TW201245157A - Metal complex and organic electronic device comprising same - Google Patents

Abstract

Provided is a metal complex represented by the following formula (1): M [L]a[X]b[L']c (1) [wherein, M represents Cerium ion, Praseodymium ion, Ytterbium ion or Lutetium ion, L represents a ligand represented by the following formula (2): (in formula (2), A1, A2, and A3 respectively independently represents a hydrocarbondiyl optionally having a substitute, or a direct bond, L1, L2, and L3 respectively independently represents hydrogen or a ligand. Provided that at least one of L1, L2, and L3 represent a heterocyclic group as a ligand, X represents pair ion, L' represents a monodentate ligand or a bidentate ligand, a is a positive number, b and c respectively independently represents a number equal to or larger than 0, when L, X and L' are plural, they may be the same or different.] relative to the total mass of metal complex, the ratio of the sp3 carbon atom contained in the metal complex is equal to or larger than 22 mass%.

Description

201245157 VI. Description of the Invention: [Technical Field to Be Invented by the Invention] The present invention relates to a metal complex and an organic electron w element containing the metal complex. [Prior Art] As a luminescent material used in the light-emitting layer of the organic electroluminescent element, the ratio of the sp3 carbon atom is 19.6%, and the use of the 4-dentate ligand containing the benzimidazolyl group is wrong. Body (Non-Patent Document 丨). [Prior Art Document] (Non-Patent Document 1): Xiang-Li Zheng, Cheng-Yong Su et al., Angew. Chem. Int. Ed., 46, 7399-7403 (2007) [Summary of the Invention] [Invention to be solved Problem] However, the above-mentioned defective body lacks solubility in a nonpolar solvent, and thus it is difficult to form a film by a coating method. SUMMARY OF THE INVENTION An object of the present invention is to provide a metal complex which is highly soluble in a nonpolar solvent and which is easy to form a film by a coating method. [Means for Solving the Problem] The present inventors have finally completed the present invention as a result of careful study. The first aspect of the present invention provides a metal complex represented by the following composition formula (1): M[L]a[X]b[L, ]〇[In the formula (1), Μ represents cerium ion, cerium ion, cerium Ion or ute (iutetium) ion, 324066 5 (2) (2) 201245157 L represents a ligand represented by the following formula (2):

(In the formula (2), A1, A2 and A3 are each independently, and represent a hydrocarbon diyl group which may have a substituent, or a direct bond, and L1, L2 and L3 are each independently, and represent a hydrogen atom or a coordination group. a group, however, at least one of L1, L2 and L3 is a heterocyclic group which may have a substituent as a ligand), X represents a counterion, and L' represents a ligand of a single tooth or a double tooth, a is a positive number, and b and c are independent, and are numbers above 0. When L, X and L' are plural, these may be the same or different, and the ratio of the sp3 carbon atoms contained in the metal complex is 22% by mass or more based on the total mass of the metal complex. The second aspect of the present invention provides a composition comprising the above metal complex and a charge transporting material. The third aspect of the present invention provides an organic thin film containing the above metal complex and an organic electronic component containing the above metal complex. The fourth aspect of the present invention provides a compound represented by the following formula (5). 324066 6 201245157

η [In the formula (5), R9, R1() and R11 are each independently a hydrogen atom, a hydrocarbon group containing four or more sp3 carbon atoms which may have a substituent, or a group having a substituent of 4 More than one heterocyclic group of the sp3 carbon atom, R12, R13 and R14 are each independently, and represent -0_, -COO-, -S(V, -ΗΡ0Γ, a hydrocarbon group which may have a substituent, a hydrocarbyl group which may have a substituent a heterocyclic group which may have a substituent, a hydroxyl group, a carboxyl group, a sulfo group or a phosphoric acid group (a group represented by -0Ρ(=0)(0Η)2. The same applies hereinafter), R15, R16, R17, R18, R19 and R2° are each independently represented by a hydrogen atom or a substituent, and m, η and p are each independently an integer of 0 to 2. When m is 2, two R12s may be the same or different and may be combined with each other. And forming a ring together with the carbon atoms respectively combined. When η is 2, two R13s may be the same or different, may be combined with each other, and form a ring together with the carbon atoms respectively bonded. When ρ is 2, 2 [[14] may be the same or different, may be combined with each other, and form a ring together with the carbon atoms respectively combined. 324066 7 201245157 [Embodiment [Best Mode for Carrying Out the Invention] The present invention will be described below. In the specification of the present invention, the term "may have a substituent" means that the compound which is described later or the hydrogen atom of the group is unsubstituted, and In the present specification, the term "substituent" is used unless otherwise specified. The following meaning is used. As a substituent bonded to a carbon atom, for example, Examples thereof include a hydrocarbon group, a hydrocarbyloxy group, a thiol group, a heterocyclic group, a halogen atom, a cyano group, a decylamino group, a quinone imine group, an unsubstituted or substituted silyl group, a fluorenyl group, and an oxygen-burning group. Alkyl, alkoxysulfonyl, alkoxyphosphonyl, unsubstituted or substituted phosphino, unsubstituted or substituted phosphinyl, unsubstituted or substituted amine, hydroxy, mercapto , carboxyl group, transverse group, acid-filling group, acid-adding group, nitro group, -NH-, _0, _S, -C0CT, -S (V, -HP〇4, -HP〇3- 〇 are preferably a hydrocarbon group , alkoxy, hydrocarbylthio, heterocyclyl, thiol, diketo, sulfo, and phosphoric acid, more preferably hydrocarbon Examples of the substituent bonded to the nitrogen atom include a hydrocarbon group. When the above substituent is a group containing a carbon atom and does not contain an aromatic ring, the number of carbon atoms is usually from 1 to 30, preferably from 1 to 20, more preferably Preferably, the above substituent is a group containing a carbon atom and containing an aromatic ring, and the number of carbon atoms is usually from 2 to 36, more preferably from 3 to 26, still more preferably from 6 to 16. 324066 8 201245157 Examples of the hydrocarbon group include mercapto, ethyl, propyl, 2-propyl, butyl, 2-butyl, isobutyl, tert-butyl, pentyl, hexyl, octyl, decyl, dodecyl , 2-ethylhexyl, 3,7-didecyloctyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, norbornyl, benzyl, 3, 5 -di-tertiary butylbenzyl, α,didecylbenzyl, phenethyl, 2-phenethyl, vinyl, propenyl, butenyl, oleyl, sesqui Alkenyl (icosapentaenyl), docosahexanyl, 2,2-diphenylvinyl, 1,2,2-tristyryl, 2-phenyl-2-propenyl, phenyl, 2- Phenylphenyl, 4-tolyl, 2-biphenyl 3-biphenyl, 4-biphenyl, polyphenyl, 3, 5-diphenylphenyl, 3,4-diphenylphenyl, pentaphenylphenyl, 4-(2,2-di Phenylvinyl)phenyl, 4-(1,2,2-triphenylvinyl)phenyl, indenyl, naphthyl, 2-naphthyl, 9-fluorenyl, 2-indenyl, 9-phenanthryl , 1-mercapto, chrysenyl, naphthacenyl, and kelang. Desirably: methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, butyl, isobutyl, secondary butyl, decyl, hexyl, octyl, decyl, eleven Anthracyl, 2-ethylhexyl, 3,7-didecyloctyl, a benzyl, 3,5-di-tert-butylbenzyl, α,α-dimethylbenzyl, phenylethyl, 2-phenethyl, vinyl, propenyl, butenyl, phenyl, 2-decylphenyl, 4-tolyl, 4-trifluorodecylphenyl, 4-decyloxyphenyl, 2-linked Phenyl, 3-biphenylyl, 4-biphenylyl, polyphenyl, fluorenyl, 1-naphthyl, and 2-naphthyl. More preferably, mercapto, ethyl, tert-butyl _, 1-propyl, 1-butyl, 2-butyl, isobutyl, tert-butyl, pentyl, hexyl, octyl, fluorene , dodecyl, 2-ethylhexyl, 3,5-di-tert-butylbenzyl, α,α - 324066 9 201245157 dimercaptobenzyl, vinyl, butenyl, phenyl, 2 Further, a tolyl group and a 4-fluorenylphenyl group are more preferably an anthracenyl group, an ethyl group, a 1-propyl group, a hexyl group, a 2-ethylhexyl group, a benzyl group, and a vinyl group. Examples of the alkoxy group include a decyloxy group, an ethoxy group, a propoxy group, a 2-propoxy group, a 1-butoxy group, a 2-butoxy group, an isobutoxy group, and a tertiary butoxy group. , pentyloxy, hexyloxy, octyloxy, decyloxy, dodecyloxy, 2-ethylhexyloxy, 3,7-didecyloctyloxy, cyclopropoxy, cyclopentyloxy , cyclohexyloxy, 1-adamantyloxy, 2-adamantyloxy, norbornyloxy, benzyloxy, α,a-didecylbenzyloxy, 2-phenylethoxy, 1- Phenylethoxy, phenoxy, octylphenoxy, 1-naphthyloxy, and 2-naphthyloxy, preferably: methoxy, ethoxy, 1-propoxy, 2-propenyl Oxyl, 1-butoxy, 2-butoxy, isobutoxy, tert-butoxy, pentyloxy, hexyloxy, octyloxy, decyloxy, dodecyloxy, 2- Ethylhexyloxy and 3,7-diindenyloctyloxy are more preferred: methoxy, ethoxy, and 1-propoxy. Examples of the hydrocarbonthio group include a thiol group, an ethylthio group, a 1-propylthio group, a 2-propylthio group, a 1-butylthio group, a 2-butylthio group, an isobutylthio group, and a tertiary butyl sulfide. Base, pentylthio, hexylthio, octylthio, decylthio, dodecylthio, 2-ethylhexylthio, 3,7-didecyloctylthio, cyclopropylthio, cyclopentyl Sulfur, cyclohexylthio, 1-adamantanethio, 2-adamantanethio, thiolthio, benzylthio, α,α-dimercaptobenzylthio, 2-phenylethylthio, 1 - phenethylthio, phenylthio, octylphenylthio, 1-naphthylthio, and 2-naphthylthio, preferably: methylthio, ethylthio, 1-propylthio, 2- Propylthio, 324066 10 201245157 1-butylthio, 2-butylthio, isobutylthio, pentylthio, hexylthio, octylthio, decylthio, dodecylthio, 2-ethyl The hexylthio group and the 3,7-dimethyloctylthio group are more preferably an anthracenethio group, an ethylthio group, and a 1-propylthio group. The heterocyclic group means an atomic group remaining by directly removing one hydrogen atom in a carbon atom or a nitrogen atom constituting a ring of the heterocyclic compound, and the number of carbon atoms is usually 2 to 30 (the number of carbon atoms is not The number of carbon atoms containing a substituent). Among the heterocyclic groups, since the chemical bonding between the metal and the coordinating atom in the metal complex becomes more stable, it is preferred to use a heteroaryl group (when the above heterocyclic compound is an aromatic heterocyclic compound). Examples of the heterocyclic group include a hetero atom such as one or two or more nitrogen atoms, oxygen atoms, and sulfur atoms. Examples of such a group include a phenazinyl group, a morphine group, a Quinazolinyl group, a cinnolinyl group, an acridinyl group, and an epyrazinyl group. Tri-cultivation, pyrimidinyl, pyridinyl, piperidinyl, piperylene, sputum, quinoxalinyl, benzofuranyl, fluorenyl, benzophenantyl, porphin Base, benzopyrrolidyl, each group, stupid imidazolyl, imidazolyl, benzon-azozolyl, oxazolyl, benzoxazolyl, oxazolyl, benzothiazolyl, thiazolyl, thia The oxadiazolyl, oxadiazolyl, quinolyl, and pyridyl groups are preferably: benzofuranyl, furyl, benzothienyl, thienyl, benzopyrylene, D-pyryl, stupid And imidazolyl, imidazolyl, benzopyrazole, pyrazolyl, benzoxazolyl, oxazolyl, benzothiazolyl, thiazolyl, quinolyl, and pyridyl, more preferably: stupid Imidazolyl, imidazolyl, stupid and oxazolyl, pyrazole 324066 11 201245157 base, benzoxazolyl, oxazolyl, benzothiazolyl, thiazolyl, quinolyl, and More preferably, it is a benzopyridinyl group, a pyridyl group, a thiol group, and a D ratio of 0. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and a ruthenium atom, and an IL atom and a chlorine atom are preferred. Examples of the guanamine group include a guanamine group, an acetamino group, a propylamine group, a butylammonium group, a benzoguanamine group, a trifluoroacetamido group, a pentafluorophenylamine group, and a ruthenium group. The amidino group, the diethylamine group, the dipropylammonium group, the dibutylammonium group, the diphenylguanamine group, the di-trifluoroacetamido group, and the pentafluorophenylamino group are preferably: An amidino group, an acetamino group, a propylamine group, a butylammonium group, and a benzoguanamine group. The quinone imine group is a group obtained by removing a hydrogen atom bonded to a nitrogen atom from a quinone imine. The quinone imine group may, for example, be an N-succinimide group, an N-fluorenylene imino group or a benzophenone quinone group, and is preferably an N-quinone imine group. The substituted fluorenyl group means a fluorenyl group substituted with 1 to 3 hydrogen atoms in the fluorenyl group, and 1 to 3 groups selected from the group consisting of an alkyl group, an aryl group, and an aralkyl group. As the unsubstituted or substituted fluorenyl group, for example, a trimethyl fluorenyl group, a triethyl group, a tripropyl group, a triisopropyl group, a dimethyl isopropyl group, a second Ethyl isopropyl decyl, tert-butyl dimethyl decyl, pentyl dimethyl decyl, hexyl dimethyl decyl, heptyl 324066 12 201245157 dimercaptoalkyl, octyl dimethyl decane Base, 2-ethylhexyl-diindenyl fluorenyl, fluorenyl dimethyl sulphur, fluorenyl fluorenyl, 3,7-didecyl octyl decyl decyl, ten Dialkyl decyl fluorenyl, triphenyl decyl, tri-p-dimethylphenyl decyl, tribenzyl decyl, diphenyl fluorenyl decyl, tert-butyl butyl phenyl decyl, or The dimethylphenyl decyl group is preferably a trimethyl decyl group, a triethyl decyl group, and a tripropyl decyl group 0 as a fluorenyl group, and examples thereof include an anthracenyl group, an ethyl fluorenyl group, and a fluorene group. The butyl group, the butyl group, the isobutyl fluorenyl group, the trimethyl ethane group, the phenyl fluorenyl group, the trifluoroethyl fluorenyl group, and the pentafluorophenyl fluorenyl group are preferably an ethyl fluorenyl group and a phenyl fluorenyl group. Examples of the alkoxy group include a decyloxy group, an ethoxycarbonyl group, a propoxycarbonyl group, an isopropoxycarbonyl group, a butoxycarbonyl group, an isobutoxycarbonyl group, a secondary butoxycarbonyl group, and the like. Tertiary butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, 2-ethylhexyloxycarbonyl, decyloxycarbonyl, decyloxycarbonyl, 3, 7_ Dimethyloctyloxycarbonyl, and dodecyloxycarbonyl, preferably: methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, and isobutylene Oxycarbonyl group. Examples of the oxygen-burning ruthenium group include an oxime sulfonyl group, an ethoxysulfonyl group, a propoxy sulfonyl group, an isopropoxysulfonyl group, a butoxysulfonyl group, and an isobutyl group. Oxysulfonyl, 2-butoxysulfonyl, tert-butoxysulfonyl, pentyloxysulfonyl, hexyloxysulfonyl, heptyloxysulfonyl, octyloxysulfonate , 2-ethylhexyloxysulfonyl, nonyloxysulfonyl, decyloxysulfonyl, 3,7-dimethyloctyloxysulfonyl, and dodecyloxysulfonyl 324066 13 201245157, preferably: methoxysulfonyl, ethoxysulfonyl, propoxysulfonyl, isopropoxysulfonyl, butoxysulfonyl, and isobutoxy Sulfonyl. Examples of the alkoxyphosphonium group include a dimethoxyphosphonium group, a diethoxyphosphonium group, a dipropoxyphosphonium group, a diisopropoxyphosphonium group, and a dibutoxyphosphonium group. The base and the ethylene dioxyphosphonium group are preferably a dimethoxyphosphonium group. The substituted phosphino group means a phosphino group in which one or two hydrogen atoms in the phosphino group are substituted with one to two groups selected from the group consisting of an alkyl group, an aryl group, and an aralkyl group. Examples of the unsubstituted or substituted phosphino group include a phenylphosphino group, a diphenylphosphino group, a decylphosphino group, a decylphosphino group, an ethylphosphino group, a diethylphosphino group, and a propylphosphino group. , dipropylphosphino, butylphosphino, and dibutylphosphino, preferably: diphenylphosphino, dimethylphosphino, diethylphosphino, dipropylphosphino, and Butylphosphino group. The substituted phosphine oxide group means a phosphine oxide group in which one or two hydrogen atoms in the phosphine oxide group are substituted with one to two groups selected from the group consisting of an alkyl group, an aryl group, and an aralkyl group. Examples of the unsubstituted or substituted phosphine oxide group include a phenylphosphine oxide group, a diphenylphosphine oxide group, a methylphosphine oxide group, a dimethylphosphine oxide group, an ethylphosphine oxide group, and a diethyl oxidation. a phosphino group, a propyl phosphine oxide group, a dipropyl phosphine oxide group, a butyl phosphine oxide group, and a dibutylphosphine oxide group, preferably a diphenylphosphine oxide group, a dimercaptophosphine oxide group, or two Ethylphosphine oxide group, dipropylphosphine oxide group, and dibutylphosphine oxide group. 324066 14 201245157 A substituted amine group is an amine group substituted with 1 to 3 hydrogen atoms in the amine group, which is substituted with 1 to 3 groups selected from the group consisting of an alkyl group, an aryl group, and an aralkyl group. Examples of the unsubstituted or substituted amino group include a phenylamino group, a diphenylamino group, a decylamino group, a decylamino group, an ethylamino group, a diethylamino group, and a propylamino group. , dipropylamino, butylamino, and dibutylamino, preferably: diphenylamino, decylamino, dimethylamino, ethylamino, diethylamine a base, a dipropylamino group, and a dibutylamine group. When the substituent is -NET, -CT, -S_, -COO-, -S(V, -ΗΡ0Γ, or -Η2Ρ0; Γ, it may have a relative ion. As the counter ion, for example, lithium ion, The sodium ion, the potassium ion, the cerium ion, the dicing ion, and the ammonium ion are preferably: sodium ion, potassium ion, and ammonium ion. <Metal skeletal> The metal displacing body of the present invention is represented by the above formula (1) The metal complex has a ratio of sp3 carbon atoms contained in the metal complex of 22% by mass or more based on the total mass of the metal complex. The ratio of sp3 carbon atoms contained in the metal complex is less than 22 When the mass is %, the solubility in a nonpolar solvent is deteriorated, and it is difficult to form a uniform film. On the other hand, the ratio of sp3 carbon atoms contained in the metal complex is excellent in solubility of the metal complex, and is preferably In the range of 22 to 90% by mass, preferably 22.5 to 80% by mass, more preferably 25 to 70% by mass, particularly preferably 25 to 60% by mass. The sp3 carbon atom means carbon having sp3 mixed behavior. Atom. In the metal complex of the present invention, in order to dissolve the non-polar solvent more preferably, At least one of the sp3 carbon atoms is preferably a carbon atom of 3 or 4, 324066 15 201245157. Further, the total number of carbon atoms of the 3rd or 4th order relative to the total number of the sp3 carbon atoms is Preferably, it is preferably 0.05 or more, and more preferably 0.1 or more. In the above formula (1), in order to be easily obtained, it is preferable to use cerium ions or cerium ions, and cerium ions are more preferable. The valence of the metal ion is preferably a valence of 3. The relative ion represented by X in the above formula (1) may be a cation or an anion. Examples of the cation include a cation, a sodium ion, and As the anion, for example, fluoride ion, chloride ion, bromide ion, iodide ion, sulfate ion, nitrate ion, carbonate ion, acetate ion, and overgas can be cited. Acid ion, tetrafluoroborate ion, hexafluorophosphate ion, hexafluoroantimony ion, hexafluoroarsenic ion, decane sulfonate ion, trifluorodecane sulfonate ion, trifluoroacetate ion, benzene sulfonate ion, P-toluenesulfonic acid ion, dodecanebenzene Acid ion, tetraphenylborate ion, quinone (pentafluorophenyl) borate ion. As the relative ion represented by X, it is desirable to: fluoride ion, chloride ion, nitrate ion, perchlorate ion, Tetrafluoroborate ion, hexafluoro acid S ion, hexahydrate ion, hexafluoro ion, sulphur acid ion, trifluorosulfonate acid ion, trifluoroacetate ion, benzene acid ion, pair a terephthalic acid ion, a dodecylbenzenesulfonate ion, a tetraphenylboronic acid vinegar ion, and a quinone (pentafluorophenyl) borate ion. Preferred are: chloride ion, nitrate ion, perchlorate ion , 324066 16 201245157 fluoroborate ion, hexafluorophosphate ion, decane sulfonate ion, trifluorodecane sulfonate ion, trifluoroacetate ion, benzene sulfonate ion, p-toluene sulfonate ion, tetraphenyl Boron ion, and quinone (pentafluorophenyl) borate ion. More preferred are perchloric acid ions, tetrafluoroborate ions, hexafluorophosphate ions, trifluoromethanesulfonate ions, trifluoroacetate ions, and tetraphenylborate ions. Particularly preferred are: tetrafluoroborate off-hand, hexafluorophosphate ion, trifluorosulfonate ion, and tetraphenyl borate ion. In the above formula (1), the ligand of the single or double teeth represented by L' usually contains an atomic group selected from at least one atom selected from the group consisting of an oxygen atom, a nitrogen atom and a phosphorus atom, and examples thereof include, for example, : water, sterol, ethanol, acetone, tetrahydrofuran, dimercaptosulfoxide, triarylphosphine oxide, trialkylphosphine oxide, biting, 啥琳, α than saliva, p rice bran, 卩, etc. Spit, benzoximepine, benzoxazole, benzothiazole, tri-farming, pyrimidine, pyridin, bipyridine, biquineline, terpyridine, phenanthroline, triaryl Phosphine, trialkylphosphine, trialkylamine. In the above formula (1), a is preferably from 1 to 3, preferably from 1 or 2, more preferably 2. In the above formula (1), b is preferably 0 to 4, preferably 0 to 3. In the above formula (1), c is preferably 0 to 6, more preferably 0 to 3, still more preferably 0. In the above formula (1), in order to improve the stability of the metal complex in the combination of a and c, it is particularly preferable that a is 2 and c is 0. 324066 17 201245157 In the above formula (1), L is a ligand represented by the above formula (2). The number of coordination teeth of this ligand (ie, the number of coordination atoms) 'is usually 3 or more teeth, preferably 3 to 12 teeth, preferably 3 to 8 teeth, more preferably 4 to 8 teeth, especially Jia is 4 teeth. In the metal complex of the present invention, in order to have better solubility in a nonpolar solvent, L is preferably 15 to 200 sp3 carbon atoms, preferably 18 to Π0, and preferably 21 to 120. More preferably, it is preferably from 24 to 100, preferably from 27 to 80.至85至85。 The metal disperse of the present invention, in order to have a better solubility in a non-polar solvent, L is preferably from 3 to 95% by mass of sp3 carbon atoms, and contains 32. 5 to 85. The mass % is preferably, and it is preferably from 35 to 75 mass: a:% is more preferable to contain 37. 5 to 65 mass%. In the above formula (2), the number of carbon atoms of the hydrocarbon diradical (so-called hydrocarbylene group) which may have a substituent represented by A1, A2 and A3 is usually from 1 to 30, preferably from 1 to 20. More preferably, it is 1 to 1 inch. Examples of the hydrocarbon diradical group include an anthracenylene group, an ethylene group, a propyl group, a butyl group, a pentyl group, a hexyl group, a decyl group, a methyl group, and a propyl group. Ethyl ethyl, ethyl propyl, decyl butyl, ethyl hexyl, dinonyl octyl, cyclopropylene, cyclopentyl, cyclohexyl, adamantane diyl, hail Diyl, phenylmethylene, vinyl, propylene, butyl, diphenyl, vinyl, phenyl, phenyl, phenyl, methyl, phenyl Stupid diyl, triphenyldiyl, tetraphenyl phenyl, (2,2-diphenylvinyl)phenyl, (1,2,2-triphenylvinyl) 324066 18 201245157 phenyl , fluorenyl, anthranyl, anthracenyl, phenanthrenyl, and acridinediyl. Desirably, methylene, ethyl, propyl, butyl, fluorenyl, ethyl, propyl, ethyl, ethyl, ethyl, propyl, butyl, butyl, A hexyl group, a phenylmethylene group, a vinyl group, a propylene group, and a phenyl group. Preferred are an anthracenylene group, an ethylidene group, a propyl group, a butyl group, a methyl group, an ethyl group, a propyl group, a vinyl group, or a propylene group. More preferred are: methylene, ethyl, propyl, butyl, methyl ethyl, and decyl propyl. In the above formula (2), 'L, L2 and L3 are preferably all ligands. The ligand represented by L1, L2 and L3 means a nitrogen atom having an isolated electron pair or an oxygen atom having an isolated electron pair. The number of carbon atoms of the ligand represented by L1, L2 and L3 is usually from 〇 to 5 Å, preferably from 0 to 40, more preferably from 〇 to 2 Å. Examples of the ligand represented by L, L2 and L3 include a hydrocarbyloxy group which may have a substituent, a heterocyclic group which may have a substituent, an anthranyl group which may have a substituent, and a mercapto group which may have a substituent An alkoxycarbonyl group which may have a substituent, a phosphine oxide group which may have a substituent, an amine group which may have a substituent, a trans group, a carboxyl group, a sulfo group, a phosphate group, and a nitro group, 〇〇-, _C〇〇 -, _s〇3-, -HPO,. Preferred are a heterocyclic group which may have a substituent, an anthranyl group which may have a substituent, a phosphine oxide group which may have a substituent, an amine group which may have a substituent, a certain group, a thiol group, a contiguous group, and a An acid group, -c〇〇., _s〇" and _Ηρ〇4-. More preferably, a heterocyclic group which may have a substituent, a 324066 19 201245157 oxidized squaring group which may have a substituent, may have a substituent Amine group, _coo-, _s〇3-&amp;_HP〇4-. More preferably: a heterocyclic group which may have a substituent. In the above formula (2), at least one of I;, L2 and L3 is In the case of the heterocyclic group which may have a substituent as a ligand, the metal complex of the present invention is excellent in the light-emitting intensity. Therefore, it is preferred that the heterocyclic group which may have a substituent be represented as a whole. The heterocyclic group means a group containing a nitrogen atom having an isolated electron pair or an oxygen atom having an isolated electron pair as a hetero atom. It is preferable to contain a nitrogen atom having an isolated electron pair. For example, pyrroline group, pyrrolidinyl group, morphinyl group, quinuclidinyl group (qui Nuciidinyi), dioxaxanyl, dihydrofuranyl, tetrahydropyranyl, piperylene, piperidinyl, furyl, phenyl, pyridyl, quin Porphyrin group, sold as a salivyl group, alkaloids such as di-salt, indole, indole, 吖β-based, β-bite, 噎 基, 卩, 卩, η 、 Base, H, butyl, hydrazino, tripyridyl, phenanthroline, pyridine-oxime oxime, pyridyl, pyrazolyl, imidazolyl, Pf azole, thiazolyl, stupid And benzoxazolyl, and phenylthiazole, preferably: morphyl, pyridyl, quinoxalinyl, thiadiazolyl, oxazolyl, quinazolinyl, porphyrin, acridine Base, pyridyl, quinolyl, tridecyl, pyrimidinyl, pyridene, pyridyl, biquinolinyl, tripyridyl, phenanthroline, pyridine-N-oxide, pyri[I a pyridyl group, a pyrazolyl group, an oxazolyl group, a thiazolyl group, a benzimidazolyl group, a benzoxazolyl group, and a benzothiazolyl group. More preferably: a pyridyl group, a quinolyl group, an imidazolyl group, an oxazolyl group, Thiazole 324066 20 201245157 base, stupid and microphone And a benzoyl group and a benzothiazol group. Further, as the amine group which can be the above ligand, for example, an aniline is exemplified. Base, diphenylamino, mercaptoamine, dinonylamino, ethylamino, diethylamino, propylamino, dipropylamino, butylamino, and dibutylamino Preferred are an anilino group, a mercaptoamine group, an ethylamino group, a propylamino group, and a butylamino group. As a hydrocarbyloxy group, a mercaptoamine group, a mercapto group or an alkane which can form the above ligand group Specific preferred examples of the oxycarbonyl group, the alkoxysulfonyl group, the alkoxyphosphinyl group, and the phosphine oxide group are the same as those described for the "substituent". When the above ligand is -(Τ, -C00, -S〇3—, or -ΗΡΟΓ, it may have a relative ion. Examples of the relative ion include lithium ion, sodium ion, clock ion, and ion ion. The ion and the ammonium ion are preferably a nano ion, a clock ion, and a sigma ion. The metal complex of the present invention has excellent luminescence intensity, and therefore at least one of L1, L2 and L3 is represented by the following formula (3). The group represented by the formula (4) is preferred, and the group represented by the following formula (3) is more preferable.

[In the formula (3), R6 represents a hydrogen atom, a hydrocarbon group which may have a substituent, or a heterocyclic group which may have a substituent, and R7 represents -(Γ, -C00-, -S(V, -ΗΡ0Γ, may have The hydrocarbon of the substituent 324066 21 201245157, a hydrocarbyloxy group which may have a substituent, a heterocyclic group which may have a substituent, a certain group, a thiol group, a contiguous group, or a scaly acid group, and j is an integer of 0 to 2. When the nitrogen atom bonded to R6 and the carbon atom bonded to R7 are in the adjacent position, R6 and R7 may also combine to form a ring. That is, R6 and R7 may be bonded to each other, and also to the nitrogen atom and carbon atom respectively bonded thereto. Forming a ring together. J is 2 '2 R7 is bonded to carbon atoms adjacent to each other, and 2 R may be combined to form a ring. That is, two Rs may be bonded to each other, together with the carbon atoms respectively bonded thereto. When J is 2, two R7s may be the same or different.] [In the formula (4), R represents -0, -C00, _s〇3_, -HP〇4-, a nicotine group which may have a substituent, a hydrocarbyloxy group which may have a substituent, a heterocyclic group which may have a substituent, a hydroxyl group, a carboxyl group, a contiguous group, or a phosphoric acid group, and k is an integer of 0 to 3. K is 2 or 3, complex When a plurality of r8 are bonded to carbon atoms adjacent to each other, a plurality of R8 may be combined to form a ring, that is, a plurality of R8 may be combined and form a ring together with the carbon atoms respectively bonded thereto. K is 2 or 3, The plurality of R8 may be the same or different. In the above formula (3), R6 is preferably a hydrocarbon group which may have a substituent. y represents a substituent which may have a substituent, and may have a substituent. 201245157 and preferred examples are the same as those described in the section "Substituents". In the above formulas (3) and (4), R7 and R8 are a hydrocarbon group which may have a substituent and may have a substituent. Alkoxy groups, hydroxyl groups, carboxyl groups, sulfo groups, and phosphoric acid groups are preferred, and preferred are hydrocarbon groups which may have a substituent. Hydrocarbon groups which may have a substituent represented by R7 and R8, and hydrocarbon groups which may have a substituent Specific examples and preferred examples of the heterocyclic group having a substituent and a substituent are the same as those described in the section "Substituent". In the above formulas (3) and (4), it is contained in R6, R7 and R8. The total number of sp3 carbon atoms is preferably from 12 to 150, and the sp3 carbon atoms contained in R6, R7 and R8 are 4 to 50, respectively. Preferably, it is preferably 5 to 40, more preferably 6 to 33, particularly preferably 7 to 33, and most preferably 8 to 33. In the above formula (3), j is an integer of 0 to 2, 0 or 2 is preferable, and when j is 2, two R7 groups may be bonded to each other and form a ring together with the carbon atoms to be bonded together. As the formed ring, since it has high solubility to a nonpolar solvent and is easy to manufacture, The benzene ring which may have a substituent is preferred. The substituent is preferably a halogen atom, a hydrocarbon group or a hydrocarbyloxy group, and an alkyl group having 1 to 10 carbon atoms is preferably a mercapto group, an ethyl group or a 1-propyl group. And hexyl is better. In the above formula (4), k is an integer of 0 to 3, preferably 0 to 2, more preferably an integer of 0 to 1. Since the metal complex of the present invention has excellent light emission intensity, L is preferably a ligand represented by the following formula (5). 324066 23 201245157

η [In the formula (5), R9, R1() and R11 are each independently a hydrogen atom, a hydrocarbon group having four or more sp3 carbon atoms which may have a substituent, or a group having four or more sp3 carbon atoms which may have a substituent. The heterocyclic group, R12, R13 and R14 are each independently and represent -(Γ, -C00_, -S(V, -ΗΡΟΓ, a hydrocarbon group which may have a substituent, a hydrocarbyl group which may have a substituent, may have a substituent) a heterocyclic group, a hydroxyl group, a carboxyl group, a sulfo group or a phosphoric acid group, and R15, R16, R17, R18, R19 and R2° are each independently represented by a hydrogen atom or a substituent, and m, n and p are each independently represented. An integer from 0 to 2. When m is 2, two R12s may be the same or different, or may be combined to form a ring. That is, two R12s may be the same or different, may be combined with each other, and combined with each other. The carbon atoms form a ring together. When η is 2, two R13s may be the same or different, or may be combined to form a ring. That is, two R13s may be the same or different, and may be combined with each other. The bonded carbon atoms form a ring together. When ρ is 2, two R14s may be the same or different, or may be combined to form a ring. That is, the two R14s may be the same or different, may be combined with each other, and form a ring together with the carbon atoms respectively combined.] 324066 24 201245157 Description = (5), 1^, [^ and R«! It is preferred that the hydrocarbon group may have a substituent. The hydrocarbon group having four or more ruthenium 3 • carbon atoms which may have a substituent represented by R, Rlf1 and Rn, and the group having four or more ruthenium 3 carbon atoms which may have a substituent The heterocyclic group is the same as the "substituent" (4). In the above formula (5), R9, R111 and the hydrogen atom group having four or more sp3 carbon atoms which may have a substituent may be substituted. Preferred are: butyl, 2-butyl, isobutyl, pentyl, hexyl, octyl, decyl, dodecyl, 2-ethylhexyl, 3,7-monomethyloctyl, cyclopropane Base, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 3,5-di-tert-butylbenzyl, 3,5-di-tert-butylphenyl, alpha, dimethyl —3, 5-di-tertiary butylhexyl, oleyl, eicosylpentenyl, docosahexaenyl, 2,2-bis-(3,5-di-tert-butylphenyl) )vinyl, 4-methylpentyl, 3,5-bis-(3-methylbutoxy) Benzyl, 3-(4-tri-butylphenyl)propyl. More preferred: hexyl, octyl, decyl, dodecyl, 2-ethylhexyl, 3' 7-dimethyl Octyl, 3,5-di-tertiary butylbenzyl, 3,5-di-tertiary butylphenyl, 2-(3,5-di-tri-butylphenyl)ethyl, 2, 2_Bis(3'5_di-tert-butylphenyl)vinyl, 4-mercaptopentyl, 3,5-bis-(3-mercaptobutoxy)benzyl, 3-(4 -Tris-butylphenyl)propyl. More preferably: octyl, decyl, dodecyl, 2-ethylhexyl, 3,7-nonyloctyl, 3, 5_di Tert-butyl benzyl, 3,5-di-tertiary butylphenyl, 4-methylpentyl. In the above formula (5), R9 and R1 are used. And a heterocyclic group having 4 or more sp3 carbon atoms which may have a substituent represented by Ru, preferably 2,6-di-butylidene-4-yl, 4,6-di-tris Butylpyridin-2-yl, 3, 6-324066 25 201245157 Di-tertiary butyl fluorene-8-yl, 2, 7-di-tertiary butyl fluorene-5-yl, hydryl, quinine Ning ring base, tetrahydrogen bite β south base, tetrahydrogen thiol group, D base thiol group, sigma group, more preferably: morphinyl, quinuclidinyl, tetrahydroanthranyl, tetrahydropyridyl More preferably, a thiol group, a piperidinyl group or a piperidinyl group is a tetrahydrofuranyl group or a tetrahydrocarbamate group. In the above formula (5), R12, R13 and R14 are preferably a hydrocarbon group which may have a substituent, a hydrocarbyloxy group which may have a substituent, a hydroxyl group, a carboxyl group, a sulfo group or a phosphoric acid group, and more preferably: may have a substitution Hydrocarbyl group. Specific examples and preferred examples of the hydrocarbon group which may have a substituent represented by R12, R13 and R14, a hydrocarbyloxy group which may have a substituent, and a heterocyclic group which may have a substituent, and the description of the "substituent" The same. In the above formula (5), specific examples and preferred examples of the substituents represented by R15, R16, R17, R18, R19 and R2 are the same as those described for the "substituent". In the above formula (5), the number of sp3 carbon atoms contained in R9, R1() and R11 is preferably 4 to 50, preferably 5 to 40, more preferably 6 to 33, respectively. The best is 7 to 33, and the best is 8 to 33. In the above formula (5), m is an integer of 0 to 2, preferably 0 or 2, and when m is 2, two R12s may be bonded to each other and form a ring together with the carbon atoms to be bonded together. In the above formula (5), η is an integer of 0 to 2, preferably 0 or 2, and when η is 2, two R13s may be bonded to each other and form a ring together with the carbon atoms respectively bonded thereto. In the above formula (5), ρ is an integer of 0 to 2, preferably 0 or 2, and when ρ is 2, two R14s may be bonded to each other and form a ring together with the carbon atoms 324066 26 201245157 which are respectively bonded. The above formula (5) t, m, 11 and p are preferably the same value.

* The metal complex of the present invention has excellent luminescence intensity, and therefore, the ligand represented by the formula (6) is preferred.

And R are each independently a hydrocarbon group having four or more sp &amp; atoms which may have a substituent, or a heterocyclic group having at least one sp3 carbon atom which may have a substituent. In the 21st formula (6), mR23 preferably has a substituent hydrocarbon group. Specific examples of "hydrocarbon group" containing four or more sp3 carbon atoms which may have a substituent represented by r R and R, and a substituent group containing a 4 sen sp3 carbon atom, and a "substituent" term The same is stated. In the above formula (6), the hydrocarbon group having four or more sp3 carbon atoms which may have a substituent represented by R21, R22 and R23 is preferably a butyl group, a dibutyl group, an isobutyl group or a pentyl group. Hexyl, octyl, decyl, dodecyl, 2-ethylhexyl, 3,7-dimethyloctyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 3, Di-tertiary butylbenzyl, 3,5-di-tert-butylphenyl, α, dimethyl-3, 5-di-tert-butylbenzyl, oleyl-decapentapentenyl , docosahexaenoyl, 2,2-bis-(3, 5-di-324066 27 201245157 tert-butylphenyl)vinyl, 4-mercaptopentyl, 3, 5-bis-(3 - mercaptobutoxy) nodal, 2-(3,5-di-tri-butylphenyl)ethyl, 3-(4-tributylbutyl)propyl. More preferably: hexyl, octyl, decyl, dodecyl, 2-ethylhexyl, 3,7-dimethyloctyl, 3,5-di-tertiary butylbenzyl, 3, 5 -di-tertiary butylphenyl, 2-(3,5-di-tri-butylphenyl)ethyl, 2,2-bis-(3,5-di-tertiary butylphenyl)ethylene Base, 4-methylpentyl, 3,5-bis-(3-decylbutoxy)benzyl, 3-(4-tri-butylphenyl)propyl. More preferably, it is octyl, decyl, dodecyl, 2-ethylhexyl, 3'-didecyloctyl, 3,5-di-tertiary butylbenzyl, 3, 51-2. Tert-butyl phenyl, 4-methylpentyl. In the above formula (6), as the heterocyclic group having four or more sp3 carbon atoms which may have a substituent represented by r21, r22, and R23, preferred is 2,6-di-di-butylpyridine. 4-yl, 4,6-di-tertiary butylpyridine-2-yl, 3,6-di-tertiary butyl fluorene-based I, 2, 7-di-tertiary butyl fluorene _5_ Base, morphinyl, quinine nucleobase, tetrahydrofuranyl, tetrahydron-pyranyl, (iv) well base, pie base. More preferred are: linnyl, quinuclidinyl, tetrahydrocarbyl, tetrahydrofuranyl, piperidinyl, piperidinyl. More preferably, it is a tetrahydrofuranyl group or a tetrahydropyranyl group. The above 5U6) is preferably 4 to 50, preferably, ρ ^ _ ^ 40 40, more preferably 6 to 33 疋 7 至 7 to 33 'best 8 to 33 . Examples of the ligand represented by the above-mentioned L include the following formula (IV) 324066 28 201245157 to (A-17), (Al-2), (A-2-2), (A-3- 2), The ligand represented by (A-5-2) is excellent in the light-emitting intensity of the metal complex of the present invention. Therefore, the ligand represented by the following formulas (A-δ) to (A-17) is preferred. More preferably, it is a ligand represented by the following gases (A-12) to (A-17).

(Α·2)

324066 29 201245157 324066 201245157

(A-10)

324066 31 201245157

324066 32 201245157

(A-16)

Examples of the metal complex of the present invention include metal complexes represented by the following formulas (B1) to (B-12), and since the luminescence intensity is excellent, the following formula (B-6) is preferred. The metal complex represented by (B-12) is more preferably a metal complex represented by the following formulas (B-7) to (B-12). 324066 33 201245157

324066 34 201245157

3

CF3S03· 324066 35 201245157 c#+

Ce^

324066 36 201245157

(B-10) 324066 37 201245157

<Method for Producing Compound to Be a Ligand Group> The compound which is the above ligand can be produced by any method, but can be easily produced by the production method described below. Here, as the compound to be a ligand, a ligand represented by the above formula (5) (corresponding to the compound of the present invention) and a ligand represented by the above formula (6) (corresponding to the present invention) The compound) is explained as an example. The ligand represented by the above formula (5) or the ligand represented by the above formula (6) is preferably a ligand represented by the above formula (A-8) to (A-17), and the above formula The ligands represented by (A-8) and (A-12) to (A-17) are preferred, and the ligands represented by the above formulas (A-12) to (A-17) are more preferable. The ligand represented by the above formula (5), for example, a substituted or unsubstituted 324066 38 201245157 3, 3',3',-nitrotriacetic acid (3, 3,, 3' ' _nitril triacetic acid) The diamine compound is heated and condensed, and is obtained by reacting with a tooth compound in the presence of a base or an alkali metal in a solvent, and the substituted or unsubstituted 3,3',3''-nitrotriacetic acid is The n-substituted diamine-based compound is heated together and can also be obtained by condensation. The ligand represented by the above formula (6) is obtained by heating and condensing 3, 3', 3'-nitrotriacetic acid together with 1,2-diaminobenzene, by using this in a solvent, an alkali or an alkali metal. In the presence of a halogen compound, it can also be obtained by heating and condensing together with N-substituted 1,2-diaminobenzene by reacting 3, 3, 3, and _-nitrotriacetic acid. <Manufacturing method of metal complex body> The metal complex of the present invention may be produced by any method, but the compound and the metal salt which are the ligands described above are mixed in a solvent at room temperature, and as a result, The precipitation can be easily produced by recovering or by distilling off the solvent by the reaction liquid. Examples of the metal salt include cerium salts such as vaporized cerium (111), cerium nitrate (III), and difluoromethane hydride (HI); gasified cerium (m), cerium nitrate (III), and three Barium salts such as fluoromethyl sulphate (111); gasification mirrors (ΙΠ), bismuth (III), trifluoromethane (10), etc.; chlorinated ore (III); III), a phosphonium salt such as lanthanum trifluoromethanesulfonate (Ιπ). The amount of the metal salt to be used is usually 5 to 80 parts by mass, preferably 1 to 7 parts by mass, more preferably 20 to 60 parts by mass, per 100 parts by mass of the compound to be a ligand. Examples of the solvent to be used in the above mixing include a buffer solution, etc. 324066 39 201245157 aqueous solvent, and an organic solvent, m ^ - an organic solvent is preferred. The solvent may be used singly or in combination of two or more. As an organic solvent, it can be listed as a nitrile solvent such as acetonitrile or benzonitrile; :: decane, 1,2-dioxaethane, 112_tri-ethane, chlorobenzene, :-Chlorine: gas solvent; tetrahydroanthracene, dioxane and other solvent; A:: a sulphur-like aromatic hydrocarbon solvent; cyclohexane, methylcyclohexane, η-, η - Glyph, n-xin, η_壬, 卩 癸 癸 等 她 她 her solvents; propyl, methyl ethyl ketone, cyclohexanone and other ketone solvents; vinegar I acetyl acetate, butyl acetate, Ester solvent such as ethyl acesulfate; ethylene glycol, ethylene glycol monobutyl hydrazine, ethylene glycol monoethyl hydrazine, ethylene glycol monomethyl hydrazine, dimethoxy ethoxylate, propylene glycol, diethyl Alcohols, triethylene glycol monoethyl scales, glycerol, 1,2-hexanediol and other polyols and derivatives thereof; alcohol solvents such as decyl alcohol, ethanol, propanol, isopropanol, cyclohexanol ; dimethylene hard and other sub-sectors are dissolved in 1 ' thiol-2-1 each _, Ν, Ν _ dimethyl ketone and other amine-based solvents 'one gas simmer and acetonitrile is preferred. <Composition> The metal complex of the present invention can be used as it is, or can be used as a composition by mixing with a charge transport material. This composition is at 25. The sputum is liquid or solid. The above-mentioned charge transporting material is a material which is used for charge transport in an organic electronic component such as an organic electroluminescence device (hereinafter referred to as "light emitting device"), and specifically, a hole transporting material and an electron transporting material. The charge transporting material can be classified into a low molecular organic compound and a high molecular organic compound (e.g., 'polymer compound, oligo polymer). Polymer Organic Compound 324066 40 201245157 % The polymer compound and the oligomeric polymer are preferably a conjugated system. As the above-mentioned hole transporting material, a known material of ruthenium and its derivatives, an aromatic amine and a derivative thereof, a π-card β-seat derivative, a poly-p-phenylene derivative, or the like can be used as the organic electroluminescence device. The hole transport material. As the above electron transporting material, a oxadiazole derivative, a decanedioxane and a derivative thereof, a benzoquinone and a derivative thereof, a naphthoquinone and a derivative thereof, an anthracene and a derivative thereof, and a tetracyanate can be used. Based on dioxane and its derivatives, S醌 derivatives, diphenyldicyanoethylene and its derivatives, diphenylguanidine derivatives, and metal morphologies of 8-hydroxyquinoline and its derivatives An electron transporting material of an organic electroluminescent element. 01至60。 Preferably, the composition of the present invention is preferably 0.1 to 80 parts by mass, preferably 0.1 to 60. Parts by mass. In the composition of the present invention, the metal complex of the present invention and the above-mentioned charge transporting material may be used alone or in combination of two or more. <Organic film> The organic film of the present invention contains the metal complex of the present invention. The organic film of the present invention can be easily formed into a film by a coating method such as an inkjet printing method, for example, by using a solution obtained by mixing the metal complex of the present invention with a solvent. The organic film of the present invention can be used as a light-emitting film, a conductive film, and an organic semiconductor film. The thickness of the organic film of the present invention is preferably from 1 to 500 nm, more preferably from 5 to 200 nm. <Organic Electronic Component> 324066 41 201245157 The organic electronic component of the present invention is a metal complex containing the present invention. The organic electronic component of the present invention may, for example, be a light-emitting element, a conversion element, or a photoelectric conversion element including a functional layer containing the metal complex of the present invention. <Light-emitting element> A light-emitting element usually has a light-emitting layer between electrodes composed of an anode and a cathode. The light-emitting element may contain a layer other than the light-emitting layer in order to improve luminous efficiency and durability. Examples of the layer other than the light-emitting layer include a charge transport layer, a charge block layer, a charge injection layer, and a buffer layer. Each layer may be composed of one layer or two or more layers. The luminescent layer is a layer having an illuminating function. The hole transport layer is a layer having a function of transporting holes, and the electron transport layer is a layer having a function of transporting electrons, and the electron transport layer and the hole transport layer are collectively referred to as a charge transport layer. A charge blocking layer is a layer having a function of blocking a hole or an electron in a light-emitting layer, wherein a layer that transports electrons and closes a hole is called a hole blocking layer, and the hole is transported and the layer of electrons is closed. It is called an electron blocking layer. The buffer layer may, for example, be a layer containing a conductive high molecular compound adjacent to the anode. As the structure of the light-emitting element, the following structures a) to q) can be cited. a) anode / luminescent layer / cathode b) anode / hole transport layer / luminescent layer / cathode c) anode / luminescent layer / electron transport layer / cathode d) anode / luminescent layer / hole barrier / cathode e) anode / Hole transport layer / luminescent layer / electron transport layer / cathode 324066 42 201245157 f) anode / charge injection layer / luminescent layer / cathode g) anode / luminescent layer / charge injection layer / cathode • h) anode / charge injection layer / luminescence Layer/charge injection layer/cathode • i) anode/charge injection layer/hole transport layer/light-emitting layer/cathode j) anode/hole transport layer/light-emitting layer/charge injection layer/cathode k) anode/charge injection layer/ Hole transport layer / luminescent layer / charge injection layer / cathode l) anode / charge injection layer / luminescent layer / electron transport layer / cathode m) anode / luminescent layer / electron transport layer / charge injection layer / cathode η) anode / charge Injection layer / luminescent layer / electron transport layer / charge injection layer / cathode 〇) anode / charge injection layer / hole transport layer / luminescent layer / electron transport layer / cathode θ = Ρ) anode / hole transport layer / luminescent layer / Electron transport layer / charge injection layer / cathode π q) anode / charge injection layer / hole transport layer / luminescent layer / electron transport / Charge injection layer / cathode (herein the symbol "/" means that each layer is adjacent to each other and the light layer, the hole transport layer, and the electron transport limb are independent of each other. (4) Two or more layers.) Charge transport layer provided adjacent to the electrode Among them, there is a function of improving the charge injection efficiency of the electrode 'the effect of lowering the driving voltage of the light-emitting element' - generally referred to as a charge injection layer. Examples of the light-emitting element having a charge-injecting layer include a light-emitting element having a charge-injecting layer adjacent to a gray age, and a light-emitting element having a charge injection layer adjacent to the anode. 324066 43 201245157 In order to improve the adhesion to the electrodes, or to improve the injection of the charge from the electrodes, the light-emitting elements may be adjacent to the electrodes to provide an insulating layer. Examples of the material used in the above insulating layer include metal fluorides, metal oxides, and organic insulating materials. The thickness of the insulating layer is usually 2 nm or less. Examples of the light-emitting element having the insulating layer include a light-emitting element having a cathode adjacent to the cathode, and a light-emitting element having the insulating layer adjacent to the anode. The light-emitting layer is preferably a layer containing the metal complex of the present invention or the composition of the present invention. Other luminescent materials may also be included in the luminescent layer. Examples of other luminescent materials include naphthalene derivatives, anthraquinone and derivatives thereof, flowers and derivatives thereof, polymethine, xanthene, coumarin, and flowers. Cyanine and other pigments, 8_ metal morphologies of quinone and its derivatives, aromatic amines, tetraphenylcyclopentadiene and its derivatives, and tetraphenylbutadiene and its derivatives . Examples of the material to be used in the hole transport layer include polyvinyl carbazole and derivatives thereof, polydecane and derivatives thereof, and polyoxin having a sulfonate compound group in a side chain or a main chain. Pyridin derivatives, „Bilin derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, polyamines and derivatives thereof, polyamines (P〇lyamin〇phene) and a derivative thereof, a polypyrrole and a derivative thereof, a poly(p-phenylene vinylene) and a derivative thereof, and a poly(2,5-thienylene vinylene) and The thickness of the hole transport layer is set such that the light-emitting efficiency or the photoelectric efficiency and the driving voltage become appropriate values, usually from 1 nm to 1 Am, more preferably from 324066 44 201245157 to 2 nm to 500 nm', more preferably 5 nm. To 200 nm. As the material to be used in the electron transport layer, for example, a pyroxazole derivative, quinodimethane and a derivative thereof, benzoquinone and a derivative thereof, naphthoquinone and a derivative thereof, and Its derivatives, tetracyanoquinone dioxane and its derivatives, Derivatives, diphenyl cyanoethylene and its derivatives, diphenyl hydrazine derivatives, metal morphologies of 8-hydroxyquinoline and its derivatives, polyquinolines and their derivatives, polyquinoxalines and their derivatives The thickness of the electron transport layer is set such that the light-emitting efficiency or the photoelectric efficiency and the driving voltage are appropriate values, and is usually from 1 nm to 1 μm, and preferably from 2 nm to 500 nm. The layer is formed on the adjacent layer or on the substrate. Examples of the formation method include a vacuum deposition method (resistance heating vapor deposition method, electron beam method, etc.), sputtering method, and LB. In the method, the molecular layering method, and the coating method, it is preferable to use a coating method in order to simplify the manufacturing process. Examples of the coating method include a spin coating method, a mold casting method, a dip coating method, and a gravure coating method. , bar coating method, roll coating method, spray coating method, screen printing method, soft printing method, lithography method, and inkjet printing method, and the coating method, the spray coating method, Soft printing and inkjet printing are preferred. It is often formed by using a substrate, and an electrode is formed on one surface of the substrate, and each layer of the element is formed on the other surface. Examples of the substrate include a substrate made of a material such as glass, plastic, polymer film, or tantalum. The anode and the cathode contained therein are transparent or translucent, but the anode is preferably transparent or translucent. 324066 45 201245157 As a material used for the anode, for example, a conductive metal oxide film, translucent a metal thin film or an organic transparent conductive film, preferably: indium oxide, zinc oxide, tin oxide, and the like (indium/tin/oxide (ΙΤ0), indium/zinc/oxide, etc.), 锑/tin/oxide, NESA, gold, platinum, silver, copper, polyaniline and its derivatives, polyaminobenzene and its derivatives. Examples of the method of forming the anode include a vacuum deposition method, a sputtering method, an ion plating method, and a plating method. The thickness of the anode is set in consideration of light transmittance and conductivity, and is usually from 10 nm to 10 // m, preferably from 20 nm to 1 // m, more preferably from 40 nm to 500 nm. As the material used in the cathode, it is preferable to use a material having a small work function*, for example, lining, nano, potassium, recording j, absolute, bond, town, about, wrong, lock, Ming, navigation, sputum, zinc, Metals such as indium, indium, antimony, #, pin, money, mirror; metal alloys selected from the group consisting of two or more metals; and one or more metals selected from the group consisting of such metals An alloy of more than one metal in a group of free gold, silver, platinum, copper, lanthanum, titanium, beginning, nickel, crane, and tin; graphite; graphite intercalation compound. Examples of the method for forming the cathode include a vacuum deposition method, a sputtering method, and a lamination method in which a metal thin film is thermally pressed, and a cathode having a laminated structure of two or more layers may be formed. The thickness of the cathode is set in consideration of conductivity and durability, and is usually from 10 nm to 10 μm, desirably from 20 nm to 1 // m, and more preferably from 50 nm to 500 nm. 324066 46 201245157 In the case of a light-emitting element, in order to be used for a long-term stability by an external protective element, a protective layer or a protective cover for protecting the light-emitting element may be formed. Examples of the charge injection layer include a layer containing a conductive polymer, a layer containing a material having an intermediate value ionization potential of a hole transport material contained in the anode material and the hole transport layer, and A layer comprising a material having an intermediate value of electron affinity between the cathode material and the electron transporting material contained in the electron transporting layer. Examples of the material used in the charge injection layer include polyaniline and derivatives thereof, polyamines and derivatives thereof, polypyrrole and derivatives thereof, poly(extended vinyl group) and derivatives thereof, Poly(thiophene phenylene) and its derivatives, polyquinoline and its derivatives, polyquinoxaline and its like, and conductive polymers such as polymers containing aromatic amines in the main chain or side chain , metal phthalocyanine, and carbon. The thickness of the β charge injection layer is usually, preferably, 疋Inm to 50 nm, more preferably 1 (10) to 1 〇 nm 区段 segment display device, dot pitch illumination, or the like. The light-emitting element can be applied to a planar light source, an array display device, a backlight of a liquid crystal display device, a [photoelectric conversion element] π 褥秧兀仵, usually having an anode, a ruthenium etch, and a charge separation layer at the anode and the cathode between. Photoelectric conversion = ^ : and the cathode, in addition to the charge separation layer, may also have a 丄t layer, the above metal complex or the layer of the above composition layer 4, the coffee contains __ outside ^= 324066 201245157 It is preferably contained in the charge separation layer. The materials or specific examples of the cathode and the anode are the same as those described for the light-emitting element. The shape of the cathode cathode is not limited to (4) and may be a tooth comb type. The anode and cathode can also be either transparent or translucent. In the charge separation layer of the photoelectric conversion element, an electron-donating compound and an electron-accepting compound are usually contained. As the electron-donating compound, for example, a total of a polymer compound can be mentioned. Examples of the conjugated polymer compound include a thiophene diyl group-containing co-light polymer compound and a second group-containing polymer compound compound 0 as an electron-acceptable compound, and examples thereof include fullerene and Fuller's derivative. The photoelectric conversion element is usually formed on a substrate. Specific examples and preferred examples of the substrate are the same as those described in the section of the light-emitting element. The photoelectric conversion element is preferably a solar cell. EXAMPLES Hereinafter, the present invention will be described in detail using examples. Hereinafter, in the 1H NMR and 13C NMR measurement, a 300 MHz NMR spectrum manufactured by Varian Co., Ltd. was used, and in the DART-MS measurement, the AccuTOF TLC (JMS-TIOOTD) manufactured by JEOL Ltd. was used. The ultraviolet visible spectrum was measured by an absorption spectrophotometer (manufactured by Varian, Cary 5E). The luminescence spectrum was measured at 363 nm as an excitation wavelength, and was measured with a fluorescence spectrophotometer (manufactured by Sakamoto Optical Co., Ltd., trade name: FP-6500). 324066 48 201245157 t The luminescence quantum yield is calculated by comparison with the luminescence quantum yield (55%) in a quinine IN sulfuric acid aqueous solution of a standard sample. • The excitation lifetime is determined by the fluorescence spectrophotometer (JBBINYV0N-SPEX, manufactured by the company, trade name: Fluorolog-Tau 3), and the excitation lifetime is obtained from the luminescence peak wavelength of the luminescence spectrum. The content (mass basis) of the sp3 carbon atom is determined by multiplying the number of SP3 carbon atoms in the metal complex by the atomic weight of the carbon atom by dividing the molecular weight of the metal complex. <Synthesis Example 1> The gin(2-benzox-sialradyl)amine was synthesized according to the description of [norganica chemica Acta 231, 109-114 (1995). Specifically, hydrazine-extended phenyldiamine, nitrotriacetic acid, and propylene glycol were obtained by heating under reflux at 144 to 154 ° C for 24 hours to obtain bis(2-benzimidazolylhydrazino)amine. <Example 1> (2-Benzimidazolylmethyl)amine (20〇11^, 0.49111111〇1), 3,5-di-tert-butylbenzyl bromide compound in an argon atmosphere in a flask (626 mg '2. 21 mmol) and pulverized calcium hydroxide (247 mg, 4.42 〇1) were added to the flask, and then dried dimethyl sulfoxide (5 mL) was added, and the mixture was stirred at room temperature for 2 hours. Thereafter, when the reaction liquid was poured into water, a precipitate was obtained. This precipitate was extracted 3 times with chloroform. After the extract was dried over anhydrous magnesium sulfate, the organic solvent was evaporated to give a yellow viscous liquid. The yellow viscous liquid is purified by an alumina chromatography analyzer (developing solvent hexane: chloroform = 1 丨 (volume ratio) to 1: 2 (volume ratio) to obtain a formula represented by the above formula (A-16). A viscous solid substance (155 mg, yield: 31 «. 324066 49 201245157 1H NMR (300 MHz, CDC1,) $ (ppm) = 7.56 (3H, m). 7.00-7.26 (12H, n 〇, 6.66 (6H, s), 5.21 (6H, s), 4.30 (6H, s), 1.01-1.37 (54H, m). 13 C NMR (75 MHz, CDC1,) 6 (ppm) - 151.5, 142.7 135.8, 135.7, 123.0, 122.3, 121.8, 120.7, 120.5, 120.0, Π0.7, 50.9, 47.6, 35.0, 31.6. DART-MS 1014.76 Da (calcd. as [M+H]* 1014.70 Da). Example 2> A suspension of tetrahydrogenated (250 mL) of bis(2-benzimidazolylhydrazinyl)amine (8·Og ' 19.6 mmol) was added to the flask under argon atmosphere, followed by potassium metal After the addition of (2. 3g, 55.8 mmol), the reaction mixture was stirred for 2 hours. Stirring under reflux for 3 hours. After the reaction is completed, the reaction solution is cooled, and water is added. The liquid separation is carried out by extracting the water layer 'aggregate all the organic layer' under reduced pressure. The obtained concentrate is added with benzene and several times to carry out the concentration operation, and the residue is passed through an alumina chromatography analyzer (developing solvent hexane). : ethyl acetate = 3: 1 (volume ratio) to 1:1 (volume ratio) purified to obtain a yellow oily substance (5.7 g, yield: of the ligand (compound) represented by the above formula (A-17): 39%). lH NMR (300 MHz, CDCla) δ (ppm) = 7.74 &lt;3Η, m), 7.23 (9Η, πΟ, 4.03-4.34 (6Η, m), 3.24-3.43 (6Η, m), 1 ,52 (3H, m), 0.26-1.06 (42H, m). &quot;C NMR (75 MHz. CDC1,) 5 (ppm) = 151.5, 143.0, 135.6, 123.1, 122.5, 120.3, 110.3, 50.7, 48.0 , 39.1, 30.5, 29.1, 24.0, 23.0, 14.2, ni DART-MS 744, 59 Da (calcd. [M+H]* 744.66 〇a). <Example 3> The above formula (A-16) is shown The ligand, 〇. 083 〇 〇 1), and ruthenium (III) trifluoromethanesulfonate (24 mg, 〇. 〇 4lmm〇i) were added to the flask, and the inside of the flask was placed under argon to add dry ethanol ( 2小时), 324066 50 201245157 was mixed at room temperature for 2.5 hours to obtain a precipitate. This precipitate was suction-filtered and recovered, and recrystallized from methylene chloride and hexane to obtain a white solid material of the metal-form (43 mg, yield: 40%) of the above formula (B-11). * Elemental analysis

Found(%) C: 64.05, Η: 6.74, Ν: 7.31, S: 3.85. Calcdfor Cli, Hl74CeF»N1 «O^S, 1H,0 (%) C: 64.29, H: 6.73, N: 7.44, S : 3.65. The metal complex represented by the above formula (B-ll) is excited by ultraviolet light (365 nm), even in a solid powder state, even in a solution state (acetonitrile, ethanol, decyl alcohol, diphenylbenzene, toluene, gas imitation) Blue light is also emitted. The luminescence spectrum in acetonitrile has a peak at 436 nm, the luminescence quantum yield is 53%, and the excitation lifetime is 53.8 〇 <Example 4> The ligand represented by the above formula (A-17) (750 mg, 1. Olmmol), and difluoroanthracene acid (III) (289mg, 〇. 49mmol) was added to the flask, the flask was placed under argon atmosphere, dry ethanol (l〇mL) was added, and stirred at room temperature 2. 5 hours. When the reaction liquid was poured into a hexane, a sediment was obtained, and when the precipitate was recovered, a white solid (926 mg, yield: 91%) of the compound of the above formula (B-12) was obtained. Elemental analysis F〇und(») C: 57.02, Η: 6.59, Ν: 9.40. S: 4.98. Calcd for C99HlsgCeF9Nl409S3 (%) C: 57.29, H: 6.70, N: 9.45, S: 4.63. -12) The metal complex shown is excited by ultraviolet light (365 nm), and emits blue light even in a solid powder state even in a solution state (acetonitrile, ethanol, methanol, xylene, toluene, chloroform). The luminescence spectrum in acetonitrile 324066 51 201245157 has a peak at 437 nm, the luminescence quantum yield is 50%, and the excitation lifetime is 58. 9 ns. <Comparative Example 1> A metal complex represented by the following formula (C-1):

(C-1) Synthesized according to the record of Angew. Chem. Int. Ed. 46, 7399-7403 (2007). [Solubility test] The metal complex represented by the above formula (B-11), the metal complex represented by the above formula (B-12), or the metal complex represented by the above formula (C-1) is added to The solubility was observed in 0.5 mL of various organic solvents shown in Table 1. When the metal complex is not rapidly dissolved in the organic solvent at room temperature, the mixture of the metal complex and the organic solvent is heated while being brought close to the boiling point of the organic solvent, and then stirred, and returned to room temperature to observe the solubility. The results obtained are shown in Table 1. 324066 52 201245157 « Table 1

A: easy to dissolve (when the metal complex is added to the organic solvent, the metal complex dissolves quickly, and it is judged that there is no dissolved residue) 3, B · soluble (when the metal complex is added to the organic solvent, the metal steroid is completely dissolved It takes some time to judge the absence of dissolved residue. 3 ^ C: Insoluble (when the metal complex is added to the organic solvent, a part of the metal is dissolved, and it is determined that the residue remains) D ··Insoluble (adding the metal to the wrong body) In the case of an organic solvent, it was judged that the metal shoots were completely insoluble. According to Table 1, the metal complexes synthesized in Examples 3 and 4 exhibited high solubility for gas imitation, toluene, and diphenylbenzene in a nonpolar solvent. On the other hand, the metal complex synthesized in Comparative Example 1 exhibited low solubility for these non-polar solvents. Further, the metal complexes synthesized in Examples 3 and 4 exhibited high solubility in ethanol and acetonitrile of a polar solvent. <Example 5> 324066 53 201245157 A gas imitation is added to the metal complex lrog represented by the above formula (Β-ll), and the metal complex is dissolved in chloroform to prepare a 0 of the metal complex represented by the above formula (B_U). . 5 mass % solution. Using this solution, a film was formed on a glass substrate by spin coating at a speed of 100 rpm. The obtained film was measured by a stylus type film thickness meter (DEKTAk manufactured by Veeco Co., Ltd.), and it was confirmed that a uniform film of about 5 Å was obtained. <Example 6> Chloroform was added to 1 mg of the metal complex represented by the above formula (Β-ll), and the metal complex was dissolved in the gas to prepare a mass of the metal complex represented by the above formula (Β-ll). % solution. Using this solution, a film was formed on a glass substrate by spin coating at a speed of 1000 rpm. The obtained film was measured by a stylus type film thickness meter (DEKTAK manufactured by Veeco Co., Ltd.), and it was confirmed that a uniform film of about 25 Å was obtained. <Example 7> A mixed solution of chloroform and 1,2-dichloroethane in a mass ratio of 2/1 was added to 1 mg of the metal complex represented by the above formula (B-12) to dissolve the metal complex and prepare A 1% by mass solution of the metal complex represented by the above formula (B-12). Using this solution, a film was formed on the glass substrate by spin coating at a speed of 100 rpm. The obtained film was measured by a stylus type film thickness meter (DEKTAK manufactured by Veeco Co., Ltd.), and it was confirmed that a uniform film of about 120 nm was obtained. <Example 8> In the above formula (B-12), the metal complex and the polyvinylcarbazole (mass ratio 2/3) were added in 2.5 mg, and the mass of the gas and the bismuth, 2-diethane was added. The metal complex and the polyvinylcarbazole are dissolved in the mixed solution of 2/1 to dissolve the metal complex of the above formula (B_12) and the mass of the polyethylene 5 of the polyethylparaximate by dissolving the metal complex and polyvinylcarbazole in the mixed solution 324066 54 201245157 t. %mixture. Using this solution, a film was formed on the glass substrate by spin coating at a speed of &lt;100 rpm. The obtained film was measured by a stylus type film thickness meter (DEKTAK manufactured by Veeco Co., Ltd.) to confirm that a uniform film of about 40 nm was obtained. <Comparative Example 2> A chloroform was added to 1 mg of the metal complex represented by the above formula (C-1) to prepare a 1% by mass solution of the metal complex represented by the above formula (C-1), whereby a suspension was obtained. Using this suspension, a film was formed on the glass substrate by spin coating at a speed of 10 rpm. The obtained film was measured by a stylus type film thickness meter (DEKTAK manufactured by Veec Co., Ltd.), and the film thickness was not accurately obtained due to the uneven pattern of the multi-striped film. μ <Example 9> A π 〇 film having a thickness of 150 nm was formed on a glass substrate by a sputtering method, and in the same manner as in Example 6 under a nitrogen atmosphere, a thin film of the above formula (B_n) m was formed to have a thickness of about 50 nm. Then, a light-emitting element was produced by vapor-depositing lithium fluoride at about 5 nm and aluminum at about 80 nm as a cathode. When the light-emitting element was irradiated with ultraviolet light (365 nm), uniform blue light emission was observed from the light-emitting surface. <Example 10> A film of 150 μm thickness was formed on a glass substrate by a clock reduction method, and the same procedure as in Example 7 was carried out under a nitrogen atmosphere to prepare a metal-free compound and polyvinylcarbazole of the above formula 〇12. The thickness of the film is about 4 〇 nm, and then, lithium fluoride is about 〇5. 5 nm, and about 80 nm of aluminum is used as a cathode to prepare a light-emitting element. 324066 55 201245157 When the illuminating element is irradiated with ultraviolet light (365 nm), the self-illuminating surface is observed. To a uniform blue glow. (Industrial Applicability) The metal complex of the present invention has high solubility in a nonpolar solvent, and as a result, a metal complex which is easily formed by a coating method is used. Therefore, the metal complex of the present invention is borrowed. The coating method is extremely practical in the manufacture of organic electronic components. The metal complex of the present invention is also very useful as a material for magnetic materials, biological probes, contrast agents, additives, modifiers, and catalysts. [Simple diagram description] None [Main component symbol description] None 324066 56

Claims (1)

201245157 VII. Patent application scope: 1. A metal complex, which is a metal complex represented by the following composition formula (1): a M[L]a[X]b[L, ]〇, [in the formula (1), Μ denotes a cerium ion, a cerium ion, a mirror ion or a lutetium ion; L· represents a ligand represented by the following formula (2): / ^ (In the formula (2), A1, A2 and A3 are each Independently, means a hydrocarbon diyl group which may have a substituent, or a direct bond; \, L and L are each independently, representing a hydrogen atom or a ligand, but at least one of L, L and L3 is represented a heterocyclic group which may have a substituent as a ligand); X represents a counterion; L represents a single or double-dentate ligand; a is a positive number, and b and c are each independent, and more than 〇 When LX and L are plural, these may be the same or different, and the ratio of sp3 carbon atoms contained in the metal complex to the total mass of the metal complex is 22% by mass or more. The metal complex according to claim 1, wherein at least one of L2 and L is a group represented by the following formula (3) or (4), 324066 1 201245157 [In the formula (3), R6 represents a hydrogen atom, a hydrocarbon group which may have a substituent, or a heterocyclic group which may have a substituent; R7 represents -0', -C0 (T, -S〇3_, -ΗΡ0Γ, may have a hydrocarbon group of a substituent, a hydrocarbonoxy group which may have a substituent, a heterocyclic group which may have a substituent, a hydroxyl group, a carboxyl group, a sulfo group, or a phosphate group; j is an integer of 0 to 2; a nitrogen atom bonded to R6 and When the carbon atoms bonded to R7 are adjacent to each other, R6 and R7 may be bonded to each other and form a ring together with the nitrogen atoms and carbon atoms respectively bonded thereto; j is 2, and 2 R7 are bonded to carbon atoms adjacent to each other. 2 R7 can be combined with each other and form a ring together with the carbon atoms respectively combined; when j is 2, 2 R7 can be the same or different]; [In the formula (4), R8 represents -(Γ, -C0(T, -S〇3_, -ΗΡ0Γ, a hydrocarbon group which may have a substituent, a hydrocarbyloxy group which may have a substituent, a heterocyclic group which may have a substituent, 324066 2 201245157 t hydroxy, carboxyl, sulfo, or phosphate; k is an integer from 0 to 3; k is 2 or 3'. When multiple R8 is bonded to a carbon atom adjacent to each other, a plurality of R8 can be combined, and A ring is formed together with a carbon atom to be combined with each other; when k is 2 or 3, a plurality of R8s may be the same or different. 3. The metal complex according to claim 1 or 2, wherein Li, L2 and L3 are each independently a heterocyclic group which may have a substituent. 4. The metal complex according to any one of claims 1 to 3, wherein L is 15 to 2 Å. A metal complex according to the third or fourth aspect of the invention, wherein [is a ligand represented by the following formula (5), p (5) is independently a hydrocarbon atom which may have a nitrogen atom, may have a substituent, and may have a hydrocarbon group of 4 carbon atoms, or a heterocyclic group which may have a substituent having 4 or more sp 3 carbon atoms; And r14 are each independently and represent msG3, ., I, a substituent-based group, a heterocyclic group which may have a substituent _oxy group, may have a substituent of 324066 ', 201245157, a hydroxyl group, a carboxyl group, a sulfo group, or a phosphate group. ; R15, R16, R17, R18, R19 and R2° are each independently represent a hydrogen atom or a substituent; m, η and p are each independently an integer from 〇 to 2; when m is 2, two R12s may be the same They may also be different, and may be combined with each other and form a ring together with the carbon atoms respectively combined; when η is 2, two R13s may be the same or different, may be combined with each other, and form together with the carbon atoms respectively bonded thereto. Ring; When Ρ is 2, two Rus may be the same or different, and may be combined with each other and form a ring together with the carbon atoms respectively bonded thereto. The metal complex according to claim 5, wherein B is a ligand represented by the following formula (6), r and R2m each independently represent a hydrocarbon group having 4 or more sp3 carbon atoms which may have a substituent, or a heterocyclic group having at least one sp3 carbon atom which may have a substituent. The metal complex according to any one of claims 1 to 6, wherein Μ represents a decorative ion. The metal complex as described in any one of claims 1 to 7 of the patent application, 324066 4 201245157 I wherein a is 2 and c is 〇. 9. A composition comprising a metal complex as claimed in the scope of the patent application, and a charge transport material. 10. An organic film comprising a metal complex as described in the scope of the patent application. Any one of items 1 to 8 according to any one of the items 8 to 11. An organic electronic component comprising the metal complex according to the first aspect of the patent application. 12. A compound represented by the following formula (5), Among the items 1 to 8, [in the formula (5), R9, R1. And R&quot; are independently a hydrogen atom, a hydrocarbon group having four or more sp3 carbon atoms which may have a substituent, or a heterocyclic group having four or more sp3 carbon atoms which may have a substituent; R12, R13 and R14 They are each independently and represent one 〇-, one c 〇〇-, s 〇 3 _, _Hp 〇 4 _, a hydrocarbon group which may have a substituent, a hydrocarbon group which may have a substituent, a heterocyclic group which may have a substituent, a hydroxyl group, Carboxyl, sulfo, or phosphoric acid. R15, R'~, R19 and R2. Is independent of each other, indicating a hydrogen earth atom or a substituent; m, n and p are independent, an integer from 〇 to 2; 324066 201245157 m is 2, two R12 may be the same or different, and may be combined with each other. And forming a ring together with the carbon atoms respectively combined; when η is 2, two R13s may be the same or different, may be combined with each other, and form a ring together with the carbon atoms respectively combined; when ρ is 2, 2 R14 may be the same or different and may be bonded to each other and form a ring together with the carbon atoms respectively bonded thereto. 13. The compound according to claim 12, which is represented by the following formula (6), In the formula (6), R21, R22 and R23 are each independently a hydrocarbon group having four or more sp3 carbon atoms which may have a substituent, or a heterocyclic group having four or more sp3 carbon atoms which may have a substituent. ]. 324066 6 201245157 IV. Designated representative map: (1) The representative representative of the case is: (). (There is no picture in this case) (2) The symbol of the symbol of this representative figure is simple: (none) 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: M[L]a[X]b[L ,]c 324066