WO2005039246A1 - 有機エレクトロルミネッセンス素子、照明装置、表示装置 - Google Patents
有機エレクトロルミネッセンス素子、照明装置、表示装置 Download PDFInfo
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- WO2005039246A1 WO2005039246A1 PCT/JP2004/014307 JP2004014307W WO2005039246A1 WO 2005039246 A1 WO2005039246 A1 WO 2005039246A1 JP 2004014307 W JP2004014307 W JP 2004014307W WO 2005039246 A1 WO2005039246 A1 WO 2005039246A1
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- 0 Cc(cc1c2c3ccc(C)c2)ccc1[n]3-c1ccc(Cc(cc2)ccc2-[n]2c(ccc(*)c3)c3c3c2ccc(*)c3)cc1 Chemical compound Cc(cc1c2c3ccc(C)c2)ccc1[n]3-c1ccc(Cc(cc2)ccc2-[n]2c(ccc(*)c3)c3c3c2ccc(*)c3)cc1 0.000 description 2
- GTKVDXVZGDUCGU-UHFFFAOYSA-N C(C(Cc(cc1)ccc1-[n]1c2ccncc2c2ccccc12)(Cc(cc1)ccc1-[n]1c(ccnc2)c2c2ccccc12)Cc(cc1)ccc1-[n]1c2ccncc2c2c1cccc2)c(cc1)ccc1-[n]1c(ccnc2)c2c2c1cccc2 Chemical compound C(C(Cc(cc1)ccc1-[n]1c2ccncc2c2ccccc12)(Cc(cc1)ccc1-[n]1c(ccnc2)c2c2ccccc12)Cc(cc1)ccc1-[n]1c2ccncc2c2c1cccc2)c(cc1)ccc1-[n]1c(ccnc2)c2c2c1cccc2 GTKVDXVZGDUCGU-UHFFFAOYSA-N 0.000 description 1
- HRWJDDWCJBIRRD-UHFFFAOYSA-N C(c(cc1)ccc1-[n]1c(c[n-]cc2)c2c2ccccc12)c1cc(Cc(cc2)ccc2-[n]2c(cncc3)c3c3ccccc23)cc(Cc(cc2)ccc2-[n]2c(cncc3)c3c3ccccc23)c1 Chemical compound C(c(cc1)ccc1-[n]1c(c[n-]cc2)c2c2ccccc12)c1cc(Cc(cc2)ccc2-[n]2c(cncc3)c3c3ccccc23)cc(Cc(cc2)ccc2-[n]2c(cncc3)c3c3ccccc23)c1 HRWJDDWCJBIRRD-UHFFFAOYSA-N 0.000 description 1
- DKAVREYTWPWOBG-UHFFFAOYSA-N C(c(cc1)ccc1-[n]1c2ccncc2c2c1ccnc2)c1cc(Cc(cc2)ccc2-[n]2c3ccncc3c3c2ccnc3)cc(Cc(cc2)ccc2-[n]2c(ccnc3)c3c3c2ccnc3)c1 Chemical compound C(c(cc1)ccc1-[n]1c2ccncc2c2c1ccnc2)c1cc(Cc(cc2)ccc2-[n]2c3ccncc3c3c2ccnc3)cc(Cc(cc2)ccc2-[n]2c(ccnc3)c3c3c2ccnc3)c1 DKAVREYTWPWOBG-UHFFFAOYSA-N 0.000 description 1
- LIVJJCYSXNRJPL-UHFFFAOYSA-N C(c(cc1)ccc1-c1ccc(Cc(cc2)ccc2-[n]2c3ccncc3c3c2ccnc3)cc1)c(cc1)ccc1-[n]1c2ccncc2c2c1ccnc2 Chemical compound C(c(cc1)ccc1-c1ccc(Cc(cc2)ccc2-[n]2c3ccncc3c3c2ccnc3)cc1)c(cc1)ccc1-[n]1c2ccncc2c2c1ccnc2 LIVJJCYSXNRJPL-UHFFFAOYSA-N 0.000 description 1
- FIRNXGIHIBWXDV-UHFFFAOYSA-N CC(C)(c1ccc(C(C)(C)c(cc2)ccc2-[n](c2ccccc22)c3c2nccc3)cc1)c(cc1)ccc1-[n]1c2cccnc2c2c1cccc2 Chemical compound CC(C)(c1ccc(C(C)(C)c(cc2)ccc2-[n](c2ccccc22)c3c2nccc3)cc1)c(cc1)ccc1-[n]1c2cccnc2c2c1cccc2 FIRNXGIHIBWXDV-UHFFFAOYSA-N 0.000 description 1
- AROAPJGJWPODEW-UHFFFAOYSA-N CC(c1ccc(C(C)c(cc2)ccc2-[n]2c3ccccc3c3c2cccc3)cc1)c(cc1)ccc1N(C1C=CC=CC11C)C2=C1C=CCC2C Chemical compound CC(c1ccc(C(C)c(cc2)ccc2-[n]2c3ccccc3c3c2cccc3)cc1)c(cc1)ccc1N(C1C=CC=CC11C)C2=C1C=CCC2C AROAPJGJWPODEW-UHFFFAOYSA-N 0.000 description 1
- SMNZXXIKLBUPOO-PNOGMODKSA-N CCCc(c1ccccc11)c(/C=C\N)[n]1-c1ccc(Cc2cc(Cc(cc3)ccc3-[n]3c4ccncc4c4ccccc34)cc(Cc(cc3)ccc3-[n]3c4ccncc4c4c3cccc4)c2)cc1 Chemical compound CCCc(c1ccccc11)c(/C=C\N)[n]1-c1ccc(Cc2cc(Cc(cc3)ccc3-[n]3c4ccncc4c4ccccc34)cc(Cc(cc3)ccc3-[n]3c4ccncc4c4c3cccc4)c2)cc1 SMNZXXIKLBUPOO-PNOGMODKSA-N 0.000 description 1
- FEUHGSJKXHIQBD-UHFFFAOYSA-N COc(cc1)cc(c2cc(OC)ccc22)c1[n]2-c1ccc(Cc(cc2)ccc2-[n](c(ccc(OC)c2)c2c2c3)c2ccc3OC)cc1 Chemical compound COc(cc1)cc(c2cc(OC)ccc22)c1[n]2-c1ccc(Cc(cc2)ccc2-[n](c(ccc(OC)c2)c2c2c3)c2ccc3OC)cc1 FEUHGSJKXHIQBD-UHFFFAOYSA-N 0.000 description 1
- ZRDMBJMPCPKEEI-UHFFFAOYSA-N Cc1c(CCc(cc2)c(C)cc2-[n]2c3ccccc3c3c2cccc3)ccc(-[n]2c3ccccc3c3c2cccc3)c1 Chemical compound Cc1c(CCc(cc2)c(C)cc2-[n]2c3ccccc3c3c2cccc3)ccc(-[n]2c3ccccc3c3c2cccc3)c1 ZRDMBJMPCPKEEI-UHFFFAOYSA-N 0.000 description 1
- PVWMVEPEGSXPOO-UHFFFAOYSA-N Fc(cc1)cc(c2cc(F)ccc22)c1[n]2-c1ccc(CCc(cc2)ccc2-[n](c(ccc(F)c2)c2c2c3)c2ccc3F)cc1 Chemical compound Fc(cc1)cc(c2cc(F)ccc22)c1[n]2-c1ccc(CCc(cc2)ccc2-[n](c(ccc(F)c2)c2c2c3)c2ccc3F)cc1 PVWMVEPEGSXPOO-UHFFFAOYSA-N 0.000 description 1
- SLUFGXAKYARYFJ-UHFFFAOYSA-N c(cc1)ccc1-c(cc(cc1)-[n](c2ccccc22)c3c2nccc3)c1-c(c(-c1ccccc1)c1)ccc1-[n](c1ccccc11)c2c1nccc2 Chemical compound c(cc1)ccc1-c(cc(cc1)-[n](c2ccccc22)c3c2nccc3)c1-c(c(-c1ccccc1)c1)ccc1-[n](c1ccccc11)c2c1nccc2 SLUFGXAKYARYFJ-UHFFFAOYSA-N 0.000 description 1
- NSBVOLBUJPCPFH-UHFFFAOYSA-N c1ccc2[nH]c3cccnc3c2c1 Chemical compound c1ccc2[nH]c3cccnc3c2c1 NSBVOLBUJPCPFH-UHFFFAOYSA-N 0.000 description 1
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- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Definitions
- the present invention relates to an organic electroluminescence device and a lighting device, a display device, and a compound that is a material of the organic electroluminescence device using the same.
- ELD electroluminescence display
- the constituent elements of the ELD include an inorganic electroluminescent element and an organic electroluminescent element (hereinafter, also abbreviated as an organic EL element).
- Inorganic electroluminescent devices have been used as flat light sources, but high voltage AC is required to drive the light emitting devices.
- an organic electroluminescence element has a configuration in which a light-emitting layer containing a compound that emits light is sandwiched between a cathode and an anode, and electrons and holes are injected into the light-emitting layer and recombined to form an exciton (
- This is an element that emits light by utilizing the emission of light (fluorescence and phosphorescence) when this exciton is deactivated, and can emit light at a voltage of several volts to several tens of volts.
- it since it is a self-luminous type, it has a wide viewing angle and high visibility, and because it is a thin-film type solid-state element, it is attracting attention from the viewpoint of space saving and portability.
- organic EL devices that emit light with high efficiency and low power consumption are desired.
- stilbene derivatives, Technology to improve emission luminance and extend device life by doping a small amount of phosphor into a tyryl arylene derivative or tris styryl arylene derivative for example, see Patent Document 1
- 8-hydroxyquinoline aluminum complex Having an organic light-emitting layer doped with a small amount of a fluorescent substance as a host compound see, for example, Patent Document 2
- an 8-hydroxyquinoline aluminum complex as a host compound for example, refer to Patent Document 3
- an element having an organic light-emitting layer doped with for example, refer to Patent Document 3).
- Non-Patent Document 1 Since Princeton University reported an organic EL device using phosphorescence from excited triplets (for example, see Non-Patent Document 1), research on materials that exhibit phosphorescence at room temperature has been active. (For example, see Non-Patent Document 2 and Patent Document 4.)
- the upper limit of the internal quantum efficiency is 100%, so the luminous efficiency is quadrupled in principle compared to the case of the excited singlet, and performance almost equivalent to that of a cold cathode tube can be obtained. It can also be used for lighting and is attracting attention.
- an organic EL device using a phosphorescent compound has achieved an internal quantum efficiency of approximately 100% in green and a lifetime of 20,000 hours in green (see Non-Patent Document 3).
- Power There is still room for improvement in light emission brightness.
- a blue to blue-green phosphorescent compound is used as a dopant, a carpazole derivative such as CBP is used as a host compound in some cases. (See Non-Patent Document 4), leaving room for improvement.
- Patent Document 3 Japanese Patent Application Laid-Open No. 63-2664692
- Patent Document 8' Japanese Patent Application Laid-Open No. 2001-284056 '[Patent Document 8']
- JP-A-8-143862 [Patent Document 14] JP 9-249876 A
- Patent Document 17 Japanese Patent Application Laid-Open No. 8-60144
- An object of the present invention is to provide an organic electroluminescent element which exhibits high luminous luminance and luminous efficiency, has a long life, and has excellent heat resistance under high-temperature storage conditions, and a lighting device using the same. It is to provide a display device.
- an organic electroluminescent device having a light emitting layer and a hole blocking layer adjacent to the light emitting layer, wherein the light emitting layer, the hole blocking layer and the hole blocking layer each contain a specific compound.
- FIG. 1 is a schematic diagram showing an example of a display device including an organic EL element.
- FIG. 2 is a schematic diagram of a display unit.
- FIG. 3 is a schematic diagram of a pixel.
- FIG. 4 is a schematic diagram of a passive matrix type full color display device.
- FIGS. 5 (a) and 5 (b) are schematic diagrams of an organic EL device having a sealing structure.
- FIG. 6 is a schematic diagram of a lighting device.
- FIG. 7 is a cross-sectional view of the lighting device.
- FIG. 8 is a spectrum chart of the compound of the present invention. BEST MODE FOR CARRYING OUT THE INVENTION
- the light emitting layer has a partial structure represented by the following general formula (1), and contains at least one compound having a molecular weight of 1700 or less, and the hole blocking layer is composed of a styryl derivative and a boron derivative.
- An organic compound comprising at least one derivative selected from the group consisting of a carboline derivative and a derivative in which at least one carbon atom forming the carboline skeleton of the carboline derivative is substituted with a nitrogen atom.
- Electroluminescent element Electroluminescent element.
- Ar represents an arylene group or a heteroarylene group
- R 2 to R 9 represent a hydrogen atom or a substituent.
- each of the substituents represented by R 2 to R 9 may combine to form a ring.
- the light emitting layer has a partial structure represented by the following general formula (1a), contains at least one compound having a molecular weight of 1700 or less, and the hole blocking layer is made of a styryl derivative, boron A derivative comprising at least one derivative selected from the group consisting of a derivative, a carboline derivative, and a derivative in which at least one carbon atom forming the carboline skeleton of the carboline derivative is substituted with a nitrogen atom.
- Organic electroluminescent device is a partial structure represented by the following general formula (1a), contains at least one compound having a molecular weight of 1700 or less, and the hole blocking layer is made of a styryl derivative, boron A derivative comprising at least one derivative selected from the group consisting of a derivative, a carboline derivative, and a derivative in which at least one carbon atom forming the carboline skeleton of the carboline derivative is substituted with a nitrogen atom.
- Organic electroluminescent device is a
- Ar represents an arylene group or a heteroarylene group
- R 2 to R 9 represent a hydrogen atom or a substituent.
- each of the substituents represented by R 2 to R 9 may combine to form a ring.
- Z represents an atomic group forming a 3- to 8-membered saturated hydrocarbon ring.
- hole blocking layer contains at least one selected from the group consisting of compounds represented by the following general formulas (2) to (10).
- R 2 independently represents an alkyl group, an alkoxyl group, a cyano group or an aryl group
- R 3 and R 4 each independently represent a heterocyclic group or an aryl group.
- R 3 or R 2 and R 4 may combine with each other to form a ring structure.
- ⁇ ⁇ 1 represents an arylene group.
- a ri to Ar 3 represent an aryl group or an aromatic heterocyclic group.
- R 2 independently represents a hydrogen atom or a substituent.
- Ri and R 2 each independently represent a hydrogen atom or a substituent.
- R 2 independently represents a hydrogen atom or a substituent.
- n and m each represent an integer of 1 to k, and k and 1 each represent an integer of 3 to 4.
- each of Rh R 2 independently represents a hydrogen atom or a substituent.
- R 2 independently represents a hydrogen atom or a substituent.
- Z 2 , Z 3 and Z 4 each represent a 6-membered aromatic heterocyclic ring containing at least one nitrogen atom.
- Ar 1 Ar 2 each represents an arylene group or a divalent aromatic heterocyclic group.
- Z 2 represents at least one containing 6-membered aromatic heterocycle each nitrogen atom, L is a divalent linking group.
- o and p each represent an integer of 1 to 3
- Ar ⁇ Ar 2 each represents an arylene group or a divalent aromatic heterocyclic group.
- Z 1 Z 2 , Z 3 , and Z 4 each represent a 6-membered aromatic heterocycle containing at least one nitrogen atom, and L represents a divalent linking group.
- the light emitting layer has a partial structure represented by the general formula (1) and contains at least one compound having a molecular weight of 500 or more and 1700 or less.
- An organic electrotron luminescence device characterized by the following.
- the light emitting layer has at least one compound having a partial structure represented by the general formula (1a) and having a molecular weight of 500 or more and 1700 or less.
- Organic material characterized by containing Electro luminescence device.
- a lighting device comprising the organic electroluminescent element according to any one of the above items 1 to 18.
- a display device comprising: the illumination device according to the item (20); and a liquid crystal element as a display unit.
- a compound having a partial structure represented and having a molecular weight of not more than 170,000 is contained in the light emitting layer, and a styryl derivative, a boron derivative, a carboline derivative, and a compound are provided in the hole blocking layer adjacent to the light emitting layer.
- An organic electroluminescent device containing at least one derivative selected from the group consisting of derivatives in which at least one carbon atom forming the carboline skeleton of the carboline derivative is substituted with a nitrogen atom has a high luminescence. It has been found that the luminous efficiency is high and the life can be prolonged.
- an organic electroluminescent device having a partial structure represented by the general formula (1) or the general formula (la) and having a light-emitting layer containing a compound having a molecular weight of 500 or more and 170 or less. It was found that the deterioration of luminance characteristics during storage at high temperature was significantly improved.
- 1 ⁇ represents a hydrogen atom, an alkyl group, or a cycloalkyl group. From the viewpoint of improving the emission luminance and obtaining high luminous efficiency of the organic electroluminescence device (hereinafter, referred to as organic EL device) of the present invention, a hydrogen atom is most preferable.
- examples of the alkyl group represented by include a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group, a dodecyl group and a tridecyl group.
- the alkyl group may be substituted with an aryl group (for example, a phenyl group, a tolyl group, a xylyl group, a biphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, etc.), and is bonded to an adjacent carbon atom. It may form a ring with a group.
- examples of the cycloalkyl group represented by include a cyclopentyl group and a cyclohexyl group.
- the cycloalkyl group may be substituted with an aryl group in the same manner as the alkyl group described above, or may form a ring with a group bonded to a carbon atom in contact with the cycloalkyl group.
- examples of the arylene group represented by Ar include a phenylene group (for example, an o-phenylene group, an m_phenylene group, a p-phenylene group, etc.) , Naphthalenediyl group, anthracenediyl group, naphthasendyl group, pyrenzyl group, anthracenediyl group, phenanthylene diinole group, naphthinolenaphthalenedinole group, biphenylenyl group (eg, [1,1, -biphenyl] —4, 4 'monodiyl group, 3,3, -biphenyldiyl group, 3,6-biphenyldiyl group, etc.), terphenyl group, quaterphenyldiyl group, kinkphenyldiyl group, sexiphenyldiyl group, septi Examples thereof include a phenylene group (for example,
- examples of the heteroarylene group represented by Ar include a carbazole ring, a triazole ring, a pyrrole ring, a pyridine ring, a pyrazine ring, a quinoxaline ring, a thiophene ring, an oxaziazo mononore ring, and a dibenzofuran ring. And a divalent group derived from a group consisting of a dibenzothiophene ring and an indole ring.
- the heteroarylene group further has substituents represented by R 2 to R 9 described below. You can do it.
- R 2 to R 9 each independently represent a hydrogen atom or a substituent, and may be the same or different. Also, R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , R 8 and R s may be bonded to each other to form an aromatic ring.
- the substituent represented by R 2 to R 9 is an alkyl group (for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a hexyl group).
- octyl group dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc.
- cycloalkyl group eg, cyclopentyl group, cyclohexyl group, etc.
- alkenyl group eg, vinyl group, aryl group, etc.
- alkynyl Groups for example, ethenyl group, propargyl group, etc.
- aryl groups for example, phenyl group, naphthyl group, etc.
- aromatic heterocyclic groups for example, furyl group, chenyl group, pyridyl group, pyridazinyl group, pyrimidinyl group , Birazinyl, triazinyl, imidazolyl, pyrazolyl, thiazolyl, quinazolinyl, phthala
- a heterocyclic group eg, 'pyrrolidyl group
- the arylene group or the heteroarylene group defined by Ar has the same meaning as the arylene group and the heteroarylene group defined by Ar in the general formula (1).
- a 3- to 8-membered saturated hydrocarbon ring formed by Z examples thereof include a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, and a cyclooctane ring.
- the saturated hydrocarbon ring may be unsubstituted or may have a substituent. Examples of the substituent include the substituents represented by R 2 to R 9 in the general formula (1).
- a compound represented by the following general formula (11) is preferable.
- 1 ⁇ to 1 ⁇ have the same meanings as 1 ⁇ to 19 in the general formula (1).
- n represents an integer of 1 to 6.
- J represents an aryl group (eg, phenyl, tolyl, xylyl, biphenyl, naphthyl, anthryl, phenanthryl, etc.), preferably substituted or unsubstituted (N-carbazolyl) represents a phenyl group.
- J represents an n-valent linking group, and has a direct bond, an oxygen atom, a sulfur atom, an aliphatic hydrocarbon group which may have a substituent, and a substituent. Selected from an aliphatic heterocyclic group which may be substituted, an aromatic hydrocarbon group which may have a substituent, an optionally substituted aromatic group and an aromatic heterocyclic ring.
- FIG. 8 shows the absorption, fluorescence and excitation spectrum of compound H-1 measured in tetrahydrofuran.
- the molecular weight of the compounds according to the invention is a force S which is 1700 or less, preferably 500-700. Thereby, it is possible to exhibit a long life, a high luminous luminance and a high luminous efficiency, and to suppress the deterioration of the luminance characteristics during storage at a high temperature.
- anode in the organic EL device a material having a large work function (4 eV or more), a metal, a metal, an electrically conductive compound, and a mixture thereof is preferably used.
- Metals such as A u Specific examples of such an electrode material, Cu I, Injiumuchi Nokishido (I TO), Sn0 2, include a conductive transparent material such as Zeta Itashita is. It may also be used IDI XO (I n 2 0 3 -ZnO) spruce amorphous in can prepare a transparent conductive film material.
- the anode may be formed into a thin film by a method such as evaporation or sputtering of these electrode substances, and a pattern having a desired shape may be formed by a photolithography method. m or more), and a pattern may be formed through a mask having a desired shape during the deposition or sputtering of the electrode material.
- a pattern having a desired shape may be formed by a photolithography method. m or more
- a pattern may be formed through a mask having a desired shape during the deposition or sputtering of the electrode material.
- the sheet resistance of the anode is preferably several hundred ⁇ / port or less.
- the film thickness is selected in the range of usually 1 O nm to 100 nm, preferably 10 nm to 200 nm, depending on the material.
- a metal having a low work function (4 eV or less) electron injectable metal
- an alloy an electrically conductive compound, and a mixture thereof
- an electrode material include sodium, sodium dium alloy, magnesium, lithium, magnesium z copper mixture, magnesium z silver mixture, magnesium Z aluminum mixture, magnesium nodium indium mixture, aluminum Z aluminum oxide (AI 2 O 3 ) Mixtures, indium, lithium Z-aluminum mixtures, rare earth metals and the like.
- a mixture of an electron-injecting metal and a second metal which is a metal having a large work function and a stable work function, such as magnesium magnesium silver, in terms of electron-injecting properties and durability against oxidation.
- a mixture of magnesium magnesium silver such as magnesium magnesium silver, in terms of electron-injecting properties and durability against oxidation.
- magnesium ⁇ Takeno aluminum mixture, magnesium Roh indium mixture, aluminum Z acid aluminum (a 1 2 0 3) mixture, lithium / aluminum mixture, Aruminiu beam and the like.
- the cathode can be manufactured by forming a thin film from these electrode substances by a method such as evaporation or sputtering.
- the sheet resistance as the cathode is preferably several hundreds ⁇ or less, and the film thickness is usually selected in the range of 10 nm to 100 nm, preferably in the range of 50 nm to 200 nm.
- the film thickness is usually selected in the range of 10 nm to 100 nm, preferably in the range of 50 nm to 200 nm.
- ⁇ Injection layer electron injection layer, hole injection layer ⁇
- the injection layer is provided as necessary, and has an electron injection layer and a hole injection layer. As described above, between the anode and the light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer. May exist.
- the injection layer is a layer provided between the electrode and the organic layer to reduce the driving voltage and to improve the light emission luminance.
- the anode buffer layer (hole injection layer) is also disclosed in JP-A-9-45479, JP-A-126600, JP-A-8-88069, and the like. Details are described. Specific examples include one layer of phthalocyanine buffer represented by phthalocyanine, an oxide buffer layer represented by vanadium oxide, one layer of amorphous carbon buffer, and conductive materials such as polyaniline (emeraldine) and polythiophene. And a polymer buffer layer using a conductive polymer. Above all, it is preferable to use polydioxythiophenes, whereby an organic EL device exhibiting higher luminous luminance and luminous efficiency and having a longer life can be obtained.
- one anode buffer layer is provided between the anode and the light emitting layer and is provided so as to be adjacent to the light emitting layer.
- One layer of the cathode buffer (electron injection layer) is described in detail in JP-A-6-325871, JP-A-117-15744, and JP-A-10-74586.
- a metal buffer represented by strontium aluminum an alkali metal compound buffer layer represented by lithium fluoride, and a layer represented by magnesium fluoride
- the buffer layer injection layer
- the thickness of the film is 0.1 ⁇ !
- the preferred range is ⁇ 100 nm.
- the blocking layer is provided as necessary in addition to the basic constituent layers of the organic compound thin film.
- Japanese Patent Application Laid-Open Nos. H11-2004-258, H11-2004-359, and "Organic EL Devices and Their Forefront of Industrialization (Jan. A hole blocking layer (hole block) is described on page 237 of “0th NTS Company”).
- the L-blocking layer is an electron transport layer in a broad sense, and is made of a material that has a function of transporting electrons and has a very small ability to transport holes. And the recombination probability of holes can be improved.
- the hole blocking layer has a role of preventing holes moving from the hole transport layer from reaching the cathode, and a compound capable of efficiently transporting electrons injected from the cathode toward the light emitting layer. It is formed.
- the physical properties required of the material constituting the hole blocking layer are that the electron mobility is high and the hole mobility is low, and the ionization potential of the light-emitting layer It is preferable to have a band gap larger than the band gap of the light emitting layer having a large value of the ionization potential.
- the hole blocking layer is selected from the group consisting of a styryl derivative, a boron derivative, a carboline derivative, and a derivative group in which at least one carbon atom forming the carboline skeleton of the carboline derivative is substituted with a nitrogen atom.
- the emission luminance and the emission efficiency can be further improved.
- the hole blocking layer contains at least one of the compounds represented by the general formulas (2) to (10). And luminous efficiency can be improved.
- examples of the alkyl group represented by R 2 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group, and a dodecyl group.
- examples of the alkoxyl group represented by R 2 include a methoxy group, an ethoxy group, a butoxy group, a propyloxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, and a dodecyloxy group.
- examples of the aryl group represented by R 2 include a phenyl group, a tolyl group, a xylyl group, a biphenyl group, a naphthyl group, an anthryl group, a phenyl group, a phenanthryl group and the like.
- the alkyl group, alkoxyl group and aryl group represented by R 2 further have a substituent represented by R 2 to R 9 in the general formula (1). Oh good.
- examples of the heterocyclic group represented by R 3 and R 4 include a furyl group, a chenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazul group, a triazinyl group, an imidazolyl group, and a pyrazolyl group.
- the aryl group represented by R 3 and R 4 has the same meaning as the aryl group represented by R 2 in the general formula (2).
- examples of the aryl group represented by Ari include a phenyl group, a tolyl group, a xylyl group, a biphenyl group, a naphthyl group, an anthryl group, and a phenanthryl group.
- examples of the aromatic heterocyclic group represented by A ri include a furyl group, a chel group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a virazinyl group, a .triazyl group, Examples include an imidazolyl group, a pyrazolyl group, a thiazolyl group, a quinazolinyl group, and a phthalazinyl group.
- the aryl group and the aromatic heterocyclic group represented by A r are each further substituted with a substituent represented by R 2 to R 9 in the general formula (1). You may have it.
- examples of the 6-membered aromatic heterocycle each containing at least one nitrogen atom represented by Z 2 , Z 3 , and Z 4 include, for example, a pyridine ring, a pyridazine ring, and a pyrimidine ring And a pyrazine ring.
- the 6-membered aromatic heterocyclic ring containing at least one nitrogen atom, each represented by Zi, Z 2 , Z 3 , and Z 4 is further represented by R 2 to R 9 in the general formula (1). It may have a substituent represented.
- examples of the 6-membered aromatic heterocycle each containing at least one nitrogen atom represented by Z 2 include a pyridine ring, a pyridazine ring, a pyrimidine ring, and a pyrazine ring. And the like.
- examples of the arylene group represented by A r A r 2 include an o_phenylene group, an m-phenylene group, a p-phenylene group, a naphthalenediinole group, and an anthracene group.
- the arylene group may further have a substituent represented by R 2 to R 9 in the general formula (1).
- a divalent aromatic heterocyclic group represented by A ri and Ar 2 are furan, thiophene, pyridine, pyridazine, pyrimidine, pyrazine, triazine, benzimidazole, oxaziazole, triazole, imidazole, pyrazole, thiazole, indole, benzimidazole, Benzothiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, phthalazine ring, carbazole ring, carbazole ring, ring, ring in which the carbon atom of the hydrocarbon ring constituting the carboline ring is further substituted with a nitrogen atom, etc. And divalent groups derived therefrom. Further, the aromatic heterocyclic group may have a substituent represented by R 2 one R 9 in the general formula (1).
- the divalent linking group represented by L has the same meaning as the divalent linking group represented by the formula in the general formula (10), but is preferably an alkylene group.
- examples of the 6-membered aromatic heterocyclic ring represented by Z 2 , Z 3 , and Z 4 each containing at least one nitrogen atom include a pyridine ring, a pyridazine ring, Examples include a pyrimidine ring and a pyrazine ring.
- the divalent linking group represented by L has the same meaning as the divalent linking group represented by the formula in the general formula (10). It is a divalent group containing a chalcogen atom such as a kylene group, 1 O— or 1 S—, and most preferably an alkylene group.
- Exemplified Compound 144 was confirmed by using —NMR spectrum and mass spectrometry spectra.
- the spectrum data of the exemplary compound 144 are as follows.
- Exemplified Compound 143 was confirmed by using —NMR spectrum and mass spectrometry spectrum.
- the spectrum data of the exemplified compound 143 are shown below.
- Exemplified Compound 143 In the synthesis of Exemplified Compound 143, one of the pyridine rings of 4,4, -dichloro-1,3,1-bipyridinole was changed to benzene. Exemplified compound 145 was synthesized in the same manner except that was used.
- Exemplified Compound 145 was confirmed by using an iH-NMR spectrum and a mass spectrometry spectrum.
- the spectrum data of the exemplified compound 145 are shown below.
- At least one carbon atom is nitrogen
- Derivatives substituted with atoms and their chloroplasts are described in J. Chem. Soc, Perkin Trans. 1, 1505--1510 (1999), Pol. J. Chem. , 54, 1585 (1980) and (Tetrahedron Lett. 41 (2000), 481-484).
- the introduction of cores and linking groups, such as aromatic rings, heterocycles, and alkyl groups, into synthesized azacarbazole rings and their chloroplasts involves Ullman coupling, coupling using a Pd catalyst, and Suzuki coupling. For example, a known method can be used.
- Examples of other compounds include the exemplified compounds described in JP-A-2003-313667 and JP-A-2003-313668.
- an electron blocking layer is a hole transport layer in a broad sense, and has a very small ability to transport electrons while having the function of transporting holes. Blocking can improve the probability of recombination of electrons and holes.
- the light emitting layer according to the present invention contains a light emitting material, and is a layer that emits light by recombination of electrons and holes injected from an electrode or an electron transporting layer and a hole transporting layer. It may be inside the light emitting layer or at the interface between the light emitting layer and the adjacent layer.
- the light emitting layer contains a light emitting material and a compound (host compound) having a partial structure represented by the above general formula (1) and having a molecular weight of 1700 or less.
- a phosphorescent compound is a compound that emits light from an excited triplet, is a compound that emits phosphorescence at room temperature (25 ° C), and has a phosphorescence quantum yield of 0 at 25 ° C. .01 One or more compounds. Re The optical quantum yield is preferably 0.1 or more.
- the phosphorescence quantum yield can be measured by the method described in Spectroscopy II, 4th edition, Spectroscopy II, pp. 398 (1992 edition, Maruzen).
- the phosphorescence quantum yield in a solution can be measured using various solvents, but the phosphorescent compound used in the present invention only needs to achieve the above-described phosphorescence quantum yield in any of the solvents.
- the phosphorescent compound can be appropriately selected from known compounds used for the light emitting layer of the organic EL device.
- the phosphorescent compound is preferably an osmium, iridium, rhodium or platinum complex-based compound, whereby the emission luminance and the emission efficiency can be further improved.
- the maximum phosphorescent emission wavelength of the phosphorescent compound is not particularly limited, and in principle, the central metal, the ligand, the substituent of the ligand, and the like can be selected.
- the ability to change the emission wavelength obtained The phosphorescent light-generating compound preferably has a maximum phosphorescence emission wavelength of 380 to 480 nm. With such an organic EL device emitting blue phosphorescent light or an organic EL device emitting white phosphorescent light, an organic electroluminescent device having higher emission luminance and longer half-life can be obtained.
- White light can be emitted by adjusting the type and amount of phosphorescent compound, and it can be applied to lighting devices and backlights. it can.
- the light emitting layer may further contain a host compound having a maximum fluorescence wavelength as the host compound.
- a host compound having a maximum fluorescence wavelength is one having a high fluorescence quantum yield in a solution state.
- the fluorescence quantum yield is preferably 10% or more, particularly preferably 30% or more.
- the host compound having a maximum fluorescence wavelength examples include coumarin dyes, pyran dyes, cyanine dyes, crocodin dyes, squarium dyes, oxobenzanthracene dyes, fluorescein dyes, and rhodamine. Dyes, pyridium dyes, perylene dyes, stilbene dyes, polythiophene dyes, and the like. The fluorescence quantum yield can be measured by the method described in Spectroscopy II, pp. 3652 (1992 edition, Maruzen) of the 4th edition of Experimental Chemistry Lecture 7.
- the light-emitting layer can be formed by forming the above compound by a known thinning method such as a vacuum evaporation method, a spin coating method, a casting method, an LB method, and an ink jet method. Preferably, a spin coating method is used. .
- the thickness of the light emitting layer is not particularly limited, but is usually selected in the range of 5 nm to 5, preferably 5 nm to 200 nm.
- the light-emitting layer may have a single-layer structure composed of one or more of these phosphorescent compounds and host compounds, or may have a multilayer structure having the same composition or different compositions. It may have a layered structure. ⁇ Hole transport layer ⁇
- the hole transport layer is made of a material having a function of transporting holes.
- a hole injection layer and an electron blocking layer are also included in the hole transport layer.
- the hole transport layer and the electron transport layer can be provided as a single layer or a plurality of layers.
- the hole transporting material is not particularly limited, and is conventionally used in photoconductive materials as a material commonly used as a hole charge injecting and transporting material, and used in a hole injecting layer and a hole transporting layer of an EL element. Any one of known ones can be selected and used.
- the hole transporting material has any of hole injection or transport and electron barrier properties, and may be any of an organic substance and an inorganic substance.
- triazole derivatives oxaziazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazoopene derivatives, phenylenediamine derivatives, lylamine derivatives, amino substituted chalcone derivatives, oxazole derivatives, styryl anthracene derivatives
- Examples include a fluorenone derivative, a hydrazone derivative, a stilbene derivative, a silazane derivative, an aniline-based copolymer, and a conductive polymer oligomer, particularly, a thiophenone oligomer.
- hole transporting material those described above can be used, and it is preferable to use a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound.
- aromatic tertiary amine compounds and styrylamine compounds include N, N, N, N, 1-tetraphenyl 4,4'-diaminophenyl; N, N, diphenyl N, N, and bis ( 3-Methylphenyl) [1,1,1-biphenyl] 1,4,4-diamine (TPD); 2,2-bis (4-di-p-tolylaminophenyl) propane; 1,1 N-bis (4-di-p-tolylaminophenyl) cyclohexane; N, N, ⁇ ', N'-tetra-p-tolyl-1,4,4, diaminobiphenyl; 1,1-bis (4-di- p -tolylaminophenyl) -14-phenylcyclohexane; bis (4-dimethylamino) N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-
- No. 5,061,569 for example , 4,4,1-bis [ ⁇ - (1-naphthyl) -l-phenylamino] biphenyl (NPD), three triphenylamine units described in JP-A-4-308868, star-star type 4,4,4 "tris [N- (3-methylphenyl) -N-phenylamino] trifluoramine (MTDATA) and the like.
- NPD 4,4,1-bis [ ⁇ - (1-naphthyl) -l-phenylamino] biphenyl
- MTDATA trifluoramine
- a polymer material in which these materials are introduced into a polymer chain, or a polymer material in which these materials are used as a polymer main chain can also be used.
- inorganic compounds such as p-type Si and p-type SiC can be used as the hole injection material and the hole transport material.
- the hole transporting material of the hole transporting layer preferably has a fluorescence maximum wavelength of 415 nm or less. That is, the hole transporting material is preferably a compound which has a hole transporting property, prevents a long wavelength emission, and has a high Tg.
- This hole transport layer can be formed by thinning the above-described hole transport material by a known method such as a vacuum evaporation method, a spin coating method, a casting method, an ink jet method, and an LB method. it can.
- the thickness of the hole transport layer is not particularly limited, but is usually about 5 to 500 nm.
- the hole transport layer may have a single-layer structure composed of one or more of the above materials.
- Electron transport layer is made of a material having a function of transporting electrons. In a broad sense, an electron injection layer and a hole blocking layer are also included in the electron transport layer.
- the electron transport layer used in the present invention may be provided as a single layer or a plurality of layers.
- electron transporting material also serving as a hole-blocking material
- electron transport materials include: nitro-substituted fluorene derivatives, diph: diquinone derivatives, thiopyrandioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, and anthraquinodimethanes. And anthrone derivatives and oxaziazo mono derivatives.
- a thiadiazole derivative in which an oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be used as the electron transporting material.
- the electron transporting layer only needs to have a function of transmitting electrons injected from the cathode to the light emitting layer, and any material can be selected from conventionally known compounds. .
- a polymer material in which these materials are introduced into a polymer chain, or a polymer material in which these materials are used as a polymer main chain can also be used.
- metal complexes of 8-quinolinol derivatives such as tris (8-quinolinol) aluminum (A1q), tris (5,7-dichloro-8-quinolinol) aluminum, tris (5,7-jib-mouth) Quinolinol) aluminum, tris (2-methyl-18-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), etc.
- a metal complex in which is replaced by In, Mg, Cu, Ca, Sn, Ga or Pb can also be used as the electron transporting material.
- metal-free or metal phthalocyanine or those whose terminals are substituted with an alkyl group ⁇ sulfonic acid group or the like can be preferably used as the electron transporting material.
- the distyryl virazine derivative exemplified as a material for the light emitting layer can also be used as the electron transporting material.
- n-type Si and n-type An inorganic semiconductor such as SiC can also be used as the electron transport material.
- the compound used in the electron transport layer has a fluorescence maximum wavelength of 415 nm or less. That is, the compound used in the electron transporting layer is preferably a compound having an electron transporting property, preventing a longer wavelength of light emission, and having a high Tg.
- This electron transport layer can be formed by thinning the above-mentioned electron transport material by a known method such as a vacuum evaporation method, a spin coating method, a casting method, an ink jet method, and an LB method.
- the thickness of the electron transport layer is not particularly limited, but is usually about 5 to 500 nm.
- the electron transport layer may have a single-layer structure made of one or more of the above materials.
- Substrate also called substrate, substrate, support, etc.
- the substrate that can be used in the organic EL device of the present invention is not particularly limited in the type of glass, plastic, and the like, and is not particularly limited as long as it is transparent.
- Preferred examples of the substrate include glass, quartz, and a light-transmitting resin film.
- a particularly preferred substrate is a resin film capable of providing flexibility to the organic EL device.
- the resin film examples include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyether imide, polyetherenoate etheroketone, polyphenylene sulfide, polyarylate, polyimide, polyimide, and the like.
- PET polyethylene terephthalate
- PEN polyethylene naphthalate
- PES polyethersulfone
- PC polycarbonate
- TAC cellulose triacetate
- TACFilms composed of cellulose acetate propionate (CAP) and the like.
- an inorganic or organic film or a hybrid film of both of them may be formed on the surface of the resin film.
- the external extraction efficiency of light emission of the organic electroluminescence device of the present invention at room temperature is preferably 1% or more, and more preferably 2% or more.
- the external extraction quantum efficiency (%) the number of photons emitted to the outside of the organic EL element Z The number of electrons flowing to the organic EL element x 100.
- hue improving filter such as a color filter may be used in combination.
- the multicolor display device of the present invention includes at least two types of organic EL devices having different emission maximum wavelengths. A preferred example of manufacturing an organic EL device will be described.
- the vacuum evaporation method or the spin coating method is particularly preferable in that holes are hardly generated. Further, a different film forming method may be applied to each layer.
- the deposition conditions vary depending on the type of compound used, etc., but generally the port heating temperature is 50 to 450 ° C, and the degree of vacuum is 10 to 6 Pa: LO. -. 2 P a, deposition rate 0 0 1 nm ⁇ 5 0 n mZ sec, substrate temperature - 5 0 ° C ⁇ 3 0 0 ° C, be appropriately selected in the range of thickness of 0 I nm ⁇ 5 ⁇ m. desirable.
- a thin film made of a cathode material is formed thereon to a thickness of ⁇ ⁇ or less, preferably in the range of 50 nm to 200 nm, for example, by vapor deposition or sputtering.
- a desired organic EL device can be obtained by forming the cathode by the above method and providing a cathode.
- the hole injection layer to the cathode be produced consistently by a single evacuation, but it is also possible to take it out in the middle and apply a different film forming method. At that time, consideration must be given to performing the work in a dry inert gas atmosphere.
- a shadow mask is provided only when the light-emitting layer is formed, and the other layers can be formed in common, and a layer can be formed on one surface by a vapor deposition method, a casting method, a spin coating method, an inkjet method, a printing method, or the like. .
- each layer can be manufactured by reversing the manufacturing order.
- the display device of the present invention uses the organic EL device of the present invention, and can be used as a display device, a display, and various light-emitting light sources.
- full-color display can be achieved by using three types of organic EL devices that emit blue, red, and green light.
- Examples of the display device and display include a television, a personal computer, a mopile device, an AV device, a teletext display, and information display in a car.
- it may be used as a display device for playing back still images or moving images, or when used as a display device for playing back moving images.
- the drive method may be either a simple matrix (passive matrix) method or an active matrix method. .
- the lighting device of the present invention uses the organic EL element of the present invention, and is used for home lighting, vehicle interior lighting, clock backlight, signboard advertising, traffic lights, light sources for optical storage media, light sources for electrophotographic copying machines, and light sources. Examples include, but are not limited to, light sources for communication processors, light sources for optical sensors, and the like. Further, it can be used as a backlight of a liquid crystal display device or the like. Further, the organic EL device according to the present invention may be used as an organic EL device having a resonator structure.
- the purpose of using the organic EL device having such a resonator structure is as follows: a light source of an optical storage medium, a light source of an electrophotographic copying machine, a light source of an optical communication processor, a light source of an optical sensor, and the like. It is not limited to these. In addition, laser oscillation may be used for the above purpose.
- the organic EL device of the present invention can be used for one type of lamp such as an illumination or exposure light source. It may be used as a projection device, a projection device that projects an image, or a display device (display) that directly views a still image or a moving image.
- the driving method may be either a simple matrix method (passive matrix method) or an active matrix method.
- a full-color display device can be manufactured by using three or more kinds of the organic EL elements of the present invention having different emission colors.
- one color, for example, white light emission can be converted to BGR using a color filter to be full color.
- FIG. 1 is a schematic diagram illustrating an example of a display device including an organic EL element.
- FIG. 2 is a schematic view of a display of a mobile phone or the like, for example, which displays image information by light emission of an organic EL element.
- the display 1 includes a display unit A having a plurality of pixels, a control unit B for scanning the display unit A based on image information, and the like.
- the control unit B is electrically connected to the display unit A, and sends a scanning signal and an image data signal to each of a plurality of pixels based on image information from the outside.
- the image is scanned and the image information is displayed on the display unit A by sequentially emitting light according to the signal.
- the display section A has a wiring section including a plurality of scanning lines 5 and data lines 6 on a substrate, and a plurality of images on a substrate. Element 3 and so on.
- the main members of the display unit A will be described below.
- FIG. 2 shows a case where the light emitted from the pixel 3 is extracted in the white arrow direction (downward).
- the scanning lines 5 and the plurality of data lines 6 in the wiring section are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a grid pattern, and are connected to the pixels 3 at orthogonal positions. (Not shown).
- the pixel 3 When the scan signal is applied from the scanning line 5, the pixel 3 receives the image data signal from the data line 6, and emits light according to the received image data.
- the pixel 3 By arranging pixels in the red color region, pixels in the green color region, and pixels in the blue color region on the same substrate as appropriate, full-color display becomes possible.
- FIG. 3 is a schematic diagram of a pixel.
- the pixel includes an organic EL element 10, a switching transistor 11, a driving transistor 12, a capacitor 13 and the like.
- Full-color display can be performed by using red, green, and blue light-emitting organic EL elements as the organic EL elements 10 for a plurality of pixels and juxtaposing them on the same substrate.
- an image data signal is applied from the control unit B to the drain of the switching transistor 11 via the data line 6.
- the scan signal is applied from the control unit B to the gate of the switching transistor 11 via the scanning line 5
- the driving of the switching transistor 11 is turned on, and the image data signal applied to the drain is output. It is transmitted to the gates of the capacitor 13 and the drive transistor 12.
- the capacitor 13 is charged according to the potential of the image data signal, and the drive of the drive transistor 12 is turned on.
- the driving transistor 12 has a drain connected to the power supply line 7 and a source connected to the electrode of the organic EL element 10. A current is supplied from the power supply line 7 to the organic EL element 10 according to the potential of the image data signal applied to the gate.
- the driving of the switching transistor 11 is turned off. Therefore, even if the driving of the switching transistor 11 is turned off, the capacitor 13 holds the potential of the charged image data signal, so that the driving of the driving transistor 12 is kept on, and the next scanning is performed. ⁇ ⁇ The light emission of the organic EL element 10 continues until the signal is applied.
- the drive transistor 12 is driven according to the potential of the next image data signal synchronized with the scan signal, and the organic EL element 10 emits light.
- the light emission of the organic EL element 10 is provided by providing a switching transistor 11 and a drive transistor 12 which are active elements to the organic EL element 10 of each of the plurality of pixels, and The organic EL element 10 emits light.
- a light emitting method is called an active matrix method.
- the light emission of the organic EL element 10 may be light emission of a plurality of gradations by a multi-valued image data signal having a plurality of gradation potentials, or a predetermined light emission amount may be turned on by a binary image data signal. It may be off.
- the holding of the potential of the capacitor 13 may be continued until the next scanning signal is applied, or may be discharged immediately before the next scanning signal is applied.
- a passive matrix light emission drive in which an organic EL element emits light in response to a data signal only when a scanning signal is scanned may be used.
- FIG. 4 is a schematic diagram of a display device using a passive matrix system.
- a plurality of scanning lines 5 and a plurality of image data lines 6 face each other with a pixel 3 therebetween in a grid pattern. Is provided.
- the pixels 3 connected to the applied scanning line 5 emit light according to the image data signal.
- the pixel 3 has no active element, and the manufacturing cost can be reduced.
- the transparent support substrate provided with this ITO transparent electrode was The substrate was subjected to ultrasonic cleaning with propyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
- This transparent support substrate was fixed to the substrate holder of a commercially available vacuum evaporation system, while a_NPD, CBP, Ir-11, BC, and Alq were placed in five molybdenum resistance heating boats, respectively. Installed.
- the pressure in the vacuum chamber was reduced to 4 ⁇ 10-4 Pa, and then Nichia NPD was deposited on the transparent support substrate so as to have a thickness of 2 O nm, and a hole injection Z transport layer was provided. . Further, the heating port containing CBP and the boat containing Ir-11 were separately energized to adjust the deposition rate of CBP and Ir-1 to 100: 7, and the film thickness 3 A light emitting layer was formed by vapor deposition to a thickness of O nm.
- BC was evaporated to provide a hole blocking layer having a thickness of 10 nm. Further, Alq 3 was deposited thereon to provide an electron transport layer having a thickness of 40 nm.
- a cathode was formed by evaporating aluminum and aluminum iio nm to produce an organic EL device 111.
- the organic EL element 111 was prepared in the same manner as the organic EL element 111 except that the CBP used for the light emitting layer was changed to the compounds shown in Table 1. 1-21-129 were produced.
- Each of the fabricated organic EL elements 1_1 to 1_29 was transferred to a glove box under a nitrogen atmosphere (a glove box replaced with high-purity nitrogen gas with a purity of 99.999% or more) without being exposed to the atmosphere.
- the sealing structure was as shown in (a) and (b).
- Palladium Oxide 25, a water-trapping agent is made of high-purity Parium Oxide powder manufactured by Aldrich Co., Ltd., and sealed with a fluororesin semipermeable membrane (Microtex S-NTF 8031Q manufactured by Nitto Denko) with an adhesive. What was pasted on the can 24 was prepared in advance and used.
- An ultraviolet curing adhesive 27 was used to bond the sealing can and the organic EL device, and an ultraviolet lamp was irradiated to produce a device having a sealing structure in which the two were bonded and sealed.
- 21 is a glass substrate provided with a transparent electrode
- 22 is an organic EL layer comprising the hole injection Z transport layer, light emitting layer, hole blocking layer, electron transport layer, cathode buffer layer, etc.
- 23 is a cathode. .
- the luminance (L) [cd / m 2 ] of the fabricated organic EL device when a current of 2.5 mA / cm 2 was supplied under a dry nitrogen gas atmosphere at a temperature of 23 ° C. was measured.
- CS-1000 manufactured by Minolta
- a spectral radiance meter CS-1000 manufactured by Minolta was also used.
- ⁇ Half life ⁇ Measures the time required for the luminance to drop to half of the luminance immediately after the start of light emission (initial luminance) when driven at a constant current of 2.5 mAZcm2 in a dry nitrogen gas atmosphere at 23 ° C. This was taken as the half life time ( ⁇ ⁇ .5) and used as an index of life.
- a spectroradiometer CS-1000 (Minolta) was used for the measurement.
- the luminance (L) of the fabricated organic EL device when a current of 2.5 mA / cm 2 was supplied at 23 ° C. in a dry nitrogen gas atmosphere was measured, and this was defined as the initial luminance (L0).
- the device was stored in an 85 ° C. constant temperature bath for 500 hours. After that, the device was left to stand at 23 degrees, and the luminance (L500) after 500 hours had elapsed was measured, and the luminance reduction rate was calculated from the following equation.
- Luminance reduction rate (%) [ ⁇ (L 0) one (L 500) ⁇ / (L 0)] X 100
- organic EL device of the present invention is superior in all of the emission luminance, the external extraction quantum efficiency, and the emission lifetime as compared with the comparison.
- the heat resistance test revealed that the luminance characteristics under high-temperature storage were also excellent.
- organic EL elements 1-1B ⁇ : 1-29B, and Ir-1 were replaced in the same manner except that Ir-1 which was a phosphorescent compound was replaced with Ir-12.
- Organic EL devices 1-1R to 112R were fabricated in the same manner except that Ir-19 was replaced. In each of these organic EL devices, the same effect as when Ir-11 was used was obtained. Note that blue light was emitted from the device using Ir-12 and red light was emitted from the device using Ir-19. '
- An organic EL device was manufactured in the same manner as in Example 1, except that CBP used for the light emitting layer and BC used for the hole blocking layer were changed to the compounds shown in Table 2.
- EL devices 2-1 to 2--14 were fabricated.
- the obtained organic EL device 2— ! The emission luminance and the time required to reduce the luminance by half were evaluated in the same manner as in Example 1 for each of Examples 2 to 14 and the results obtained are shown in Table 2.
- Each evaluation result shown in Table 2 was expressed as a relative value when the emission luminance, the quantum efficiency extracted from the outside, and the half-life of the organic EL element 2_1 were 100, respectively.
- organic EL elements 2-1 B to 2-1 2B and Ir-1 were replaced in the same manner except that the phosphorescent compound Ir_1 was replaced with Ir-12.
- Organic EL elements 2-1R to 2_12R were fabricated in the same manner except that the composition was changed to 9. Also in each of the organic EL devices, the courage EL device of the present invention obtained the same effect as that obtained when Ir-11 was used. Note that a device using Ir-12 emitted blue light, and a device using Ir-9 emitted red light.
- the organic EL device 1-13 produced in Example 1 was used.
- the organic EL device 1-13R prepared in Example 1 was used.
- FIG. 1 shows an active matrix type full color display device having the form shown in FIG. 1, and FIG. 2 shows the produced display device. Only a schematic diagram of the display section A is shown. That is, on the same substrate, a wiring portion including a plurality of scanning lines 5 and data lines 6 and a plurality of juxtaposed pixels 3 (pixels in a red region, pixels in a green region, pixels in a blue region, etc.)
- the scanning line 5 and the plurality of data lines 6 of the wiring portion are each made of a conductive material, and the scanning line 5 and the data line 6 are orthogonal to each other in a grid and connected to the pixel 3 at orthogonal positions.
- the plurality of pixels 3 are driven by an active matrix method provided with an organic EL element corresponding to each emission color, a switching transistor as an active element, and a driving transistor.
- an image data signal is received from the data line 6, and light is emitted according to the received image data.
- a color display device was manufactured by appropriately arranging the red, green, and blue pixels in this manner.
- Example 4 (Example of lighting device, using white organic EL element)
- Organic EL device 2-9 prepared in Example 2 except that Ir-11 used for the light emitting layer was changed to a mixture of Ir-1, Ir-19 and Ir-12. 1 1 9 and An organic EL device 2-9 W produced in the same manner was used. The non-light-emitting surface of the organic EL element 2-9 W was covered with a glass case to provide a lighting device.
- the lighting device could be used as a thin lighting device that emits white light with high luminous efficiency and long luminous life.
- FIG. 6 is a schematic diagram of the lighting device
- FIG. 7 is a cross-sectional view of the lighting device.
- the organic EL element 101 is covered with a glass power layer 102 and connected with a power supply line (anode) 103 and a power supply line (cathode) 104.
- 105 is a cathode and 106 is an organic EL layer.
- the glass cover 102 is filled with nitrogen gas 108 and a water catching agent 109 is provided.
- an organic electroluminescent element which exhibits high emission luminance and luminous efficiency and has a long life, a display device and a lighting device using the same, and an organic device in which deterioration of luminance characteristics under high temperature storage is suppressed Elect-opening luminescence element, and a display device and a lighting device using the same can be provided.
Abstract
Description
Claims
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EP04773481A EP1679940A1 (en) | 2003-09-30 | 2004-09-22 | Organic electroluminescent device, illuminating device, and display |
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EP1679940A1 (en) | 2006-07-12 |
US20050069729A1 (en) | 2005-03-31 |
US7795801B2 (en) | 2010-09-14 |
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