WO2006103874A1 - Materiau de dispositif electroluminescent organique, dispositif electroluminescent organique, ecran et dispositif d’eclairage - Google Patents

Materiau de dispositif electroluminescent organique, dispositif electroluminescent organique, ecran et dispositif d’eclairage Download PDF

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WO2006103874A1
WO2006103874A1 PCT/JP2006/304234 JP2006304234W WO2006103874A1 WO 2006103874 A1 WO2006103874 A1 WO 2006103874A1 JP 2006304234 W JP2006304234 W JP 2006304234W WO 2006103874 A1 WO2006103874 A1 WO 2006103874A1
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group
substituent
general formula
organic
partial structure
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Masato Nishizeki
Tomohiro Oshiyama
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Konica Minolta Holdings, Inc.
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    • 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 luminescence element
  • the present invention relates to a novel organic electoluminescence element material, organic electroluminescence element, display device, and illumination device.
  • ELD electoric luminescence display
  • organic EL elements organic electroluminescence 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 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. It is an element that emits light using the emission of light (fluorescence 'phosphorescence) when this exciton is deactivated. It can emit light at a voltage of several to several tens of volts, and is self-luminous. As a result, it is a thin-film, completely solid element with a wide viewing angle and high visibility.
  • 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 device.
  • 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 combined with a host compound.
  • a device 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 doubled compared to the excited singlet case, and almost the same performance as a cold cathode tube is obtained. It is also attracting attention as a lighting application because of its potential.
  • many compounds are synthesized and studied mainly with heavy metal complexes such as iridium complexes. ing.
  • Tetsuo Tsutsui et al. also used tris (2— (p-tolyl) pyridine) iridium (Ir (Ir ( ptpy)),
  • metal complexes are commonly referred to as orthometalated iridium complexes. ).
  • the ligand of the ortho metal complex is a 5-membered heterocycle containing one non-nitrogen atom such as a thiophene ring or a furan ring in the metal coordination part such as cherubiridine.
  • a ligand there are several examples of using a ligand, but the structure proposed by them is bound to the 2nd and 3rd positions of a 5-membered heterocycle, each containing one non-nitrogen atom.
  • long-wavelength light emission such as yellow to red for the complexes using the ligands that are hand-held (see, for example, Patent Documents 2 and 11 to 16).
  • 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 International Publication No. 02Z015645 Pamphlet
  • 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 Pamphlet of International Publication No. 04Z016711
  • Patent Document 11 Japanese Unexamined Patent Application Publication No. 2002-175884
  • Patent Document 12 Japanese Patent Laid-Open No. 2001-181617
  • Patent Document 13 Japanese Unexamined Patent Publication No. 2001-247959
  • Patent Document 14 Japanese Unexamined Patent Publication No. 2003-73355
  • Patent Document 15 Japanese Unexamined Patent Publication No. 2003-81989
  • Patent Document 16 Japanese Patent Laid-Open No. 2003-272861
  • 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 Tsuji, page 1171 (2002) Disclosure of invention
  • the present invention has been made in view of the above problems, and an object of the present invention is to provide an organic electoluminescence device material exhibiting high luminous efficiency and a long luminous lifetime, and an organic electoluminescence device using the same. Furthermore, another object of the present invention is to provide an illumination device and a display device using the organic electoluminescence element.
  • An organic electoluminescence device material comprising an ortho metal complex having a partial structure represented by the following general formula (Z):
  • R represents a hydrogen atom or a substituent.
  • L together with nitrogen atom is a 5-7 member b
  • M represents a metal element of Group 8 to Group 10 in the periodic table.
  • X represents 0, S, SO or SO
  • R represents a substituent.
  • R is a hydrogen atom or
  • X 1, X 2, X 3 and X 3 each represent C, C—R, N, N—R, O or S;
  • R is a hydrogen atom or a substituent
  • M represents a metal element of Group 8 to Group 10 in the periodic table.
  • R is a hydrogen atom or
  • X 1, X 2, X 3 and X each represent C—R or N, and a carbon atom, nitrogen
  • R represents a hydrogen atom or a substituent
  • M represents a metal element of Group 8 to Group 10 in the periodic table.
  • R is a hydrogen atom or
  • X 1, X 2, X 3 and X 3 each represent C, C—R, N, N—R, O or S;
  • R is a hydrogen atom or a substituent
  • R is an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, a heterocyclic ring
  • M is a group 8-10 metal in the periodic table Represents an element.
  • R is a hydrogen atom or
  • 40 2 7 8 represents a substituent.
  • R represents an alkyl group, a cycloalkyl group, an alkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
  • M represents a metal element of Group 8 to Group 10 in the periodic table.
  • R represents a substituent
  • R represents a hydrogen atom or a substituent.
  • At least R and R The other is an electron-donating substituent or an electron-withdrawing substituent.
  • X is
  • R represents a substituent
  • n51 represents an integer selected from 0 to 3.
  • Ra is an alkyl group, a cycloalkyl group,
  • R represents a substituent
  • R represents a hydrogen atom or a substituent. At least R and R
  • One of 56 57 56 57 is an electron-donating substituent or an electron-withdrawing substituent.
  • X is
  • Xa represents o, s, so or SO.
  • R represents a substituent, and n52 represents an integer selected from 0 to 3.
  • Ra is an alkyl group, a cycloalkyl group,
  • R is an alkyl group
  • M represents a metal element of Group 8 to Group 10 in the periodic table.
  • X represents a group of atoms that form a 5-membered aromatic heterocyclic ring
  • Q is a carbon atom
  • R represents a substituent
  • R represents a hydrogen atom or a substituent
  • R 1, R 2 and R 3 represent a substituent having a van der Waals volume of 20 A 3 or more.
  • n63 represents 0 or 1; However, n61 + n62 ⁇ l. M represents a metal element of Group 8 to Group 10 in the periodic table. ]
  • X represents a group of atoms that form a 6-membered aromatic heterocycle with Q being a carbon atom, X, X
  • R represents a substituent
  • R represents a hydrogen atom or a substituent
  • R, R 1, R 2 and R 3 each represent a substituent having a van der Waals volume of 20 A 3 or more.
  • n63 represents 0 or 1; However, n61 + n62 ⁇ l. M represents a metal element of Group 8 to Group 10 in the periodic table. ]
  • X represents a group of atoms that form a 5-membered aromatic heterocyclic ring
  • Q is a carbon atom
  • R represents a substituent
  • R represents a hydrogen atom or a substituent
  • R 1, R 2 and R 3 represent a substituent having a van der Waals volume of 20 A 3 or more.
  • n73 represents 0 or 1; However, n71 + n72 ⁇ l.
  • X is 0, S, CH, CHR, C
  • R is an alkyl group, cyclo
  • M represents a metal element of Group 8 to Group 10 in the periodic table.
  • X represents a group of atoms that form a 6-membered aromatic heterocycle with Q being a carbon atom, X, X
  • R represents a substituent
  • R represents a hydrogen atom or a substituent
  • R 1, R 2 and R 3 represent a substituent having a van der Waals volume of 20 A 3 or more.
  • n73 represents 0 or 1; However, n71 + n72 ⁇ l.
  • X is 0, S, CH, CHR, C
  • R is an alkyl group, cyclo
  • M represents a metal element of Group 8 to Group 10 in the periodic table.
  • An organic electoluminescence device comprising the organic electroluminescence device material described in 1 above in at least one of the constituent layers.
  • An organic electroluminescent device comprising a luminescent layer as a constituent layer, wherein the luminescent layer contains the organic electroluminescent device material described in 1 above.
  • a display device comprising the organic-electric-luminescence element as described in 13 above.
  • an organic electoluminescence that exhibits high luminous efficiency and has a long luminous lifetime. It was possible to provide a light emitting device material, an organic electroluminescence device using the same, and an illumination device and a display device using the organic electroluminescence device.
  • FIG. 1 is a schematic view showing an example of a display device configured with organic EL element power.
  • FIG. 2 is a schematic diagram of display unit A.
  • FIG. 3 is an equivalent circuit diagram of a drive circuit constituting 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 inventors of the present invention have bonded to the 3rd and 4th positions of a 5-membered heterocycle containing one non-nitrogen atom in the portion coordinated to the metal as the ligand of the ortho metal complex. It has been found that when a ligand with a hand-held partial structure is used, it emits light with a short wavelength such as blue to blue-green, showing high luminous efficiency and greatly improving the luminous lifetime. It was. Note that the partial structure described in the present invention includes a partial structure of a tautomer thereof.
  • the organic electoluminescence device material of the present invention is characterized by containing an ortho metal complex having a partial structure represented by the general formula (Z).
  • X is 0, S, SO or SO.
  • R represents a substituent.
  • R is a hydrogen atom or
  • L forms a 5- to 7-membered aromatic heterocycle with the nitrogen atom.
  • M represents a group 8-10 metal element in the periodic table. M is preferably iridium or gold.
  • the inclusion layer in the organic electoluminescence device material of at least one orthometal complex selected from the partial structure group consisting of the general formulas (1) to (4) according to the present invention includes a light emitting layer or a positive layer.
  • the hole blocking layer is preferred and contained in the light-emitting layer, it can be used as a light-emitting dopant in the light-emitting layer, thereby achieving an increase in the light-emitting lifetime of the organic EL device that is the object of the present invention.
  • X is 0, S, SO or SO
  • R represents a substituent.
  • R represents a hydrogen atom or a substituent.
  • 1 2 11 12 13 14 each represents C, C—R, N, N—R, O or S, and a 5-membered fragrance together with a nitrogen atom Forming a family heterocycle.
  • R represents a hydrogen atom or a substituent.
  • Examples of the substituent represented by R and R include an alkyl group (for example, a methyl group, an ethyl group,
  • Isopropyl group hydroxyethyl group, methoxymethyl group, trifluoromethyl group, tert-butyl group, pentyl group, octyl group, nor group, decyl group, etc.
  • cycloalkyl group for example, cyclopentyl group, cyclohexyl group
  • Xyl group etc.
  • aralkyl groups eg, benzyl group, 2-phenethyl group, etc.
  • aryl groups eg, phenyl group, p-chlorophenyl group, mesityl group, tolyl group, xylyl group, biphenyl-yl.
  • heterocyclic group eg, pyrrolidyl group, imidazolyl group, morpholyl group, oxazolidyl group, etc.
  • aromatic heterocyclic group eg, furyl group, chenyl group, pyridyl group, Pyridazinyl group, pyrimidinyl group, birazinyl group, triazinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, quinazolyl Group, carbazolyl group, carbolyl group, diazacarbazolyl group (Diazacarbazolyl group is a group in which any one of the carbon atoms constituting the carboline ring of the carbolinyl group is substituted with a nitrogen atom.
  • alkoxy group eg, ethoxy group, isopropoxy group, butoxy group, etc.
  • aryloxy group eg, phenoxy group, naphthyloxy group, etc.
  • cyano group hydroxyl group
  • alkenyl group eg, A butyl group, a styryl group, a halogen atom (eg, a chlorine atom, a bromine atom, an iodine atom, a fluorine atom, etc.), more preferably an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group, an aromatic group.
  • Group heterocyclic group may be further substituted.
  • X 1, X 2, X 3 and X 4 each represent C, C—R, N, N—R, O or S, and a nitrogen atom
  • 5-membered aromatic heterocycle examples include imidazole ring, pyrazole ring, isothiazole ring, isoxazole ring, oxazole ring, thiazole ring, And a triazole ring.
  • the partial structure represented by the general formula (1) according to the present invention is also selected from the partial structure group forces represented by the following general formulas (1) -1 to (1) -15 It is preferable that at least one partial structure is formed.
  • nl represents an integer selected from 0 to 2, respectively.
  • X is 0, S,
  • SO represents SO or SO
  • X represents> N—R, —O or —S, respectively.
  • R is al
  • M represents a metal element of Group 8 to Group 10 in the periodic table.
  • R 1, R 2, and R 3 are the same as the substituents represented by R 1 and R 2 in the general formula (1).
  • the partial structure represented by the general formula (1) according to the present invention is: It is preferably a partial structure represented by the general formula (7A) or the general formula (8A).
  • X 1, X 2, X 3 and X 4 are each a carbon base paper.
  • Q represents a 5-membered aromatic heterocycle with carbon, X, X and nitrogen atoms.
  • X and X represent 0, S, SO or SO.
  • R represents a substituent
  • R represents a hydrogen atom or a substituent.
  • R, R, R, R are van der Waals volumes
  • Force S20A represents a substituent that is 3 or more.
  • n61, n62, and n63 represent 0 or 1. However, n61 + n62 ⁇ 1.
  • M represents a metal element of Group 8 to Group 10 in the periodic table.
  • R 1 and R 2 are the same as the substituents represented by R 1 and R 2 in the general formula (1).
  • Q is an element that forms a 5-membered aromatic heterocycle with carbon atoms, X and X.
  • the 5-membered aromatic heterocycle includes an oxazole ring, a thiophene ring, a furan ring, a pyrrole ring, an imidazole ring, a pyrazole ring, and a triazole ring.
  • Q is an element that forms a 5-membered aromatic heterocycle with carbon, X, X, and nitrogen.
  • the 5-membered aromatic heterocycle includes an oxazole ring, pyrrole ring, imidazole ring, pyrazole ring, triazole ring and the like.
  • R 1, R 2, R 3 and R 4 each represent a substituent having a van der Waals volume of 20 A 3 or more,
  • VDW van der Waals
  • the van der Waals (VDW) volume of the substituent is a parameter obtained using the molecular simulation software Cerius 2 manufactured by Accelrys, Inc., but the substituent is introduced into the benzene ring and the Dreiding Force Field is used. Optimized molecular structure by MM calculation and defined as Volume value obtained by using Connnoly Surface. The specific volume of van derunoles (VDW) of the substituent is shown below.
  • R 1, R 2, R 3, and R 4 are specifically methyl, ethyl, and isopropyl groups.
  • X is 0, S, SO or SO
  • 21 22 23 24 each represents C R or N, and together with a carbon atom and a nitrogen atom, a 6-membered aromatic heterocycle
  • M is group 8 in the periodic table
  • X 1, X 2, X 3 and X each represent C—R or N, and a carbon atom
  • a 6-membered aromatic heterocycle is formed together with the nitrogen atom, and specific examples of the powerful 6-membered aromatic heterocycle include a pyridine ring, a pyrimidine ring, a pyridazine ring, and a pyrazine ring.
  • the partial structure represented by the general formula (2) according to the present invention is also selected from the partial structural group forces represented by the following general formulas (2) -1 to (2) -6 It is preferable that at least one partial structure is formed.
  • R 1 and R 2 each represent a substituent, and R 1 represents hydrogen
  • n2 represents an integer selected from 0 to 2.
  • X is 0, S, SO
  • M represents a metal element of Group 8 to Group 10 in the periodic table.
  • R 1, R 2 and R 3 are the same as the substituents represented by R and R in the general formula (1).
  • the partial structure represented by the general formula (2) is preferably a partial structure represented by the general formula (5).
  • R represents a substituent
  • At least one of 52 is an electron donating substituent or an electron withdrawing substituent.
  • X represents 0, S, SO or SO.
  • R is a substitution
  • Xa is —N (Ra), —O—Ra or
  • S—Ra Ra represents an alkyl group, a cycloalkyl group, an alkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group. If Xa is — N (Ra), the two Ras are the same
  • M represents a metal element of Group 8 to Group 10 in the periodic table.
  • R 1, R 2 and R 3 are the same as the substituents represented by R and R in the general formula (1).
  • Ra includes the same groups as R in formula (3) described later. At least one of R and R is an electron-donating substituent or an electron-withdrawing moiety.
  • the electron-donating substituent has a negative value for Hammett's substituent constant ⁇ ⁇ .
  • hydroxy group, alkoxy group (for example, methoxy group), acyloxy group (for example, acetyloxy group, benzoyloxy group), amino group, dimethylamino group, acetylamino group, alkyl group ( For example, a methyl group, a propyl group), an aryl group (for example, a phenyl group, a mesityl group), etc. are mentioned.
  • an electron-withdrawing substituent is a group in which Hammett's substituent constant ⁇ ⁇ exhibits a positive value, and specifically, a cyano group, an alkoxycarbonyl group, an aryloxycarbol group.
  • the heterocyclic group is a saturated or unsaturated heterocyclic group, for example, pyridyl group, quinolyl group, quinoxalinyl group, pyrazinyl group, benzotriazolyl group, imidazolyl group, benzimidazolyl group, hydantoin 1
  • examples thereof include a ruthenium group, a succinimide group, and a phthalimide group.
  • the partial structural force represented by the general formula (2) is preferably a partial structure represented by the general formula (7 () or the general formula (8 ⁇ ).
  • Q represents a 6-membered aromatic heterocycle with carbon, X, X and nitrogen atoms.
  • X and X represent 0, S, SO or SO.
  • R represents a substituent
  • R represents a hydrogen atom or a substituent.
  • R, R, R, R are van der Waals volumes
  • 20 A represents a substituent that is 3 or more.
  • n61, n62, 1163 [0 or 1]. However, n61 + n 62 ⁇ 1.
  • M represents a metal element of Group 8 to Group 10 in the periodic table.
  • R 1 and R 2 are the same as the substituents represented by R 1 and R 2 in the general formula (1).
  • Q is an element that forms a 6-membered aromatic heterocycle with carbon atoms, X and X.
  • the six-membered aromatic heterocycle includes a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, and a triazine ring.
  • Q is a carbon atom, X, X, nitrogen This represents an atomic group that forms a 5-membered aromatic heterocycle with an atom.
  • Examples of the 6-membered aromatic heterocycle include a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, and a triazine ring.
  • R 1, R 2, R 3 and R 4 represent a substituent having a van der Waals volume of 20 A 3 or more
  • Examples thereof include the same groups as those represented by the general formula (7A) or the general formula (8A).
  • X is 0, S, SO or SO
  • R represents a substituent.
  • R represents a hydrogen atom or a substituent.
  • 5 6 31 32 33 34 each represents C, C—R, N, N—R, O or S, and a 5-membered fragrance together with a nitrogen atom
  • R represents a hydrogen atom or a substituent.
  • X is 0, S, CH, CHR
  • R is an alkyl group
  • X 1, X 2, X 3, and X 3 are C, C—R, N, N—R, O, or S, respectively.
  • 5-membered aromatic heterocycle together with the nitrogen atom.
  • Specific examples of the 5-membered aromatic heterocycle include those listed in the general formula (1).
  • R represents an alkyl group (for example, a methyl group, an ethyl group, an isopropyl group, a hydroxyethyl group, a methoxymethyl group, a trifluoromethyl group, a tbutyl group, a pentyl group, an octyl group, a nor group, Decyl group, etc.), cycloalkyl group (eg, cyclopentyl group, cyclohexyl group, etc.), alkenyl group (eg, vinyl group, etc.), aryl group (eg, phenyl group, p-chlorophenyl group, mesityl group, A tolyl group, a xylyl group, a biphfylyl group, a naphthyl group, an anthryl group, a phenanthryl group, etc.), a heterocyclic group (eg, pyrrolidyl group, imidazo
  • the partial structure represented by the general formula (3) is at least one partial structure in which partial structural group forces represented by the following general formulas (3) -1 to (3) -15 are also selected. Preferably there is.
  • n3 represents an integer selected from 0 to 2, respectively.
  • X is 0, S,
  • SO represents SO or SO
  • X represents> N—R, —O— or —S—, respectively.
  • R is al
  • R represents an alkyl group, a cycloalkyl group, an alkyl group, an aryl group, a double group Represents a unicyclic group or an aromatic heterocyclic group.
  • M represents a metal element of Group 8 to Group 10 in the periodic table.
  • R 1, R 2 and R 3 are the same as the substituents represented by R and R in the general formula (1).
  • the partial structure represented by A) is preferred.
  • X 1, X 2, X 3, and X 4 are each a carbon atom.
  • Q represents a 5-membered aromatic complex with carbon, X, X and nitrogen atoms.
  • a group of atoms forming a ring is represented.
  • X and X represent 0, S, SO or SO.
  • R is a substituent
  • R represents a hydrogen atom or a substituent.
  • R, R, R, R are van der Waals
  • n71, n72, and n73 represent 0 or 1. However, n71 + n72 ⁇ l.
  • C represents NR, SO, SO.
  • R represents an alkyl group, a cycloalkyl group, an alkyl group, an alkyl
  • M represents a metal element of Group 8 to Group 10 in the periodic table.
  • R 1 and R 2 are the same as the substituents represented by R 1 and R 2 in the general formula (1).
  • the 5-membered aromatic heterocyclic ring and van der Waals volume are the same as those in the general formula (7A) or the general formula (8A).
  • Specific examples of R include the same groups as R in the general formula (3).
  • X is 0, S, SO or SO
  • R represents a substituent.
  • R represents a hydrogen atom or a substituent.
  • R represents a hydrogen atom or a substituent.
  • X is 0, S, CH, CHR, C (R),
  • R is an alkyl group, cycloal
  • M Represents group 8 to group 10 metal elements in the periodic table.
  • X 1, X 2, X 3 and X each represent C—R or N, and a carbon atom
  • a 6-membered aromatic heterocycle is formed together with the nitrogen atom.
  • Specific examples of the powerful 6-membered aromatic heterocycle are those listed in the general formula (2).
  • Specific examples of R include the same groups as R in the general formula (3).
  • the partial structure represented by the general formula (4) is preferably a partial structure represented by the general formula (6).
  • R represents a substituent
  • R represents a hydrogen atom or a substituent
  • the At least one of R and R is an electron donating substituent or an electron withdrawing substituent.
  • X represents 0, S, SO or SO.
  • R represents a substituent, and n52 is selected from 0 to 3
  • Xa represents —N (Ra), —O—Ra or —S—Ra.
  • Ra is alkyl
  • Xa is —N (Ra)
  • the two Ras may be the same or different.
  • R represents an alkyl group, a cycloalkyl group, an alkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
  • M represents a group 8-10 metal element in the periodic table
  • R 1, R 2 and R 3 are the same as the substituents represented by R and R in the general formula (1).
  • Ra include the same groups as R in the general formula (3).
  • R may be the same as R in the general formula (3).
  • the partial structure represented by the general formula (4) is at least one partial structure in which a partial structure group force consisting of the following general formulas (4) -1 to (4) -6 is also selected. It is preferable.
  • R 1 and R 2 each represents a substituent, and R 1 represents a hydrogen atom.
  • n4 represents an integer selected from 0 to 2.
  • X is 0, S, SO or S
  • R represents an alkyl group, a cycloalkyl group, an alkyl group, an aryl group, a double group
  • M represents a metal element of Group 8 to Group 10 in the periodic table.
  • R include the same groups as R in the general formula (3).
  • X 1, X 2, X 3 and X 5 are each a carbon atom.
  • 73 74 represents a group of atoms that together with the nitrogen atom form a 6-membered aromatic heterocycle.
  • n71, n72, and n73 represent 0 or 1. However, n71 + n72 ⁇ l.
  • C represents NR, SO, SO.
  • R represents an alkyl group, a cycloalkyl group, an alkyl group, an alkyl Represents an aryl group, a heterocyclic group or an aromatic heterocyclic group.
  • M represents a metal element of Group 8 to Group 10 in the periodic table.
  • the 6-membered aromatic heterocycle and van der Waals volume are the same as those in the general formula (7B) or the general formula (8B).
  • Specific examples of R include the same groups as R in the general formula (3).
  • Preferred orthometal complexes according to the present invention include a minus monovalent monodentate ligand together with a ligand having a partial structure represented by the general formula (Z), Negative monovalent bidentate ligands, uncharged monodentate ligands, and uncharged bidentate ligands, especially in combination with negative monovalent terionic monodentate ligands. It is preferred to use a monodentate ligand of charge. It is preferably used in combination with a minus monovalent terionic monodentate ligand. Examples of the uncharged monodentate ligand include the below-mentioned uncharged monodentate ligand.
  • a monodentate ligand having an ionic nature selected from group A shown below.
  • R is an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group.
  • R represents a substituent
  • n8 represents an integer selected from 0 to 3.
  • R 1 include the same groups as R except for the alkenyl group of the general formula (3).
  • a negative monovalent bidentate ligand selected from the following partial structures.
  • R 1, R 2 and R 3 each represents an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
  • R represents a substituent, and n9 represents
  • N1 represents an integer of 0 to 3
  • nlO represents an integer of 0 to 2.
  • R represents R—CO— or R—SO, and R represents an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
  • Q forms a 5- to 6-membered aromatic heterocycle with carbon and nitrogen.
  • Q forms a 5-membered aromatic heterocycle with carbon and nitrogen.
  • R 1, R 2 and R 3 are alkyls. Represents a group, a cycloalkyl group, an aryl group, a heterocyclic group or an aromatic heterocyclic group.
  • R is
  • n9 represents an integer of 0 to 3
  • nlO represents an integer of 0 to 2.
  • R is R —CO
  • R is an alkyl group, cycloalkyl group, aryl group, complex
  • Q is a 5- or 6-membered aromatic heterocycle with carbon and nitrogen
  • Q forms a 5-membered aromatic heterocycle with carbon and nitrogen.
  • R 1, R 2, R 3 and R 4 are the same as those of R except for the alkenyl group of the general formula (3).
  • an uncharged bidentate ligand selected from the following partial structure groups.
  • R R R represents an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group or
  • A1 represents a substituent
  • R R R R R R represents a hydrogen atom or a substituent.
  • nl2 represents an integer of 0 3.
  • nl3 represents an integer of 0 4.
  • nl6 represents an integer of 0 2.
  • nl7 represents an integer of 0 2 and
  • nl 8 represents an integer of 0 3.
  • nl9 represents an integer of 04.
  • n20 n22 represents an integer of 0 2 and n21 represents an integer of 0 4.
  • n23 represents an integer of 0 2 and n24 represents an integer of 0 4.
  • 10 11 12 13 represents an atomic group forming a 5 6 aromatic heterocycle with carbon and nitrogen.
  • R R R The specific group of R is the same as R except for the alkenyl group of the general formula (3).
  • R R R R represents a substituent represented by R R in the general formula (1).
  • R represents an alkyl group, a cycloalkyl group, an aryl group, a heterocyclic group, or an aromatic compound.
  • B2 represents an aryl group or an aromatic heterocyclic group.
  • R include the same groups as R except for the alkenyl group of the general formula (3).
  • R 1, R 2, R 3, and R 4 are aryl groups and aromatic heterocyclic groups in the general formula (3).
  • the ortho metal complex has any one of the following uncharged ligands selected from the group B group.
  • R 1, R 2, R 3, R 4, R 5 are an alkyl group, a cycloalkyl group, an aryl group
  • R represents a substituent, and n25 represents 0 to 2
  • R 1, R 2, R 3, R 4, and R 5 are represented by the general formula (3).
  • the organic EL element containing the above organic EL element material means that the organic EL element material forms any organic layer constituting the organic EL element or the organic EL contained in the organic layer. Represents an element.
  • the organic EL device material of the present invention When the organic EL device material of the present invention is applied to an organic EL device, it is contained in at least one of the constituent layers of the organic EL device, and has a light emitting layer as a constituent layer, and the light emitting layer It contains the organic electoluminescence device material of the present invention. Moreover, it is preferable to have a hole blocking layer as a constituent layer and to contain the organic electoluminescence device material of the present invention in the hole blocking layer. In addition, it is preferable that at least one of the constituent layers contains a carbazole derivative.
  • an organic EL element When an organic EL element is produced using the organic EL element material of the present invention, it is preferably used for a light emitting layer or a hole blocking layer in the constituent layers (details will be described later) of the organic EL element. Good. In the light emitting layer, as described above, it is preferably used as a light emitting dopant.
  • the mixing ratio of the light-emitting dopant to the light-emitting host that is the host compound as the main component in the light-emitting layer is preferably adjusted to a range of 0.1 to less than 30% by mass.
  • the luminescent dopant may be a mixture of a plurality of types of compounds.
  • the mixed partner may have a different structure, and other metal complexes or phosphorescent dopants or fluorescent dopants having other structures may be used. Good.
  • dopants phosphorescent dopant, fluorescent dopant, etc.
  • the light-emitting dopant is roughly classified into two types: a fluorescent dopant that emits fluorescence and a phosphorescent dopant that emits phosphorescence.
  • Typical examples of the former include coumarin dyes, pyran dyes, cinine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamines. And dyes such as a dye, a pyrylium dye, a perylene dye, a stilbene dye, a polythiophene dye, or a rare earth complex phosphor.
  • a complex compound containing a metal belonging to Group 8, Group 9, or Group 10 in the periodic table of elements is preferable, and an iridium compound or a phosphine is more preferable.
  • the most preferred U is iridium compounds.
  • 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 ortho metal complex according to the present invention is preferably used in combination with the above-mentioned ortho metal complex!
  • the light-emitting host (simply referred to as “host”! Means the compound with the highest mixing ratio (mass) in the light-emitting layer composed of two or more types of compounds.
  • One pant compound also simply referred to as dopant) ".
  • compound A is a dopant compound
  • compound B is a host compound. It is.
  • the luminescent host used in the present invention a compound having a shorter wavelength than the phosphorescent 0-0 band of the luminescent dopant used in combination is preferably used as the luminescent dopant.
  • the phosphorescent 0-0 band is preferably 450 nm or less as the light-emitting host.
  • the luminescent host according to the present invention is not particularly limited in terms of structure, but is typically a carbazole derivative, a triarylamine derivative, an aromatic borane derivative, a nitrogen-containing heterocyclic compound, thiophene.
  • Preferred compounds include those having a basic skeleton such as derivatives, furan derivatives and oligoarylene compounds and having the 0-0 band force of 50 nm or less.
  • the light emitting host according to the present invention may be a low molecular compound, a high molecular compound having a repeating unit, or a low molecular compound having a polymerizable group such as a vinyl group or an epoxy group (evaporation polymerizable light emitting host). ,,.
  • a compound that has a hole transporting ability and an electron transporting ability, prevents an increase in the wavelength of light emission, and has a high Tg (glass transition temperature) is preferable.
  • the organic EL device material of the present invention is preferably used in the light emitting layer, but in addition to these, the above-mentioned known light emitting host and light emitting dopant are used together. Use it.
  • the light emitting layer contains a compound represented by the following general formula (A). I like it. These compounds are preferably used as a light emitting host in the light emitting layer.
  • Z is an element forming an aromatic heterocyclic ring which may have a substituent.
  • Z represents an aromatic heterocycle or an aromatic hydrocarbon ring which may have a substituent.
  • R is hydrogen
  • Aromatic heterocycles represented by the atomic group forces of Z and Z include furan rings, thiophene rings, and pyri rings.
  • the aromatic hydrocarbon ring represented by the atomic group of Z includes a benzene ring, a biphenyl ring,
  • the aromatic hydrocarbon ring may have a substituent represented by R 1 described later.
  • Examples of the substituent represented by R include an alkyl group (for example, a methyl group, an ethyl group, a 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.
  • halogen atom eg, fluorine atom, chlorine atom, bromine atom, etc.
  • fluorinated hydrocarbon group eg, fluoromethyl group, trifluoromethyl 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.
  • the divalent linking group may be a hydrocarbon group such as alkylene, alkene, alkylene, arylene, etc., or may contain a heteroatom or thiophene 2, 5 diyl group. It may be a divalent linking group derived from a compound having an aromatic heterocycle such as a pyrazine 2,3 diyl group (also referred to as a heteroaromatic compound), or it may be a force lucogen atom such as oxygen or sulfur. There may be. Further, it may be a group that joins heteroatoms such as an alkylimino group, a dialkylsilane diyl group, or a diarylgermandyl group.
  • a mere bond is a bond that directly bonds the linking substituents together.
  • the ring formed by Z in the general formula (A) is preferably a 6-membered ring.
  • the ring formed by Z is preferably a 6-membered ring. This Thereby, the luminous efficiency can be further increased. In addition, the life can be further extended. Furthermore, if both Z and Z are 6-membered rings, the luminous efficiency can be further increased.
  • the light emitting layer according to the present invention can be formed by forming the above compound by a known thin film method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method.
  • the thickness of the light emitting layer is not particularly limited, but is usually selected in the range of 5 nm to 5 m.
  • This light emitting layer may be a single layer structure having one or more of these light emitting materials and / or a laminated structure composed of a plurality of layers having the same composition or different compositions! / ⁇ .
  • this light-emitting layer is made into a solution by dissolving the above-mentioned light-emitting material in a solvent together with a binder such as a resin. It can be formed as a thin film by spin coating or the like.
  • the film thickness of the light-emitting layer thus formed can be appropriately selected according to the situation where there is no particular limitation, but is usually in the range of 5 nm to 5 ⁇ m.
  • Blocking layer electron blocking layer, hole blocking layer >>
  • the blocking layer for example, electron blocking layer, hole blocking layer
  • the thickness of the blocking layer according to the present invention is preferably 3 to: LOOnm, more preferably 5 to 30 nm.
  • the hole blocking layer has the function of an electron transport layer, which is a material force that has the function of transporting electrons while transporting holes and is extremely small, and blocks holes while transporting electrons. By doing so, the probability of recombination of electrons and holes can be improved.
  • the organic EL device material of the present invention can be preferably used for the hole blocking layer in an adjacent layer adjacent to the light emitting layer, such as a hole blocking layer and an electron blocking layer.
  • Examples of the hole blocking layer include, for example, Japanese Patent Application Laid-Open Nos. 11 204258 and 11 204359, and “The Front Line of Organic EL Devices and Their Industrialization (November 30, 1998, NTT Corporation)
  • the hole blocking (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 hole blocking layer according to the present invention preferably contains the compound represented by the general formula (1).
  • the hole blocking layer according to the present invention preferably contains a boron derivative.
  • the electron blocking layer has the function of a hole transport layer in a broad sense, and is a material force that has a function of transporting holes and an extremely small capacity of transporting electrons, and transports holes while transporting holes. The probability of recombination of electrons and holes can be improved by blocking the children.
  • the structure of the positive hole transport layer mentioned later can be used as an electron blocking layer as needed.
  • 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.
  • the hole transport layer can be provided as a single layer or a plurality of layers.
  • a hole transport material there is no particular limitation. Conventionally, in a photoconductive material, it is commonly used as a hole charge injection transport material, and used for a hole injection layer and a hole transport layer of an EL element. Any known one can be selected and used.
  • the hole transport material has a hole injection or transport, electron barrier property! /, Or a deviation, and may be either organic or inorganic.
  • triazole derivatives oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazones Derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
  • aromatic tertiary amine compounds and styrylamine compounds include N, N, N ', N' —tetraphenyl 4, 4 '— diaminophenol; N, N '—Diphenyl 1 N, N, —Bis (3-methylphenol) 1 [1, 1' —Biphenyl] 4,4 ′ —Diamine (TPD); 2, 2-bis (4 di — P-tolylaminophenol) propane; 1, 1 bis (4 di-p-tolylaminophenol) cyclohexane; N, N, N ′, N ′ —tetra-p-tolyl-1,4,4′—diaminobiphenol 1, 1 bis (4 di-l-triaminophenol) 4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenol) phenyl methane; bis (4 di-l-triaminophenol) phenol methane; N , N '—Dihu
  • the hole transport material of the hole transport layer preferably has a fluorescence maximum wavelength at 415 nm or less, and more preferably has a 0-0 band of phosphorescence of 450 nm or less. Also, the hole transport material is preferably high Tg! /.
  • This 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. Can do.
  • the film thickness of the hole transport layer is not particularly limited, but is usually about 5 to 500 Onm.
  • the hole transport layer may have a single layer structure composed of one or more of the above materials.
  • the electron transport layer is a material force 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.
  • the electron transport layer can be a single layer or a plurality of layers.
  • an electron transport material also serving as a hole blocking material used for an electron transport layer adjacent to the light emitting layer on the cathode side is as follows. The following materials are known. Furthermore, the electron transport layer only needs to have a function of transmitting electrons injected from the cathode to the light emitting layer, and any material can be selected from conventionally known compounds. .
  • electron transport materials examples include: -to-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, and heterocyclic rings such as naphthalene perylene. Examples thereof include tetracarboxylic anhydrides, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, and oxadiazole derivatives.
  • 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.
  • a polymer material in which these materials are introduced into a polymer chain or these materials as a polymer main chain 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-dibromo 1 8 quinolinol) aluminum, tris (2methyl 8-quinolinol) aluminum, tris (5-methyl 8-quinolinol) aluminum, bis (8-quinolinol) zinc (Zn q), and the central metals of these metal complexes
  • Metal complexes in which In, Mg, Cu, Ca, Sn, Ga, or Pb are replaced 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 transporting material.
  • the distyrylvirazine derivative exemplified as the material for the light emitting layer can also be used as an electron transport material, and, like the hole injection layer and the hole transport layer, n-type-Si, n-type-SiC, etc. These inorganic semiconductors can also be used as electron transport materials.
  • the electron transport layer may 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. it can. Although there is no restriction
  • This electron transport layer has a single layer structure composed of one or more of the above materials. It may be made.
  • 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. Hey.
  • the injection layer is a layer provided between the electrode and the organic layer in order to reduce the drive voltage and improve the luminance of the light emission.
  • the organic EL element and its industry front line June 30, 1998) Chapter 2 “Electrode materials” (pages 123-166) of “Part 2” of “Tees Co., Ltd.”) describes the details of the hole injection layer (anode buffer layer) and the electron injection layer (cathode buffer). One layer).
  • anode buffer layer (hole injection layer) The details of the anode buffer layer (hole injection layer) are also described in JP-A-9-45479, JP-A-9260062, JP-A-8-288069 and the like.
  • a phthalocyanine buffer layer typified by phthalocyanine, an oxide buffer layer typified by vanadium oxide, an amorphous carbon buffer layer, a polymer buffer layer using a conductive polymer such as polyarene (emeraldine) or polythiophene Etc.
  • cathode buffer layer (electron injection layer) is also described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like.
  • strontium 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
  • acid salt typified by acid aluminum
  • strontium Metal buffer layer typified by aluminum
  • alkali metal compound buffer layer typified by lithium fluoride
  • alkaline earth metal compound buffer layer typified by magnesium fluoride
  • acid salt typified by acid aluminum
  • the buffer layer (injection layer) preferably has a very thin film thickness, although the film thickness is preferably in the range of 0.1 to LOOnm.
  • This injection layer can be formed by thin-filming 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 The injection layer may have a single-layer structure that also has 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 substances include conductive transparent materials such as metals such as Au, Cul, indium tin oxide (ITO), SnO, and ZnO. IDIXO (In O
  • 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 sheet resistance as the anode is preferably several hundreds ⁇ or less.
  • the film thickness is a force depending on the material. Usually, 10 to L000 nm, preferably 10 to 200 nm is selected.
  • 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 referred to as an electron injecting metal
  • an alloy an electrically conductive compound
  • a mixture thereof a mixture thereof.
  • electrode materials include sodium, sodium-powered rhodium alloy, magnesium, lithium, magnesium Z copper mixture, magnesium Z silver mixture, magnesium / aluminum mixture, magnesium Z indium mixture, aluminum Z acid aluminum (Al 2 O 3) mixture, indium, lithium Z aluminum mixture, dilute
  • Examples include earth metals.
  • the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
  • the sheet resistance as a cathode is several hundred ⁇ / mouth or less, and the preferred film thickness is Usually 10 to: L000 nm, preferably 50 to 200 nm.
  • the anode or the cathode of the organic EL element is transparent or translucent to improve the light emission luminance.
  • 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.
  • the substrate is a resin film capable of giving flexibility to the organic EL element.
  • Examples of the resin film include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, and polycarbonate. (PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP) and the like.
  • an inorganic film or an organic film, or a hybrid film of both of them may be formed, and the water vapor transmission rate is 0.01 gZm 2 'dayatm or less. I prefer to be there.
  • the external extraction quantum efficiency of light emission at room temperature 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
  • Z the number of electrons flown through the organic EL element ⁇ 100.
  • a hue improving filter such as a color filter may be used in combination.
  • a roughened film (such as an antiglare film) can be used in combination in order to reduce unevenness in light emission.
  • the organic EL element having at least two different emission maximum wavelengths When used as a multicolor display device, the organic EL element having at least two different emission maximum wavelengths will be described. A preferred example of producing an organic EL element will be described.
  • an organic EL device comprising a Z cathode will be described.
  • a desired electrode material for example, a thin film having a material force for an anode is formed on a suitable substrate at 1 ⁇ m or less, preferably ⁇ !
  • An anode is formed by a method such as vapor deposition or sputtering so as to have a film thickness of ⁇ 200 nm.
  • 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, and an electron transport layer, which is an element material, is formed thereon.
  • the deposition conditions may vary due to kinds of materials used, generally boat temperature 50 to 450 ° C, vacuum degree of 10- 6 ⁇ : LO- 2 Pa, deposition rate 0 It is desirable to select as appropriate within the range of 01 to 50 nmZ seconds, substrate temperature—50 to 300 ° C., and film thickness of 0.1 nm to 5 ⁇ m.
  • a thin film having a cathode material force is formed thereon by 1 ⁇ m or less, preferably by a method such as vapor deposition or sputtering so as to have a film thickness in the range of 50 nm to 200 nm.
  • a desired organic EL device can be obtained.
  • the organic EL device is preferably manufactured from the hole injection layer to the cathode consistently by a single evacuation, 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 may be monochromatic or multicolored, a multicolor display device will be described here.
  • 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 inkjet method, and the printing method are preferable. In the case of using the vapor deposition method, patterning using a shadow mask is preferable. In addition, the production order is reversed, the cathode, the electron transport layer, the holes It is also possible to produce a blocking layer, a light emitting layer, a hole transport layer, and an anode in this order.
  • the multicolor display device can be used as a display device, a display, and various light sources. Display devices and displays can be displayed in full color by using three types of organic EL elements that emit blue, red, and green light.
  • Examples of the display device and display include a television, a computer, a mopile device, an AV device, a character broadcast display, and an information display in a car.
  • the driving method when used as a display device for reproducing moving images which may be used as a display device for reproducing still images or moving images, may be either a simple matrix (passive matrix) method or an active matrix method.
  • Light emitting light sources include home lighting, interior lighting, clock and liquid crystal backlights, billboard advertisements, traffic lights, light sources for optical storage media, light sources for electrophotographic copying machines, light sources for optical communication processors, light sensors Although a light source etc. are mentioned, it is not limited to this.
  • the lighting device of the present invention will be described.
  • the organic EL element having a resonator structure as described above may be used as an organic EL element having a resonator structure in the organic EL element of the present invention.
  • Examples include, but are not limited to, light sources for electrophotographic copying machines, light sources for optical communication processors, and light sources for optical sensors. Further, it may be used for the above application by causing laser oscillation.
  • the organic EL device of the present invention may be used as a kind of lamp such as an illumination or exposure light source, a projection device of a type for projecting an image, a still image or a moving image. It may be used as a type of display device (display) that is directly visible.
  • the drive system when used as a display device for video playback is a simple matrix (passive matrix) Either the method or the active matrix method.
  • a full color display device can be produced 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 constituted by an organic EL element cover. It 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 also 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, and the pixel for each scanning line is imaged by the scanning signal.
  • the data signal light is sequentially emitted and image scanning is performed, and image information is displayed on the display unit A.
  • FIG. 2 is a schematic diagram of display unit A.
  • the display unit A includes a wiring unit including a plurality of scanning lines 5 and data lines 6, a plurality of pixels 3 and the like on a substrate.
  • the main members of the display unit A will be described below.
  • FIG. 2 shows the case where the light emitted from 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 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 appropriately arranging pixels in the red region, the green region, and the blue region on the same substrate.
  • FIG. 3 is a schematic diagram of a pixel.
  • the pixel is an organic EL element 10, a switching transistor 11, a driving transistor 12, a capacitor It has 13 mag.
  • Full-color display can be performed by using red, green, and blue light-emitting organic EL elements as the organic EL elements 10 for a plurality of pixels and arranging them on the same substrate.
  • control unit B force also applies the image data signal to the drain of the switching transistor 11 via the data line 6.
  • a scanning signal is applied to the gate of the switching transistor 11 via the control unit B force 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, and the organic EL element is connected from the power supply line 7 according to the potential of the image data signal applied to the gate. Current is supplied to element 10.
  • the driving of the switching transistor 11 is turned off. However, even if the driving of the switching transistor 11 is turned off, the capacitor 13 holds the potential of the charged image data signal, so that the driving of the driving transistor 12 is kept on and the next scanning signal is applied.
  • the organic EL device 10 continues to emit light until it is seen.
  • the driving transistor 12 is driven according to the potential of the next image data signal synchronized with the scanning signal, and the organic EL element 10 emits light.
  • the organic EL element 10 emits light by providing a switching transistor 11 and a drive transistor 12 which are active elements for the organic EL elements 10 of each of the plurality of pixels, and the organic EL elements 10 of each of the plurality of pixels 3.
  • the flash is activated.
  • Such a light emission 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, or a predetermined light emission amount by a binary image data signal. On, even a talent! /.
  • the potential of the capacitor 13 can be maintained until the next scanning signal is applied. Yo! , And it can be discharged just before the next scan signal is applied!
  • FIG. 4 is a schematic diagram of a display device based on a noisy 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 noisy matrix method pixel 3 has no active elements, and manufacturing costs can be reduced.
  • the organic EL element material of the present invention can also be applied to an organic EL element that emits substantially white light as a lighting device.
  • a plurality of light emitting colors are simultaneously emitted by a plurality of light emitting materials to obtain white light emission by color mixing.
  • the combination of multiple emission colors may include three emission maximum wavelengths of blue, green, and blue, or the complementary colors such as blue and yellow, blue-green and orange 2 may be used. 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 (light-emitting dopants), a fluorescent material or a phosphorescent material that emits phosphorescence. Any combination of a dye material that emits light from the light emitting material as excitation light may be used, but in the white organic EL device according to the present invention, a method of combining a plurality of light emitting dopants is preferable.
  • the layer structure of the organic EL device for obtaining a plurality of emission colors includes a method in which a plurality of emission dopants exist in one emission layer, a plurality of emission layers, and each emission layer includes Examples include a method in which dopants having different emission wavelengths are present, and a method in which minute pixels that emit light at different wavelengths are formed in a matrix.
  • patterning may be performed by a metal mask ink jet printing method or the like during film formation, if necessary.
  • patterning only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire element layer may be patterned.
  • the light emitting material used for the light emitting layer is not particularly limited. For example, in the case of a knocklight in a liquid crystal display element, a known light emitting material is used so as to conform to a wavelength range corresponding to CF (color filter) characteristics. Medium power Any one can be selected and combined to whiten.
  • the white light-emitting organic EL element is used as various types of light-emitting light sources and lighting devices, as one type of lamp 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.
  • backlights for watches, signboard advertisements, traffic lights, light sources for optical storage media, light sources for electronic photocopiers, light sources for optical communication processors, light sources for optical sensors, and display devices are required. And a wide range of uses such as general household appliances.
  • the transparent support substrate with this ITO transparent electrode was ultrasonically washed with isopropyl alcohol. Boiled and dried with dry nitrogen gas, and UV ozone cleaning was performed for 5 minutes.
  • This transparent support substrate is fixed to the substrate holder of a commercially available vacuum evaporation system, while a-NPD, CBP, Ir-12, BCP, Alq are attached to five tantalum resistance-fired thermal boats.
  • 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 CBP and the boat containing Ir 12 are energized independently, and the deposition rate of CBP as the luminescent host and Ir-12 as the luminescent dopant becomes 100: 7.
  • the light-emitting layer was provided by vapor-depositing 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 0.1 to 0.2 nmZ. Pass through the heated boat containing Alq.
  • An electron transport layer having a film thickness of 40 nm was provided at a deposition rate of 0.1 to 0.2 nmZ seconds.
  • the light emitting dopant As shown in Table 1, the light emitting dopant The organic EL elements OLED1-2 to 1-20 were prepared in the same manner except that the light emitting host and hole blocking material were changed.
  • the obtained organic EL elements OLED1-1 to 120 were evaluated as follows.
  • the organic EL elements OLED1-1 to 20 are turned on at room temperature (approximately 23 to 25 ° C) and under a constant current condition of 2.5 mAZcm 2 , and the emission luminance (L) [cdZm 2 ] immediately after the start of lighting is calculated.
  • the external extraction quantum efficiency (r?) was calculated by measurement.
  • CS-1000 manufactured by Co-Kaminolta Sensing Co., Ltd.
  • the external extraction quantum efficiency is expressed as a relative value when the organic EL element OLED1-1 is set to 100.
  • the light emission lifetime is expressed as a relative value when the organic EL element OLED 1-1 is set to 100.
  • Table 1 shows the results obtained as described above.
  • the organic EL device produced using the ortho metal complex according to the present invention has higher luminous efficiency and longer lifetime than the comparative organic EL device. Clearly it can be achieved.
  • a carboline derivative or a derivative having a ring structure in which at least one carbon atom of the hydrocarbon ring constituting the carboline ring of the carboline derivative is further substituted with a nitrogen atom is used in the light emitting layer.
  • a carboline derivative or 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 further substituted with a nitrogen atom is used for the hole blocking layer.
  • the organic EL device OLED1-4 described in Example 1 was used as a blue light emitting device.
  • the scanning line 5 and the plurality of data lines 6 in the wiring part are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a grid pattern and are connected to the pixels 3 at orthogonal positions ( Details are not shown).
  • the plurality of pixels 3 are driven by an active matrix system provided with an organic EL element corresponding to each emission color, a switching transistor which is an active element, and a driving transistor, and a scanning signal is applied from a scanning line 5. Then, an image data signal is received from the data line 6 and light is emitted according to the received image data. In this way, a full-color display device was produced by appropriately juxtaposing the red, green, and blue pixels.
  • Example 2 In the production of the full-color display device described in Example 2, the full-color display device is the same as Example 2 except that the organic EL element OLED1-6 is used in place of the organic EL element OLED1-4 that is a blue light emitting element. Was made. It has been found that by driving the full-color display device, a clear full-color moving image display having high durability with high emission luminance and high brightness can be obtained. [0309] Example 4
  • Example 2 In the production of the full-color display device described in Example 2, a full-color display device was obtained in the same manner as in Example 2 except that the organic EL element OLED1-13 was used instead of the organic EL element OLED1-4, which is a blue light emitting element. Was made. It has been found that by driving the full-color display device, it is possible to obtain a clear full-color moving image display having high durability with high light emission luminance.
  • Example 2 In the production of the full-color display device described in Example 2, a full-color display device was obtained in the same manner as in Example 2 except that the organic EL element OLED1-14 was used instead of the organic EL element OLED1-4 that is a blue light emitting element. Was made. It has been found that by driving the full-color display device, it is possible to obtain a clear full-color moving image display having high durability with high light emission luminance.
  • the electrode of the transparent electrode substrate described in Example 1 was patterned to 20 mm ⁇ 20 mm, and then a-NPD was formed to a thickness of 25 nm as a hole injection / transport layer in the same manner as in Example 1,
  • the heated boat containing CBP, the boat containing Compound 20 of the present invention, and the boat containing Ir 9 were energized independently, and CBP as a light emitting host and Illustrative Compound 20 of the present invention as Ir and a light emitting dopant and Ir—
  • the deposition rate of 9 was adjusted to 100: 5: 0.6, deposition was performed to a thickness of 30 nm, and a light emitting layer was provided.
  • BCP was formed into an lOnm film to provide a hole blocking layer. Furthermore, Alq was deposited at 40nm.
  • An electron transport layer was provided.
  • Example 2 a square perforated mask having 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 150 nm was deposited.
  • FIG. 5 shows schematic diagrams of flat lamps.
  • Figure 5 shows a schematic diagram
  • Figure 6 shows a cross-sectional view. When this flat lamp was energized, almost white light was obtained, indicating that it can be used as a lighting device.
  • a white lighting device was produced in the same manner as in Example 6 except that the exemplified compound 20 of the present invention was changed to the exemplified compound 30 in the production of the white light emitting device of Example 6. When this flat lamp was energized, almost white light was obtained and it was found that it could be used as a lighting device.
  • a white lighting device was produced in the same manner as in Example 6 except that the exemplified compound 20 of the present invention was changed to the exemplified compound 39 in the production of the white light emitting device of Example 6. When this flat lamp was energized, almost white light was obtained and it was found that it could be used as a lighting device.
  • ITO indium stannate
  • the surface resistance of this anode was 10 ⁇ .
  • a mask patterned on this organic compound layer (light emission area is 5mm x 5mm)
  • 0.5 nm of lithium fluoride was deposited as a cathode buffer layer and 150 nm of aluminum was deposited as a cathode to provide a cathode.
  • a light-emitting device was fabricated by emitting aluminum lead wires from the anode and cathode, respectively. The device was placed in a glove box substituted with nitrogen gas, and sealed with a glass sealing container using an ultraviolet curable adhesive (XNR5493, manufactured by Nagase Ciba) to produce a flat lamp. When this flat lamp was energized, almost white light was obtained, which proved to be usable as a lighting device.
  • XNR5493 ultraviolet curable adhesive
  • Example Compound 6 of the present invention was changed to Example Compound 11 in the production of the white light emitting device of Example 9.
  • this flat lamp is energized, almost white light is obtained and it can be used as a lighting device.
  • Example Compound 6 of the present invention was changed to Example Compound 52 in the production of the white light-emitting device of Example 9.
  • this flat lamp is energized, almost white light is obtained and it can be used as a lighting device.
  • ITO indium stannate
  • the surface resistance of this anode was 10 ⁇ .
  • a notched mask (a mask with a light emitting area of 5 mm x 5 mm) was placed on this organic compound layer, and lithium fluoride 0.5 nm as the cathode buffer layer and aluminum 150 nm as the cathode in the vapor deposition system.
  • the cathode was provided by vapor deposition.
  • a light-emitting device was fabricated by emitting aluminum lead wires from the anode and cathode, respectively. The device was placed in a glove box substituted with nitrogen gas, and sealed with a glass sealing container using an ultraviolet curable adhesive (XNR5493, manufactured by Nagase Ciba) to produce a flat lamp. When this flat lamp was energized, almost white light was obtained, confirming that it could be used as a lighting device.
  • Example Compound 41 of the present invention was changed to Example Compound 39 in the production of the white light-emitting device of Example 12.
  • this flat lamp was energized, almost white light was obtained, indicating that it could be used as a lighting device.
  • a white lighting device was produced in the same manner as in Example 12 except that the hole transport control material ACZ1 was changed to ACZ2 in the production of the white light emitting device of Example 12. When this flat lamp was energized, almost white light was obtained, which proved to be usable as a lighting device.
  • the organic EL device OLED2— was similarly prepared except that the luminescent dopant was changed to Ir 1 and the hole blocking material was changed as shown in Table 2. 1-2-13 were produced. Measurement of the external extraction quantum efficiency and emission lifetime of each obtained organic EL device was carried out in the same manner as described in Example 1. At this time, the value of the organic EL element OLED2-1 was assumed to be 100, and the value of each organic EL element was expressed as a relative value. Table 2 shows the results obtained.

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Abstract

La présente invention concerne un matériau de dispositif électroluminescent organique caractérisé par un rendement d'éclairage élevé tout en offrant une longue durée d'émission. L'invention porte également sur un dispositif électroluminescent organique, qui utilise ledit matériau, et sur un dispositif d'éclairage et un écran utilisant tous deux le dispositif électroluminescent organique. Le matériau de dispositif électroluminescent organique se caractérise par le fait qu’il contient un complexe métallique ayant une structure partielle représentée par la formule générale (Z). [Formule chimique 1] (Z)
PCT/JP2006/304234 2005-03-29 2006-03-06 Materiau de dispositif electroluminescent organique, dispositif electroluminescent organique, ecran et dispositif d’eclairage WO2006103874A1 (fr)

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