WO2014030554A1 - Composé ayant un groupe triphénylsilyl pyridyle et une structure de noyau carbazole et un dispositif électroluminescent organique - Google Patents

Composé ayant un groupe triphénylsilyl pyridyle et une structure de noyau carbazole et un dispositif électroluminescent organique Download PDF

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WO2014030554A1
WO2014030554A1 PCT/JP2013/071624 JP2013071624W WO2014030554A1 WO 2014030554 A1 WO2014030554 A1 WO 2014030554A1 JP 2013071624 W JP2013071624 W JP 2013071624W WO 2014030554 A1 WO2014030554 A1 WO 2014030554A1
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compound
substituted
light emitting
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紀昌 横山
長岡　誠
大三 神田
幸喜 加瀬
結 市川
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保土谷化学工業株式会社
国立大学法人信州大学
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Definitions

  • the present invention relates to a compound suitable for an organic electroluminescence element which is a self-luminous element suitable for various display devices and the element, and more specifically, a compound having a triphenylsilylpyridyl group and a carbazole ring structure, and the compound The present invention relates to an organic electroluminescence device using the above.
  • the organic electroluminescence element is a self-luminous element, it has been actively researched because it is brighter and more visible than a liquid crystal element and has a clear display.
  • CBP 4,4′-di (N-carbazolyl) biphenyl
  • CBP has a low glass transition point (Tg) as low as 62 ° C. and strong crystallinity, so that it has poor stability in a thin film state. Therefore, satisfactory device characteristics have not been obtained in scenes where heat resistance is required, such as high luminance light emission.
  • the excited triplet level of the host compound is higher than the excited triplet level of the phosphorescent emitter. It has become clear that it must be high.
  • FIrpic which is a blue phosphorescent light emitting material represented by the following formula
  • the external quantum efficiency of the phosphorescent light emitting element remains at about 6%. This is because the excited triplet level of FIrpic is 2.67 eV, whereas the excited triplet level of CBP is as low as 2.57 eV, so that confinement of triplet excitons by FIrpic is insufficient with CBP. It was considered. This is demonstrated by the fact that the photoluminescence intensity of a thin film doped with FIrpic in CBP shows temperature dependence. (For example, see Non-Patent Document 2)
  • mCP 1,3-bis (carbazol-9-yl) benzene
  • the object of the present invention is to have a high excited triplet level as a material for a highly efficient organic electroluminescence device, to sufficiently confine triplet excitons of a phosphorescent emitter, and to have high thin film stability. That is, it is to provide a host compound of a light emitting layer having a high glass transition point (Tg), and to provide a high-efficiency, high-brightness organic electroluminescence device using this compound.
  • Tg glass transition point
  • the physical properties that the organic compound to be provided by the present invention should have include (1) high excitation triplet level, (2) bipolar transportability, and (3) stable thin film state. I can give you.
  • the physical characteristics that the organic electroluminescence device to be provided by the present invention should have include (1) high luminous efficiency, (2) high emission luminance, and (3) low practical driving voltage. I can give you something.
  • the present inventors have confirmed that the triphenylsilyl group and the pyridine ring structure have an electron transporting ability, and that the carbazole ring structure has a good heat resistance and a hole transporting ability.
  • a new compound with characteristics suitable for phosphorescent light emitting devices by designing and chemically synthesizing compounds using the excited triplet level as an indicator, and actually measuring the excited triplet level.
  • a compound having a triphenylsilylpyridyl group and a carbazole ring structure was found. Then, various organic electroluminescence devices were prototyped using the compound, and the characteristics of the devices were intensively evaluated. As a result, the present invention was completed.
  • the present invention provides a compound having a triphenylsilylpyridyl group represented by the following general formula (1) and a carbazole ring structure.
  • R 1 to R 10 may be the same or different, and may be a hydrogen atom, a deuterium atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms, or the number of carbon atoms.
  • Ar represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group
  • L represents a substituted or unsubstituted aromatic group.
  • An aromatic hydrocarbon, a substituted or unsubstituted aromatic heterocyclic ring or a substituted or unsubstituted condensed polycyclic aromatic divalent group or trivalent group is represented, and n represents 1 or 2.
  • the compound having a triphenylsilylpyridyl group and a carbazole ring structure described in 1) above is preferably a compound represented by the following general formula (1-1).
  • L is preferably a divalent group or a trivalent group formed by removing two or three hydrogen atoms from benzene.
  • the present invention also provides a compound having a triphenylsilylpyridyl group and a carbazole ring structure as described in 1) or 2) above, in an organic electroluminescence device having a pair of electrodes and at least one organic layer sandwiched therebetween. Provides an organic electroluminescence element used as a constituent material of the organic layer.
  • the organic layer in 4) above is preferably a light emitting layer.
  • the light emitting layer in the above 5) preferably contains a phosphorescent light emitting material.
  • the organic electroluminescent element according to 4) further includes a light emitting layer sandwiched between the pair of electrodes.
  • the light emitting layer in the above 7) preferably contains a phosphorescent light emitting material.
  • the compound having the triphenylsilylpyridyl group and carbazole ring structure described in 1) or 2) above is at least one component in the light emitting layer. It is preferably used as a material.
  • the phosphorescent light-emitting material is preferably a metal complex containing iridium or platinum.
  • the “6 linear or branched alkoxy group” specifically, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, t-butyl group, n-pentyl group, i-pentyl group, t-pentyl group, n-hexyl group, i-hexyl group, t-hexyl group, methyloxy group, ethyloxy group, n-propyloxy group, i-propyloxy group, n -Butyloxy group, i-butyloxy group, t-butyloxy group, n-pentyloxy group, i-pentyloxy group, t-penty
  • Substituted or unsubstituted aromatic hydrocarbon group or “substituted or unsubstituted aromatic heterocyclic group” represented by R 1 to R 10 in formula (1) and formula (1-1)
  • aromatic hydrocarbon group or “aromatic heterocyclic group” or “fused polycyclic aromatic group” of “substituted or unsubstituted condensed polycyclic aromatic group” specifically includes phenyl group, biphenylyl group , Terphenylyl group, tetrakisphenyl group, styryl group, naphthyl group, anthryl group, acenaphthenyl group, phenanthryl group, fluorenyl group, indenyl group, pyrenyl group, pyridyl group, triazinyl group, pyrimidinyl group, furyl group, pyrrolyl group, thienyl group, Quinolyl, isoquinolyl, benzofuranyl, be
  • Substituted aromatic hydrocarbon group “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic represented by R 1 to R 10 in formula (1) and formula (1-1)
  • substituents in the “group” include a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a linear or branched alkyl group having 1 to 6 carbon atoms, and the number of carbon atoms 1 to 6 linear or branched alkoxy groups, trifluoromethyl group, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, phenanthryl group, aralkyl group, fluorenyl group, indenyl group, pyridyl group, pyrimidinyl group, furyl Group, pyrrolyl group, thienyl group, quinolyl group, benzofuranyl group, be
  • substituted aromatic hydrocarbon group “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by Ar in the general formula (1) and the general formula (1-1)
  • substituents include deuterium atom, fluorine atom, chlorine atom, cyano group, nitro group, linear or branched alkyl group having 1 to 6 carbon atoms, and 1 to 6 carbon atoms.
  • Substituted or unsubstituted aromatic hydrocarbon “substituted or unsubstituted aromatic heterocycle” or “substituted or unsubstituted” represented by L in formula (1) and formula (1-1)
  • aromatic hydrocarbon “aromatic heterocycle” or “fused polycyclic aromatic” of “condensed polycyclic aromatic” include the following groups.
  • substituted or unsubstituted aromatic represented by L in the general formula (1) and the general formula (1-1
  • substituted or unsubstituted aromatic is the above “aromatic hydrocarbon”, “aromatic heterocycle” or “ A divalent group formed by removing two hydrogen atoms from a “fused polycyclic aromatic” or a trivalent group formed by removing three hydrogen atoms.
  • L in the general formula (1) and the general formula (1-1) is preferably a “divalent or trivalent group of a substituted or unsubstituted aromatic hydrocarbon”, particularly a divalent group derived from benzene.
  • a trivalent group is more preferable, and a divalent group derived from benzene is particularly preferable.
  • the compound having a triphenylsilylpyridyl group and a carbazole ring structure represented by the general formula (1) and the general formula (1-1) of the present invention is a novel compound and has a higher excited triplet level than conventional materials. It has an excellent ability to confine triplet excitons and is stable in a thin film state.
  • n represents 1 or 2, and n is more preferably 1.
  • L is a divalent group derived from benzene
  • the bonding position of the triphenylsilylpyridyl group and the carbazole ring structure is 1, 3
  • the -position (meta bond) or 1,2-position (ortho bond) is preferred, and the 1,2-position (ortho bond) is more preferred.
  • the triphenylsilylpyridyl group is preferably any one of the following groups a) to e).
  • the compound having a triphenylsilylpyridyl group and a carbazole ring structure represented by the general formula (1) and the general formula (1-1) of the present invention is an organic electroluminescence device (hereinafter abbreviated as an organic EL device). It can be used as a constituent material of an organic layer, particularly a light emitting layer, more preferably a light emitting layer containing a phosphorescent light emitting material.
  • an organic EL device organic electroluminescence device
  • the compound having a triphenylsilylpyridyl group and a carbazole ring structure according to the present invention is useful as a host compound for a light emitting layer of an organic EL device.
  • an organic EL device By producing an organic EL device using the compound, high efficiency and high brightness can be obtained.
  • An organic EL element with a low driving voltage can be obtained.
  • FIG. 1 is a 1 H-NMR chart of the compound of Example 1 of the present invention (Compound 10).
  • FIG. 2 is a 1 H-NMR chart of the compound of Example 2 of the present invention (Compound 3).
  • FIG. 3 is a diagram showing the EL element configurations of Example 6 and Comparative Example 1.
  • the compound having a triphenylsilylpyridyl group and a carbazole ring structure according to the present invention is a novel compound, and these compounds can be synthesized, for example, as follows.
  • a corresponding carbazolylphenyl intermediate is synthesized by performing a cross-coupling reaction such as Suzuki coupling between the corresponding carbazole derivative and the corresponding halogenated benzene derivative (for example, see Non-Patent Document 4). Can do.
  • the corresponding carbazolylphenyl intermediate is converted into a corresponding borate ester, and then subjected to a cross-coupling reaction such as Suzuki coupling with the corresponding dihalogenated pyridyl derivative, and then the corresponding borate ester
  • a cross-coupling reaction such as Suzuki coupling with the corresponding dihalogenated pyridyl derivative
  • the compound having a triphenylsilylpyridyl group and a carbazole ring structure of the present invention can be synthesized by reacting with lithiated compound or lithiated compound and further with triphenylsilyl chloride.
  • Tg glass transition point
  • work function is an index of the energy level as the light emitting host material.
  • the glass transition point (Tg) was measured with a high sensitivity differential scanning calorimeter (DSC6200, manufactured by Seiko Instruments Inc.) using powder.
  • the work function was measured using an atmospheric photoelectron spectrometer (AC-3 type, manufactured by Riken Keiki Co., Ltd.) by forming a 100 nm thin film on the ITO substrate.
  • the excited triplet level of the compound of the present invention can be calculated from the measured phosphorescence spectrum.
  • the phosphorescence spectrum can be measured using a commercially available spectrophotometer.
  • a general phosphorescence spectrum measurement method a sample is dissolved in a solvent and irradiated with excitation light at a low temperature (for example, see Non-Patent Document 5), or the sample is deposited on a silicon substrate.
  • the excited triplet level can be calculated by reading the wavelength of the first peak on the short wavelength side of the phosphorescence spectrum or the wavelength of the rising position on the short wavelength side and converting it to the light energy value according to the following equation.
  • the excited triplet level is an indicator of the confinement of triplet excitons in the phosphorescent emitter.
  • E is the value of light energy
  • h Planck's constant (6.63 ⁇ 10 ⁇ 34 Js)
  • c is the speed of light (3.00 ⁇ 10 8 m / s)
  • ⁇ is the short wavelength of the phosphorescence spectrum. It represents the wavelength (nm) where the side rises.
  • 1 eV becomes 1.60 ⁇ 10 ⁇ 19 J.
  • an anode As the structure of the organic EL device of the present invention, on the substrate sequentially, an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, a cathode, Further, there may be mentioned those having an electron injection layer between the electron transport layer and the cathode.
  • several organic layers can be omitted.
  • an anode, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode can be sequentially formed on the substrate.
  • Anode, hole transport layer, light emitting layer, electron transport layer, and cathode can be sequentially formed on the substrate.
  • the light emitting layer, the hole transport layer, and the electron transport layer may each have a structure in which two or more layers are stacked.
  • an electrode material having a large work function such as ITO or gold is used.
  • a hole injection layer of the organic EL device of the present invention in addition to a porphyrin compound typified by copper phthalocyanine, a naphthalenediamine derivative, a starburst type triphenylamine derivative, a molecule having three or more triphenylamine structures, Triphenylamine trimers and tetramers such as arylamine compounds having a structure linked by a divalent group containing no bond or hetero atom, acceptor heterocyclic compounds such as hexacyanoazatriphenylene, and coating-type polymers Materials can be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • N, N′-diphenyl-N, N′-di (m-tolyl) -benzidine (hereinafter referred to as “a”)
  • NPD N, N, N ′, N′-tetrabiphenylylbenzidine
  • Benzidine derivatives 1,1-bis [(di-4-tolylamino) phenyl] cyclohexane (hereinafter abbreviated as TAPC), various triphenylamine trimers and tetramers, and carbazole derivatives can be used. . These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used.
  • a coating type such as poly (3,4-ethylenedioxythiophene) (hereinafter abbreviated as PEDOT) / poly (styrene sulfonate) (hereinafter abbreviated as PSS) is used.
  • PEDOT poly (3,4-ethylenedioxythiophene)
  • PSS poly (styrene sulfonate)
  • These polymer materials can be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • a material in which trisbromophenylamine hexachloroantimony is further P-doped to a material usually used in the layer, or a polymer having a TPD structure in its partial structure A compound or the like can be used.
  • TCTA 4,4 ′, 4 ′′ -tri (N-carbazolyl) triphenylamine
  • TCTA 9,9-bis [4- (carbazole- 9-yl) phenyl] fluorene
  • mCP 1,3-bis (carbazol-9-yl) benzene
  • Ad 2,2-bis (4-carbazol-9-ylphenyl) adamantane
  • Carbazole derivatives such as 9- [4- (carbazol-9-yl) phenyl] -9- [4- (triphenylsilyl) phenyl] -9H-fluorene
  • a compound having an electron blocking action such as a compound having a triarylamine structure can be used.
  • These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used.
  • These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • various metal complexes such as metal complexes of quinolinol derivatives including tris (8-hydroxyquinoline) aluminum (hereinafter abbreviated as Alq 3 ), anthracene derivatives, bisstyrylbenzene derivatives , Pyrene derivatives, oxazole derivatives, polyparaphenylene vinylene derivatives, and the like can be used.
  • the light-emitting layer may be composed of a host material and a dopant material.
  • a compound having a triphenylsilylpyridyl group and a carbazole ring structure represented by the general formula (1) of the present invention as the host material, mCP , Thiazole derivatives, benzimidazole derivatives, polydialkylfluorene derivatives, and the like can be used.
  • the dopant material quinacridone, coumarin, rubrene, anthracene, perylene and derivatives thereof, benzopyran derivatives, rhodamine derivatives, aminostyryl derivatives, and the like can be used. These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used.
  • a phosphorescent light emitting material can be used as the light emitting material.
  • a phosphorescent emitter of a metal complex such as iridium or platinum can be used.
  • Green phosphorescent emitters such as Ir (ppy) 3
  • blue phosphorescent emitters such as FIrpic and FIr6, and red phosphorescent emitters
  • Btp 2 Ir (acac) and Ir (piq) 3 are used.
  • a host material a compound having a triphenylsilylpyridyl group and a carbazole ring structure represented by the general formula (1) of the present invention
  • a hole injection / transport host material such as CBP, TCTA, and mCP
  • a carbazole derivative or the like can be used.
  • an electron transporting host material p-bis (triphenylsilyl) benzene (hereinafter abbreviated as UGH2) or 2,2 ′, 2 ′′-(1,3,5-phenylene) -tris (1-phenyl) -1H-benzimidazole) (hereinafter abbreviated as TPBI) and the like can be used.
  • UGH2 triphenylsilyl
  • TPBI 2,2 ′, 2 ′′-(1,3,5-phenylene) -tris (1-phenyl) -1H-benzimidazole
  • the phosphorescent light-emitting material into the host material by co-evaporation in the range of 1 to 30 weight percent with respect to the entire light-emitting layer.
  • These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • an element having a structure in which a light-emitting layer manufactured using a compound having a different work function as a host material is stacked adjacent to a light-emitting layer manufactured using the compound of the present invention can be manufactured (for example, non-patented). Reference 6).
  • phenanthroline derivatives such as bathocuproine (hereinafter abbreviated as BCP), aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate (hereinafter referred to as “BCP”).
  • BCP bathocuproine
  • BCP aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
  • BCP aluminum (III) bis (2-methyl-8-quinolinato) -4-phenylphenolate
  • various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, and the like can be used. These materials may also serve as the material for the electron transport layer.
  • These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used.
  • These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • various metal complexes triazole derivatives, triazine derivatives, oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline, in addition to metal complexes of quinolinol derivatives including Alq 3 and BAlq.
  • Derivatives, phenanthroline derivatives, silole derivatives, benzimidazole derivatives such as TPBI, and the like can be used. These may be formed alone, but may be used as a single layer formed by mixing with other materials, layers formed alone, mixed layers formed, or A stacked structure of layers formed by mixing with a layer formed alone may be used. These materials can be formed into a thin film by a known method such as a spin coating method or an ink jet method in addition to a vapor deposition method.
  • an alkali metal salt such as lithium fluoride and cesium fluoride
  • an alkaline earth metal salt such as magnesium fluoride
  • a metal oxide such as aluminum oxide
  • a material usually used for the layer and further doped with a metal such as cesium can be used.
  • an electrode material having a low work function such as aluminum or an alloy having a lower work function such as a magnesium silver alloy, a magnesium indium alloy, or an aluminum magnesium alloy is used as the electrode material.
  • Tetrakistriphenylphosphinepalladium (2.34 g) was added, and the mixture was heated with stirring and refluxed for 24 hours.
  • the reaction solution was cooled to room temperature, the organic layer was collected by a liquid separation operation, dehydrated with anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain a crude product.
  • the crude product was purified by column chromatography (carrier: silica gel, eluent: hexane / toluene), and 28 g of white powder of 3- (2-bromophenyl) -9-phenyl-9H-carbazole (88% yield) Got.
  • reaction solution was extracted with toluene, dehydrated with anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain a crude product.
  • the crude product was purified by column chromatography (carrier: silica gel, eluent: toluene / methanol) to give 7.8 g of 2- (9-phenyl-9H-carbazol-3-yl) phenylboronic acid white powder (yield). 88%).
  • the reaction solution was cooled to room temperature, the organic layer was collected by a liquid separation operation, dehydrated with anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain a crude product.
  • the crude product was purified by column chromatography (carrier: silica gel, eluent: toluene) and white powder of 3- [2- (5-bromopyridin-2-yl) phenyl] -9-phenyl-9H-carbazole 1.7 g (yield: 43%) was obtained.
  • the organic layer was collected by a liquid separation operation, dehydrated using anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain a crude product.
  • the crude product was purified by column chromatography (carrier: NH silica gel, eluent: ethyl acetate / cyclohexane) and further crystallized to give 3- [2- ⁇ 5- (triphenylsilyl) pyridin-2-yl ⁇ Phenyl] -9-phenyl-9H-carbazole (1.8 g, yield: 17%) was obtained.
  • the reaction solution was cooled to room temperature, the organic layer was collected by a liquid separation operation, dehydrated with anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain a crude product.
  • the crude product was purified by column chromatography (carrier: silica gel, eluent: hexane / toluene), and 23.4 g of 3- (3-bromophenyl) -9-phenyl-9H-carbazole white powder (yield 65 %).
  • the reaction solution was cooled to room temperature, the organic layer was collected by a liquid separation operation, dehydrated with anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain a crude product.
  • the crude product was purified by column chromatography (carrier: NH silica gel, eluent: hexane / toluene) to give 3- ⁇ 3- (5-bromopyridin-2-yl) phenyl ⁇ -9-phenyl-9H-carbazole. 25.1 g (yield: 67%) of white powder was obtained.
  • the organic layer was collected by a liquid separation operation, dehydrated with anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain a crude product.
  • the crude product was purified by column chromatography (carrier: NH silica gel, eluent: hexane / toluene) to give 3- [3- ⁇ 5- (triphenylsilyl) pyridin-2-yl ⁇ phenyl] -9-phenyl- 3.5 g (yield: 10%) of 9H-carbazole white powder was obtained.
  • the compound of the present invention has a glass transition point of 100 ° C. or higher. This indicates that the thin film state is stable in the compound of the present invention.
  • the compound of the present invention shows a suitable energy level as compared with CBP generally used as a luminescent host.
  • the compound of the present invention has a value larger than the triplet energy of commonly used CBP and has the ability to sufficiently confine the triplet energy excited in the light emitting layer.
  • the organic EL element has a hole transport layer 3, a light emitting layer 4, an electron transport layer 5, and an electron injection layer 6 on a glass substrate 1 on which an ITO electrode is previously formed as a transparent anode 2.
  • the cathode (aluminum electrode) 7 was deposited in this order.
  • the glass substrate 1 on which ITO having a thickness of 150 nm was formed was washed with an organic solvent, and then the surface was washed by oxygen plasma treatment. Then, this glass substrate with an ITO electrode was mounted in a vacuum vapor deposition machine and the pressure was reduced to 0.001 Pa or less. Subsequently, TAPC was formed as a hole transport layer 3 so as to cover the transparent anode 2 so as to have a film thickness of 30 nm at a deposition rate of 1.0 kg / sec. On this hole transport layer 3, the compound (compound 10) of Example 1 of the present invention and the green phosphorescent emitter Ir (ppy) 3 are used as the light-emitting layer 4.
  • Example 1 For comparison, the material of the light emitting layer 4 in Example 6 was changed from the compound of Example 1 (Compound 10) to CBP, and an organic EL device was produced under the same conditions. About the produced organic EL element, the characteristic measurement was performed at normal temperature in air
  • the driving voltage when a current density of 10 mA / cm 2 was passed was the compound of Example 1 of the present invention (Compound 10) with respect to 7.7 V of the organic EL device using CBP.
  • the voltage was lowered to 5.9V.
  • the luminance when a current density of 10 mA / cm 2 was passed was greatly improved.
  • luminous efficiency and external quantum efficiency were improved.
  • the compound of the present invention has a high excited triplet level, transfers energy well to the phosphorescent emitter, sufficiently confines the triplet excitons of the phosphorescent emitter, and also has a thin film stability. Since it is good, it can be said that it is excellent as a host compound of the light emitting layer.
  • the compound having a triphenylsilylpyridyl group and a carbazole ring structure of the present invention has a high excited triplet level, can sufficiently confine the triplet exciton of the phosphor, and has good thin film stability. It is excellent as a host compound for the light emitting layer.
  • the luminance and light emission efficiency of the conventional organic EL element can be remarkably improved, and thus the performance of the mobile electronic product can be improved.

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  • Organic Chemistry (AREA)
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Abstract

L'invention concerne un composé ayant un groupe triphénylsilyl pyridyle et une structure de noyau carbazole représenté par la formule générale (1) et un dispositif électroluminescent organique ayant une paire d'électrodes et au moins une couche organique interposée entre elles, ce composé étant utilisé comme matière structurale d'au moins une couche organique.
PCT/JP2013/071624 2012-08-21 2013-08-09 Composé ayant un groupe triphénylsilyl pyridyle et une structure de noyau carbazole et un dispositif électroluminescent organique WO2014030554A1 (fr)

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WO2010052932A1 (fr) * 2008-11-07 2010-05-14 保土谷化学工業株式会社 Composé ayant un groupe triphénylsilyle et une structure de triarylamine et élément électroluminescent organique
US20100140603A1 (en) * 2008-12-08 2010-06-10 Hyuncheol Jeong Blue light emitting compound and organic light emitting diode device comprising the same
WO2010126234A1 (fr) * 2009-04-29 2010-11-04 Dow Advanced Display Materials,Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
KR20120021215A (ko) * 2010-08-31 2012-03-08 롬엔드하스전자재료코리아유한회사 신규한 유기 전자 재료용 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20120042634A (ko) * 2010-08-27 2012-05-03 롬엔드하스전자재료코리아유한회사 신규한 유기 전자재료용 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
JP2013093432A (ja) * 2011-10-26 2013-05-16 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP2013103937A (ja) * 2011-11-14 2013-05-30 Universal Display Corp トリフェニレンシランホスト

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WO2010052932A1 (fr) * 2008-11-07 2010-05-14 保土谷化学工業株式会社 Composé ayant un groupe triphénylsilyle et une structure de triarylamine et élément électroluminescent organique
US20100140603A1 (en) * 2008-12-08 2010-06-10 Hyuncheol Jeong Blue light emitting compound and organic light emitting diode device comprising the same
WO2010126234A1 (fr) * 2009-04-29 2010-11-04 Dow Advanced Display Materials,Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
KR20120042634A (ko) * 2010-08-27 2012-05-03 롬엔드하스전자재료코리아유한회사 신규한 유기 전자재료용 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
KR20120021215A (ko) * 2010-08-31 2012-03-08 롬엔드하스전자재료코리아유한회사 신규한 유기 전자 재료용 화합물 및 이를 포함하는 유기 전계 발광 소자
JP2013093432A (ja) * 2011-10-26 2013-05-16 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP2013103937A (ja) * 2011-11-14 2013-05-30 Universal Display Corp トリフェニレンシランホスト

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