CN116018338A - Novel compound and organic light emitting device comprising the same - Google Patents
Novel compound and organic light emitting device comprising the same Download PDFInfo
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- CN116018338A CN116018338A CN202180053914.2A CN202180053914A CN116018338A CN 116018338 A CN116018338 A CN 116018338A CN 202180053914 A CN202180053914 A CN 202180053914A CN 116018338 A CN116018338 A CN 116018338A
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- 125000004434 sulfur atom Chemical group 0.000 description 1
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- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
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- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
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- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
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- 229910052727 yttrium Inorganic materials 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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- 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
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
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Abstract
The present invention provides a novel compound and an organic light emitting device using the same.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2020-0150097, 11/2020, the entire contents of the publication 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 emitting devices 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,
r are each independentlyIs substituted or unsubstituted C 1-60 An alkyl group, a hydroxyl group,
R 1 to R 4 Each independently is hydrogen, deuterium, substituted or unsubstituted C 1-60 Alkyl, substituted or unsubstituted C 6-60 Aryl, or a substituent represented by the following chemical formula 2, but R 1 To R 4 At least one of which is a substituent represented by the following chemical formula 2,
[ chemical formula 2]
In the above-mentioned chemical formula 2,
X 1 to X 3 Each independently is N or CH, but X 1 To X 3 At least one of which is N,
L 1 to L 3 Each independently is a single bond, or a substituted or unsubstituted C 6-60 An arylene group,
n is 1,2 or 3,
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C containing more than 1 heteroatom in N, O and S 2-60 Heteroaryl groups.
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.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron suppression layer 8, a light-emitting layer 4, a hole blocking layer 9, an electron injection and transport layer 5, and a cathode 6.
Detailed Description
In the following, the invention will be described in more detail in order to aid understanding thereof.
(definition of terms)
In the present description of the invention,
and | represents a bond to the other substituent.
In the present specification, the term "substituted or unsubstituted" means that it is selected from deuterium; a halogen group; cyano 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 group
Arylthio->
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 1 or more heteroaryl groups in the S atom is substituted or unsubstituted, or a substituent bonded to 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 beTo be biphenyl. That is, biphenyl may be aryl or may be interpreted as a substituent in which 2 phenyl groups are linked. As an example, the term "substituted or unsubstituted" may be understood as "unsubstituted; or is selected from deuterium, halogen radicals, C 1-10 Alkyl, C 1-10 Alkoxy and C 6-20 More than 1 aryl group, for example, 1 to 5 substituents. In the present specification, the term "substituted with 1 or more substituents" is understood to mean, for example, "substituted with 1 to 5 substituents" or "substituted with 1 or 2 substituents".
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 substituent 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 substituent may be a substituent 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 substituent 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, specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2, 4-trimethyl-1-pentyl, 2, 4-trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl 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 having aromaticity (aromaticity). 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, triphenylene, pyrenyl, perylenyl,
A base, 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 fluorenyl group is substituted, it may be that
Etc. However, the present invention is not limited thereto.
In the present specification, the heteroaryl group is a heteroaryl 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 heteroaryl groupsExamples of the substituent include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl,
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, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), 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, the arylamine group, and the arylsilyl 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 heteroaryl 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 heteroaryl 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 heteroaryl groups can be applied thereto.
(Compound)
In another aspect, the present invention provides a compound represented by the above chemical formula 1.
Specifically, the compound represented by the above chemical formula 1 relates to a compound in which an N-containing six-membered heterocyclic substituent is bonded to a (1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene) core, and in this case, the N-containing six-membered heterocyclic substituent is substituted with at least one of carbon atoms of a benzene ring of the core.
The compound having such a structure has 1 or more N-containing six-membered heterocyclic substituents only in the benzene ring of the nucleus, thereby forming intramolecular polarization, and can have an improved dipole moment, maintain high thermal stability, and be very stable even at high vapor deposition temperatures. Thus, the organic light emitting device using the above compound can exhibit characteristics such as high efficiency, low driving voltage, and long lifetime, as compared with the conventional organic light emitting device.
In the above chemical formula 1, R may each independently be C 1-10 An alkyl group.
For example, each R independently can be methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, or tert-butyl.
At this time, R may be all the same.
In addition, R may be all methyl groups.
In the chemical formula 1, R is 1 To R 4 Each independently is hydrogen, deuterium, substituted or unsubstituted C 1-60 Alkyl, or substituted or unsubstituted C 6-60 Aryl, however, R 1 To R 4 At least one of them is a substituent represented by the above chemical formula 2. In this case, in the above chemical formula 1, when the number of substituents represented by the above chemical formula 2 is 2 or more, 2 or more substituents represented by the above chemical formula 2
The same as or different from each other.
Specifically, R 1 To R 4 One of them is a substituent represented by the above chemical formula 2, or R 1 To R 4 Two of them may be substituents represented by the above chemical formula 2.
At this time, the above compound may be represented by any one of the following chemical formulas 1A to 1F:
[ chemical formula 1A ]
[ chemical formula 1B ]
[ chemical formula 1C ]
[ chemical formula 1D ]
[ chemical formula 1E ]
[ chemical formula 1F ]
In the above chemical formulas 1A to 1F,
R、R 1 to R 4 、X 1 To X 3 、L 1 To L 3 、n、Ar 1 And Ar is a group 2 The same definition as in the above chemical formula 1.
At this time, the formula 2 is not shownR of the substituents shown 1 To R 4 Each independently may be hydrogen or deuterium.
In addition, in the above chemical formula 2, it may be:
X 1 is N, X 2 And X 3 CH; or alternatively
X 2 Is N, X 1 And X 3 CH; or alternatively
X 1 And X 2 Is N, X 3 CH; or alternatively
X 2 And X 3 Is N, X 1 CH; or alternatively
X 1 To X 3 All are N.
In the chemical formula 2, L 1 And L 2 Each independently may be a single bond, or unsubstituted, or may be deuterium substituted C 6-20 Arylene groups.
Specifically, L 1 And L 2 Each independently may be a single bond, phenylene, or naphthylene.
For example, L 1 And L 2 Each independently may be a single bond or any one selected from the following groups, but is not limited thereto.
In the chemical formula 2, L 3 Each independently may be a single bond, or unsubstituted, or may be deuterium substituted C 6-20 Arylene groups.
Specifically, L 3 May be a single bond, phenylene, naphthylene or biphenyldiyl.
At this time, n may be 1 or 2.
For example, (L) 3 ) n The compound may be a single bond or any one selected from the following groups, but is not limited thereto.
In addition, in the above chemical formula 2, ar 1 And Ar is a group 2 Each independently is C 6-20 Aryl, dibenzofuranyl or dibenzothiophenyl,
here, ar is 1 And Ar is a group 2 May be unsubstituted; or is selected from deuterium, C 1-10 Alkyl and C 6-20 More than 1 substituent in the aryl group is substituted.
Specifically, ar 1 And Ar is a group 2 Each independently is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, dibenzofuranyl, or dibenzothiophenyl,
here, ar is 1 And Ar is a group 2 May be unsubstituted; or is selected from deuterium, C 1-10 Alkyl and C 6-20 More than 1 substituent in the aryl group may be substituted, for example, with more than 1 substituent selected from deuterium, methyl, ethyl, propyl, isopropyl, butyl, t-butyl and phenyl.
More specifically, ar 1 And Ar is a group 2 Each independently may be phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, or dibenzofuranyl, dibenzothiophenyl.
For example, ar 1 And Ar is a group 2 Each independently may be any one selected from the following groups, but is not limited thereto:
at this time, ar 1 And Ar is a group 2 May be identical to each other. In addition, ar 1 And Ar is a group 2 May be different.
In addition, ar 1 And Ar is a group 2 At least one of which may be phenyl, naphthyl or phenanthryl.
In addition, the above compound may be represented by any one of the following chemical formulas 1-1 to 1-6:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1-4]
[ chemical formulas 1-5]
[ chemical formulas 1-6]
In the above chemical formulas 1-1 to 1-6,
X 1 to X 3 、L 1 To L 3 、n、Ar 1 And Ar is a group 2 The same definition as in the above chemical formula 1.
In addition, for example, in the above chemical formulas 1-3 to 1-6, 2 substituents
May be identical to each other. />
On the other hand, representative examples of the compounds represented by the above chemical formula 1 are shown below:
on the other hand, as an example, R of the compound represented by the above chemical formula 1 1 In the case of the substituent represented by the above chemical formula 2, the substituent can be produced by the following production method represented by the following reaction formula 1:
[ reaction type 1]
In the above reaction formula 1, X is halogen, preferably bromine or chlorine, and the definition of other substituents is the same as the above description.
Specifically, the compound represented by the above chemical formula 1 is produced by combining the starting materials SM1 and SM2 by a Suzuki-coupling reaction. Such a bell-wood coupling reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups used for the above reaction may be appropriately changed. The method for producing the compound represented by chemical formula 1 can be more specifically described in the production examples described below.
(organic light-emitting device)
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 suppression 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.
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 a light-emitting layer, and the light-emitting layer may include a compound represented by chemical formula 1.
The organic layer may include an electron injection layer, an electron transport layer, or a layer that performs electron injection and transport at the same time, and the electron injection layer, the electron transport 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 may include a hole blocking layer or an electron injection and transport layer, and the hole blocking layer or the electron injection and transport layer may include a compound represented by 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, as an organic layer, a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode, in addition to the light-emitting layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller or larger number of organic layers.
The organic light-emitting device according to the present invention may have a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate in which the first electrode is an anode and the second electrode is a cathode. Further, the organic light emitting device according to the present invention may be an organic light emitting device having a reverse structure (inverted type) in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate in which the first electrode is a cathode and the second electrode is an anode. 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 hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above electron injection and transport layer.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, an electron suppression layer 8, a light-emitting layer 4, a hole blocking layer 9, an electron injection and transport layer 5, and a cathode 6.
In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above electron injection and transport 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: PVD (physical Vapor Deposition) process such as sputtering (sputtering) or electron beam evaporation (physical vapor deposition) is used to vapor-deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is 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. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
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. As the hole transporting material, hexanitrile hexaazabenzophenanthrene-based organic material, arylamine-based organic material, conductive polymer, block copolymer having conjugated moiety and non-conjugated moiety at the same time, and the like can be used, but the present invention is not limited thereto. In addition, the hole transport layer may be formed of 2 or more layers in the organic light-emitting device using the hole transport substance, and in this case, the hole transport substances included in 2 or more hole transport layers may be the same or different from each other.
In addition, the above organic light emitting device may further be provided with an electron suppression layer. Specifically, the electron suppression layer refers to a layer as follows: the hole transport layer is preferably formed on the light emitting layer, and is preferably provided in contact with the light emitting layer, and serves to improve the efficiency of the organic light emitting device by adjusting the hole mobility, thereby preventing excessive migration of electrons and improving the probability of hole-electron bonding. The electron blocking layer contains an electron blocking material, and as an example of such an electron blocking material, an arylamine-based organic material or the like can be used, but the electron blocking material is not limited thereto.
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 preferably has high quantum efficiency for fluorescence or phosphorescence. Specifically, there are 8-hydroxyquinoline aluminum complex (Alq 3 ) A carbazole-based compound, a dimeric styryl (dimerized styryl) compound; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (E
Azole, 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 described above may include a host material and a dopant material as described above. The host material may also include aromatic fused ring derivatives or heterocyclic containing 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.
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,
Or bisindenopyrene, wherein the styrylamine compound is a compound having at least 1 aryl vinyl group substituted on a substituted or unsubstituted aryl amine, and is selected from aryl, silyl, and alkane1 or more substituents in the group consisting of a group, cycloalkyl group and arylamino group are substituted or unsubstituted. 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.
In addition, the organic light emitting device may further be provided with a hole blocking layer. Specifically, the hole blocking layer refers to the following layer: the layer formed on the light-emitting layer is preferably provided in contact with the light-emitting layer, and serves to improve the efficiency of the organic light-emitting device by adjusting the electron mobility and preventing excessive migration of holes to increase the probability of hole-electron bonding. The hole blocking layer contains a hole blocking substance, and as an example of such a hole blocking substance, the compound represented by the above chemical formula 1 may be used, or an azine derivative, a triazole derivative, a triazine-containing compound may be used,
The compound having an electron withdrawing group introduced therein, such as an diazole derivative, a phenanthroline derivative, and a phosphine oxide derivative, but is not limited thereto.
The electron injection and transport layer is a layer that injects electrons from an electrode and transports the received electrons to a light emitting layer and functions as an electron transport layer and an electron injection layer, and is formed on the light emitting layer or the hole blocking layer. Such an electron injection and transport substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having high electron mobility. As a specific example of the electron injecting and transporting substance, a compound represented by the above chemical formula 1 may be used, or an Al complex of 8-hydroxyquinoline containing Alq may be used 3 But not limited to, complexes of (c) with (c), organic radical compounds, hydroxyflavone-metal complexes, triazine derivatives, and the like. Or can be mixed with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,
Azole,/->
The compounds are used together with a derivative thereof, a metal complex, a nitrogen-containing five-membered ring derivative, or the like, but are not limited thereto.
The electron injection and transport layer may be formed as separate layers such as an electron injection layer and an electron transport layer. In this case, an electron transporting layer is formed over the light emitting layer or the hole blocking layer, and as an electron transporting substance contained in the electron transporting layer, the above-described electron injecting and transporting substance can be used. Further, an electron injection layer is formed on the electron transport layer, and LiF, naCl, csF, li, may be used as an electron injection substance contained in the electron injection layer 2 O, baO fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide,
Azole,/->
Diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, and the like, and their derivatives, metal complexes, and nitrogen-containing five-membered ring derivatives, and the like.
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 of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.
In addition, the compound represented by the above chemical formula 1 may be included 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.
Production example 1: production of Compound 1
After 6-bromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (5.55 g,20.79 mmol) and a-1 (13.42, 22.87 mmol) were completely dissolved in 240mL of tetrahydrofuran in a 500mL round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 mL) was added, tetrakis (triphenylphosphine) palladium (0.71 g,0.61 mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 250ml of tetrahydrofuran to give compound 1 (7.65 g, 57%).
MS[M+H] + ＝648
Production example 2: production of Compound 2
After 6, 7-dibromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (4.68 g,13.53 mmol) and a-2 (12.94 g,29.76 mmol) were completely dissolved in 240mL of tetrahydrofuran in a 500mL round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 mL) was added, tetrakis (triphenylphosphine) palladium (0.94 g,0.81 mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 250mL of ethyl acetate to give Compound 2 (8.11 g, 75%).
MS[M+H] + ＝804
Production example 3: production of Compound 3
After 6, 7-dibromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (4.89 g,14.13 mmol) and a-3 (13.46 g,31.09 mmol) were completely dissolved in 240mL of tetrahydrofuran in a 500mL round-bottomed flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 mL) was added, tetrakis (triphenylphosphine) palladium (0.98 g,0.85 mmol) was added, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 270mL of tetrahydrofuran to give Compound 3 (6.88 g, 61%).
MS[M+H] + ＝802
Production example 4: production of Compound 4
After the compound 5, 8-dibromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (5.14 g,14.86 mmol) and the compound a-2 (14.22 g,32.68 mmol) were completely dissolved in 240mL of tetrahydrofuran in a 500mL round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 mL) was added, tetrakis (triphenylphosphine) palladium (1.03 g,0.89 mmol) was added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 250mL of tetrahydrofuran to give Compound 4 (7.23 g, 61%).
MS[M+H] + ＝804
Production example 5: production of Compound 5
After 6, 7-dibromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (5.33 g,15.40 mmol) and a-4 (14.74 g,33.89 mmol) were completely dissolved in 240mL of tetrahydrofuran in a 500mL round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 mL) was added, tetrakis (triphenylphosphine) palladium (1.07 g,0.92 mmol) was added, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 250mL of tetrahydrofuran to give Compound 5 (8.22 g, 66%).
MS[M+H] + ＝804
Production example 6: production of Compound 6
After 6-bromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (6.77 g,25.36 mmol) and a-5 (16.37 g,27.89 mmol) were completely dissolved in 240mL of tetrahydrofuran in a 500mL round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 mL) was added, tetrakis (triphenylphosphine) palladium (0.88 g,0.76 mmol) was added, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 240mL of ethyl acetate to give Compound 6 (12.27 g, 75%).
MS[M+H] + ＝648
Production example 7: production of Compound 7
After the compound 5, 7-dibromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (5.77 g,16.68 mmol) and the compound a-6 (15.92 g,36.69 mmol) were completely dissolved in 240mL of tetrahydrofuran in a 500mL round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 mL) was added, tetrakis (triphenylphosphine) palladium (1.16 g,1.01 mmol) was added, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 250mL of tetrahydrofuran to give Compound 7 (8.88 g, 66%).
MS[M+H] + ＝802
Production example 8: production of Compound 8
After the compound 5, 6-dibromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (6.11 g,17.66 mmol) and the compound a-2 (16.90 g,38.85 mmol) were completely dissolved in 240mL of tetrahydrofuran in a 500mL round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (120 mL) was added, tetrakis (triphenylphosphine) palladium (1.22 g,1.02 mmol) was added, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 230mL of tetrahydrofuran to give Compound 8 (7.14 g, 50%).
MS[M+H] + ＝804
Production example 9: production of Compound 9
After 6-bromo-1, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (6.67 g,24.98 mmol) and a-7 (19.26 g,27.48 mmol) were completely dissolved in 240mL of tetrahydrofuran in a 500mL round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 mL) was added, tetrakis (triphenylphosphine) palladium (0.87 g,0.75 mmol) was added, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 240mL of tetrahydrofuran to give Compound 9 (10.17 g, 53%).
MS[M+H] + ＝763
Production example 10: production of Compound 10
After the compound 2,2' - (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalene-2, 3-diyl) bis (4, 5-tetramethyl-1, 3, 2-dioxaborolan) (3.83 g,8.69 mmol) and the compound a-8 (7.11 g,19.32 mmol) were completely dissolved in 240mL of tetrahydrofuran in a 500mL round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 mL) was added, and tetrakis (triphenylphosphine) palladium (0.67 g,0.58 mmol) was added and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 270mL of ethyl acetate to yield compound 10 (8.92 g, 54%).
MS[M+H] + ＝852
Production example 11: production of Compound 11
After 2,2' - (5, 8-tetramethyl-5, 6,7, 8-tetrahydronaphthalene-1, 4-diyl) bis (4, 5-tetramethyl-1, 3, 2-dioxaborolan) (3.84 g,8.74 mmol) and a-9 (6.95 g,19.41 mmol) were completely dissolved in 240mL of tetrahydrofuran in a 500mL round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 mL) was added, and tetrakis (triphenylphosphine) palladium (0.67 g,0.58 mmol) was added and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 250mL of tetrahydrofuran to give Compound 11 (10.11 g, 63%).
MS[M+H] + ＝831
Example 1-1
To ITO (indium tin oxide)
The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed with distilled water twice for 10 minutesAnd (5) washing. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.
On the ITO transparent electrode as an anode thus prepared, the following compound HI1 and the following compound HI2 were mixed in a ratio of 98:2 (molar ratio)
And performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, a compound represented by the following formula HT1 is added>
Vacuum evaporation is performed to form a hole transport layer. Next, on the hole transport layer, the film thickness is +.>
The EB1 compound was vacuum-evaporated to form an electron-inhibiting layer.
Then, on the electron suppression layer, the film thickness is set to be
A compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD were vacuum-evaporated at a weight ratio of 25:1 to form a light-emitting layer.
On the light-emitting layer, the film thickness is set to
The compound represented by compound 1 produced in production example 1 was subjected to vacuum evaporation to form a hole blocking layer. Next, on the hole blocking layer, a compound represented by the following chemical formula ET1 and a compound represented by the following chemical formula LiQ were vacuum-evaporated at a weight ratio of 1:1 to form ∈ ->
Form an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added +.>
Is made of aluminum +.>
And the thickness of the metal layer is evaporated to form a cathode.
In the above process, the vapor deposition rate of the organic matter is maintained
Lithium fluoride maintenance of cathode
Is kept at>
Is to maintain the vacuum degree during vapor deposition>
The support is thus fabricated into an organic light emitting device.
Examples 1-2 to 1-11
An organic light-emitting device was manufactured in the same manner as in example 1-1 above, except that the compound described in table 1 below was used instead of the compound of manufacturing example 1. At this time, the structures of the compounds used in the above examples were organized as follows.
Comparative examples 1-1 to 1-3
An organic light-emitting device was manufactured in the same manner as in example 1-1 above, except that the compound described in table 1 below was used instead of the compound of manufacturing example 1. The structures of HB1, HB2, and HB3 used in table 1 below are shown below.
Experimental example 1
When a current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in table 1 below. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.
TABLE 1
As shown in table 1 above, the organic light-emitting device using the compound of the present invention as a hole blocking layer exhibited excellent characteristics in driving voltage, light-emitting efficiency and lifetime as compared with the organic light-emitting device of the comparative example.
Specifically, the organic light emitting device of the above example can be confirmed to exhibit improved efficiency and significantly long lifetime while having a lower driving voltage, compared to the organic light emitting device of comparative example 1-1 using HB1 compound having 9, 10-tetramethyl-9, 10-dihydro-anthracene nucleus and the organic light emitting devices of comparative examples 1-2 and 1-3 using HB2 and HB3 compounds having 10, 10-dimethyl-10H-spiro [ anthracene-9, 9' -fluorene ] nucleus, respectively.
Symbol description
1: substrate 2: anode
3: hole transport layer 4: light-emitting layer
5: electron injection and transport layer 6: cathode electrode
7: hole injection layer 8: electron suppression layer
9: a hole blocking layer.
Claims (13)
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,
r are each independently substituted or unsubstituted C 1-60 An alkyl group, a hydroxyl group,
R 1 to R 4 Each independently is hydrogen, deuterium, substituted or unsubstituted C 1-60 Alkyl, substituted or unsubstituted C 6-60 Aryl, or a substituent represented by the following chemical formula 2, but R 1 To R 4 At least one of which is a substituent represented by the following chemical formula 2,
chemical formula 2
In the chemical formula 2 described above, the chemical formula,
X 1 to X 3 Each independently is N or CH, but X 1 To X 3 At least one of which is N,
L 1 to L 3 Each independently is a single bond, or a substituted or unsubstituted C 6-60 An arylene group,
n is 1,2 or 3,
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted C 6-60 An aryl group; or substituted or unsubstituted C containing more than 1 heteroatom in N, O and S 2-60 Heteroaryl groups.
2. The compound of claim 1, wherein R is all the same.
3. The compound of claim 2, wherein R is methyl.
4. The compound of claim 1, wherein R 1 To R 4 Is a substituent represented by the chemical formula 2; or alternatively
R 1 To R 4 Is a substituent represented by the chemical formula 2.
5. The compound of claim 1, wherein X 1 Is N, X 2 And X 3 CH; or alternatively
X 2 Is N, X 1 And X 3 CH; or alternatively
X 1 And X 2 Is N, X 3 CH; or alternatively
X 2 And X 3 Is N, X 1 CH; or alternatively
X 1 To X 3 Are all N.
6. The compound of claim 1, wherein L 1 And L 2 Each independently is a single bond, phenylene, or naphthylene.
7. The compound of claim 1, wherein L 3 Is a single bond, phenylene, naphthylene or biphenyldiyl,
n is 1 or 2.
8. The compound of claim 1, wherein Ar 1 And Ar is a group 2 Each independently is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, dibenzofuranyl, or dibenzothiophenyl.
9. The compound of claim 8, wherein Ar 1 And Ar is a group 2 Each independently is any one selected from the group consisting of:
10. the compound according to claim 1, wherein the compound is represented by any one of the following chemical formulas 1-1 to 1-6:
chemical formula 1-1
Chemical formula 1-2
Chemical formulas 1-3
Chemical formulas 1-4
Chemical formulas 1-5
Chemical formulas 1-6
In the chemical formulas 1-1 to 1-6,
X 1 to X 3 、L 1 To L 3 、n、Ar 1 And Ar is a group 2 As defined in claim 1.
11. The compound of claim 1, wherein the compound is any one selected from the group consisting of:
12. 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 11.
13. The organic light-emitting device according to claim 12, wherein the organic layer containing the compound is a hole blocking layer or an electron injection and transport layer.
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