WO2017056205A1 - Nouveau composé imidazole, matériau pour dispositif électronique, élément électroluminescent, et dispositif électronique - Google Patents

Nouveau composé imidazole, matériau pour dispositif électronique, élément électroluminescent, et dispositif électronique Download PDF

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WO2017056205A1
WO2017056205A1 PCT/JP2015/077632 JP2015077632W WO2017056205A1 WO 2017056205 A1 WO2017056205 A1 WO 2017056205A1 JP 2015077632 W JP2015077632 W JP 2015077632W WO 2017056205 A1 WO2017056205 A1 WO 2017056205A1
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electronic device
light
carbon atoms
emitting element
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泰三 八田
廉枋 桑原
純孝 平尾
バヌマシー バラガネサン
賀隆 ▲黄▼
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学校法人君が淵学園
▲いく▼▲雷▼光電科技股▲分▼有限公司
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Priority to JP2017542567A priority Critical patent/JPWO2017056205A1/ja
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants

Definitions

  • the present invention relates to a novel imidazole compound, a material for an electronic device, a light emitting element, and an electronic device, and particularly includes a novel imidazole compound useful as a host material constituting a light emitting layer of a light emitting element such as an organic electroluminescence (EL) element.
  • the present invention relates to an electronic device material, a light emitting element containing the electronic device material, and an electronic device including the light emitting element.
  • Patent Document 1 describes that a 2,4,5-triaryl-substituted imidazole compound and a 1,2,4,5-tetraaryl-substituted imidazole compound are used for a blue fluorescent material.
  • Patent Document 2 describes that a phenylpyridine derivative is used as a light-emitting material, and that a 2,4,5-tris (6-pyridylbiphenyl) imidazole derivative is used as a phosphorescent host material.
  • Patent Document 3 describes that a compound having an electron-accepting group at least at the 1-position or 2-position of imidazole and the other being an electron-donating group is used as a host material.
  • Non-Patent Document 1 includes CBP (4,4′-N, N′-bis (carbazolyl-9-yl) biphenyl) and mCP (1,3-di (carbazolyl-9-yl) benzene) as hosts. It is described to be used as a material.
  • Non-Patent Document 2 describes the use of a benzodifuran derivative as a bipolar host material.
  • a host material in a light-emitting element using a phosphorescent light-emitting material as a light-emitting material (dopant) needs to have a sufficient ability to transport electrons and holes and have high film-forming properties.
  • CBP CBP
  • mCP a well-known host compound
  • the element structure has become a multi-layered structure composed of an extremely large number of layers. Therefore, it is required to simplify the manufacturing process and reduce the cost by lowering the element structure. .
  • a light-emitting element using a benzodifuran derivative described in Non-Patent Document 2 it is possible to realize a single layer or a low layer of an organic layer, but the element structure is special and manufacturing is difficult.
  • the film forming process is limited to the vacuum deposition method, there is a problem that the manufacturing process is complicated. That is, the present condition is that the material for electronic devices which can simplify both an element structure and a manufacturing process has not been found until now.
  • the host material to be used is important. When the stability of the light emitting layer containing the host material is low, there is a problem in the driving stability of the light emitting element for practical use. It becomes.
  • the present invention has been made in view of the above circumstances, and an object thereof is to provide a novel imidazole compound capable of obtaining an electronic device with low driving voltage and high current efficiency when used for forming an electronic device. It is to be. Moreover, it is providing the electronic device material containing this novel imidazole compound, the light emitting element containing this electronic device material, and the electronic device containing the light emitting element.
  • the gist of the present invention is the following (1) to (7).
  • R 1 is an alkyl group, an aromatic heterocyclic group of aromatic hydrocarbon group or a C 1-24 having 1 to 24 carbon atoms having 1 to 24 carbon atoms
  • R 2 is represented by the following general (It is a group shown in Formula (2).)
  • Ar 1 is an aromatic hydrocarbon chain or an aromatic heterocyclic chain
  • Ar 2 is the following general formula (3), (4), (5), (6) or (7). Group represented.
  • Ar 3 and Ar 4 are each independently an aromatic group having 6 to 20 carbon atoms or an aromatic heterocyclic group having 5 to 18 carbon atoms
  • X 1 Is an oxygen atom, a sulfur atom, or a nitrogen atom substituted by an alkyl group, an aromatic hydrocarbon group or an aromatic heterocyclic group
  • X 2 to X 5 are each independently A nitrogen atom or a carbon atom
  • R 3 in the formula (6) and R 4 in the formula (7) are an alkyl group having 1 to 24 carbon atoms, an aromatic hydrocarbon group having 6 to 24 carbon atoms, or a carbon atom, respectively.
  • It is an aromatic heterocyclic group of formula 1 to 24.
  • the novel imidazole compound of the present invention has high material stability and thin film stability when deposited. Therefore, when the electronic device material containing the novel imidazole compound of the present invention is used, for example, when applied to a light emitting element, the light emitting efficiency is improved, the life of the light emitting element is extended, and a display device including such a light emitting element, etc. As a result, the driving voltage and current efficiency of the electronic device can be improved, and the life of the electronic device can be extended.
  • the imidazole compound of the present invention as a host material, it is possible to obtain a light-emitting element that is excellent in low-voltage driving characteristics, stable and has high quantum efficiency.
  • 6 is a graph showing voltage-luminance characteristics of light emitting elements prepared in Examples 7 and 8 and Comparative Example 1. It is a graph which shows the relationship between the current density of the light emitting element produced in Example 7, 8 and the comparative example 1, and current efficiency. 6 is a graph showing voltage-luminance characteristics of light-emitting elements created in Example 9 and Comparative Example 2. It is a graph which shows the relationship between the current density of the light emitting element created in Example 9 and Comparative Example 2, and current efficiency. 6 is a graph showing voltage-luminance characteristics of light-emitting elements created in Example 10 and Comparative Example 3. It is a graph which shows the relationship between the current density of the light emitting element created in Example 10 and Comparative Example 3, and current efficiency.
  • the imidazole compound of the present invention is represented by the following general formula (1).
  • R 1 is an alkyl group, an aromatic heterocyclic group of aromatic hydrocarbon group or a C 1-24 having 6 to 24 carbon atoms having 1 to 24 carbon atoms
  • R 2 is represented by the following general (It is a group shown in Formula (2).)
  • Ar 1 is an aromatic hydrocarbon chain or an aromatic heterocyclic chain
  • Ar 2 is the following general formula (3), (4), (5), (6) or (7). Group represented.
  • Ar 3 and Ar 4 are each independently an aromatic group having 6 to 20 carbon atoms or an aromatic heterocyclic group having 5 to 18 carbon atoms
  • X 1 Is an oxygen atom, a sulfur atom, or a nitrogen atom substituted by an alkyl group, an aromatic hydrocarbon group or an aromatic heterocyclic group
  • X 2 to X 5 are each independently
  • each of R 3 in formula (6) and R 4 in (7) is an alkyl group having 1 to 24 carbon atoms, an aromatic hydrocarbon group having 1 to 24 carbon atoms, or a carbon atom.
  • It is an aromatic heterocyclic group of formula 1 to 24.
  • examples of the alkyl group having 1 to 24 carbon atoms of R 1 include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group.
  • examples thereof include a butyl group, an n-pentyl group, an amyl group, an isoamyl group, a tert-amyl group, a neopentyl group, and an n-hexyl group.
  • an alkyl group having 1 to 12 carbon atoms is preferable, and Groups are more preferred.
  • examples of the aromatic hydrocarbon group having 6 to 24 carbon atoms of R 1 include a monocyclic aromatic hydrocarbon group such as phenyl group and tolyl, phenanthryl group, naphthyl group, anthryl group, fluorenyl group, Examples thereof include condensed polycyclic aromatic hydrocarbon groups such as pyrenyl group and perylenyl group, and ring-linked aromatic hydrocarbon groups such as biphenyl group and terphenyl group. Among them, aromatic hydrocarbon groups having 6 to 20 carbon atoms are preferable. An aromatic hydrocarbon group having 6 to 14 carbon atoms is more preferable.
  • examples of the aromatic heterocyclic group having 1 to 24 carbon atoms represented by R 1 include a pyridyl group, a thienyl group, a furyl group, an oxazolyl group, a thiazolyl group, an oxadiazolyl group, a benzothienyl group, and a dibenzofuryl group.
  • dibenzothienyl group, pyrazinyl group, pyrimidinyl group, pyrazolyl group, imidazolyl group, phenylcarbazolyl group and the like Among them, an aromatic heterocyclic group having 2 to 20 carbon atoms is preferable, and an aromatic group having 3 to 15 carbon atoms is preferred. A group heterocyclic group is more preferred.
  • R 1 is preferably an aromatic hydrocarbon group or an aromatic heterocyclic group from the viewpoint of charge acceptability, and is an aromatic hydrocarbon group having 6 to 14 carbon atoms or an aromatic group having 3 to 15 carbon atoms.
  • a group heterocyclic group is more preferred.
  • R 2 is a group represented by the general formula (2).
  • examples of the aromatic hydrocarbon chain of Ar 1 include a divalent chain derived from benzene (phenyl chain) and a divalent chain derived from polycyclic aromatic hydrocarbon (polycyclic aromatic). Group hydrocarbon chain), and bivalent chains (biphenyl chains) derived from biphenyl such as 4,4′-biphenylylene.
  • the aromatic hydrocarbon chain has preferably 6 to 20 carbon atoms, more preferably 6 to 18 carbon atoms, and particularly preferably 6 to 14 carbon atoms.
  • Ar 1 examples include a divalent chain derived from imidazole, furan, thiophene, pyrrole, pyridine and the like.
  • Ar 1 is preferably a phenyl chain or a polycyclic aromatic hydrocarbon chain, and more preferably a phenyl chain.
  • Ar 2 is a group represented by the above general formulas (3) to (7).
  • examples of the aromatic group having 6 to 20 carbon atoms of Ar 3 and Ar 4 include a monocyclic aromatic hydrocarbon group such as phenyl group and tolyl, phenanthryl group, naphthyl group, anthryl group, Examples thereof include condensed polycyclic aromatic hydrocarbon groups such as fluorenyl group, pyrenyl group and perylenyl group, and ring-linked aromatic hydrocarbon groups such as biphenyl group and terphenyl group. Among them, aromatic carbon atoms having 6 to 20 carbon atoms are included. A hydrogen group is preferred, and an aromatic heterocyclic group having 3 to 15 carbon atoms is more preferred.
  • Examples of the aromatic heterocyclic group having 5 to 18 carbon atoms of Ar 3 and Ar 4 include, for example, pyridyl group, thienyl group, furyl group, oxazolyl group, thiazolyl group, oxadiazolyl group, benzothienyl group, dibenzofuryl group, dibenzothienyl group Group, pyrazinyl group, pyrimidinyl group, pyrazolyl group, imidazolyl group, phenylcarbazolyl group and the like. Among them, an aromatic heterocyclic group having 2 to 20 carbon atoms is preferable, and an aromatic heterocyclic ring having 3 to 15 carbon atoms Groups are more preferred. In formula (3), Ar 3 and Ar 4 may be the same or different.
  • X 1 is an oxygen atom, a sulfur atom, or a nitrogen atom substituted by an alkyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group.
  • alkyl group include the above-described alkyl group having 1 to 24 carbon atoms.
  • aromatic hydrocarbon group include the above-described aromatic hydrocarbon group having 1 to 24 carbon atoms.
  • cyclic group include the above-described aromatic heterocyclic groups having 1 to 24 carbon atoms, and preferred groups are also the same.
  • X 1 is preferably an oxygen atom, a sulfur atom, or a nitrogen atom substituted by an aromatic hydrocarbon group.
  • X 2 to X 5 are nitrogen atoms or carbon atoms, and in the formula (4), X 2 to X 5 may be the same or different. Among them, it is more preferable that all of X 2 to X 5 are carbon atoms or one is a nitrogen atom.
  • X 2 to X 5 are the same as in the general formula (4).
  • Specific examples of the group represented by the general formula (5) include the groups listed below.
  • the alkyl group having 1 to 24 carbon atoms, the aromatic hydrocarbon group having 1 to 24 carbon atoms, and the aromatic heterocyclic group having 1 to 24 carbon atoms represented by R 3 include the above general formula (1 ) And the same groups as mentioned above, and preferred groups are also the same.
  • the alkyl group having 1 to 24 carbon atoms, the aromatic hydrocarbon group having 1 to 24 carbon atoms, and the aromatic heterocyclic group having 1 to 24 carbon atoms represented by R 4 include the above general formula (1 ) And the same groups as mentioned above, and preferred groups are also the same.
  • imidazole compound represented by the general formula (1) include, for example, compounds listed below.
  • the imidazole compound represented by the general formula (1) is, for example, J. Org. Chem, 1937, 2, 319 and the like can be produced by a known general method. Furthermore, the substituent of the imidazole compound can be introduced using a known reaction method such as Suzuki coupling or Sonogashira coupling.
  • the imidazole compound of the present invention can be suitably used as a material for electronic devices in light emitting elements, organic thin film solar cells and the like. Specifically, for example, it can be suitably used as a host material contained in a light emitting layer of a light emitting element such as a light emitting diode used for an organic EL display, organic EL illumination, or the like.
  • the electronic device material of the present invention contains the imidazole compound of the present invention usually in an amount of 1 to 100% by weight.
  • a known solvent, other light emitting materials, other host materials, additives and the like may be contained in the range of 0 to 99% by weight.
  • the electronic device of the present invention includes a light emitting element, for example, a light emitting element having a cathode and an anode, and a light emitting layer interposed between these electrodes.
  • light emitting elements include organic EL elements.
  • organic EL elements holes from the anode and electrons from the cathode are injected into the light emitting layer, and they recombine in the light emitting layer to generate excitons, which emit light when they are deactivated.
  • This organic EL element can be applied to electronic devices such as a light emitting light source, a lighting device, and a display device.
  • the cathode, anode, and other materials constituting the light emitting layer of the organic EL element can be appropriately selected from known materials and used.
  • the element may include an electron transport layer including an electron transport material between the cathode and the light emitting layer, and a hole transport layer including a hole transport material between the anode and the organic thin film layer. It may be.
  • electron transporting material and hole transporting material known materials can be appropriately used.
  • the imidazole compound of the present invention can be suitably used as a light emitting material (dopant material) or a host material contained in the light emitting layer as a material for electronic devices.
  • the compound having the lowest mixing ratio (mass ratio) is the light emitting material
  • the compound having the highest mixing ratio (mass ratio) is the host material.
  • compound A is a light emitting material compound
  • compound B is a host compound.
  • compound A is a light emitting material compound
  • compound C is a host compound.
  • the imidazole compound of the present invention can be applied to a hole transport material or an electron transport material as a carrier transport, injection material, or carrier block material.
  • the electronic device material contains the novel imidazole compound of the present invention
  • a light-emitting element by forming a thin film on a substrate by a coating method such as a solution coating method, a melt coating method, or a vapor deposition method. It is.
  • a method of forming a light-emitting layer of a light-emitting element using the electronic device material of the present invention a method of applying a solution of the electronic device material on a substrate, and depositing the electronic device material on the substrate And a method in which the electronic device material is melted and applied onto a substrate.
  • Such a substrate examples include known substrates generally used for electronic devices, such as glass, quartz, sapphire, silicon, silicon carbide, polyethylene terephthalate, polyethylene naphthalate, polyether sulfone, polyimide, polyaramid, and cycloolefin polymers. And polycarbonate.
  • Such a substrate may have a transparent conductive layer such as ITO.
  • Examples of the method for applying the solution of the electronic device material of the present invention on the substrate include a spin coating method, a casting method, an inkjet method, and a printing method.
  • Examples of the solvent used in the solution of the electronic device material include aromatic compounds such as toluene and xylene, halogen-containing solvents such as 1,2-dichloroethane and chlorobenzene, ether solvents such as ethylene glycol dimethyl ether, and ethyl acetate. Examples include aliphatic esters, ketone solvents such as acetone and methyl ethyl ketone, amide solvents such as N, N-dimethylformamide, and dimethyl sulfoxide. These may be used alone or in combination of two or more.
  • the light emitting layer is formed by removing the solvent by performing drying by heating, drying under reduced pressure, or the like as necessary.
  • a method for depositing the electronic device material of the present invention on a substrate for example, Sigma-Aldrich “Basics of Material Science” Vol. 1, No. 1
  • the well-known vapor deposition method of 1 is applicable.
  • a melt coating method such as a general melt coating method can be applied.
  • reaction mixture is allowed to cool to room temperature, and the precipitated solid is collected by filtration, washed with methanol, and 2- (3-nitrophenyl) -4,6-diphenyl-1,3,5-triazine (7. 6 g, yield 88%).
  • Example 1 1- (4-Dibenzothiophen-3-ylphenyl) -2-phenyl-1H-phenanthro [9,10-d] imidazole (20.0 g), 4-dibenzothiopheneboronic acid (11.2 g), and tetrakis ( Toluene (160 mL), ethanol (80 mL), and 2M aqueous sodium carbonate solution (160 mL) were added to triphenylphosphine) palladium (0) (1.0 g), and the mixture was heated to reflux for 6 hours. The reaction mixture was allowed to cool to room temperature, and the precipitated solid was collected by filtration.
  • Example 2 Synthesis of 1- (9-phenylcarbazol-3-ylphenyl) -2-phenyl-1H-phenanthro [9,10-d] imidazole 1- (3-Bromophenyl)-obtained in Reference Example 1 under nitrogen atmosphere 2-Phenyl-1H-phenanthro [9,10-d] imidazole (20.0 g), 9-phenylcarbazole-3-boronic acid (14.0 g), and tetrakis (triphenylphosphine) palladium (0) (1.
  • Example 4 Synthesis of 1- [3- (4,6-diphenyl- [1,3,5] triazin-2-yl) phenyl] -2-phenyl-1H-phenanthro [9,10-d] imidazole 1.
  • 1- (3-bromophenyl) -2-phenyl-1H-phenanthro [9,10-d] imidazole (40.0 g) obtained in Reference Example 1 to a dry THF (400 mL) solution.
  • a 6M butyllithium hexane solution (67.0 mL) was added dropwise over 20 minutes.
  • the reaction solution was stirred at ⁇ 70 ° C. for 30 minutes, and trimethyl borate (60.0 mL) was added dropwise over 10 minutes.
  • Example 7 ⁇ Evaluation of light emitting element> TAPC (see the following chemical formula) (40 nm) was formed by vacuum deposition on a patterned ITO substrate (film thickness 110 nm) subjected to patterning to form a hole transport layer. Ir (ppy) 3 (refer to the following chemical formula) and the imidazole compound of Example 1 were formed on this by co-evaporation so as to have a film thickness ratio of 20: 1 to form a light emitting layer (20 nm).
  • TpPyPB (refer to the following chemical formula) (50 nm) is formed, an electron transport layer is formed, lithium fluoride (0.5 nm) and aluminum (100 nm) are formed, a cathode is formed, and the cap glass is used. Sealing was performed to produce a 2 mm square light emitting device. Green light emission was confirmed by applying a voltage to the light emitting element. The element characteristics (driving voltage (V) and current efficiency (cd / A)) of the obtained light-emitting element were measured with an IVL measuring device (“CS-2000” manufactured by Konica Minolta Sensing Co., Ltd.).
  • Example 8 A light emitting device was similarly produced except that the imidazole compound of Example 1 used in Example 7 was replaced with the imidazole compound synthesized in Example 2. Green light emission was confirmed by applying a voltage to the light emitting element. The driving voltage (V) and current efficiency (cd / A) of the obtained light-emitting element were measured in the same manner as in Example 7.
  • Example 1 A light emitting device was similarly produced except that the imidazole compound of Example 1 used in Example 7 was replaced with CBP (see the following chemical formula) which is a general host compound. Green light emission was confirmed by applying a voltage to the light emitting element. The driving voltage (V) and current efficiency (cd / A) of the obtained light-emitting element were measured in the same manner as in Example 7.
  • Table 1 shows the driving voltage and current efficiency at 1,000 cd / m 2 of the light emitting devices manufactured in Examples 7 and 8 and Comparative Example 1 described above. A comparison of light emission luminance-voltage characteristics and current efficiency-current density of these light-emitting elements is shown in FIGS.
  • Example 9 HAT-CN (refer to the following chemical formula) (1 nm) (1 nm) and then HT1 (refer to the following chemical formula) (40 nm) are formed on the cleaned ITO substrate (film thickness 110 nm) subjected to patterning by vacuum deposition, A hole transport layer was formed. Ir (ppy) 3 and the imidazole compound of Example 4 were formed into a film by co-evaporation so that the film thickness ratio was 1:20, thereby forming a light emitting layer (20 nm).
  • ET1 and Liq were formed by co-evaporation so that the film thickness ratio was 1: 1, and after forming an electron transport layer (50 nm), lithium fluoride (0.5 nm) and aluminum ( 100 nm) was formed to form a cathode and sealed with cap glass to produce a 2 mm square light emitting device. Green light emission was confirmed by applying a voltage to the light emitting element.
  • the driving voltage (V) and current efficiency (cd / A) of the obtained light-emitting element were measured in the same manner as in Example 7.
  • Example 2 A light emitting device was similarly produced except that the imidazole compound of Example 4 used in Example 9 was replaced with CBP which is a general host compound. Green light emission was confirmed by applying a voltage to the light emitting element. The driving voltage (V) and current efficiency (cd / A) of the obtained light-emitting element were measured in the same manner as in Example 7.
  • Table 2 shows the driving voltage and current efficiency at 1,000 cd / m 2 of the light emitting devices manufactured in Example 9 and Comparative Example 2 described above. 3 and 4 show a comparison of light emission luminance-voltage characteristics and current efficiency-current density of these light-emitting elements.
  • Example 10 HAT-CN (1 nm) and then HT1 (40 nm) were formed by vacuum deposition on a patterned ITO substrate (thickness 150 nm) subjected to patterning to form a hole injection layer and a hole transport layer.
  • Ir (pic) 3 (refer to the following chemical formula) and the imidazole compound of Example 5 were formed on this by co-evaporation so as to have a film thickness ratio of 1:20 to form a light emitting layer (20 nm).
  • ET1 and Liq were formed by co-evaporation so as to have a film thickness ratio of 1: 1, an electron transport layer (50 nm) was formed, and then lithium fluoride (0.5 nm) and aluminum (100 nm) were formed.
  • Example 3 A light emitting device was similarly produced except that the imidazole compound of Example 5 used in Example 10 was replaced with CBP which is a general host compound. Red light emission was confirmed by applying a voltage to the light emitting element. The driving voltage (V) and current efficiency (cd / A) of the obtained light-emitting element were measured in the same manner as in Example 7.
  • Table 3 shows the driving voltage and current efficiency at 1,000 cd / m 2 of the light emitting devices manufactured in Example 10 and Comparative Example 3 above. Comparison of light emission luminance-voltage characteristics and current efficiency-current density of these light-emitting elements is shown in FIGS.
  • the electronic device material containing the novel imidazole compound of the present invention can be used for various electronic devices such as light-emitting elements and organic thin-film solar cells.
  • various electronic devices including light-emitting elements such as organic EL elements, more specifically, flat panel displays (for example, computer displays and wall-mounted televisions) and surface-emitting body light sources (for example, lighting, light sources for copying machines) , Liquid crystal display backlight light source, instrument backlight light source), display boards, beacon lamps and other electronic devices.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La présente invention vise à fournir un nouveau composé imidazole, permettant d'obtenir un dispositif électronique ayant une faible tension d'entraînement et une grande efficacité de courant électrique lorsque le nouveau composé imidazole est utilisé pour former le dispositif électronique. Ce composé imidazole est représenté par la formule générale (1). (dans la formule (1), R1 et R2 sont chacun identiques à ceux décrits dans la description.)
PCT/JP2015/077632 2015-09-29 2015-09-29 Nouveau composé imidazole, matériau pour dispositif électronique, élément électroluminescent, et dispositif électronique WO2017056205A1 (fr)

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PCT/JP2015/077632 WO2017056205A1 (fr) 2015-09-29 2015-09-29 Nouveau composé imidazole, matériau pour dispositif électronique, élément électroluminescent, et dispositif électronique

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