WO2004111066A1 - Compose de coordination metallique, composition polymere et element electroluminescent organique contenant lesdites substances - Google Patents

Compose de coordination metallique, composition polymere et element electroluminescent organique contenant lesdites substances Download PDF

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WO2004111066A1
WO2004111066A1 PCT/JP2004/008392 JP2004008392W WO2004111066A1 WO 2004111066 A1 WO2004111066 A1 WO 2004111066A1 JP 2004008392 W JP2004008392 W JP 2004008392W WO 2004111066 A1 WO2004111066 A1 WO 2004111066A1
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group
halogen
metal coordination
substituted
coordination compound
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PCT/JP2004/008392
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Japanese (ja)
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Satoyuki Nomura
Yoshii Morishita
Yoshihiro Tsuda
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Hitachi Chemical Co., Ltd.
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Priority to US10/559,774 priority Critical patent/US7955716B2/en
Publication of WO2004111066A1 publication Critical patent/WO2004111066A1/fr

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Definitions

  • the present invention relates to a novel metal coordination compound, a polymer composition, and a fine composition using the same.
  • the present invention relates to an organic electroluminescence (EL) device.
  • electroluminescent devices have attracted attention for large area solid-state light source applications as alternatives to incandescent lamps and gas-filled lamps.
  • it is attracting attention as the leading self-luminous display that can replace the liquid crystal display in the flat panel display (FPD) field.
  • organic electroluminescent (EL) devices which are made of organic materials, are being commercialized as low-power-consumption full-color FPDs.
  • a 1 q 3 Aluminum quinolinol complex (tris (8-quinolinolato) aluminum) ⁇ — NPD: N, -Di-naphthalen-l-yl-N, N'-diphenyl-biphenyl-4, 4'- diamine
  • an object of the present invention is to provide a phosphorescent material which emits light in a wide visible light range from blue to red and has excellent color purity, reliability, and the like in view of the above-described conventional problems. .
  • an object of the present invention is to provide a metal coordination compound having blue phosphorescence with excellent color purity.
  • an object of the present invention is to provide a metal coordination compound which emits light of various colors from green to red and has a long driving life.
  • an object of the present invention is to provide a metal coordination compound having blue phosphorescence having excellent color purity, and to provide a metal coordination compound having phosphorescence having a long driving life from blue to red. It shall be.
  • Another object of the present invention is to provide a polymer composition containing the metal coordination compound.
  • Still another object of the present invention is to provide an organic electroluminescent device using the metal coordination compound or the polymer composition.
  • a metal coordination compound having a cyclic compound represented by formulas (1) to (6) as a ligand emits light in a wide wavelength range from blue to red.
  • the present invention by finding that it is a phosphorescent material with excellent properties I came to. That is, the present invention relates to a compound represented by any of formulas (1) and (6).
  • XJ XB and R are each independently R — ⁇ R 2 , SR 3 , — ⁇ C ⁇ R 4 , _C ⁇ R 5 , one Si R 6 R 7 R 8 , and one NR 9 R 10 (however, a length of 1 to!
  • ⁇ 13 is a hydrogen atom, a halogen atom, a cyano group , Nitro group, carbon number 1-2 Two straight-chain, cyclic or branched alkyl groups or a halogen-substituted alkyl group in which part or all of the hydrogen atoms have been substituted with halogen atoms, an aryl group having 6 to 21 carbon atoms, a carbon number of 2 to 2 A heteroaryl group of 20 or an aralkyl group having 7 to 21 carbon atoms or a halogen-substituted aryl group, a halogen-substituted heteroaryl group or a halogen-substituted aralkyl group in which part or all of the hydrogen atoms have been replaced by halogen atoms.
  • a substituent selected from the group of, also, X I through X 6 is independently selected from groups a same ring A the same groups defined X t to X 6 It may have a substituent.
  • 1 ⁇ to 11 may have a substituent, and examples of the substituent include a halogen atom, a cyano group, an aldehyde group, an amino group, an alkyl group, an alkoxy group, an alkylthio group, and a carboxyl group. And a sulfonic acid group, a nitro group, etc. These substituents may be further substituted with a halogen atom, a methyl group, or the like.
  • a metal coordination compound having a carbazole derivative as a ligand is an excellent phosphorescent material having blue phosphorescence with excellent color purity. I found it. Therefore, as a preferred embodiment of the present invention, there is provided a metal coordination compound represented by any one of the following formulas I (1) to 1 (6).
  • Ring A is a cyclic compound containing a nitrogen atom bound to M.
  • a metal coordination compound in which various substituents have been introduced into a ligand as a ligand has a luminescent color ranging from green to red, and has a long drive life. It has been found that it is a long and excellent phosphorescent material.
  • a metal coordination compound represented by any of the following formulas II (1) to (6).
  • M is Ir, h, Ru, ⁇ s, Pd or Pt, and n is 2 or 3.
  • M is Ir, Rh, Ru or ⁇ s and n is 2 In this case, M is further bound to another bidentate ligand Ring A is a cyclization containing a nitrogen atom bonded to M It is a compound.
  • Xi ⁇ X 7 is independently - H, - ⁇ _H, -R 1, -OR 2, one
  • NR ⁇ R 11 (where 1 to! ⁇ 1 is a straight-chain, cyclic or branched alkyl group having 1 to 22 carbon atoms, an aryl group having 6 to 21 carbon atoms, and 2 to 20 carbon atoms) Represents an aralkyl group having 7 to 21 carbon atoms, and each of R 1 to shaku 11 may be the same or different.)
  • Ri R 11 may have a substituent, and examples of the substituent include a halogen atom, a cyano group, an aldehyde group, an amino group, an alkyl group, an alkoxy group, an alkylthio group, a lipoxyl group, Examples thereof include a sulfonic acid group and a nitrile group. These substituents may be further substituted by a halogen atom, a methyl group, or the like.
  • a metal coordination compound having a cyclic compound represented by formulas III (1) to ⁇ (6) as a ligand can emit phosphorescent light from blue to red having excellent color purity. It has been found that this is an excellent phosphorescent material having a long driving life.
  • a metal coordination compound represented by any of the following formulas III (1) to (6).
  • Ring A is a cyclic compound containing a nitrogen atom bonded to M.
  • X 1 to X 6 and R are each independently — R 1 -OR 2 , — SR 3 , _ ⁇ COR 4 , one C ⁇ R 5 , one Si R 6 R 7 R 8 , and one NR 9 R 10 (where 1 to!
  • ⁇ are a hydrogen atom, a halogen atom, a cyano group A nitro group, a linear, cyclic or branched alkyl group having 1 to 22 carbon atoms or a halogen-substituted alkyl group in which part or all of the hydrogen atoms have been substituted with halogen atoms, a carbon atom having 6 to 21 carbon atoms Aralkyl group having 2 to 20 carbon atoms or aralkyl group having 7 to 21 carbon atoms, or a halogen-substituted aryl group in which part or all of the hydrogen atoms have been replaced with halogen atoms, a halogen-substituted heteroaryl group And a halogen-substituted aralkyl group, and 1 ⁇ to 11 () may be the same or different.
  • a substituent selected from the group consisting of, also, Xi Xe may be different even in the same ring A have the same substituent groups as defined in Xi ⁇ X 6 It may be.
  • scale 1 ⁇ ! ⁇ 1. May have a substituent, and examples of the substituent include a halogen atom, a cyano group, an aldehyde group, an amino group, an alkyl group, an alkoxy group, an alkylthio group, a lipoxyl group, a sulfonic acid group, and a nitro group. Can be mentioned. These substituents may be further substituted by a halogen atom, a methyl group or the like. '
  • the present invention also relates to a polymer composition obtained by mixing or copolymerizing the metal coordination compound with a conjugated or non-conjugated polymer.
  • the present invention also relates to an organic electroluminescent device manufactured using the metal coordination compound or the polymer composition.
  • the metal coordination compound of the present invention is represented by the following formulas (1) to (6).
  • M is Ir, Rh, Ru, Os, Pd or Pt, and n is 2 or 3.
  • M further binds another bidentate ligand Ring A is a cyclic compound containing a nitrogen atom bonded to M.
  • Xi Xe and R each independently represent one R 1 , — OR 2 , _SR 3 , — ⁇ COR 4 , one C ⁇ OR 5 , one Si R 6 R 7 R 8 , and one NR 9 R 10 (where 1 ⁇ to 1 ⁇ 1 () is a hydrogen atom, a halogen atom, a cyano group A nitro group, a linear, cyclic or branched alkyl group having 1 to 22 carbon atoms, or a halogen-substituted alkyl group in which part or all of the hydrogen atoms have been substituted with halogen atoms, a carbon atom having 6 to 21 carbon atoms.
  • Aralkyl groups having 2 to 20 carbon atoms or aralkyl groups having 7 to 21 carbon atoms, or halogen-substituted araryl groups in which some or all of the hydrogen atoms thereof have been replaced by halogen atoms; heteroaryl group halogen substituted, a halogen-substituted Ararukiru group, scale 1 ⁇ ! ⁇ 1 15 may each be the same or different.
  • X i X e may be the same or different, and ring A is the same substituent as the group defined by X i to X 6 It may have a group.
  • 1 ⁇ to 11 may have a substituent, and examples of the substituent include a halogen atom, a cyano group, an aldehyde group, an amino group, an alkyl group, an alkoxy group, an alkylthio group, Examples include a ropoxyl group, a sulfonic group, a nitro group, etc. These substituents may be further substituted by a halogen atom, a methyl group, or the like.
  • R 1 examples include a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a halogen atom such as an iodine atom, a cyano group, a nitro group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a cyclopropyl group, and a butyl group.
  • OR 2 represents a hydroxyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, tert- butoxy group, Okuchiruokishi group, tert- Okuchiru Okishi group, phenoxy group, 4-tert- Buchirufuenokishi group, 1 one-naphthyl Okishi Group, 2-naphthyloxy group and 9-anthryloxy group.
  • SR 3 examples include mercapto group, methylthio group, ethylthio group, tert-butylthio group, hexylthio group, octylthio group, phenylthio group, 2-methylphenylthio group, and 4_tert-butylphenylthio group. be able to.
  • Examples of OCOR 4 include a formyloxy group, an acetoxy group, and a benzoyloxy group.
  • COOR 5 examples include a carbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a tert-butoxycarbonyl group, a phenoxycarbonyl group, and a naphthyloxycarbonyl group.
  • S i R 6 R 7 R 8 can be mentioned silyl group, a trimethylsilyl group, Toryechi Rushiriru group, a triphenyl silyl group.
  • NR 9 R 1 examples include amino, N-methylamino, N-ethylamino, N, N-dimethylamino, N, N-ethylamino, N, N-diisopropylamino, N , N-dibutylamino group, N-benzylamino group, N, N-dibenzylamino group, N-phenylamino group, N, N-diphenylamino group and the like.
  • the metal coordination compound of the present invention has phosphorescent emission, and the lowest excited state is considered to be a triplet MLCT (Metal-to-Ligand charge transfer) excited state or a ⁇ -excited state. . When transitioning from these states to the ground state Phosphorescence occurs.
  • MLCT Metal-to-Ligand charge transfer
  • the phosphorescent quantum yield of the light emitting material of the present invention was as high as 0.1 to 0.9, and the phosphorescence lifetime was 1 to 60 s.
  • the short phosphorescence lifetime is a condition for increasing the luminous efficiency of an organic EL device. In other words, if the phosphorescence lifetime is long, the proportion of molecules in the excited triplet state increases, and at high current densities, the luminous efficiency is reduced based on the 1 ⁇ annihilation.
  • the metal coordination compound of the present invention is a material suitable for a luminescent material of an organic EL device because it has a high phosphorescent efficiency and a short luminescent life.
  • the ring ⁇ ⁇ ⁇ is preferably any one of the cyclic compounds having a structure shown below, and more preferably X i X e (hereinafter, X i X e , May be collectively referred to as a substituent X n.), which may have the same substituent as the group defined in —pyridine, quinoline, benzoxazole, benzothiazol, benzimidazole, benzotriazole, It is imidazole, pyrazole, oxazole, thiazole, triazole, benzopyrazole, triazine or isoquinoline.
  • Zi Ze is the same substituent as the substituent represented as Xn in formulas (1) to (6), and Zi Ze may be the same or different.
  • M is preferably Ir.
  • the other ligand that binds to the metal M may be any of the compounds having the structures shown below. preferable.
  • the metal coordination compound of the present invention can be produced by various synthetic methods known to those skilled in the art. For example, the method described in S. Lamansky et al., J. Am. Chem. Soc. 2001.123. Can be used. An example (in the case where ring A is substituted pyridine) of a synthesis route of the metal coordination compound represented by the above formulas (1) to (6) used in the present invention will be described by taking an iridium coordination compound as an example. Note that the explanations here relate to (2) shown in Table I-11, (2) shown in Table II-1, and (2) shown in Table III-1. The exemplified compounds can be synthesized by almost the same method. (Synthesis of ligand L)
  • the lowest excited state A high level of energy is required. However, it is considered that the emission level of the metal coordination compound has changed from blue-green to red because the energy level of the lowest excited state was low for blue light emission.
  • the present inventors have conducted various studies and found that the metal coordination compounds represented by the following formulas I (1) to 1 (6) have blue phosphorescence.
  • Halogen-substituted alkyl groups partially or wholly substituted with halogen atoms, aryl groups having 6 to 21 carbon atoms, heteroaryl groups having 2 to 20 carbon atoms, or aralkyls having 7 to 21 carbon atoms A halogen-substituted aryl group, a halogen-substituted heteroaryl group, or a halogen-substituted aralkyl group, in which some or all of the hydrogen atoms of these groups are substituted with a halogen atom;
  • To X 7 may be the same or different, and ring A may have the same substituent as the group defined for X i to X 7 . )
  • ring A is preferably either a cyclic compound having the structure shown below, X I through X 7 (hereinafter, Pyridine, quinoline, benzoxazole, benzothiazole, benzimidazole, benzotriazole, imidazole, pyrazole which may have the same substituent as the group defined in).
  • Oxazole, thiazole, triazole, benzopyrazole or triazine more preferably pyridine or quinoline which may have the same substituent as the group defined by Xn.
  • Zi ⁇ Z 6 are the same substituents as the substituent represented as Xn of formula I (1) ⁇ I (6 ), Z Ze may or may not be the same.
  • the other ligand that binds to the metal M may be any of the compounds having the structures shown below. preferable.
  • Y to Y 4 are the same substituents represented as Xn of formula I (1) ⁇ 1 (6) , Yi ⁇ Y 4 may be different even in the same.
  • At least one of the substituents Xn, or at least one of the substituents defined in the same manner as Xn included in ring A, has a shorter emission wavelength.
  • it is preferably a halogen atom, a cyano group or a halogen-substituted alkyl group, more preferably a fluorine atom, a chlorine atom, a cyano group or a trifluoromethyl group, and It is more preferably an orthomethyl group, and most preferably a fluorine atom.
  • the other Xn is often a hydrogen atom, May be a substituent of
  • X 7 is preferably an alkyl group or a halogen-substituted alkyl group.
  • the metal coordination compounds represented by the formulas I (1) to 1 (6) are expected to have a high energy level in the lowest excited state, and are suitable as a blue phosphorescent material for organic EL.
  • the present inventors have conducted various studies and found that the metal coordination compounds represented by the following formulas II (1) to 11 (6) have phosphorescence emission from green to red and have a long driving life. It has been found to be a phosphorescent material.
  • M is Ir, Rh, Ru, ⁇ s, Pd or Pt, and n is 2 or 3.
  • M is Ir, Rh, Ru or ⁇ s and n is 2
  • another bidentate ligand is bonded to M.
  • Ring A is a cyclic compound containing a nitrogen atom bonded to M.
  • Xi to X 7 are each independently —H, -OH, — R 1 -OR 2 , one SR 3 , one OC ⁇ R 4 , one CO ⁇ R 5 , one Si R 6 R 7 R 8 , one NH 2 , one NHR 9 , and one NR ⁇ R 11 (where 1 ⁇ !
  • ⁇ 11 is a linear, cyclic or branched alkyl group having 1 to 22 carbon atoms, an aryl group having 6 to 21 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, or 7 to Represents an aralkyl group of 21 and R 1 to 11 may be the same or different.
  • Xi X is the same or different Ring A is the same as the group defined by Xi X? May have the following substituents.
  • ⁇ To shaku 11 may have a substituent, and examples of the substituent include a halogen atom, a cyano group, an aldehyde group, an amino group, an alkyl group, an alkoxy group, an alkylthio group, a lipoxyl group, and a sulfonic acid group. And nitro groups. These substituents may be further substituted by a halogen atom, a 'methyl group or the like.
  • ring A is preferably any one of the cyclic compounds having the structures shown below, and Xe to r (hereinafter, referred to as Xe to r ).
  • Xe to r Xe to r
  • Zi Ze is the same substituent as the substituent represented by Xn in formulas II (1) to (6), and Z 1 to Z 6 may be the same or different.
  • the other ligand that binds to the metal M may be any of the compounds having the structures shown below. preferable.
  • Yi ⁇ Y 4 are the same substituents as the substituent represented as Xn of the formula II (1) ⁇ 11 (6) , Y 1 ⁇ Y 4 may or may not be the same.
  • At least one of the substituents X ⁇ or at least one of the substituents defined similarly to Xn of the ring ⁇ ⁇ is green to red. From the viewpoint of easy control of the emission color of, it is preferable to be 1 R, 1 OR or 1 SR.
  • the other Xn is often a hydrogen atom, It may be another substituent.
  • X 7 is preferably an alkyl group, an aryl group or a heteroaryl group.
  • the metal coordination compound represented by the formulas II (1) to 11 (6) the metal coordination compound represented by the formula II (1) or II (4) from the viewpoint of easy synthesis Force S preferred.
  • the metal coordination compounds represented by the above formulas II (1) to 11 (6) have various substituents. 35
  • the energy level of the lowest excited state changes, making it suitable as an organic EL light emitting material that emits green to red light.
  • the present inventors have conducted various studies, and found that the metal coordination compounds represented by the following formulas III (1) to III (6) emit phosphorescence from blue to red and have a long driving life. It has been found that it becomes a light emitting material.
  • X Xe and R are each independently — R 1 , -OR 2 , One SR 3 , one C ⁇ R 4 , one C ⁇ R 5 , one Si R 6 R 7 R 8 , and one NR 9 R 10 (however,! ⁇ 1 ⁇ !
  • ⁇ 1 is a hydrogen atom, halogen Atom, cyano group, nitro group, straight-chain, cyclic or branched alkyl group having 1 to 22 carbon atoms or a halogen-substituted alkyl group in which part or all of the hydrogen atoms have been substituted with halogen atoms, carbon number 6-21 47
  • Aralkyl group having 2 to 20 carbon atoms or aralkyl group having 7 to 21 carbon atoms, or a halogen-substituted aryl group in which part or all of the hydrogen atoms thereof have been replaced with halogen atoms, a halogen-substituted heteroaryl group group, a halogen-substituted Ararukiru radical, R E ⁇ 1 Q may each be the same or different.
  • Xi Xe may be the same or different, and ring A has the same substituent as the group defined by Xi Xe May be. ) Where 1 ⁇ ! ⁇ 1 .
  • substituents May have a substituent, and examples of the substituent include a halogen atom, a cyano group, an aldehyde group, an amino group, an alkyl group, an alkoxy group, an alkylthio group, a lipoxyl group, a sulfonic acid group, and a nitro group. Can be mentioned. These substituents may be further substituted by a halogen atom, a methyl group or the like. .
  • ring A is preferably either a cyclic compound having the structure shown below, X i to X 6 (hereinafter, The pyridine, quinoline, benzoxazole, benzothiazole, benzimidazole, benzotriazol, imidazole, and pyrazole which may have the same substituent as the group defined in) are collectively denoted as Xn. , Oxazole, thiazole, triazole, benzopyrazole, triazine or isoquinoline, and pyridine, quinoline or isoquinoline which may have a substituent similar to the group defined by Xn Is more preferred. 48
  • Zi Ze is the same substituent as the substituent represented as X ⁇ in Formulas III (1) to ⁇ (6), and Zi to Z ⁇ may be the same or different.
  • the other ligand bonded to the metal M is preferably any of the compounds having the structures shown below.
  • ⁇ ⁇ 4 are the same substituents as the substituent represented as Xn of the formula III (1) ⁇ III (6) , Yi ⁇ Y 4 may be different even in the same.
  • ⁇ or at least one of the substituents defined in the same manner as Xn of the ring ⁇ ⁇ ⁇ is preferably an octogen atom, a cyano group or a halogen-substituted alkyl group from the viewpoint of obtaining a blue emission color. It is more preferably a fluorine atom, a chlorine atom, a cyano group or a trifluoromethyl group, further preferably a fluorine atom or a trifluoromethyl group, and most preferably a fluorine atom.
  • —R, —OR, or —SR is preferable.
  • the other Xn is often a hydrogen atom, It may be a substituent.
  • the metal coordination compound is represented by the formula III (2) or III (5).
  • the metal coordination compounds represented by the above formulas III (1) to ⁇ (6) change the energy level of the lowest excited state by changing the substituent variously, and are used as a light emitting material of an organic EL having blue to red emission. Are suitable.
  • metal coordination compounds represented by the formulas III (1) to (6) are shown below, but are not limited thereto.
  • Table ⁇ in one 1 Xi ⁇ X 4 represents a substituent of the ring Alpha.
  • the metal coordination compound of the present invention can be used as a material for an active layer of an electroluminescence device.
  • Active layer means that the layer is capable of emitting light upon application of an electric field (light emitting layer) or that improves charge injection or charge transfer (charge injection layer or charge transfer layer).
  • charge refers to negative or positive charge.
  • the thickness of the active layer is preferably from 10 to 100 nm, more preferably from 20 to 60 nm, and still more preferably from 20 to 40 nm.
  • the metal coordination compound of the present invention may be used as a mixture with other materials.
  • the electroluminescent device using the metal coordination compound of the present invention may be made of a material other than the above metal coordination compound.
  • the material to be mixed may be a high-molecular material or a low-molecular material.
  • Materials that can be used for hole injection and / or hole transport materials include arylamine derivatives, triphenylmethane derivatives, stilbene compounds, hydrazone compounds, carbazole compounds, high molecular weight arylamine, polyaniline, polythiophene, etc. And materials obtained by polymerizing them.
  • Those that can be used for electron injection and Z or electron transfer materials include oxaziazole derivatives, benzoxazole derivatives, benzoquinone derivatives, quinoline derivatives, quinoxaline derivatives, thiadiazol derivatives, benzodiazole derivatives, triazole derivatives, and metal chelate complexes. Materials such as compounds and the like and materials obtained by polymerizing them are exemplified.
  • Materials that can be used for the light emitting material include arylamine derivatives, oxaziazole derivatives, perylene derivatives, quinacridone derivatives, pyrazoline derivatives, anthracene derivatives, rubrene derivatives, stilbene derivatives, coumarin derivatives, naphthylene derivatives, and metal chelates.
  • Materials such as complexes, metal complexes containing central metals such as Ir and Pt, and materials obtained by polymerizing them, polymer materials such as polyfluorene derivatives, polyphenylenevinylene derivatives, polyphenylene derivatives, and polythiophene derivatives Is exemplified.
  • Any binder can be used as long as it does not significantly reduce the properties.
  • the binder polymer include materials such as polystyrene, polycarbonate, polyarylether, polyacrylate, polymethacrylate, and polysiloxane.
  • An organic electroluminescent device can be manufactured using a low-molecular material outside.
  • the low molecular weight material examples include CBP (4, 4'-N, N'-dicarbazole-biphenyl), CDBP (2, 2'-dimethyl-4, 4'-N, '-dicarbazol e-biphenyl) , M CP (m-dicarbazole-benzene) and the like.
  • the mixing ratio of the low-molecular material and the metal coordination compound is preferably 1 to 15% by weight, more preferably 2 to 10% by weight, and still more preferably 3 to 5% by weight of the low-molecular material. It is 8% by weight. If the concentration of the metal coordination compound is too low, the luminous efficiency tends to decrease. If it is too high, the concentration quenching occurs due to the interaction between the metal coordination compounds, and the luminous efficiency tends to decrease.
  • an organic electroluminescence device can be manufactured using the above-mentioned metal coordination compound and a polymer composition containing a conjugated and / or non-conjugated polymer.
  • the polymer composition is a composition obtained by mixing the above-mentioned metal coordination compound with a conjugated or Z- or non-conjugated polymer, or a conjugated and / or non-conjugated with the above-mentioned metal coordination compound.
  • conjugated and Z or non-conjugated polymers include, as a main skeleton, a structure of polyfluorene, polyphenylene, poly (phenylenevinylene), polythiophene, polyquinoline, polyaniline, polyvinylcarbazole, or a derivative thereof.
  • ⁇ ⁇ ⁇ ⁇ -containing polymer as a unit (that is, not only the structure in the main skeleton, but also the side chain structure), benzene, naphthalene, anthracene, phenanthrene, chrysene, rubrene, pyrene, perylene, indene, Azulene, adamantane, fluorene, fluorenone, dibenzofuran, kytrazole, dibenzothiophene, furan, pyrrole, pyrroline, pyrrolidine, thiophene, dioxolan, pyrazole, pyrazoline, pyrazolidine, imi
  • the mixing or copolymerization ratio of the polymer and the metal coordination compound is preferably from 0.1 to 20 parts by weight of the polymer to 100 parts by weight.
  • Solvents used in the polymer composition include chloroform form, methylene chloride, dichloroethane, tetrahydrofuran, toluene, xylene, mesitylene, anisol, acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, ethyl acetate solvent acetate, and the like. Can be used.
  • the metal coordination compound or the polymer composition of the present invention as an active layer material of an electroluminescence device, a method known to those skilled in the art, for example, vacuum evaporation, inkjet, casting, dipping, printing or This can be achieved by laminating a thin film on a substrate using spin coating or the like.
  • Printing methods include letterpress printing, intaglio printing, offset printing, lithographic printing, letterpress reversal offset printing, screen printing, and gravure printing.
  • Such a lamination method can usually be carried out in a temperature range of 120 to 130, preferably 10 to 100, particularly preferably 15 to 50 ° C.
  • drying of the laminated polymer solution can be usually performed by drying at room temperature or by heating and drying using a hot plate. 70
  • Electroluminescent devices typically include an electroluminescent layer (light-emitting layer) between a force source and an anode, where at least one of the electrodes is transparent.
  • one or more electron injection layers and Z or electron transfer layers can be inserted between the electroluminescent layer (light emitting layer) and the force sword, and one or more hole injection layers.
  • a layer and a hole or hole transport layer can be inserted between the electroluminescent layer (light emitting layer) and the anode.
  • the force sword material is preferably, for example, a metal or metal alloy such as Li, Ca, Mg, A1, In, Cs, Mg / Ag, and LiF.
  • a metal for example, Au
  • another material having metal conductivity for example, an oxide (for example, ITO: indium tin oxide)
  • a transparent substrate for example, glass or a transparent polymer.
  • the electron injection and Z or electron transfer layer include a layer containing a material such as an oxaziazole derivative, a benzoxazole derivative, a benzoquinone derivative, a quinoline derivative, a quinoxaline derivative, a thiadiazole derivative, a benzodiazole derivative, a triazole derivative, or a metal chelate complex compound.
  • a material such as an oxaziazole derivative, a benzoxazole derivative, a benzoquinone derivative, a quinoline derivative, a quinoxaline derivative, a thiadiazole derivative, a benzodiazole derivative, a triazole derivative, or a metal chelate complex compound.
  • copper phthalocyanine for hole injection and Z or hole transport layer, copper phthalocyanine, triphenylamine derivative, triphenylmethane derivative, stilbene compound, hydrazone compound, carbazole compound, high molecular weight arylamine, polyaniline, polythiophene, And the like.
  • the metal coordination compound of the present invention is suitable, for example, as a material for an organic EL device having various emission wavelengths and excellent in reliability, emission characteristics, and the like.
  • the metal coordination compounds represented by the formulas I (1) to 1 (6) are effective for shortening the emission wavelength
  • the metal coordination compounds represented by the formulas II (1) to 11 (6) The compounds are effective in extending the lifetime of the device
  • the metal coordination compounds represented by the formulas III (1) to III (6) are effective in shortening the emission color and extending the lifetime of the device.
  • a THF solution of 3-bromo-9-methylcarbazole (3 Ommo 1) was gradually added to a THF mixture of magnesium (1.9 g, 8 Ommo 1) under a stream of argon with good stirring, and the Grignard reagent was added.
  • the resulting Darynal reagent was gradually added dropwise to a THF solution of trimethyl borate ester (30 Ommo 1) at 178 ° C over 2 hours while being stirred well, and then stirred at room temperature for 2 days.
  • the reaction mixture was poured into 5% dilute sulfuric acid containing crushed ice and stirred.
  • the obtained aqueous solution was extracted with toluene, and the extract was concentrated to give a colorless solid.
  • the solid obtained was recrystallized from toluene / acetone (1 ⁇ 2) to give the borazole derivative boronic acid as colorless crystals (40%).
  • the obtained carpazole derivative boronic acid (12 mmo 1) and 1,2-ethanediol (3 Ommo 1) were refluxed in toluene for 10 hours, and then recrystallized from toluene / acetone (1Z4).
  • the rubazole derivative boron ester was obtained as colorless crystals.
  • the precipitate was purified by silica gel column chromatography (eluent: Black hole Holm / main evening Nord: 30Z1) to give bis [3- (2 'single-pyridyl) one 9-methyl carbazole Ichiru - lambda ⁇ ', C 2 1 (Acetylacetonato) A pale yellow powder of iridium (III) was obtained.
  • the reaction product was cooled to room temperature, poured into 350 ml of 1N hydrochloric acid, and the precipitate was collected by filtration, washed with water, and dried under reduced pressure at 100 ° C for 5 hours.
  • the precipitate was purified black port Holm in eluent and the silica force gel column chromatography, tris [3- (2 'single-pyridyl) Single 9 Mechirukarubazo Ichiru - lambda ⁇ ', C 2 1 iridium (III) A pale yellow powder was obtained.
  • Example I-12 the synthesis was performed in the same manner as in Example I-11 and Example I-12 except that the starting materials such as the sorbazole unit, ring A, and other ligands were changed. Various metal complex compounds were synthesized.
  • Example I-12 Using the compound obtained in Example I-12, an organic EL device having three organic layers was produced, and the device characteristics were evaluated.
  • Example I TO and (indium tin oxide) glass substrate was patterned into a 2mm width, an NPD shed as a hole transport layer by a vacuum evaporation method by resistance heating in a vacuum chamber within one 10_ 5 P a, thickness 40 nm was formed. Further, the metal coordination compound of Example I-2 was co-deposited with CBP at a weight ratio of 5% (film thickness: 30 nm). Further, 30 nm of A 1 Q 3 was deposited as an electron transport layer. On this, as a cathode electrode layer, LiF is 0.5 to 2 nm and A1 is 100 to 150 nm.
  • the characteristics of the organic EL device were measured at room temperature, the current-voltage characteristics were measured with a micro-ammeter 4140 B manufactured by Hewlett-Packard Company, and the emission luminance was measured with SR-3 manufactured by Topcon.
  • SR-3 manufactured by Topcon.
  • the luminance half-life when driven at a constant current (50 mAZcm 2 ) was 100 hours.
  • An organic EL device was fabricated in the same manner as in Examples 1 to 10, except that Ir (ppy) 3 was used instead of the metal coordination compound used in Example I-10.
  • Ir (ppy) 3 was used instead of the metal coordination compound used in Example I-10.
  • the reaction product was cooled to room temperature, poured into 35 Nm of 1N-hydrochloric acid, and the precipitate was collected by filtration, washed with water, and dried under reduced pressure at 100 ° C for 5 hours.
  • the precipitate was purified by silica gel column chromatography using chloroform as eluent, and the pale yellow color of tris [2-hydroxy-6- (2′-pyridyl) -19-methylcarbazo-l- ⁇ ⁇ ', OH iridium (III) A powder was obtained.
  • Examples II-11 and II-12 As shown in Table II-12 below, the synthesis method of Examples II-11 and II-12 was used except that the starting materials such as the sorbazole unit, ring A, and other ligands were changed. Various metal complex compounds were synthesized.
  • Example 11 Using the compound obtained in 1-2, an organic EL device having three organic layers was fabricated.
  • the luminance half-life measured at a constant current (50 mA / cm 2 ) was 200 hours.
  • a Grignard reagent was prepared by gradually adding a THF solution of 2-bromo-9-fluorenone (3 Ommo 1) to a THF mixture of magnesium (1.9 g, 8 Ommo 1) while stirring well under a stream of argon. .
  • the obtained Grignard reagent was gradually added dropwise to a THF solution of trimethyl borate ester (30 Ommo 1) over 2 hours while stirring well at ⁇ 78 ° C., followed by stirring at room temperature for 2 days.
  • the reaction mixture was poured into 5% dilute sulfuric acid containing crushed ice and stirred.
  • the obtained aqueous solution was extracted with toluene, and the extract was concentrated to give a colorless solid.
  • the precipitate was purified by silica gel column chromatography (eluent: formaldehyde methanol: 30/1), and bis [2- (2, -pyridyl) -19-fluorenone-N 1 ', C 3 ] (acetyl (Acetonato) A pale yellow powder of iridium (III) was obtained.
  • Example III-1 a method similar to that of the synthesis method of Example III-1 and Example III-2 was used, as shown in Table III-12 below.
  • Various metal complex compounds were synthesized. ' 87
  • Example III-12 Using the compound obtained in Example III-12, an organic EL device having three organic layers was produced, and the device characteristics were evaluated.
  • I TO and (indium tin oxide) glass substrate was patterned into a 2mm width, a a- NPD as a hole transport layer by a vacuum evaporation method by resistance heating in a vacuum chamber within one 10- 5 P a, film A thickness of 40 nm was formed. Further, the metal coordination compound of Example III-2 was co-deposited with CBP at a weight ratio of 5% (thickness: 30 nm). Further, 30 nm of Al Q 3 was deposited as an electron transport layer. On this, as a cathode electrode layer, LiF was 0.5 to 2 nm and Al was 100 to 150 nm.
  • the luminance half-life measured at a constant current (50 mA / cm 2 ) was 200 hours.

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Abstract

Composé de coordination métallique caractérisé en ce qu'il est représenté par l'une des formules (1) à (6) dans lesquelles B représente >NR, >O, >S, >C=O, >SO2 ou >CR2, M représente Ir, Rh, Ru, Os, Pd ou Pt et n vaut 2 ou 3. Lorsque M représente Ir, Rh, Ru ou Os et que n vaut 2, M est en outre lié à un autre ligand bidenté. Le noyau A est un groupe cyclique contenant un atome d'azote lié à M. La présente invention concerne également une matière émettant de la phosphorescence qui émet une lumière dans une large plage visible de bleu à rouge, avec une grande pureté de couleur, ladite matière étant en outre fiable.
PCT/JP2004/008392 2003-06-09 2004-06-09 Compose de coordination metallique, composition polymere et element electroluminescent organique contenant lesdites substances WO2004111066A1 (fr)

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