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  • H10K50/00—Organic light-emitting devices
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  • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

• R P1 , R P2 , R P3 , R P4 and R P6 are each independently a hydrogen atom, a halogen atom, an alkyl group, an alkyloxy group, an alkylthio group, an aryl group, an aryloxy group, Arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, acyl group, acyloxy group, carbamoyl group, amide group, acid imide group, imine residue, substituted amino group, substituted silyl group, substituted silyloxy group, substituted silylthio group Group, a substituted silylamino group, a monovalent heterocyclic group, a heteroaryloxy group, a heteroarylthio group, an arylalkenyl group, an arylalkynyl group, a substituted carboxyl group or a cyano group
• R P5 represents
• the alkyl group or aryl group on the phenyl ring side of the ligand As for the substitution position, any of R P1 , R P2 , R P3 and R P4 may be used as long as the coordination of the ligand to the metal atom is not hindered, but R P2 or R P3 is preferable.
• the substitution position on the triazole ring side of the ligand may be any of R P5 and R P6 as long as the coordination to the metal atom of the ligand is not hindered.
• p represents an integer selected from 1 to 10
• q represents an integer selected from 1 to (2p + 1)
• r represents an integer selected from 0 to (2p + 1).
• the metal atom M in the metal complex of the present invention is a metal atom selected from the group consisting of a ruthenium atom, a rhodium atom, a palladium atom, an osmium atom, an iridium atom, and a platinum atom. These metal atoms can cause a spin-orbit interaction in the metal complex and cause an intersystem crossing between the singlet state and the triplet state.
• the metal atom M is preferably an osmium atom, an iridium atom or a platinum atom, more preferably an iridium atom or a platinum atom, and particularly preferably an iridium atom.
• R 0 is a divalent linking group between a ligand and a group represented by R P1 , R P2 , R P3 , R P4 , R P5 and R P6 , and each independently represents the above formula ( L-1), a group represented by the formula (L-2), or a group represented by the formula (L-3).
• the divalent linking group is preferably a group represented by the formula (L-1) or (L-2), and more preferably a group represented by the formula (L-2).
• J representing the number of R 0 as a linking group is 0 or 1, but preferably 0.
• R in the formulas (L-1), (L-2) and (L-3) represents an alkyl group, which may be linear, branched or cyclic, but is linear or branched It is preferable that it is linear.
• the carbon number in the linear alkyl group is usually 1 to 10, preferably 1 to 6, more preferably 1 to 3, and further preferably 1.
• the number of carbon atoms in the branched and cyclic alkyl group is usually 3 to 10, preferably 3 to 6.
• the alkyl group represented by R P1 , R P2 , R P3 , R P4 , R P5 and R P6 may be linear, branched or cyclic.
• the straight-chain alkyl group usually has 1 to 12 carbon atoms, preferably 3 to 10 carbon atoms.
• the number of carbon atoms in the branched and cyclic alkyl group is usually 3 to 12, and preferably 3 to 10.
• the alkyl group may have a substituent, but the carbon number of the substituent is not included in the above carbon number.
• alkyl groups are methyl, ethyl, propyl, iso-propyl, butyl, iso-butyl, tert-butyl, pentyl, hexyl, cyclohexyl, heptyl, octyl.
• the alkyloxy group represented by R P1 , R P2 , R P3 , R P4 , R P5 and R P6 may be linear, branched or cyclic.
• the straight-chain alkyloxy group usually has 1 to 12 carbon atoms, preferably 3 to 10 carbon atoms.
• the carbon number of the branched and cyclic alkyloxy group is usually 3 to 12, and preferably 3 to 10.
• the alkyloxy group may have a substituent, but the number of carbons of the substituent is not included in the above number of carbons.
• alkyloxy groups include methyloxy, ethyloxy, propyloxy, iso-propyloxy, butyloxy, iso-butyloxy, tert-butyloxy, pentyloxy, hexyloxy, cyclohexyl Oxy, heptyloxy, octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, 3,7-dimethyloctyloxy, lauryloxy, trifluoromethyloxy, pentafluoroethyloxy, perfluoro Examples include butyloxy group, perfluorohexyloxy group, perfluorooctyloxy group, methyloxymethyloxy group, 2-methyloxyethyloxy group, pentyloxy group, hexyloxy group, octyloxy group, 2-ethyloxy group. Hexyl group, decyloxy group, 3,7-dimethylmethyl
• alkylthio groups include methylthio, ethylthio, propylthio, iso-propylthio, butylthio, iso-butylthio, tert-butylthio, pentylthio, hexylthio, cyclohexylthio, heptylthio, Octylthio group, 2-ethylhexylthio group, nonylthio group, decylthio group, 3,7-dimethyloctylthio group, laurylthio group, trifluoromethylthio group, pentylthio group, hexylthio group, octylthio group, 2-ethylhexylthio group, A decylthio group and a 3,7-dimethyloctylthio group are preferred.
• C 1 -C 12 alkylphenyl group (“C 1 -C 12 alkyl” means that the alkyl moiety has 1 to 12 carbon atoms, and so on. ), 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, pentafluorophenyl group, C 1 -C 12 alkyloxyphenyl group, C 1 -C 12 Alkylphenyl groups are preferred.
• the aryl group is an atomic group obtained by removing one hydrogen atom from an aromatic hydrocarbon.
• This aromatic hydrocarbon includes a compound having a condensed ring, a compound in which two or more selected from an independent benzene ring and / or a condensed ring are bonded directly or via a vinylene group.
• C 1 -C 12 alkyl is an alkyl having 1 to 12 carbon atoms and is the same as described and exemplified for the alkyl group.
• C 1 -C 12 alkyloxy in the group includes methyloxy, ethyloxy, propyloxy, iso-propyloxy, butyloxy, iso-butyloxy, tert-butyloxy, pentyloxy, hexyloxy, cyclohexyloxy, heptyl Examples include oxy, octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, 3,7-dimethyloctyloxy, lauryloxy and the like.
• C 1 -C 12 alkylphenyl in the above group methylphenyl, ethylphenyl, dimethylphenyl, propylphenyl, mesityl, methylethylphenyl, iso-propylphenyl, butylphenyl, iso-butylphenyl, tert-butylphenyl , Pentylphenyl, isoamylphenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, decylphenyl, dodecylphenyl.
• Pentylphenyl isoamylphenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, decylphenyl, dodecylphenyl.
• the arylalkyloxy group represented by R P1 , R P2 , R P3 , R P4 and R P6 has usually 7 to 60 carbon atoms, preferably 7 to 48 carbon atoms.
• the arylalkyloxy group may have a substituent, but the carbon number of the substituent is not included in the above carbon number. Examples of such arylalkyloxy groups include phenyl-methyloxy groups, phenylethyloxy groups, phenylbutyloxy groups, phenylpentyloxy groups, phenylhexyloxy groups, phenylheptyloxy groups, phenyloctyloxy groups, and the like.
• C 1 -C 12 alkyloxy group C 1 -C 12 alkyloxyphenyl-C 1 -C 12 alkyloxy group, C 1 -C 12 alkylphenyl-C 1 -C 12 alkyloxy group, 1-naphthyl-C 1 -C 12 alkyloxy group, 2-naphthyl-C 1 -C 12 alkyloxy group, C 1 -C 12 alkyloxyphenyl-C 1 -C 12 alkyloxy group, C 1 -C 12 alkylphenyl-C A 1 to C 12 alkyloxy group is preferred.
• the arylalkylthio group represented by R P1 , R P2 , R P3 , R P4 and R P6 has usually 7 to 60 carbon atoms, preferably 7 to 48 carbon atoms.
• the arylalkylthio group may have a substituent, but the carbon number of the substituent is not included in the above carbon number.
• arylalkylthio groups include phenyl-C 1 -C 12 alkylthio groups, C 1 -C 12 alkyloxyphenyl-C 1 -C 12 alkylthio groups, C 1 -C 12 alkylphenyl-C 1 -C 12 alkylthio group, 1-naphthyl-C 1 -C 12 alkylthio group, 2-naphthyl-C 1 -C 12 alkylthio group, C 1 -C 12 alkyloxyphenyl-C 1 -C 12 alkylthio group, C 1 A -C 12 alkylphenyl-C 1 -C 12 alkylthio group is preferred.
• the acyloxy group represented by R P1 , R P2 , R P3 , R P4 and R P6 has usually 2 to 20 carbon atoms, preferably 2 to 18 carbon atoms.
• the acyloxy group may have a substituent, but the carbon number of the substituent is not included in the above carbon number.
• Examples of such acyloxy groups include an acetoxy group, a propionyloxy group, a butyryloxy group, an isobutyryloxy group, a pivaloyloxy group, a benzoyloxy group, a trifluoroacetyloxy group, and a pentafluorobenzoyloxy group.
• the carbamoyl group represented by R P1 , R P2 , R P3 , R P4 and R P6 may have a substituent, and the carbon number including the carbon number of the substituent is usually 1 to 20 , Preferably 2 to 18 (that is, represented by the general formula: NR a R b —CO—, wherein R a and R b each independently represents a hydrogen atom or a substituent).
• Examples of such a carbamoyl group include an aminocarbonyl group, a methylaminocarbonyl group, a dimethylaminocarbonyl group, an ethylaminocarbonyl group, a propylaminocarbonyl group, and a butylaminocarbonyl group.
• the amide group represented by R P1 , R P2 , R P3 , R P4 and R P6 may have a substituent, and the number of carbons including the carbon number of the substituent is usually 1 to 20. , Preferably 2 to 18 (that is, represented by the general formula: R c —CO—NR d —, wherein R c and R d each independently represents a hydrogen atom or a substituent).
• Examples of such amide groups include formamide, acetamide, propioamide, butyroamide, benzamide, trifluoroacetamide, pentafluorobenzamide, diformamide, diacetamide, dipropioamide, dibutyroamide, dibutamide. Examples thereof include a benzamide group, a ditrifluoroacetamide group, and a dipentafluorobenzamide group.
• the acid imide group represented by R P1 , R P2 , R P3 , R P4 and R P6 means a monovalent residue obtained by removing one hydrogen atom bonded to the nitrogen atom from the acid imide. .
• the acid imide group usually has 2 to 60 carbon atoms, preferably 2 to 48 carbon atoms.
• the acid imide group may have a substituent, but the carbon number of the substituent is not included in the above carbon number. Examples of such acid imide groups include groups represented by the following structural formulas. [In the formula, a line extending from a nitrogen atom represents a bond, Me represents a methyl group, Et represents an ethyl group, and n-Pr represents an n-propyl group. The same applies hereinafter. ]
• the imine residue represented by R P1 , R P2 , R P3 , R P4 and R P6 is an imine compound (that is, an organic compound having —N ⁇ C— in the molecule. , Ketimine, and a compound in which a hydrogen atom bonded to a nitrogen atom in these molecules is substituted with an alkyl group or the like.) Means a monovalent residue obtained by removing one hydrogen atom.
• the imine residue usually has 2 to 20 carbon atoms, preferably 2 to 18 carbon atoms.
• the imine residue may have a substituent, but the carbon number of the substituent is not included in the above carbon number. Examples of such an imine residue include groups represented by the following structural formulas.
• one or two hydrogen atoms in the amino group are alkyl groups, aryl groups, arylalkyl groups and monovalent complex groups.
• the alkyl group, aryl group, arylalkyl group and monovalent heterocyclic group may have a substituent, but the carbon number of the substituent is not included in the carbon number of the substituted amino group.
• the carbon number of the substituted amino group is usually 1 to 60, preferably 2 to 48.
• substituted amino groups include methylamino, dimethylamino, ethylamino, diethylamino, propylamino, dipropylamino, iso-propylamino, diisopropylamino, butylamino, iso -Butylamino, tert-butylamino, pentylamino, hexylamino, cyclohexylamino, heptylamino, octylamino, 2-ethylhexylamino, nonylamino, decylamino, 3,7-dimethyloctylamino group, lauryl group, a cyclopentylamino group, dicyclopentylamino group, cyclohexylamino group, dicyclohexylamino group, pyrrolidyl group, piperidyl group, ditrifluoromethylamino group, phenylamino
• 1, 2 or 3 of the hydrogen atoms in the silyl group are alkyl groups, aryl groups, arylalkyl groups and monovalent groups. It means a silyl group substituted with 1, 2 or 3 groups selected from the group consisting of heterocyclic groups.
• the alkyl group, aryl group, arylalkyl group and monovalent heterocyclic group may have a substituent, but the carbon number of the substituent is not included in the carbon number of the substituted silyl group.
• the carbon number of the substituted silyl group is usually 1 to 60, preferably 3 to 48.
• substituted silyl groups include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-iso-propylsilyl, dimethyl-iso-propylsilyl, diethyl-iso-propylsilyl, tert-butyl.
• Silyldimethylsilyl group pentyldimethylsilyl group, hexyldimethylsilyl group, heptyldimethylsilyl group, octyldimethylsilyl group, 2-ethylhexyl-dimethylsilyl group, nonyldimethylsilyl group, decyldimethylsilyl group, 3,7-dimethyloctyl- Dimethylsilyl group, lauryldimethylsilyl group, phenyl-C 1 -C 12 alkylsilyl group, C 1 -C 12 alkyloxyphenyl-C 1 -C 12 alkylsilyl group, C 1 -C 12 alkylphenyl-C 1 -C 12 alkyl Silyl group, 1-naphthyl -C 1 ⁇ C 12 alkylsilyl group, 2-naphthyl -C 1 ⁇ C 12 alkylsilyl group
• substituted silyloxy groups include trimethylsilyloxy group, triethylsilyloxy group, tripropylsilyloxy group, tri-iso-propylsilyloxy group, dimethyl-iso-propylsilyloxy group, diethyl-iso-propylsilyl group Oxy group, tert-butylsilyldimethylsilyloxy group, pentyldimethylsilyloxy group, hexyldimethylsilyloxy group, heptyldimethylsilyloxy group, octyldimethylsilyloxy group, 2-ethylhexyl-dimethylsilyloxy group, nonyldimethylsilyloxy group , decyldimethylsilyl group, a 3,7-- butyldimethylsilyloxy group, lauryl dimethyl silyloxy group, a phenyl -C 1 ⁇ C 12 alkyl sily
• Examples of such substituted silylamino groups include trimethylsilylamino group, triethylsilylamino group, tripropylsilylamino group, tri-iso-propylsilylamino group, dimethyl-iso-propylsilylamino group, diethyl-iso-propylsilyl group.
• the heteroaryloxy group represented by R P1 , R P2 , R P3 , R P4 and R P6 has usually 6 to 60 carbon atoms, preferably 7 to 48 carbon atoms.
• the heteroaryloxy group may have a substituent, but the number of carbons of the substituent is not included in the above number of carbons.
• Examples of such heteroaryloxy groups include thienyloxy groups, C 1 -C 12 alkyloxythienyloxy groups, C 1 -C 12 alkylthienyloxy groups, pyridyloxy groups, C 1 -C 12 alkyloxypyridyloxy groups.
• C 1 -C 12 alkyloxyphenyl-C 2 -C 12 alkynyl group C 1 -C 12 alkylphenyl-C 2 -C 12 alkynyl group, 1-naphthyl-C 2 -C 12 alkynyl group
• Examples include 2 -naphthyl-C 2 -C 12 alkynyl group, and C 1 -C 12 alkyloxyphenyl-C 2 -C 12 alkynyl group and C 1 -C 12 alkylphenyl-C 2 -C 12 alkynyl group are preferable.
• the aromatic heterocyclic compound "HOUBEN-WEYL METHODS OF ORGANIC CHEMISTRY 4 TH EDITION", the E9b winding, one page, GEORG THIEME VERLAG STUTTGART; HOUBEN- WEYL METHODS OF ORGANIC CHEMISTRY 4 TH EDITION, the E9c winding, 667 Page, GEORG THIEME VERLAG STUTTGART, and the like.
• low-molecular compound of the charge transport material include the following compounds.
• an alkyl group, an alkyloxy group, an alkylthio which is a substituent that the P ring, the Q ring, and the 5-membered ring including Y 1 may have.
• R 6 to R 10 , R 13 , R 18 to R 31 and R 34 to R 36 are each independently a hydrogen atom, alkyl group, alkyloxy group, alkylthio group, aryl group, aryloxy group, arylthio group, aryl Alkyl group, arylalkyloxy group, arylalkylthio group, arylalkenyl group, arylalkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, silyloxy group, substituted silyloxy group, monovalent heterocyclic group or halogen atom Represents. )
• an alkyl group, an alkyloxy group, an alkylthio group, an aryl which is a substituent that the 5-membered ring (may be a 6-membered ring) including P ′ ring, Q ′ ring and Y 2 may have.
• acyloxy group aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, arylalkenyl group, arylalkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group,
• the acyloxy group, imine residue, carbamoyl group, amide group, acid imide group, monovalent heterocyclic group, carboxyl group, substituted carboxyl group and cyano group are the groups described and exemplified as the group and atom represented by R. And the same as atoms.
• examples of the divalent aromatic amine residue represented by Ar include a divalent group represented by the following formula (6).
• Ar 6 , Ar 7 , Ar 8 and Ar 9 each independently represent an arylene group or a divalent heterocyclic group.
• Ar 10 , Ar 11 and Ar 12 each independently represents an aryl group or a monovalent heterocyclic group.
• Ar 6 to Ar 12 may have a substituent.
• x and y are each independently 0 or 1.
• an arylene group, a divalent heterocyclic group, an aryl group and a substituent that the monovalent heterocyclic group may have include an alkyl group, an alkyloxy group, an alkylthio group, an aryl group, Aryloxy group, arylthio group, arylalkyl group, arylalkyloxy group, arylalkylthio group, arylalkenyl group, arylalkynyl group, amino group, substituted amino group, silyl group, substituted silyl group, halogen atom, acyl group, acyloxy group , Imine residue, carbamoyl group, amide group, acid imide group, monovalent heterocyclic group, carboxyl group, substituted carboxyl group, cyano group and nitro group.
• substituents are the same as the groups and atoms described and exemplified as the groups and atoms represented by R.
• polymer compound of the charge transport material for example, a polymer compound containing the following group (that is, a group excluding parentheses in the following examples), in particular, a polymer compound containing the following group as a repeating unit: preferable.
• the lowest triplet excitation energy (TH) of the low molecular compound or polymer compound of the charge transport material and the lowest triplet excitation energy (TM) of the metal complex of the present invention are: TH> TM-0.1 (eV) It is preferable to satisfy the relationship TH> TM It is more preferable to satisfy the relationship TH> TM + 0.1 (eV) It is more preferable to satisfy this relationship.
• the anode of the light emitting device of the present invention is an electrode that supplies holes to a hole injection layer, a hole transport layer, a light emitting layer, etc., and it is effective to have a work function of 4.5 eV or more.
• As the material for the anode metals, alloys, metal oxides, electrically conductive compounds, mixtures thereof, and the like can be used.
• the cathode of the light emitting device of the present invention is an electrode that supplies electrons to an electron injection layer, an electron transport layer, a light emitting layer, and the like.
• a material for the cathode a metal, an alloy, a metal halide, a metal oxide, an electrically conductive compound, or a mixture thereof can be used.
• cathode materials include alkali metals (lithium, sodium, potassium, etc.) and their fluorides and oxides, alkaline earth metals (magnesium, calcium, barium, cesium, etc.) and their fluorides and oxides, gold, Silver, lead, aluminum, alloys and mixed metals (sodium-potassium alloy, sodium-potassium mixed metal, lithium-aluminum alloy, lithium-aluminum mixed metal, magnesium-silver alloy, magnesium-silver mixed metal, etc.), rare earth metals ( Indium, ytterbium, etc.).

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