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WO2012098996A1 - Élément électroluminescent organique, dispositif d'affichage, dispositif d'éclairage et matériau d'élément électroluminescent organique - Google Patents

Élément électroluminescent organique, dispositif d'affichage, dispositif d'éclairage et matériau d'élément électroluminescent organique Download PDF

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WO2012098996A1
WO2012098996A1 PCT/JP2012/050536 JP2012050536W WO2012098996A1 WO 2012098996 A1 WO2012098996 A1 WO 2012098996A1 JP 2012050536 W JP2012050536 W JP 2012050536W WO 2012098996 A1 WO2012098996 A1 WO 2012098996A1
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group
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WO2012098996A8 (fr
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近藤　麻衣子
片倉　利恵
押山　智寛
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Konica Minolta Inc
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    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to an organic electroluminescence element, a display device, a lighting device, and an organic electroluminescence element material.
  • An organic electroluminescence element (hereinafter also referred to as an organic EL element) has a structure in which a light emitting layer containing a light emitting compound is sandwiched between a cathode and an anode, and recombines them by injecting electrons and holes into the light emitting layer.
  • This is an element that generates excitons (excitons) and emits light by using light emission (fluorescence / phosphorescence) when the excitons are deactivated, and emits light at a voltage of several to several tens of volts. Because it is possible, it is attracting attention as a next-generation flat display and illumination.
  • Non-Patent Document 1 Since an organic EL device using phosphorescence emission from an excited triplet with an upper limit of internal quantum efficiency of 100% has been reported by Princeton University (for example, see Non-Patent Document 1), Research has become active (see, for example, Non-Patent Document 2 and Patent Document 1).
  • Non-Patent Document 3 iridium complex-based heavy metal complexes have been studied as materials that exhibit phosphorescence at room temperature (for example, see Non-Patent Document 3).
  • Non-patent Document 2 a tris (2-phenylpyridine) iridium complex is widely known (Non-patent Document 2), and a silyl group is added to the tris (2-phenylpyridine) skeleton for the purpose of improving the durability and luminous efficiency of the dopant.
  • An iridium complex having an introduced ligand is disclosed (for example, see Patent Document 2).
  • the phosphorescent material emitting blue light is difficult to shorten the emission wavelength, and has not achieved sufficient performance for practical use.
  • the emission wavelength of the light-emitting material is shortened to achieve blue, and a high-efficiency device can be achieved.
  • the light-emitting lifetime of the device is greatly deteriorated, so an improvement in the trade-off is required. This is the current situation.
  • An object of the present invention is to provide an organic electroluminescence element that exhibits high light emission efficiency, has a long light emission lifetime, has a low driving voltage, and emits shortwave light, a lighting device including the element, a display device, and a display device An organic electroluminescence element material used for formation is provided.
  • An organic electroluminescent device having at least one light emitting layer between an anode and a cathode, wherein a ligand represented by the following general formula (A) is present in a transition metal element of group 8 to group 10 in the periodic table
  • An organic electroluminescence device comprising a metal complex coordinated with at least one.
  • A represents a ring covalently bonded to the transition metal element, and represents a 6-membered aromatic hydrocarbon ring or a 5-membered or 6-membered aromatic heterocycle
  • B represents a carbon atom or nitrogen. It represents a 5-membered aromatic heterocyclic ring coordinated to the transition metal element by an atom
  • the ligand represented by the general formula (A) has at least one group represented by the following general formula (1).
  • L represents a bivalent coupling group.
  • n 0 or an integer of 1 to 3, and when n is 2 or more, a plurality of L may be the same or different. L may have a substituent.
  • Y1, Y2 and Y3 each represent a hydrogen atom or a substituent. However, at least one of Y1, Y2, and Y3 represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group. * Represents a connection site with a ring represented by A and covalently bonded to the transition metal element. ] 2.
  • X and Y each represent a carbon atom or a nitrogen atom.
  • a ′ represents an atomic group necessary for forming a 6-membered aromatic hydrocarbon ring or a 5-membered or 6-membered aromatic heterocycle together with X—C.
  • R represents a hydrogen atom or a substituent.
  • n1 represents an integer of 1 to 4, and when n1 is 2 or more, R may be the same or different substituents.
  • Z represents a hydrogen atom or a substituent. At least one of R, R ′ 1 , R ′ 2 and Z represents a group represented by the general formula (1).
  • X 1 -L 1 -X 2 represents a bidentate ligand, and X 1 and X 2 each independently represent a carbon atom, a nitrogen atom or an oxygen atom.
  • L 1 represents an atomic group that forms a bidentate ligand together with X 1 and X 2 .
  • m1 represents an integer of 1, 2 or 3
  • m2 represents an integer of 0, 1 or 2
  • m1 + m2 is 2 or 3.
  • M represents a transition metal element of Group 8 to Group 10 in the periodic table. ] 4). 4.
  • the organic electroluminescence device according to any one of 1 to 3, wherein the metal complex is represented by the following general formula (3).
  • Z1 represents an atomic group necessary for forming a 6-membered aromatic hydrocarbon ring or a 5-membered or 6-membered aromatic heterocycle with C—C.
  • R represents a hydrogen atom or a substituent.
  • n1 is an integer of 1 to 4. When n1 is 2 or more, R may be the same or different substituents.
  • R ′ represents a hydrogen atom or a substituent, and n2 is an integer of 1 or 2. When n2 is 2, R ′ may be the same or different substituents.
  • Z represents a hydrogen atom or a substituent. At least one of R, R ′ and Z represents a group represented by the general formula (1).
  • X 1 -L 1 -X 2 represents a bidentate ligand, and X 1 and X 2 each independently represent a carbon atom, a nitrogen atom or an oxygen atom.
  • L 1 represents an atomic group that forms a bidentate ligand together with X 1 and X 2 .
  • m1 represents an integer of 1, 2 or 3
  • m2 represents an integer of 0, 1 or 2
  • m1 + m2 is 2 or 3.
  • M represents a transition metal element of Group 8 to Group 10 in the periodic table. ] 5.
  • the organic electroluminescence device according to any one of 1 to 4, wherein the metal complex is represented by the following general formula (4).
  • R 2 , R 3 , R 4 , R 5 , Z, R ′ 1 and R ′ 2 each represent a hydrogen atom or a substituent. At least one of R 2 to R 5 , R ′ 1 , R ′ 2 and Z represents a group represented by the general formula (1).
  • X 1 -L 1 -X 2 represents a bidentate ligand, and X 1 and X 2 each independently represent a carbon atom, a nitrogen atom or an oxygen atom.
  • L 1 represents an atomic group that forms a bidentate ligand together with X 1 and X 2 .
  • m1 represents an integer of 1, 2 or 3
  • m2 represents an integer of 0, 1 or 2
  • m1 + m2 is 2 or 3.
  • M represents a transition metal element of Group 8 to Group 10 in the periodic table.
  • 6 The organic electroluminescence device according to any one of 1 to 5, wherein the metal complex is represented by the following general formula (5).
  • Z 2 represents an atomic group necessary for forming a 6-membered aromatic hydrocarbon ring or a 5-membered or 6-membered aromatic heterocyclic ring.
  • Ra represents a substituent.
  • R 2 , R 3 , R 4 , R 5 , R ′ 1 and R ′ 2 each represent a hydrogen atom or a substituent.
  • At least one of R 2 to R 5 , R ′ 1 and R ′ 2 represents a group represented by the general formula (1).
  • X 1 -L 1 -X 2 represents a bidentate ligand, and X 1 and X 2 each independently represent a carbon atom, a nitrogen atom or an oxygen atom.
  • L 1 represents an atomic group that forms a bidentate ligand together with X 1 and X 2 .
  • m1 represents an integer of 1, 2 or 3
  • m2 represents an integer of 0, 1 or 2
  • m1 + m2 is 2 or 3.
  • M represents a transition metal element of Group 8 to Group 10 in the periodic table. ] 7.
  • Rb, Rc, Rd, R 2 , R 3 , R 4 , R 5 , R ′ 1 and R ′ 2 each represent a hydrogen atom or a substituent.
  • At least one of R 2 to R 5 , R ′ 1 and R ′ 2 represents a group represented by the general formula (1).
  • X 1 -L 1 -X 2 represents a bidentate ligand, and X 1 and X 2 each independently represent a carbon atom, a nitrogen atom or an oxygen atom.
  • L 1 represents an atomic group that forms a bidentate ligand together with X 1 and X 2 .
  • n1 represents an integer of 1, 2 or 3
  • m2 represents an integer of 0, 1 or 2
  • m1 + m2 is 2 or 3.
  • M represents a transition metal element of Group 8 to Group 10 in the periodic table. ] 8).
  • X represents a carbon atom or a nitrogen atom.
  • a ′ represents an atomic group necessary for forming a 6-membered aromatic hydrocarbon ring or a 5-membered or 6-membered aromatic heterocycle with X—C.
  • R represents a hydrogen atom or a substituent.
  • n1 is an integer of 1 to 4. When n1 is 2 or more, R may be the same or different substituents.
  • Z represents a hydrogen atom or a substituent. At least one of R, R ′ 1 , R ′ 2 and Z represents a group represented by the general formula (1).
  • X 1 -L 1 -X 2 represents a bidentate ligand, and X 1 and X 2 each independently represent a carbon atom, a nitrogen atom or an oxygen atom.
  • L 1 represents an atomic group that forms a bidentate ligand together with X 1 and X 2 .
  • m1 represents an integer of 1, 2 or 3
  • m2 represents an integer of 0, 1 or 2
  • m1 + m2 is 2 or 3.
  • M represents a transition metal element of Group 8 to Group 10 in the periodic table.
  • the organic electroluminescence device according to any one of 1, 2, and 8, wherein the metal complex is represented by the following general formula (8).
  • X represents a carbon atom or a nitrogen atom.
  • a ′ represents an atomic group necessary for forming a 6-membered aromatic hydrocarbon ring or a 5-membered or 6-membered aromatic heterocycle with X—C.
  • R represents a hydrogen atom or a substituent.
  • n1 is an integer of 1 to 4. When n1 is 2 or more, R may be the same or different substituents.
  • Z represents a hydrogen atom or a substituent.
  • R ′ 1 and R ′ 2 each represent a hydrogen atom or a substituent. At least one of R, R ′ 1 , R ′ 2 and Z represents a group represented by the general formula (1).
  • X 1 -L 1 -X 2 represents a bidentate ligand, and X 1 and X 2 each independently represent a carbon atom, a nitrogen atom or an oxygen atom.
  • L 1 represents an atomic group that forms a bidentate ligand together with X 1 and X 2 .
  • m1 represents an integer of 1, 2 or 3
  • m2 represents an integer of 0, 1 or 2
  • m1 + m2 is 2 or 3.
  • M represents a transition metal element of Group 8 to Group 10 in the periodic table. ] 10. 10.
  • the organic electroluminescence device according to any one of 1, 2, 8, and 9, wherein the metal complex is represented by the following formula (9).
  • R 2 , R 3 , R 4 , R 5 , Z, R ′ 1 and R ′ 2 represent a hydrogen atom or a substituent. At least one of R 2 to R 5 , R ′ 1 , R ′ 2 and Z represents a group represented by the general formula (1).
  • X 1 -L 1 -X 2 represents a bidentate ligand, and X 1 and X 2 each independently represent a carbon atom, a nitrogen atom or an oxygen atom.
  • L 1 represents an atomic group that forms a bidentate ligand together with X 1 and X 2 .
  • m1 represents an integer of 1, 2 or 3
  • m2 represents an integer of 0, 1 or 2
  • m1 + m2 is 2 or 3.
  • M represents a transition metal element of Group 8 to Group 10 in the periodic table.
  • R 4 in any one of the general formula (4) described in 5 above, the general formula (5) described in 6 above, the general formula (6) described in 7 above, and the general formula (9) described in 10 above is 11.
  • a display device comprising the organic electroluminescence element as described in any one of 1 to 18 above.
  • An illuminating device comprising the organic electroluminescence element as described in any one of 1 to 18 above.
  • An organic electroluminescent device material comprising the metal complex described in any one of 1 to 16 above.
  • an organic electroluminescence element that exhibits high light emission efficiency, has a long light emission lifetime, has a low driving voltage, and exhibits short-wave light emission, an illumination device including the organic electroluminescence element, a display device, and the element
  • An organic electroluminescence element material used for formation can be provided.
  • the organic EL device of the present invention has the configuration described in any one of claims 1 to 17, so that the efficiency is high, the half-life is long, the driving voltage is low, and the light emission of the device is short.
  • An organic electroluminescence device having a wavelength could be provided.
  • a display device and a lighting device including the organic electroluminescence element could be provided.
  • the organic EL element material useful for the organic EL element formation of this invention was able to be developed.
  • the present inventors have obtained an element life and high luminous efficiency that can withstand practical use because aggregation of metal complexes occurs in the constituent layers of the organic EL element. We presumed that there was not, and examined the problem seriously.
  • the ligand has at least one ligand represented by the above general formula (A) described in 1 above, and the ligand is coordinated to a transition metal element of Groups 8 to 10 in the periodic table. It was found that the lifetime of the device was improved and the luminous efficiency was increased by introducing the group represented by the general formula (1) into the ligand in the metal complex.
  • the aggregation of metal complexes in the constituent layers of the organic EL element can be suppressed, and the TT annihilation occurring between the exciton triplets of the metal complex can be suppressed, so that the lifetime of the element can be improved.
  • the present inventors have examined that the luminance and lifetime of the device are improved by reducing the reorientation energy of the metal complex.
  • a substituent is introduced into an aromatic ring such as a benzene ring to reduce the degree of freedom of the dihedral angle of the molecular structure, or a bulky alkylene chain is introduced into the molecule. It is known to fix as much as possible so that it cannot move freely.
  • the ligand is constituted by introducing a bulky substituent represented by the general formula (1) into the ligand represented by the general formula (A) described in 1 above. It is possible to suppress the rotation and vibration of the aromatic ring, and further to suppress the degree of freedom between the ligands by introducing the above-described substituents, whereby the metal complex represented by the general formula (1) It was possible to suppress the re-orientation energy of.
  • the ligand represented by the general formula (A) described in 1 above is substituted with an aromatic hydrocarbon ring group (aromatic hydrocarbon) represented by the general formula (1).
  • the emission wavelength of the device can be shortened by introducing the group represented by the general formula (1) into the ligand represented by the general formula (A) described in 1. I was able to find out that it was possible.
  • Organic EL element material >> The organic EL element material of the present invention will be described.
  • the organic EL device material of the present invention is a novel metal complex. Specifically, as described in 1 above, the material has at least one ligand represented by the general formula (A). This is a metal complex in which a ligand is coordinated to a transition metal element of Group 8 to Group 10 in the periodic table.
  • the metal complex according to the organic EL element material of the present invention can be used in any one of the constituent layers of the organic EL element of the present invention, but the effect of the present invention (the luminous efficiency of the element (specifically, the external extraction quantum From the standpoint of sufficiently improving efficiency, simply referred to as efficiency), increasing half-life, and lowering driving voltage), a light-emitting dopant (also simply referred to as a dopant) in the light-emitting layer of the device and further in the light-emitting layer. It is preferable to use as.
  • examples of the 6-membered aromatic hydrocarbon ring represented by A and bonded to the transition metal element by a covalent bond include a benzene ring.
  • the benzene ring may further have substituents represented by Y1, Y2, and Y3 in the general formula (1) described later.
  • examples of the 5-membered or 6-membered aromatic heterocycle represented by A and bonded to the transition metal element by a covalent bond include an oxazole ring, a thiophene ring, a furan ring, and a pyrrole ring.
  • said ring may have further the substituent represented by Y1, Y2, Y3 in General formula (1) mentioned later, respectively.
  • examples of the 5-membered aromatic heterocycle coordinated to the transition metal element by a carbon atom or a nitrogen atom represented by B include an oxazole ring, an oxadiazole ring, Examples include an oxatriazole ring, an isoxazole ring, a tetrazole ring, a thiadiazole ring, a thiatriazole ring, an isothiazole ring, a thiophene ring, a furan ring, a pyrrole ring, an imidazole ring, a pyrazole ring, and a triazole ring.
  • these rings may further have substituents represented by Y1, Y2, and Y3 in General Formula (1), which will be described later.
  • the substituents of A and B may be bonded to each other to form a ring.
  • the ligand represented by the general formula (A) has at least one group represented by the general formula (1).
  • L represents —C (Rx) (Ry) —, —O—, —S—, a divalent linking group derived from an aromatic hydrocarbon ring or an aromatic heterocyclic ring, or these Represents a combination of * Represents a connecting site with the ring represented by A and covalently bonded to the transition metal element.
  • Rx and Ry each represent a hydrogen atom or a substituent, and the substituent is synonymous with the substituent represented by Y1, Y2, and Y3 in the general formula (1).
  • each of the substituents represented by Y1, Y2, and Y3 is an alkyl group (for example, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, hexyl group).
  • substituents may be further substituted with the above substituents.
  • a plurality of these substituents may be bonded to each other to form a ring.
  • alkyl groups, cycloalkyl groups, aromatic hydrocarbon ring groups, aromatic heterocyclic groups, heterocyclic groups, alkoxy groups, aryloxy groups, alkoxycarbonyl groups, acyl groups, amino groups, halogen atoms, cyano groups, silyl groups Group is preferable, and these substituents may further have a substituent.
  • At least one of Y1, Y2, and Y3 represents an aromatic hydrocarbon ring group or an aromatic heterocyclic group
  • the aromatic hydrocarbon ring group in the general formula (1) Y1, Y2, and Y3 each have the same meaning as the aromatic hydrocarbon ring group described in the substituent
  • the aromatic heterocyclic group is represented by Y1, Y2, and Y3 in the general formula (1), It is synonymous with the aromatic-hydrocarbon cyclic group as described in the substituent represented respectively.
  • transition metal elements belonging to Group 8 to Group 10 in the periodic table used for forming the metal complex relating to the organic EL device material of the present invention include Fe, Co, Ni, Ru, Rh, Pd, Os, Ir, Pt, and the like. Rh, Ir, and Pt are preferable, and Ir is preferably used among them.
  • Preferred embodiments of the metal complex according to the organic EL device material of the present invention include the metal complexes described in any one of the general formulas (2) to (9) described above.
  • the 6-membered aromatic hydrocarbon ring formed by A ′ together with X—C is synonymous with the benzene ring represented by A in the general formula (A).
  • the 5- or 6-membered aromatic heterocycle formed by A ′ together with X—C is the 5-membered or 6-membered aromatic ring represented by A in the general formula (A). Synonymous with heterocyclic ring.
  • the substituents represented by R, R ′ 1 , R ′ 2 , and Z are the substituents represented by Y1, Y2, and Y3 in the general formula (1), respectively. It is synonymous.
  • examples of the bidentate ligand represented by X 1 -L 1 -X 2 include phenylpyridine, phenylpyrazole, phenylimidazole, phenyltriazole, phenyltetrazole, pyrazabol, acetylacetone, and picoline. An acid etc. are mentioned. These ligands may further have the above substituent.
  • transition metal elements of groups 8 to 10 in the periodic table of elements represented by M are synonymous with the transition metal elements of groups 8 to 10 in the periodic table of elements in general formula (A). is there.
  • the 6-membered aromatic hydrocarbon ring formed by Z1 together with C—C is synonymous with the benzene ring represented by A in the general formula (A).
  • the 5-membered or 6-membered aromatic heterocycle formed by Z1 together with C—C is the same as the 5-membered or 6-membered aromatic heterocycle represented by A in the general formula (A). It is synonymous.
  • bidentate ligands represented by X 1 -L 1 -X 2 are the compounds of formula (2), coordination of bidentate represented by X 1 -L 1 -X 2 Synonymous with rank.
  • transition metal elements of groups 8 to 10 in the periodic table of elements represented by M are synonymous with the transition metal elements of groups 8 to 10 in the periodic table of elements in general formula (A). is there.
  • bidentate ligands represented by X 1 -L 1 -X 2 are the compounds of formula (2), coordination of bidentate represented by X 1 -L 1 -X 2 Synonymous with rank.
  • transition metal elements of groups 8 to 10 in the periodic table of elements represented by M are synonymous with the transition metal elements of groups 8 to 10 in the periodic table of elements in the general formula (A). is there.
  • the 6-membered aromatic hydrocarbon ring represented by Z2 has the same meaning as the benzene ring represented by A in the general formula (A).
  • the 5-membered or 6-membered aromatic heterocycle represented by Z2 has the same meaning as the 5-membered or 6-membered aromatic heterocycle represented by A in the general formula (A). .
  • each of the substituents represented by Ra, R 2 , R 3 , R 4 , R 5 , R ′ 1 , R ′ 2 is Y1, Y2, Y3 in General Formula (1). And each has the same meaning as the substituent represented.
  • bidentate ligands represented by X 1 -L 1 -X 2 are the compounds of formula (2), coordination of bidentate represented by X 1 -L 1 -X 2 Synonymous with rank.
  • transition metal elements of groups 8 to 10 in the periodic table of elements represented by M are synonymous with the transition metal elements of groups 8 to 10 in the periodic table of elements in general formula (A). is there.
  • the substituents represented by Rb and Rc have the same meanings as the substituents represented by Y1, Y2, and Y3 in general formula (1), respectively. Especially, it is preferable that at least one of the substituents of Rb and Rc is an alkyl group having 2 or more carbon atoms.
  • At least one of the substituents for Rd is preferably a 5-membered or 6-membered aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group, or a non-aromatic heterocyclic group, and more preferably.
  • n 1 to 3.
  • bidentate ligands represented by X 1 -L 1 -X 2 are the compounds of formula (2), coordination of bidentate represented by X 1 -L 1 -X 2 Synonymous with rank.
  • transition metal elements of groups 8 to 10 in the periodic table of elements represented by M are synonymous with the transition metal elements of groups 8 to 10 in the periodic table of elements in general formula (A). is there.
  • the 6-membered aromatic hydrocarbon ring that A ′ forms with X—C is synonymous with the benzene ring represented by A in the general formula (A).
  • the 5-membered or 6-membered aromatic heterocycle formed by A ′ together with X—C in the general formula (7) is the 5-membered or 6-membered aromatic heterocycle represented by A in the general formula (A). It is synonymous with.
  • bidentate ligands represented by X 1 -L 1 -X 2 are the compounds of formula (2), coordination of bidentate represented by X 1 -L 1 -X 2 Synonymous with rank.
  • transition metal elements of groups 8 to 10 in the periodic table of elements represented by M are synonymous with the transition metal elements of groups 8 to 10 in the periodic table of elements in general formula (A). is there.
  • the 6-membered aromatic hydrocarbon ring that A ′ forms with X—C is synonymous with the benzene ring represented by A in the general formula (A).
  • the 5-membered or 6-membered aromatic heterocycle formed by A ′ together with X—C is the 5-membered or 6-membered aromatic heterocycle represented by A in the general formula (A). It is synonymous with.
  • bidentate ligands represented by X 1 -L 1 -X 2 are the compounds of formula (2), coordination of bidentate represented by X 1 -L 1 -X 2 Synonymous with rank.
  • transition metal elements of groups 8 to 10 in the periodic table of elements represented by M are synonymous with the transition metal elements of groups 8 to 10 in the periodic table of elements in general formula (A). is there.
  • R 2 , R 3 , R 4 , R 5 , Z, R ′ 1 and R ′ 2 are represented by Y1, Y2 and Y3 in the general formula (1), respectively. These are synonymous with the substituents represented respectively.
  • bidentate ligands represented by X 1 -L 1 -X 2 are the compounds of formula (2), coordination of bidentate represented by X 1 -L 1 -X 2 Synonymous with rank.
  • transition metal elements of groups 8 to 10 in the periodic table of elements represented by M are synonymous with the transition metal elements of groups 8 to 10 in the periodic table of elements in general formula (A). is there.
  • the organic EL device material of the present invention has at least one ligand represented by the general formula (A), and the ligand is a transition metal element of Group 8 to Group 10 in the periodic table.
  • the coordinated metal complex and the metal complex represented by any one of the general formulas (2) to (9) are shown below, but the present invention is not limited thereto.
  • the organic EL element material of the present invention has at least one ligand represented by the general formula (A), and the ligand is a transition metal element of Group 8 to Group 10 in the periodic table. Examples of synthesizing the metal complex coordinated and the metal complex represented by any one of the general formulas (2) to (9) will be described in detail in Examples described later.
  • a non-light emitting intermediate layer may be provided between the light emitting layers.
  • the intermediate layer may be a charge generation layer or a multi-photon unit configuration.
  • the organic EL element of the present invention is preferably a white light emitting layer, and is preferably a lighting device using these.
  • the light emitting layer according to the present invention is a layer that emits light by recombination of electrons and holes injected from the electrode, the electron transport layer, or the hole transport layer, and the light emitting portion is in the layer of the light emitting layer. May be the interface between the light emitting layer and the adjacent layer.
  • the total film thickness of the light emitting layer is not particularly limited, but from the viewpoint of improving the uniformity of the film, preventing unnecessary application of high voltage during light emission, and improving the stability of the emission color with respect to the drive current. It is preferable to adjust in the range of 2 nm to 5 ⁇ m, more preferably in the range of 2 to 200 nm, and particularly preferably in the range of 5 to 100 nm.
  • a light emitting dopant or host compound described later is used, for example, a vacuum deposition method, a wet method (also referred to as a wet process, for example, a spin coating method, a casting method, a die coating method, a blade coating method, a roll coating method, Examples thereof include an inkjet method, a printing method, a spray coating method, a curtain coating method, an LB method (Langmuir Brodgett method) and the like.
  • a wet process also referred to as a wet process, for example, a spin coating method, a casting method, a die coating method, a blade coating method, a roll coating method
  • examples thereof include an inkjet method, a printing method, a spray coating method, a curtain coating method, an LB method (Langmuir Brodgett method) and the like.
  • the light emitting layer of the organic EL device of the present invention contains a light emitting dopant (phosphorescent dopant (also referred to as phosphorescent dopant, phosphorescent dopant group) or fluorescent dopant) compound and a light emitting host compound. Is preferred.
  • a light emitting dopant phosphorescent dopant (also referred to as phosphorescent dopant, phosphorescent dopant group) or fluorescent dopant) compound and a light emitting host compound. Is preferred.
  • Luminescent dopant compound A light-emitting dopant compound (a light-emitting dopant, also simply referred to as a dopant) will be described.
  • Fluorescent dopants also referred to as fluorescent compounds
  • phosphorescent dopants also referred to as phosphorescent emitters, phosphorescent compounds, phosphorescent compounds, etc.
  • the luminescent dopant can be used as the luminescent dopant.
  • Phosphorescent dopant also called phosphorescent dopant
  • the phosphorescent dopant according to the present invention will be described.
  • the phosphorescent dopant compound according to the present invention is a compound in which light emission from an excited triplet is observed, specifically, a compound that emits phosphorescence at room temperature (25 ° C.), and has a phosphorescence quantum yield of 25. Although it is defined as a compound of 0.01 or more at ° C., a preferable phosphorescence quantum yield is 0.1 or more.
  • the phosphorescent quantum yield can be measured by the method described in Spectroscopic II, page 398 (1992 edition, Maruzen) of the Fourth Edition Experimental Chemistry Course 7. Although the phosphorescence quantum yield in a solution can be measured using various solvents, the phosphorescence dopant according to the present invention achieves the phosphorescence quantum yield (0.01 or more) in any solvent. That's fine.
  • the phosphorescent dopant There are two types of light emission of the phosphorescent dopant in principle. One is the recombination of carriers on the host compound to which carriers are transported to generate an excited state of the luminescent host compound, and this energy is used as the phosphorescent dopant.
  • the excited state energy of the phosphorescent dopant is required to be lower than the excited state energy of the host compound.
  • At least one of the light-emitting layers contains a phosphorescent organometallic complex (also referred to as a phosphorescent dopant or a phosphorescent dopant).
  • a phosphorescent organometallic complex also referred to as a phosphorescent dopant or a phosphorescent dopant.
  • fluorescent dopant also called fluorescent compound
  • fluorescent dopants include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes, pyrylium dyes, perylene dyes, stilbene dyes , Polythiophene dyes, rare earth complex phosphors, and the like, and compounds having a high fluorescence quantum yield represented by laser dyes.
  • the light-emitting dopant according to the present invention may be used in combination of a plurality of types of compounds, a combination of phosphorescent dopants having different structures, or a combination of a phosphorescent dopant and a fluorescent dopant.
  • the host compound has a mass ratio in the layer of 20% or more, and the phosphorescence quantum yield of phosphorescence emission is 0 at room temperature (25 ° C.). Defined as less than 1 compound.
  • the phosphorescence quantum yield is preferably less than 0.01.
  • the mass ratio in the layer is 20% or more among the compounds contained in a light emitting layer.
  • the light-emitting host that can be used in the present invention is not particularly limited, and compounds conventionally used in organic EL devices can be used.
  • a compound that has a hole transporting ability and an electron transporting ability, prevents the emission of light from being increased in wavelength, and has a high Tg (glass transition temperature) is preferable.
  • a conventionally known light emitting host may be used alone, or a plurality of types may be used in combination.
  • the metal complex of the present invention by using a plurality of kinds of the metal complex of the present invention and / or a conventionally known compound used as the phosphorescent dopant, it becomes possible to mix different light emission, thereby obtaining any light emission color.
  • the light emitting host used in 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 (polymerizable light emitting host).
  • a polymerizable group such as a vinyl group or an epoxy group (polymerizable light emitting host).
  • one or a plurality of such compounds may be used.
  • examples of the light emitting host of the light emitting layer of the organic EL device of the present invention include compounds represented by the following general formula (B) or the following general formula (B ′).
  • Xa represents O or S
  • Xb, Xc, and Xd each represents a hydrogen atom, a substituent, or a group represented by the following general formula (C)
  • at least one of Xb, Xc, and Xd Represents the following general formula (C)
  • Ar represents a carbazolyl group.
  • L2 represents a divalent linking group derived from an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
  • n represents 0 or an integer of 1 to 3, and when n is 2 or more, the plurality of L2s may be the same or different.
  • * represents a linking site with the general formula (B).
  • Ar represents a group represented by the following general formula (D).
  • Ar in the general formula (C) represents a carbazolyl group which may have a substituent, more preferably Xb is represented in the general formula (C) and Ar in the general formula (C) is It represents a carbazolyl group linked to L2 at the N-position which may have a substituent.
  • Xc is preferably represented by the general formula (C), and Xd is preferably a hydrogen atom.
  • Xa represents O or S
  • Xb and Xc each represents a hydrogen atom, a substituent or a group represented by the general formula (C) of the general formula (B), and at least one of Xb and Xc Represents the following general formula (C)
  • Ar represents a carbazolyl group in at least one of the groups represented by the general formula (C).
  • Xb and Xc are represented by the general formula (C), and more preferably, Ar in the general formula (C) is a substituent.
  • the electron transport layer is made of a material having a function of transporting electrons, and in a broad sense, an electron injection layer and a hole blocking layer are also included in the electron transport layer.
  • the electron transport layer can be provided with a single layer or a plurality of layers.
  • the electron transport layer only needs to have a function of transmitting electrons injected from the cathode to the light emitting layer.
  • any conventionally known compound may be selected and used in combination. Is possible.
  • electron transport materials examples include heterocyclic tetracarboxylic acid anhydrides such as nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, naphthalene perylene, A carbodiimide, a fluorenylidenemethane derivative, an anthraquinodimethane and anthrone derivative, an oxadiazole derivative, a carboline derivative, or at least one carbon atom of a hydrocarbon ring constituting the carboline ring of the carboline derivative is substituted with a nitrogen atom.
  • derivatives having a cyclic structure, hexaazatriphenylene derivatives and the like examples include heterocyclic tetracarboxylic acid anhydrides such as nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, naphthalene perylene, A carbodiimide,
  • a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron-withdrawing group can also be used as an electron transport material.
  • metal complexes of 8-quinolinol derivatives such as tris (8-quinolinol) aluminum (Alq), tris (5,7-dichloro-8-quinolinol) aluminum, tris (5,7-dibromo-8-quinolinol) aluminum Tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), and the like, and the central metals of these metal complexes are In, Mg, Metal complexes replaced with Cu, Ca, Sn, Ga, or Pb can also be used as the electron transport material.
  • metal-free or metal phthalocyanine or those in which the terminal is substituted with an alkyl group or a sulfonic acid group can also be used as the electron transport material.
  • inorganic semiconductors such as n-type-Si and n-type-SiC can also be used as the electron transport material.
  • the electron transport layer is made of an electron transport material such as a vacuum deposition method, a wet method (also referred to as a wet process, such as a spin coating method, a casting method, a die coating method, a blade coating method, a roll coating method, an ink jet method, a printing method, or a spraying method.
  • the film is preferably formed by thinning by a coating method, curtain coating method, LB method (Langmuir Brodgett method, etc.).
  • the thickness of the electron transport layer is not particularly limited, but is usually about 5 to 5000 nm, preferably 5 to 200 nm.
  • the electron transport layer may have a single layer structure composed of one or more of the above materials.
  • an n-type dopant such as a metal compound such as a metal complex or a metal halide may be doped.
  • 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 as an electrode material is used.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like.
  • a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this for example, a magnesium / silver mixture, Magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al 2 O 3 ) mixtures, lithium / aluminum mixtures, aluminum and the like are preferred.
  • 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 the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably 50 to 200 nm.
  • the emission luminance is advantageously improved.
  • a transparent or semi-transparent cathode can be produced by producing a conductive transparent material mentioned in the explanation of the anode described later on the cathode after producing the metal with a thickness of 1 to 20 nm on the cathode.
  • a transparent or semi-transparent cathode can be produced by producing a conductive transparent material mentioned in the explanation of the anode described later on the cathode after producing the metal with a thickness of 1 to 20 nm on the cathode.
  • Injection layer electron injection layer (cathode buffer layer), hole injection layer >> The injection layer is provided as necessary, and there are an electron injection layer and a hole injection layer, and as described above, it exists between the anode and the light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer. May be.
  • An injection layer is a layer provided between an electrode and an organic layer in order to reduce drive voltage and improve light emission luminance.
  • Organic EL element and its forefront of industrialization (issued by NTT Corporation on November 30, 1998) ) ”, Chapter 2,“ Electrode Materials ”(pages 123 to 166), which has a hole injection layer (anode buffer layer) and an electron injection layer (cathode buffer layer).
  • anode buffer layer hole injection layer
  • copper phthalocyanine is used.
  • an orthometalated complex layer represented by tris (2-phenylpyridine) iridium complex and the like.
  • azatriphenylene derivatives such as those described in JP-T-2003-519432 and JP-A-2006-135145 can also be used as hole injection materials.
  • cathode buffer layer (electron injection layer) The details of the cathode buffer layer (electron injection layer) are described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like. Specifically, strontium, aluminum, etc.
  • Metal buffer layer typified by, alkali metal compound buffer layer typified by lithium fluoride and potassium fluoride, alkaline earth metal compound buffer layer typified by magnesium fluoride and cesium fluoride, typified by aluminum oxide Examples thereof include an oxide buffer layer.
  • the buffer layer (injection layer) is preferably a very thin film, and the film thickness is preferably in the range of 0.1 nm to 5 ⁇ m, although it depends on the material.
  • ⁇ Blocking layer hole blocking layer, electron blocking layer>
  • the blocking layer is provided as necessary in addition to the basic constituent layer of the organic compound thin film as described above. For example, it is described in JP-A Nos. 11-204258 and 11-204359, and “Organic EL elements and the forefront of industrialization (published by NTT Corporation on November 30, 1998)” on page 237. There is a hole blocking (hole blocking) layer.
  • the hole blocking layer has a function of an electron transport layer in a broad sense, and is made of a hole blocking material that has a function of transporting electrons and has a remarkably small ability to transport holes. The probability of recombination of electrons and holes can be improved by blocking.
  • the structure of the electron transport layer described above can be used as a hole blocking layer according to the present invention, if necessary.
  • the hole blocking layer of the organic EL device of the present invention is preferably provided adjacent to the light emitting layer.
  • the hole blocking layer includes a carbazole derivative, a carboline derivative, a diazacarbazole derivative (the diazacarbazole derivative is a nitrogen atom in which any one of carbon atoms constituting the carboline ring is mentioned as the host compound described above. It is preferable to contain (represented by).
  • the light emitting layer having the shortest wavelength of light emission is preferably closest to the anode among all the light emitting layers.
  • 50% by mass or more of the compound contained in the hole blocking layer provided at the position has an ionization potential of 0.3 eV or more larger than the host compound of the shortest wave emitting layer.
  • the ionization potential is defined by the energy required to emit electrons at the HOMO (highest occupied orbital) level of the compound to the vacuum level, and can be determined by the following method, for example.
  • Gaussian 98 Gaussian 98, Revision A.11.4, MJ Frisch, et al, Gaussian, Inc., Pittsburgh PA, 2002.
  • a molecular orbital calculation software manufactured by Gaussian, USA As a value (eV unit converted value) calculated by performing structure optimization using B3LYP / 6-31G *. This calculation value is effective because the correlation between the calculation value obtained by this method and the experimental value is high.
  • the ionization potential can also be obtained by a method of directly measuring by photoelectron spectroscopy.
  • a low energy electron spectrometer “Model AC-1” manufactured by Riken Keiki Co., Ltd. or a method known as ultraviolet photoelectron spectroscopy can be suitably used.
  • the electron blocking layer has a function of a hole transport layer in a broad sense, and is made of a material that has a function of transporting holes and has an extremely small ability to transport electrons, and transports electrons while transporting holes. By blocking, the recombination probability of electrons and holes can be improved.
  • the structure of the hole transport layer described later can be used as an electron blocking layer as necessary.
  • the film thickness of the hole blocking layer and the electron transporting layer according to the present invention is preferably 3 to 100 nm, more preferably 5 to 30 nm.
  • the hole transport layer is made of a hole transport 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.
  • the hole transport material has any of hole injection or transport and electron barrier properties, 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, hydrazone derivatives
  • Examples thereof include stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
  • the above-mentioned materials can be used as the hole transport material, but it is preferable to use a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound.
  • aromatic tertiary amine compounds and styrylamine compounds include N, N, N ′, N′-tetraphenyl-4,4′-diaminophenyl; N, N′-diphenyl-N, N′— Bis (3-methylphenyl)-[1,1′-biphenyl] -4,4′-diamine (TPD); 2,2-bis (4-di-p-tolylaminophenyl) propane; 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane; N, N, N ′, N′-tetra-p-tolyl-4,4′-diaminobiphenyl; 1,1-bis (4-di-p-tolyl) Aminophenyl) -4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-di-p-tolylaminoph
  • No. 5,061,569 Having a condensed aromatic ring of, for example, 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPD), JP-A-4-308 4,4 ′, 4 ′′ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine in which three triphenylamine units described in Japanese Patent No. 88 are linked in a starburst type ( MTDATA) and the like.
  • NPD 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl
  • JP-A-4-308 4,4 ′, 4 ′′ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine in which three triphenylamine units described in Japanese Patent No. 88 are linked in a starburst type ( MTDATA) and the
  • a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
  • inorganic compounds such as p-type-Si and p-type-SiC can be used as the hole injection material and the hole transport material.
  • azatriphenylene derivatives such as those described in JP-T-2003-519432 and JP-A-2006-135145 can also be used as hole transport materials.
  • Japanese Patent Application Laid-Open No. 11-251067, J. Org. Huang et. al. A so-called p-type hole transport material as described in a book (Applied Physics Letters 80 (2002), p. 139) can also be used.
  • the hole transport layer can be formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. it can.
  • the film thickness of the hole transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m, preferably 5 to 200 nm.
  • the hole transport layer may have a single layer structure composed of one or more of the above materials.
  • a hole transport layer having a high p property doped with impurities examples thereof include JP-A-4-297076, JP-A-2000-196140, JP-A-2001-102175, J. Pat. Appl. Phys. 95, 5773 (2004), and the like.
  • a hole transport layer having such a high p property because a device with lower power consumption can be produced.
  • an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used.
  • electrode materials include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • an amorphous material such as IDIXO (In 2 O 3 —ZnO) capable of forming a transparent conductive film may be used.
  • these electrode materials may be formed into a thin film by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method, or when pattern accuracy is not required (about 100 ⁇ m or more)
  • a pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode material.
  • a wet film forming method such as a printing method or a coating method can also be used.
  • the transmittance be greater than 10%, and the sheet resistance as the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness depends on the material, it is usually selected in the range of 10 to 1000 nm, preferably 10 to 200 nm.
  • the support substrate (hereinafter also referred to as a substrate, substrate, substrate, support, etc.) that can be used in the organic EL device of the present invention is not particularly limited in the type of glass, plastic, etc., and is transparent. May be opaque. When extracting light from the support substrate side, the support substrate is preferably transparent. Examples of the transparent support substrate preferably used include glass, quartz, and a transparent resin film. A particularly preferable support substrate is a resin film capable of giving flexibility to the organic EL element.
  • polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polyethylene, polypropylene, cellophane, cellulose diacetate, cellulose triacetate, cellulose acetate butyrate, cellulose acetate propionate (CAP), Cellulose esters such as cellulose acetate phthalate (TAC) and cellulose nitrate or derivatives thereof, polyvinylidene chloride, polyvinyl alcohol, polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, polymethylpentene, polyether ketone, polyimide , Polyethersulfone (PES), polyphenylene sulfide, polysulfones Cycloolefin resins such as polyetherimide, polyetherketoneimide, polyamide, fluororesin, nylon, polymethylmethacrylate, acrylic or polyarylate, Arton (trade name, manufactured by JSR) or Appel (
  • the surface of the resin film may be formed with an inorganic film, an organic film, or a hybrid film of both, and the water vapor permeability (25 ⁇ 0.5 ° C.) measured by a method according to JIS K 7129-1992.
  • Relative humidity (90 ⁇ 2)% RH) is preferably 0.01 g / (m 2 ⁇ 24 h) or less, and further, oxygen measured by a method according to JIS K 7126-1987.
  • a high barrier film having a permeability of 10 ⁇ 3 ml / (m 2 ⁇ 24 h ⁇ atm) or less and a water vapor permeability of 10 ⁇ 5 g / (m 2 ⁇ 24 h) or less is preferable.
  • the material for forming the barrier film may be any material that has a function of suppressing the intrusion of elements that cause deterioration of elements such as moisture and oxygen.
  • silicon oxide, silicon dioxide, silicon nitride, or the like can be used.
  • the method for forming the barrier film is not particularly limited.
  • vacuum deposition, sputtering, reactive sputtering, molecular beam epitaxy, cluster ion beam, ion plating, plasma polymerization, atmospheric pressure plasma polymerization A plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used, but an atmospheric pressure plasma polymerization method as described in JP-A-2004-68143 is particularly preferable.
  • the opaque support substrate examples include metal plates such as aluminum and stainless steel, films, opaque resin substrates, ceramic substrates, and the like.
  • the external extraction efficiency at room temperature of light emission of the organic EL element of the present invention is preferably 1% or more, more preferably 5% or more.
  • the external extraction quantum efficiency (%) the number of photons emitted to the outside of the organic EL element / the number of electrons sent to the organic EL element ⁇ 100.
  • a hue improvement filter such as a color filter may be used in combination, or a color conversion filter that converts the emission color from the organic EL element into multiple colors using a phosphor may be used in combination.
  • the ⁇ max of light emission of the organic EL element is preferably 480 nm or less.
  • a thin film made of a desired electrode material for example, a material for an anode is formed on a suitable substrate so as to have a thickness of 1 ⁇ m or less, preferably 10 to 200 nm, thereby producing an anode.
  • 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, an electron transport layer, or a cathode buffer layer, which is an element material, is formed thereon.
  • the thin film can be formed by a vacuum deposition method, a wet method (also referred to as a wet process) or the like.
  • Wet methods include spin coating, casting, die coating, blade coating, roll coating, ink jet, printing, spray coating, curtain coating, and LB, but precise thin films can be formed.
  • a method having high suitability for a roll-to-roll method such as a die coating method, a roll coating method, an ink jet method, or a spray coating method is preferable. Different film forming methods may be applied for each layer.
  • liquid medium for dissolving or dispersing the organic EL material according to the present invention examples include ketones such as methyl ethyl ketone and cyclohexanone, fatty acid esters such as ethyl acetate, halogenated hydrocarbons such as dichlorobenzene, toluene, xylene, and mesitylene.
  • ketones such as methyl ethyl ketone and cyclohexanone
  • fatty acid esters such as ethyl acetate
  • halogenated hydrocarbons such as dichlorobenzene, toluene, xylene, and mesitylene.
  • Aromatic hydrocarbons such as cyclohexylbenzene, aliphatic hydrocarbons such as cyclohexane, decalin, and dodecane
  • organic solvents such as DMF and DMSO
  • a dispersion method it can be dispersed by a dispersion method such as ultrasonic wave, high shearing force dispersion or media dispersion.
  • a thin film made of a cathode material is formed thereon so as to have a thickness of 1 ⁇ m or less, preferably in the range of 50 to 200 nm, and a desired organic EL device can be obtained by providing a cathode. .
  • the cathode, cathode buffer layer, electron transport layer, hole blocking layer, light emitting layer, hole transport layer, hole injection layer, and anode can be formed in the reverse order.
  • a DC voltage When a DC voltage is applied to the multicolor display device thus obtained, light emission can be observed by applying a voltage of about 2 to 40 V with the positive polarity of the anode and the negative polarity of the cathode.
  • An alternating voltage may be applied.
  • the alternating current waveform to be applied may be arbitrary.
  • the production of the organic EL device of the present invention is preferably produced 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 preferable to perform the work in a dry inert gas atmosphere.
  • ⁇ Sealing> As a sealing means used for this invention, the method of adhere
  • the sealing member may be disposed so as to cover the display area of the organic EL element, and may be a concave plate shape or a flat plate shape. Further, transparency and electrical insulation are not particularly limited.
  • Specific examples include a glass plate, a polymer plate / film, and a metal plate / film.
  • the glass plate include soda-lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
  • examples of the polymer plate include those formed from polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, polysulfone and the like.
  • the metal plate examples include those made of one or more metals or alloys selected from the group consisting of stainless steel, iron, copper, aluminum, magnesium, nickel, zinc, chromium, titanium, molybdenum, silicon, germanium, and tantalum.
  • a polymer film and a metal film can be preferably used because the element can be thinned.
  • the polymer film has an oxygen permeability measured by a method according to JIS K 7126-1987 of 1 ⁇ 10 ⁇ 3 ml / (m 2 ⁇ 24 h ⁇ atm) or less, and a method according to JIS K 7129-1992. It is preferable that the water vapor permeability (25 ⁇ 0.5 ° C., relative humidity (90 ⁇ 2)% RH) measured in (1) is 1 ⁇ 10 ⁇ 3 g / (m 2 ⁇ 24 h) or less.
  • sealing member For processing the sealing member into a concave shape, sandblasting, chemical etching, or the like is used.
  • the adhesive include photocuring and thermosetting adhesives having reactive vinyl groups of acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanoacrylates. be able to.
  • hot-melt type polyamide, polyester, and polyolefin can be mentioned.
  • a cationic curing type ultraviolet curing epoxy resin adhesive can be mentioned.
  • an organic EL element may deteriorate by heat processing, what can be adhesively cured from room temperature to 80 ° C. is preferable.
  • a desiccant may be dispersed in the adhesive.
  • coating of the adhesive agent to a sealing part may use commercially available dispenser, and may print like screen printing.
  • the electrode and the organic layer are coated on the outside of the electrode facing the support substrate with the organic layer interposed therebetween, and an inorganic or organic layer is formed in contact with the support substrate to form a sealing film.
  • the material for forming the film may be any material that has a function of suppressing intrusion of elements that cause deterioration of elements such as moisture and oxygen.
  • silicon oxide, silicon dioxide, silicon nitride, or the like may be used. it can.
  • the method for forming these films is not particularly limited.
  • vacuum deposition, sputtering, reactive sputtering, molecular beam epitaxy, cluster ion beam, ion plating, plasma polymerization, atmospheric pressure plasma A combination method, a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used.
  • an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil can be injected in the gas phase and liquid phase.
  • an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil
  • a vacuum is also possible.
  • a hygroscopic compound can also be enclosed inside.
  • hygroscopic compound examples include metal oxides (for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide) and sulfates (for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate).
  • metal oxides for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide
  • sulfates for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate.
  • metal halides eg calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, barium iodide, magnesium iodide etc.
  • perchloric acids eg perchloric acid Barium, magnesium perchlorate, and the like
  • anhydrous salts are preferably used in sulfates, metal halides, and perchloric acids.
  • a protective film or a protective plate may be provided on the outer side of the sealing film on the side facing the support substrate with the organic layer interposed therebetween or on the sealing film.
  • the mechanical strength is not necessarily high. Therefore, it is preferable to provide such a protective film and a protective plate.
  • the same glass plate, polymer plate / film, metal plate / film, and the like used for the sealing can be used.
  • the polymer film is light and thin. Is preferably used.
  • the organic EL element emits light inside a layer having a refractive index higher than that of air (refractive index is about 1.7 to 2.1) and can extract only about 15% to 20% of the light generated in the light emitting layer. It is generally said. This is because light incident on the interface (interface between the transparent substrate and air) at an angle ⁇ greater than the critical angle causes total reflection and cannot be taken out of the device, or between the transparent electrode or light emitting layer and the transparent substrate. This is because the light is totally reflected between the light and the light is guided through the transparent electrode or the light emitting layer, and as a result, the light escapes in the direction of the element side surface.
  • a method of improving the light extraction efficiency for example, a method of forming irregularities on the surface of the transparent substrate and preventing total reflection at the transparent substrate and the air interface (US Pat. No. 4,774,435), A method for improving efficiency by giving light condensing property to a substrate (Japanese Patent Laid-Open No. 63-314795), a method of forming a reflective surface on the side surface of an element (Japanese Patent Laid-Open No. 1-220394), and light emission from the substrate A method of forming an antireflection film by introducing a flat layer having an intermediate refractive index between the bodies (Japanese Patent Laid-Open No.
  • these methods can be used in combination with the organic EL device of the present invention.
  • a method of introducing a flat layer having a lower refractive index than the substrate between the substrate and the light emitter, or a substrate, transparent A method of forming a diffraction grating between any layers of the electrode layer and the light emitting layer (including between the substrate and the outside) can be suitably used.
  • the low refractive index layer examples include aerogel, porous silica, magnesium fluoride, and a fluorine-based polymer. Since the refractive index of the transparent substrate is generally about 1.5 to 1.7, the low refractive index layer preferably has a refractive index of about 1.5 or less. Further, it is preferably 1.35 or less.
  • the thickness of the low refractive index medium is preferably at least twice the wavelength in the medium. This is because the effect of the low refractive index layer is diminished when the thickness of the low refractive index medium is about the wavelength of light and the electromagnetic wave that has exuded by evanescent enters the substrate.
  • the method of introducing a diffraction grating into an interface or any medium that causes total reflection is characterized by a high effect of improving light extraction efficiency.
  • This method uses the property that the diffraction grating can change the direction of light to a specific direction different from refraction by so-called Bragg diffraction such as first-order diffraction and second-order diffraction.
  • Bragg diffraction such as first-order diffraction and second-order diffraction.
  • light that cannot go out due to total reflection between layers, etc. is diffracted by introducing a diffraction grating into any layer or medium (inside a transparent substrate or transparent electrode). I want to take it out.
  • the diffraction grating to be introduced has a two-dimensional periodic refractive index. This is because light emitted from the light-emitting layer is randomly generated in all directions, so in a general one-dimensional diffraction grating having a periodic refractive index distribution only in a certain direction, only light traveling in a specific direction is diffracted. Therefore, the light extraction efficiency does not increase so much.
  • the refractive index distribution a two-dimensional distribution
  • the light traveling in all directions is diffracted, and the light extraction efficiency is increased.
  • the position where the diffraction grating is introduced may be in any interlayer or medium (in the transparent substrate or in the transparent electrode), but is preferably in the vicinity of the organic light emitting layer where light is generated.
  • the period of the diffraction grating is preferably about 1/2 to 3 times the wavelength of light in the medium.
  • the arrangement of the diffraction grating is preferably two-dimensionally repeated such as a square lattice, a triangular lattice, or a honeycomb lattice.
  • the organic EL element of the present invention can be processed on a light extraction side of a substrate, for example, by providing a microlens array-like structure, or combined with a so-called condensing sheet, for example in a specific direction, for example, with respect to the element light emitting surface.
  • a condensing sheet for example in a specific direction, for example, with respect to the element light emitting surface.
  • quadrangular pyramids having a side of 30 ⁇ m and an apex angle of 90 degrees are arranged two-dimensionally on the light extraction side of the substrate.
  • One side is preferably 10 to 100 ⁇ m. If it becomes smaller than this, the effect of diffraction will generate
  • the condensing sheet it is possible to use, for example, a sheet that has been put to practical use in an LED backlight of a liquid crystal display device.
  • a brightness enhancement film (BEF) manufactured by Sumitomo 3M Limited can be used.
  • the base material may be formed by forming a ⁇ -shaped stripe having a vertex angle of 90 degrees and a pitch of 50 ⁇ m, or the vertex angle is rounded and the pitch is changed randomly. Other shapes may be used.
  • a light diffusion plate / film may be used in combination with the light collecting sheet.
  • a diffusion film (light-up) manufactured by Kimoto Co., Ltd. can be used.
  • the organic EL element of the present invention can be used as a display device, a display, and various light emission sources.
  • lighting devices home lighting, interior lighting
  • clock and liquid crystal backlights billboard advertisements, traffic lights, light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light
  • the light source of a sensor etc. are mentioned, It is not limited to this, Especially, it can use effectively for the use as a backlight of a liquid crystal display device, and a light source for illumination.
  • patterning may be performed by a metal mask, an ink jet printing method, or the like when forming a film, if necessary.
  • patterning only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire layer of the element may be patterned.
  • a conventionally known method is used. Can do.
  • the light emission color of the organic EL device of the present invention and the compound according to the present invention is shown in FIG. 4.16 on page 108 of “New Color Science Handbook” (edited by the Japan Color Society, University of Tokyo Press, 1985). It is determined by the color when the result measured with a total of CS-1000 (manufactured by Konica Minolta Sensing Co., Ltd.) is applied to the CIE chromaticity coordinates.
  • the display device of the present invention comprises the organic EL element of the present invention.
  • the display device of the present invention may be single color or multicolor, but here, the multicolor display device will be described.
  • a shadow mask is provided only at the time of forming a light emitting layer, and a film can be formed on one surface by vapor deposition, casting, spin coating, ink jet, printing, or the like.
  • the method is not limited, but is preferably a vapor deposition method, an inkjet method, a spin coating method, or a printing method.
  • the configuration of the organic EL element included in the display device is selected from the above-described configuration examples of the organic EL element as necessary.
  • the manufacturing method of an organic EL element is as having shown in the one aspect
  • a DC voltage When a DC voltage is applied to the obtained multicolor display device, light emission can be observed by applying a voltage of about 2V to 40V with the positive polarity of the anode and the negative polarity of the cathode. Further, even when a voltage is applied with the opposite polarity, no current flows and no light emission occurs. Further, when an AC voltage is applied, light is emitted only when the anode is in the + state and the cathode is in the-state.
  • the alternating current waveform to be applied may be arbitrary.
  • the multicolor display device can be used as a display device, a display, and various light sources.
  • a display device or display full-color display is possible by using three types of organic EL elements of blue, red, and green light emission.
  • Display devices and displays include televisions, personal computers, mobile devices, AV devices, teletext displays, information displays in automobiles, and the like. In particular, it may be used as a display device for reproducing still images and moving images, and the driving method when used as a display device for reproducing moving images may be either a simple matrix (passive matrix) method or an active matrix method.
  • 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 sources for optical sensors, etc.
  • the present invention is not limited to these examples.
  • FIG. 1 is a schematic view showing an example of a display device composed of organic EL elements. 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 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 pixels for each scanning line respond to the image data signal by the scanning signal.
  • the image information is sequentially emitted to scan the image and display the image information on the display unit A.
  • FIG. 2 is a schematic diagram of the display unit A.
  • the display unit A has a wiring unit including a plurality of scanning lines 5 and data lines 6 and a plurality of pixels 3 on the substrate.
  • the main members of the display unit A will be described below.
  • the light emitted from the pixel 3 is extracted in the direction of the white arrow (downward).
  • the scanning line 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning 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 are illustrated). Not)
  • the pixel 3 When the scanning signal is applied from the scanning line 5, the pixel 3 receives the image data signal from the data line 6 and emits light according to the received image data.
  • a full color display can be achieved 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 includes an organic EL element 10, a switching transistor 11, a driving transistor 12, a capacitor 13, and the like.
  • a full color display can be performed by using red, green, and blue light emitting organic EL elements as the organic EL elements 10 in a plurality of pixels, and juxtaposing them on the same substrate.
  • an image data signal is applied from the control unit B to the drain of the switching transistor 11 via the data line 6.
  • a scanning signal is applied from the control unit B to the gate of the switching transistor 11 via the scanning line 5
  • the driving of the switching transistor 11 is turned on, and the image data signal applied to the drain is supplied to the capacitor 13 and the driving transistor 12. Is transmitted to the gate.
  • the capacitor 13 is charged according to the potential of the image data signal, and 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 power supply line 7 connects to the organic EL element 10 according to the potential of the image data signal applied to the gate. Current is supplied.
  • 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 maintains 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. Until then, the light emission of the organic EL element 10 continues.
  • 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 light emission of the organic EL element 10 is performed by providing the switching transistor 11 and the drive transistor 12 which are active elements with respect to the organic EL element 10 of each of the plurality of pixels. It is carried out.
  • Such a light emitting method is called an active matrix method.
  • the light emission of the organic EL element 10 may be light emission of a plurality of gradations by a multi-value image data signal having a plurality of gradation potentials, or by turning on / off a predetermined light emission amount by a binary image data signal. Good.
  • the potential of the capacitor 13 may be maintained until the next scanning signal is applied, or may be discharged immediately before the next scanning signal is applied.
  • the present invention not only the active matrix method described above, but also a passive matrix light emission drive in which an organic EL element emits light according to a data signal only when a scanning signal is scanned.
  • FIG. 4 is a schematic view of a passive matrix display device.
  • 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 lighting device of the present invention will be described.
  • the illuminating device of this invention has the said organic EL element.
  • the organic EL element of the present invention may be used as an organic EL element having a resonator structure.
  • the purpose of use of the organic EL element having such a resonator structure is as follows.
  • the light source of a machine, the light source of an optical communication processing machine, the light source of a photosensor, etc. are mentioned, However, It is not limited to these. Moreover, you may use for the said use by making a laser oscillation.
  • the organic EL element of the present invention may be used as a kind of lamp for illumination or exposure light source, a projection device for projecting an image, or a display for directly viewing a still image or a moving image. It may be used as a device (display).
  • the drive method when used as a display device for moving image reproduction may be either a simple matrix (passive matrix) method or an active matrix method.
  • the organic EL material of the present invention can 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 a plurality of emission colors may include three emission maximum wavelengths of the three primary colors of blue, green, and blue, or two using the relationship of complementary colors such as blue and yellow, blue green and orange, etc. The thing containing the light emission maximum wavelength may be used.
  • a combination of light emitting materials for obtaining a plurality of emission colors is a combination of a plurality of phosphorescent or fluorescent materials, a light emitting material that emits fluorescence or phosphorescence, and light from the light emitting material as excitation light. Any of those combined with a dye material that emits light may be used, but in the white organic EL device according to the present invention, only a combination of a plurality of light-emitting dopants may be mixed.
  • an electrode film can be formed by a vapor deposition method, a cast method, a spin coating method, an ink jet method, a printing method, or the like, and productivity is also improved.
  • the elements themselves are luminescent white.
  • luminescent material used for a light emitting layer For example, if it is a backlight in a liquid crystal display element, the metal complex which concerns on this invention so that it may suit the wavelength range corresponding to CF (color filter) characteristic, Any one of known luminescent materials may be selected and combined to whiten.
  • CF color filter
  • the non-light emitting surface of the organic EL device of the present invention is covered with a glass case, a glass substrate having a thickness of 300 ⁇ m is used as a sealing substrate, and an epoxy-based photocurable adhesive (LUX TRACK manufactured by Toagosei Co., Ltd.) is used as a sealing material.
  • LC0629B is applied, and this is overlaid on the cathode and brought into close contact with the transparent support substrate, irradiated with UV light from the glass substrate side, cured and sealed, and an illumination device as shown in FIGS. Can be formed.
  • FIG. 5 shows a schematic diagram of a lighting device, and the organic EL element 101 of the present invention is covered with a glass cover 102 (in addition, the sealing operation with the glass cover is to bring the organic EL element 101 into contact with the atmosphere. And a glove box under a nitrogen atmosphere (in an atmosphere of high-purity nitrogen gas having a purity of 99.999% or more).
  • FIG. 6 shows a cross-sectional view of the lighting device.
  • 105 denotes a cathode
  • 106 denotes an organic EL layer
  • 107 denotes a glass substrate with a transparent electrode.
  • the glass cover 102 is filled with nitrogen gas 108 and a water catching agent 109 is provided.
  • Example 1 Production of Organic EL Element 1-1 >> Patterning was performed on a substrate (manufactured by Avantate, NA-45) in which ITO (indium tin oxide) was formed to a thickness of 100 nm on a glass substrate of 100 mm ⁇ 100 mm ⁇ 1.1 mm as an anode. Thereafter, the transparent support substrate provided with the ITO transparent electrode was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • ITO indium tin oxide
  • a solution obtained by diluting poly (3,4-ethylenedioxythiophene) -polystyrene sulfonate (PEDOT / PSS, Bayer, Baytron P Al 4083) to 70% with pure water is spin-coated. Then, the film was dried at 200 ° C. for 1 hour to provide a first hole transport layer having a thickness of 30 nm.
  • a hole transport material Poly N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl)) benzidine (manufactured by American Dye Source, ADS- The chlorobenzene solution of No. 254) was formed by spin coating. It heat-dried at 150 degreeC for 1 hour, and provided the 2nd hole transport layer with a film thickness of 40 nm.
  • a host compound OC-11 and a butyl acetate solution of Comparative Example 1 as a dopant compound were formed by spin coating, dried by heating at 120 ° C. for 1 hour, and a 40 nm thick light emitting layer was established.
  • a 1-butanol solution of the electron transport material ET-11 was formed by spin coating to provide an electron transport layer having a thickness of 20 nm.
  • the emission luminance was measured using CS-1000 (manufactured by Konica Minolta Sensing), and the external extraction quantum efficiency was expressed as a relative value with the organic EL element 1-2 (comparative example) as 100.
  • the organic EL element 1-2 (comparative example) was set to 100 and indicated as a relative value.
  • the half life was displayed as a relative value when the comparative organic EL element 1-2 (comparative example) was set to 100.
  • the organic EL device was visually evaluated for the luminescent color when the organic EL device was continuously lit under a constant current condition of 2.5 mA / cm 2 at room temperature.
  • the organic EL elements 1-3 to 1-21 of the present invention produced using the organic EL element material of the present invention have higher efficiency than the comparative organic EL elements 1-1 and 1-2. It is apparent that the device characteristics are improved, for example, the half-life is improved and the drive voltage is also reduced.
  • the light emission color (also referred to simply as color) of the element is light emission of pure blue to blue green.
  • Example 2 Preparation of organic EL elements 2-1 to 2-16
  • the organic EL elements 2-1 to 2-16 were similarly prepared except that the host compound OC-11 of the light emitting layer and the comparative compound 1 as the dopant compound were replaced with the compounds shown in Table 2.
  • the host compound OC-11 of the light emitting layer and the comparative compound 1 as the dopant compound were replaced with the compounds shown in Table 2.
  • Example 2 Example 2
  • the same procedure as described in Example 1 was performed.
  • the external extraction quantum efficiency was expressed as a relative value with the organic EL element 2-2 (comparative example) as 100.
  • Each organic EL element was evaluated for rank as follows by visually observing the light emitting surface at the time of continuous lighting under a constant current condition of 2.5 mA / cm 2 at room temperature. In addition, visual observation is visual evaluation by 10 people extracted at random.
  • ⁇ The number of people who confirmed dark spots was 5 or more. ⁇ : The number of people confirmed dark spots was 1 to 4. ⁇ : The number of people confirmed dark spots was zero.
  • the organic EL elements 2-3 to 2-16 of the present invention produced using the organic EL element material of the present invention have higher efficiency than the comparative organic EL elements 2-1 to 2-2. It is clear that the various characteristics of the device have been improved, such as suppressing dark spots and voltage rise.
  • the emission color (also simply referred to as color) of the organic EL element of the present invention is a short blue light emission of pure blue to blue green compared to the comparative organic EL element.
  • Example 3 Production of Organic EL Element 3-1 >> Transparent support provided with this ITO transparent electrode after patterning on a substrate (NH45 manufactured by NH Techno Glass) made of ITO (indium tin oxide) with a thickness of 100 nm on a glass substrate of 100 mm ⁇ 100 mm ⁇ 1.1 mm as an anode
  • the substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • PEDOT / PSS polystyrene sulfonate
  • This transparent support substrate was fixed to a substrate holder of a commercially available vacuum deposition apparatus. Meanwhile, 200 mg of ⁇ -NPD was put in a molybdenum resistance heating boat, and 200 mg of OC-30 as a host compound was put in another resistance heating boat made of molybdenum. Another molybdenum resistance heating boat was charged with 200 mg of ET-8, and another molybdenum resistance heating boat was charged with 100 mg of Comparative Compound 5 as a dopant compound, and attached to a vacuum deposition apparatus.
  • the vacuum chamber was then depressurized to 4 ⁇ 10 ⁇ 4 Pa, heated by energizing the heating boat containing ⁇ -NPD, evaporated onto a transparent support substrate at a deposition rate of 0.1 nm / second, and a second positive 20 nm.
  • a hole transport layer was provided.
  • the heating boat containing the host compound OC-30 and the comparative compound 5 which is a dopant compound is energized and heated, and each of them is deposited on the hole transport layer at a deposition rate of 0.1 nm / second and 0.006 nm / second, respectively.
  • the light emitting layer of 40 nm was provided by vapor deposition.
  • the heating boat containing ET-8 was energized and heated, and deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide an electron transport layer having a thickness of 30 nm.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • lithium fluoride 0.5 nm was vapor-deposited as a cathode buffer layer, and aluminum 110 nm was vapor-deposited to form a cathode, whereby an organic EL element 3-1 was produced.
  • Luminance brightness The light emission luminance (cd / m 2 ) when a temperature of 23 ° C. and a DC voltage of 10 V were applied to the organic EL element was measured. The light emission luminance is expressed as a relative value when the organic EL element 3-1 is 100. The light emission luminance was measured using CS-1000 (manufactured by Konica Minolta Sensing).
  • the emission luminance when a constant current of 2.5 mA / cm 2 was applied at room temperature in a dry nitrogen gas atmosphere was measured using a spectral radiance meter CS-1000 (manufactured by Konica Minolta Sensing).
  • Voltage rise after storage (drive voltage after storage of each element / drive voltage before storage of each element) Note that the closer the value is to 1, the smaller the increase in drive voltage before and after storage.
  • the organic EL elements 3-2 to 3-16 of the present invention produced using the organic EL element material of the present invention each showed higher emission luminance than the comparative organic EL element 3-1. It is apparent that various characteristics as an element are improved, such as uneven light emission and voltage increase of the storage element can be suppressed.
  • the emission color (also simply referred to as color) of the organic EL element of the present invention is a short blue light emission of pure blue to blue green compared to the comparative organic EL element.
  • Example 4 Production of organic EL elements 4-1 to 4-12>
  • the organic EL elements 4-1 to 4-12 were similarly prepared except that the compound 5 shown in Table 4 was replaced with the host compound OC-4 of the light emitting layer and the dopant compound Comparative 5.
  • the compound 5 shown in Table 4 was replaced with the host compound OC-4 of the light emitting layer and the dopant compound Comparative 5.
  • Example 3 Luminance brightness
  • the same procedure as described in Example 3 was performed.
  • the emission luminance was expressed as a relative value when the organic EL element 4-1 (comparative example) was set to 100.
  • the initial deterioration was evaluated according to the measurement method shown below. When the half-life was measured, the time required for the luminance to reach 90% was measured and used as a measure of initial deterioration.
  • the initial deterioration was calculated based on the following formula.
  • Initial degradation (luminance 90% arrival time of organic EL element 4-1) / (luminance 90% arrival time of each element) ⁇ 100 That is, the smaller the initial deterioration value, the smaller the initial deterioration.
  • Example 2 The same procedure as described in Example 1 was performed. The drive voltage is shown as a relative value with the organic EL element 4-1 (comparative example) as 100.
  • the organic EL elements 4-2 to 4-12 of the present invention produced using the organic EL element material of the present invention each showed higher emission luminance than the comparative organic EL element 4-1. It is clear that various characteristics as an element are improved such that initial deterioration is suppressed and driving voltage is also reduced.
  • the emission color (also simply referred to as color) of the organic EL element of the present invention is a short blue light emission of pure blue to blue green compared to the comparative organic EL element.
  • Example 5 Preparation of white light-emitting organic EL element 5-1 >> Patterning was performed on a substrate (manufactured by Avantate, NA-45) in which ITO (indium tin oxide) was formed to a thickness of 100 nm on a glass substrate of 100 mm ⁇ 100 mm ⁇ 1.1 mm as an anode. Thereafter, the transparent support substrate provided with the ITO transparent electrode was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • ITO indium tin oxide
  • a solution obtained by diluting poly (3,4-ethylenedioxythiophene) -polystyrene sulfonate (PEDOT / PSS, Bayer, Baytron P Al 4083) to 70% with pure water is spin-coated. Then, the film was dried at 200 ° C. for 1 hour to provide a first hole transport layer having a thickness of 30 nm.
  • a hole transport material Poly N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl)) benzidine (manufactured by American Dye Source, ADS- The chlorobenzene solution of No. 254) was formed by spin coating. It heat-dried at 150 degreeC for 1 hour, and provided the 2nd hole transport layer with a film thickness of 40 nm.
  • a solution obtained by dissolving the host compound OC-11 (100 mg) and the dopant C3 (16 mg) in 6 ml of hexafluoroisopropanol (HFIP) is used on this first light emitting layer by spin coating under the conditions of 2000 rpm and 30 seconds. A film was formed and vacuum-dried at 60 ° C. for 1 hour to form a second light emitting layer.
  • HFIP hexafluoroisopropanol
  • This substrate is fixed to a substrate holder of a vacuum evaporation apparatus, and the vacuum chamber is depressurized to 4 ⁇ 10 ⁇ 4 Pa. Then, the electron transport material ET-9 is formed on the second light emitting layer as a cathode buffer layer by 30 nm and subsequently as a cathode buffer layer.
  • a cathode was formed by vapor-depositing lithium fluoride at 0.5 nm and further using aluminum as a cathode at 110 nm to prepare an organic EL device 5-1.
  • Example 6 Preparation of white light-emitting organic EL element 6-1 >> Patterning was performed on a substrate (manufactured by Avantate, NA-45) in which ITO (indium tin oxide) was formed to a thickness of 100 nm on a glass substrate of 100 mm ⁇ 100 mm ⁇ 1.1 mm as an anode. Thereafter, the transparent support substrate provided with the ITO transparent electrode was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • ITO indium tin oxide
  • a solution obtained by diluting poly (3,4-ethylenedioxythiophene) -polystyrene sulfonate (PEDOT / PSS, Bayer, Baytron P Al 4083) to 70% with pure water is spin-coated. Then, the film was dried at 200 ° C. for 1 hour to provide a first hole transport layer having a thickness of 30 nm.
  • a hole transport material Poly N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl)) benzidine (manufactured by American Dye Source, ADS- The chlorobenzene solution of No. 254) was formed by spin coating. It heat-dried at 150 degreeC for 1 hour, and provided the 2nd hole transport layer with a film thickness of 40 nm.
  • spin coating was performed under the conditions of 2000 rpm and 30 seconds using a solution of 7 (100 mg), dopant materials D-1 (3 mg), D-6 (3 mg), and C89 (16 mg) dissolved in 10 ml of toluene as a host.
  • the film was formed by the method.
  • a light emitting layer was formed by vacuum drying at 60 ° C. for 1 hour.
  • This substrate was fixed to a substrate holder of a vacuum deposition apparatus, and the vacuum chamber was depressurized to 4 ⁇ 10 ⁇ 4 Pa, and then the electron transport material ET-15 was 30 nm on the light emitting layer, followed by lithium fluoride as a cathode buffer layer.
  • the organic EL element 6-1 was prepared by depositing aluminum with a thickness of 0.5 nm and further depositing aluminum with a thickness of 110 nm as the cathode.
  • Example 7 Production of White Light-Emitting Organic EL Element 7-1 >> Transparent support provided with this ITO transparent electrode after patterning on a substrate (NH45 manufactured by NH Techno Glass) made of ITO (indium tin oxide) with a thickness of 100 nm on a glass substrate of 100 mm ⁇ 100 mm ⁇ 1.1 mm as an anode The substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • a substrate NH45 manufactured by NH Techno Glass
  • ITO indium tin oxide
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while 200 mg of ⁇ -NPD is put into a molybdenum resistance heating boat, and 200 mg of 9 as a host compound is put into another resistance heating boat made of molybdenum.
  • 200 mg of ET-11 into a resistance heating boat made of molybdenum put 100 mg of C35 as a dopant compound into another resistance heating boat made of molybdenum, put 100 mg of D-10 as a dopant compound into another resistance heating boat made of molybdenum, and vacuum Attached to the vapor deposition apparatus.
  • each of the heating boats containing ⁇ -NPD was separately energized and deposited on the transparent support substrate at a deposition rate of 0.1 nm / sec. A hole transport layer was provided.
  • the deposition rate of host compound 9 and dopant compounds C35 and D-10 is 100. : Adjusted to 5: 0.6, vapor-deposited to a thickness of 30 nm to provide a light emitting layer.
  • the heating boat containing ET-11 was energized and heated, and deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide an electron transport layer having a thickness of 30 nm.
  • the substrate temperature at the time of vapor deposition was room temperature.
  • lithium fluoride 0.5 nm was vapor-deposited as a cathode buffer layer, and aluminum 110 nm was vapor-deposited to form a cathode, whereby an organic EL element 7-1 was produced.
  • Example 8 Below, the synthesis example of a typical compound is shown.
  • Step 3 Synthesis of Ligand A1 Under a nitrogen atmosphere, 30 g of triphenyl (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) silane ( 64.87 mmol) and 2-bromo-1- (2,4,6-trimethylphenyl) -1H-imidazole 17.20 g (64.87 mmol), tetrakis (triphenylphosphine) palladium (0) 7.5 g (6 .49 mmol), 13.44 g (97.30 mmol) of potassium carbonate, 200 ml of 1,2-dimethoxyethane (DME) and 20 ml of pure water were added, and the mixture was stirred at an internal temperature of 70 ° C. for 5 hours.
  • triphenyl 3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) silane ( 64.87 mmol) and 2-bro
  • the phosphorescence emission wavelength of the solution of Exemplified Compound C3 measured using a spectrofluorometer F-4500 manufactured by Hitachi, Ltd. was 458 nm (in 2-methyltetrahydrofuran).
  • the phosphorescence wavelength of D-26, which does not have the substituent of general formula (1), was measured in the same manner, and was 467 nm, which was shortened by introducing the substituent of general formula (1). was confirmed.
  • Example Compound C24 in a 2-methyltetrahydrofuran solution measured using a spectrofluorometer F-4500 manufactured by Hitachi, Ltd. was 456 nm.
  • Example 9 Production of Organic EL Element 9-1 to Example 9-15 >> In the production of the organic EL device 1-1, the organic EL device was similarly prepared except that the host compound OC-11 of the light emitting layer, the comparison 1 as the dopant compound, and the electron transport material ET-11 were replaced with the compounds shown in Table 5. 9-1 to 9-15 were produced.
  • Example 2 Example 2
  • the same procedure as described in Example 1 was performed.
  • the external extraction quantum efficiency was expressed as a relative value with the organic EL element 9-2 (comparative example) as 100.
  • the organic EL elements 9-3 to 9-15 of the present invention produced using the organic EL element material of the present invention have higher efficiency than the comparative organic EL elements 9-1 and 9-2. It is apparent that the device characteristics are improved, such as improved half-life, reduced drive voltage, and excellent temporal stability.
  • the light emission color (also referred to simply as color) of the element is light emission of pure blue to blue green.
  • Example 10 Production of Organic EL Element 10-1 to Example 10-14 >> In the production of the organic EL device 1-1, the organic EL device was similarly prepared except that the host compound OC-11 of the light emitting layer, the comparison 1 as the dopant compound, and the electron transport material ET-11 were replaced with the compounds shown in Table 6. 10-1 to 10-14 were produced.
  • Example 2 Example 2
  • the same procedure as described in Example 1 was performed.
  • the external extraction quantum efficiency was expressed as a relative value with the organic EL element 10-2 (comparative example) as 100.
  • the voltage rise at the time of driving is the ratio of the voltage at constant current driving at an initial luminance of 3000 cd / m 2 and the voltage at half luminance.
  • the organic EL elements 10-3 to 10-14 of the present invention produced using the organic EL element material of the present invention have higher efficiency than the comparative organic EL elements 10-1 and 10-2. It is apparent that the device characteristics are improved, such as an improvement in half-life, reduction in driving voltage, and suppression of voltage increase during driving.
  • the light emission color (also referred to simply as color) of the element is light emission of pure blue to blue green.
  • Example 11 Production of Organic EL Element 11-1 to Example 11-14 >> In the production of the organic EL device 3-1, the organic EL device was similarly prepared except that the host compound OC-30 of the light emitting layer, the comparison 3 as the dopant compound, and the electron transport material ET-8 were replaced with the compounds shown in Table 7. 11-1 to 11-14 were produced.
  • Example 2 Example 2
  • the same procedure as described in Example 1 was performed.
  • the external extraction quantum efficiency was expressed as a relative value with the organic EL element 11-1 (comparative example) as 100.
  • Example 2 The same procedure as described in Example 1 was performed. The half life was expressed as a relative value where the organic EL element 11-1 (comparative example) was 100.
  • the organic EL elements 11-3 to 11-14 of the present invention produced using the organic EL element material of the present invention have higher efficiency than the comparative organic EL elements 11-1 and 11-2. It is apparent that the device characteristics are improved such that the half-life is improved, the driving voltage is reduced, and initial deterioration can be suppressed.
  • the light emission color (also referred to simply as color) of the element is light emission of pure blue to blue green.
  • Example 12 Production of Organic EL Element 12-1 to Example 12-14 >> In the production of the organic EL element 3-1, the organic EL element was similarly prepared except that the host compound OC-30 of the light emitting layer, the comparative compound 3 as a dopant compound, and the electron transport material ET-8 were replaced with the compounds shown in Table 8. 12-1 to 12-14 were produced.
  • the organic EL elements 12-1 to 12-14 obtained were evaluated as described below.
  • Example 2 Example 2
  • the same procedure as described in Example 1 was performed.
  • the external extraction quantum efficiency was expressed as a relative value with the organic EL element 12-1 (comparative example) as 100.
  • Example 2 The same procedure as described in Example 1 was performed. The half life was expressed as a relative value with the organic EL element 12-1 (comparative example) as 100.
  • the organic EL elements 12-3 to 12-14 of the present invention produced using the organic EL element material of the present invention have higher efficiency than the comparative organic EL elements 12-1 and 12-2. It is apparent that the device characteristics are improved, such as an improvement in half-life, a reduction in driving voltage, and suppression of dark spots.
  • the light emission color (also referred to simply as color) of the element is light emission of pure blue to blue green.
  • Example 13 Production of White Light-Emitting Organic EL Element 13-1 >> Patterning was performed on a substrate (NAV-45, manufactured by AvanState Co., Ltd.) in which ITO (indium tin oxide) was formed to a thickness of 100 nm on a glass substrate of 100 mm ⁇ 100 mm ⁇ 1.1 mm as an anode. Thereafter, the transparent support substrate provided with the ITO transparent electrode was subjected to ultrasonic cleaning with isopropyl alcohol, dried with dry nitrogen gas, and UV ozone cleaning was performed for 5 minutes.
  • ITO indium tin oxide
  • a solution obtained by diluting poly (3,4-ethylenedioxythiophene) -polystyrene sulfonate (PEDOT / PSS, Bayer, Baytron P Al 4083) to 70% with pure water is spin-coated. Then, the film was dried at 200 ° C. for 1 hour to provide a first hole transport layer having a thickness of 30 nm.
  • a hole transport material Poly N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl)) benzidine (manufactured by American Dye Source, ADS- The chlorobenzene solution of No. 254) was formed by spin coating. It heat-dried at 150 degreeC for 1 hour, and provided the 2nd hole transport layer with a film thickness of 40 nm.
  • spin coating was performed using a solution of 34 (100 mg), dopant materials D-1 (3 mg), D-6 (3 mg), and A33 (16 mg) in 10 ml of toluene as a host under the conditions of 2000 rpm and 30 seconds.
  • the film was formed by the method.
  • a light emitting layer was formed by vacuum drying at 60 ° C. for 1 hour.
  • This substrate is fixed to a substrate holder of a vacuum deposition apparatus, and the vacuum chamber is depressurized to 4 ⁇ 10 ⁇ 4 Pa. Then, lithium fluoride is deposited to 0.5 nm as a cathode buffer layer and aluminum is further deposited to 110 nm as a cathode to form a cathode. Thus, an organic EL element 13-1 was produced.
  • An organic EL element 13-2 was produced in the same manner as in the production of the organic EL element 13-1, except that the host compound 34 of the light emitting layer was replaced with 1 and the dopant material A33 was replaced with A36.
  • Example 14 Preparation of White Light-Emitting Organic EL Element 14-1 >> Transparent support provided with this ITO transparent electrode after patterning on a substrate (NH45 manufactured by NH Techno Glass Co., Ltd.) formed by depositing 100 nm of ITO (indium tin oxide) on a glass substrate of 100 mm ⁇ 100 mm ⁇ 1.1 mm as an anode The substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • a substrate NH45 manufactured by NH Techno Glass Co., Ltd.
  • ITO indium tin oxide
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum evaporation apparatus, while 200 mg of CuPc is put into a molybdenum resistance heating boat, and 200 mg of ⁇ -NPD is put into another molybdenum resistance heating boat, and another molybdenum resistance heating boat is put into place.
  • 200 mg A2 is put in another molybdenum resistance heating boat
  • 200 mg of D-4 is put in another resistance heating boat made of molybdenum
  • 200 mg of D-6 is put in another resistance heating boat made of molybdenum.
  • 200 mg of ET-29 was placed in a molybdenum resistance heating boat and attached to a vacuum evaporation system.
  • the vacuum chamber was then depressurized to 4 ⁇ 10 ⁇ 4 Pa, heated by energizing the heating boat containing CuPc, and deposited on a transparent support substrate at a deposition rate of 0.1 nm / second to form a 10 nm hole injection layer.
  • the vacuum chamber was then depressurized to 4 ⁇ 10 ⁇ 4 Pa, heated by energizing the heating boat containing CuPc, and deposited on a transparent support substrate at a deposition rate of 0.1 nm / second to form a 10 nm hole injection layer.
  • the heating boat containing ⁇ -NPD was energized and heated, and deposited on the hole injection layer at a deposition rate of 0.1 nm / second to provide a 20 nm hole transport layer.
  • the heating boat containing 2 and A31 was energized and heated, and co-deposited on the hole transport layer at a deposition rate of 0.1 nm / second and 0.012 nm / second, respectively. Provided.
  • the first light-emitting layer is heated by energizing the heating boat containing 2 and D-4 and D-6 at the deposition rates of 0.1 nm / second, 0.012 nm / second, and 0.002 nm / second, respectively.
  • a second light-emitting layer having a thickness of 60 nm was provided by co-evaporation.
  • the heating boat containing ET-29 was energized and heated, and deposited on the second light emitting layer at a deposition rate of 0.1 nm / second to provide a 25 nm electron transport layer.
  • Example 15 (Blue light emitting organic EL device)
  • the organic EL element 12-9 produced in Example 12 was used as a blue light-emitting organic EL element.
  • Green light-emitting organic EL device As a green light emitting organic EL element, a blue light emitting organic EL element 12-9B was prepared in the same manner as in the preparation of the organic EL element 12-9 produced in Example 12, except that A23 was changed to D-1.
  • red light emitting organic EL device As a red light emitting organic EL element, a red light emitting organic EL element 12-9C was produced in the same manner as in the production of the organic EL element 12-9 of Example 12, except that A23 was changed to D-10.
  • FIG. 1 shows a display portion of the produced display device. Only the schematic diagram of A is shown.
  • a wiring portion including a plurality of scanning lines 5 and data lines 6 on the same substrate, and a plurality of juxtaposed pixels 3 (light emission color is a red region pixel, a green region pixel, a blue region pixel, etc.)
  • 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 lattice shape and are connected to the pixels 3 at the 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 as 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.
  • a full color display device was produced by juxtaposing the red, green, and blue pixels appropriately.
  • the organic electroluminescent element material and the organic electroluminescent element of the present invention exhibit high luminous efficiency, long emission lifetime, low drive voltage, and short-wave emission, and are suitable for display devices and various illumination devices. Available.

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Abstract

L'invention concerne un élément électroluminescent organique qui offre une efficacité lumineuse élevée, une longue durée d'émission et une faible tension d'attaque, tout en émettant une lumière à longueur d'onde courte ; un dispositif d'affichage et un dispositif d'éclairage, chacun comprenant cet élément ; et un matériau d'élément électroluminescent organique qui est utilisé pour la formation de l'élément. Cet élément électroluminescent organique comprend au moins une couche électroluminescente entre une électrode positive et une électrode négative et il se caractérise en ce qu'il contient un complexe métallique qui comprend au moins un ligand représenté par la formule générale (A), ledit ligand étant coordonnée à un élément de métal de transition du groupe 8-10 dans le tableau périodique des éléments. Formule générale (A) : A-B
PCT/JP2012/050536 2011-01-17 2012-01-13 Élément électroluminescent organique, dispositif d'affichage, dispositif d'éclairage et matériau d'élément électroluminescent organique Ceased WO2012098996A1 (fr)

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