CN112334472A - Novel compound and organic light emitting device comprising same - Google Patents
Novel compound and organic light emitting device comprising same Download PDFInfo
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- CN112334472A CN112334472A CN201980042862.1A CN201980042862A CN112334472A CN 112334472 A CN112334472 A CN 112334472A CN 201980042862 A CN201980042862 A CN 201980042862A CN 112334472 A CN112334472 A CN 112334472A
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Abstract
The invention provides a novel compound and an organic light-emitting element using the same.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2018-0093318, 8/9/2018 and korean patent application No. 10-2019-0096889, 8/2019, including the entire disclosures in the documents of the korean patent application as part of the present specification.
The present invention relates to a novel heterocyclic compound and an organic light-emitting element including the same.
The present invention relates to a novel compound and an organic light-emitting device using 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 element 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 element generally has a structure including an anode and a cathode, and an organic layer located 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. In the structure of such an organic light emitting element, if a voltage is applied between the electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, which emit light when they transition to the ground state again.
Development of new materials for organic materials used in the organic light-emitting devices described above is continuously demanded.
Documents of the prior art
Patent document
(patent document 0001) Korean patent laid-open publication No. 10-2013-073537
Disclosure of Invention
Problems to be solved
The present invention relates to a novel compound and an organic light emitting device including 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,
l is a direct bond, substituted or unsubstituted C1-60Alkylene, or substituted or unsubstituted C6-60An arylene group, a cyclic or cyclic alkylene group,
ar is substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
R1and R2Each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60Haloalkyl, substituted or unsubstituted C1-60Haloalkoxy, tri (C)1-60Alkyl) silyl groupsOr substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
a1 is an integer from 0 to 7,
a2 is an integer of 0 to 5,
C1to C4Wherein adjacent two carbons are each connected to one of chemical formula 2,
[ chemical formula 2]
In the above-described chemical formula 2,
y is O, S, CR4R5Or NR6，
R4And R5Each independently is substituted or unsubstituted C1-60An alkyl group, a carboxyl group,
R6is substituted or unsubstituted C1-60Alkyl, or substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
R3each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60Haloalkyl, substituted or unsubstituted C1-60Haloalkoxy, tri (C)1-60Alkyl) silyl, or substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
a3 is an integer from 0 to 4.
In addition, the present invention provides an organic light emitting element including: a first electrode, a second electrode provided so as to face 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 contain the compound of the present invention.
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 element in which improvement of efficiency, low driving voltage, and/or improvement of life 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, light emission, electron transport, or electron injection.
Drawings
Fig. 1 shows an example of an organic light-emitting element including a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4.
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 following chemical formula 1.
[ chemical formula 1]
In the above-described chemical formula 1,
l is a direct bond, substituted or unsubstituted C1-60Alkylene, or substituted or unsubstituted C6-60An arylene group, a cyclic or cyclic alkylene group,
ar is substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
R1and R2Each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60Haloalkyl, substituted or unsubstituted C1-60Haloalkoxy, tri (C)1-60Alkyl) silyl, or substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
a1 is an integer from 0 to 7,
a2 is an integer of 0 to 5,
C1to C4Wherein adjacent two carbons are each connected to one of chemical formula 2,
[ chemical formula 2]
In the above-described chemical formula 2,
y is O, S, CR4R5Or NR6，
R4And R5Each independently is substituted or unsubstituted C1-60An alkyl group, a carboxyl group,
R6is substituted or unsubstituted C1-60Alkyl, or substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
R3each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60Haloalkyl, substituted or unsubstituted C1-60Haloalkoxy, tri (C)1-60Alkyl) silyl, or substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
a3 is an integer from 0 to 4.
In the context of the present specification,
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 radicals (A), (B), (C), (D), (
alkyl thio xy); arylthio radicals (A), (B), (C
aryl thio xy); alkylsulfonyl (
alkyl sulfoxy); arylsulfonyl (
aryl sulfoxy); 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 2 or more substituents of the above-exemplified substituents may be bonded to each other to form a substituted or unsubstituted heterocyclic group. 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-, 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. In the case where the above-mentioned fluorenyl group is substituted, it may be
And the like. But is not limited thereto.
In the present specification, the heterocyclic group includes 1 or more of O, N, Si and SThe heterocyclic group which is a hetero atom is not particularly limited in the number of carbon atoms, but preferably has 2 to 60 carbon atoms. 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, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoquinoyl
Azolyl group,
Oxadiazolyl, thiadiazolyl, benzothiazolyl, 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 in addition to this, the above description on the heterocyclic group can be applied.
Preferably, the compound represented by the above chemical formula 1 is any one selected from the group consisting of compounds represented by the following chemical formulae 3 to 8:
[ chemical formula 3]
[ chemical formula 4]
[ chemical formula 5]
[ chemical formula 6]
[ chemical formula 7]
[ chemical formula 8]
In the above chemical formulae 3 to 8, L, Ar, Y, R1、R2、R3A1, a2 and a3 are as defined above.
Preferably, in chemical formula 1, L is a direct bond, phenylene, biphenylene, terphenylene, quaterphenylene, naphthylene, phenanthrylene, triphenylene, phenylene
A mesitylene group, a pyrenylene group, or a triphenylene group.
Further preferably, L is a direct bond, phenylene, biphenylene, or naphthylene, more preferably, L is a direct bond, or phenylene.
Preferably, in chemical formula 1, Ar is phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, triphenylene, or the like,
A phenyl group, a fluoranthenyl group, a pyrenyl group, or a triphenylenyl group.
Further preferably, Ar is phenyl, biphenyl, or terphenyl, more preferably Ar is phenyl.
Preferably, in chemical formula 1, R1And R2Each independently hydrogen.
Preferably, in chemical formula 2, a1 and a2 are integers of 0 to 2, more preferably 0 or 1.
Preferably, in chemical formula 2, R4And R5Each independently is methyl.
Preferably, in chemical formula 2, R6Is phenyl.
Preferably, in chemical formula 2, R3Is hydrogen.
Preferably, in chemical formula 2, a3 is an integer of 0 to 2, more preferably 0 or 1.
Preferably, the compound represented by the above chemical formula 1 is any one selected from the group consisting of:
the compound represented by chemical formula 1 according to the present invention is prepared by reacting at benzene
The bond between the oxazole and the carbazolyl group is formed, whereby the electron stability is increased, and such an effect can be further increased by the interaction with the condensed carbazolyl group. Therefore, when applied to an organic light-emitting element, high efficiency, low driving voltage, high luminance, long life, and the like are achieved.
The compound represented by the above chemical formula 1 may be produced by the following reaction formulas 1-1 to 1-2.
[ reaction formula 1-1]
[ reaction formulae 1-2]
In the above reaction formulae 1-1 to 1-2, the variables other than X are the same as defined above, and X is a halogen, preferably bromine or chlorine. The above reaction formula 1-1 is an amine substitution reaction, and is a reaction for producing the above Sub-Compound (Sub Compound) by a reaction in the presence of a palladium catalyst and a base. The above reaction formula 1-2 is a reaction of reacting reactants in the presence of a palladium catalyst and a base to produce the compound represented by chemical formula 1 of the present invention as a suzuki coupling reaction. The above-described manufacturing method can be further embodied in the manufacturing examples described later.
The production of the compound represented by the above chemical formula 1 and the organic light emitting device comprising the same is specifically described 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.
In addition, the present invention provides an organic light emitting element comprising the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light emitting element, including: the organic light emitting device includes a first electrode, a second electrode provided to face 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 include a compound represented by the 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 element 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 element is not limited to this, and a smaller number of organic layers may be included.
In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport, and the hole injection layer, the hole transport layer, or the layer simultaneously performing hole injection and transport includes the compound represented by the above chemical formula 1.
In addition, the organic layer may include a light emitting layer including the compound represented by the chemical formula 1.
In addition, the organic layer may include an electron transport layer or an electron injection layer including the compound represented by the above chemical formula 1.
In addition, the electron transport layer, the electron injection layer, or the layer simultaneously performing electron injection and electron transport includes the compound represented by the above chemical formula 1. In particular, the compound represented by chemical formula 1 according to the present invention is excellent in thermal stability, and has a deep HOMO level of 6.0eV or more, a high triplet Energy (ET), and hole stability. In addition, when the compound represented by the above chemical formula 1 is used for an organic layer that can simultaneously perform electron injection and electron transport, an n-type dopant used in the art may be mixed and used.
In addition, the organic layer may include a light emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by the chemical formula 1.
The organic light-emitting element according to the present invention may be an organic light-emitting element having a structure in which an anode, 1 or more organic layers, and a cathode (normal type) are sequentially stacked on a substrate. The organic light-emitting element according to the present invention may be an inverted (inverted) type organic light-emitting element in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate. For example, fig. 1 and 2 show an example of the structure of an organic light-emitting element according to an embodiment of the present invention.
Fig. 1 shows an example of an organic light-emitting element including a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be included in the above light emitting layer.
Fig. 2 illustrates an example of an organic light-emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4. 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, light emitting layer, and electron transport layer.
The organic light emitting element according to the present invention may be manufactured by materials and methods known in the art, except that 1 or more of the above organic layers contain the compound represented by the above chemical formula 1. In addition, when the organic light emitting element 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 element according to the present invention can be manufactured by sequentially laminating a first electrode, an organic layer, and a second electrode on a substrate. In this case, the following production can be performed: 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 element.
In addition, when the compound represented by the above chemical formula 1 is used to manufacture an organic light emitting device, the organic layer may be formed not only by a vacuum deposition method but also by a solution coating method. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting element may 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 metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO2And a multilayer structure material such as Al, but not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the following substances 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 light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As an example, there is an 8-hydroxyquinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is
Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.
The light emitting layer may include a host material and a dopant material. The main material has fragranceGroup fused ring derivatives or heterocyclic ring-containing compounds, and the like. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds
Pyrimidine derivatives, etc., but are not limited thereto.
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 substituted with at least 1 arylvinyl group in substituted or unsubstituted arylamines, 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. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.
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 preferably a substance having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq3The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. The electron 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 cesiumBarium, 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 element 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 element.
The production of the compound represented by the above chemical formula 1 and the organic light emitting device comprising the same is specifically described 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: production of intermediate compounds sub 1-1(sub 1-1) to sub 1-2(sub 1-2)
Production of Compound subunit 1-1
The compounds 3-chloro-9H-carbazole (3-chloro-9H-carbazole) (30.0g, 149.2mmol) and 2-chlorobenzo [ d ] are reacted under a nitrogen atmosphere]
Azole (2-chlorobenzol [ d ]]oxazole) (22.9g, 149.2mmol) was added to 300mL of xylene and dissolved, sodium t-butoxide (21.5g, 228.9mmol) was added and heated. Bis (tri-tert-butylphosphino) palladium (2.4g, 3 mol%) was added and stirred under reflux for 12 hours. After the reaction was completed, the temperature was reduced to normal temperature, and the produced solid was filtered. The solid was dissolved in 700mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column using chloroform and ethyl acetate to produce sub 1-1(30.4g, 61%) as a white solid compound.
MS:[M+H]+＝335
2) Production of Compound subunit 1-2
Compound 1-1(30.4g, 90.8mmol), bis (pinacolato) diboron (26.1g, 99.8mmol) and potassium acetate (17.8g, 181.5mmol) were mixed under nitrogen and added to 300ml of diboron
In the alkane, the mixture was heated with stirring. Under reflux, bis (dibenzylideneacetone) palladium (1.5g, 3 mol%) and tricyclohexylphosphine (1.5g, 6 mol%) were added, and the mixture was stirred with heating for 5 hours. After the reaction is finishedAnd cooling to normal temperature and filtering. Water was poured into the filtrate, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. The residue was distilled under reduced pressure and recrystallized from ethanol to give compound (1-2) (29.8g, 77%).
MS:[M+H]+＝427
Production example 2: production of intermediate compounds sub 2-1(sub 2-1) to sub 2-2(sub 2-2)
1) Production of Compound 2-1
The compounds 3-chloro-9H-carbazole (3-chloro-9H-carbazole) (30.0g, 149.2mmol) and 2- (4-bromophenyl) benzo [ d ] are reacted under a nitrogen atmosphere]
Oxazole (2- (4-bromophenyl) benzol [ d]oxaz ole) (40.8g, 149.2mmol) was added to 300mL of xylene and dissolved, sodium t-butoxide (21.5g, 228.9mmol) was added and heated. Bis (tri-tert-butylphosphino) palladium (2.4g, 3 mol%) was added and stirred under reflux for 12 hours. After the reaction was completed, the temperature was reduced to normal temperature, and the produced solid was filtered. The solid was dissolved in 700mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was stirred and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by passing through a silica gel column using chloroform and ethyl acetate, to thereby produce a white solid compound, sub 2-1(36.1g, 59%).
MS:[M+H]+＝411
2) Production of Compound subunit 2-2
Compound 2-1(36.1g, 88.1mmol), bis (pinacolato) diboron (24.9g, 96.9mmol) and potassium acetate (17.3g, 176.1mmol) were mixed under nitrogen and added to 300ml of diboron
In the alkane, the mixture was heated with stirring. Under reflux, bis (dibenzylideneacetone) palladium (1.5g, 3 mol%) and tricyclohexylphosphine (1.5g, 6 mol%) were added, and the mixture was stirred with heating for 5 hours. After the reaction is finished, the temperature is reduced to normal temperature and then the mixture is filtered. Water was poured into the filtrate, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. The residue was distilled under reduced pressure and recrystallized from ethanol to obtain compound 2-2(29.2g, 66%).
MS:[M+H]+＝503
Production example 3: production of Compounds 1 to 6
1) Production of Compound 1
The compound 2-bromo-7,7-dimethyl-5-phenyl-5, 7-dihydroindeno [2,1-b ] carbazole (2-bromo-7,7-dimethyl-5-phenyl-5, 7-dihydro-indeno [2,1-b ] carbazole) (17.4g, 39.8mmol) was added to 200ml of tetrahydrofuran under nitrogen atmosphere, stirred and refluxed. Then, potassium carbonate (16.5g, 119.5mmol) was dissolved in 50ml of water and added, and after sufficiently stirring, tetrakis (triphenylphosphine) palladium (1.4g, 3 mol%) was added. After 4 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was dissolved in chloroform, extracted with water, and the organic layer was dried over magnesium sulfate. Then, the organic layer was dried and recrystallized from ethyl acetate, thereby producing compound 1(16.4g, 56%).
MS:[M+H]+＝734
2) Production of Compound 2
The compound 2-bromo-5,8-diphenyl-5,8-dihydroindolo [2,3-c ] carbazole (2-bromo-5,8-diphenyl-5,8-dihydroindolo [2,3-c ] carbazole) (19.4g, 39.8mmol) was added to 200ml of tetrahydrofuran under a nitrogen atmosphere, stirred and refluxed. Then, potassium carbonate (16.5g, 119.5mmol) was dissolved in 50ml of water and added, and after stirring well, tetrakis (triphenylphosphine) palladium (1.4g, 3 mol%) was added. After 4 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was dissolved in chloroform, extracted with water, and the organic layer was dried over magnesium sulfate. Then, the organic layer was dried and recrystallized from ethyl acetate, thereby producing compound 2(13.1g, 42%).
MS:[M+H]+＝783
3) Production of Compound 3
The compound 2-2(20.0g, 39.8mmol), 11-bromo-8-phenyl-8H-benzofuro [2,3-c ] carbazole (11-bromo-8-phenyl-8H-benzofuro [2,3-c ] carbozole) (16.4g, 39.8mmol) was added to 200ml of tetrahydrofuran under nitrogen atmosphere, stirred and refluxed. Then, potassium carbonate (16.5g, 119.5mmol) was dissolved in 50ml of water and added, followed by addition of tetrakis (triphenylphosphine) palladium (1.4g, 3 mol%) after sufficient stirring. After 4 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was dissolved in chloroform, extracted with water, and the organic layer was dried over magnesium sulfate. Then, the organic layer was dried and recrystallized from ethyl acetate, thereby producing compound 3(12.4g, 44%).
MS:[M+H]+＝708
4) Production of Compound 4
The compound 2-2(20.0g, 39.8mmol), 3-bromo-12-phenyl-12H-benzofuro [2,3-a ] carbazole (3-bromo-12-phenyl-12H-benzofuro [2,3-a ] carbozole) (16.4g, 39.8mmol) was added to 200ml of tetrahydrofuran under nitrogen atmosphere, stirred and refluxed. Then, potassium carbonate (16.5g, 119.5mmol) was dissolved in 50ml of water and added, followed by addition of tetrakis (triphenylphosphine) palladium (1.4g, 3 mol%) after sufficient stirring. After 4 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was dissolved in chloroform, extracted with water, and the organic layer was dried over magnesium sulfate. Then, the organic layer was dried and recrystallized from ethyl acetate, thereby producing compound 4(10.1g, 36%).
MS:[M+H]+＝708
5) Production of Compound 5
The compound 2-2(20.0g, 39.8mmol), 3-bromo-12-phenyl-12H-benzo [4,5] thieno [2,3-a ] carbazole (3-bromo-12-phenyl-12H-benzo [4,5] thieno [2,3-a ] carbozole) (17.0g, 39.8mmol) was added to 200ml of tetrahydrofuran under nitrogen atmosphere, stirred and refluxed. Then, potassium carbonate (16.5g, 119.5mmol) was dissolved in 50ml of water and added, followed by addition of tetrakis (triphenylphosphine) palladium (1.4g, 3 mol%) after sufficient stirring. After 4 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was dissolved in chloroform, extracted with water, and the organic layer was dried over magnesium sulfate. Then, the organic layer was dried and recrystallized from ethyl acetate, thereby producing compound 5(16.7g, 58%).
MS:[M+H]+＝724
6) Production of Compound 6
The compound 1-2-bromo-7, 7-dimethyl-5-phenyl-5, 7-dihydroindeno [2,1-b ] carbazole (2-bromo-7,7-dimethyl-5-phenyl-5, 7-dihydro-indeno [2,1-b ] carbazole) (20.5g, 46.9mmol) was added to 200ml of tetrahydrofuran under nitrogen atmosphere, stirred and refluxed. Then, potassium carbonate (19.5g, 140.8mmol) was dissolved in 60ml of water and added, followed by addition of tetrakis (triphenylphosphine) palladium (1.6g, 3 mol%) after sufficient stirring. After 4 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was dissolved in chloroform, extracted with water, and the organic layer was dried over magnesium sulfate. Then, the organic layer was dried and recrystallized from ethyl acetate, thereby producing compound 6(12.3g, 40%).
MS:[M+H]+＝658
[ Experimental example ]
< Experimental example 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. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone and 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, the following HI-1 compound was added
The hole injection layer is formed by thermal vacuum deposition. On the hole injection layer, the following HT-1 compound is added
Is formed by thermal vacuum deposition, and a hole transport layer is formed on the HT-1 deposited film by depositing a HT-2 compound
The electron blocking layer is formed by vacuum evaporation. On the HT-2 deposited film, the compound 1 produced in production example 1, the YGH-1 compound and the phosphorescent dopant YGD-1 were co-deposited at a weight ratio of 44:44:12 to form a light-emitting layer
A thick light emitting layer. On the light-emitting layer, the following ET-1 compound is added
Is formed by vacuum vapor deposition, and on the electron transport layer, the following ET-2 compound and Li are formed by vacuum vapor deposition at a weight ratio of 98:2
A thick electron injection layer. On the electron injection layer, to
Aluminum is evaporated to form a cathode.
In the above process, the evaporation speed of the organic material is maintained
Aluminum maintenance
The vapor deposition rate of (2), the degree of vacuum of which is maintained at 1X 10 during vapor deposition-7～5×10-8And (4) supporting.
< Experimental examples 2 to 6>
An organic light-emitting element was produced in the same manner as in experimental example 1, except that in experimental example 1, the compounds described in table 1 below were used instead of compound 1 of production example 1.
< comparative Experimental examples 1 to 2>
An organic light-emitting element was produced in the same manner as in experimental example 1, except that in experimental example 1, the compounds described in table 1 below were used instead of compound 1 of production example 1. The compounds of CE1 to CE3 of table 1 below are shown below.
In the above experimental examples and comparative experimental examples, the organic light emitting element was set at 10mA/cm2The voltage and efficiency were measured at a current density of 50mA/cm2The lifetime was measured at the current density of (2), and the results are shown in table 1 below. At this time, LT95 represents the time required for 95% of the initial luminance.
[ TABLE 1]
As shown in table 1, it was confirmed that when the compound of the present invention was used as a light-emitting layer material, the driving voltage was low, and the efficiency and lifetime characteristics were remarkably excellent, as compared with comparative experimental examples. This is due to the fact that by using benzene in
A bond is formed between the oxazole and the carbazolyl group, whereby electron stability is increased, and at the same time, electron stability is increased by interaction with the condensed carbazolyl group.
Description of the symbols
1: substrate 2: anode
3: light-emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: light-emitting layer 8: an electron transport layer.
Claims (11)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1, the first and second organic solvents,
l is directly bonded, substituted or notSubstituted C1-60Alkylene, or substituted or unsubstituted C6-60An arylene group, a cyclic or cyclic alkylene group,
ar is substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
R1and R2Each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60Haloalkyl, substituted or unsubstituted C1-60Haloalkoxy, tri (C)1-60Alkyl) silyl, or substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
a1 is an integer from 0 to 7,
a2 is an integer of 0 to 5,
C1to C4Wherein adjacent two carbons are linked to the following chemical formula 2,
chemical formula 2
In the chemical formula 2,
y is O, S, CR4R5Or NR6，
R4And R5Each independently is substituted or unsubstituted C1-60An alkyl group, a carboxyl group,
R6is substituted or unsubstituted C1-60Alkyl, or substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
R3each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-60Alkyl, substituted or unsubstituted C1-60Alkoxy, substituted or unsubstituted C1-60Haloalkyl, substituted or unsubstituted C1-60Haloalkoxy, tri (C)1-60Alkyl) silyl, or substituted or unsubstituted C6-60An aryl group, a heteroaryl group,
a3 is an integer from 0 to 4.
2. The compound according to claim 1, wherein the compound represented by chemical formula 1 is any one selected from the group consisting of compounds represented by the following chemical formulae 3 to 8:
chemical formula 3
Chemical formula 4
Chemical formula 5
Chemical formula 6
Chemical formula 7
Chemical formula 8
In the chemical formulae 3 to 8, L, Ar, Y, R1、R2、R3A1, a2 and a3 are as defined in claim 1.
3. The compound of claim 1, wherein L is a direct bond, phenylene, biphenylene, terphenylene, quaterphenylene, naphthylene, phenanthryleneTriphenylene, phenylene
A mesitylene group, a pyrenylene group, or a triphenylene group.
4. The compound of claim 1, wherein Ar is phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, triphenylene, or,
A phenyl group, a fluoranthenyl group, a pyrenyl group, or a triphenylenyl group.
5. The compound of claim 1, wherein R1And R2Each independently hydrogen.
6. The compound of claim 1, wherein R4And R5Each independently is methyl.
7. The compound of claim 1, wherein R6Is phenyl.
8. The compound of claim 1, wherein R3Is hydrogen.
9. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of:
10. an organic light-emitting element, comprising: a first electrode, a second electrode provided so as to face 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 contain the compound according to any one of claims 1 to 9.
11. The organic light-emitting element according to claim 10, wherein the organic layer containing the compound is a light-emitting layer.
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