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WO2006098120A1 - Materiau pour dispositif electroluminescent organique et dispositif electroluminescent organique - Google Patents

Materiau pour dispositif electroluminescent organique et dispositif electroluminescent organique Download PDF

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Publication number
WO2006098120A1
WO2006098120A1 PCT/JP2006/303110 JP2006303110W WO2006098120A1 WO 2006098120 A1 WO2006098120 A1 WO 2006098120A1 JP 2006303110 W JP2006303110 W JP 2006303110W WO 2006098120 A1 WO2006098120 A1 WO 2006098120A1
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group
ring
organic
general formula
represented
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Japanese (ja)
Inventor
Masato Nishizeki
Tomohiro Oshiyama
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Konica Minolta Inc
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Konica Minolta Inc
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Priority to JP2007508045A priority Critical patent/JP5125502B2/ja
Publication of WO2006098120A1 publication Critical patent/WO2006098120A1/fr
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Definitions

  • the present invention relates to an organic electoluminescence device material, an organic electroluminescence device, a display device, and a lighting device.
  • ELD electoric luminescence display
  • examples of ELD constituent elements include inorganic electoluminescence elements and organic electroluminescence elements (hereinafter referred to as organic EL elements).
  • Inorganic electoric luminescence elements have been used as planar light sources, but in order to drive the light emitting elements, an alternating high voltage is required.
  • An organic EL device has a structure in which a light-emitting layer containing a compound that emits light 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.
  • the device emits light using the emission of light (fluorescence 'phosphorescence) when this exciton is deactivated, and can emit light at a voltage of several V to several tens of V. For this reason, it is a thin-film, completely solid element that has a wide viewing angle and high visibility, and is attracting attention from the viewpoints of space saving and portability.
  • organic EL elements for practical use in the future, it is desired to develop organic EL elements that emit light efficiently and with high luminance with lower power consumption.
  • an organic EL device material As an organic electoluminescence device material (hereinafter referred to as an organic EL device material). Doping improves the emission brightness and extends the lifetime of organic EL devices.
  • an organic EL device having an organic light emitting layer in which an 8-hydroxyquinoline aluminum complex is used as a host compound and a small amount of a phosphor is doped therein for example, Japanese Patent Laid-Open No. 63-264692
  • 8 —An organic EL device having an organic light-emitting layer in which a hydroxyquinoline aluminum complex is used as a host compound and doped with a quinatalidone dye see, for example, JP-A-3-255. No. 190 is known.
  • the upper limit of the internal quantum efficiency is 100%. Therefore, in principle, the luminous efficiency is doubled compared to the case 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.
  • the light emission brightness and the light emission efficiency in the case of a light emitting element are greatly improved compared to conventional organic EL elements because the emitted light is derived from phosphorescence.
  • the light emission life of the organic EL device was lower than that of the conventional organic EL device.
  • phosphorescent high-efficiency light-emitting materials are currently unable to achieve sufficient performance for practical use because it is difficult to shorten the emission wavelength and improve the light-emitting lifetime of organic EL elements. .
  • Patent Document 1 Japanese Patent Laid-Open No. 2002-332291
  • Patent Document 2 Japanese Patent Laid-Open No. 2002-332292
  • Patent Document 3 Japanese Patent Laid-Open No. 2002-338588
  • Patent Document 4 Japanese Patent Laid-Open No. 2002-226495
  • Patent Document 5 Japanese Patent Laid-Open No. 2002-234894
  • Patent Document 6 WO02Zl5645 specification
  • Patent Document 7 Japanese Unexamined Patent Publication No. 2003-123982
  • Patent Document 8 Japanese Patent Application Laid-Open No. 2002-117978
  • Patent Document 9 Japanese Patent Laid-Open No. 2003-146996
  • Patent Document 10 WO04Z016711 Specification
  • Non-Patent Document 1 Inorganic Chemistry, No. 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 ⁇ , page 1171 (2002) Disclosure of invention
  • the present invention has been made in view of the related problems, and an object of the present invention is to provide an organic EL element material, an organic EL element, an illumination device, and a display device that exhibit high light emission efficiency and have a long light emission lifetime. Is to provide.
  • ⁇ represents a metal element belonging to Groups 8 to 10 in the periodic table.
  • L and L ′ represent different bidentate ligands, m is 1 or 2, and n is 1 Or 2. However, m + n is 2 or 3, which matches the charge of M.
  • Partial structure ML in which bidentate ligands L and L 'are coordinated to metal M is represented by the following general formula (2), and partial structure ML' is represented by the following general formula (3) or (4) Is done. [0024] [Chemical 2]
  • X represents a carbon atom or a nitrogen atom
  • Q represents a 6-membered aromatic together with the carbon atom and X.
  • X is 0, S, CH, CHR, CR, NR, P
  • R is an alkyl group, cycloalkyl
  • X represents a carbon atom or a nitrogen atom
  • Q represents a 6-membered aromatic together with the carbon atom and X.
  • X is 0, S, CH, CHR, CR, NR, P
  • R is an alkyl group, cycloalkyl
  • X and X represent a nitrogen atom or a phosphorus atom, and X is coordinated to M through X and X
  • a group of atoms forming a bidentate ligand is represented. )
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • Ml is 1 or 2
  • nl is 1 or 2
  • ml + nl is 2 or 3.
  • Yes Matches the charge of M.
  • X represents a carbon or nitrogen atom
  • Q represents a 6-membered aromatic with carbon atom and X
  • X is 0, S, CH, CHR, CR, NR, P
  • R is an alkyl group, cycloalkyl
  • X represents a carbon atom or a nitrogen atom
  • Q represents a 6-membered aromatic together with the carbon atom and X.
  • X represents a carbon atom or a nitrogen atom
  • Q represents a 5- to 6-membered fragrance together with the nitrogen atom and X
  • X is 0, S, CH, CHR, CR, NR,
  • R is an alkyl group, cycloalkyl
  • At least one of the aromatic heterocycle B or the aromatic heterocycle D is a 6-membered ring, and the other is a 5-membered ring
  • M represents a metal element of Groups 8 to 10 in the periodic table of elements.
  • M2 is 1 or 2
  • n2 is 1 or 2.
  • m2 + n2 is 2 or 3.
  • Yes Matches the charge of M.
  • X represents a carbon or nitrogen atom
  • Q represents a 6-membered aromatic with carbon atom and X
  • X is 0, S, CH, CHR, CR, NR, P
  • R is an alkyl group, cycloalkyl
  • a group, an alkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group; X and X are
  • 31 represents an atomic group forming a bidentate ligand coordinated to M through 32.
  • M represents a metal element belonging to Groups 8 to 10 in the periodic table.
  • Nl l and nl2 each represents an integer selected from 0 to 2; X and X are each> N
  • R is an alkyl group, cycloalkyl group, alkenyl
  • R is a hydrogen atom, alkyl group, cycloalkyl
  • X, X , X each represents CH or N, and any one or two of them are N.
  • X is 0, S, C b 19c 0
  • M represents a metal element belonging to Groups 8 to 10 in the periodic table.
  • n21 and n22 each represents an integer selected from 0 to 2.
  • X is> N—R, —O—
  • S R is an alkyl group, cycloalkyl group, alkenyl group, aryl
  • X and X are> N-R, —O or
  • R is a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, aryl
  • X, X, X are each CH or N
  • X is 0, S, CH, CHR, CR, NR, PR,
  • R is an alkyl group, a cycloalkyl group,
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • n31 and n32 represent an integer selected from 0 to 2.
  • X is> N—R, —O—
  • S R is an alkyl group, cycloalkyl group, alkenyl group, aryl
  • X and X are> N-R, —O or
  • R is a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkyl
  • X, X, X are each CH or N
  • X is 0, S, CH, CHR, CR, NR, PR,
  • R is an alkyl group, a cycloalkyl group,
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • X represents a carbon atom.
  • a group of atoms forming ring E which is a 5- to 6-membered aromatic heterocycle.
  • R represents a substituent, and n
  • Xa represents —N (Ra), —O—Ra or —S—Ra
  • the Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. If Xa is — N (Ra), the two Ras are the same but different
  • R is an alkyl group, cycloalkyl group, alkenyl group, aryl group
  • M represents a metal element of Groups 8 to 10 in the periodic table of elements.
  • R 1, R 2, R 3, R 5 Each represents a hydrogen atom or an electron-donating substituent, and at least one is an electron-donating substituent.
  • At least one of 56 58 is an electron-withdrawing substituent.
  • R 1 and R 2 represent a substituent, n51, n5
  • Xa represents —N (Ra), —O—Ra or —S—Ra
  • the Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. If Xa is — N (Ra), the two Ras are the same but different
  • R is an alkyl group, cycloalkyl group, alkenyl group, aryl group
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • 61 is a carbon atom and X, X
  • 61 represents a group of atoms forming a ring F which is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocycle with 63 63, Q is a nitrogen atom and a 5- to 6-membered aromatic together with X and X Form a ring G that is a heterocycle
  • X and X represent substituents whose van der Waals volume is 20 A 3 or more bc
  • m6 and n6 each represents 0 or 1. However, m6 + n6 ⁇ l.
  • X is 0, S, CH, CHR,
  • R is an alkyl group
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • 71 is a carbon atom, X, X
  • 71 73 represents a group of atoms forming a ring H which is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocycle, Q is a nitrogen atom, and a 5- to 6-membered aromatic together with X and X Atom that forms ring K, a heterocycle
  • 74 represents an atomic group forming an aromatic heterocyclic ring with a nitrogen atom.
  • R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
  • the ligand is a partial structure represented by the following general formulas (41) to (433) or tautomers thereof:
  • R represents R —CO— or R —SO—
  • R represents an alkyl group, cycloalkyl
  • R, R, R, R, R, R Represents an alkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
  • n represents an integer of 0 to 3
  • n and n represent an integer of 0 to 2.
  • R is an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group
  • Q represents an atomic group that forms a 5- or 6-membered aromatic heterocycle with carbon and nitrogen
  • Q and Q represent an atomic group that forms a 5-membered aromatic heterocycle with carbon and nitrogen.
  • the organic electoluminescence device material according to item 1.
  • An organic electroluminescent device comprising the organic electroluminescent device according to (1) to (14), wherein the organic electroluminescent device is described above.
  • a light emitting layer is included as a constituent layer, and the light emitting layer contains the organic electoluminescence device material described in any one of (1) to (14) above. Organic electroreductive element.
  • the organic electoluminescence device according to any one of (17).
  • Z represents an aromatic heterocyclic ring
  • Z represents an aromatic heterocyclic ring or an aromatic hydrocarbon ring.
  • Z represents a divalent linking group or a simple bond.
  • R represents a hydrogen atom or a substituent.
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent.
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent.
  • R to R each independently represent a hydrogen atom or a substituent.
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent.
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent.
  • R 1 to R 3 each independently represents a hydrogen atom or a substituent.
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent.
  • R represents a hydrogen atom or a substituent. Also, a plurality of R may be the same or different.
  • R represents a hydrogen atom or a substituent. Further, a plurality of R may be the same or different from each other.
  • the compound represented by the general formula (1A) has at least one group represented by any one of the following general formulas (2A-1) to (2A-10): The organic electoluminescence device according to any one of (1) to (22).
  • R ⁇ R, R ⁇ R, R ⁇ R, R ⁇ R each independently represents a hydrogen atom or a substituent.
  • the substituents may be the same or different.
  • 601 606 are each independently a force representing a hydrogen atom or a substituent R
  • At least one of 601 606 represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10). )
  • R to R each independently represents a hydrogen atom or a substituent having a small force R to R
  • At least one represents at least one group selected from the groups represented by the general formulas (2A-1) to (2A-10). )
  • R to R each independently represents a hydrogen atom or a substituent having a small force R to R
  • At least one represents at least one group selected from the groups represented by the general formulas (2A-1) to (2A-10).
  • At least one of 645 represents at least one group selected from the groups represented by the general formulas (2A-1) to (2A-10). )
  • R 1 to R 4 each independently represents a hydrogen atom or a substituent having a small force
  • R 1 to R 5 each independently represents a hydrogen atom or a substituent having a small force
  • At least one represents at least one group selected from the basic forces represented by the general formulas (2-1) to (2-10).
  • na represents an integer from 0 to 5
  • nb represents an integer from 1 to 6, but the sum of na and nb is 6.
  • R to R each independently represents a hydrogen atom or a substituent having a small force R to R
  • At least one represents at least one group selected from the groups represented by the general formulas (2A-1) to (2A-10). )
  • At least one represents at least one group selected from the basic forces represented by the general formulas (2A-1) to (2A-10).
  • the organic elect described in any one of (18) to (22) above, wherein the compound represented by the general formula (1A) is represented by the following general formula (10A): Mouth luminescence element.
  • R to R each independently represents a hydrogen atom or a substituent
  • L represents a divalent linking group
  • At least one of R 1 to R 4 is represented by the general formulas (2A-1) to (2A-10)
  • R and R each independently represent a hydrogen atom or a substituent.
  • N and m are each an integer of 1 to 2.
  • R and R each independently represent a hydrogen atom or a substituent.
  • N and m are each an integer of 1 to 2.
  • R and R each independently represent a hydrogen atom or a substituent.
  • N and m are each an integer of 1 to 2.
  • R and R each independently represent a hydrogen atom or a substituent.
  • N and m are each an integer of 1 to 2.
  • R and R each independently represent a hydrogen atom or a substituent.
  • N and m are each an integer of 1 to 2.
  • Z, Z and Z each represents a 6-membered aromatic heterocyclic ring containing at least one nitrogen atom.
  • o and p each represent an integer of 1 to 3
  • Ar and Ar each represent an arylene group or a divalent aromatic group.
  • Z and Z are each a 6-membered aromatic compound containing at least one nitrogen atom.
  • ⁇ and ⁇ each represent an integer of 1 to 3
  • Ar and Ar each represent an arylene group or a divalent aromatic group.
  • Z, Z, Z, and Z are each a 6-membered good containing at least one nitrogen atom.
  • a display device comprising the organic electroluminescent device according to any one of (15) to (48).
  • an organic EL element material it is possible to provide an organic EL element material, an organic EL element, an illumination device, and a display device that exhibit high luminous efficiency and have a long emission lifetime.
  • Fig. 1 is a schematic diagram showing an example of a display device that also has organic EL element power.
  • 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 display device.
  • FIG. 5 is a schematic view of a lighting device.
  • FIG. 6 is a cross-sectional view of the lighting device.
  • the organic EL element containing the organic EL element material means that the organic EL element material forms any organic layer constituting the organic EL element, or the organic layer. This represents the organic EL element contained in.
  • the layer structure of the organic EL element of the present invention will be described separately in detail.
  • a light emitting layer and / or a hole blocking layer are preferable.
  • it When it is contained in the light emitting layer, it can be used as a light emitting dopant in the light emitting layer to achieve a long emission life of the organic EL device which is the object of the present invention.
  • organic EL element material of the present invention and preferred embodiment (1) of the present invention is an ortho metal complex represented by the general formula (1).
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • L and 1 / represent different bidentate ligands, m is 1 or 2, and n is 1 or 2. However, m + n is 2 or 3, which matches the charge of M.
  • the partial structure ML is represented by the general formula (2), and the partial structure ML 'is represented by the general formula (3) or Is represented by (4).
  • X represents a carbon atom or a nitrogen atom
  • Q represents a 6-membered aromatic together with the carbon atom and X.
  • X is 0, S, CH, CHR, CR, NR, P
  • R is an alkyl group, cycloalkyl
  • X represents a carbon atom or a nitrogen atom
  • Q represents a 6-membered aromatic together with the carbon atom and X.
  • X is 0, S, CH, CHR, CR, NR, P
  • R is an alkyl group, cycloalkyl
  • X and X represent a nitrogen atom or a phosphorus atom, and X is coordinated to M through X and X
  • a group of atoms forming a bidentate ligand is represented.
  • Examples of the 6-membered aromatic hydrocarbon ring include a benzene ring.
  • Examples of the 5- to 6-membered aromatic heterocycle include oxazole ring, thiophene ring, furan ring, pyrrole ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, And a triazole ring.
  • 6-membered aromatic hydrocarbon rings and 5- to 6-membered aromatic heterocycles are alkyl groups (eg, methyl group, ethyl group, propyl group, isopropyl group, (t) butyl group, pentyl group).
  • cycloalkyl group eg, cyclopentyl group, cyclohexyl group, etc.
  • alkenyl group eg, vinyl group, aryl) Group
  • alkynyl group for example, propargyl group, etc.
  • aryl group also called aromatic hydrocarbon ring group, for example, phenyl group, tolyl group, xylyl group, naphthyl group, biphenyl-allyl group, anthryl group, phenanthryl
  • heterocyclic group for example, pyrrolidyl group, imidazolidyl group, morpholyl group, oxazolidyl group, etc.
  • aromatic heterocyclic group for example, pyridyl group, Rimijiniru group,
  • acetyl, ethyl carbo, propyl carbo Group pentyl carbo yl group, cyclohexyl carbo yl group, octyl carbo ol group, 2-ethyl hexyl carbo yl group, dodecyl carbo carb yl group, vinyl carbo yl group, naphthyl carbo yl group, Pyridyl carbon Group), acyloxy group (for example, acetyloxy group, ethylcarbo-loxy group, butylcarbo-loxy group, octylcarbonyl-oxyl group, dodecylcarbonyloxy group, phenylcarbonyloxy group, etc.), amido group (for example, methyl Carbonylamino group, ethyl carbolumino group, dimethyl carbolumino group, propyl carbolumino group
  • Forced rubamoyl groups for example, aminoamino group, methylaminocarbol group, dimethylaminocarbole group, open pyraminocarbol group, pentylaminocarbo ol group, cyclohexylamino
  • Carbon group Octylaminocarbol group, 2-Ethylhexylaminocarbol group, Dodecylaminocarbol group, Phenylaminocarbol group, Naphtylaminocarbol group, 2— Pyridylaminocarbol group, etc.
  • sulfier groups eg methylsulfur
  • the alkyl group, cycloalkyl group, alkyl group, aryl group, bicyclic group, and aromatic heterocyclic group represented by R are each a 6-membered aromatic hydrocarbon ring, a 5- to 6-membered group, respectively. These are synonymous with the alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group, and aromatic heterocyclic group described as the substituent of the aromatic heterocyclic group.
  • the organic EL device material of the aspect (2) is an ortho metal complex represented by the general formula (5).
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • ml is 1 or 2 and nl is 1 or 2.
  • nl + nl is 2 or 3, which matches the charge of M.
  • X represents a carbon atom or a nitrogen atom
  • Q represents a 6-membered aromatic together with the carbon atom and X
  • X is 0, S, CH, CHR, CR, NR, P
  • R is an alkyl group, cycloalkyl
  • X represents a carbon atom or a nitrogen atom
  • Q represents a 6-membered aromatic together with the carbon atom and X.
  • X is 0, S, CH, CHR, CR, NR,
  • R is an alkyl group, cycloalkyl
  • 6-membered aromatic hydrocarbon ring 5- to 6-membered aromatic heterocycle, and R have the same meanings as described in the embodiment (1).
  • At least one of the aromatic heterocycle B or the aromatic heterocycle D is preferably a 6-membered ring and the other is preferably a 5-membered ring.
  • the organic EL device material of the aspect (4) is an ortho metal complex represented by the general formula (6).
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • m2 is 1 or 2
  • n2 is 1 or 2.
  • m2 + n2 is 2 or 3, which matches the charge of M
  • X represents a carbon atom or a nitrogen atom
  • Q represents a 6-membered aromatic together with the carbon atom and X
  • Q is a 5- to 6-membered aromatic together with the nitrogen atom and X A group of atoms forming ring B which is a heterocyclic ring.
  • X is 0, S, CH, CHR, CR, NR, P
  • R is an alkyl group, cycloalkyl
  • a group, an alkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group; X and X are
  • 6-membered aromatic hydrocarbon ring 5- to 6-membered aromatic heterocycle, and R have the same meanings as described in the embodiment (1).
  • the aromatic heterocycle B is preferably a 6-membered ring.
  • the organic EL device material of the aspect (6) is an ortho metal complex having a partial structure represented by the general formulas (1-1) to (1-150) or a tautomer thereof as a partial structure. It is characterized by being.
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • R and R are
  • nl l and nl2 each represents an integer selected from 0 to 2.
  • X and X are each> N
  • R represents one O or S.
  • R is an alkyl group, cycloalkyl group, alkenyl
  • R is a hydrogen atom, alkyl group, cycloalkyl
  • X each represents CH or N, and any one or two of them are N.
  • X is 0, S, C b 19c 0
  • R 1 and R 2 is the 6-membered aromatic hydrocarbon described in the embodiment (1).
  • alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).
  • the organic EL device material of the aspect (7) is an ortho metal complex having a partial structure represented by the general formulas (2-1) to (2-50) or a tautomer thereof as a partial structure. It is characterized by being. [0160] In the formula, M represents a metal element of Groups 8 to 10 in the periodic table. R and R are
  • n21 and n22 each represents an integer selected from 0 to 2.
  • X is> N—R, —O—
  • S R is an alkyl group, cycloalkyl group, alkenyl group, aryl
  • X and X are> N-R, —O or
  • R is a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, aryl
  • X, X, X are each CH or N
  • X is 0, S, CH, CHR, CR, NR, PR,
  • R is an alkyl group, a cycloalkyl group,
  • R 1 and R 2 is the 6-membered aromatic hydrocarbon described in the embodiment (1).
  • alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).
  • the organic EL device material of the aspect (8) is an ortho metal complex having a partial structure represented by the general formulas (3-1) to (3-10) or a tautomer thereof as a partial structure. It is characterized by being.
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • R and R are
  • n31 and n32 represent an integer selected from 0 to 2.
  • X is> N—R, —O—
  • S R is an alkyl group, cycloalkyl group, alkenyl group, aryl
  • X and X are> N-R, —O or
  • R is a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, aryl
  • X, X, X are each CH or N
  • X is 0, S, CH, CHR, CR, NR, PR,
  • R is an alkyl group, a cycloalkyl group,
  • R 1 and R 2 is the 6-membered aromatic hydrocarbon described in the embodiment (1).
  • alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group is the same as the above-described embodiment (1 ) Is synonymous with that described above.
  • the organic EL device material of the aspect (9) is an ortho metal complex having a partial structure represented by the general formula (7) or a tautomer thereof as a partial structure.
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • X is a carbon atom
  • Q is a carbon atom and X together with a 6-membered aromatic hydrocarbon ring or
  • a group of atoms forming ring E which is a 5- to 6-membered aromatic heterocycle.
  • R represents a substituent, and n
  • Xa represents —N (Ra), —O—Ra or —S—Ra
  • the Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. If Xa is — N (Ra), the two Ras are the same but different
  • R is an alkyl group, cycloalkyl group, alkenyl group, aryl group
  • R 1 is a 6-membered aromatic hydrocarbon ring described in the embodiment (1),
  • alkyl group, cycloalkyl group, alkenyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).
  • the orthometal complex having a partial structure represented by the general formula (7) or a tautomer thereof as a partial structure is a partial structure represented by the general formula (8) or (9) or a tautomer thereof. It is preferable that it is an ortho metal complex which has an active substance as a partial structure.
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • At least one of 56 58 is an electron-withdrawing substituent.
  • R 1 and R 2 represent a substituent, n51, n5
  • Xa represents —N (Ra), —O—Ra or —S—Ra
  • the Ra represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. If Xa is — N (Ra), the two Ras are the same but different
  • R is an alkyl group, cycloalkyl group, alkenyl group, aryl group Represents a heterocyclic group or an aromatic heterocyclic group.
  • the electron-donating substituent is a substituent having a negative Hammett ⁇ ⁇ value described below, and such a substituent has an electron closer to the bonding atom side than a hydrogen atom. It is easy to give.
  • substituent exhibiting an electron donating property include a hydroxyl group, an alkoxy group (for example, methoxy group,), an acetyloxy group, an amino group, a dimethylamino group, an acetylamino group, an alkyl group (for example, a methyl group, Ethyl group, propyl group, tert-butyl group, etc.) and aryl group (eg, phenyl group, mesityl group, etc.).
  • a cycloprovir group (one 0.21), a cyclohexyl group (—0.22), a tert-butyl group (—0.0. 20), — CH Si (CH) (— 0.
  • ⁇ ⁇ value of Met and Met refers to Hammett's substituent constant ⁇ ⁇ .
  • Hammett's ⁇ ⁇ value is the substituent constant determined by Hammett et al. For the electronic effect of the substituents on the hydrolysis of ethyl benzoate. “Structure-activity relationship of drugs” (Nanedo: 1979) , Rsubstituent Constants for Correlation Analysis chemistry and biology (C. Hansch and A. Leo, John Wiley & Sons, New York, 1979), etc. can be cited.
  • the electron-donating substituent is most preferably an alkyl group, an alkoxy group, or an alkylamino group.
  • the substituent is synonymous with the substituent of the 6-membered aromatic hydrocarbon ring or 5- to 6-membered aromatic heterocycle described in the embodiment (1).
  • the alkyl group, cycloalkyl group, alkyl group, aryl group, heterocyclic group or aromatic heterocyclic group is the same as described in the embodiment (1). It is synonymous with.
  • the organic EL device material of the aspect (11) is an ortho metal complex having a partial structure represented by the general formula (10) or a tautomer thereof as a partial structure.
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • 61 is a carbon atom and X, X
  • 61 represents a group of atoms that together with 63 form ring F, which is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring.
  • Q forms a ring G, which is a 5- to 6-membered aromatic heterocycle, together with the nitrogen atom and X ⁇ ilO—L, X.
  • k A represents a substituent that is 3 or more h
  • M6 each represents 0 or 1. However, m6 + n6 ⁇ l.
  • X is 0, S, CH, CHR,
  • R is an alkyl group
  • the 6-membered aromatic hydrocarbon ring and the 5- to 6-membered aromatic heterocyclic ring have the same meanings as described in the embodiment (1).
  • VDW van der Waals
  • alkyl group, cycloalkyl group, alkyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).
  • the orthometal complex having a partial structure represented by the general formula (10) or a tautomer thereof as a partial structure is a partial structure represented by the general formulas (11) to (14) or a tautomer thereof. It is preferable that it is an ortho metal complex which has an active substance as a partial structure.
  • M represents a metal element of Groups 8 to 10 in the periodic table.
  • 71 71 73 represents a group of atoms forming ring H which is a 6-membered aromatic hydrocarbon ring or a 5- to 6-membered aromatic heterocyclic ring, Q is a nitrogen atom, and 5 to 6-membered aromatic together with X and X Atoms forming ring K, a heterocyclic ring
  • 74 represents an atomic group forming an aromatic heterocyclic ring with a nitrogen atom.
  • R represents an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
  • the 6-membered aromatic hydrocarbon ring and the 5- to 6-membered aromatic heterocyclic ring have the same meanings as described in the embodiment (1).
  • alkyl group, cycloalkyl group, alkyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).
  • the organic EL device material of the embodiment (13) is X — X of the general formula (4) or the general formula (6).
  • the bidentate ligand formed by -X is represented by the general formulas (4 1) to (4 31)
  • R represents R —CO— or R —SO—
  • R represents an alkyl group, cycloalkyl
  • R, R, R, R, R, R Represents an alkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
  • n represents an integer of 0 to 3
  • n and n represent an integer of 0 to 2.
  • R is an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group
  • Q represents an atomic group that forms a 5- or 6-membered aromatic heterocycle with carbon and nitrogen
  • Q 1 and Q 2 represent an atomic group that forms a 5-membered aromatic heterocycle with carbon and nitrogen.
  • the 5- to 6-membered aromatic heterocyclic ring has the same meaning as described in the embodiment (1).
  • alkyl group, cycloalkyl group, alkyl group, aryl group, heterocyclic group or aromatic heterocyclic group has the same meaning as described in the embodiment (1).
  • the organic EL device material of the aspect (14) is characterized in that, in all the general formulas, it is an orthometallic complex which is M force iridium or platinum.
  • the organic EL element material is contained in any of the constituent layers (organic layers) constituting the organic EL element to produce an organic EL element.
  • the organic EL element preferably has a light emitting layer as a constituent layer, and the light emitting layer preferably contains the organic EL element material. When it is contained in the light emitting layer, it can be used as a light emitting dopant in the light emitting layer to achieve a long emission life of the organic EL device which is the object of the present invention.
  • the organic EL element has a hole blocking layer as a constituent layer, and the hole blocking layer includes the organic E
  • the organic EL device of the aspect (18) is characterized by containing the compound represented by the general formula (1A).
  • Z represents an aromatic heterocyclic ring
  • Z represents an aromatic heterocyclic ring or an aromatic hydrocarbon ring.
  • Z represents a divalent linking group or a simple bond.
  • R is a hydrogen atom or a substituent
  • Z may have a substituent! Represents an aromatic heterocyclic ring, and Z is
  • R 3 represents a divalent linking group or a simple bond.
  • 101 represents a hydrogen atom or a substituent.
  • Aromatic heterocycles represented by Z and Z include furan ring, thiophene ring, pyridine ring,
  • Examples of the aromatic hydrocarbon ring represented by Z include a benzene ring, biphenyl ring, and naphthalene ring.
  • the aromatic hydrocarbon ring is represented by R described later.
  • Examples of the substituent represented by R include an alkyl group (for example, methyl group, ethyl group, propyl group).
  • cycloalkyl group for example, cyclopentyl group, cyclohexyl group, etc.
  • Alkenyl group for example, buyl group, allyl group, etc.
  • alkynyl group for example, ethynyl group, propargyl group, etc.
  • aryl group for example,
  • aromatic heterocyclic group e.g. furyl group, chael group, pyridyl group, pyridazyl group, pyrimidyl group, pyrazyl group, triazinyl group, imidazolyl group, Pyrazolyl group, thiazolyl group, quinazolyl group, phthalazinyl group, etc.
  • heterocyclic group eg, pyrrolidyl group, imidazolidyl group, morpholyl group, oxazolidyl group, etc.
  • alkoxyl group eg, methoxy group, ethoxy group, propyloxy group
  • cycloalkoxyl group eg, cyclopentyloxy group, cyclohexyloxy group, etc.
  • substituents may be further substituted with the above substituents.
  • a plurality of these substituents may be bonded to each other to form a ring.
  • the substituent is an alkyl group, a cycloalkyl group, a fluorinated hydrocarbon group, an aryl group, or an aromatic heterocyclic group.
  • Examples of the divalent linking group represented by Z include alkylene, alkylene, alkylene, and aryl.
  • heteroatoms In addition to hydrocarbon groups such as mono-ene, compounds containing heteroatoms may also be used, and compounds having aromatic heterocycles such as thiophene 2, 5 diyl group or pyrazine 2, 3 diyl group (heteroaromatics) It may be a divalent linking group derived from a compound) or a chalcogen atom such as oxygen or sulfur. Further, it may be a group in which heteroatoms such as an alkylimino group, dialkylsilane diyl group or diarylgermandyl group are linked to each other.
  • a mere bond is a bond that directly bonds the linking substituents together.
  • the Z-membered ring represented by the general formula (1A) is preferable. This is because the Z-membered ring represented by the general formula (1A) is preferable. This is because the Z-membered ring represented by the general formula (1A) is preferable.
  • the luminous efficiency can be further increased. Further, the life can be extended.
  • a Z-membered ring is preferable. This increases the luminous efficiency.
  • both 2 are 6-membered rings because the luminous efficiency can be further increased. Further, it is preferable because the lifetime can be further increased.
  • the compound represented by the general formula (1A) has a molecular weight of 450 or more, which can increase the luminous efficiency and prolong the life.
  • the compound represented by the general formula (1A) is preferably a compound represented by the general formula (1A-1) to (: LA
  • R to R each independently represent a hydrogen atom or a substituent.
  • R to R each independently represent a hydrogen atom or a substituent.
  • R to R each independently represent a hydrogen atom or a substituent.
  • R to R each independently represent a hydrogen atom or a substituent.
  • R to R each independently represent a hydrogen atom or a substituent.
  • R to R each independently represent a hydrogen atom or a substituent.
  • R to R each independently represent a hydrogen atom or a substituent.
  • R to R each independently represent a hydrogen atom or a substituent.
  • R represents a hydrogen atom or a substituent.
  • the plurality of R may be the same or different.
  • R represents a hydrogen atom or a substituent.
  • the plurality of R may be the same or different.
  • Compound represented by general formula (1 A-10) By using, an organic EL element with higher luminous efficiency can be obtained. Furthermore, it can be a long-life organic EL device.
  • the compound represented by the general formula (1A) is preferably a compound having at least one group represented by any one of the general formulas (2A-1) to (2A-10). It is. In particular, it is more preferable to have 2 to 4 groups represented by the deviations of the general formulas (2A-1) to (2A-10) in the molecule.
  • the structure represented by the general formula (1A) includes a case where R is removed and the part is replaced by the general formulas (2A-1) to (2A-10).
  • R to R represent a hydrogen atom or a substituent.
  • At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
  • R to R represent a hydrogen atom or a substituent.
  • At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
  • R to R represent a hydrogen atom or a substituent.
  • At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
  • R to R represent a hydrogen atom or a substituent.
  • At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
  • R to R represent a hydrogen atom or a substituent.
  • At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
  • na represents an integer from 0 to 5
  • nb represents an integer from 1 to 6, but the sum of na and nb is 6.
  • R to R represent a hydrogen atom or a substituent.
  • At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
  • R ⁇ R represents a hydrogen atom or a force representing a substituent R ⁇
  • At least one R is a group represented by any of the formulas (2A-1) to (2A-10).
  • R 1 to R 4 represent a hydrogen atom or a force representing a substituent R
  • At least one of ⁇ R is represented by! /, Deviation of the general formulas (2A-1) to (2A-10)
  • Examples of the divalent linking group represented by L include an alkylene group (for example, ethylene group, trimethylene).
  • At least one of carbon atoms constituting the divalent linking group is a chalcogen atom (oxygen, sulfur, etc.) N (R) —may be substituted with a group or the like.
  • the divalent linking group represented by L for example, a group having a divalent heterocyclic group is used.
  • a group having a divalent heterocyclic group is used.
  • the alkylimino group, the dialkylsilane diyl group, and the diarylgermandyl group may be a group that connects and connects hetero atoms
  • each of Z, Z, Z, and Z each represents a small number of nitrogen atoms.
  • 6-membered aromatic heterocycle containing at least one examples include a pyridine ring, a pyridazine ring, a pyrimidine ring, and a pyrazine ring.
  • each of the nitrogen atoms represented by Z and Z is at least
  • 6-membered aromatic heterocycle including one pyridine examples include a pyridine ring, a pyridazine ring, a pyrimidine ring, and a pyrazine ring.
  • the arylene groups represented by Ar and Ar include o-phenylene group and m-phenylene group, respectively.
  • P phenylene group naphthalene diyl group, anthracenedyl group, naphthacene diyl group, pyrene diyl group, naphthyl naphthalene diyl group, biphenyl group (for example, 3, 3'-biphenyl group, 3, 6-biphenyl group) Etc.), terfelsyl group, quaterfel group, kink feldsyl group, sexiphenyl group, septiphenyl group, octaphenyl group, nobiphenyl group, decyl group and the like.
  • the arylene group may further have a substituent described later.
  • the divalent aromatic heterocyclic groups represented by Ar and Ar are respectively a furan ring, a thiophene ring,
  • Examples of the divalent linking group represented by L include those represented by L in the general formula (10A).
  • Power that is synonymous with a valent linking group is preferably an alkylene group or a divalent group containing a chalcogen atom such as OS or the like, and most preferably an alkylene group.
  • the aromatic heterocyclic group represented by 1 2 1 2 is represented by Ar and Ar in the general formula (16A).
  • 6-membered aromatics each represented by Z, Z, Z, Z, each containing at least one nitrogen atom
  • heterocyclic ring examples include a pyridine ring, a pyridazine ring, a pyrimidine ring, and a pyrazine ring.
  • the divalent linking group represented by L is represented by L 2 in the general formula (10A).
  • Power that is synonymous with a valent linking group is preferably an alkylene group, a divalent group containing a chalcogen atom such as os-, and most preferably an alkylene group.
  • the compound according to the present invention preferably has a molecular weight of 00 or more, more preferably 450 or more, still more preferably 600 or more, and particularly preferably a molecular weight of 800 or more. As a result, the glass transition temperature is raised, the thermal stability is improved, and the life can be further extended.
  • Z electron transport layer Z cathode (m) anode Z hole transport layer Z light emitting layer Z hole blocking layer Z electron transport layer Z cathode transport layer Z cathode Gv) anode Z hole transport layer Z light emitting layer Z hole blocking layer Z electron transport layer Z Cathode buffer layer Z cathode (V) anode Z anode buffer layer Z hole transport layer Z light-emitting layer Z hole blocking layer Z electron transport layer Z cathode buffer layer Z cathode
  • 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, conductive transparent materials such as Cul, indium tinoxide (ITO), SnO, and ZnO. IDIXO (In O—ZnO) etc.
  • the anode if these electrode materials are formed into a thin film by a method such as vapor deposition or sputtering and a pattern of a desired shape can be formed by a photolithography method, or the pattern accuracy is not so required (About 100 ⁇ m or more), the pattern may be formed through a mask of a desired shape during the deposition or sputtering of the electrode material. In the case of taking out light emission from this anode, it is desirable to make the transmittance larger than 10%, and the sheet resistance as the anode is preferably several hundred ⁇ Z or less. Further, the film thickness is a force depending on the material. Usually, 10 to: LOOOnm, preferably 10 to 2 OOnm is selected.
  • a cathode having a work function (4 eV or less) metal referred to as an electron injecting metal
  • an alloy referred to as an electrically conductive compound
  • a mixture thereof is used.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium Z copper mixture, magnesium Z silver mixture, magnesium Z aluminum mixture, magnesium Z indium mixture, aluminum Z acid aluminum UM (Al 2 O 3) mixture, indium, lithium
  • the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. Also, the sheet resistance as a cathode is several hundred ⁇ / mouth or less, and the preferred film thickness is usually ⁇ ! ⁇ 5 ⁇ m, preferably selected in the range of 50 to 200 nm. In addition, since the emitted light is transmitted, it is convenient that either the anode or the cathode of the organic EL element is transparent or semi-transparent to improve the emission luminance.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
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Abstract

L’invention décrit un matériau pour dispositif EL organique présentant un rendement lumineux élevé tout en offrant une longue durée de vie d'émission. Sont également décrits un dispositif EL organique, un dispositif d’éclairage et un afficheur. L'invention décrit plus spécifiquement un matériau pour dispositif EL organique caractérisé en ce qu'il est composé d'un complexe orthométallique de formule générale suivante (1). [Formule chimique 1] MLmL'n (1) (Dans cette formule, M représente un groupe de 8 à 10 éléments métalliques du tableau périodique des éléments ; L et L' représentent chacun un ligand bidentate différent l’un de l’autre ; m représente 1 ou 2 ; et n représente 1 ou 2. Dans cette configuration, m + n vaut 2 ou 3 et est égal à la charge électrique de M. La structure partielle ML est représentée par la formule générale (2) ci-dessous, tandis que la structure partielle ML' est représentée par la formule générale (3) ou (4) ci-dessous.) [Formule chimique 2] (2) (3) (4)
PCT/JP2006/303110 2005-03-16 2006-02-22 Materiau pour dispositif electroluminescent organique et dispositif electroluminescent organique Ceased WO2006098120A1 (fr)

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