CN113474330A - Novel compound and organic light emitting device using the same - Google Patents
Novel compound and organic light emitting device using the same Download PDFInfo
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- CN113474330A CN113474330A CN202080016382.0A CN202080016382A CN113474330A CN 113474330 A CN113474330 A CN 113474330A CN 202080016382 A CN202080016382 A CN 202080016382A CN 113474330 A CN113474330 A CN 113474330A
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- 125000004434 sulfur atom Chemical group 0.000 description 1
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- 239000010409 thin film Substances 0.000 description 1
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
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- 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
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- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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Abstract
The 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. 10-2019-0121791, year 10, month 1, 2019 and korean patent application No. 10-2020-0116329, month 10, 2020, the entire contents of which are incorporated herein by reference.
The present invention relates to a novel compound and an organic light emitting device 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, a fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
An 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 the 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, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, which emit light when they transition to the ground state again.
For organic materials used for the organic light emitting devices as described above, development of new materials is continuously demanded.
Documents of the prior art
Patent document 1: korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Technical subject
The present invention relates to a novel compound and an organic light emitting device comprising the same.
Means for solving the problems
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-described chemical formula 1,
R1to R4Are each hydrogen or deuterium, or R1To R4Two adjacent of them are combined to form a benzene ring, and the rest is hydrogen or deuterium,
L1to L3Each independently is a single bond; substituted or unsubstituted C6-60An arylene group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60A heteroarylene group, a heteroaryl group,
Ar1is substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S2-60A heteroaryl group.
In addition, the present invention provides an organic light emitting device, comprising: a first electrode; a second electrode provided to face the first electrode; and 1 or more organic layers between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound represented by 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, low driving voltage, and/or improvement of life span 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 suppression, light emission, electron transport, or electron injection.
Drawings
Fig. 1 illustrates an example of an organic light emitting device composed of a substrate 1, an anode 2, an organic layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 8, a hole suppression layer 9, an electron transport layer 10, an electron injection layer 11, and a cathode 4.
Detailed Description
Hereinafter, the present invention will be described in more detail to assist understanding thereof.
The present invention provides a compound represented by the above chemical formula 1.
In the context of the present specification,
and
represents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means substituted with a substituent 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 (Alkyl thio); arylthio (Aryl thio); alkylsulfonyl (Alkyl sulfonyl); arylsulfonyl (Aryl sulfonyl); a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; or 1 or more substituents of 1 or more heterocyclic groups containing N, O and S atoms, or substituted or unsubstituted by 2 or more substituents of the above-exemplified substituents being bonded. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the 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, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 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 in 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, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In the present specification, the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.
In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.
In the present specification, the alkyl group may be linear or branched, 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 alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a3, 3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, a n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propylpentyl group, a n-nonyl group, a2, 2-dimethylheptyl group, a 1-ethyl-propyl group, a1, 1-dimethyl-propyl group, a 1-propyl group, a tert-pentyl group, a 2-pentyl group, a hexyl, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.
In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there may be mentioned, but not limited to, 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.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,
And a fluorenyl group, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. When the fluorenyl group is substituted, the compound may be
And the like. But is not limited thereto.
In the present 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 the number of carbon atoms is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Azolyl group,
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolineA group selected from the group consisting of quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoyl
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the above-mentioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamino group is the same as the above-mentioned alkyl group. In the present specification, the heteroaryl group in the heteroarylamine can be applied to the above description about the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as exemplified above for the alkenyl group. In the present specification, the arylene group is a 2-valent group, and the above description of the aryl group can be applied thereto. In the present specification, a heteroarylene group is a 2-valent group, and in addition to this, the above description about a heterocyclic group can be applied. In the present specification, the hydrocarbon ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description about the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocyclic group is not a 1-valent group but a combination of 2 substituents, and the above description of the heterocyclic group can be applied.
The compound of chemical formula 1 of the present invention has a structure comprising adamantyl group
And a structure in which the amine substituent of (a) is bonded to a carbazole moiety (motif) through a biphenyl linking group. In this case, the compound of chemical formula 1 of the present invention has carbazole based on the phenyl group bonded to the carbazole moiety in the biphenyl linking groupAnd a form in which a part thereof is positioned in the meta (meta) direction of the phenyl group with respect to the amine substituent. Therefore, when the compound of the present invention is used as a material for an organic layer of an organic light emitting device, excellent efficiency and low voltage characteristics can be achieved.
The above chemical formula 1 may be specifically represented by any one of the following chemical formulas 1-1 to 1-4.
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1 to 4]
In the above chemical formulae 1-1 to 1-4, L1To L3And Ar1The same as defined in chemical formula 1.
Preferably, Ar1Is substituted or unsubstituted C6-30An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S2-30A heteroaryl group.
More preferably, Ar1Is any one selected from the following groups:
in the above-mentioned group, the group,
x is NR'4The oxygen, the oxygen or the sulfur is selected from the group consisting of O and S,
R'1to R'4Each independently hydrogen, substituted or unsubstituted C1-10Alkyl, or substituted or unsubstituted C6-12And (4) an aryl group.
Preferably, X is O or S, R'1To R'3Each independently hydrogen, methyl or phenyl.
Preferably, L1To L3Each independently a single bond, substituted or unsubstituted C6-30Arylene, or substituted or unsubstituted C containing O or S heteroatoms2-30A heteroarylene group.
More preferably, L1Is a single bond, phenylene, biphenylene or naphthylene.
More preferably, L2And L3Each independently a single bond or phenylene.
Representative examples of the compound represented by the above chemical formula 1 are as follows:
the present invention also provides a method for producing the compound represented by the above chemical formula 1, as shown in the following reaction formula 1.
[ reaction formula 1]
In the above reaction scheme 1, L1To L3And Ar1As defined above, X 'is halogen, preferably, X' is chlorine or bromine.
The above reaction formula 1 is an amine substitution reaction, and is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group for the amine substitution reaction may be modified according to a technique known in the art. The above-described manufacturing method can be further embodied in the manufacturing examples described later.
In addition, the present invention provides an organic light emitting device comprising the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light emitting device, comprising: a first electrode; a second electrode provided to face the first electrode; and 1 or more organic layers between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound represented by chemical formula 1.
The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting 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 a smaller number of organic layers may be included.
In addition, the organic layer may include a light emitting layer including the compound represented by the chemical formula 1. In particular, the compound according to the present invention can be used as a host of a light emitting layer.
In addition, the organic layer may include a hole injection layer, a hole transport layer, or an electron suppression layer, and the hole injection layer, the hole transport layer, or the electron suppression layer includes the 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 of 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 inverted (inverted type) organic light emitting device 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 composed of a substrate 1, an anode 2, an organic layer 3, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be included in the above organic layer.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 8, a hole suppression layer 9, an electron transport layer 10, an electron injection layer 11, 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 layers among the above hole injection layer, hole transport layer, electron suppression layer, light emitting layer, hole suppression layer, electron transport layer, and electron injection 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 the above chemical formula 1. In addition, in the case where the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.
For example, the organic light emitting device 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 produced as follows: the organic el display device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) method to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.
In addition, the compound represented by the above chemical formula 1 may be formed into an organic layer not only by a vacuum evaporation method but also by a solution coating method in the manufacture of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by depositing a cathode material, an organic layer, and an anode material on a substrate in this order (WO 2003/012890). However, the production method is not limited thereto.
In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
The anode material is preferably a material having a large work function in order to smoothly inject holes into the organic layer. Specific examples of the anode material 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-Al or SnO2A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include magnesiumMetals such as calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; LiF/Al or LiO2And a multilayer structure material such as Al, but not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: a compound having an ability to transport holes, having an effect of injecting holes from an anode, having an excellent hole injection effect for a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to an electron injection layer or an electron injection material, and having an excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport substance is a substance that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and is preferably a substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
The electron-inhibiting layer inhibits electrons injected from the cathode from being transferred to the anode side without being recombined in the light-emitting layer, thereby improving the efficiency of the organic light-emitting device. According to a specific example of the present invention, as a substance constituting the electron-inhibiting layer, a compound represented by the above chemical formula 1 can be used.
The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably fluorescent or phosphorescentA substance having high quantum efficiency. As an example, there is an 8-hydroxyquinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is
Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; a polyfluorene; rubrene, etc., but not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic compounds, and the like. Specifically, the aromatic fused ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a carbazole derivative, a dibenzofuran derivative, a ladder furan compound, a pyrimidine derivative, and the like, but is not limited thereto. In particular, in the present invention, the compound represented by the above chemical formula 1 may be used as a host material of the light emitting layer, in which case low voltage, high efficiency, and/or long life characteristics of the organic light emitting device may be obtained.
As the dopant material, there are an aromatic amine derivative, a styryl amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, or the like having an arylamino group,
Diindenopyrene, and the like, and styrylamine compounds are compounds in which at least 1 arylvinyl group is substituted on a substituted or unsubstituted arylamine, and are substituted or unsubstituted with 1 or 2 or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. Further, as the metal complex, there is an iridium complexAnd platinum complexes, but are not limited thereto.
The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can favorably receive electrons from the cathode and transfer the electrons to the light emitting layer, and is suitable for a substance having a high electron mobility. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq3The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode substances are, in particular, the customary substances having a low work function and accompanied by an aluminum or silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum or silver layer.
The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound of: a compound having an ability to transport electrons, having an effect of injecting electrons from a cathode, having an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and having an excellent thin-film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.
The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
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 manufacture 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 provided to illustrate the present invention, and the scope of the present invention is not limited thereto.
[ production example ]
Production example 1
After completely dissolving the compound 9- (4'-chloro- [1,1' -biphenyl ] -3-yl) -9H-carbazole (6.82g, 19.32mmol) and the compound a1(9.67g, 21.25mmol) in 270mL of xylene in a 500mL round-bottomed flask under a nitrogen atmosphere, NaOtBu (2.23g, 23.18mmol) was added, Bis (tri-tert-butylphosphine) palladium (0) (Bis (tri-tert-butylphosphine) palladium (0)) (0.20g, 0.39mmol) was added, and the mixture was stirred under heating for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 330mL of ethyl acetate, thereby producing production example 1(8.34g, yield: 56%).
MS[M+H]+＝774
Production example 2
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving compound 9- (4'-chloro- [1,1' -biphenyl ] -3-yl) -9H-carbazole (7.23g, 20.48mmol) and compound a2(10.25g, 22.53mmol) in 250mL of xylene, NaOtBu (2.36g, 24.58mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.21g, 0.41mmol) was added, and the mixture was stirred under heating for 6 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 320mL of ethyl acetate, thereby producing production example 2(7.96g, yield: 50%).
MS[M+H]+＝774
Production example 3
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving compound 9- (4'-chloro- [1,1' -biphenyl ] -3-yl) -9H-carbazole (7.55g, 21.39mmol) and compound a3(9.27g, 23.53mmol) in 220mL of xylene, NaOtBu (2.47g, 25.67mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.22g, 0.43mmol) was added, and the mixture was stirred under heating for 2 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 310mL of ethyl acetate, thereby producing production example 3(8.09g, yield: 53%).
MS[M+H]+＝738
Production example 4
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving compound 9- (4'-chloro- [1,1' -biphenyl ] -3-yl) -9H-carbazole (6.33g, 17.93mmol) and compound a4(8.26g, 19.73mmol) in 250mL of xylene, NaOtBu (2.07g, 21.52mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.18g, 0.36mmol) was added, and the mixture was stirred with heating for 3 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 300mL of ethyl acetate, thereby producing production example 4(7.22g, yield: 55%).
MS[M+H]+＝738
Production example 5
In a 500mL round-bottom flask under nitrogen, after completely dissolving compound 9- (4'-chloro- [1,1' -biphenyl ] -3-yl) -9H-carbazole (6.67g, 18.90mmol) and compound a5(8.19g, 20.78mmol) in 290mL of xylene, NaOtBu (2.18g, 22.67mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.19g, 0.38mmol) was added, and the mixture was stirred under heating for 5 hours. Production example 5(7.28g, yield: 54%) was produced by reducing the temperature to normal temperature, filtering to remove the base, concentrating xylene under reduced pressure, and recrystallizing from 220mL of ethyl acetate.
MS[M+H]+＝727
Production example 6
In a 500mL round-bottom flask under nitrogen, after completely dissolving compound 9- (4'-chloro- [1,1' -biphenyl ] -3-yl) -9H-carbazole (5.92g, 16.77mmol) and compound a6(10.02g, 18.45mmol) in 260mL of xylene, NaOtBu (1.93g, 20.12mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.17g, 0.34mmol) was added, and the mixture was stirred with heating for 7 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 340mL of ethyl acetate, thereby producing production example 6(9.11g, yield: 63%).
MS[M+H]+＝862
Production example 7
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving compound 9- (4'-chloro- [1,1' -biphenyl ] -3-yl) -9H-carbazole (6.37g, 18.05mmol) and compound a7(9.31g, 19.85mmol) in 280mL of xylene, NaOtBu (2.08g, 21.65mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.18g, 0.36mmol) was added, and the mixture was stirred with heating for 6 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 230mL of ethyl acetate, thereby producing production example 7(8.75g, yield: 60%).
MS[M+H]+＝788
Production example 8
In a 500mL round-bottomed flask under nitrogen, after completely dissolving compound 9- (4 "-chloro- [1,1':4', 1" -terphenyl ] -3-yl) -9H-carbazole (9- (4 "-chloro- [1,1':4', 1" -terphenyl ] -3-yl) -9H-carbazole) (5.55g, 12.91mmol) and compound a8(5.38g, 14.20mmol) in 250mL xylene, NaOtBu (1.49g, 15.49mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.13g, 0.26mmol) was added, and stirring was performed with heating for 4 hours. Production example 8(6.02g, yield: 60%) was produced by reducing the temperature to normal temperature, filtering to remove the base, concentrating xylene under reduced pressure, and recrystallizing with 260mL of ethyl acetate.
MS[M+H]+＝774
Production example 9
In a 500mL round-bottom flask under nitrogen, after completely dissolving compound 9- (4'-chloro- [1,1' -biphenyl ] -3-yl) -9H-carbazole (6.68g, 15.53mmol) and compound a9(6.56g, 17.09mmol) in 250mL of xylene, NaOtBu (1.79g, 18.64mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.16g, 0.31mmol) was added, and the mixture was stirred under heating for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 210mL of tetrahydrofuran, thereby producing production example 9(5.36g, yield: 49%).
MS[M+H]+＝702
Production example 10
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving the compound 7- (4'-chloro- [1,1' -biphenyl ] -3-yl) -7H-benzo [ c ] carbazole (6.49g, 16.01mmol) and the compound a10(6.71g, 17.71mmol) in 280mL of xylene, NaOtBu (1.86g, 19.33mmol) was added, and bis (tri-t-butylphosphine) palladium (0) (0.16g, 0.32mmol) was added, followed by stirring with heating for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 320mL of ethyl acetate, thereby producing production example 10(7.56g, yield: 63%).
MS[M+H]+＝745
Production example 11
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving the compound 5- (4'-chloro- [1,1' -biphenyl ] -3-yl) -5H-benzo [ b ] carbazole (5- (4'-chloro- [1,1' -biphenyl ] -3-yl) -5H-benzob ] carbazole) (7.02g, 17.42mmol) and the compound a11(9.20g, 19.16mmol) in 240mL of xylene, NaOtBu (2.01g, 20.90mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.18g, 0.35mmol) was added, and stirring was performed with heating for 4 hours. Production example 11(8.39g, yield: 57%) was produced by reducing the temperature to normal temperature, filtering to remove the base, concentrating xylene under reduced pressure, and recrystallizing with 280mL of ethyl acetate.
MS[M+H]+＝848
Production example 12
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving the compound 11- (4'-chloro- [1,1' -biphenyl ] -3-yl) -11H-benzo [ a ] carbazole (11- (4'-chloro- [1,1' -biphenyl ] -3-yl) -11H-benzoa ] carbazole) (7.56g, 18.76mmol) and the compound a12(8.85g, 20.64mmol) in 240mL of xylene, NaOtBu (2.16g, 22.51mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.19g, 0.38mmol) was added, and stirring was performed with heating for 2 hours. Production example 12(7.79g, yield: 52%) was produced by reducing the temperature to normal temperature, filtering to remove the base, concentrating xylene under reduced pressure, and recrystallizing with 250mL of ethyl acetate.
MS[M+H]+＝798
Production example 13
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving compound 9- (3'-chloro- [1,1' -biphenyl ] -3-yl) -9H-carbazole (6.53g, 18.50mmol) and compound a13(10.28g, 20.35mmol) in 310mL of xylene, NaOtBu (2.13g, 22.20mmol) was added, bis (tri-t-butylphosphine) palladium (0) (0.19g, 0.37mmol) was added, and the mixture was stirred for 4 hours under heating. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 310mL of ethyl acetate, thereby producing production example 13(9.49g, yield: 62%).
MS[M+H]+＝824
[ examples ]
Examples 1 to 1
Indium Tin Oxide (ITO) and a process for producing the same
The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water obtained by twice filtration using a Filter (Filter) manufactured by Millipore Co. Washing the ITO for 30 minutesAfter the lapse of a minute, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode thus prepared as an anode, the compound HI1 and the compound HI2 were added so that the ratio was 98:2 (molar ratio)
The hole injection layer is formed by thermal vacuum deposition. On the hole injection layer, a compound represented by the following chemical formula HT1
Vacuum evaporation is performed to form a hole transport layer. Then, on the hole transport layer, the film thickness
The compound of production example 1 was vacuum-evaporated to form an electron-inhibiting layer. Next, the electron inhibiting layer is formed on the substrate to a film thickness
A compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD are subjected to vacuum evaporation at a weight ratio of 25:1 to form a light-emitting layer. On the light-emitting layer, the thickness of the film
The compound represented by the following chemical formula HB1 was vacuum-evaporated 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 a hole blocking layer
The thickness of (a) forms an electron injection and transport layer. On the above electron injection and transport layer, lithium fluoride (LiF) is sequentially added to
Thickness of aluminum and
the thickness of (3) is evaporated to form a cathode.
In the above process, the evaporation speed of the organic material is maintained
Lithium fluoride maintenance of cathode
Deposition rate of (3), aluminum maintenance
The vapor deposition rate of (2) is maintained at a vacuum degree of 2X 10 during vapor deposition-7～5×10-6And supporting to thereby fabricate an organic light emitting device.
Examples 1-2 to examples 1-13
An organic light-emitting device was produced 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 production example 1.
Comparative examples 1-1 to 1-6
An organic light-emitting device was produced 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 production example 1. The compounds of EB1, EB2, EB3, EB4, EB5 and EB6 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, the 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 nits) to 95%.
[ Table 1]
As shown in table 1 above, the organic light emitting device using the compound of the present invention as an electron inhibiting layer shows excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device.
In contrast, as shown in comparative examples 1-1 to 1-4, it was confirmed that when a compound in which a biphenyl carbazolyl group and an amine group are bonded and no adamantyl substituent is contained in the amine group is used, the voltage is increased, the efficiency is lowered, and the compound shows a significantly inferior characteristic in stability as compared with examples.
In addition, based on comparative examples 1 to 5 and 1 to 6, it was confirmed that even when the adamantyl substituent was included, the compound having a different bonding position between the carbazolyl group and the amine group from the compound of the present invention could not realize the excellent device characteristics of the present invention based on the phenyl group on the carbazole side of the biphenyl linking group.
[ description of symbols ]
1: substrate 2: anode
3: organic material layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: electron suppression layer 8: luminescent layer
9: hole-inhibiting layer 10: electron transport layer
11: an electron injection layer.
Claims (8)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1, the first and second organic solvents,
R1to R4Are each hydrogen or deuterium, or R1To R4Two adjacent of them are combined to form a benzene ring, and the rest is hydrogen or deuterium,
L1to L3Each independently is a single bond; substituted or unsubstituted C6-60An arylene group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60A heteroarylene group, a heteroaryl group,
Ar1is substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C comprising any one or more selected from N, O and S2-60A heteroaryl group.
2. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulae 1-1 to 1-4:
chemical formula 1-1
Chemical formula 1-2
Chemical formulas 1 to 3
Chemical formulas 1 to 4
In the chemical formulas 1-1 to 1-4, L1To L3And Ar1As defined in claim 1.
3. The compound of claim 1, wherein Ar1Is any one selected from the following groups:
in the context of the group in question,
x is NR'4The oxygen, the oxygen or the sulfur is selected from the group consisting of O and S,
R'1to R'4Each independently hydrogen, substituted or unsubstituted C1-10Alkyl, or substituted or unsubstituted C6-12And (4) an aryl group.
4. The compound of claim 1, wherein L1To L3Each independently is a single bond; substituted or unsubstituted C6-30An arylene group; or substituted or unsubstituted C containing an O or S heteroatom2-30A heteroarylene group.
5. The compound of claim 1, wherein L1Is a single bond, phenylene, biphenylene or naphthylene.
6. The compound of claim 1, wherein L2And L3Each independently a single bond or phenylene.
7. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of:
8. an organic light emitting device, comprising: a first electrode; a second electrode provided so as to face the first electrode; and an organic layer having 1 or more layers between the first electrode and the second electrode, wherein 1 or more layers of the organic layer contain the compound according to any one of claims 1 to 7.
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