WO2008044723A1 - Matériau de dispositif électroluminescent organique, dispositif électroluminescent organique, dispositif d'affichage et d'éclairage - Google Patents

Matériau de dispositif électroluminescent organique, dispositif électroluminescent organique, dispositif d'affichage et d'éclairage Download PDF

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WO2008044723A1
WO2008044723A1 PCT/JP2007/069822 JP2007069822W WO2008044723A1 WO 2008044723 A1 WO2008044723 A1 WO 2008044723A1 JP 2007069822 W JP2007069822 W JP 2007069822W WO 2008044723 A1 WO2008044723 A1 WO 2008044723A1
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group
general formula
organic
atom
represented
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Motoaki Sugino
Masato Nishizeki
Tomohiro Oshiyama
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Konica Minolta Holdings, Inc.
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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Definitions

  • Organic-elect mouth luminescence element material organic-elect-mouth luminescence element, display device and lighting device
  • the present invention relates to an organic electoluminescence device material, an organic electroluminescence device, a display device, and a lighting device.
  • ELD components include inorganic-electric luminescence elements and organic-electric luminescence elements (hereinafter referred to as organic EL elements! /).
  • Inorganic electoric luminescence elements require an alternating high voltage to drive the force light-emitting elements that have been used as planar light sources.
  • An organic EL device has a structure in which a light-emitting layer containing a light-emitting compound is sandwiched between a cathode and an anode, and excitons (excitons) are generated by injecting electrons and holes into the light-emitting layer and recombining them.
  • a stilbene derivative, a distyrylarylene derivative or a tristyrylarylene derivative is doped with a trace amount of a phosphor to improve emission luminance and extend the lifetime of the element.
  • an element having an organic light emitting layer in which an 8-hydroxyquinoline aluminum complex is used as a host compound and a small amount of phosphor is doped to the host compound for example, JP-A 63-264692
  • an 8-hydroxyquinoline aluminum complex is used as a host
  • an element having an organic light emitting layer doped with a quinacridone dye for example, Japanese Patent Publication No. 3-255190
  • the upper limit of the internal quantum efficiency is 100%, so that in principle the luminous efficiency is four times that of the excited singlet, and almost the same performance as a cold cathode tube is obtained. It is also attracting attention as a lighting application.
  • an electron-withdrawing group such as a fluorine atom, a trifluoromethyl group, and a cyano group has been introduced into phenylpyridine as a substituent, and a picolinic acid villaza ball type as a ligand.
  • a picolinic acid villaza ball type as a ligand.
  • ligands see, for example, Patent Documents 6 to 10 and Non-patent documents;! To 4
  • the emission wavelength of the light-emitting material is shortened and blue.
  • high-efficiency devices can be achieved, while the light-emitting lifetime of the devices is greatly deteriorated, so an improvement in the trade-off has been demanded.
  • Patent Documents 1 and 11 examples using a compound having a heterocyclic skeleton of a 6-5-6 type tricyclic condensed ring such as carbazole, dibenzofuran, dibenzothiophene and the like as a ligand are disclosed (for example, Patent Documents 1 and 11). 17 and 18)), however, is insufficient in terms of both the light emission lifetime and the light emission efficiency, and further improvement has been desired.
  • Patent Document 1 JP 2002-332291 A
  • Patent Document 2 Japanese Patent Laid-Open No. 2002-332292
  • Patent Document 3 JP-A-2002-338588
  • Patent Document 4 Japanese Patent Application Laid-Open No. 2002-226495
  • Patent Document 5 JP-A-2002-234894
  • Patent Document 6 International Publication No. 02/15645
  • Patent Document 7 Japanese Patent Laid-Open No. 2003-123982
  • Patent Document 8 JP 2002-117978 A
  • Patent Document 9 Japanese Patent Laid-Open No. 2003-146996
  • Patent Document 10 International Publication No. 04/016711 Pamphlet
  • Patent Document 11 Pamphlet of International Publication No. 04/085450
  • Patent Document 12 Japanese Patent Laid-Open No. 2005-53912
  • Patent Document 13 Japanese Unexamined Patent Publication No. 2003-109758
  • Patent Document 14 Japanese Patent Laid-Open No. 2001-247859
  • Patent Document 15 International Publication No. 05/007767 Pamphlet
  • Patent Document 16 Japanese Patent Laid-Open No. 2005-68110
  • Patent Document 17 Japanese Unexamined Patent Publication No. 2005-23070
  • Patent Document 18 Japanese Patent Laid-Open No. 2005-23071
  • Non-Patent Document 1 Inorganic Chemistry, Vol. 41, No. 12, pp. 3055-3066 (2002)
  • Non-Patent Document 2 Aplied Physics Letters, 79, 2082 (2001)
  • Non-Patent Document 3 Aplied Physics Letters, 83, 3818 (2003)
  • Non-Patent Document 4 New Journal of Chemistry, 26 Volume 1171 (2002) Disclosure of the invention
  • the present invention has been made in view of the above problems, and an object of the present invention is to control an organic EL element using an organic EL element material that has a controlled emission wavelength, exhibits high emission efficiency, and has a long emission lifetime. It is providing an element, an illuminating device, and a display apparatus.
  • A is a cyclic group bonded to the metal atom M through a carbon atom, and B is through a nitrogen atom.
  • the cyclic group represented by A is a group represented by the following general formula (lb), or on the metal complex represented by the general formula (la), A group represented by (lb) is included as a substituent.
  • X represents ⁇ , S, N—R 2 (R 2 represents an alkyl group, an aryl group, or a heteroaryl group).
  • X -L -X is a two-seat arrangement
  • L is
  • X and X represent a group of atoms that form a bidentate ligand.
  • ml represents an integer of 1, 2, or 3
  • M2 represents an integer of 0, 1 or 2 ml + m2 is 2 or 3.
  • M, which is a metal atom, represents a group 8 to group 10 metal in the periodic table.
  • R represents an alkyl group, an aryl group, or a heteroaryl group.
  • Y and Y are nitrogen atoms
  • R is a methyl group or an aryl group.
  • organic electoluminescence device material according to any one of 24, characterized in that
  • R is a ally having a substituent at the 2,6 position.
  • M is Ir or Pt
  • An organic electoluminescence device comprising the organic electroluminescence device material according to item 1 in any one of the above 1 to 8, in a light emitting layer.
  • a display device comprising the organic-electric-luminescence element as described in 9 above.
  • An illuminating device comprising the organic electoluminescence device described in 9 above.
  • an organic EL element material useful for an organic EL element can be obtained.
  • the emission wavelength is controlled, the emission efficiency is high, and the emission lifetime is long.
  • FIG. 1 is a schematic view showing an example of a display device composed of organic EL elements.
  • FIG. 2 is a schematic diagram of display unit A.
  • FIG. 3 is a schematic diagram of a pixel.
  • FIG. 4 is a schematic diagram of a passive matrix type full-color display device.
  • FIG. 5 is a schematic view of a lighting device.
  • FIG. 6 is a schematic diagram of a lighting device.
  • C and N form a covalent bond or a coordinate bond with metal atom M.
  • A is a cyclic group bonded to the metal atom M through a carbon atom.
  • the cyclic group represented by A is preferably a 5-membered or 6-membered ring, and more preferably a ring structure represented by the following general formulas A— ;! to A-53.
  • RA is independently a hydrogen atom or substituent 4
  • Examples of the substituent include 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, an octyl group, a dodecyl group, a tridecyl group, a tetradecyl group).
  • 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, an octyl group, a dodecyl group, a tridecyl group, a tetradecyl group.
  • Aromatic hydrocarbon ring groups also called aromatic carbocyclic groups, aryl groups, etc., for example, phenyl groups, p-phenyl groups, mesityl groups, tolyl groups, xylyl groups, naphthyl groups, anthryl groups, Azulenyl group, acenaphthene binole group, fluorenyl group, phenanthryl group, indur group, pyrenyl group, biphenylurine group, etc.), aromatic heterocyclic group (eg For example, pyridyl group, pyrimidinyl group, furyl group, pyrroly
  • oxazolyl group ⁇ , 1, 2, 4 2,3 ⁇ lyso 'mono- 1- 1-no-re group, etc.
  • oxazolyl group benzoxazolyl group, thiazolyl group, isoxazolyl group, isothia group, furazanyl group, chenyl group, quinolyl group, benzofuryl group, dibenzofuryl group , Benzocenyl group, dibenzocenyl group, indolyl group, canolenozolinole group, carbolinyl group, diazacarbazolyl group (one of the carbon atoms constituting the carboline ring of the carbolinyl group is replaced by a nitrogen atom)
  • Quinoxalinyl group pyridazinyl group, triazinyl group, quinazolinyl group, phthaladyl group, etc.
  • heterocyclic group eg, pyrrolidyl group,
  • a ring may be formed.
  • Rings formed by combining two of RA to RA include naphthalene and tetralyl.
  • Anthracene, phenanthrene, quinoline, isoquinoline, indanol, benzofuran examples include ring structures such as Nzochi-aged phen, indazonore, benzimidazole, benzothiazonole, benzoxazole, carbazonole, dibenzofuran, dibenzothiophene, and benzotriazole.
  • A is also a ring structure represented by the general formula (lb).
  • B is a cyclic group bonded to the metal atom M through a nitrogen atom.
  • the cyclic group represented by B is preferably a 5-membered or 6-membered ring, and more preferably a ring structure represented by the following general formulas B-1-B-27.
  • B represents a cyclic group bonded to the metal atom M through a nitrogen atom.
  • RB, RB, and RB are independently a hydrogen atom or a substituent.
  • Examples of substituents represented by RB, RB, RB, and RB include the above RA, RA, RA, RA, RA
  • Two of RB, RB, RB, and RB may be bonded to each other to form a ring.
  • RB ⁇ An example of a ring formed by combining two of RB is as follows:
  • the A part has a force represented by the general formula (lb), and the substitutable site of the metal complex represented by the general formula (la).
  • the ring structure represented by the general formula (lb) is substituted.
  • X represents ⁇ , S, N 2 -R.
  • R represents an alkyl group, an aryl group, or a heteroaryl group.
  • Examples of the alkyl group, aryl group, and heteroaryl group represented by R include those similar to the alkyl group, aryl group, and heteroaryl group represented by RA, RA, RA, RA.
  • One of Z, Z, Z and Z is a nitrogen atom.
  • Examples of the substituent represented by R are the same as the examples of the substituent represented by RA, RA, RA and RA.
  • X—L—X represents a bidentate ligand
  • X 1 and X 2 each independently represent carbon
  • L represents an atomic group forming a bidentate ligand together with X and X.
  • X — L — 2 represented by X
  • 1 1 2 1 1 2dentate ligands include substituted or unsubstituted phenylpyrrolidine, phenylpyra zonore, phenylimidazonole, phenyltriazolene, phenyltetrazonole, pyrazabole. Acetylacetone, picolinic acid and the like.
  • ml represents an integer of 1, 2 or 3
  • m2 represents a force representing an integer of 0, 1 or 2
  • ml + m2 is 2 or 3. Of these, m2 is preferably 0.
  • the metal represented by M used for forming the metal complex includes
  • transition metal elements of Group 8 to Group 10 also referred to simply as transition metals
  • iridium and platinum are preferable transition metal elements.
  • the metal complex according to the present invention has, for example, a partial structure shown in parentheses having ml, or a portion represented by a tautomer thereof, when ml> m2 as described in the general formula (la).
  • the structure is called a main ligand
  • the partial structure shown in parentheses having m2 or a partial structure represented by a tautomer thereof is called a subligand.
  • the metal complex is composed of a combination of a main ligand or a tautomer thereof and a subligand or a tautomer thereof.
  • m2 0, that is, all the ligands of the metal complex may be composed only of a partial structure represented by the main ligand or a tautomer thereof.
  • a so-called ligand used in the formation of a conventionally known metal complex has a ligand (also known as a coordination compound) known as a ligand, if necessary, as a ligand! / Well! /
  • the type of the ligand in the complex is preferably composed of 1 to 2 types, more preferably 1 type. .
  • the metal complex represented by the general formula (la) is a compound represented by the general formula
  • R represents an alkyl group, an aryl group, or a heteroaryl group.
  • Y, Y is Nikko
  • M is the same as A, X, L, X, ml, m2, M in the general formula (la),
  • the metal complex represented by the general formula (1) is represented by the general formula (1).
  • R is a carbyl group or an aryl group.
  • TM represents the following ⁇ 3 ⁇ 4
  • the organic EL device of the present invention is formed on the light emitting layer or the electron blocking layer in the constituent layers (details will be described later) of the organic EL device. It is preferable to use a material. In the light emitting layer, it is preferably used as a light emitting dopant as described above.
  • the mixing ratio of the light-emitting dopant to the light-emitting host is preferably adjusted to a range of from 0.;! To less than 30% by mass.
  • the luminescent dopant may be a mixture of a plurality of types of compounds.
  • the partner to be mixed may have a different structure, and other metal complexes or phosphorescent dopants or fluorescent dopants having other structures may also be used. Good.
  • Luminescent dopants can be broadly divided into two types: fluorescent dopants that emit fluorescence and phosphorescent dopants that emit phosphorescence.
  • fluorescent dopant include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes , Pyrylium dyes, perylene dyes, steel Examples thereof include rubene dyes, polythiophene dyes, and rare earth complex phosphors.
  • a typical example of the latter is preferably a complex compound containing a transition metal element of Group 8, 9, or 10 in the periodic table of elements, and more preferably an iridium compound.
  • An osmium compound, and most preferred is an iridium compound.
  • JP 2002-100476 JP 2002-173674, JP 2002-359082, JP 2002-175884, JP 2002-363552, JP 2002-184582 Publication, JP 2003-7469, JP 2002-525 808, JP 2003-7471, JP 2002-525833, JP 2003
  • the host compound used in the present invention represents a compound having a phosphorescence quantum yield of phosphorescence emission of less than 0.01 at room temperature (25 ° C.) among compounds contained in the light emitting layer.
  • the luminescent host used in the present invention is not particularly limited in terms of structure, but is typically a force rubazole derivative, triarylamine derivative, aromatic borane derivative, nitrogen-containing bicyclic compound, thiophene derivative.
  • Basic bones such as furan derivatives and oligoarylene compounds
  • Examples thereof include carboline derivatives and derivatives having a ring structure in which at least one of the carbon atoms of the hydrocarbon ring constituting the carboline ring of the carboline derivative is substituted with a nitrogen atom.
  • a force rubazole derivative, a carboline derivative, and a derivative having a ring structure in which at least one of the carbon atoms of the hydrocarbon ring constituting the carboline ring of the carboline derivative is substituted with a nitrogen atom are preferably used.
  • a plurality of known host compounds may be used in combination as a host compound.
  • multiple types of host compounds it is possible to adjust the movement of charges, and the organic EL device can be made highly efficient.
  • these known host compounds compounds that have a hole transporting ability and an electron transporting ability, prevent emission of longer wavelengths, and have a high Tg (glass transition temperature) are preferred! / ,.
  • the light-emitting host used in the present invention may be a low-molecular compound or a high-molecular compound having a repeating unit, which may be a low-molecular compound having a polymerizable group such as a bur group or an epoxy group (evaporation polymerizable light-emitting). Even the host) [0230]
  • a compound having a hole transporting ability and an electron transporting ability, which prevents the light emission from being increased in wavelength, and has a high Tg (glass transition temperature) is preferable.
  • the light emitting layer may further contain a host compound having a fluorescence maximum wavelength as a host compound.
  • a host compound having a fluorescence maximum wavelength is a compound having a high fluorescence quantum yield in a solution state.
  • the fluorescence quantum yield is preferably 10% or more, particularly preferably 30% or more.
  • host compounds having a maximum fluorescence wavelength include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes. And pyrylium dyes, perylene dyes, stilbene dyes, polythiophene dyes, and the like.
  • the fluorescence quantum yield can be measured by the method described in the third edition of Experimental Chemistry Course 7, Spectroscopy II, page 362 (1992 edition, Maruzen).
  • the blocking layer for example, electron blocking layer, hole blocking layer
  • the blocking layer for example, electron blocking layer, hole blocking layer
  • the organic EL device material of the present invention for a hole blocking layer, an electron blocking layer, and the like.
  • the organic EL device material of the present invention is contained in a hole blocking layer and an electron blocking layer
  • the organic EL of the present invention described in any one of claims 1 to 7 The element material may be contained in a state of 100% by mass as a layer constituent component such as a hole blocking layer or an electron blocking layer, or may be mixed with other organic compounds.
  • the thickness of the blocking layer according to the present invention is preferably 3 to 100 nm, and more preferably 5 to 30 nm.
  • the hole blocking layer has a function of an electron transport layer in a broad sense, and is made of a material that has a function of transporting electrons and has an extremely small ability to transport holes, and blocks holes while transporting electrons. By stopping, the recombination probability of electrons and holes can be improved.
  • Examples of the hole blocking layer include, for example, Japanese Patent Application Laid-Open Nos. 11 204258 and 11 204359, and “The Forefront of Organic EL Devices and Their Industrialization (November 30, 1998, NTT Corporation)
  • the hole blocking layer described in page 237 of “Issuance)” is applicable as the hole blocking layer according to the present invention.
  • the structure of the electron carrying layer mentioned later can be used as a hole-blocking layer concerning this invention as needed.
  • the organic EL device of the present invention has a hole blocking layer as a constituent layer, and the hole blocking layer is at least one of the carbon atoms of the hydrocarbon ring constituting the carboline ring of the strong ruporin derivative or the carboline derivative. It is preferable to include a derivative having a ring structure in which one is substituted with a nitrogen atom.
  • the electron blocking layer has a function of a hole transport layer in a broad sense, and is made of a material having a function of transporting holes and an extremely small capacity of transporting electrons. The probability of recombination of electrons and holes can be improved by blocking the children. Moreover, the structure of the positive hole transport layer mentioned later can be used as an electron blocking layer as needed.
  • the organic EL device material of the present invention for the adjacent layer adjacent to the light emitting layer, that is, the hole blocking layer and the electron blocking layer, particularly for the electron blocking layer. It is preferable.
  • the hole transport layer includes a material having a function of transporting holes, and in a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer.
  • a single hole or multiple hole transport layers should be provided.
  • the hole transport material is not particularly limited, and is conventionally used as a hole charge injection / transport material in photoconductive materials, and used in the hole injection layer and hole transport layer of organic EL devices. Any known medium force can be selected and used.
  • the hole transport material has either hole injection or transport or electron barrier properties.
  • organic substances and inorganic substances may be used.
  • triazole derivatives oxazia Azole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, Examples thereof include aniline-based copolymers and conductive polymer oligomers, particularly thiophene oligomers.
  • Typical examples of aromatic tertiary amine compounds and styrylamine compounds include N, N, N ', N' —tetraphenenole 4, A 'diaminophenol; N, N' — diphenenole N, N , —Bis (3 methylphenyl) 1 [1, 1 ′ — biphenyl] 1, 4, 4 ′ — Diamine (TPD); 2, 2-bis (4 di 1 p trilaminophenyl) propane; 1-bis (4 di-l-triarylaminophenenyl) cyclohexane; N, N, N ', N' —tetra-l-trinore 4, A ′ —diaminobiphenyl; 1, 1-bis (4-di-one) p-tolylaminophenyl) 4-phenylcyclohexan; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-di-amino-
  • No. 5,061, 569 in the molecule for example 4 , 4 'bis [N- (1 naphthyl) N phenylamino] biphenyl (NPD), three triphenylamine units described in JP-A-4 308688 are connected in a starburst type, 4, 4', 4 '—Tris [N— (3-methylphenyl) N phenyla Roh] triphenyl ⁇ Min (MTDATA) and the like.
  • these materials are introduced into the polymer chain, or these materials are used as the polymer main chain.
  • High polymer materials can also be used.
  • Inorganic compounds such as p-type Si and p-type SiC can also be used as the hole injecting material and hole transporting material.
  • the hole transport layer is formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, or an LB method. That power S.
  • a vacuum deposition method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, or an LB method. That power S.
  • a vacuum deposition method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, or an LB method. That power S.
  • a vacuum deposition method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, or an LB method. That power S.
  • the electron transport layer is made of a material having a function of transporting electrons, and in a broad sense, an electron injection layer and a hole blocking layer are also included in the electron transport layer.
  • an electron injection layer and a hole blocking layer are also included in the electron transport layer.
  • a single layer or a plurality of layers are provided.
  • the electron transporting layer has a function of transferring electrons injected from the cathode to the light emitting layer, any material selected from conventionally known compounds should be used. Touch with force S.
  • electron transport materials examples include heterocyclic tetrafluoride derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, naphthalene perylene, and the like.
  • derivatives having a cyclic structure examples include heterocyclic tetrafluoride derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, naphthalene perylene, and the like.
  • a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, or a quinoxaline derivative having a quinoxaline ring, known as an electron withdrawing group, can also be used as an electron transport material.
  • these materials are introduced into the polymer chain, or these materials are used as the polymer main chain.
  • High polymer materials can also be used.
  • metal complexes of 8 quinolinol derivatives such as tris (8 quinolinol) aluminum (Alq), tris (5,7-dichloro-1-8-quinolinol) aluminum, tris (5,7-dive mouth 8 quinolinol) Aluminum, tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), etc.
  • the central metals of these metal complexes are In, Mg, Cu, Metal complexes replacing Ca, Sn, Ga or Pb can also be used as electron transport materials.
  • metal-free or metal phthalocyanine or those having terminal ends substituted with an alkyl group or a sulfonic acid group can be preferably used as the electron transport material.
  • the distyrylvirazine derivative exemplified as the material of the light emitting layer can also be used as an electron transport material, and inorganic semiconductors such as n-type Si and n-type SiC can be used as well as the hole injection layer and the hole transport layer. It can be used as an electron transport material.
  • This electron transport layer can be formed by thinning the electron transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, or an LB method. S can. Although there is no restriction
  • This electron transport layer may have a single layer structure composed of one or more of the above materials.
  • the injection layer is provided as necessary, and has an electron injection layer and a hole injection layer, and as described above, exists between the anode and the light emitting layer or hole transport layer and between the cathode and the light emitting layer or electron transport layer. May be.
  • the injection layer is a layer that is provided between the electrode and the organic layer in order to reduce the drive voltage and increase the luminance of the light emission.
  • the organic EL element and the forefront of its industrialization June 30, 1998, NTT) 2) Chapter 2 “Electrode Materials” (pages 123-166) ”of the 2nd volume of“ E.S. Co., Ltd.) ”, the hole injection layer (anode buffer layer), the electron injection layer (cathode buffer layer) There is.
  • Lid Examples include a phthalocyanine buffer layer represented by cyanine, an oxide buffer layer represented by vanadium oxide, an amorphous carbon buffer layer, and a polymer buffer layer using a conductive polymer such as polyaniline (emeraldine) or polythiophene. .
  • cathode buffer layer (electron injection layer) Details of the cathode buffer layer (electron injection layer) are also described in JP-A-6-325871, JP-A-917574, JP-A-10-74586, and the like.
  • Metal buffer layer typified by aluminum, etc., alkali metal compound buffer layer typified by lithium fluoride, alkaline earth metal compound buffer layer typified by magnesium fluoride, oxide buffer typified by aluminum oxide One layer and so on.
  • the buffer layer (injection layer) is preferably a very thin film, although the film thickness is preferably in the range of 0.;! To lOOnm.
  • This injection layer can be formed by thinning the above material by a known method such as a vacuum deposition method, a spin coating method, a casting method, an ink jet method, or an LB method.
  • the thickness of the injection layer is not particularly limited, but is usually about 5 to 5000 nm.
  • This injection layer may have a single layer structure composed of one or more of the above materials.
  • an electrode material made of a metal, an alloy, an electrically conductive compound or a mixture thereof having a high work function (4 eV or more) is preferably used.
  • electrode materials include metals such as Au, and conductive transparent materials such as Cul, indium tin oxide (ITO), SnO, and ZnO.
  • conductive transparent materials such as Cul, indium tin oxide (ITO), SnO, and ZnO.
  • ITO indium tin oxide
  • ZnO ZnO
  • an amorphous material such as IDIXO (In 2 O 3 —ZnO) capable of forming a transparent conductive film may be used.
  • these electrode materials can be formed into a thin film by vapor deposition or sputtering, and a pattern of the desired shape can be formed by photolithography, or when pattern accuracy is not so high (about 100 m or more) ), A pattern may be formed through a mask having a desired shape when the electrode material is deposited or sputtered.
  • the transmittance greater than 10%
  • the sheet resistance as the anode is preferably several hundred ⁇ / mouth or less.
  • the film thickness is usually 10 to 1000 nm, preferably 10 to 200 nm.
  • the cathode a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof is used.
  • an electron injecting metal a material having a low work function (4 eV or less) metal
  • an alloy a material having a low work function (4 eV or less) metal
  • an alloy a material having a low work function (4 eV or less) metal
  • an alloy referred to as an electron injecting metal
  • an alloy an electrically conductive compound
  • a mixture thereof a mixture thereof.
  • Specific examples of such electrode materials include sodium, sodium isotropic lithium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al O) mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like.
  • a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function value than this for example, a magnesium / silver mixture.
  • Magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al 2 O 3) mixtures, lithium / aluminum mixtures, aluminum and the like are suitable.
  • the cathode can be made by forming a thin film of these electrode materials by vapor deposition or sputtering.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / mouth or less.
  • the film thickness is usually 10 to 1000 nm, preferably 50 to 200 nm.
  • it is convenient that either the anode or the cathode of the organic EL element is transparent or translucent to improve the light emission luminance.
  • Substrate also referred to as substrate, substrate, support, etc.
  • the substrate of the organic EL device of the present invention is not particularly limited as long as it is transparent or transparent, and there are no particular restrictions on the type of glass, plastic, etc.
  • Examples of substrates that are preferably used include glass, Examples thereof include quartz and a light-transmitting resin film.
  • a particularly preferred substrate is a resin film that can give flexibility to the organic EL element.
  • Examples of the resin film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheroletherketone, polyphenylenesulfide, polyarylate, polyimide, polycarbonate (PC ), A film made of cellulose triacetate (TAC), cellulose acetate propionate (CAP) or the like.
  • PET polyethylene terephthalate
  • PEN polyethylene naphthalate
  • PES polyethersulfone
  • PES polyetherimide
  • polyetheroletherketone polyphenylenesulfide
  • PC polycarbonate
  • a film made of cellulose triacetate (TAC), cellulose acetate propionate (CAP) or the like On the surface of the resin film, a water vapor transmission rate of 0.01 g / (m 2 '24h'MPa) or less is acceptable even if an inorganic or organic film or a hybrid film of both is formed.
  • the external extraction efficiency at room temperature of light emission of the organic EL device of the present invention is preferably 1% or more, more preferably 2% or more.
  • the external extraction quantum efficiency (%) the number of photons emitted outside the organic EL element / the number of electrons X I 00 flowed to the organic EL element.
  • a hue improving filter such as a color filter may be used in combination.
  • a roughened film such as anti-glare phenol
  • a roughened film may be used in combination in order to reduce unevenness in light emission.
  • anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode buffer layer / cathode force I will explain to you!
  • a thin film made of a desired electrode material for example, an anode material
  • a suitable substrate by a method such as vapor deposition or sputtering so that the film thickness is 1 ⁇ m or less, preferably 10 to 200 nm.
  • an anode is produced.
  • a thin film containing an organic compound such as a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, or an electron transport layer, which is an element material, is formed thereon.
  • a method for reducing the thickness of a thin film containing an organic compound there are a spin coating method, a casting method, an ink jet method, a vapor deposition method, a printing method, and the like.
  • the vacuum deposition method or the spin coating method is particularly preferable because it is difficult to form. Further, a different film forming method may be applied for each layer.
  • the vapor deposition conditions vary depending on the type of compound used, but generally the boat heating temperature is 50 to 450 ° C, the degree of vacuum is 10-6 to 10-2 Pa, and the deposition rate is 0. It is desirable to select as appropriate in the range of 0;! To 50 nm / second, substrate temperature—50 to 300 ° C., and film thickness of 0.1 to 5 m.
  • a thin film made of a cathode material is formed thereon with a thickness of 1 ⁇ m or less, preferably 50
  • a desired organic EL device can be obtained by forming the film so as to have a film thickness in the range of ⁇ 200 nm by, for example, vapor deposition or sputtering, and providing a cathode.
  • the organic EL device is preferably manufactured from the hole injection layer to the cathode consistently by a single vacuum, but it may be taken out halfway and subjected to different film forming methods. At that time, it is necessary to consider that the work is performed in a dry inert gas atmosphere.
  • the display device of the present invention will be described.
  • the display device of the present invention has the organic EL element.
  • the display device of the present invention may be single color or multicolor, but here, the multicolor display device will be described.
  • a shadow mask is provided only at the time of forming a light emitting layer, and a film can be formed on one surface by a vapor deposition method, a casting method, a spin coating method, an ink jet method, a printing method, or the like.
  • the method is not limited, but the vapor deposition method, the ink jet method, and the printing method are preferable. When using vapor deposition, patterning with a shadow mask is preferred.
  • the multicolor display device can be used as a display device, a display, and various light sources.
  • full-color display is possible by using three organic EL elements, blue, red, and green light emission.
  • Examples of the display device and display include a television, a personal computer, a mopile device, an AV device, a character broadcast display, and an information display in a car.
  • a display device for playing back still images and moving images and the drive method when used as a display device for moving image playback is either a simple matrix (passive matrix) method or an active matrix method. It may be.
  • Luminescent light sources include home lighting, interior lighting, clock and liquid crystal backlights, billboard advertisements, traffic lights, optical storage media light sources, electrophotographic copying machine light sources, optical communication processor light sources, optical sensor Examples include light sources, but are not limited to this!
  • the lighting device of the present invention will be described.
  • the lighting device of the present invention has the organic EL element.
  • the organic EL element having the resonator structure may be used as an organic EL element having a resonator structure in the organic EL element of the present invention.
  • Examples include 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. Moreover, you may use for the said use by making a laser oscillation.
  • the organic EL element of the present invention may be used as a kind of lamp for illumination or exposure light source, a projection device for projecting an image, a still image or a moving image directly visible It may be used as a type of display device (display).
  • the driving method may be either a simple matrix (passive matrix) method or an active matrix method.
  • a full-color display device can be manufactured by using two or more organic EL elements of the present invention having different emission colors.
  • FIG. 1 is a schematic view showing an example of a display device composed of organic EL elements.
  • FIG. 2 is a schematic diagram of a display such as a mobile phone that 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 that performs image scanning of 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. Sequentially emits light according to the image data signal, scans the image, and sends the image information to the display unit A.
  • FIG. 2 is a schematic diagram of the display unit A.
  • the display portion A includes a wiring portion including a plurality of scanning lines 5 and data lines 6 and a plurality of pixels on a substrate.
  • the figure shows a case where the light emitted from the pixel 3 is extracted in the direction of the white arrow (downward).
  • the scanning lines 5 and the plurality of data lines 6 in the wiring portion 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 the orthogonal positions (details) Is not shown).
  • the pixel 3 When a scanning signal is applied from the scanning line 5, the pixel 3 receives an image data signal from the data line 6, and emits light in accordance with the received image data.
  • Full color display is possible by arranging pixels in the red region, the green region, and the blue region as appropriate on the same substrate.
  • 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.
  • organic EL elements that emit red, green, and blue as the organic EL elements 10 in multiple pixels, and arranging them on the same substrate in parallel, full-color display can be achieved with power S.
  • an image data signal is applied from the control unit B to the drain of the switching transistor 11 via the data line 6.
  • a scanning 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 transferred to the capacitor 13 and the driving transistor. It is transmitted to the gate of the star 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 drive 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. Current is supplied from the power supply line 7 to the organic EL element 10 in accordance with the potential of the image data signal applied at a time.
  • the organic EL element 10 emits light by providing a switching transistor 11 and a drive transistor 12 as active elements for each of the organic EL elements 10 of each of the plurality of pixels, thereby providing organic EL for each of the plurality of pixels 3.
  • Element 10 is emitting light.
  • Such 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-value image data signal having a plurality of gradation potentials! /
  • the light emission amount may be on or off.
  • the potential of the capacitor 13 can be maintained until the next scanning signal is applied, or can be discharged immediately before the next scanning signal is applied! /.
  • the present invention is not limited to the above-described active matrix system, and may be a passive matrix system light emission drive in which an organic EL element emits light according to a data signal only when a scanning signal is scanned. .
  • FIG. 4 is a schematic diagram of a display device using a passive matrix method.
  • a plurality of scanning lines 5 and a plurality of image data lines 6 are provided in a lattice shape so as to face each other with the pixel 3 interposed therebetween.
  • the pixel 3 connected to the applied scanning line 5 emits light according to the image data signal.
  • the organic EL material of the present invention is an organic EL element that emits substantially white light as a lighting device. Applicable to children. A plurality of light emitting colors are simultaneously emitted by a plurality of light emitting materials, and white light emission is obtained by mixing colors.
  • the combination of multiple emission colors may include three emission maximum wavelengths of the three primary colors of blue, green, and blue, or the complementary colors such as blue and yellow, and blue-green and orange are used 2 It may be one containing two emission maximum wavelengths.
  • a combination of light emitting materials for obtaining a plurality of emission colors includes a combination of a plurality of phosphorescent or fluorescent materials, a fluorescent material or a phosphorescent material, Any combination with a dye material that emits light as excitation light may be used, but in the white organic EL device according to the present invention, only a combination of a plurality of light-emitting dopants may be mixed.
  • a mask is provided only at the time of formation of the light emitting layer, hole transport layer, electron transport layer, etc.
  • an electrode film can be formed on one side by vapor deposition, casting, spin coating, ink jet, printing, etc., and productivity is improved. According to this method, unlike the white organic EL device in which light emitting elements of a plurality of colors are arranged in parallel in an array, the elements themselves emit white light.
  • the light emitting material used for the light emitting layer is not particularly limited.
  • the light emitting material according to the present invention is adapted so as to conform to the wavelength range corresponding to the CF (color filter) characteristics. Select any of the metal complexes and known luminescent materials and combine them to whiten! /.
  • the white light-emitting organic EL device is not only the display device and the display, but also a variety of light-emitting light sources and lighting devices, such as home lighting, interior lighting, and exposure light source. It is also useful for display devices such as backlights for liquid crystal display devices.
  • the transparent support substrate with this ITO transparent electrode was ultrasonically cleaned with isopropyl alcohol Then, it was dried with dry nitrogen gas, and UV ozone cleaning was performed for 5 minutes.
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum evaporation system, while ⁇ -NPD, H4, Ir 12, BCP, and Alq are placed in five tantalum resistance heating boats, respectively. (Vacuum chamber).
  • lithium fluoride was put into a resistance heating boat made of tantalum, and aluminum was put into a resistance heating boat made of tungsten, respectively, and attached to the second vacuum chamber of the vacuum evaporation apparatus.
  • the heating boat containing H4 and the boat containing Ir 12 are energized independently so that the deposition rate of H4 as a light emitting host and Ir-12 as a light emitting dopant is 100: 6. And a light emitting layer was provided by vapor deposition to a thickness of 30 nm.
  • the heating boat containing BCP was energized and heated, and a hole blocking layer having a thickness of lOnm was provided at a deposition rate of 0.2;! To 0.2 nm / sec. Further, the heating boat containing Alq was passed through and heated to provide an electron transporting layer having a film thickness of 20 nm at a deposition rate of 0.2;
  • organic EL device 1-1 In the production of organic EL device 1-1, organic EL device 1 1-2 ⁇ ! ⁇ was produced in the same manner except that the light-emitting host, light-emitting dopant, and hole blocking material were changed as shown in Table 1. .
  • the organic EL device produced using the metal complex according to the present invention has higher emission efficiency and longer lifetime while having a short-wave emission of pure blue to blue green compared to the organic EL device of the comparative example. It is clear that a long life can be achieved. In addition, it can be seen that it is useful as a blue light emitting device having a higher blue purity than the organic EL device of the comparative example.
  • Polyburcarbazole hole transporting binder polymer
  • Ir 13 blue light-emitting orthometalated complex
  • 2 (4-biphenyl) -5- (4 t-butylphenyl) 1, 3, 4 —Oxadiazole electron transport material
  • a buttered mask (a mask with a light emitting area of 5 mm x 5 mm) is placed on the organic compound layer, and 0.5 nm of lithium fluoride is deposited as a cathode buffer layer and 150 nm of aluminum is deposited as a cathode in a deposition apparatus.
  • a cathode was provided to produce an organic EL device 21 emitting blue light.
  • Organic EL elements 2-2 to 2-14 were prepared in the same manner as in the preparation of organic EL element 2-1, except that the luminescent dopant was changed as shown in Table 2.
  • the non-light-emitting surface of each organic EL element after fabrication was covered with a glass case, and a glass substrate having a thickness of 300 m was used as the sealing substrate.
  • the epoxy-based photo-curing adhesive (Latus Track LC0629B manufactured by Toagosei Co., Ltd.) is applied as a sealant around the glass substrate, and this is overlaid on the cathode and brought into close contact with the transparent support substrate. Then, UV light was irradiated, cured, sealed, and an illumination device as shown in FIGS. 5 and 6 was formed and evaluated.
  • the organic EL device 112 of Example 1 was used as a blue light emitting device.
  • a green light emitting device was produced in the same manner as in Example 1 except that Ir-12 was changed to Ir-1 in the organic EL device 11 of Example 1, and this was used as a green light emitting device.
  • a red light emitting device was produced in the same manner as in Example 1 except that Ir-12 was changed to Ir-9 in the organic EL device 11 of Example 1, and this was used as a red light emitting device.
  • FIG. 2 shows only a schematic view of the display portion A of the display device thus manufactured. That is, a plurality of pixels 3 (light emitting elements) juxtaposed with a wiring portion including a plurality of scanning lines 5 and data lines 6 on the same substrate. And the scanning line 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning line 5 and the data line 6 Is orthogonal to the grid and is connected to the pixel 3 at the orthogonal position (details not shown).
  • the plurality of pixels 3 are driven by switches that are organic EL elements and active elements corresponding to the respective emission colors.
  • switches that are organic EL elements and active elements corresponding to the respective emission colors.
  • the pixel 3 receives and receives an image data signal from the data line 6. Emits light according to the image data. In this way, a full-color display device was produced by appropriately juxtaposing red, green, and blue pixels.
  • the electrode of the transparent electrode substrate of Example 1 was patterned to 20 mm x 20 mm, and ⁇ -NPD was deposited to a thickness of 25 nm as a hole injection / transport layer on the same as in Example 1, and then H
  • the heated boat containing 4 and the example compound 2—425 and Ir 9 containing boat are energized independently, and the light emitting host HI and the example dopant 2—425 and Ir—
  • the vapor deposition rate of 9 was adjusted to 100: 5: 0.6, vapor deposition was performed to a thickness of 30 ⁇ m, and a light emitting layer was provided.
  • Example 2 a square perforated mask having substantially the same shape as the transparent electrode made of stainless steel was placed on the electron injection layer, and lithium fluoride 0.5 nm as a cathode buffer layer and a cathode as a cathode buffer layer. Aluminum 150nm was deposited.
  • This element was provided with a sealing can having the same method and the same structure as in Example 1, and a flat lamp as shown in Figs. 5 and 6 was produced.
  • a flat lamp as shown in Figs. 5 and 6 was produced.
  • this flat lamp was energized, almost white light was obtained, indicating that it could be used as a lighting device. It was found that white light emission could be obtained in the same manner even if it was replaced with other exemplified compounds.
  • the ITO transparent electrode is formed after patterning on a substrate ( ⁇ Techno Glass Co., Ltd. 45-45) made of ITO (Indium Toxide) on a lOOmmX lOOmm X l. 1mm glass substrate as an anode.
  • the transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • poly (3,4 ethylene dioxythiophene) polystyrene sulfonate (PEDOT / PSS: Bayer, Baytron P A1 4083) diluted to 70% with pure water was formed by spin coating at 3000 rpm for 30 seconds and dried at 200 ° C. for 1 hour to provide a first hole transport layer having a thickness of 30 nm.
  • This substrate was transferred to a nitrogen atmosphere, and a solution of 50 mg of Compound A dissolved in 10 ml of toluene was formed on the first hole transport layer by spin coating at 1000 rpm for 30 seconds. . After irradiating with ultraviolet light for 180 seconds to perform photopolymerization / crosslinking, vacuum drying was performed at 60 ° C. for 1 hour to form a second hole transport layer.
  • a film in which Compound C (20 mg) was dissolved in 6 ml of toluene was used to form a film by spin coating under conditions of 1000 rpm and 30 seconds. Irradiated with ultraviolet light for 15 seconds to cause photopolymerization and crosslinking, and further heated in a vacuum at 80 ° C. for 1 hour to form a hole blocking layer.
  • this substrate was fixed to a substrate holder of a vacuum vapor deposition apparatus, and 200 mg of Alq was put into a molybdenum resistance heating boat and attached to the vacuum vapor deposition apparatus.
  • pressure in the vacuum tank was reduced by 4 X 10- 4 Pa or, and heated by supplying an electric current to the boat charged with Alq, it is deposited on the electron transport layer at a deposition rate of 0. lnm / sec, further film An electron transport layer with a thickness of 40 nm was provided.
  • the substrate temperature during vapor deposition was room temperature.
  • a white light emitting organic EL device was produced.

Abstract

La présente invention concerne un dispositif EL organique utilisant un matériau de dispositif EL organique ayant une longueur d'onde d'émission contrôlée, une efficacité lumineuse élevée et une longue durée de vie d'émission. La présente invention concerne également un dispositif d'affichage et un dispositif d'éclairage. L'invention concerne spécifiquement un matériau de dispositif EL organique représenté par la formule générale suivante (1a). [Dans la formule (1a), A représente un groupe cyclique; B représente un groupe cyclique; et A est un groupe représenté par la formule générale (1b) ci-dessous, ou bien le composé représenté par la formule générale (1a) possède un groupe représenté par la formule générale (1b) ci-dessous comme substituant : (Dans la formule (1b) dans laquelle X représente O, S ou N-R2 (dans laquelle R2 représente un groupe alkyle, un groupe aryle ou un groupe hétéroaryle); Z1, Z2, Z3 et Z4 représentent N ou -CR4= (dans laquelle R4 représente un atome d'hydrogène ou un substituant), et un de ceux-ci représente N); X1 et X2 représentent C, N ou O; L1 représente un groupe atomique formant un ligand bidentate conjointement avec X1 et X2; m1 représente 1, 2 ou 3, m2 représente 0, 1 ou 2 et m1 + m2 est 2 ou 3; et M1 représente un métal des groupes 8 à 10 du tableau périodique.]
PCT/JP2007/069822 2006-10-13 2007-10-11 Matériau de dispositif électroluminescent organique, dispositif électroluminescent organique, dispositif d'affichage et d'éclairage WO2008044723A1 (fr)

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