the organic layer containing the compound is a light-emitting layer or an electron blocking layer.
CN202280040511.9A 2021-06-10 2022-06-09 Novel compound and organic light emitting device comprising the same Pending CN117460728A (en)

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