TW201211203A - High polymer compound, composition, liquid composition, thin film and element containing the high polymer compound, and surface light source and display device having the element - Google Patents

Abstract

An objective of this invention is to provide a material for forming an organic electroluminescence element or the like having long service life. A composition of this invention contains a high polymer compound containing a repeating unit represented by the following formula (1) and a repeating unit represented by the following formula (2), and at least one material selected from a group consisted of the high polymer compound, hole transport materials, electron transport materials and light emitting materials.

Description

[Technical Field] The present invention relates to a polymer compound, a polymerized human composition, a liquid grade product, a film and an element, and a light source and a display device. [Prior Art] A light-emitting element comprising a composition in which a luminescent organic metal-doping compound (Dopant) is doped to a host material is used as a hair/drag material, and is known to exhibit high-efficiency luminescence characteristics. (Special ^ [previous technical literature] defeated 1). [Patent Document 1] [Patent Document 1] Japanese Laid-Open Patent Publication No. 2010-31246 (Description of the Invention) However, in Patent Document 1, it is used to fabricate an organic electroluminescent element (Organic Electroluminescent Element) ( In the case of a light-emitting element such as "organic EL element" or the like, a material having a long life of the element is not specifically described. Accordingly, an object of the present invention is to provide a material which has a long life when used to produce a light-emitting element such as an organic EL element. (Means for Solving the Problem) The present invention provides the following [1] to [2〇]. U] - a polymer compound comprising a repeating unit represented by the formula (1) and a repeating unit represented by the formula (2), 4 323308 (1) 201211203

R4 and R5 each independently represent a hydrogen atom, an alkyl group, an aryl group, an aryloxy group, a thiol group, an arylalkyl group, an aryloxy group, an arylsulfanyl group, a fluorenyl group, a decyloxy group, Anthracene, an imide (imid # imide) group, an imine residue, a substituted fluorenyl group, a substituted fluorenyloxy group, a substituted oxathio group, a monovalent aromatic heterocyclic group, a heteroaryloxy group, At least one of a heteroarylthio group, an Arylalkenyl group, an Arylalkynyl group, a substituted sulfo group or a cyano group 'R1, R2, R3, R4 and R5 represents a group other than a hydrogen atom, R1. Adjacent groups of R2, R3, R4 and R5 may be bonded to each other to form a ring;

An and An are each independently represented to have an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an aralkyloxy group, an aryl group. Alkylthio, fluorenyl, decyloxy, decylamino, quinone imine, imine residue, substituted sulphate, substituted sulphate oxy, substituted sulphur, valence aromatic a ring group, a heteroaryloxy group, a heteroarylthio group, an arylene group, a substituent, and a substituent in the group k composed of a cyano group 2 2 323 308 5 201211203

(in the formula,

An represents an aryl group or a monovalent aromatic heterocyclic group;

An represents a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an aralkyloxy group, an arylalkylthio group, a Φ fluorenyl group. , anthraceneoxy, decylamino, oximine, imine residue, substituted amine, substituted fluorenyl, substituted fluorenyloxy, substituted thiol, substituted fluorenylamine, i-valent aromatic Cyclo, heteroaryloxy, heteroaryl fluorenyl, aralkenyl, arylalkynyl, substituted carboxy or cyano; R6 represents alkyl, alkoxy, alkylthio, aryl, aryloxy , arylthio, arylalkyl, aralkoxy, arylalkylthio, decyl, decyloxy, decylamino, quinone imine, imine residue, substituted amine, substituted hydrazine a substituted thioloxy group, a substituted thiolthio group, a substituted fluorenylamino group, an anthracene aromatic heterocyclic group, a heteroaryloxy group, a heteroarylthio group, an aralkenyl group, an aryl group, a substituted carboxyl group Or cyano; when there are a plurality of R6, these may be the same or different; a represents 0 or 1, and the two a's present may be the same or different). [2] The polymer compound according to [1], wherein at least one of R1, R2, R3, R and R5 is a group containing an alkyl group, and the above-mentioned fat containing an alkyl group in a group of a group The family carbon number is 6 or more. [3] The polymer compound according to the above [1], wherein at least one of ri, r2, 6 323308 201211203 R3, R and R5 is an alkyl group having 12 or more carbon atoms. [4] The polymer compound according to [1] or [2] wherein the above-mentioned r2 and r4 are an alkyl group-substituted aryl group. [5] The polymer compound according to any one of [1] to [4] wherein the above-mentioned An-based hydrogen atom, alkyl group, aryl group or anthracene aromatic heterocyclic group. [6] The polymer compound according to any one of [1], wherein the An and An are independently a divalent aromatic compound represented by the formula (3) or the formula (4). base,

(wherein 'R' represents a hydrogen atom or an alkyl group). The polymer compound according to any one of [1] to [6], wherein the repeating unit of the above formula (2) is repeatedly read by the above formula (1) with respect to all the repeating units of the polymer compound. The total ratio is 30% or more. [8] The polymer compound according to any one of [1] to [7] which contains a repeating unit represented by the formula (5), ~ Ars--(5) (wherein, Ars represents an extension An aryl group or a divalent aromatic heterocyclic group). [9] The polymer compound according to [8], wherein the repeating unit represented by the above formula (5) is a repeating unit represented by the formula (6), (R7)a (R7)a

(in the formula,

An and An each independently represent an alkyl group, an alkoxy group, an alkylthio group, a aryloxy group, an arylthio group, an arylalkyl group, an aralkyloxy group, an arylalkylthio group, a fluorenyl group. , anthraceneoxy, decylamino, quinone imine, imine residue, substituted amine, substituted fluorenyl, substituted fluorenyloxy, substituted thiol, substituted fluorenyl hydroxy, hetero Alkylthio, aryl, aralkynyl, substituted fluorenyl or cyano; R7 represents alkyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, aryl Alkyl, aryloxy, arylalkylthio, aryl, aryloxy, uglyamino, oximine, imine residue, substituted amine, substituted fluorene substituted decyloxy, substituted Sulfhydryl, substituted mercaptoamine, monovalent aromatic hetero, heteroaryloxy, heteroarylthio, aryl, aryl, substituted carboxy or cyano; a represents hydrazine or丨, the two a's present may be the same or different; when there are multiple R?, these may be the same or different). = 高分子 [δ], wherein the compound represented by the above formula (5) is selected from the group consisting of a repeating unit of the formula (7) and a repeat of the formula (8), 323308 8 201211203

Ra

(7) (wherein R8 and R9 each independently represent an alkyl group, an alkoxy group, a alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an aralkyloxy group, an aryl group Alkylthio, fluorenyl, decyloxy, decylamino, quinone imine, imine residue, substituted amine, substituted fluorenyl, substituted fluorenyloxy, substituted thiol, substituted fluorenylamino , a monovalent aromatic heterocyclic group, a heteroaryloxy group, a heteroaryl #ylthio group, an aralkenyl group, an arylalkynyl group, a substituted carboxy group or a cyano group) R10 Τ'ήτ (8) CR11)b (wherein R and R-series independently represent an alkyl group, an alkoxy group, a thiol group, an aryl group, an aryloxy group, an arylthio group, an aryl group, an aryloxy arylsulfonyl group, a brewing group, Alkoxy, aramidyl, alkynyl, an imine residue, a substituted amine, a substituted alkaloid, a substituted fluorenyloxy, a substituted oxathiol, a substituted arylamino group, a valence An aromatic heterocyclic group, a heteroaryloxy group, an arylthio group, a starting group 3, a tilting group or a secret; b represents a polymer as described in [8] to [10] & a compound in which all of the compounds are In the complex unit, the total ratio of the repeating unit represented by the formula (2) and the repeating unit represented by the formula (5) represented by the formula (1) is 80 mol% or more. For example, [1] to [11]^- The polymer compound, wherein 323308 201211203 contains a repeating unit represented by the formula (9), / ^8_^ΑΓι_^ΑΓιοΛ_ \ "9 A" 11 /(9)

(wherein, An, An, Ano and Aru each independently represent an aryl group or a divalent aromatic heterocyclic group; and Aru, VIII]: 12 and Αη3 each independently represent an aryl group or a monovalent aromatic group. Heterocyclyl; \ and oxime each independently represent 〇 or 1, but the value of x + y is 〇 or 1). [13] A composition comprising: the polymer compound according to any one of [12] to [12] and at least one selected from the group consisting of a hole transporting material, an electron transporting material, and a light emitting material. A material. [14] The composition according to [13], wherein the luminescent material contains a luminescent organometallic complex compound. [15] A liquid composition comprising the compound of the ruthenium compound according to any one of [1] to [12], and a solvent or a dispersion medium. [16] A film which comprises the polymer compound according to any one of [1] to [12]. [17] An element comprising an electrode composed of an anode and a cathode, and an organic layer containing the polymer compound according to any one of [1] to [12]. [18] A planar light source comprising the component described in [17]. [19] A display device comprising the component described in [17]. 10 323308 201211203 [20] - a compound of the formula (i),

(wherein, Ra, Rf and Rg each independently represent a hydrogen atom or an alkyl group, and Rb, Re, Rd and Re each independently represent an alkyl group or an alkyl-substituted aryl 9 group; and An and An are each independently The representation may have an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an aralkyloxy group, an aryl group thio group, a fluorenyl group. , anthraceneoxy, decylamino, arylimine, imine residue, substituted fluorenyl, substituted fluorenyloxy, substituted thiol, fluorene aromatic heterocyclic, heteroaryloxy, hetero a divalent aromatic group of a substituent in the group consisting of an arylthio group, an aralkenyl group, an aralkynyl group, a substituted carboxyl group, and a cyano group; X represents a halogen atom, a boronic acid ester residue, a boronic acid residue, and a formula (a, the base of the formula, the group represented by the formula (a_2), the group represented by the formula (a-3) or the base represented by the formula (a_4) may be the same or different)

T (a-1) (wherein RT represents an alkyl group or an aryl group) - MgXA (a-2) (wherein XA represents a halogen atom) 323308 11 201211203 - ZnXA (2r3) (wherein XA represents the foregoing Synonymous) —Sn(RT)3 (a-4) (wherein RT means synonymous with the foregoing, and the three RTs present may be the same or different). (Effects of the Invention) The polymer compound and the composition of the present invention (hereinafter also referred to as "the polymer compound of the present invention m") are used for producing an organic EL device or the like, and have a long life. In a preferred embodiment, the polymer compound of the present invention or the like can provide an element having excellent luminous efficiency (i.e., high quantum yield). Therefore, the polymer compound of the present invention or the like is particularly useful for the production of a light-emitting element such as an organic EL device. [Embodiment] Hereinafter, the present invention will be described in detail. φ [Description of Terms] The following is a description of the common lingua franca used in this manual. In the case of a halogen atom, an atom, a chlorine atom, a desert atom, and a moth atom can be exemplified. The "repeating unit" means that two or more units are present in the polymer compound. In the phrase "Cm to Cn" (m and η satisfy a positive integer of m < η), it is indicated that the number of carbon atoms of the organic group after the term is m to η. 12 323308 201211203 The term "unsubstituted" in the context of a radical means that the hydrogen atom of the radical is unsubstituted. The term "substitution (substitution)" attached to the front of the radical means that some or all of the hydrogen atoms of the radical are replaced by substituents. The term "may have a substituent" attached to the front of the group means both the case where the hydrogen atom of the group is unsubstituted, and the case where a part or all of the hydrogen atom of the group is substituted with a substituent. . The phrase "may have a substituent" in the term "can be replaced". In the case of a substituent, unless otherwise specified, a halogen atom, a carbon atom, a hydrocarbon group of 1 to 30, and a hydrocarbyloxy group having 1 to 30 carbon atoms are exemplified. A halogen atom, a hydrocarbon group having 1 to 18 carbon atoms, and a hydrocarbonoxy group having 1 to 18 carbon atoms are preferred, and a halogen atom, a hydrocarbon group having 1 to 12 carbon atoms, and a hydrocarbon group having 1 to 12 carbon atoms are preferred. More preferably, a halogen atom and a hydrocarbon group having 1 to 12 carbon atoms are more preferable, and a halogen atom and a hydrocarbon group having 1 to 6 carbon atoms are particularly preferable. The alkyl group means an unsubstituted alkyl group and an alkyl group substituted with a substituent such as a functional atom, an amine group and a mercapto group. The alkyl group contains both a linear group and a cyclic alkyl group (cycloalkyl group). The alkyl group can have a branch. The number of carbon atoms of the alkyl group is usually from 1 to 20 in the case where the number of carbon atoms of the substituent is not contained. Examples of the alkyl group include mercapto, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclohexyl, heptyl, octyl, 2 _Ethylhexyl, fluorenyl, fluorenyl, methyl eleven, fifteen, 2, 2, 4, 4, 6, 8, 8-heptyl fluorenyl, heptadecyl, octadecyl, 2 , 6, 10, 14-tetradecylpentadecyl, 19-yl, 3,7-dimethyloctyl, dodecyl, trifluoromethyl, pentafluoroethyl, perfluorobutyl, perfluorohexyl , perfluorooctyl, three 13 323308 201211203 fluoropropyl, decafluoro-1,1,2,2~tetrahydrooctyl, heptafluoro-1,1,2,2-tetrahydroindenyl, decyl-propyl Base, fluorenyl octyl and sulfhydryl. The hydrazine to C2 decyl group may, for example, be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a second butyl group, a tert-butyl group, a pentyl group or an isopentyl group. , hexyl, cyclohexyl, heptyl, octyl, decyl, fluorenyl and decyl. The alkoxy group means an unsubstituted alkoxy group and an alkoxy group substituted with a substituent such as a functional atom and an alkoxy group. The alkoxy group includes both a linear alkoxy group and a cyclic alkoxy group (cycloalkoxy group). The alkoxy group can have a branch. The carbon number '# subunit of the alkoxy group is usually from 1 to 20, preferably from 1 to 15, more preferably from 1 to 10, in the case of the number of carbon atoms having no substituent. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, a third butoxy group, and a pentyloxy group. , hexyloxy, cyclohexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, 3,7-dimethyloctyloxy, Dodecyloxy, trifluoromethoxy, pentafluoroethoxy, perfluorobutoxy, perfluorohexyl, perfluorooctyl, nonyloxyalkyloxy and 2-decyloxyethyloxy base. Examples of the fluorene to C12 alkoxy group include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutoxy group, a third butoxy group, and a pentyl group. Oxy, hexyloxy, cyclohexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, decyloxy, decyloxy, 3,7-dimethyloctyloxy Base and 12 alkyloxy groups. The alkylthio group means an unsubstituted alkylthio group and an alkylthio group substituted with a substituent such as an il atom. The alkylthio group includes both a linear alkylthio group and a cyclic alkylthio group (cycloalkylthio group). The alkylthio group can have a branch. Burning 14 323308 201211203 The number of carbon atoms of the thiol group, in the case of the number of carbon atoms without a substituent; the brother is usually 1 to 20', preferably 1 to 15, more preferably 1 to 1CN, For example, mercaptothio, ethylthio, propyl bowl isopropylthio, butylthio, isobutylthio, tert-butylthio, pentylthio, hexylthio , cyclohexylthio, heptylthio, octylthio,

2-ethylhexylthio <'merylthio, decylthio, 3,7-dimethyloctylthio, dodecylthio and trifluoromethylthio. Examples of the (^ to h thiol meanings include a mercaptothio group, an ethylthio group, a propylthio group, a propylthio group, a butylthio group, an isobutylthio group, and a third group. Butylthio, pentylthio, hexylthio, cyclohexylthio, heptylthio, octylthio, ethylhexylthio, decylthio, decylthio, 3, 7- Dimethyloctyl and 12-alkylthio groups.

The aryl group removes an atomic group remaining from the aromatic hydrocarbon after bonding to a hydrogen atom constituting the carbon atom of the aromatic ring. The aryl group means an unsubstituted aryl group and an aryl group substituted with a substituent such as a halogen atom, an alkoxy group and an alkyl group. The aryl group also includes a condensed ring; two or more of the independent stupid ring and the condensed ring are bonded by an early bond; and two or more selected from the group consisting of an independent benzene ring and a condensed ring The number of carbon atoms bonded to a base by a divalent organic group (for example, a vinyl group or the like) is in the case of a carbon atom having no substituent: pass: 6 to 60, preferably 7 To 48, more preferably 7 to 3 inches. The aryl group is, for example, phenyl, &amp; to Cl2 alkoxyphenyl, Cl to Cl2j, bnaphthyl, 2'naphthyl, 1-3⁄4 (lUeenyD, 2-guanger-9, and pentafluorobenzene) The base is preferably a Q &amp; phenyl group or a &lt; to an alkyl group. 323308 15 201211203 In the case of a Cl to Cl 2 alkoxyphenyl group, for example, an anthracene group, an ethoxy group is exemplified. Phenyl, propyloxyphenyl, isopropyloxyphenyl, butoxyphenyl, isobutoxyphenyl, tert-butoxyphenyl, pentyloxyphenyl, hexyloxy Phenyl, cyclohexyloxyphenyl, heptyloxyphenyl, octyloxybenyl, 2-ethylhexyl base, fluorenyloxy, decyloxyphenyl, 3,7- Di-nonyloctyloxyphenyl and dodecyloxyphenyl. Examples of the Cl to Cl2 alkylphenyl group include a methylphenyl group, an ethylphenyl group, a dinonylphenyl group, and the like. Propyl phenyl, 2, 46-three 曱 基 # # (2, 4, 6-Mesityl), methyl ethyl phenyl, isopropyl phenyl, butyl phenyl, isobutyl benzyl, bismuth Phenylphenyl, pentylphenyl, isopentyl, hexyl, heptyl, octylphenyl Nonylphenyl, nonylphenyl and dodecylphenyl. The aryloxy group means an unsubstituted aryloxy group and an aryloxy group substituted with a substituent such as a halogen atom, a decyloxy group and an alkyl group. The number of carbon atoms of the aryloxy group is usually 6 to 6 Å, preferably 7 to 48, more preferably 7 to 30, in the case of the number of carbon atoms having no substituent. For example, a phenoxy group, a hydrazine to a U alkoxyphenoxy group, (:, a G2 alkyl phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a pentafluoro group, and a pentafluoro group are mentioned. The base group is preferably (:! to L alkoxyphenoxy group or (^ to Cu alkylphenoxy group). For the Ci to C 2 alkoxyphenoxy group, for example, hydrazine is exemplified. Oxylooxy, ethoxyphenoxy, propyloxyphenoxy, isopropyloxyphenoxy, butoxyphenoxy, isobutoxyphenoxy, tert-butoxy Phenoxy, pentyloxyoxy, hexyloxyphenoxy, cyclohexyloxyphenoxy, 323308 16 201211203 2-ethylhexyloxyphenoxy, '3,7-dimethyloctyl Hydroxyheptyloxyphenoxy, octyloxyphenoxy Nonyl phenoxy group, decyloxy and phenoxy groups, and dodecyl phenoxy group.

Examples of the G to C1Z alkylphenoxy group include methylphenoxy, ethylphenoxy, dimethylphenoxy, propylphenoxy, and 13,5-trimethylphenoxyl. , methyl ethyl phenoxy, isopropoxy group, butyl phenoxy, + isobutyl methyloxy, tert-butoxy, silk phenoxy, isopentyl phenoxy, hexyl benzene Oxyl, heptylphenoxy, octylphenoxy, nonylphenoxy, nonylphenoxy and dodecyloxy. The arylthio group means an unsubstituted arylthio group and an arylthio group substituted with a substituent such as a halogen atom, an alkoxy group and an alkyl group. The carbon number of the arylthio group is usually 6 to 10, preferably 7 to 48, more preferably 7 to 30, in the case of the number of carbon atoms not containing a substituent. Examples of the arylthio group include a strepylthio group, (^ to a Cu alkoxyphenylthio group, (^ to &amp; alkylalkylthio group, 1-naphthylthio group, 2- A naphthylthio group and a pentafluorophenylthio group. An arylalkyl group means an unsubstituted arylalkyl group and an arylalkyl group substituted with a substituent such as a dentate atom, an alkyl fluorenyl group and an alkyl group. The number of carbon atoms, in the case of the number of carbon atoms not containing a substituent, is usually from 7 to 1, preferably from 7 to 48, more preferably from 7 to 30. Examples of the arylalkyl group include, for example: Phenyl-(^ to C2.alkyl, (^ to Clz alkoxyphenylindole! to. alkyl, (^ to C! 2 alkylphenyl-(^ to C2. alkyl, naphthyl-(^) To C2()alkyl and naphthyl-Cl to C20. A aryloxy group means an unsubstituted aryloxy group and an aralkoxy group substituted with a substituent such as a tooth atom, a oxime group or an alkyl group. The carbon atom of the aralkyloxy group is 323308 17 201211203. In the case of the number of carbon atoms having no substituent, it is usually 7 to 6 Torr, and the ruthenium is preferably 7 to 48, more preferably 7 to 3 Å. The alkoxy group may, for example, be a phenyl-hydrazine to a (:12 alkoxy group, d &amp;oxyalkylene to l-oxyl, c] to c12 alkyl phenyl-hydrazine to Ci2 alkoxy, broccoli { to b alkoxy and 2-naphthyl-(^ to (: The alkoxy group means an unsubstituted arylalkylthio group and an arylalkylthio group substituted with a substituent such as a tooth atom, an alkoxy group or a decyl group. The number of carbon atoms of the group 'in the case of the number of carbon atoms having no substituent, _ is usually from 7 to 60, preferably from 7 to 48, more preferably from 7 to 3 Å. With an arylalkylthio group For example, phenyl-Ci to G-based thio, &amp; to C1Z alkoxyphenyl to clz alkylthio, Cl to Ci2 alkylphenyl-Ci to C! 2 alkylthio , naphthyl-(^ to Ciz alkylthio and 2-naphthyl-hydrazine to Cl2 alkylthio. Aromatic alkenyl means unsubstituted aralkenyl and substituents such as halogen atom, alkyl fluorenyl group and alkyl group The substituted fluorenyl group. The carbon number of the base is usually from 8 to 60, preferably from 8 to 48, more preferably from 8 to 30, in the case of the number of carbon atoms not containing the φ substituent. The alkenyl group may, for example, be a phenyl group to a U-alkenyl group or a fluorenyl group. The alkoxyphenyl-anthracene to &amp; Base, oxime to Ci2 alkyl phenyl-G to C! 2 alkenyl, 1-naphthyl- fluorene to &amp; alkenyl and 2-naphthyl-C2 to C! 2 alkenyl, Ci to C! 2 alkane The oxyphenyl-(^ to &amp; alkenyl group or the g to 匕2 alkylphenyl-C2 to Cl2 dilute group is preferred. Examples of the fluorenyl group to the alkenyl group include a vinyl group and a propylene group. 2-propenyl, 1-butenyl, 2-butenyl, i-pentenyl, 2-pentenyl, 1-hexenyl, 2-hexenyl and 1-octenyl. 323308 18 201211203 Aralkyne means an unsubstituted alkynyl group and an aryl block group substituted with a substituent such as a - atom, an alkoxy group and a decyl group. The number of carbon atoms of the aryl group is usually 8 to 6 Å, preferably 8:48 Å or more preferably 8 to 30, in the case of the number of carbon atoms of the substituent. Examples of the aralkynyl group include a phenyl futon-7 to C alkynyl group, (^ to a Clz alkoxyphenyl seven to an alkynyl group, an anthracene to an alkylphenyl fluorene 2 to an alkynyl group). , 丨-naphthyl-(^ to Ciz alkynyl and 2-naphthyl-^ to c12 alkynyl, preferably (^ to L alkoxyphenyl 2 to &amp; alkyne &amp; alkylphenyl-fluorene To the alkynyl group, the C2 to Cl2 alkynyl group may, for example, be an ethylidene-based small-propyl group, a 2-propyl group, a 1-butynyl group, a 2-butynyl group or a pentynyl group. 2 pentanyl, 1-hexynyl, 2-hexynyl and octynyl. Heteroaryloxy means unsubstituted heteroaryloxy and substituted heteroaryloxy. The number of carbon atoms of the oxy group is usually 6 to 6 Å, preferably 7 to 48, in the case of the number of carbon atoms having no substituent. The heteroaryloxy group is 5, and for example, Cl to l alkoxypyridyloxy, Q to &amp; φ alkyl pyridyloxy, thienyloxy, fluorenyl. alkoxythiophenyloxy, σ aryloxy and isoindolyloxy Preferably, it is preferably a pyridyloxy group or a Cl to a C 2 alkyl group which is preferably a pyridyloxy group. Examples of the oxy group include a methoxy group, a methoxy group, an ethoxy group oxy group, a propyloxy group K oxy group, an isopropyloxy group, a butyl group, and a butyl group. Oxyl is a pyridyloxy group, isobutoxy 0 is a butyloxy group, a second butoxy group is a pyridyloxy group, a third butoxy acridineoxy group, a pentyloxy group is a pyridyl group. Alkoxy, hexyloxyacridinyloxy, cyclohexyloxydecyloxy, heptyloxypyridyloxy, octyloxytadineyl 19 323308 201211203 Oxyl, 2-ethyl Hexyloxy-based oxy, decyloxy oxime than butyloxy, decyloxy 11-pyridyloxy, 3,7-dimethyloctyloxy. Pyridyloxy and dodecane The hydroxy group is a pyridyloxy group. Examples of the Cl to Cl 2 alkyl a pyridyloxy group include a methylpyridinyloxy group, an ethyl acridineoxy group, and a dimethyl 0 ratio. Pyridyloxy, propyl acridineoxy, 1,3,5-trimethyloxaridinyloxy, methylethylpyridinyloxy, isopropylacridinyloxy, butyl Π-pyridyloxy, isobutyl, pyridyloxy, t-butyl acridineoxy, Butyl acridineoxy, pentyl® β-pyridyloxy, isopentylpyridinyloxy, hexyl acridineoxy, heptyl aridyloxy, octyl acridineoxy , fluorenyl η is a pyridyloxy group, a fluorenyl fluorenyl group, and a decyloxy group. The heteroaryl thio group means an unsubstituted heteroaryl thio group and a substituted heteroaryl group. The number of carbon atoms of the heteroarylthio group, in the case of the number of carbon atoms having no substituent, is usually from 6 to 60, preferably from 7 to 48. In the case of a heteroarylthio group, For example: acridinylthio, indole to alkoxypyridylthione, Cl to Cl2 alkylpyridylthio and isoquinolinylthio, from Cl to C1Z alkoxypyridylthio or (^ to &amp;alkylpyridylthio group is preferred. The monovalent aromatic heterocyclic group means that the atomic group remaining after the removal of one hydrogen atom directly bonded to the aromatic ring from the aromatic heterocyclic compound also contains a condensed ring. The monovalent aromatic heterocyclic group means an unsubstituted monovalent aromatic heterocyclic group and an anthracene aromatic heterocyclic group substituted with a substituent such as an alkyl group. The quinoid compound refers to an organic compound having a cyclic structure, and the element constituting the ring includes not only a carbon atom but also a hetero atom such as an oxygen atom, a sulfur atom, a nitrogen atom, a phosphorus atom, a boron atom or a ruthenium atom. Examples of the heterocyclic compound having an aromatic character of 323308 20 201211203 include ruthenium bismuth, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphonic acid isoquinoline, carbazole and diphenyl. And a heterocyclic compound containing a hetero atom such as Dibenzophosphole, and the heterocyclic ring itself exhibits aromaticity; Phenoxazine, Phenothiazine, dibenzoxene a heterocyclic compound containing a hetero atom such as Dibenzoborole, Dibenzosi lole, and Dibenzopyran, and the compound contains a hetero atom. Although the % by itself does not exhibit a square fragrance, it is a structure in which a heterocyclic ring has an aromatic ring through a condensed ring. The number of carbon atoms of the monovalent aromatic heterocyclic group is usually 4 to 60, preferably 4 to 30, in the case of the number of carbon atoms having no substituent. The monovalent aromatic heterocyclic group may, for example, be a thienyl group, a (^ to a C 2 alkyl fluorenyl group, a fluorenyl group, a furyl group, a pyridyl group, a Cl to a C 2 alkyl pyridyl group, a taki group. , mouth, thiol, pyridyl, tri-negative, quinolinyl and isoquinolyl, with ° thiophene, hydrazine to C! 2 alkylthiophenyl, pyridyl or hydrazine to C12 alkyl pyridinyl Preferably, an amine group means an unsubstituted amine group and an amine group substituted with one or two substituents selected from the group consisting of an alkyl group, an aryl group, an aryl group and a monovalent aromatic heterocyclic group (hereinafter referred to as "Substituted amine group". The substituent may have a substituent (hereinafter also referred to as "secondary substituent"). The number of carbon atoms of the substituted amine group is in the number of carbon atoms without a secondary substituent. In the case, it is usually from 1 to 60, preferably from 2 to 48', more preferably from 2 to 4 Å. Examples of the substituted amino group include a methylamino group, a dimethylamino group, an ethylamino group, Diethylamino, propylamine 21 323308 201211203 base, dipropylamino, isopropylamino, di-isopropylamino, butylamino, isobutylamino, secondbutylamine Base Tributylamino, pentylamino, hexylamino, heptylamino, octylamino, 2-ethylhexylamino, decylamino, decylamino, 3,7-dimethyl Octylamino, dodecylamino, cyclopentylamino, dicyclopentylamino, cyclohexylamino, dicyclohexylamino, bis(trifluoromethyl)amino, phenylamino , diphenylamino, fluorene to C12 alkoxyamino group, mono(Cl to Cl2 alkoxyphenyl)amine group, Cl to Cl 2 base group Fee group, one (Ci to Ci2 alkyl phenyl group) Amino, 1-caminoamine, 2-cetamamine®, pentafluorophenylamino, pyridylamino, decylamino, pyrimidinylamino, pyridylamine, tri-pound amine , phenyl-C, to C12 alkylamino, hydrazine to C1Z alkoxy phenyl-hydrazine to C! 2 alkylamino, bis((^ to C12 alkoxyphenyl-(^ to cumane) Amino group, hydrazine to C12 alkylphenyl-fluorene to C12 alkylamino group, di-C! 2 alkyl phenyl 7-C12 alkyl) amine group, 1-naphthyl to Ci2 alkylamino group and 2-nyl-Ci to Ci2 alkylamino. fluorenyl means unsubstituted fluorenyl and selected from alkyl, aryl, aryl φ alkyl and monovalent aromatic a mercapto group substituted by one, two or three substituents of a fragrant heterocyclic group (hereinafter referred to as "substituted fluorenyl group"). The substituent may have a secondary substituent. The number of carbon atoms of the substituted fluorenyl group is not In the case of the number of carbon atoms containing a secondary substituent, it is usually 1 to 6 Å, preferably 3 to 48, more preferably 3 to 40. Examples of the substituted fluorenyl group include a trimethyl fluorenyl group. Triethyl decyl, tripropyl decyl, tri-isopropyl fluorenyl, dimethyl-isopropyl decyl, diethyl-isopropyl decyl, tert-butyl decyl dimethyl hydrazine , pentyl dimethyl fluorenyl, hexyl dimethyl fluorenyl, heptyl dimethyl fluorenyl, octyl dimethyl fluorenyl, 2-ethylhexyl dimethyl fluorenyl, fluorenyl fluorenyl Mercapto, fluorenyl 2 22 323308 201211203 methyl sylvestre 3, 7-monomethyloctyl-dimethyl sylylene, dodecacarbonyl dimethyl fluorenyl, phenyl-hydrazine to G alkyl hydrazine Base, 〇 to. Alkoxyphenyl to

Ci2-based thiol Ci to Ci2 phenylphenyl-Ci to Ci2 alkyl, 1-naphthyl anthracene to C1Z alkyl fluorenyl, 2-naphthyl-(^ to Cu alkyl fluorenyl, phenyl- 〇到

Cl2 alkyl dimethyl sulphate, triphenyl sulphate, tri-p-fluorenyl sulphate, trifoliate sylvestre, sylvestyl-methyl sulphate, tert-butyldiphenyl sulphate and dimethyl Phenyl fragment. &quot;Substituted fluorenyloxy means a group consisting of an alkyl group, an aryl group, an arylalkyl group, an alkanoyloxy group, a aryloxy group, an aryloxy group, and a monovalent heterocyclic oxy group One, two or three substituents substituted with a decyloxy group. The substituent may have a secondary substituent. The number of carbon atoms of the substituted fluorenyloxy group is usually from 丨 to 6 〇, preferably from 3 to 48, in the case of the number of carbon atoms which does not have a secondary substituent. Examples of the substituted fluorenyloxy group include a trimethyl fluorenyloxy group, a diethyl fluorenyloxy group, a tripropyl decyloxy group, a tris-isopropyl fluorenyloxy group, and a dimethyl group. -isopropyl isopropyloxy, diethyl-isopropyl decyloxy, φ second butyl dimethyl fluorenyloxy, pentyl dimethyl fluorenyloxy, hexyl decyl fluorenyl Oxyl, heptyl dimethyl fluorenyloxy, octyl decyl fluorenyloxy, 2-ethylhexyl-dimethyl fluorenyloxy, fluorenyl fluorenyl fluorenyl, fluorenyl Dimethyl decyloxy, 3, 7-dimethyloctyl-diindenyloxy, dodecyl bis-decyloxy, phenyl-hydrazine to c12 alkyldecyloxy , ^ to C1Z alkoxyphenyl { to Cu alkyl decyloxy, oxime to &amp; alkyl phenyl-Cl to Cl 2 alkyl decyloxy, 1-naphthyl-Cl to Cl 2 alkyl fluorenyl Oxyl, 2-naphthyl to Cl2 alkyl nonyloxy, phenyl-c! to C! 2 alkyl dimethyl oxalyloxy, triphenyl fluorenyloxy, tri-p- fluorenyl Alkoxy group, ternary group 323308 23 201211203 Benthyl sulfhydryloxy, diphenylmethyldecyloxy, tert-butyl Silicon based groups and dimethylphenyl. Substituted thiolthio means to be selected from alkyl, aryl, #r* it A r* «· square base, burned

The m-thio group, the arylthio group and the i-valent heterocyclic thio group form one, two or three substituents substituted in the group. The substituent may have a secondary substituent. The number of carbon atoms of the substituted thiol group is usually from 丨 to 60, more preferably from 3 to 48, in the case of the number of carbon atoms which does not contain a secondary substituent. The substituted thiolthio group may, for example, be trimethylsulfonylthio, triethylsulfonylthio, tripropylsulfonylthio, triisopropylsulfonylthio, dimethyl- Isopropyl thiol, diethyl isopropyl isopropyl thio, tert-butyl bis yl 7 thio, pentyl dimethyl thio, hexyl dimethyl thiol, Heptyl dimethyl sulfhydryl thio, octyl dimethyl decyl thio, 2-ethylhexyl dimethyl thiol, decyl dimethyl thiol, decyl dimethyl Thiothio, 3, 7-dimethyloctyl-dimethyl oxathiol, dodecyldimethylsulfonylthio, phenyl-Ci to cardinyl hydrazine, thiol, hydrazine l alkoxyphenyl-c, to &amp;alkylmercaptothio, Ci to &amp; phenyl group to (: 12 alkyl sulfothio group, naphthyl-d &amp; decyl thiol , 2-naphthyl to C1Z alkylsulfonylthio, phenyl-Ci to Ci2 alkyl dimethyl fluorenylthio, triphenylsulfonylthio, tri-p-fluorenylthio, tribenzyl Base mercaptothio, diphenyldecylsulfonylthio, tert-butyldiphenylsulfanylthio and dimethylphenylindenyl The heterocyclic thio group means a group in which a hydrogen atom of a fluorenyl group is substituted with a monovalent aromatic heterocyclic group. Examples of the heterocyclic thio group include a heteroarylthio group (for example, pyridyl group). Sulfur-based, argon-based thio, pyrimidinylthio, pyrantylthio and tri-323308 24 201211203 thiolthio). Substituted mercaptoamine means selected from alkyl, aryl, arylalkyl a mercaptoamine group substituted with one, two or three substituents in the group consisting of an alkylamino group, an arylamine group, an arylalkylamino group and a monovalent heterocyclic amine group. It may have a secondary substituent. The number of carbon atoms of the substituted mercaptoamine group is usually from 1 to 6 Å, preferably from 3 to 48, in the case of the number of carbon atoms which does not contain a secondary substituent. The amine group can be exemplified by, for example, trimethyl sulphonylamino group, triethyl decylamino group, tripropyl decylamino group, tri-isopropyl fluorenylamino group, dimercapto-isopropyl ru Amino group, diethyl-isopropylpyridylamino group, tert-butyl decyl decylamino group, pentyl dimethyl decylamino group, hexyl dimethyl decylamino group, heptyl group Methyl decylamino Octyl dimethyl fluorenylamino, 2-ethylhexyl-dimethyldecylamino, decyl decyl decylamino, decyl dimethyl decylamino, 3, 7-di Methyloctyl-dimercaptoalkylamino, dodecyldimethylmethylamino, phenyl-G to Clz alkyldecyloxy, C! to Cl2 alkoxyphenyl-Cl to Cl2 alkyl mercaptoamine, G to Cl2 | alkyl phenyl-Cl to Cl 2 alkyl amide, 1-naphthyl-Cl to C12 alkyl sulfenyl, 2-naphthyl-Cl to Cl2 Pyridylamino group, phenyl-Cl to Cl2 alkyl dimethyl decylamino group, triphenyl decylamino group, tri-p-fluorenyl decylamino group, tribenzyl decylamino group, two Phenylnonylguanidinoamine, tert-butyldiphenyldecylamino and dimethylphenyldecylamino. The fluorenyl group means an unsubstituted fluorenyl group and a fluorenyl group substituted with a substituent such as a tooth atom. The number of carbon atoms of the mercapto group is usually from 1 to 20, preferably from 2 to 18, more preferably from 2 to 16, in the case of the number of carbon atoms having no substituent. Examples of the fluorenyl group include a methyl group, an ethyl group, a propyl group, a propyl group, a butyl group, a 323308 25 201211203 an isobutyl group, a trimethyl acetyl group (卩丨¥81〇丫1), and a benzamidine group. (Benzoyl), trifluoroethenyl and pentafluorobenzoinyl. The decyloxy group means an unsubstituted methoxy group and a decyloxy group substituted with a substituent such as a functional atom. The number of carbon atoms of the decyloxy group is usually from 1 to 2 Å, preferably from 2 to 18, more preferably from 2 to 16, in the case of the number of carbon atoms having no substituent. Examples of the decyloxy group include a methyl fluorenyloxy group, an ethoxylated group (Acetoxy), a propyl fluorenyloxy group, a butyl fluorenyloxy group, an isobutyl decyloxy group, a trimethyl ethoxycarbonyl group, and a benzene group. Methyl methoxy, trifluoroethenyloxy and pentafluorobenzoyloxy. The imine residue means an imine compound having a structure of at least one of the formula: H_N=C&lt; and the formula: -N=CH_, and the residue after removing one hydrogen atom in the structure. In terms of this configuration, for example, an aldimine; a ketimine

A compound in which an aldimine bond to a hydrogen atom of a nitrogen atom is substituted with a substituent such as an alkyl group, an aryl group, an arylalkyl group, a arylalkenyl group or an aralkynyl group. The number of carbon atoms of the imine residue is usually 2 to 2 Å, preferably 2 to 18, and more preferably 2 to 16 in the case of the number of carbon atoms having no substituent. In the case of an imine residue, such as the formula .nR'' or the formula: _N=C(R,,) 2 (wherein R' represents a halogen atom, a burn, an aryl group, an aryl group, Aromatic or aryl block, Η&quot; alkaryl, arylalkyl, aralkenyl or aralkynyl. The latter R may be the same or different from each other. It may also be 2 R, forming 2 The base of the valence (for example, a group of carbon atoms such as an ethyl group, a propyl group, a butyl group, a m-hexyl group, and the like, and a group of the remaining atomic groups are formed into a ring to form a ring). 323308 26 201211203 The imine residue may, for example, be a group represented by the following structural formula.

(In the formula, Me represents a methyl group.) _ Turtle: The residue obtained by removing the hydrogen atom bonded to the gas atom of the amine by the amide. The term "amine" as used herein means a gas atom of ammonia 匕 1 or 2 aryl substituted 丨 or 2 guanamine (but a quinone amide having a cyclic structure is also a gm yam). The amidino group means an unsubstituted amine amino group and a substituted amine group substituted with a substituent such as a halogen atom. The number of carbon atoms of the amine-based group is usually 2 to 2 Å, preferably 2 to 18, and more preferably 2 to 16, in the case of the number of carbon atoms having no substituent. Examples of the amine group include amidino group, acetamino group, acrylamide group, butylammonium group, benzamide, trifluoroacetamido group, pentafluorophenyl hydrazine. Amidino, dihydrazide, diethylammonium, dipropylamine, dibutylamine, diphenylguanamine, bis(difluoroacetamidine)amine and bis(pentafluorophenylhydrazine)醯) Amino group. The brewed imine group means a residue obtained by removing a hydrogen atom bonded to the nitrogen atom of the quinone imine 27 323308 201211203 from the enamine. The quinone imine group means a #substituted quinone imine group and a substituted quinone imine group. The number of carbon atoms of the brewed imine group is usually 4 to 20 Å, preferably 4 to 18 Å, more preferably 4 to 16 in the case of the number of carbon atoms having no substituent. The quinone imine group may, for example, be a group shown below.

(In the formula, Me represents a methyl group.) The fluorenyl group means a carboxyl group substituted with a substituent such as a group which is substituted with an alkyl group, an aryl group, an aryl group, and a monovalent aromatic heterocyclic group (hereinafter referred to as a carboxyl group). Replace the slow base). The substituent may have a secondary substituent. The number of carbon atoms in place of the slow group is usually from 1 to 60', preferably from 2 to 48, more preferably from 2 to 45, in the case of the number of carbon atoms which does not contain the secondary substituent. In place of the thiol group, for example, an .f oxy group, an ethane group, a propoxy group, a isopropyl group Ik group, a butyl group, an isobutoxy group, Dibutoxymethyl, second butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, cyclohexyl 323308 28 201211203 Oxygen, thiol, heptyloxy, octyloxyindenyl, 2- Ethylhexyloxy group, decyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, decyloxy group, tri-Imethoxy group, pentafluoro Ethoxyl = king oxime oxy group, allo hexyl oxy group reduction, perfluorooctyloxy sulphate group & stupid base, naphthyloxy and decyloxy. The aromatic group of ^ means an atomic group formed by removing two hydrogen atoms from any of aromatic hydrocarbons and aromatic hydrocarbons. The 2 shellfish silk contains an unsubstituted divalent aromatic group and a substituted 2 valent aromatic group. The divalent aromatic group may, for example, be an extended aryl group or a divalent aromatic heterocyclic group. Stretch = base means an atom formed by the removal of two hydrogen atoms from an aromatic hydrocarbon. The exudate group contains an independent stupid ring or a condensed ring. Stretching aryl means non-replaced green and frontal (four) base. The number of atoms of the wire (4) is usually 6 to 60 Å, preferably 6 to 48, more preferably 6 to 3 Å, and more preferably 6 to 18. The number of carbon atoms does not contain a substituent. 2^Yuanxian County means to have a fangs, (4) heterocyclic formula: the removal of two hydrogen atoms directly bonded to the aromatic ring and (iv) the atomic character m condensed ring. Here, the aromatic heterocyclic ring formation is the same as that described for the monovalent aromatic heterocyclic group. The divalent aromatic heterocyclic group substituted with a divalent aromatic divalent group and a divalent aromatic heterocyclic group substituted with a substituent of the alkyl group. &lt;Molecular compound&gt; The polymer compound of the present invention is improved in the film forming property and the obtained light-emitting element by using the polymer compound as a light-emitting element (IV): the luminous efficiency and the lifetime of the light-emitting element 323308 29 201211203 are improved. The number average molecular weight of the polystyrene benzene is usually 2 x 10 3 or more 'to 2) &lt; 1 〇 3 to 1 χ 1 〇 8 is preferably 丄 到 to lxl G6. In the present specification, a compound having a number average molecular weight of 2x10 or more in terms of polystyrene is referred to as a polymer compound. In addition, the compound having a number average molecular weight of less than 2X1G3 converted by polystyrene is called a low molecular compound. Further, when the number average molecular weight in terms of polystyrene is 2χ1〇3 or more, a dendrimer and an oligomer are also contained in the polymer compound of the present invention. The polymer compound of the present invention contains a repeating unit represented by the formula (?) and a repeating unit represented by the formula (2). First, the repeating unit shown in the formula (1) will be described.

In the formula (1), 'R1, R2, R3, R4 and R5 are each independently and represent a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, Arylalkyl, aralkyloxy, arylalkylthio, fluorenyl, decyloxy, decylamino, quinone imine, imine residue, substituted fluorenyl, substituted fluorenyloxy, substituted hydrazine At least one of a thiol group, a monovalent aromatic heterocyclic group, a heteroaryloxy group, a heteroarylthio group, an aralkenyl group, an arylalkynyl group, a substituted carboxy group or a cyano group 'RR, R, R4 and R5 One system represents a group other than a hydrogen atom. R1, r2, r3, R4 and R5 may be the same or different from each other. Adjacent ones of r1, R2, R3, R4 and R5 may be bonded to each other to form a ring. 323308 30 201211203 At least one of R1, R2, R3, R4 and R5 in the formula (1) represents a group other than a hydrogen atom. At least one of R1, R2, R3, R4 and R5 is preferably a group containing an alkyl group. The group containing an alkyl group means a group of the alkyl group itself and a part containing an alkyl group (for example, an alkoxy group; an alkylthio group; and a group substituted by an alkyl group as a candidate for the above R1 to R5). From the viewpoint of obtaining the life of the light-emitting element using the polymer compound of the present invention, the group containing a group is preferably a base. Further, from the viewpoint of obtaining heat resistance of the light-emitting element using the polymer compound of the present invention, the group containing an alkyl group is preferably an aryl group substituted with a calcinyl group. In the group containing an alkyl group, the number of aliphatic carbon atoms constituting the alkyl group can be achieved because the polymer compound of the present invention can be used for the production of a light-emitting device, and the glutinous solubility of the solvent and the obtained light-emitting element can be reversed. It is preferably 6 or more, and more preferably 12 or more. Further, since the life and heat resistance of the light-emitting element obtained by using the polymer compound of the present invention can be improved, the number of anti-atoms of the aliphatic stone is preferably 100 or less, preferably 60 or less, and more preferably 3 or less. good. Further, the number of aliphatic carbon atoms means the number of carbon atoms contained in the stomach portion of the aliphatic structural portion in the base of the subject. Among them, R1, R2, R3, R4 and in the formula (1)! At least one of ^ is preferably a group having 6 or more carbon atoms, and more preferably an alkyl group having 12 or more carbon atoms. Further, an alkyl group having R3 of 12 or more carbon atoms is more preferable. At least one of ^ and R is preferably a halogen atom. At least one of R2 and R4 is preferably an alkyl group, an aryl group or an alkyl group-substituted aryl group, and R4 is more preferably an alkyl group-substituted aryl group. 323308 31 201211203 In the formula (1), An and Ar*2 are each independently, and may have a group selected from the group consisting of an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, and an arylthioaryl group. Alkyl, aryloxy, arylalkylthio, fluorenyl, ethoxylated, decylamino, quinone imine, imine residue, substituted fluorenyl, substituted fluorenyloxy, substituted fluorenylthio a divalent aromatic group of a substituent in a group consisting of a monovalent aromatic heterocyclic group, a heteroaryloxy group, a heteroarylthio group, an aralkenyl group, an arylalkynyl group, a substituted carboxyl group, and a cyano group . Here, examples of the divalent aromatic group include an extended aryl group or a divalent Φ aromatic heterocyclic group. Examples of the extended aryl group represented by An and An include, for example, a stretching base such as a 14-extension base, a 1,3-phenylene group, and a 1,2-phenylene group; and a 2,7-extension biphenyl group; (81 mouth 1^1^17161^) and 3,6-extended biphenyl such as biphenyl; 1,4-naphthalene-diyl (丫1), 1,5-naphthalene-diyl and 2, Naphthalene-diyl such as 6-naphthalene-diyl; 1,4_ fluorene-diyl, 1,5-fluorenyldiyl, 2,6-fluorenyl-diyl and 9,10-diyl-equivalent-diyl ; 2, 7-phenanthrene (Phenanthrene)-diyl phenanthrene-diyl; l 7_ fused tetraphenyl (Naphthacene)-diyl, 2, 8-fused tetra-di-diyl and 5, 12-fluorene tetraphenyl a base such as a tetraphenylene group; 2, 7-fluorene (Fluorene)-diyl and 3 6-first-based mono-diyl; 1,6-you (Pyrene)-diyl, g-youyi Dibasic, 芘-diyl and 4,9-fluorenyl-diyl isocyanyl; 3,9-fluorene (?61^16116)_diyl and 3, 10-flower-diyl, etc. ; phenylene-diyl; bis-benzoic acid; benzofluorenyl-diyl; and dibenzofluorenyl-diyl, preferably extended or fluorenyl.

The number of carbon atoms of the divalent aromatic heterocyclic group represented by An and An is usually 4 to 60, preferably 323308 32 201211203 4 to 30', in the case of a carbon atom having no substituent. It is 6 to 12. In the case of &amp;, 丄, for example, a 2,5-pyridine bivalent aromatic heterocyclic group, a benzyl group, a bis-diyl group, a fluorenyl group, and a mercapto group; Base; its 2,5 gamma-di-kilo 1,5-...diyl isomer: base; 1A4-^ café-(iv)~diyl 嗤(tetra),diyl-heart benzodi:dioxime-two The base is stupid and ambiguous, 2,5],: ' ' 'yl benzothiazole ~ _ a certain .9 7 - group, 4, 7-benzazole-a; 3, ^ base, etc. (four)-diyl. And 2 / 4 brown _ - diyl; 3, 7 - morphine (four) - two stupid and Shihe heterocyclic pentane H stupid and Shihe heterocyclic pentane dibasic - diyl and other two 啥 - two base. A soil locomotive is preferably a bite-diyl group, a lindenyl group or a furnace, at least one of rL and a pot, and may have an alkyl group selected from the group consisting of an alkyl group, an alkoxy group, and a burnt base. Thiothio group, aryl group, aryl alkoxy group, aryl group thiol group, fluorenyl group, ethoxylated group, decylamino group, quinone imine group, imine ruthenyl group, cleavage group, cleavage group a substituent in the group consisting of a thiol group, a 1 arylheteroyl group, a heteroaryloxy group, a heteroarylthio group, an aryl group, an aryl block group, a fluorenyl group, and a cyano group. An aromatic heterocyclic group of aryl: is preferred. ^ In the case of an extended aryl group represented by An &amp; An, for example, a stupid (for example, the following formulas 1 to 3), a naphthalene diyl group (for example, the following formulas 4 to 13), and a stupid to two (/column) The following formulas 20 to 25), a biphenyl-diyl group (for example, the following formulas 26 to 28), a phenanthrene-diyl group (for example, the following formula 29), a biphenyl group having a condensed ring (for example, the following formulas 31 and 32),茚12 base (eg, formulas 34 and 35), burial-diyl (eg, lower 323308 33 201211203 36 to 38), benzoindole-diyl (eg, the following formula Al to A-3), and dibenzopyrene _ A dibasic group (for example, the following formula A-4).

R R R R R R R i R R?

4 5 fi 7

34 323308 201211203

35 323308 201211203

R R

A-4 (wherein R represents no hydrogen atom or a substituent. The plurality of R may be mutually different or different.) In the above formulas 1 to 29, 31 to 38 and A-1 to A-4, Examples of the substituent represented by R include an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an aralkyloxy group, and an aryl group. # alkylthio, aralkenyl, arylalkynyl, substituted fluorenyl, dentate, fluorenyl, decyloxy, imine residue, decylamino, quinone imine, fluorene aromatic heterocyclic , carboxy, substituted carboxy, cyano, substituted fluorenyloxy, substituted fluorenylthio, heteroaryloxy and heteroarylthio. The hydrogen atom contained in these substituents may be substituted with a gradable oxygen atom. Since the solubility of the polymer compound of the present invention to the gluten-based medium and the element characteristics of the obtained light-emitting device can be improved, at least one of the plurality of R is a group other than a hydrogen atom (that is, the above-mentioned substituent). Fortunately. The substituent represented by R is alkyl, alkoxy, alkylthio, 36 323308 201211203 aryl, aryloxy, arylthio, arylalkyl, aryloxy or monovalent An aromatic heterocyclic group is preferred, and an alkyl group, an alkoxy group or an aryl group is more preferred. The divalent aromatic heterocyclic group represented by An and Αι*2 is exemplified

For example, pyridine-diyl (for example, the following formulas 45 to 5), diazaphenyl (for example, the following formulas 51 to 54), quinolinediyl (for example, the following formulas 55 to 69), and quinoxalinediyl ( Examples are the following formulas 70 to 74), bipyridyldiyl (for example, the following formulas 79 to 81), = xylanyl (for example, the following formulas 82 to 84), and a group having a ten-seat structure (for example, lower: human two 87). a divalent aromatic heterocyclic group containing a nitrogen atom of a hetero atom; a hetero atom such as a 5-member, a nitrogen atom, a sulfur atom, and a lithus atom, a dimer == for example, the following formulas 88 to 92" and Oxygen impurity (for example, a 5-member condensation aromatic of a hetero atom such as the following formula 93 to:

R 4G R

R R

R

R R

48

45 R R

-R R

49 J-R R R )=^\1 R R 51

R 50

52

R S3

&gt;N. N=(' H-i

S4

323308 37 201211203

38 323308 201211203

(wherein R represents a hydrogen atom or a substituent. The plurality of R may be the same or different from each other.) In the above formulae 45 to 74 and 79 to 103, examples of the substituent represented by R are as in the above formula 1R. The examples of the substituents shown are the same. Further, since the solubility of the polymer compound of the present invention in the solvent and the element characteristics of the obtained light-emitting device can be improved, at least one of the plurality of R is a group other than the argon atom (that is, the above substituent) ) is better. Preferably, at least one of the An and Ar2 is a divalent aromatic group represented by the following formula (3) or (4), and more preferably, the An and An lines are each independently, and are the following formula (3) or ( 4) A divalent aromatic group as shown. More preferably, it is a divalent aromatic group represented by the following formula (3) which is not substituted among the divalent aromatic groups represented by the following formula (3) or (4). 39 323308 201211203

(3)

In the formulae (3) and (4), R' represents a halogen atom or an alkyl group.

Preferred examples of the divalent aromatic group represented by the formula (3) include a divalent group represented by the following formulas 3-1 to 3-15.

(In the formula, Me represents a fluorenyl group.) 40 323308 201211203 Preferred examples of the divalent aromatic group represented by the formula (4) include the valence of the following formulas 4-1 to 4-14. Base.

(In the formula, Me represents a methyl group, and t-Bu represents a third butyl group.) The polymer compound of the present invention may contain only one type or may contain two or more types of repeating units represented by the formula (1). Preferred examples of the repeating unit represented by the formula (1) and &amp;' are repeating units represented by the following formulae 1-1 to 1-52. 41 323308 201211203

42 323308 201211203

43 323308 201211203

1-36

44 323308 201211203

1-46 1-47 45 323308 201211203

W

(In the formula, An and An are the same as those described above.) Next, the repeating unit represented by the formula (2) contained in the polymer compound of the present invention will be described. 46 323308 201211203

In the formula (2), 'An represents an aryl group or a monovalent aromatic heterocyclic group. Since the life of the light-emitting element can be improved by using the polymer compound of the present invention, the square base is preferable. In the formula (2), 'Αη represents a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an aralkyloxy group, an arylalkyl group. Thio, fluorenyl, decyloxy, decylamino, quinone imine, imine residue, substituted amine, substituted fluorenyl, substituted fluorenyloxy, substituted fluorenylthio, substituted oxalylamino A monovalent aromatic heterocyclic group, a heteroaryloxy group, a heteroarylthio group, an aralkenyl group, an aralkynyl group, a substituted carboxyl group or a cyano group. Ar4 is preferably a hydrogen atom, an alkyl group, an aryl group or a monovalent aromatic heterocyclic group, and more preferably a hydrogen atom, an alkyl group or an aryl group. In the formula (2), R6 represents an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an aryloxy group, an arylalkylthio group, Sulfhydryl, decyloxy, decylamino, quinone imine, imine residue, substituted amine, substituted fluorenyl, substituted fluorenyloxy, substituted fluorenylthio, substituted fluorenylamino, monovalent Aromatic heterocyclic group, heteroaryloxy group, heteroarylthio group, aralkenyl group, arylalkynyl group, substituted carboxy group or cyano group. When there are a plurality of R6, these may be the same or different. In the formula (2), 'a' represents 0 or 1. The two a's present may be the same or different. 323308 47 201211203 Among the repeating units represented by the formula (2), a repeating unit represented by the following formula (20) is preferable.

(In the formula (20), the definitions of An and Ar4 are the same as those of An and Ar4 of the formula (2).) In the formula (20), An is an argon atom, an alkyl group, an aryl group or a monovalent aromatic φ. A heterocyclic group is preferred, and a hydrogen atom, an alkyl group or an aryl group is more preferred. In the formula (20), when Ar3 or An is an aryl group, since the solubility of the polymer compound of the present invention in a solvent can be improved, the aryl group is preferably a substituent having 2 or more carbon atoms. In the case of the repeating unit represented by the formula (20), the repeating unit represented by the following formulas le to 8e can be exemplified. 48 323308 201211203

(wherein, n-Bu represents n-butyl group, and b) represents a third butyl group. In the polymer compound of the present invention, only one type or more than two or more repeating units represented by the formula (2) may be contained. . The ratio of the repeating unit represented by the formula (1) to all the repeating units constituting the polymer compound of the present invention is preferably larger from the viewpoint of electron transportability (that is, the electron transport property is improved). The viewpoint of the life of the light-emitting element obtained when the polymer compound is used for producing a light-emitting element is preferably 323308 49 201211203. Therefore, the above ratio is preferably 10 mol% or more and 30 mol/min or less, more preferably 10 mol% or more and 20 mol% or less, and more preferably 10 mol% or more and 15 mol% or less. On the other hand, the ratio of the repeating unit represented by the formula (2) to all the repeating units constituting the polymer compound of the present invention can be improved by thermal stability and when the polymer compound is used for producing a light-emitting element. The life of the light-emitting element is preferably 20 mol% or more. The upper limit of the ratio is not particularly limited, but is usually 75 mol% or less. The total ratio of the repeating unit represented by the formula (1) and the repeating unit represented by the formula (2) to all the repeating units constituting the polymer compound of the present invention can be improved by using the polymer compound of the present invention. The electron-transporting property and the lifetime of the light-emitting element are preferably 30 mol% or more, more preferably 40 mol%/〇 or more, and more preferably 50 mol% or more. The polymer compound of the present invention may further comprise a repeating unit represented by the following formula (5). -ΑΓ5-(5) ^ In the formula (5), An represents an aryl group or a divalent aromatic heterocyclic group. An example of an aryl group of An is the same as the above-mentioned aryl group in Αιί and Ar2. Examples of the aromatic heterocyclic group of the valence of Ars are the same as those of the above-mentioned divalent aromatic heterocyclic group in An and An. The repeating unit represented by the formula (5) is a repeating unit represented by the following formula (6). 50 323308 201211203

In the formula (6), Ar6 and An are each independently, and represent an alkyl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, an arylalkyl group, an aralkyloxy group, or an aryl group. Thio group, fluorenyl group, decyloxy group, decylamino group, quinone imine group, imine residue, substituted amine group, substituted aryl group, substituted&gt;5 oximeoxy group, substituted sulfhydryl group, substituted stone Anthracenylamino, heteroaryloxy, heteroarylthio, aryl, aralkynyl, substituted carboxy or cyano. R7 represents alkyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, arylalkyl, aryloxy, arylalkylthio, fluorenyl, methoxy , amidino, adiamine, imine residue, substituted amine, substituted fluorenyl, substituted fluorenyloxy, substituted fluorenylthio, substituted fluorenylamino, monovalent aromatic heterocyclic, Heteroaryloxy, heteroarylthio, aralkenyl, aralkynyl, substituted carboxy or cyano. Since it is possible to increase the solubility of the polymer compound of the present invention to a solvent and the life of the obtained light-emitting device, it is preferred that at least one of Are and An is a hydrogen atom or an alkyl group. In the formula (6), a represents 0 or 1. The presence of 2 &amp; can be the same or different. When there are a plurality of R7, these may be the same or different. The repeating unit represented by the following formula (7) and the repeating unit represented by the following formula (8) can be exemplified by the repeating unit represented by the formula (5). 323308 51 201211203

Ra

(7) Formula (In the formula, R8 and R9 are each independently, and represent an alkyl group, an alkoxy group, a thiol group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an aralkyloxy group, and an aromatic group. Alkylthio, fluorenyl, decyloxy, decylamino, quinone imine, imine residue, substituted amine, substituted fluorenyl, substituted fluorenyloxy, substituted fluorenylthio, substituted fluorenyl An amine group, a monovalent aromatic heterocyclic group, a heteroaryloxy φ group, a heteroarylthio group, an aralkenyl group, an arylalkynyl group, a substituted carboxy group or a cyano group. R8 and R9 may be the same or different from each other. From the viewpoints of the balance between the heat of the polymer compound of the present invention and the solubility to the organic solvent, the formula (in the middle, R8 and R9) is independently an alkyl group, an aryl group, or a monovalent aromatic heterocyclic ring. a group, an alkoxy group, an aryloxy group, an arylalkyl group or a substituted amine group is preferred, and an alkyl group or an arylalkyl group is more preferred, and an alkyl group is more preferred, and a propyl group, an isopropyl group, Butyl, t-butyl, isobutyl, pentyl, isopentyl, hexyl, cyclohexyl, heptyl, octyl, 2-ethylhexyl, cyclohexyldecyl, decyl, decyl, 3, 7 _二曱基辛Or dodecyl group is particularly preferred .R and R9 may be the same or different from each other, the same are preferred.

In the formula (8), 'Rl° and R11 are each independently, and represent an alkyl group, an alkoxy group, a T-based thio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an aralkyloxy group, Arylalkylthio, fluorenyl, decyloxy, decylamino, quinone imine, 52 323308 201211203 imine residue, substituted amine, substituted fluorenyl, substituted fluorenyloxy, substituted fluorenylthio And a substituted mercaptoamine group, a monovalent aromatic heterocyclic group, a heteroaryloxy group, a heteroarylthio group, an aralkenyl group, an aralkynyl group, a substituted carboxyl group or a cyano group. ΙΓ and R11 may be the same or different from each other. In the formula (8), at least one of R1() and R11 is an alkyl group, an aryl group, or a monovalent point of view from the viewpoint of the balance between the heat resistance of the polymer compound of the present invention and the solubility in an organic solvent. An aromatic heterocyclic group, an arylalkyl group or an amine group is preferred, and an alkyl group, an aryl group, a monovalent aromatic heterocyclic group or an amine group is more preferably an alkyl group, an aryl group or a monovalent group. The aromatic heterocyclic group is more preferably a complex of an alkyl group or an aryl group. R1() and R11 may be the same or different from each other. In the formula (8), b represents 0 or 1. In the case of the repeating unit represented by the formula (7), repeating units represented by the following formulas 7-001 to 7-019 and 7-101 to 7-105 can be exemplified.

53 323308 201211203

54 323308 201211203

(wherein Me represents a fluorenyl group.) The repeating unit represented by the formula (8) can be exemplified by the following formulas 8-001 to 8-017, 8-101 to 8-113, 8-201 to 8- Repeat unit shown in 208.

Me

Me

t,Bu 8^003

Me

Me Me

Me 8-005

Me

8^008 55 323308 201211203

Me

Me

t-Bu

t-Bu

56 323308 201211203

Mo m

Me

Me

t-Bu

8-205 B-204 57 323308 201211203

(wherein Me represents a thiol group, Et represents an ethyl group, i-Pr represents an isopropyl group, n-Bu represents a n-butyl group, and t-Bu represents a tert-butyl group.) In the polymer compound of the present invention, Only one type of repeating unit represented by the formula (5) may be contained. In the polymer compound of the present invention, the repeating unit represented by the formula (5) may be selected from the group consisting of a repeating unit represented by the formula (6), a repeating unit represented by the formula (7), and a formula (8). a repeating unit of the repeating unit shown, or a combination of two or more repeating units. Further, in the case of the repeating unit represented by the formula (5), the polymer compound of the present invention may comprise: a repeating unit represented by the formula (6), a repeating unit represented by the formula (7), and a formula (8). ) The combination of the repeating units shown is more than two. The ratio of the repeating unit represented by the formula (5) is usually 0 mol% or more and 80 mol% or less, based on all the repeating units constituting the polymer compound of the present invention, and is 5 mol% or more and 70 mol% or less. For better, it is better to use 10 mol% 58 323308 201211203 = 60 mol. "It is better to use Μ 耳 以 彳 彳 彳 彳 彳 彳 彳 彳 ” ” 重 重 重 重 重 重 重 重 重 重 重 重 重 重 重 重 重 重 重 重 重 重 重 重 重 重The repetitive single ratio of the 祯 祯 分 々 々 Λ Λ Λ 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 々 々 々 々 々 々 々 々 々 々 々 々 々 々 々 々 々 々 々 々 々 々 々 々 々 々 々 々 々 々 More preferably, the compound == polymer compound, containing € as shown in the following formula (8)

In the formula (9), 'An, Ar9, ArlQ and Arl4 are each independently and represent an extended aryl group or a divalent aromatic heterocyclic group. In the formula (9), 'Aru, Ari2 &amp; Ari3 are each independently and represent an aryl group or an ivalent aromatic heterocyclic group. Equation (9) t, An, An, An. , Ar&quot;, Ari2, Ari3, and Ari4 are each independently capable of having a substituent. In the formula (9), the X&amp;y systems are independent of each other and represent 〇 or 丨. But the value of x + y is 0 or 1 〇 in equation (9), when An, Ar9, An. When Aril, An2, An3 or Ari4 has a substituent, examples of the substituent include an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an arylalkyl group, an aralkyloxy group, and an aromatic group. Alkenyl, arylalkynyl, amine, substituted amine, halogen atom, fluorenyl, decyloxy, valence 323308 59 201211203 aromatic heterocyclic group, carboxyl group, nitro group and cyano group, preferably alkyl group, Alkoxy, aryl, aryloxy, arylalkyl, aralkoxy, substituted amine, fluorenyl or cyano, more preferably alkyl, alkoxy or aryl. In the formula (9), 'An, An, An. And the aryl group represented by Αγη, for example, 1,3-phenylene, 1,4-phenylene, 1,4-naphthalenediyl, 2,6-naphthalenediyl, 9, 10 - fluorenyl, 2,7-phenanthryl, 5,12-fused tetraphenyldiyl and 2,7-second. The number of carbon atoms of the divalent aromatic hetero group represented by 'An, Ar" in the formula (9) and Aru is usually 4 to 60' in the case of the number of carbon atoms having no substituent. It is preferably 4 to 20, more preferably 4 to 9. The above-mentioned divalent aromatic heterocyclic group may, for example, be 2,5-thiophenediyl, methyl 2, 5-pyrrolediyl, 2 , 5-furanyldiyl, benzo[2,anthracene-3]thiadiazole-4,7-diyl, 3,7-phenanthryldiyl and 3,6-carbazolediyl. In formula (9) In the case of Ars, Arg, An, and Ar, for example, a divalent group represented by the following formulas lb to 3b can be given.

In the formula (9), the base, 1, 4~ stupid base, refers to φ / soil

An and An〇 are preferably an aryl group, more preferably an anthracene, a benzophenone, a 1,4-naphthalenediyl group, a 2,6-naphthalenediyl group or the above formula ib. , 4_ stretched phenyl or 14-naphthalene diyl, with 丨, 4-extension base is particularly good. In the formula (9), An is preferably 1&gt;3-phenylene, 1&gt;4_extension base, 1&gt;4_323308 60 201211203 naphthalenediyl, 2,7-3⁄4 diyl, benzo[2, 1, 3] ° Di-salt-4, 7-diyl, 3 7-morphinediyl or a group represented by the above formula lb, preferably 1,4-extended base, 4- 4-n-based, 2, 7 - 苐 · a group or a group represented by the above formula lb, more preferably a 14-phenylene group or a group represented by the above formula lb. In the formula (9), Aru, An2 and Are are each independently, preferably an alkyl group, an aryl group or a monovalent aromatic heterocyclic group, more preferably an alkyl group or an aryl group, and more preferably an aryl group. Preferred examples of the 袓% by weight represented by the formula (9) include repeating units represented by the following formulas lc to 4c. Further, the formula lc to the above, RZ1 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an oxy group, an aryl group, an aryl group, an amine group, a substituted amine group Hi i Oxygen divalent aromatic heterocyclic group, yl 1 group or nitrogen group. When there are hard numbers in the field, they can be the same or different.

323308 61 201211203

3c

Among the repeating units represented by the formula (9), a repeating unit represented by the following formula (10) is preferred.

An alkyl group of 20, an alkoxy group having 1 to 20 carbon atoms, a phenylalkyl group having 7 to 26 carbon atoms, a phenylalkoxy group having 7 to 26 carbon atoms, a phenyl group, a phenoxy group, and a carbon group An alkylphenyl group having 7 to 26 atoms, an alkoxyphenyl group having 7 to 26 carbon atoms, an alkylcarbonyl group having 2 to 21 carbon atoms, an anthracenyl group, and an alkoxycarbonyl group having 2 to 21 carbon atoms Or carboxyl group. Alternatively, it may be replaced by a ring formed by R31 62 323308 201211203 and R41 instead of the above. When a plurality of R31 are present, the ones may be the same or different, and when there are a plurality of R41, the ones may be the same or different, and when there are a plurality of R51, the ones may be the same or different. In the formula (10), s and t are each independently, and represent an integer of 0 to 4. u is 1 or 2. v is an integer from 0 to 5. In the formula (10), when R31 and R41 together form a ring, the ring may, for example, be a heterocyclic ring having a substituent (5 to C14). Examples of the heterocyclic ring include, for example, a morphine ring, a thiopheneline ring, an eleven φ ring, a piperidine ring, and a piperene ring. Examples of the repeating unit represented by the formula (10) include the following formulas Id to 10d. Repeat unit shown.

The ratio of the repeating unit represented by the formula (5) is usually 0 mol% or more and 20 mol%/〇63 323308 201211203 or less with respect to all the repeating units constituting the polymer compound of the present invention. Moore% or less is preferred. The total ratio of the repeating unit represented by the formula (1), the repeating unit represented by the formula (5), and the repeating unit represented by the formula (9) is 90% with respect to all the above repeating units. More preferably, the ear is more than 95% by mole, more preferably 95% by mole or more, more preferably 99% by mole or more, and particularly preferably 1% by mole (to remove unavoidable impurities). Hereinafter, a preferred method for producing the polymer compound of the present invention will be described. The polymer compound of the present invention can be produced, for example, by condensation polymerization. In the method of the above condensation polymerization, for example, a method of performing polymerization by a Suzuki reaction (Chemical Review (Chem. Rev.), Vol. 95, p. 2457 (1995)), by Grignard (Grignard) Reaction Method for Polymerization (Kyoritsu Publishing, Volume 2 of Polymer Functional Materials, Synthesis and Reaction of Polymers (2), pages 432 to 433), and polymerization by Yamamoto Coupling (Progressive) Polymer Science (Prog. Polym. Sci.), Vol. 17, pp. 1153 to 1205, 1992), a method of polymerization by a zero-valent nickel complex, a method of polymerization by an oxidizing agent such as FeCU, and an electrochemical method. The method of oxidative polymerization and the method of decomposing the intermediate polymer having an appropriate desorption group are carried out exclusively. From the viewpoint of structural control, it is preferred to carry out polymerization by Suzuki Coupling. The method, the method for polymerizing by a Grenadi reaction, and the method for polymerizing by a nickel-nickel complex. The polymer compound can be produced, for example, by condensation polymerization of a compound represented by the formula: Y3 to WLY4 with a compound represented by the formula: Y5-W2-Y6. 323308 64 201211203 In the formula, W1 and W2 are independent of each other, and represent a repeating unit represented by the above formula (1), the above formula (2), the above formula (5), or the above formula (9). Y3, Y4, Y5 and Y6 are each independently and represent a polymerization reactive group. When the polymer compound of the present invention has a repeating unit other than the above, a compound which has two polymerization reactive groups having a repeating unit other than the above may be allowed to coexist and undergo condensation polymerization. Examples of the above-mentioned polymerization reactive group include a halogen atom, an alkylsulfonate group, an arylsulfonate group, an arylalkylsulfonate group, a boronic acid ester residue group, a fluorenylmethyl group, and the like. A fluorenyl group, a phosphonate sulfhydryl group, a monohalogenated fluorenyl group, a boronic acid residue (-B(0H)2), a decyl group, a cyano group, a vinyl group, and the like. The functional atom of the above-mentioned polymerization reactive group may, for example, be a fluorine atom, a gas atom, a desert atom or a broken atom. The alkylsulfonic acid group as the above-mentioned polymerization reactive group may, for example, be an anthracenesulfonic acid group, an ethylsulfonic acid group or a trifluorosulfoniumsulfonic acid group. The arylsulfonic acid group as the above-mentioned polymerization reactive group may, for example, be a benzenesulfonic acid group or a p-toluenesulfonic acid group. The arylsulfanyl group as the above-mentioned polymerization reactive group may, for example, be a benzylsulfonic acid group. The boronic acid ester residue which is the above-mentioned polymerization reactive group may, for example, be a group represented by the following formula.

(In the formula, Me represents a methyl group, and Et represents an ethyl group.) 65 323308 201211203 The thiol group which is the above-mentioned polymerization reactive group may, for example, be a group represented by the following formula. ~CH2S+Me2X°_, -CH2S+Ph2X. In the formula, X represents a halogen atom, and Ph represents a stupid group. The sulfhydryl group which is the above-mentioned reactive group may, for example, be a group represented by the following formula. ~CH2P+Ph3X. - (wherein, X is a halogen atom.) The fluorenyl group which is the above-mentioned polymerization reactive group is a group represented by the following formula. -CH2P〇(〇r,,) 2 (wherein R'' represents an alkyl group or an aryl group.) Examples of the above-mentioned polymerizable reactive group include a fluoromethyl group, a gas group, and a bromine group. Sulfhydryl, iodine methyl. When the valence φ nickel complex is used, for example, in the case of a Yamamoto coupling reaction, it is a tooth atom, an alkylsulfonate group, an arylsulfonate group, an arylalkylsulfonate group, etc., and a Suzuki coupling reaction or the like. When a nickel catalyst or a palladium catalyst is used, it is an alkylsulfonic acid group, a halogen atom, a boronic acid ester residue, a boronic acid residue, or the like. In the method for producing a polymer compound of the present invention, since the synthesis of the polymer compound is easy, the polymerization reactive group may be selected from the group consisting of a tooth atom, an alkyl group, an aryl sulfonate group, and an arylalkyl sulfonate. One or more groups of the group consisting of an acid group, a boronic acid residue, and a boronic acid ester residue, and a preferred production method is a halogen atom having a full raw material compound, a phenolic acid group, and an aryl group. The ratio of the total number of moles of the acid group and the base group of the acid group (J) to the total number of moles of the boric acid residue 66 323308 201211203 base and the borate residue (K) is actually κ usually K/ J is from 0.7 to 1.2., and a condensation polymerization is carried out using a nickel catalyst or a palladium catalyst. The combination of the compound as the above-mentioned starting material (that is, the compound represented by the formula: Ylwi-Y4 and the compound represented by the formula: Y5-W2-Y6) may, for example, be a dihalogenated compound or a bis(alkyl) acid. A combination of a compound, a bis(aryl-based acid vinegar) compound or a bis(aryl-based acid vinegar) compound with a diacyl acid compound or a succinic acid vinegar compound. In the production of a polymer compound for controlling the sequence, a halogen-boric acid compound, a boronic acid ester compound, an alkylsulfonate-boronic acid compound, an alkylsulfonate-borate compound is used in the above compound. , aryl sulfonate-boric acid compound, aryl sulfonate-borate compound, arylalkyl sulfonate-boric acid compound, arylalkyl sulfonate-boric acid compound, aryl sulfonic acid s It is advisable to use a succinic acid compound or the like. Here, among the compounds represented by the formula: y^w^y4, the compound having the repeating unit represented by the above formula (1) is represented by the following formula (i)

The compound is preferred. x\ /X

(In the formula, Ra, Rf &amp; Rg each independently represent a hydrogen atom or an alkyl group, and Rb, Re, Rd and Re each independently represent an alkyl group or an alkyl-substituted aryl group. 67 323308 201211203

Ar1 and Ar2 are each independently, and may have an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an aralkyloxy group, or a group. Alkylthio, alkanoyl, alkoxy, amidino, quinone, imine residue, substituted fluorenyl, substituted fluorenyloxy, substituted fluorenylthio, monovalent aromatic heterocyclic a divalent aromatic group of a substituent in the group consisting of a heteroaryloxy group, a heteroarylthio group, an aryl group, a ^'alkynyl group, a substituted sulfhydryl group, and a cyano group. X represents a tooth atom, a boronic acid ester residue, a boronic acid residue, a group represented by the following formula (a-Ι), a group represented by the following formula (a_2), a group represented by the following formula (a-3), Or a group represented by the following formula (a-4). The two defects present may be the same or different. )

(1)—MgXA (a-2) — 2hXA (a-3) —Sn(RT)3 (a-4) (wherein 1^ represents an alkyl group or an aryl group, and may have a substituent. 乂4 Further, in the formula (a-4), the three RTs present may be the same or different.) The organic solvent used in the above condensation polymerization is subjected to sufficient deoxidation treatment and dehydration in order to suppress side reactions. Processing is preferred. However, when the eucalyptus coupling reaction or the like is carried out in a reaction with the two-phase system of water, this is not the case. The organic solvent used in the above condensation polymerization may, for example, be: 68 323308 201211203 a saturated hydrocarbon such as pentane, hexane, heptane, octane or cyclohexane; benzene, toluene, ethylbenzene, xylene, etc. Unsaturated hydrocarbons; carbon tetrachloride, gas, methylene chloride, gas, butyl, diced, chloropentan, sulphate, sulphur, hexane, cyclohexane, bromocyclohexane, etc. Ιδ saturated hydrocarbons; halogenated unsaturated hydrocarbons such as chlorobenzene, dichlorobenzene, trichlorobenzene; alcohols such as decyl alcohol, ethanol, propanol, isopropanol, butanol, and tert-butyl alcohol; formic acid, acetic acid, and C a carboxylic acid such as an acid; a dimercaptoether, a diethyl sulphate, a decyl-tert-butyl bond, an arsenic of tetrazolium, a tetrazole, a dicyclopentane, or the like; a tridecylamine, a triethylamine Amine, hydrazine, hydrazine, hydrazine, Ν'-tetramethylexene, amines such as ethyldiamine, pyridine, etc.; hydrazine, hydrazine-dimercaptoamine, hydrazine, hydrazine-dimercaptoacetamide, hydrazine , hydrazine-diethylacetamide, hydrazine-fluorenyl hydrazine-oxidized morpholine and the like hydrazines, etc., preferably ethers, tetrahydrofuran, diethyl ether is particularly preferred. These organic solvents may be used alone or in combination of two or more. In the above condensation polymerization, a base and/or a catalyst may be added in order to promote the reaction. It is preferred that the above base and catalyst are sufficiently dissolved in the solvent used for the reaction. The alkali and/or the catalyst is mixed, and the reaction solution is slowly added with a solution of a base or a catalyst while stirring in an inert gas such as argon or nitrogen; or vice versa, the reaction liquid is slowly added to the alkali and/or It can be used in the solution of the catalyst. When the polymer compound of the present invention is used to produce a light-emitting device or the like, since the purity of the compound affects the performance of the light-emitting element such as the light-emitting property, it is preferred to refine and sublimate the compound as a raw material before polymerization. The method such as crystallization is purified and then polymerized. Further, after the polymerization, purification treatment by reprecipitation purification, separation by column chromatography, or the like is preferably carried out. &lt;Composition&gt; 69 323308 201211203 The composition of the present invention contains at least one of the polymer compound of the present invention and a group selected from the group consisting of a hole transporting material, an electron transporting material, and a luminescent material. The luminescent material may, for example, be a low molecular fluorescent luminescent material, a luminescent organic metal complex compound or a high molecular fluorescent luminescent material. In general, when the luminescent organometallic complex compound is used as a dopant in the composition of the above polymer compound for the luminescent material of the light-emitting element, the lowest triplet excitation energy is high in the host material. Better. Therefore, in the composition of the present invention, when a light-emitting organometallic compound compound which exhibits a red light emission with a light-emitting wavelength of 600 nm or more as a light-emitting material is used, the polymer compound of the present invention contained in the composition has the above formula. In the case of the heavy-duplex unit shown in (5), it is preferred to repeat the repeating unit represented by the above formula (6). On the other hand, in the composition of the present invention, when the luminescent material is used, when the luminescent organic metal complex compound exhibiting green luminescence having a luminescence peak wavelength of 500 η or more and less than 600 nm is used, the present invention is included in the composition. The polymer compound is a repeating unit represented by the above formula (5), and further comprises a repeating unit selected from the above formula (7) and a repeating unit represented by the above formula (8). Repeating units are preferred. The wavelength of the luminescence peak of the luminescent metal-conjugate compound is, for example, dissolved in an organic solvent such as dioxins, hydrazine, and chloroform to prepare a thin solution, and the PL of the thin solution is measured ((Ph〇t〇iuminescenee; The luminescent organic metal-conjugated compound is exemplified by a known compound such as a triplet luminescent complex or an organic EL device which has been conventionally used as a low molecular system. Compounds of luminescent materials, and Nature, (1998), 395, 151, Appl. Phys. Lett. (1999), 75(1), 4.

Proc. SPIE-Int. Soc. Opt. Eng. (2001), 4105 (0rganic Light-Emitting Materials and Devices IV), 119 'J. Am. Chem. Soc., (2001), 123, 4304, Appl. Phys· Lett., (1997), 71(18), 2596, Syn. Met., (1998), 94(1), 103, Syn. Met., (1999), 99(2), 136, Adv. Mater· , (1999), • 11(10), 852, Inorg. Chem., (2003), 42, 8609, Inorg.

Chem., (2004), 43, 6513, Journal of the SID 11/1, 161 (2003), W02002/066552, W02004/020504, and W02004/020448, and the like. Since the light-emitting element having high luminous efficiency can be obtained, the sum of the squares of the coefficient of the outermost d-orbit of the center metal of the highest occupied molecular orbital (HOMO) of the metal-missing body is the same as the above-mentioned luminescent organometallic compound compound. It is preferable that the ratio of the sum of squares of the total atomic orbital coefficients is 1/3 or more. In the case of this compound, the central metal may be an orthometalated conjugate belonging to the transition metal of the sixth cycle of the periodic table. The central metal of the luminescent organometallic conjugate compound may, for example, have an atomic order of 50 or more, and may exhibit spin-orbit interaction for the conjugate, and singlet and second for the conjugate. Metals in the intersystem crossing can occur between the heavy states. The central metal is preferably gold, platinum, rhodium, ruthenium, rhodium, tungsten, ruthenium, osmium, ruthenium, rhodium, iridium, osmium or iridium; more preferably gold, platinum, rhodium, iron, iridium or 71 323308 201211203 Tungsten; the better is gold, platinum, rhodium, hungry or chain; gold, platinum, rhodium or ruthenium is the best 'preferably platinum or rhodium. The ligand of the above-mentioned luminescent organometallic compound compound may, for example, be 8-hydroxyquinoline or a derivative thereof, benzoquinolinol and a derivative thereof, and 2-base-n ratio bite and its derivative. Things. The ligand of the aforementioned luminescent organometallic complex compound, because

To increase the solubility in a solvent, so that it has a group consisting of an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an aryl group which may have a substituent, and a heteroaryl group which may have a substituent The substituent (hereinafter referred to as "ligand-substituted soil") is more preferable. The total number of atoms other than the hydrogen atom contained in the ligand substituent is preferably 3 or more, more preferably 5 or more, and more preferably 7 or more. In addition, the ligands present in each ligand are quaternary, and the species may be the same or different in each ligand. The appearance of luminescence at 600 nm preferably has the following composition. The organometallic complex structure having the structure represented by the formula (11) is a luminescent organic metal complex compound having an emission peak wavelength of 500 nm or more.

« LJ η (11) (wherein, Rlp, R2p, r3p, R4p, r5p represent a hydrogen atom or an aryl group. R6p," and r8p are each independently 323308 72 201211203 The part shown by the following formula represents a single anion A monoanion-type bidentate ligand.

Rx&amp;Ry is assigned to the atom of the central metal lr, which is independent of each other and represents a carbon atom, an oxygen atom or a nitrogen atom. m represents an integer of 1炱3, and η represents an integer of 〇 to 2. In the above-mentioned monoanionic bidentate ligand, in the formula (11), the circular arc portion in which Rx and Ry are bonded is a monoanion of a divalent group having 3 to 30 atoms other than a hydrogen atom. A preferred bidentate configuration is preferred, and for example, a ligand having a structure represented by the following formula may be mentioned.

(wherein '* indicates the position of the coordinating atom.) In the formula (11), the ligand shown on the left side and the ligand system shown on the right side are independent of each other, and may have the above-mentioned ligand substituent because the solvent can be promoted. The solubility is such that it is preferred to have the above ligand substituent. Among them, the luminescent organic metal-conjugate compound having a luminescent wavelength of 5 〇〇 nm or more and less than 6 Å is preferably 323308 73 201211203, and the following compounds are preferred.

74 323308 201211203

75 323308 201211203

(wherein tBu represents a third butyl group, and R represents hydrogen or a substituent. The plurality of R groups present may be the same or different.) A luminescent organic compound having a luminescent color having a luminescence peak wavelength of 600 nm or more and exhibiting a red color The metal complex compound is preferably a compound having a structure represented by the following formula (12), (12-1) or (12-2).

76 323308 201211203

And r25p are independent of each other, and represent a hydrogen atom, an atom, an alkyl group, an alkoxy group, a thiol group, an aryl group, an aryloxy group, an arylthio group, an aryl group, an aryloxy group, an aryl group. Pyridylthio, sulfhydryl, acidoxy, decylamino, quinone imine, imine residue, substituted amine, substituted fluorenyl, substituted fluorenyloxy, substituted 矽φ thio, substituted fluorenyl An amine group, a monovalent aromatic heterocyclic group, a heteroaryloxy group, a heteroarylthio group, an aralkenyl group, an aralkynyl group, a substituted carboxyl group or a cyano group. These base systems may have a substituent. m represents an integer from 0 to 3. The portion shown by the following formula means the same as the one represented by the above formula (11).

In the formulae (12) and (12-1), Z1, Z2, Z3, Z4 and Z5 are each independently, and represent -C(R#)= or a nitrogen atom. R# represents a hydrogen atom or a substituent. 77 323308 201211203 In the formulas (12), (12-1) and (12-2) 'when r9p, riip, r12p, R13p, R14p, p, r16p, Rl7p, Rl8p, Rl9p, R2Dp, R2ip, p, heart When there are a plurality of R24p, R25p, Z1, Z2, Z3, Z4 and Z5 systems respectively, they may be the same or different. However, at least two of 2, 22, 23, 24 and 25 are nitrogen atoms. Among them, the luminescent organic metal complex compound having a luminescent color having an emission peak wavelength of 600 nm or more is preferably the following compound.

78 323308 201211203

79 323308 201211203

80 323308 201211203

81 323308 201211203

82 323308 201211203

Cf3

83 323308 201211203

84 323308 201211203 Ο

(wherein, tBu represents a butyl group, and Me represents a fluorenyl group.) The luminescent organometallic compound compound may be used singly or in combination of two or more. The low molecular weight fluorescent material is usually a material having a maximum peak of fluorescence emission in a wavelength range of 400 nm or more and 700 nm or less. The molecular weight is usually less than 3,000, preferably from 1 to 2, more preferably from 10 to 1 Torr. The above-mentioned low molecular fluorescent material may be used as a light-emitting material of an organic EL element. Examples of the aforementioned low molecular weight fluorescing stock include naphthophthalene, anthraquinone and derivatives thereof, and derivatives thereof, and hydrazine.丫 323308 85 201211203 (Quinacridone) derivative, xanthene (xanthene) pigment, Coumarin pigment, Cyanine pigment, triphenylamine derivative, hydrazine derivative Compound, bismuthin derivative, bis(styryl)benzene derivative, biphenyl etyrene derivative, η-pyrrole derivative, 11-cetin ring compound, pyridine ring compound and oligothiophene derivative Ordinary pigmentary materials; hydroxyquinoline aluminum complex, benzohydroxyquinolinium complex, benzoxazolyl zinc complex, benzothiazole zinc complex, azomethyl-synaptosome, 卟琳锌The ligand and the erbium complex have a central metal having Al, Zn, Be _ or a rare earth metal (for example, ♦ Tb, Eu, Dy, etc.), and the ligand has oxadiazole, thiadiazole, phenylpyridine, A metal-missing system material such as a phenyl benzimidazole or a quinoline structure. The polymer fluorescent material may, for example, be a poly(p-stylene-based ethylene derivative, a polythiophene derivative, a poly-p-phenylene derivative, a polyoxan derivative, a polyacetylene derivative, or a polyfluorene. a derivative, a polyethylene sigma singer, and a chromophoric material comprising a pigment-based material exemplified by the above-described low molecular fluorescent material. In the composition of the present invention, the ratio of "at least one selected from the group consisting of a hole transporting material, an electron transporting material, and a luminescent material" to the polymer compound is 100 parts by weight based on 100 parts by weight of the polymer compound. Each material of "at least one material selected from the group consisting of a hole transporting material, an electron transporting material, and a light-emitting material" is usually set to be 〇.〇1 love parts to 400 parts by weight. Parts by weight to 15 parts by weight. The above-mentioned hole transporting material may be a known material of a material for the hole of the organic EL element 86 3233 〇» 201211203. Examples of the above-mentioned hole transporting material include, for example, poly(ethyl bromide) derivatives; (iv) calcination and its derivatives; polyoxyalkylene derivatives having an aromatic amine at the side = or a primary bond; and pyrazoline derived _, arylamine derivatives; anthracene derivatives; polyaniline (Polyaniline) and its ηΤ biological 'polyseptene and its derivatives; polyarylamines and their derivatives; polypyrrole and its street organisms; Pair of 'stupid ethylene' and its derivatives; poly(2, 5-thiophene) and its derivatives. The above-mentioned hole transporting material may have a aryl group and a hexavalent heterocyclic group having 2% as a copolymerization component (constituting unit). The electron transporting material may be a known material of electron transport = 2 of the organic EL element. In the case of the aforementioned electron-transporting materials, there may be mentioned a traitorous creature, Anthraqui nodi me thane, aragonine bios, benzene and its derivatives, naphthoquinone and its derivatives, hydrazine and Diorganisms, tetracyanoquinonedioxane and its derivatives, anthrone derivatives, thiophene ethene and its derivatives, diphenoquinone Z organism, 8_ quinazoline The metal complex of its derivatives, triaryl, its biological, (d), its derivatives, its derivatives, its derivatives, and its derivatives. The above electron transporting material may have an aromatic aryl group or an aromatic heterocyclic group of 2 ja as a copolymerization component (constituting unit). Further, in the composition of the present invention, each component may be used alone or in combination of two or more. &lt;Liquid Composition&gt; The liquid composition of the present invention is composed of the polymer compound of the present invention, a solvent or a dispersion medium. In the solvent or dispersion medium used in the liquid composition of the present invention, 87 323308 201211203 can be uniformly dissolved or dispersed in a conventional solvent to be a component of the film. In the case of such a solvent, the following may be mentioned. Aromatic hydrocarbon solvent: toluene, xylene (each isomer or a mixture thereof), 1,2,3-trimethylbenzene, 1,2,4-trimethylbenzene, stilbene (1) , 3, 5-trimethylbenzene), ethylbenzene, propylbenzene, cumene, butylbenzene, isobutylbenzene, 2-phenylbutane, tert-butylbenzene, pentylbenzene, Neopentylbenzene, isoamylbenzene, hexylbenzene, cyclohexylbenzene, heptylbenzene, octylbenzene, 3-propylindole, 4-propylindole, 1-mercapto-4-propylbenzene, 1 , 4-diethylbenzene, 1,4-# dipropyl benzene, 1,4-di-tert-butylbenzene, decane (Indane) and tetraphosphorus (1,2,3,4-tetrahydronaphthalene )Wait. The aliphatic hydrocarbon-based solvent: n-pentane, n-hexane, cyclohexane, methylcyclohexanthene, n-glycan, n-octyl, n- squid, n-xanthene, and decal indane. Aromatic scaly solvent: Anisole, ethoxybenzene, propoxybenzene, butoxybenzene, pentyloxybenzene, cyclopentyloxybenzene, hexyloxybenzene, cyclohexyloxy Benzobenzene, heptyloxybenzene, octyloxybenzene, 2-mercapto-anisole, 3-mercapto-anisole, 4-methylanisole, 4-ethylanisole, 4-propane Anisole, 4-butylanisole, 4-pentyl anisyl ether, 4-hexyl anisyl ether, diphenyl ether, 4-mercaptophenoxybenzene, 4-ethylphenoxybenzene , 4-propylphenoxybenzene, 4-butylphenoxybenzene, 4-pentylphenoxybenzene, 4-hexylphenoxybenzene, 4-phenoxyindoline, 3-phenoxytoluene , 1,3-dimethoxybenzene, 2,6-diindenyl anisole, 2,5-diindenyl anisole, 2,3-didecyl anisole and 3,5-diindole Base anis ether and so on. 88 323308 201211203 An aliphatic ether solvent: tetrahydrofuran, dioxane, dioxolane or the like. Ketone-based solvents: acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and acetophenone. The ester-based solvent is ethyl acetate, butyl acetate, methyl benzoate, and Ethyl cel losolve acetate. Chlorine-based solvent: dichloromethane, gas, 1,2-dichloroethane, 1,1,2-trichloroethane, gas benzene, and o-dichlorobenzene. Alcohol-based solvent: methanol, ethanol, propanol, isopropanol, cyclohexanol, phenol, and the like. Polyol and its derivatives: ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, Triethylene glycol monoethyl ether, glycerin and 1,2-hexanediol. Aprotic polar solvent, Dimethyl Sulfoxide, N-methyl-2-pyrrolidone, N,N-dimethyldecylamine, and mercaptoacetamide. These solvents may be used singly or in combination of two or more kinds as a mixed solvent. When used as a mixed solvent, it is preferred to combine two or more kinds from the above-mentioned solvent group. In this case, a plurality of solvent groups can be selected from the same system, or each of the different solvent groups can be used. Select more than one to combine. The composition ratio of the mixed solvent can be determined by considering the physical properties of each solvent and the solubility of a high molecular compound or the like. A preferred example of a mixed solvent obtained by combining a plurality of solvent groups from the same system is a mixed solvent and a mixture of aromatic ethers selected from the group consisting of a plurality of 323308 89 201211203. A mixed solvent in which a plurality of solvents are selected and combined. Preferred examples of the mixed solvent obtained by combining one or more of the self-dissimilared solvent groups include the following combinations. Combination of aromatic hydrocarbon solvent and aliphatic hydrocarbon solvent, combination of aromatic hydrocarbon solvent and aromatic ether solvent, combination of aromatic hydrocarbon solvent and aliphatic ether solvent, aromatic hydrocarbon solvent and aprotic Combination of a polar solvent and a combination of an aromatic ether solvent and an aprotic polar solvent. Further, water may be added to the above-mentioned separate solvent or mixed solvent. From the viewpoint of viscosity and film formability, it is preferably a single solvent or a mixed solvent, which comprises an organic solvent having a structure including a benzene ring, a melting point of o°c or less, and a boiling point of 100° C. or higher, wherein It is preferably a single solvent or a mixed solvent containing an aromatic hydrocarbon solvent or an aromatic ether solvent. The solvent may be a single solvent or a mixed solvent, but it is preferred to use a mixed solvent from the viewpoint of film formability. The solvent system can be purified by a purification method such as washing, distillation, or contact with an adsorbent. According to the liquid composition of the present invention, an organic film containing the above-mentioned high molecular compound can be easily produced. For example, the liquid composition of the present invention can be applied to a substrate, and the solvent can be distilled off by heating, air blowing or depressurization to obtain an organic film containing the polymer compound. The solvent removal conditions can be changed depending on the organic solvent to be used. In this case, for example, an ambient temperature (heating environment) of about 50 to 150 ° C and a reduced pressure environment of about 10 3 Pa can be mentioned. The suitable viscosity of the liquid composition of the present invention also varies depending on the printing method. 90 323308 201211203 is preferably 〇. 5 to 1 〇〇〇mpa · s, more preferably 〇 5 to 500 mPa at 25 C. s. Further, when the liquid composition of the inkjet printing method is passed through a discharge device, the viscosity of the liquid composition at 25 ° C is preferably 〇 5 to 50 mPa in order to prevent clogging or sneezing during discharge. s : More preferably 0.5 to 20 mPa · s. The content of the polymer compound of the present invention in the liquid composition is not particularly limited, and is preferably 〇1 to 1% by weight, more preferably 0.1 to 5% by weight. &lt;Film&gt; The film of the present invention contains a light-emitting film or a conductive film of the polymer compound of the present invention. The film system can be borrowed from: spin coating method, casting method, micro gravure coating method, gravure printing method, bar coating (Bar c〇ating) &amp; roll coating Method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic printing method, offset printing method, inkjet method, capillary coating (Capillary (10) ting The method and the nozzle coating method are used for production. When the film is formed by using the liquid composition of the present invention, it is also related to the glass transition temperature of the polymer compound contained in the liquid composition, but usually it can be carried out at a temperature of iooc or higher (for example, 13 (rc, (10).c). For the production of roasting. = The luminous quantum yield of the film of Ming, from the point of view of the brightness and illuminance of the element = 3 is better, the weight is better, 5 (UU is better, 6 〇% or more is particularly good. The surface resistance of the film is preferably 1 ΚΩ/Ε] or less, preferably 诵/□ or less, and □ or less. The film can be replaced with Lewis acid via 323308 91 201211203 or The ionic compound or the like improves the conductivity. <Light-emitting device> 70 of the present invention includes the polymer compound of the present invention, and has, for example, an electrode composed of an anode and a cathode, and the present invention provided between the electrodes The element of the organic layer of the molecular compound is described below. The case where the element of the present invention is a light-emitting element such as an organic EL element will be described. The light-emitting element of the present invention is a single-layer type light-emitting element (anode/ In the case of the light layer/cathode, the light-emitting layer is composed of the above-mentioned film, and the light-emitting layer contains the polymer compound of the present invention. Further, the light-emitting element of the present invention is a multilayer having two or more layers between the anode and the cathode. In the case of the above type, at least one of the layers is composed of the above-mentioned film. The layer configuration of the multilayer light-emitting device may be, for example, the following (a) to (c). (a) Anode/hole injection layer (hole) Transport layer) / luminescent layer / cathode (b) anode / luminescent layer / electron injection layer (electron transport layer) / cathode # (C) anode / hole injection layer (hole transport layer) / luminescent layer / electron injection layer. (electron transport layer)/cathode (herein, "/" means that each layer is adjacent to the laminate.) The anode of the light-emitting element of the present invention has a hole for supplying a hole to a hole injection layer, a hole transport layer, a light-emitting layer, or the like. Function: The foregoing anode is characterized by the above work function. The material of the anode may be a generic name, an alloy, a metal oxide, a conductive compound or a mixture of the same. Illustrative: tin oxide, zinc oxide, Conductive metal oxides such as indium oxide and oxidized _ (ITG); gold, silver, and 323308 92 201211203 recorded metals; mixtures or laminates of conductive metal oxides and metals; inorganic salts such as copper iodide and copper sulfide a conductive material; an organic conductive material such as polyaniline, polythiophene (PEDOT, etc.) or polypyrrole; a laminate selected from the above materials 1 or 2 and IT0. The cathode of the light-emitting device of the present invention has The electrons are supplied to the functions of the electron injecting layer, the electron transporting layer, the light emitting layer, etc. As the material of the cathode, a metal, an alloy, a metal halide, a metal oxide, a conductive compound or a mixture thereof may be used. For the materials, for example,: • metal (li, sodium, unloading, antimony, etc.) and its fluorides and oxides; soil-measuring metals (magnesium, calcium, barium, etc.) and its fluorides and oxides; Metals such as silver, lead, and aluminum; alloys and mixed metals (sodium-potassium alloy, sodium-potassium mixed metal, Li-Ming alloy, Li-Ming mixed metal, town-silver alloy, town-silver mixed metal, etc.) ; And rare earth metals (镱, etc.), indium. The hole injection layer and the hole transport layer of the light-emitting element of the present invention have any one of functions of injecting a hole from an anode, a function of transporting a hole, and a function of blocking electrons injected from a cathode. The materials of these layers are optionally made of known materials. Examples of such materials include, for example, a β-sodium derivative, a tris-salt derivative, a sputum derivative, a di-salt derivative such as hydrazine, a s-beta derivative, a polyaryl hydrocarbon derivative, and π. Specific salivation derivative, 嗤α弄 derivative, phenyldiamine derivative, arylamine derivative, amine substituted chalcone derivative, styryl hydrazine derivative, hydrazine a ketone derivative, an anthracene derivative, an anthracene derivative, a Si 1 azane derivative, an aromatic tertiary amine compound, a styrylamine compound, an aromatic secondary indenyl compound, a phosphonium compound, Polylithic compound, poly(N-ethylene 0 carbene) derivative, 93 323308 201211203 organic stone sinter derivative and polymer containing the same; aniline (Ani 1 ine) copolymer, thiophene oligomer And a conductive polymer oligomer such as polythiophene. The above materials may be used alone or in combination of two or more. Further, the hole injection layer and the hole transport layer are independent of each other, and may be a single layer structure composed of one or two or more of the foregoing materials, or may be a multilayer structure composed of a plurality of layers of a single composition or a different composition. The electron injecting layer and the electron transporting layer of the light-emitting element of the present invention have any one of functions of injecting electrons from a cathode, functions of transporting electrons, and functions of blocking holes injected from a positive electrode. The materials of these layers are optionally made of known materials. Examples of such materials include, for example, a triazole derivative, a guanidine derivative, an anthraquinone derivative, a saliva derivative, an anthrone derivative, a scallion derivative, an anthrone derivative, and Diphenyl ikon derivative, oxidized β-Seran derivative, carbodiimide derivative, fluorenylene derivative, bis(styryl)pyrylene derivative, naphthalene and anthracene Carboxylic acid liver; anthraquinone derivative, metal complex (for example: 8-metal complex of quinone-derived I; metal agglomerate with metal phthalocyanin and benzoxazole as ligands; Benzothiazole as a metal complex of the ligand) and an organodecane derivative. The electron injecting layer and the electron transporting layer are independent of each other, and may be a single-constituent structure composed of one or more of the above materials, or a multi-layered structure composed of a plurality of layers of a single composition or a different composition. Further, as the light-emitting element of the present invention, an inorganic compound such as an insulator or a semiconductor can be used as the material of the electron injecting layer and the electron transporting layer. The electron injecting layer and the electron transporting layer are composed of an insulator or a semiconductor, which can effectively prevent current leakage and improve electron injectability. In the above-mentioned insulator 94 323308 201211203, for example, it is selected from the group consisting of a sulfide metal, a diarrhea metal, an alkali metal tooth, and a halide of a soil-measuring metal.丨, a metal compound. Preferred examples of the alkali metal sulfide include CaO, BaO, SrO, BeO, BaS, and CaSe. Further, in terms of a semiconductor constituting an electron, a main layer, and an electron transport layer, for example,

Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta,

An oxide, a nitride, and an oxidized IL compound of at least one element of the group consisting of Sb and Zn. These oxides, compounds, and oxynitrides may be used alone or in combination of two or more. The light-emitting element of the present invention is capable of adding a reducing dopant to the interface region between the cathode and the film attached to the cathode. The reducing dopant is preferably an alkali metal, an alkaline earth metal oxide, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal complex, an alkaline earth metal oxide, or an alkaline earth metal. Halide of halides, rare earth metals, rare earth metals

The substance, the alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex constitute at least one compound in the group. When the light-emitting layer of the light-emitting element of the present invention is applied with a voltage, the hole can be injected through the pole, the hole injection layer or the hole transport layer, and has the following month b, ''two by the cathode, the electron injection layer or The ability of the electron transport layer to inject electrons; the function of moving the injected charge (electrons and holes) by the force of the electric field and the place where the electrons and the electric society are recombined, and (4) the function of the light-emitting function, the light-emitting element of the invention The layer is preferably one containing at least the polymer compound of the present invention. The polymer compound phase in the light-emitting layer: the weight of the entire light-emitting layer, usually 1 G weight% to 100 weight 323308 95 201211203 5 〇 weight to 1 〇 0% by weight, preferably 80% by weight to 1% by weight In the light-emitting element of the present invention, it is preferred that the light-emitting layer contains the polymer compound of the present invention as a light-emitting material. The light-emitting element of the present invention is not particularly limited to a method in which the formation of each layer described above can be used. Examples of the method include: a steaming method (resistance addition or subtraction method, electron beam method, etc.), Miscellaneous method, lb method, molecular lamination method, coating method (casting method, spin coating method, bar coating method, blade coating method, roll coating method, gravure printing, screen printing, inkjet method, etc.) In the coating method, the polymer compound of the present invention is dissolved in a solvent to prepare a coating liquid, and the coating liquid is prepared by the coating method. The coating liquid is formed by coating and drying on a desired layer (or electricity:). The coating liquid may contain a resin which is a binder, and may dissolve and disperse the impurities. In other words, it is possible to use a non-co-tetrazed or a polymer (for example, a polyethylene ray or a sulphide molecule (for example, a polyolefin-based polymer). More specifically, for example, poly-glycolized ethylene or polycarbonate , polystyrene, polymethyl methacrylate, polybutyl methacrylate , polyester, polysulfone, polyphenylene ether, polybutylene = ethylene, hydrocarbon resin, ketone resin, phenoxy resin, polyamine, = vitamin, vinyl acetate, ABS resin, _, melamine tree Two Mela_ resin; melamine resin), unsaturated polyester resin, alcohol I resin, epoxy resin and 11 oxygen (SiUeQne) _ can be selected according to the purpose. The coating liquid can contain any antioxidant gambling agent according to the purpose. The preferred thickness of each layer of the light-emitting element of the invention is different depending on the type of the material 323308 96 201211203 or the layer composition, but usually is from 1 nm to 10 nm, and is from several nm to l//m. In the use of the light-emitting element of the present invention, a planar light source, a light source for illumination (or a light source), a light source for a sign, a light source for backlight, a display device (display device), and printing can be exemplified. For the display device, a known driving technique, a drive circuit, or the like can be used, and a segment type, a dot matrix type, or the like can be selected. (Example) The following According to the embodiment, the invention is further The present invention is not limited to the following examples. (Quantum average molecular weight and weight average molecular weight) The number average molecular weight and the weight average molecular weight are determined by size exclusion chromatography (SEC). The number average molecular weight and the weight average molecular weight in terms of polystyrene. When the mobile phase of φ in the SEC is an organic solvent, it is called gel permeation chromatography (GPC). Further, based on the analysis conditions of the GPC. In other words, the following analytical conditions are used or the method shown in Condition 2 is analyzed. [Analysis condition 1]

The measurement sample was dissolved in tetrahydrofuran at a concentration of about 5% by weight. The obtained solution 30//L was injected into GPC (manufactured by Shimadzu Corporation, trade name: LC-lOAvp). In the mobile phase of GPC, tetrahydrofuran was used to make it flow at 6 mL/min. The tube is composed of two TSKgel SuperHM H (T〇s〇H 323308 97 201211203) and one TSKgel SuperH2000 (manufactured by TOSOH). The detector used was a refractive index difference detector (manufactured by Shimadzu Corporation, trade name: RID-l〇A). [Analysis condition 2]

The test sample was dissolved in tetrahydrofuran at a concentration of about 0.05% by weight. 10 μL of the obtained solution was poured into GPC (manufactured by Shimadzu Corporation, trade name: LC-lOAvp). The mobile phase of the GPC was flowed using a tetrahydrofuran at a flow rate of 2.0 mL/min. For the column, PLgel MIXED-B (manufactured by POLYMER H Laboratories) was used. The detector was a UV-VIS detector (trade name: SPD-lOAvp, manufactured by Shimadzu Corporation). (NMR measurement) The NMR measurement of the examples was carried out under the following conditions. Apparatus: NMR apparatus, INOVA300 (trade name), Varian company measurement solvent: deuterated chloroform φ sample concentration: about 1% by weight Determination temperature: 25 ° C (high-speed liquid column chromatography) Example of high-speed liquid tube Column chromatography (hereinafter referred to as "HPLC") was carried out under the following conditions. Device: LC-20AC trade name), Shimadzu Manufacturing Co., Ltd.: Kaseisorb LC ODS-AM 4. 6mml. D. xl〇〇mm, Tokyo Chemical System mobile phase: containing 0.1% by weight of acetic acid / containing strontium. 1 wt% acetic acid 323308 98 201211203 acetonitrile detector. UV detector, detection wavelength 254 nm (gas phase column chromatography) The gas phase column chromatography (hereinafter referred to as "GC") of the examples is based on the following conditions. get on. Device · Agilent Technology 6890N Network GC Column · BPX5 0. 25mml. D. x30m, SGE Analytical Science System # Mobile Phase: Helium Detector: Hydrogen Flame Free Detector (FID) (Evaluation of Luminescence Spectrum Peaks) Example The sizing of the luminescence spectrum peak of the luminescent organometallic conjugate compound is carried out in the following manner unless otherwise specified. A fluorinated luminescent compound is dissolved in diphenylbenzene (manufactured by Kanto Chemical Co., Ltd.: for the electronics industry (electronic grade)). At this time, the concentration of the solid content was adjusted to be a solution of 重 8 wt%. This solution was excited at a wavelength of 350 nm using a fluorescence spectrophotometer (manufactured by JASCO Corporation, FP-6500), and the spectrum of the luminescence spectrum was evaluated by measuring the PL spectrum of the solution. (Measurement of MALDI-T0FMS) The measurement of MALDI-T0FMS was carried out under the following measurement conditions 1. [Measurement Condition 1] The cyano-4-hydroxy cinnamate was dissolved in decyl alcohol to prepare a saturated solution, which was used as a matrix solution. The polymer compound to be measured 323308 99 201211203 200//L of chloroform was added to about 4 mg and dissolved, and the obtained solution 20 &quot;L was diluted with 200 μL of chloroform to dilute the solution as a sample solution. Mix 20L of matrix solution with sample solution 20 μL, mix this mixture

The combined solution was applied to a MALDI plate (MALDI Plate) for MALDI-TOFMS measurement. The measurement was performed using a MALDI-TOFMS apparatus: Voyager-DE STR (Applied Biosystems), and the measurement mode: Reflector, acceleration voltage: 20 kV, and laser: N2 (337 nm). &lt;Synthesis Example 1&gt;

(Synthesis of Compound M-1)

-c X

In a argon atmosphere, 1,4-dihexyl-2,5-di-benzene (compound CM-1, 8. 08 g, 20. Ommol), bis(pinacol) diboron ( Bis(pinacolato)diboron)(12.19g » 48. Ommol) ' [1, Γ-bis(diphenylphosphino)pyrene]dichloropalladium (Π) (〇·98g, L 2mm〇1), potassium acetate (11. 78 g, 120. Ommol) and dehydrated 1,4-di-pf alkane (i〇〇mi) were stirred under reflux for 6 hours. Toluene and ion-exchanged water were added, and the mixture was separated and washed with ion-exchanged water. Anhydrous sodium sulphate and activated carbon were added and filtered through a funnel precoated with Celite. The filtrate was concentrated to give a crude product (ll_94 g). Recrystallization was carried out with hexane, and ?, β BB was washed with methanol. By drying the obtained crystal by ink reduction, 1,4-dihexyl-2,5-bis(4,4,5,5-tetradecyl-1,3,2-di which is the object of 323308 100 201211203 is obtained. White needle crystals of oxaborolan-2-yl)benzene (4.23 g, yield 42%, compound M-1). The results of 1H-NMR analysis of the compound M-1 and the results of LC/MS are shown below. !H-NMR (300MHz, CDCh): &lt;5 (ppra)=0. 95 (t&gt; 6H) q. 39-1. 42 (bd, 36H), 1.62 (m, 4H), 2.88 (t, 4H) ), 7.59 (bd, 2H) LC/MS (addition of ESi p〇si KC1): [M + K]+573 &lt;Synthesis Example 2&gt; (Synthesis of Compound M-2)

A small amount of dehydrated tetrahydrofuran and 1,2-dibromoethane (1., 8 mmol) were sequentially added to a small piece of magnesium (19.45 g, 8 〇〇 imn (1)) in a flask under an argon atmosphere. After confirming that the magnesium has been activated by heat and foaming, the dehydrated tetrahydrofuran (2〇〇ml) is dissolved in 2,6-two-soil (2. The solution is dripped. After the completion of the dropwise addition, the mixture was heated in an oil bath of 8 Torr and stirred under reflux for several hours. After taking out from the oil bath, it was diluted with dehydrated tetrahydrofuran (400 ml), and after cooling in an ice bath, 2 isopropyloxy-4,4,5,5-tetramethyl-1,3,2-diox was added. Production of heteroboron (148.85 g, 8 mmol). It was taken out from the ice bath and heated in an oil bath of 80 ° C and stirred under reflux for 1 hour and a half. Remove from the oil bath, and then cool with water 323308 101 201211203 bath, add saturated aqueous solution of ammonium carbonate (5 〇 ml), give 3 ounces, take out from the ice bath, add hexane (1500ml) 'Strongly mix 3 〇八t刀在内0•^7 Stir in the nursery rhymes 4 mouth and let stand for 15 minutes, then filter with a glass filter filled with silicone rubber. Wash the silicone with hexane (1000ml). The artificial solution was concentrated under reduced pressure to give a crude product (72· g). The reaction was carried out again to give a crude product (75. 4 g). Next, methanol (74 〇 ml) is added to the total of the crude products.

The 85 t: oil bath was stirred under heating and reflux for 1 hour. After taking out from the oil bath, it was cooled to room temperature with stirring, and the solid was filtered, washed with methanol, and dried under reduced pressure to give white crystals (59.7 g). After the dried crystals were dissolved in isopropyl alcohol, the mixture was cooled to room temperature by the standing state. The crystals were precipitated. After filtration, the mixture was washed with methanol, and dried at 5 TC for one night. The white crystals of the compound M-2 (50.8 g, HPLC area (ultraviolet wavelength: 254 nm): 99.8%, yield 37%) were obtained as a target compound. The results of 1H-NMR analysis of the compound M-2 are as follows Shown. ^-NMR (300MHz &gt; CDCh) &lt;5 (ppm) = l. 34 (s&gt;24H)&gt; 2. 74 (s 3H), 7.14 (t, 1H), 7.79 (d, 2H) &lt; Synthesis Example 3 &gt; (Synthesis of Compound M-3) • Compound CM-3 &lt; Synthesis: The gas inside the 4-necked flask was replaced with nitrogen, and 2,7-dibromo (1 equivalent) was added to suspend the diphenyl group. Ether (27 eq.). The resulting suspension was heated to 120 ° C to dissolve 2,7-dibromofluorenone, and then hydrogen peroxide (5.7 eq.) was added thereto, and the temperature was raised to 160 ° C. After stirring for 2.5 hours, it was allowed to cool to room temperature 102 323308 201211203 and then added to 23 equivalents, and after filtration, the crude product was obtained by itself. The gas inside the 4-necked flask was replaced with nitrogen, and the crude product was allowed to dissolve in dehydrated DMF (4 G equivalent). After the obtained temperature was raised to 9 G ° C, iodine (7. 7 equivalents) was slowly added. Reaction Η) hours. The obtained reaction solution was allowed to cool to room temperature, and then dropped into water (340 equivalents) of cold = 0 C, and extracted twice with hexane (46 equivalents), and the resulting extract was filtered with a glass of Na Na. The resulting organic layer was concentrated. The organic layer concentrate was purified by column chromatography to obtain the compound CM_3 (yield: 74%) of the following formula; the result of 1H-NMR analysis of the C〇2Me compound CM-3 and 13c- The results of the nmr analysis are as follows. 'H-NMR (300MHz/CDCh): (5 (ppm) = 3.68 (s, 3H), 7.15 (d, 2H), 7.20 (d, 1H), 7.52 (d, 2H), 7.65 ( d, 1H), 8.00 (brs, 1H) 13C-NMR (300MHz/CDCh): 5 (ppm) = 52. 匕121. 8&gt; 122. 2, 130. 1, 131. 6, 132. 丄 132. 4 133. 2,134. 7,139.4,140. 6,167.8 • Synthesis of compound CM-4 was charged in a 3-neck round bottom flask with 1-bromo-4-n-hexylbenzene (1 equivalent) and anhydrous tetrahydrofuran (hereinafter also Recorded as THF) (34 eq.), cooled to -78. (:: This was slowly charged with n-butyllithium (n-BuLi) (1.6 M hexane solution) (1 eq.) to 103 323308 201211203 -78° C was stirred for 2 hours to obtain a reaction liquid. A solution of the compound CM-3C0. 43 eq. in anhydrous THF (5.6 eq.) was placed in a dropping funnel so that the temperature of the reaction liquid did not exceed -7 ° C. At the dropping speed, the mixture was dropped. After the completion of the dropwise addition, the mixture was stirred at the same temperature for 2 hours, and slowly warmed to room temperature. Thereafter, about half of the volume of anhydrous THF with a saturated aqueous solution of ammonium chloride was added and stirred, and then transferred. Dispense the funnel and remove the water layer. Wash the resulting organic layer with water 2 : owing, the obtained organic layer was added with anhydrous sodium sulfate and dried. The layer of the silica gel was applied to a glass filter, filtered through a THF solution, and washed with THF. The resulting solution was concentrated and dried. The product was washed by repulp with hexane to obtain a compound CM-4 represented by the following formula (yield 27%);

• Synthesis of Compound M-3 A three-necked flask was charged with compound cm-4 (1 eq.) and dichloromethane (38 eq.) and cooled to &lt;RTIgt; Boron trifluoride diethyl ether complex (22 equivalents) was placed in a dropping funnel and then dropped. The reaction solution was stirred at 〇 °c for 2 hours, and then poured into a beaker containing water and ice to stop the reaction. The reaction mixture was transferred to a separatory funnel to carry out liquid separation, and the mixture was extracted with dichloromethane, and then washed twice with water and dried over anhydrous sodium sulfate. The glass filter was applied with a layer of Shixi gum, filtered through a solution of THF, and concentrated in 104 323308 201211203. Toluene was added to the obtained oil and heated to reflux. Next, after cooling to 70 ° C, isopropyl alcohol was added and stirred, and the mixture was allowed to stand at room temperature to cause crystallization. This crystal was filtered, dried, and placed in a pear-shaped flask. After heating with hexane and activated carbon, the mixture was heated under reflux for 2 hours to obtain a mixture. The mixture was filtered by applying a sodium zeolite (Radiol ite) to a glass filter and coating it with diatomaceous earth by heating to 70 ° C in an oven. The resulting solution was concentrated to a half amount, and the concentrate was heated to reflux, and then stirred at room temperature for 1 hour. Further, while stirring with an ice bath, while stirring for 2 hours, the resulting crystals were collected by filtration, and the compound M-3 (yield: 92%) of the following formula was obtained;

The results of 1H-NMR analysis of the compound M-3 and the results of 13 C-NMR analysis were as follows. R (300MHz/CDC13): 5 (ppm) = 0.87 (t, 6H), 1.28~1.37 (m, 12H), 1.50~1.62 (m, 4H), 2.54 (t, 4H), 7.04 (s, 8H) ), 7.45 (d, 2H), 7.49 (s, 2H), 7.55 (d, 2H) 13C-Li R (300MHz/CDC13): (5 (ppm) = 14.4, 22.9, 29.4, 31.6, 32.0, 35.8, 65.4, 121.8, 122.1, 128. 1, 128.7, 129.7, 131.1, 138.3, 141.9, 105 323308 201211203 142. 1, 153.7 7 &lt;Synthesis Example 4 &gt; (Synthesis of Compound Μ-4)

Br

n-BuLi Et20

CI^N^CI ΝγΝ Cl

Et20

A solution of 1,4-dibromobenzene (27. lg) in dehydrated diethyl ether (217 ml) was cooled using a dry ice/methanol mixture bath under nitrogen. To the obtained suspension, 2.77 M of n-butyllithium (n-BuLi) in hexane (37. 2 ml) was slowly dropped, and the mixture was stirred for 1 hour to prepare a lithium reagent. Under a nitrogen atmosphere, a suspension of cyanuric chloride (10.Og) in dehydrated diethyl ether (68 ml) was cooled using a dry ice/sterol mixed bath, and the lithium reagent was slowly added thereto, and then the temperature was raised to room temperature. Allow to react at room temperature. The resulting product was filtered and dried under reduced pressure. The obtained solid (16.5 g) was purified to obtain 13.2 g of needle crystals (Compound CM-11).

Βγ〇ι2η25^3&quot;Μ9Βγ

C12H25 M-4 A small amount of 4-dodecylbromobenzene (14.2 g) dehydrated tetrahydrogen bite was added successively to a magnesium (1.37 g) suspension with dehydrated tetrahydrofuran (65 ml) under nitrogen. The solution (15 ml) was heated, and the mixture was placed under reflux. Put 106 323308 201211203 After cooling, add magnesium (Q. 39g) to the reverse m, and then: heat up, make it ride back under the reflux, and prepare it into a Grignard reagent. The above-mentioned genomic reagent was added to the dehydrated tetrahydro-α-propan (10) (4) solution of the pre-suspension crystals (12.Gg, compound CM_U) while stirring under a nitrogen atmosphere, and heated to reflux. After allowing to cool, the solution was washed with a dilute aqueous solution of hydrochloric acid. After the organic layer was separated from the aqueous layer, the aqueous layer was extracted with diethyl ether. The organic layers were washed again with water, and the organic layer was removed with anhydrous magnesium sulfate and filtered and concentrated. 5克的化合物 M,4。 The resulting white solid was purified by a column of 矽 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 &lt;Synthesis Example 5 &gt; (Synthesis of Compound M-5) In the same manner as in Synthesis Example 4, 13.2 g of needle crystals (Compound CM-11) was obtained.

Add a small amount of 4-hexylbromobenzene (14.2 g) of dehydrated tetrahydrofuran to a suspension of dehydrated tetrahydroanthracene (65 ml) in magnesium (1. 37 g) under nitrogen atmosphere. After the solution (15 ml), it was heated and stirred under reflux. After cooling, magnesium (0.39 g) was added to the reaction solution, and the mixture was heated again under reflux to make a reaction. Under the nitrogen atmosphere, the above-mentioned needle crystal (1. Og) of dehydrated tetrahydro D-propan (10Om 1) suspension was stirred while adding the above-mentioned gejjj reagent, and heated to reflux. After allowing to cool, the reaction solution was washed with a dilute aqueous hydrochloric acid solution. After the organic layer was separated from the aqueous layer, the aqueous layer was extracted with diethyl ether. The obtained organic layer was washed again with water, and the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The obtained white solid was purified by a silica gel column, to give a white solid compound M-5 (6.5 g).

The results of 1 H-NMR analysis of the compound M-5 are shown below. ^-NMR (300MHz, CDC13): J (ppm) = 0.90 (t, J = 6. 2Hz, 3H), 1. 25-1. 42 (m, 6H), 1. 63-1. 73 ( m, 2H), 2.71 (t, J=7·6Hz, 2H), 7.34 (d, J=7.9Hz, 2H), 7.65 (d, J=7.9Hz, 4H), 8.53-8. 58 ( m, 6H) LC-MS (APCI, positive): m/z+=566 [M + H] + &lt;Synthesis Example 6 &gt; (Synthesis of Compound M-6)

(wherein Me represents a fluorenyl group.) In a reaction vessel in which the internal gas is replaced by nitrogen, palladium (II) acetate (0.90 g), ginseng (2-mercaptophenyl)phosphine (2.435 g), and toluene (125 mL) are added. ), stirring at room temperature for 15 minutes. 2,7-Dibromo-9,9-dioctylindole 108 323308 201211203 (27.4 g), (4-methylphenyl) strepamine (22.91 g) and sodium butoxide (t-) were added thereto. BuONa, 19.75g) 'After heating to reflux for one night, cool to room temperature, and add water to wash. The organic layer was taken out and the solvent was distilled off under reduced pressure. The residue was dissolved in toluene, and the resulting solution was passed through an Alumina column. The precipitate was concentrated under reduced pressure, and decyl alcohol was added thereto to cause precipitation. The precipitate was collected by filtration and recrystallized from p-diphenylbenzene. The crystals were redissolved in a solution and the resulting solution was passed through an alumina column. After the solution was concentrated, a Φ precipitate was produced when injected into the stirred sterol. The precipitate was collected, and after drying at room temperature for 18 hours, white 2,7-bis[N-(4-mercaptophenyl)-N-phenyl]amino-9, 9- Dioctyl hydrazine (25. Og). Adding 2,7-bis[1^-(4-methylphenyl)4-phenyl]amino-9,9-dioctylfluorene 12.52 with di-methane in a reaction vessel in which the internal gas is replaced by nitrogen 95 mL of the reaction solution was cooled to ~10 ° C while stirring. Thus, a solution of N-bromosuccinimide φ (NBS) 5.91 g of 20 mL of dimethyl decylamine (DMF) was slowly dropped. After stirring for 3.5 hours, the mixture was mixed with cold methanol, and the resulting sink was recrystallized by p-diphenyl. The obtained crystals were recrystallized again using toluene and methanol to give a white solid as compound M-6. 12. lg ° The result of 1H-NMR analysis of compound M-6 is shown by T. Ή-NMR (300MHz, CDCh): 5 (ppm)=0. 61-0. (ιη' 4H)' 〇.86 (t, J=6.8Hz, 6H), 0.98-1.32 (m, 2〇H) , 丨·72-1·?? (m, 4H), 2. 32 (br, 6H), 6. 98-7. 08 (m, 16H), 7. 29 (d, J = 8.3 Hz, 4H) 7.44 (br, 2H) 323308 109 201211203 &lt;Synthesis Example 7 &gt; (Synthesis of Compound M_7) • Synthesis of Compound CM-5 The gas inside the 3-neck flask was replaced with nitrogen to measure 1-bromo-3-n-hexyl Benzene (1 equivalent) was dissolved in dehydrated tetrahydrofuran (33 equivalents). The obtained solution was cooled to -75 ° C or lower, and 2.5 M n-butyllithium / n-hexane solution (0.95 equivalent) was added dropwise while stirring at -75 ° C for 5 hours. While maintaining the temperature below -70 ° C, 2-methyl oxycarbonyl-4, 4'-dibromobiphenyl (〇. 43 equivalent) of dehydrated tetrahydrofuran (5.3 eq.) was dissolved in the obtained solution. The solution was dripped. The obtained solution was gradually warmed to room temperature, and then stirred overnight. While stirring the reaction solution at 〇 ° C, water was dropped there. After distilling off the solvent, water was added to the residue, and hexane was extracted once with hexane twice. The organic layer was washed with saturated brine, and the aqueous layer was re-extracted with hexane. The organic layer was dried over magnesium sulfate. After distilling off the solvent, a crude product of the compound CM-5 represented by the following formula (4290,

CM-5 This crude product was not refined and was used in the next step. Further, 2-methoxycarbonyl-4,4'-dibromobiphenyl is synthesized by the method described in Journal of the American Chemical Society (1956), 78, 3196-3198. 110 323308 201211203. • Synthesis of Compound CM-6 Compound CM-5 (1 eq.) was weighed to a 3-neck flask, dichloromethane (35 eq.) was dissolved, and the gas in the flask was replaced with nitrogen. The obtained solution was cooled to 0 ° C or lower, and a boron trifluoride diethyl ether complex (4.8 equivalent) was added dropwise while keeping the temperature at 5 ° C or lower. After slowly warming to room temperature, stirring was carried out overnight. The reaction solution was poured while stirring in ice water, and stirred for 30 minutes. The resulting solution was separated and the aqueous layer was extracted with dichloromethane. The organic layer was added together with a 10% by weight aqueous potassium hydroxide solution and liquid-separated, and the organic layer was washed twice with water. After the organic layer was dried over magnesium sulfate, the oil obtained by distilling off the solvent (Oil) was dissolved in toluene, and filtered through a glass filter coated with silicone. After distilling off the solvent, methanol was added and stirred vigorously. The resulting crystals were filtered and washed with methanol. The compound CM-6 represented by the following formula was obtained by recrystallization from a mixed solvent of hexane/butyl acetate (yield: 47%);

The results of1H-NMR analysis of the compound CM-6 are shown below. 'H-NMR (300MHz, CDCh); 5 (ppm) = 0.86 (6H, t), 1.26 (12H, m), 1. 52 (4H, m), 2. 51 (4H, t), 6 87 (2H, d), 7. 00 (2H, s), 7. 04 (2H, d), 7. 12 (2H, t), 7.46 (2H, dd), 7.48 (2H, d), 7 . 55 (2H, d) ppm • Synthesis of compound M-7 111 323308 201211203 Gas. Dehydrated tetrahydrofuran (80 equivalents) was added thereto and cooled to -70 ° C or lower. 5的含含锂和含乙溶液之间。 (2. 2 equivalent) while the solution was kept below -70 ° C, while dropping 2. 5M n-butyl lithium / n-hexane solution (2.2 equivalents). After the dropping, the mixture was stirred for 4 hours while maintaining the temperature. After adding 2-isopropyloxy-4,4,5,5-tetradecyl-1,3,2-dioxaborolane (3.9 eq.), slowly warmed to room temperature and Stir in the night. The reaction solution was cooled to -30 °C. After dropping 2M hydrochloric acid/diethyl ether solution (2 equivalents), the mixture was warmed to room temperature. After distilling off the solvent, toluene was added and dissolved, and the mixture was filtered through a glass filter coated with silicone, and the solvent of the obtained solution was distilled off to obtain a crude product. By recrystallization from a toluene/acetonitrile solvent in a nitrogen atmosphere, a compound M-7 represented by the following formula was obtained (yield 60%);

The results of1H-NMR analysis of the compound M-7 are shown below. W-NMRUOOMHz, CDCl3); 5 (ppm) = 0.86 (6H, t), 1.26-1.29 (12H, m) &gt; 1. 31 (24H, s)&gt; 1. 52-1. 53 (4H, m ), 2. 50 (4H, t), 6.92 (2H, d), 7.00 (2H, d), 7.08 (2H, t), 7.13 (2H, s), 7.77 (2H, d), 7.81-7.82 ( 4H, m) &lt;Synthesis Example 8 &gt; (Synthesis of Compound M-8) • Synthesis of Compound CM-8 112 323308 201211203 • Synthesis of Compound CM-8

Under a nitrogen stream, 1_glysin-3,5-di-n-hexylbenzene (1 equivalent) and tetrahydrofuran (36 equivalents) were charged in a reaction vessel to prepare a homogeneous solution, and the solution was cooled to -69 °C. 5小时。 The solution was stirred at -70 ° C for 1.5 hours. Next, a solution of the compound CM-3 (0.4 equivalent) and tetrahydronethane (3.6 equivalent) was dropped at -70 ° C for 1 hour, and stirred at -70 ° C for 2 hours. . Next, decyl alcohol (2.4 equivalent) and distilled water (5.5 eq.) were added at -70 ° C and stirred, and the mixture was warmed to room temperature and stirred overnight at room temperature. Next, the mixture was filtered, and the filtrate was concentrated, and heptane and water were added and stirred, and the aqueous layer was allowed to stand and the organic layer was removed from the liquid layer. φ was added to the organic layer with saturated brine and stirred, and the aqueous layer was allowed to stand and the aqueous layer was removed from the separated liquid layer. After adding magnesium sulfate to the organic layer and stirring, the filtrate obtained by filtration was concentrated to give the desired compound CM-8 (yield: 46%). • Synthesis of compound CM-9 113 323308 201211203

Compound CM_8 (1 equivalent) and dichloromethane (29 equivalents) were charged to a reaction vessel under a stream of argon to prepare a homogeneous solution and cooled. Boron trifluoride diethyl ether complex Φ (BIV0Et2, 1 equivalent) was added dropwise to the solution over a period of 30 minutes. Thereafter, the mixture was stirred at room temperature for one night. Next, the reaction mixture was cooled to -2 (Tc, stirred for 1 hour by adding distilled water (112 equivalents), and after standing, the aqueous layer was separated from the organic layer. Water (57 §) was added and stirred, and the aqueous layer was separated from the organic layer after standing. To the obtained organic layer, a 1% by weight aqueous solution of sodium hydrogencarbonate (22 equivalents) was added and stirred. After the separation, the water layer is removed from the organic layer. The organic layer is concentrated and the solvent is removed. Next, the toluene and the heptane are used as a stripping agent to be purified by (4) column chromatography, and the residue is removed after concentration. Next, #recrystallized from butyl acetate and methanol to obtain the intended compound CM-9 (yield 57%).

Under a stream of argon, 'in a 4-neck flask, compound CM_9 (1 equivalent), compound CM-10 (2.2 equivalents), 1,4-dioxane (87 equivalents), potassium acetate 323308 114 201211203 (6.1 equivalents) , 1,1'-bis(diphenylphosphino)pyrene (dppf '1.5mol%) and 1, bis-bis(diphenylphosphino)pyrene two gas (Η) dichloromethane complex (PdCl2dppf_CH2Cl2 '1·5πι〇1%) ' and disturbed for 5 hours from 1〇〇 to 102C. Next, the obtained reaction mixture was cooled to room temperature, and then subjected to filtration through a filter packed with Shixiazao and Shishijiao, and the obtained filtrate was concentrated to remove the solvent. Next, activated carbon was added to a solution prepared by adding hexane, and hexane was stirred at reflux temperature for 1 hour. After cooling to room temperature, the mixture was filtered through a filter packed with Shixia, and concentrated to remove the solvent. # Next, by recrystallization from toluene and acetonitrile, the intended compound Μ-8 (95%) was obtained. &lt;Synthesis Example 9&gt; (Synthesis of Compound Μ-9)

In a separable flask (Separable f lask) in which the internal gas was replaced by argon gas, compound L-5 (4. Og, 8.5 mmol), compound CM-1 (16 g, 37·6 mmol), hydrazine (three) Phenylphosphine)palladium (Pd(PPh3)4, 494 mg, 0.43 mmol, 5 mol%), toluene (780 mL) and ethanol (260 mL) were heated to 35 ° C while stirring. Next, an aqueous solution in which potassium carbonate (3.44 g, 26 mmol) was dissolved was added dropwise to ion-exchanged water (260 mL), followed by stirring for 64 hours. The reaction solution was transferred to a separatory funnel, and washed with ion-exchanged water and 1% by weight of sodium chloride. The organic layer was dehydrated with sodium sulfate and passed through a funnel filled with 矽115 323308 201211203 glue, and the solvent was distilled off under reduced pressure. except. The obtained residue was purified by medium pressure separation column chromatography (tank column, developing solvent: chloroform / hexane = 4 / 6 (volume ratio)), and then recrystallized with benzene, by vacuum dryer The obtained solid was sufficiently dried to give a white powder (1.5 g, yield 24%) of M. Further, the compound L-5 was synthesized in accordance with the method described in W002/66552. &lt;Synthesis Example 10&gt; (Synthesis of Compound M-10)

In a separable flask in which the internal gas was replaced by argon gas, a compound CM-13 (4. Og, 4.5 mmol), a compound CM-ll (8.4 g, 20. 〇mm〇i), φ 肆 (triphenyl) was added. Phosphide: palladium (〇) (Pd(PPh3)4, 26lmg' 〇. 23 〇 〇 、, 曱 benzene (780mL) and ethanol (260mL) 'One side of the disturbed side heated to 35 ° C β Next, the ion exchange An aqueous solution of potassium carbonate (丨.87 g, 14 mmol, 3 equivalents) dissolved in water (260 mL) was added dropwise and stirred for 23 hours. The reaction solution was transferred to a separatory funnel to wash with ion-exchanged water and 10% by weight saline. The organic layer was dehydrated with sodium sulphate, and then circulated in a funnel filled with lycopene, and the solvent was distilled off under reduced pressure. After the above-mentioned work was carried out twice, the residue obtained was weighed, and the residue was 323308 116 201211203 slag. The total amount of the residue was 22 g. The residue was purified by medium pressure separation column chromatography (purine column, solvent: gas/hexane = 4/6 (volume ratio)), and then repulped with hexane. Net and hot filtration, the resulting powder is sufficiently dried by a vacuum dryer to obtain white for the purpose of M-10. Powder (5g, Yield 50%) &lt;. Synthesis Example 11 &gt; (light emitting organic metal complex compound body Synthesis of MC-1)

The luminescent compound A was synthesized in accordance with the synthesis described in International Publication No. 2002/066552. Specifically, it is a Suzuki coupling of 2-bromopyridine with 1.2 equivalents of 3-bromophenylboronic acid in a nitrogen atmosphere (catalyst: hydrazine (triphenylphosphine) palladium (0), base: 2M sodium carbonate Aqueous solution, solvent: ethanol, toluene), 2-(3'-bromophenyl)pyridine represented by the following formula;

Next, under a nitrogen atmosphere, a coupling of tribromobenzene with 2.2 equivalents of 4-tributylphenylboronic acid Suzuki (catalyst: hydrazine (triphenylphosphine) palladium (0), base: 2M sodium carbonate aqueous solution, solvent: ethanol, toluene) to obtain a desert compound represented by the following formula;

After dissolving the above bromine compound in anhydrous THF under a nitrogen atmosphere, it was cooled at 117 323 308 201211203 at -78 ° C, and a slight excess of butyllithium was dropped. Under cooling, B(0C4H9)3 was added dropwise to carry out the reaction at room temperature. After the obtained reaction liquid is post-treated with 3M hydrochloric acid water, a boric acid compound represented by the following formula is obtained;

b(oh)2 is coupled with 1.2 equivalents of the above-mentioned succinic acid compound by a 2-(3'-indolyl) ratio (catalyst: hydrazine (triphenylphosphine) palladium (0), base: 2M sodium carbonate aqueous solution, solvent: ethanol, toluene), to obtain a ligand represented by the following formula (that is, a compound which becomes a ligand);

IrCl3.3H2 hydrazine and 2.2 equivalents of the above ligand, 2-ethoxyethanol and ion-exchanged water were placed under an argon atmosphere to reflux. The precipitated solid was subjected to suction filtration. The obtained solid is washed in the order of ethanol and ion-exchanged water, and then dried to obtain a yellow powder which is a compound represented by the following formula; 118 323308 201211203

2 equivalents of the above ligand and 2 equivalents of silver trifluoroantimony sulfonate were added to the yellow powder under an argon atmosphere, and heating was carried out in diethylene glycol dimethyl ether to obtain the following formula. Luminescent organometallic complex compound MC-1;

The results of 1H-NMR analysis of the luminescent organometallic complex compound MC-1 and the results of LC-MS are shown below. !H-NMR (300 MHz &gt; CDCh): 5 (ppm) = 1.38 (s, 54H) &gt; 6.93 119 323308 201211203 (dd, J = 6.3 Hz and 6. 6 Hz, 3H), 7. 04 (br, 3H), 7 30 (d, J = 7.9 Hz, 3H), 7.48 (d, J = 7.3 Hz, 12H), 7. 61-7. 70 (m, 21H), 7.82 (s, 6H), 8.01 (s, 3H), 8.03 (d, J=7.9Hz, 3H) LC-MS (APCI, positive): m/z+=1677 [Μ+ΗΓ Luminescence of the luminescent organic metal complex compound MC-1 513 nm. &lt;Synthesis Example 12&gt;

(Synthesis of luminescent organometallic complex compound MC-2)

1) n-BuU 2) B(0-W»rj4 3) NaOH aq. &lt;HHaaq. t-Bu (〇H)j L-1

Cl N, Pd(PPh3)4 Na^COs _ Toluene MaO reflux

(wherein t-Bu represents a third butyl group.)

First, 5-bromo-2-phenyl η-pyridine and 4,6-bis(4-t-butylphenyl)-2-chloro-1 were synthesized according to the method described in JP-A-2008-179617. 3, 5-Sanming:. Under a nitrogen stream, 5-bromo-2-phenylidene (8. 10 g'440ramol) and 1320 mL of dehydrated diethyl ether were weighed into a reaction vessel and cooled to -67 °C. Here, a n-butyllithium/hexane solution (15, 3182 mL, 506_〇1) was dropped over 20 minutes. After the completion of the dropwise addition, the resulting solution was stirred at -67 ° C for 1.5 hours. Next, triisopropyl borate (B (〇_i_pr) 3, 95. 2 g, 506 mmol) was added. After stirring for 4 hours, the temperature was slowly raised to room temperature, and 120 323308 201211203 was stirred overnight. 44 mL of IN aqueous sodium hydroxide solution and 500 mL of distilled water were added to the reaction liquid, and the mixture was stirred at room temperature for 30 minutes. The aqueous layer was recovered from the reaction liquid by a liquid separation operation. Approximately 40 mM of 3N hydrochloric acid was added to the aqueous layer of 5 liters to adjust to pH 5, and a jelly-like precipitate was produced. The supernatant was decanted from the reaction solution by decantation. The precipitate was washed twice with distilled water, and then dissolved in methanol to obtain a methanol solution. The supernatant was extracted twice with ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure with the decyl alcohol solution. Ethyl acetate was added to the obtained residue, and the water was removed by azeotropy to obtain a light gray powder of compound L-l (82.9 g). 4,6-bis(4-t-butylphenyl)-2-a-1,3,5-trimorphine (137. lg '361 mmol), compound L1 (82.6 g, 415 mmol), benzene (2890 mL) and hydrazine (triphenylphosphine) palladium (p) (Pd (PPh3) 4, 8.34 g, 7. 22 mmol) were placed in a reaction vessel, and the mixture was stirred at 50 ° C under a nitrogen stream to obtain a solid fraction. Dissolved. A 2 M sodium carbonate aqueous solution (722 mL) was added to the obtained solution, and the mixture was refluxed for 17 hr. The organic layer was recovered from the reaction solution, and washed with a 5% by weight aqueous sodium hydrogencarbonate solution and a 10% by weight aqueous sodium chloride solution. The washed organic layer was dried over sodium sulfate and concentrated. The obtained concentrate was purified by a ruthenium column chromatography of benzene, and the solvent was distilled off. The obtained residue was dissolved in a gas mixture, and ethanol was added to crystallize. After the crystals were separated by filtration, the crystals were washed with ethanol, and dried to give compound L-2 (16.2 g). The results of LC-MS of the compound L-2 and the results of 1H-NMR analysis are shown below. LC-MS (APPI, positive) ra/z · 499 ([M + H]+) lH-NMR (300MHz &gt; CDCh) 121 323308 201211203 (5 (ppm) = 1.42 (s, 18H), 7.52 (m, 3H ), 7.62 (d, J=6. 8Hz, 4H), 7.95 (d, J=8.4Hz, 1H), 8.16 (d, J=7. 3Hz, 2H), 8.69 (d, J=6.8Hz, 4H ), 9.04 (d, J=8.4Hz, 1H), 10.02 (s, 1H)

122 323308 201211203

The compound L-2 (22.17g, 44mmol), silver sulfate trihydrate (6. 95g, 20mmol), 2-ethoxyethanol (96mL) and water (32mL) were weighed into the reaction vessel under argon flow Heat at 140 ° C for 15 hours. After cooling with air, the resulting mixture was subjected to filtration, and the residue was washed with methanol, water and methanol to give a red solid. The red solid was dissolved in chloroform, and ethanol was added to reflux for 2 hours. After cooling with air, the precipitated solid was collected by filtration and washed with ethanol. After repeating this operation three times, the obtained solid was concentrated, and the metal complex complex 1 (20.03 g) was obtained by drying under reduced pressure. A compound 1^-3 (33〇111£, 0.61111111〇1) synthesized by the method described in the pamphlet of International Publication No. 2006/062226, and a di-glyphosate, were obtained by measuring the metal complex complex 1 (759 mg, 0.30 mmol). _(91111〇 into the reaction vessel, adding trifluorosulfonium silver hydride (AgOTf, 157 mg, 0.61 mmol), and stirring at 100 ° C for 10 hours under a stream of argon. After cooling with air, pure water was added to the reaction mixture. (50 mL), the resulting precipitate was separated by filtration, and a mixed solvent (40 mL) of toluene/hexane (1/2 (volume basis)) was added to the precipitate and filtered. The filtrate was dried over sodium sulfate. Purification by gel column chromatography (hexane / benzene = 1 / 1.5 (volume basis)), distilling off the solvent, washing the residue with decyl alcohol, and drying under reduced pressure to obtain a luminescent organic The metal complex compound MC-2 (252 mg, 0.15 mmol). The results of LC-MS of the luminescent organometallic complex compound MC-2 and the results of the ^-NMR analysis are shown below. LC-MS (APCI, Positive) ra/z : 1733 ([M + H]+) !H-NMR (600MHz, THF-ds) 123 323308 201211203 d (ppm) = 1.22 (s, 1 8H), 1.35 (s, 18H), 1.38 (s, 18H), 6. 81 (m, 1H), 6. 82 (m, 1H), 6. 86 (m, 1H), 6. 90 (m, 1H), 6.96 (d, J=7.11Hz, 1H), 7.41 (d, J=7. 1Hz, 1H), 7.22 (d, J=8. 2Hz, 1H), 7.24(d, J=8. 2Hz, 1H), 7.47 (d, J=8. 2Hz, 4H), 7.48 (d, J-8.5Hz, 4H), 7.50 (d, J=8.2Hz, 4H), 7. 66(m, 1H) , 7. 66 (d, J=8. 2Hz, 4H), 7.71 (m, 2H), 7.74 (s, 1H), 7.84 (s, 2H), 7.89 (d, J=7. 9Hz, 1H), 7.93 (d, J=7. 9Hz, 1H), 8.03 (d, J=6.4Hz, 1H), 8.06 (m,1H), # 8.29 (d, J=8. 8Hz, 1H), 8.38 (d, J=8. 5Hz, 4H), 8.41 (d, J=8.8Hz, 1H), 8.43 (d, J=8.2Hz, 4H), 8.67 (s, 1H), 8.99 (d, J=8. 8Hz, 1H), 9.21 (m, 1H), 9.23 (d, J=8. 8Hz, 1H), 9.28 (s, 1H), 9. 44(s, 1H) Luminescence of luminescent organometallic compound MC-2 The spectral peak is 611 nm. &lt;Synthesis Example 13&gt;

(Synthesis of luminescent organometallic complex compound MC-3) • Synthesis of 5-bromo-2-phenyl D-pyridinium

b(oh)2 +

Pd(PPh3)4 Ν32〇〇3 toluene at 20 80 ° C, 6 h, 2, 5-dibromoacridine (7. llg, 30 mmol), toluene (130 mL), phenylboronic acid (4. 57 g, 37. 5mmol) and hydrazine (triphenylphosphine) palladium (〇) (1·73g, 1.5mmol) to the reaction vessel 'under a nitrogen stream, at 5 (TC into 124 323308 201211203 row disturbed 'to dissolve the reactants Next, 'Add 2M aqueous solution of sodium diacetate (30 raL) 'scrambled at 80 ° C for 6 hours. The organic layer of the obtained reaction liquid was recovered by washing with sodium carbonate aqueous solution and saturated saline solution. The layer is dried, and the solvent is distilled off after filtration. The residue is purified by silica gel chromatography (hexane/benzene), and the solvent is distilled off to obtain 5~, odor _2 phenyl hydrazine (6. 21 g). , 26.5mmol). • Synthesis of metal complex complex 2

Measure 5-bromo-2-phenyl bite (7. 39g, 30mm〇i), trihydrate gasification hydrazine (4. 76g, 13.5mmol), 2-ethoxyethanol (58 rainbow) and water ( 19 mL) was heated to a reaction vessel and heated at 14 ° C for 16 hours under a stream of nitrogen. After cooling with air, the resulting reaction mixture was separated and washed with water, methanol and hexane to obtain a metal complex as shown in the above formula as a yellow solid (9. l〇g, 6· 58 mmol). Next, the metal complexes comPlex Κ6·94g, 5. Ommol), 5-bromo-2-phenylpyridine (7. 32g, 30. Ommol) and diglyoxime (43mL) were weighed and trifluoromethyl was added. Silver sulfonate (2.57 g '10.Ommol) was placed in a reaction vessel and stirred at 130 ° C for 14 hours. The resulting reaction product was separated by filtration to dissolve the solid in dichloromethane. The solution was filtered&apos; and the filtrate was concentrated. The precipitated solid was collected by filtration, and washed with hexane to obtain a metal complex complex 2 (6. 35 g ' 7. l mmol) of the above formula. The results of LC-MS and 1H-NMR analysis of the metal complex complex 2 of 125 323308 201211203 are shown below. LC-MS (positive) m/z : 890 ([M + H] + ) 泔fiMR (300MHz, DMS0-d6) 5(ppm)=6.51 (d, J=7. 8Hz, 3H), 6.72 (m, 3H), 6.84 (m, 3H), 7.66 (d, J=2.0Hz, 3H), 7.80 (d, J=7.8Hz, 3H), 8. 05 (dd, J=2.0, 8.8Hz, 3H), 8.14 (d, J=8.8Hz, 3H) • Synthesis of metal complex complex 3

The complex 3 was weighed under a nitrogen stream, and the metal complex complex 2 (3.27 g, 3. 7 mmol), potassium acetate (3.77 g, 33.3 mmol), and bis(pinacol) shed (3.38 g, 13.3 mmol) were weighed. , 1, bis-bis(diphenylphosphino)iron ruthenium (245 mg, 0.44 mmol), [1, fluorene-bis(diphenylphosphino)iron hydrazine] digas palladium (II) (361 mg, 0.44 mmol) And tetrahydrofuran (400 mL) was placed in a reaction vessel and refluxed for 30 hours. The resulting reaction solution was concentrated, and then added to dichloromethane to dissolve and then filtered. The filtrate was purified by silica gel column chromatography (dichloromethane), the solvent was distilled off, and the residue was washed with diethyl ether to obtain a metal misalignment of the above formula 126 323308 201211203 体 complex 3 (2. 55g, 2.47mmol). The results of LC-MS of the metal complex complex 3 and the results of 1 h-NMR analysis are shown below. LC-MS (positive) m/z · 1072 ([M + K] + ) !H NMR (300MHz, CDCh) (5 (ppm)=l. 21 (s, 36H), 6.87 (ra, 9H), 7.69 (d, J=7. 7Hz, 3H), 7.82(s, 3H), 7.86 (m, 6H)

.2, 4-bis(4'-tert-butylphenyl)-6-chloro-1,3,5_three-pound synthesis ci

(wherein t-Bu represents a third butyl group.)

Under a stream of argon, bromo-4-t-butylbenzene (125 g, 587 mmol) and tetrahydrofuran (470 mL) were charged to a reaction vessel and then cooled to dryness. Hey. Next, a n-butyllithium/hexane solution (丨6M, 367 mL, 587 imnol) was dropped at -70 ° C for 90 minutes. After the completion of the dropwise addition, the mixture was stirred at _7 (c) for 2 hours to give a 4-t-butylphenyllithium/tetrahydrofuran solution. Under a stream of argon, a mixture of cyanogen chloride (50.8 g, 276 mmol) and tetrahydrofuran ( 463 mL) was cooled to -7 Torr in another reaction vessel. (: The previously prepared 4-tributylphenyllithium/tetrahydrofuran solution was cooled to a temperature of -601 or less.) After the completion of the dropwise addition, the reaction solution was stirred at -40 ° C for 4 hours and at room temperature for 4 hours. Water was added to the reaction mixture to complete the reaction, and the tetrahydrofuran was distilled off. The resulting residue was 127 323308 201211203 Water and chloroform were added to the slag to extract the organic layer, and the organic layer was washed with water, and the solvent was removed. The residue was dissolved in acetonitrile, and the insoluble solid was filtered off by hot filtration, and the filtrate was concentrated and cooled. After -70 ° C, the precipitated solid was collected by filtration, and the recovered solid was dissolved in a mixed solvent of chloroform / hexane, and purified by silica gel column chromatography (developing solvent: chloroform / hexane). In addition to the solvent, by using the residue Acetonitrile recrystallized to give 2,4-bis (4'-tert-butylphenyl) -6-chloro-1,3,5-farming (41. 3g, 109mmol) square

The results of LC-MS and 2H-NMR analysis of 2,4-bis(4'-t-butylphenyl)-6-gas-1,3,5-trin were shown below.

LC-MS (APPI, positive) m/z: 380 ([M + H] + ) 4 NMR (300MHz, CDC13) 5 (ppm) = l. 39 (s, 18H), 7.56 (d, J=8. 4Hz, 4H), 8. 54 (d, J=8. 4Hz, 4H) • Synthesis of luminescent organometallic complex compound MC-3

(wherein t-Bu represents a third butyl group.) Under a nitrogen stream, the metal complex complex 3 (546 mg, 128 323308 201211203 0·53ππηο 1), 2,4 - 2 (4'_t-butyl group) was weighed. Phenyl)_6_chloro_1,3,5-trimorphine (702 mg, 1.85 mmol), carbonic acid planer (1·73 g, 5.31 mmol), hydrazine (triphenylphosphine) ls (0) (196 mg, 0 17 mmol) and tetrahydro D-propan (53 mL) were placed in a reaction vessel and refluxed for 9 hours. The reaction solution was concentrated, and toluene was added to the concentrated reaction solution to dissolve. This solution was filtered, and the filtrate was purified twice by a silica gel column chromatography (the first solvent to be developed: toluene, the second solvent to be developed: hexamethylene / benzene = 1 / 1 (volume ratio)). The luminescent organic metal complex compound MC-3 (257 mg, 0.15 mmol) represented by the above formula was obtained by washing the residual oil with decyl alcohol. The results of LC-MS of the luminescent organometallic complex compound MC-3 and the results of the ^-NMR analysis are shown below. LC-MS (APCI, positive) m/z · 1686 ([M + H] + )

4 NMR (300MHz, CDCM (5 (ppm) = 1.4 (s, 54H), 6. 96 (m, 9H), 7.39 (d, J-8. 4Hz, 12H), 7.83 (d, J=7 5Hz, 3H), 8.18 (d, J=8.4Hz, 3H), 8.36 (d, J=8. 4Hz, 12H), 9.14 (d, J=8.4Hz, 3H), 9.33 • (s, 3H) &lt;Synthesis Example 14&gt; (Synthesis of luminescent organometallic conjugate compound MC-4) The following formula:

The luminescent organometallic complex compound MC-4 shown in MC-4 129 323308 201211203 was synthesized in accordance with the method described in International Publication No. 2002/44189. &lt;Synthesis Example 15 &gt; Synthesis of luminescent organometallic conjugate compound MC-5; Synthesis of metal complex complex 4

The luminescent organometallic complex compound Μ(&gt;1 (4. 25g '2.5 mmol) and gas imitation (4 〇〇mL) were weighed into a reaction vessel under an argon flow to make the luminescent organometallic complex The compound MC-1 was dissolved. Next, N_glysinimide (872 mg, 4.9 imnol) was added and stirred at room temperature for 24 hours. Distillation • After the solvent was removed, a mixed solvent of chloroform/hexane was added to the residue. (l〇〇mL) was dissolved. The obtained solution was purified by gel column chromatography (developing solvent: chloroform/hexane-mixed solvent), and the precipitated solution was recovered, and the solvent was removed, and then washed by decyl alcohol. The metal residue represented by the above formula complex 4 (3.0 mmol) was obtained as a net residue.

The results of the MALDI-T0FMS of the metal complex Complex 4 and the results of the 1H-NMR analysis are shown below. MALDI-TOFMS (positive, [Measurement Method 1]) m/z: 1890 130 323308 201211203 ([Μ]) *Η NMR (300MHz, THF-ds) 5(ppm)=1.27 (s, 18Η), 1.36 (s , 18H), 1.41 (s, 18H), 6.95 (m, 4H), 7.24 (m, 2H), 7.48 (m, 12H), 7.69 (ra, 5H), 7. 74(m, 3H), 7. 83 (s, 2H), 7. 99 Cd, J=6. 0Hz, 1H), 8.09(m, 3H), 8. 40 (m, 9H), 8. 54 (d, J=8. 6Hz, 1H ), 8.68 (s, 1H), 9.05 (m, 1H), 9.22 (m, 2H), 9.28 (d, J=8. 6Hz, 1H), 9.46 (s, 1H)

• Synthesis of luminescent organometallic complex compound MC-5

The metal complex c〇roplex4 (2.84 g, Lu 1·5 mmol), the compound L-5 (1.56 g, 3.3 mmol), and 20% by weight of tetraethylammonium hydroxide (Tetraethylammonium Hydroxide) were weighed under a stream of argon. An aqueous solution (5.22 g 7.4 mmol), hydrazine (triphenylphosphine) palladium (ruthenium) (6 l mg, 〇. 5 mmol) and tetrahydrofuran (90 mL) were placed in a reaction vessel and refluxed for 14 hours. To the reaction liquid, benzene and water were added to wash, and the organic layer was recovered. The organic layer was washed with brine and dried over sodium sulfate. The resulting solution was filtered and concentrated. The resulting concentrate was refined by gel column chromatography (developing solvent: methyl stupid). The precipitated solution was recovered. After the solvent was distilled off, a mixed solvent of propylene/131 323308 201211203 hexane was added to the residue to dissolve. The obtained solvent was subjected to column chromatography (expansion, medium: gas imitation/fantasy was difficult, and the solvent was removed. The residue was dissolved in toluene', and acetonitrile was added to the solution to be purified by crystallization. The obtained isomer was separated and recovered to obtain the luminescent organometallic complex compound MC-5 (2.85 g, 1.2 mm 〇l) of the above formula. Further, the compound L-5 was in accordance with WO 02/66552. Method Synthesis The results of MALDI-T0FMS of metal-missing MC-5 and the results of 1h-nm analysis are shown below. MALDI-TOFMS (positive, [Measurement Method 1]) m/z : 2413 ([M]) !H NMR (300MHz, THF-ds) 5(ppm) = 1.26 (s,18H), 1.37(s,18H), 1.38 (s,18H), 1.40 (s, 18H), 1.42 (s, 18H), 7.26 (d, J=8. 1Hz, 1H), 7, 31(d, J=8. 1Hz, 1H), 7. 33 (d, J=8. 1Hz, 2H), 7.35 (d, J=8 1Hz, 1H), 7. 39 (d, J=8. 1Hz, 1H), 7. 48 (d, J=8. 4Hz, 4H), 7.49 (d, J=8.3Hz, 4H), 7.50 ( d, J=8. 1Hz, 4H), 7. 51(d, J=8. 1Hz, 4H), 7.52 (d, J=8. 5Hz, 4H), 7.68 (d, J=8. 4Hz, 4H ), 7. 69 (d, J=8. 5Hz, 4H), 7.72 (d, J=8. 3Hz, 4H), 7.74 (m, 4H), 7.75 (s, 1H), 7.78 (s, 1H) , 7.88 (s, 2H), 7. 91(s, 2H), 7. 92(s, 2H), 8. l〇(m,iH), 8. 11 (d, J=6. 2Hz, 1H), 8.35 (s, 1H), 8.39 (m, 5H), 8.44 (d, J=8. 1Hz, 4H), 8. 56 (d, J=8. 8Hz, 1H), 8.69 (d, J=8. 8Hz, 1H), 8. 73(s, 1H), 9. 03 (d, J=8. 8Hz, 1H), 9. 26 (m, 1H), 9.27 (d, J=8.8Hz, 1H), 9.38 (s, 1H), 9. 5i (s, in) 132 323308 201211203 &lt;Cave transporting south molecular compound HP-1 &gt; The hole-passing polymer compound HP-1 is modulated in the following order . Mixing compound M_8 (17.3 g, compound 4g), 9' 9-dioctyl-2,7-dibromoindole (2.62 g), 9, 9-bis (benzocyclobutane) under an inert atmosphere After 4-en-4-yl)-2,7-dibromoindole (1.51 g) and toluene (580 mL), the mixture was stirred while heating. Palladium acetate (4.30 mg) and ginseng (2-methoxyphenyl)phosphine (27. Omg) were added thereto, and after heating to i〇〇°c, 2% by weight of tetraethylammonium hydroxide was added. After the aqueous solution (10).5 g) was dropped, the mixture was heated to reflux for 7 hours. Next, phenylboric acid (230 g), bis(triphenylphosphine)palladium dichloride (13.41 Å), and 20% by weight aqueous tetraethylammonium hydroxide solution (68.5 §) were added, and the mixture was heated under reflux overnight. After removing the aqueous layer from the reaction solution, sodium N,N-diethyldithiocarbamate φ trihydrate (10 g) and ion-exchanged water (12 mL) were added. After stirring for 4 hours at 4 (TC), the organic layer and the aqueous layer were separated in the reaction solution, followed by ion exchange of water once, 10% by weight of hydrochloric acid twice, and 3% by weight of aqueous ammonia solution twice. The organic layer was washed twice with ion-exchanged water. The obtained organic layer was passed through a column packed with tantalum and alumina in the presence of toluene, and the passed solution was dropped to decyl alcohol to precipitate a precipitate. The precipitate was collected by filtration and dried, and 19.5 g of a polymer compound (hereinafter referred to as "polymer compound HP-1") was mentioned. Polymer 133 323308 201211203 Polymer compound number-average molecular weight (??) And the weight average molecular weight (Mw) is Μη=7·5x10, and Mw=3. 6xl05. From the loading ratio of the raw material monomers, the polymer compound HP-1 is presumed to have the following constituent units and moir Ratio, and the constituent unit of (PA) is selected from (PB) A polymerization unit of another polymer compound.

&lt;Polar-transporting polymer compound HP-2&gt; The hole-transporting polymer compound HP-2 was prepared in the following order. Mixing compound M-8 (0.993 g), hydrazine, Ν'-bis(4-bromophenyl)-indole, Ν'-bis(2,6-dimethyl-4-n-butyl) under an inert atmosphere Phenyl phenyl)-1,4-# phenylenediamine (1.923 g), 9,9-dioctyl-2,7-dibromo g (0.5947 g), 9, 9-bis (benzocyclobutane) After 4-enyl)-2,7-dibromoindole (0.337 g) and toluene (118 mL), the mixture was stirred while heating. Palladium acetate (1.0 mg) and ginseng (2-methoxyphenyl)phosphine (6.1 mg) were added to the reaction mixture, and after heating to 100 ° C, 20% by weight aqueous solution of tetraethylammonium hydroxide ( 15. 3g) Drip and reflux while heating for 11 hours. Next, phenylboric acid (〇.〇53g), acetic acid (1.0 mg), ginseng (2-decyloxyphenyl)phosphine (6.1 mg) and 20% by weight of hydrogen oxide 134 were added to the reaction mixture. 323308 201211203 A solution of tetraethylammonium chloride (15.3 g) was refluxed while heating overnight. After removing the aqueous layer from the reaction mixture, sodium N,N-diethyldithioacetate trihydrate (2.41 g) and ion-exchanged water (48 mL) were added, and the mixture was stirred at 85 ° C for 2 hours. After the organic layer of the reaction mixture was separated from the aqueous layer, the organic layer was washed in the order of ion exchange water twice, 3% by weight aqueous acetic acid solution twice, and ion-exchanged water twice.

The obtained organic layer was dropped into methanol, and the resulting precipitate was collected by filtration and dried to give a solid. This solid was dissolved in toluene, and the toluene solution was passed through a column packed with tantalum/alumina in advance through the flow of benzene. The precipitate after the flow was dropped into decyl alcohol, and the resulting precipitate was collected by filtration and dried to obtain 3.71 g of a hole transporting polymer compound HP-2. 5xl05。 Mx=l. 5xl05. The Mn=5. 6xl04, Mw=l. 5xl05. From the monomer loading ratio, the hole transporting polymer compound HP-2 is estimated to have the following structural unit and molar ratio, and the constituent unit of (PA) and the constituent unit selected from (PB) A polymer compound that is polymerized with each other.

(wherein Me represents a fluorenyl group, and n-Bu represents an n-butyl group.) 135 323308 201211203 [Example 1] &lt;Synthesis of South Molecular Compound A&gt; In a noble gas atmosphere, compound M-1 (2, 5-bis(4,4,5,5-tetramethyl-1,3,2-dioxa-heterocyclopentyl-2-yl)-1,4-dihexylbenzene) (1· 451 g), Compound M-2 (2,6-bis(4,4,5,5-tetradecyl-1,3,2-dioxaborolan-2-yl)-toluene) (〇.424g) , compound M-3 (9,9-bis(4-n-hexylphenyl)-2,7-di-dioxamidine) (2.22 g), compound (2, 4-bis(4-bromophenyl)-6 -(4-n-Dodecylphenyl)-1,3, 5-Sanming:) (0. 523g) and toluene (59mL) 'When one side is heated, it is dropped. Palladium acetate (1.4 mg) and ginseng (2-decyloxyphenyl)phosphine (8.7 mg) were added, and 20% by weight of a rat aqueous solution of tetraethylammonium hydroxide (14·7 g) was added dropwise and heated under reflux for 17 hours. Next, phenyl decadate (〇. 〇 51g), acetic acid | bar (1.4 mg), ginseng (2-decyloxy) phosphine (8.7 mg) and 20% by weight of aqueous tetraethylammonium hydroxide solution were added. (14. 7g) 'The heating is refluxed for π hours. After removing the aqueous layer, sodium diethyldithiocarbamate trihydrate (2.28 g) and ion-exchanged water (46 mL) were added at 85. (The mixture was stirred for 2 hours. After the organic layer was separated from the aqueous layer, the organic layer was washed twice with ion-exchanged water, 3% by weight of B-series water, 2 times of gluten solution, and 2 times of ion-exchanged water. The organic layer was dropped into methanol, and the resulting precipitate was collected by filtration, and dried to give a solid. The solid was dissolved in toluene, and the toluene solution was again passed through a tube filled with benzene and oxidized in advance. In the column, the precipitate after the flow was dropped into the f-alcohol, and the resulting precipitate was collected by filtration. The polymer compound (hereinafter referred to as "polymer compound Ap") was 2.43 g. The height was determined according to the analysis condition 2. The amount of polystyrene converted to the molecular compound a is 323308 136 201211203 The average molecular weight and the weight average molecular weight are respectively Mn=8.6xlQ4, Χίο5. From the monomer loading ratio, the polymer compound lanthanide is presumed to have the following The single unit 70 and the molar ratio are repeated, and the repeating unit of (ΡΑ) and the repeating unit selected from (ΡΒ) are mutually polymerized polymer compounds.

CftH13

= 35/15

Ch3 xy

&lt;Production and Evaluation of Organic EL Element&gt; On a glass substrate with an IT tantalum film of thickness milk (10) obtained by sputtering method, 'glycolized ethylene glycol monobutyl ether/water ( 3/2 (volume ratio) solution (Sigma-Aldrich, trade name: ρΐεχ_ 〇c 12〇〇)

2 Rotate (4), the material thickness is 65 nm, and dry on a hot plate for 15 minutes. The hole penetrates the polymer compound (4) with a U weight of 20nffl ° molecular compound two weights, and the concentration dissolves to a high ratio to become a heart. ~,; property = liquid borrowing = 323308 137 201211203 Composition 1 was spin coated, and film was formed at a rotational speed of 1800 rpm. The thickness of the film is approximately 80 nm. The film was dried in i3 ° C for 10 minutes under a nitrogen atmosphere, and then sodium fluoride was used as a cathode to be about 3 nm, and then aluminum was vapor-deposited to about 80 nm to prepare an organic EL device. Further, after the degree of vacuum reached ixi 〇 4 Pa or less, vapor deposition of the metal was started. After applying a voltage to the obtained organic EL device, electroluminescence luminescence (hereinafter referred to as EL luminescence) having a peak at 520 nm of the self-luminous organometallic conjugate compound MC-1 can be obtained from the device. The light-emitting efficiency is 60.88 cd/A. The light-emitting efficiency is 60.88 cd/A. The current value was set such that the initial luminance of the organic EL device obtained above was 8000 cd/m2, and then driven at a constant current to measure the temporal change in luminance. As a result, the degree of attenuation was reduced to 80% of the initial brightness after 72.1 hours, and was attenuated to 7〇0/0 of the initial brightness after 235 hours. [Example 2] ^ &lt;Synthesis of Polymer Compound B&gt; The compound M-1 (2, 5-bis(4, 4, 5, 5-tetradecyl-1, 3) was mixed under an inert gas atmosphere. 2-Dioxaborolan-2-yl)-1,4-dihexylbenzene (8. 182 g), compound M-3 (9,9-bis(4-n-hexylphenyl)-2 , 7-Dibromofluorene) (8.508), compound||-4 (2,4-bis(4-bromophenyl)-6-(4-n-dodecylphenyl)-1,3,5 - Three tillages (2. 〇 97 g) and toluene (250 mL) were stirred while heating. Palladium acetate (3.7 mg) and ginseng (2-methoxyphenyl)phosphine (23.2 mg) were added to heat to 1 Torr. To the resulting solution, a 20% by weight aqueous solution of tetraethylammonium hydroxide (61.3 g) was added dropwise to reflux at 8 hours 138 323308 201211203. Next, phenylboric acid (0.20 g), palladium acetate (3.7 mg), ginseng (2~methoxyphenyl)phosphine (23.3 mg), and 20% by weight aqueous solution of tetraethylammonium hydroxide (58.3 g) were added. The mixture was heated to reflux for 15 hours. After removing the aqueous layer, sodium N,N-diethyldithiocarbamate trihydrate (9.11 g) and ion-exchanged water (60 mL) were added and stirred at 40 ° C for 3 hours. After the organic layer was separated from the aqueous layer, the organic layer was washed in the order of ion-exchanged water once, 1% by weight of hydrochloric acid twice, 3% by weight of aqueous ammonia solution twice, and ion-exchanged water 2 times. The organic layer was passed through a column filled with sand and oxidized ruthenium in the form of a solution, and the passed solution was dropped into methanol to precipitate a precipitate. The precipitate was taken and dried to obtain 9.80 g of a polymer compound (hereinafter referred to as "polymer compound B"). The polymer compound B has a polystyrene-equivalent number average molecular weight and a weight average molecular weight measured by the analysis condition i, and is Mn = 9. 2xl04, Mw = 2. 3xl05.

From the monomer loading ratio, the polymer compound B is presumed to have the following repeating unit and molar ratio, and the repeating unit of (PA) and the repeating unit selected from (PB) are mutually polymerized. Compound. (PA)

=50

323308 139 201211203 &lt;Production and Evaluation of Organic EL Element&gt; In addition to a solution in which the polymer compound 8 is dissolved in a diphenylbenzene solvent at a concentration of 1.9 wt% and a luminescent organic metal at a concentration of 19 wt% The solution in which the compound of the compound MC-1 was dissolved in the diphenylbenzene solvent was mixed in such a manner that the weight ratio was 70:30, and the composition 2 was prepared in place of the first product of the first embodiment, in the same manner as in the example j. The organic EL device was produced. After the voltage is applied to the obtained organic EL element, the luminescent organic metal complex compound MC_ can be obtained from the element; [the EL luminescence having a peak at 52〇11111] The element emits light from 2.9V, and displays 1000 cd at 5.8V. The luminous efficiency of /m2 'maximum luminous efficiency is 55.4 cd/A. The current value was set such that the initial luminance of the organic EL device obtained above was 8000 cd/m2, and then driven at a constant current to measure the temporal change in luminance. As a result, the luminance was attenuated to 80% of the initial luminance after 101.6 hours, and was attenuated to 70% of the initial luminance after 252.5 hours. [Example 3] &lt;Synthesis of Polymer Compound C&gt; The compound bis(4,4,5,5-tetramethyl~1,3,2-dioxabenzene heterocyclic pentylene was mixed under an inert gas atmosphere. —2-yl)-1,4-dihexylbenzene) (1. 688g), compound m-2 (2,6-bis(4, 4, 5, 5-tetradecyl-1,3, 2-di Oxaborocyclohexan-2-yl)-toluene) (〇. 497g), compound M-3 (9,9-bis(4-n-hexylphenyl)-2,7-dibromofluorene) (2 484g), compound M-5 (2,4-bis(4-phenylene)-6-(4-n-hexylphenyl)_1,3, 5-trin) (〇.531g) and toluene ( 66mL), stir on one side while heating. Ethylene 140 323308 201211203 palladium (1.7 mg) and ginseng (2-methoxyphenyl) phosphine (1 〇 2 mg) were added, and a 2% by weight aqueous solution of tetraethylammonium hydroxide (17.2 g) was added dropwise to reflux. 7 hours. Next, phenylboric acid (〇·〇59g), palladium acetate (1.7 mg), ginseng (2-methoxyphenyl)phosphine (10.3 mg) and 20% by weight of tetraethylammonium hydroxide aqueous solution were added ( 17. lg) 'Ther is heated to reflux for 15 hours. After removing the aqueous layer from the reaction mixture, sodium N,N-diethyldithiocarbamate dihydrate (2.68 g) and ion-exchanged water (54 mL) were added and the mixture was stirred at 85 ° C for 2 hours. After the organic layer of the reaction mixture was separated from the aqueous layer, the organic layer was washed twice with ion exchange water twice, 3% by weight aqueous acetic acid solution twice, and ion-exchanged water twice. The organic layer was dropped into methanol and the resulting precipitate was filtered, and dried to give a solid. This solid was dissolved in toluene, and the toluene solution was again passed through a column packed with tantalum/alumina in advance through toluene. The precipitate after the flow was dropped into decyl alcohol, and the resulting precipitate was collected by filtration and dried to obtain 2 81 g of a high molecular compound (hereinafter referred to as "polymer compound c"). The polystyrene-equivalent amount average molecular weight and weight average molecular weight measured by the condition 2 of the polymer φ compound C were Μη = 8. 1χ1〇4, Mw=2 8x 105, respectively. &lt;Production and Evaluation of Organic EL Element&gt; In addition to a solution in which the polymer compound c was dissolved in a xylene solvent at a concentration of 1.9 wt% and a luminescent organic metal complex at a concentration of 9% by weight The solution in which the compound MC-1 was dissolved in a xylene solvent was mixed so that the weight ratio was 70:30, and the composition 3 was prepared in place of the composition 1 of Example 1, and the same procedure as in Example , was carried out to prepare 323308. 141 201211203 Organic EL components. After applying a voltage to the obtained organic EL device, EL light having a peak at 520 nm of the self-luminous organometallic compound compound MC-1 can be obtained from the device. 8 cd/A. The maximum luminous efficiency is 61.0 cd/A. The current value was set such that the initial luminance of the organic EL device obtained above was 8000 cd/m2, and then driven at a constant current to measure the temporal change in luminance. As a result, the luminance was attenuated to #80% of the initial luminance after 44.4 hours, and was attenuated to 70% of the initial luminance after 156.5 hours. From the monomer loading ratio, the polymer compound C is presumed to have the following repeating unit and molar ratio, and the repeating unit of (PA) and the repeating unit selected from (PB) are mutually polymerized. Compound.

C5h13 = 35/15 = 40/10 [Example 4] &lt;Synthesis of Polymer Compound D&gt; Compound M-1 (2, 5-bis(4, 4, 5, 5-) was mixed under an inert gas atmosphere Tetradecyl-1,3,2-dioxapentan-2-yl)-1,4-dihexylbenzene (2.807 g), compound M-3 (9,9-bis(4-) n-Hexylphenyl)-2,7-dibromofluorene) (2. 903 g), compound M-5 (2,4-bis(4-bromophenyl)-6-(4-n-hexane 142 323308 201211203 phenyl) )-1,3,5-three tillage) (〇. 621g) and toluene (85mL), while heating ~ surface for mixing. Palladium acetate (1.9 mg) and ginseng (2-oxalyloxy) sulphonium l*9 mg) were added to drip 2 〇 by weight. An aqueous solution of /q tetraethylammonium hydroxide (19·9 g) was heated under reflux for 5 hours. 5小时。 Next, phenylboric acid (〇. 〇 69g), palladium acetate (1.9 mg) and ginseng (2 methoxy phenyl) phosphine (11.9 mg), and heated to reflux for 15. 5 hours. After removing the aqueous layer from the reaction solution, N,N-diethyldithioamine phthalate is added.

Dihydrate (3.13 g) and ion-exchanged water (63 mL) were stirred at 85 ° C for 2 hours. After the organic layer of the reaction mixture was separated from the aqueous layer, the organic layer was washed twice with ion-exchanged water, twice with a 3% by weight aqueous acetic acid solution, and ion-exchanged water 2 3 . The organic layer was dropped into methanol and the resulting precipitate was collected by filtration, and dried to give a solid. This 1H (tetra) was dissolved in f benzene. The toluene solution was passed through a column packed with (4) gum/oxidized|s pre-circulated toluene. The precipitate after the flow was dropped into methanol, and the resulting sink was taken and dried to obtain a high-part compound (hereinafter referred to as "polymer compound D") 3 52 g. The number of molecular weights and the weight average molecular weight in terms of polyphenylene (10) measured by the analysis condition 1 of the polymerized human D were respectively _.5&gt;&lt;1()5, .=4.7_5. From the monomer loading ratio, the polymer compound D is presumed to have the following weight, early π and molar ratio, and the repeating unit of (PA) and the repeating single τ selected from (PB). A polymer compound that is polymerized with each other. 323308 143 =50201211203

= 40/10 &lt;Production and Evaluation of Organic EL Element&gt; In addition to a solution in which the polymer compound D was dissolved in a xylene solvent at a concentration of 1.5% by weight and a luminescent organic metal at a concentration of 1.5% by weight The solution in which the compound of the compound MC-1 was dissolved in the xylene solvent was mixed in such a manner that the weight ratio was 70:30, and the composition 4 was prepared in the same manner as in Example 1 except that the composition 1 of Example 1 was prepared. An organic EL element is produced. After applying a voltage to the obtained organic EL device, EL light having a peak at 520 nm of the self-luminous organometallic compound compound MC-1 can be obtained from the device. The device started to emit light at 2. 9 V, and showed a luminescence of 1000 cd/m 2 # at 6.0 V, and the maximum luminous efficiency was 56.48 cd/A. The current value was set such that the initial luminance of the organic EL device obtained above was 8000 cd/m2, and then driven at a constant current to measure the temporal change in luminance. As a result, the luminance was attenuated to 80% of the initial luminance after 19.6 hours, and was attenuated to 70% of the initial luminance after 75.5 hours. [Comparative Example 1] &lt;Synthesis of Polymer Compound E&gt; Compound M-1 (2, 5-bis(4, 4, 5, 5-144 323308 201211203 tetradecyl-1) was mixed under an inert gas atmosphere. 3,2-Dioxaborolan-2-yl)-1,4-dihexylbenzene (3.12 g), 9,9-dioctyl-2,7-dibromofluorene (2. 770 g), compound M-5 (2,4-bis(4-bromophenyl)-6-(4-n-hexylphenyl)-1,3,5-trimium) (0. 696 g) and toluene (82 mL) ), while heating, while disturbing. Palladium acetate (2.1 mg) and bis(2-methoxyphenyl)phosphine (13.4 mg) were added, and a 20% by weight aqueous solution of tetraethylammonium hydroxide (22.3 g) was added dropwise, and the mixture was heated under reflux for 5 hours. Next, 'p-phenylboric acid (0. 〇78g), palladium acetate (2.1 mg), ginseng (2-methoxyphenyl)phosphine (13.3 mg) and 20% by weight of tetraethylammonium hydroxide solution were added. (22_ 3g). Allow to heat to reflux Π. 5 hours. After removing the aqueous layer from the reaction mixture, sodium N,N-diethyldithiocarbamate trihydrate (3.41 g) and ion-exchanged water (7 mL) were added, followed by stirring at 85 ° C for 2 hours. After the organic layer of the reaction mixture was separated from the aqueous layer, the organic layer was washed three times with ion-exchanged water, three times by weight of an aqueous acetic acid solution, and three times of ion-exchanged water. The organic layer was dropped into methanol and the resulting precipitate was filtered off, and after drying, φ gave a solid. The solid was dissolved in toluene, and the toluene solution was again circulated in a column filled with a pre-circulated sputum; The precipitate after the flow was dropped into decyl alcohol, and the resulting precipitate was collected by filtration and dried to obtain 3.43 g of a polymer compound (hereinafter referred to as "polymer compound E"). The number average molecular weight and the weight average molecular weight of the polymer compound E according to the analysis condition 2 are Μη=16χ1〇5, Mw=5 2 xlO5 〇 from the monomer loading ratio, the polymer The compound lanthanide is presumed to have the following repeating unit and molar ratio, and the repeating unit of (ΡΑ) and the repeating unit selected from 323308 145 201211203 (PB) are mutually polymerized polymer compounds.

PeHi3

(PA) = 50

CeH13

(PB) C$H17 CgHt?

NVN T = 40/10 Φ &lt;Production and Evaluation of Organic EL Element&gt; φ In addition to a solution in which the polymer compound E was dissolved in a xylene solvent at a concentration of 1.6% by weight and a concentration of 1.6 wt/min The solution in which the luminescent organometallic complex compound MC-1 was dissolved in a xylene solvent was mixed so that the weight ratio was 70:30, and the composition 5 was prepared instead of the composition 1 of Example 1, and Example 1 was used. The organic EL device was produced in the same manner. After applying a voltage to the obtained organic EL device, the EL light having the peak # at 520 nm of the self-luminous organometallic compound compound MC-1 can be obtained from the device. The device emits light from 3.0 V, and exhibits a light emission of 1000 cd/m 2 at 6.7 V, and the maximum luminous efficiency is 47.54 cd/A. The current value was set such that the initial luminance of the organic EL device obtained above was 8000 cd/m2, and then driven at a constant current to measure the temporal change in luminance. As a result, the luminance was attenuated to 80% of the initial luminance after 11.3 hours, and was attenuated to 70% of the initial luminance after 28.9 hours. [Example 5] &lt;Synthesis of Polymer Compound F&gt; 146 323308 201211203 9,9-bis(4-n-hexylphenyl)-2,7-bis(4 4 R c ' was mixed under an inert gas atmosphere. ',5~tetradecyl-1,3,2-dioxaborolan-2-yl)-indole_, 9,9-dioctyl-2,7-bis (4, 4, 5 , 5-tetramethyl-1,3,2-dioxazacyclopentan-2-yl)-(0.9422), 9,9-bis(3-n-hexyl)- 2,dibromo (2. 194g), compound M-4 (2,4-bis(4-bromophenyl 'n-dodecylphenyl)-1,3, 5-triphthyl) (〇·666g), N, N,- (4- &gt; stinyl phenyl)-N, ν' - bis (2, 6-dimercapto-4-tert-butylphenyl) This month (女.580g) and Aben ( 114mL) ' Stir while heating. Add bis(triphenylphosphine)palladium dichloride (3.7 mg) to 10 (TC, / 20% by weight aqueous tetraethylammonium hydroxide solution (18.5 g), and heat to reflux for 8 hours. Add a solution of stearylboronic acid (〇.〇65g), ditriphenylphosphine dichloride (3.7mg) and 20% by weight of aqueous tetraethylammonium hydroxide solution (18 5g), and heat to reflux overnight. After the aqueous layer was added, N,N-diethyldithiocarbamate sodium trihydrate (2·91 §) and ion-exchanged water (58 mL) were added, and the mixture was stirred at 85 ° for 2 hours. After separating from the aqueous layer, the organic layer was washed twice with ion-exchanged water, twice with 3% by weight aqueous acetic acid solution, and twice with ion-exchanged water. The organic layer was dropped into methanol and filtered. After precipitation, after drying, a solid is obtained. The solid is dissolved in toluene, and the toluene solution is again circulated to a column packed with tantalum/alumina in advance through the flow of benzene. The precipitate after circulation is dropped into methanol and The resulting precipitate was collected by filtration and dried to obtain a polymer compound (hereinafter referred to as "polymer compound F") 4 28 g Polymer 147 323308 201211203 Compound F According to the analysis condition 2, the polystyrene exchange average molecular weight and the weight average molecular weight were respectively Mn=9. Π)5 〇Right from the ratio of 'polymer compound system is presumed The repeating unit of the heavy freshener (10) of (10) is a polymer compound which is polymerized with each other.

^Ηι/ί:βΗ17 (ΡΑ) C€H13

36/14

C12H2S 32.5 / 1〇/ 7.5 (wherein Me represents a methyl group, and Bu represents a third butyl group; production and evaluation of an organic EL element> In the embodiment 1, except for a hole transporting polymer compound liver _2 Spin coating in a state of = 7 by weight of (tetra) xylene solution, forming a film of thickness &1 &quot; bis and a polymer compound F at a concentration of U% by weight: solution of the solution in the solvent and 16 weight The mixture of the luminescent organometallic complex compound M (&gt;2 in a diterpene benzene solvent is mixed in a weight ratio of 92.5:5, and is prepared to form a composition = In place of the composition 丨, and the 6 成 成 藉 155 155 155 155 155 155 155 155 155 155 155 155 155 155 155 155 155 155 155 155 155 155 155 膜 膜 膜 膜 膜 膜 膜 膜 膜 膜 膜 膜 膜 膜 膜 155 155 155 155 The EL element is self-sufficient: after the voltage is applied to the 21-element EL element, the EL luminescence from the luminescent luminescent metal-mismatched conjugate (4) to 615 nm having the peak 323308 148 201211203 can be obtained from the element. The element emits light from 2.3 V. At 4.7 V, the luminescence of 1000 cd/m2 was shown to have a maximum luminous efficiency of 21.15 cd/A. When the initial luminance of the organic EL device obtained above was set to a current value of 8000 cd/m 2 , the current was driven at a constant current, and the temporal change in luminance was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 525 hours. 1244. After 4 hours, it was attenuated to 70% of the initial brightness. [Example 6] &lt;Synthesis of Molecular Compound G&gt; 9,9-bis(4-n-hexylphenyl)-2 was mixed under an inert gas atmosphere. , 7-bis(4' 4, 5, 5~tetradecyl-1,3,2-dioxaborolan-2-yl)-苐^〇21g), 9 9_dioctyl _ 2 7_Bis(4,4,5,5_tetradecyl_13,2_oxazacyclopentan-2-yl)-indole (0.691), 9,9-bis(3-n-hexyl) Styrene)-2,7-dibromoindole (i.6〇8g), compound M-5(2,4-bis(4-bromophenyl)-6-(4-n-hexylphenyl)_1,3 , 5-three tillage) (0.423§), 1^-double (4~ desert base) _NN,-bis (2,6-didecyl_4_t-butylphenyl)_14_ Φ stupid diamine 0. 425g) and toluene (82mL), while stirring, while heating, adding bis(triphenylphosphine)palladium (2.7 mg), and adding 20% by weight aqueous solution of tetraethylammonium aroxide (13.7 g) ) The mixture was heated to reflux for 7 hours. Next, stearylboronic acid (〇·〇 47 g), bis(triphenylphosphine)palladium dichloride (1.4 mg) and 20% by weight aqueous tetraethylammonium hydroxide solution (a) were added. 6g), heated to reflux for 16 · 5 hours. After removing the aqueous layer from the reaction mixture, sodium N,N-diethyldithiocarbamate dihydrate (1.81 g) and ion-exchanged water (36 mL) were added, followed by stirring at 8 yc for 2 hours. After the organic layer of the reaction mixture was separated from the aqueous layer, the organic layer was washed twice with ion 149 323308 201211203, twice with 3% by weight aqueous acetic acid solution, and twice with ion-exchanged water.

The organic layer was dropped into methanol and the resulting precipitate was filtered, and dried to give a solid. This solid was dissolved in toluene, and the toluene solution was again passed through a column packed with tantalum/alumina in advance through toluene. The precipitate after the flow was dropped into methanol, and the resulting precipitate was collected by filtration and dried to obtain a polymer compound (hereinafter referred to as "polymer compound G") 3. 〇 4 g. The mass average molecular weight and the weight average molecular weight of the polystyrene-equivalents were determined to be Mn = 9. lxl 〇 4, Mw = 2. 5xl05. From the monomer loading ratio, the polymer compound G is presumed to have the following repeating unit and molar ratio, and the repeating unit of (PA) and the repeating unit selected from (PB) are mutually polymerized. Compound.

(In the formula, "Me" represents a decyl group, and t-Bu represents a third butyl group.) &lt;Production and Evaluation of Organic EL Element&gt; In addition to a solution in which a polymer compound F is dissolved at a concentration of 1.5% by weight The solution of the luminescent organometallic compound compound MC-2 dissolved in the diterpene solvent was mixed at a weight ratio of 92.5:7.5, and the composition 7 was prepared in place of the example 5 at a concentration of 1.5% by weight. An organic EL device was produced in the same manner as in Example 5 except for the composition 6. 150 323308 201211203 After applying a voltage to the obtained organic EL device, EL light having a peak at 615 nm of the self-luminous organometallic compound compound MC-2 can be obtained from the device. The element started to emit light from 2., and the light emission of i〇〇〇cd/m2 was displayed at 5. 〇v, and the maximum luminous efficiency was 16.93 cd/A. After setting the current value so that the initial luminance of the organic EL device obtained above was 8000 cd/m 2 , the driving was performed at a constant current, and the time change of the luminance was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 105 hours. Attenuated to 70% of the initial brightness after 408 hours. [Comparative Example 2] &lt;Synthesis of molecular compound hydrazine&gt; 9,9-dioctyl-2,7-bis(1,3,2-dioxaborolane was mixed under an inert gas atmosphere -2-yl)-oxime (2.652g), 9,9-dioctyl-2,7-di-filler (1.920g), 2,4-bis(4-bromophenyl)-6-(4- n-Hexylphenyl) -1,3,5-trimium (〇. 531g), N,N,-bis(4-bromophenyl)-N,N,-bis(2,6-dimercapto-4 -T-butylphenyl)-1 4-phenylenediamine (〇.369g), gasified methyl-octyl money (trade name: A1 iquat336, manufactured by Aldrich) (〇. 65g) and toluene (50mL) Stir while heating. Bis(triphenylphosphine) dichloride (3.5 mg) was added, and a 17.5% by weight aqueous sodium carbonate solution (13.5 mL) was added dropwise to reflux for 3 hours. Next, phenylboric acid (〇. 61〇g), bis(triphenylphosphine)palladium dichloride (3.5 mg), and toluene (50 mL) were added, and the mixture was heated under reflux for μ hours. After the aqueous layer was removed from the reaction mixture, sodium N,N-diethyldithiocarbamate (3.04 g) and ion-exchanged water (3 mL) were added, followed by stirring at 85 ° C for 2 hours. After the organic layer of the reaction mixture was separated from the aqueous layer, the organic layer was washed twice with ion 151 323308 201211203, twice with 3% by weight aqueous acetic acid solution, and twice with ion-exchanged water. The organic layer was dropped into methanol and the resulting precipitate was filtered, and dried to give a solid. This solid was dissolved in toluene, and the toluene solution was again passed through a column packed with tantalum/alumina in advance through the flow of benzene. The precipitate after the flow was dropped into decyl alcohol, and the resulting precipitate was collected by filtration and dried to obtain 3.48 g of a high molecular compound (hereinafter referred to as "polymer compound H"). The polystyrene-equivalent amount of the polymer compound Η 依 分析 条件 # 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 From the monomer loading ratio, the polymer compound lanthanide is presumed to have the following repeating unit and molar ratio, and the repeating unit of (ΡΑ) and the repeating unit selected from (ΡΒ) are mutually polymerized. Compound. (PA) = 50

CeHi7 〇^n

(wherein, Me represents a fluorenyl group, and t-Bu represents a ternary butyl group.) &lt;Production and evaluation of an organic EL device. In addition, the polymer compound cerium is dissolved in diphenylbenzene at a concentration of 1.6% by weight. The solution in the solvent and the solution in which the luminescent organometallic complex compound MC-2 is dissolved in the diphenylbenzene solvent at a concentration of 1.6% by weight is mixed in a weight ratio of 92.5:7.5 to prepare a composition. 8 In place of the composition 6 of Example 5 of 152 323308 201211203, an organic EL device was fabricated. , 15 in the same way 'self: =: EL element after the application of voltage' can be obtained from the element of the compound _ 615 (10) with a peak of luminescence 'suspension two pieces from 2 · 5 ν start illuminate' at 5.5v shows lOOOcd The first luminous efficiency of the /m2 is 18.2〇cd/A.

(2) The initial luminance of the slightly obtained organic EL device becomes a circular cW3 type current value, and the current is driven by the current, and the luminance is branched, and as a result, the luminance is attenuated to the initial luminance after 63 hours. Attenuated to the initial brightness after 1482 hours. [Example 7] <Synthesis of Polymer Compound I> = 1' 4_double U' 3' 2-dioxonacyclopentan-2-yl)_2, 5-di=basic aig, 2.23 round D'u-bis(132-dioxaborolane(4-hexylphenyl) (1.44&amp;, 2.24_1), compound^9 (0.438, 0.56_〇1), palladium(II) acetate .6mg, ginseng (2_nonyloxyphenyl) phosphine 3.9 and hydrazine 43mL to a reaction vessel in which the internal gas is replaced by nitrogen, and mixed while heating on a side of 1 〇〇 C. Dropping in the reaction solution 2 〇% by weight of tetraethylammonium hydroxide aqueous solution l〇ml, reflux for 5 hours. After the reaction, add phenyl boronic acid 69mg, palladium acetate (iI) 〇 6mg, ginseng (2-methoxyphenyl) phosphine 3. 9 mg, 7 mL of toluene and 10 ml of a 10% by weight aqueous solution of tetraethylammonium hydroxide were refluxed for 15 hours. Next, an aqueous solution of sodium bisphosphonate (Sodium diethyldithiocarbamate) was added 153 323308 201211203 16 ml The mixture was stirred at 85 ° C for 2 hours, and the reaction solution was cooled to room temperature, diluted with toluene, and washed twice with water twice, 3 wt% aqueous acetic acid solution, and water 4 times. After the machine layer was dropped into methanol, a precipitate was formed. After the precipitate was filtered, it was dried to obtain a solid. The solid was dissolved in toluene, and the obtained solution was passed through an alumina column and a gel column to be purified. IxlO4, polystyrene. The polystyrene-equivalent number average molecular weight of the polymer compound I is 5. OxlO4, polyphenylene. The weight average molecular weight of the ethylene exchange is 1. lxlO5. The polymer compound I, the theoretical value obtained from the charged raw material, is a molar ratio of 40:10:40:10 including the following formula:

The repeating unit shown is of the formula:

(wherein Me represents a thiol group.) The repeating unit shown is as follows:

154 323308 201211203 The repeating unit shown is of the following formula:

(wherein t-Bu represents a third butyl group.) The copolymer of the repeating unit shown. φ &lt;Production and Evaluation of Organic EL Element&gt; In addition to a solution in which the polymer compound I was dissolved in a diphenylbenzene solvent at a concentration of 2.2% by weight and a luminescent organic metal complex compound MC at a concentration of 2.2% by weight -1 The solution dissolved in the xylene solvent was mixed in such a manner that the weight ratio was 70 · 30, the composition g was prepared to replace the composition 1 of Example 1, and the composition 9 was spin-coated and An organic EL device was produced in the same manner as in Example i except that the film was formed at a rotational speed of 1 Å. After applying a voltage to the obtained organic EL device, a self-luminous organometallic compound compound can be obtained from the device, and EL light having a peak at 52 (nm) can be obtained. The device started to emit light from 2.64V, and showed luminescence of brain m at 57v, and the maximum luminous efficiency was 62.80 cd/A. The current value was set such that the initial luminance of the organic EL element obtained above was cd/m2, and then driven at a constant current to measure the temporal change in luminance. As a result, the brightness was attenuated to the initial brightness after 82 hours. [Example 8] 323308 155 201211203 &lt;Synthesis of Polymer Compound J&gt; Measured 1,4-bis(1,3,2-dioxaborolan-2-yl)-2, 5- Dihexylbenzene (1·00g, 2. OOmmol), 1,3-bis 3, 2__dioxaborolan-2-yl)-2-mercaptobenzene (0.11g, 〇. 5〇) Mm〇1), 2,7-dibromo-9,9-bis(4-hexylphenyl)anthracene (1. 29g ' 2. 00_〇1), compound M-10 (0·58g, 0. 5mmol 5, palladium acetate (6 mg), ginseng (2-methoxyphenyl) phosphine 3. 5 mg and toluene 44 mL were placed in a reaction vessel in which the internal gas was replaced with nitrogen, and the mixture was heated while being heated at 100 °C. 9 ml of an argon-oxidized tetraethylammonium aqueous solution under a reaction liquid droplet of 20 Φ% by weight was refluxed for 11 hours. After the reaction, 62 mg of phenylboric acid, palladium acetate (!{)〇. 6 mg, ginseng (2-methoxyphenyl)phosphine 3. 5 mg, toluene 7 mL, and 20% by weight of tetraethylammonium hydroxide aqueous solution were added, The reflux was repeated for 15 hours. Next, 14 mL of a 2 M aqueous solution of sodium dithiodiamine citrate was added, and the mixture was stirred at 85 ° C for 2 hours. The reaction solution was cooled to room temperature, diluted with toluene, and washed with water twice, 3% by weight aqueous acetic acid twice, and water six times. The organic layer was precipitated by dropping into methanol. The (4) was subjected to healing and dried to obtain a solid. This solid was dissolved in a solution, and the obtained solution was purified by passing through a column of oxidized column and a column of Shiqi gum. After the droplets are precipitated in methanol, a polymer compound is obtained (hereinafter referred to as "polymer compound qing. The amount of the average numerator of the polystyrene-converted bismuth according to the analysis condition 2 is 4.9xlG'. The weight average molecular weight in terms of styrene conversion is I. 10° The molecular compound J' is calculated from the charged raw material, and the molar ratio of 40:Η:40:10 includes the following formula: 323308 156 201211203 ^6^13

C6H13

The repeating unit shown is of the formula: (wherein Me represents sulfhydryl.) The repeating unit shown by the formula:

The repeating unit shown is of the formula:

(wherein t-Bu represents a third butyl group.) The copolymer of the repeating unit shown. &lt;Production and Evaluation of Organic EL Element&gt; In addition to a solution in which a polymer compound J was dissolved in a toluene solvent of 157 323308 201211203 at a concentration of 2.2% by weight, and a luminescent organic compound was added at a concentration of 2.2% by weight. The solution in which the metal complex compound MC-1 is dissolved in the xylene solvent is mixed in such a manner that the weight ratio becomes 70:30, and the composition 1〇 is prepared to replace the point 1 of the composition 1 of the embodiment 1 and the composition 1 The organic EL device was produced in the same manner as in Example 1 except that the film was formed by spin coating at a rotational density of 1690 rpm. After applying a voltage to the organic EL device, the EL light having a peak of the self-luminous organometallic complex compound can be obtained from the device. The element started to emit light from 2.69v, and showed illumination of 1 〇〇〇cd/m2 at 5 4V, and the maximum luminous efficiency was 58 5 cdd/A. When the initial luminance of the organic EL element obtained above was set to 8 GO 〇 Cd / m 2 , the current value was set and then driven at a constant current, and the temporal change of luminance was measured. The material is 胄, after the hour (four) to the initial brightness. [Example 9] &lt;Preparation and evaluation of organic EL device&gt; In addition to a solution in which a polymer compound cerium was dissolved in a benzene solvent at a concentration of 2.2% by weight and a luminescent organic metal at a concentration of 2.2% by weight The solution in which the compound of the compound M03 was dissolved in a xylene solvent was mixed in such a manner that the weight ratio became 70:30, and the point at which the constituent core was substituted for the composition 9 of Example 7 was prepared, and the resultant product was spin-coated. An organic EL device was produced in the same manner as in Example 7 except that the film was formed at a rotational speed of 1,580 °. After the voltage is applied to the obtained organic EL device, the self-luminous organometallic complex compound Mc3 can have a wave of 323308 158 201211203 from 6G5nm. The element emits light from 2._, and the initial luminous efficiency at 7.6V_1000cd/m is 27.8Gcd/A. The initial luminance of the organic EL element to be described in the evening is changed to _〇cd/m2 and the current value is changed. In the same society, the motor is driven to measure the brightness. ... 'Expensively attenuated to the initial brightness after 41·9* [Example 1〇] &lt;Production and evaluation of organic EL device&gt; ::: Polymer compound was dissolved in a concentration of 2.2% by weight. The solution and the solution in which the luminescent organometallic complex compound MC-3 was dissolved in a formazan, 々w丄...7 鲜 fresh in a solvent, at a weight ratio of 2.2% by weight, was 70 in a weight ratio. The method of mixing 30, the system you add Q to the point of composition 12 to replace the composition 10 of Example 8, the bucket, M and the composition 12 by spin coating and An organic EL element was produced in the same manner as in Example 8 except that the film was taken at a rotation speed of 162 rpm. ^The obtained secret component shaft cake 4 can be obtained from the material. The organic metal complex compound (4) has a peak light at 6Q5nm. The unit has a maximum luminous efficiency of 24. 6 〇 cd/A. The light is emitted from 2.82 V. After the initial luminance of the organic EL device obtained above was set to the Ocd/m2^ type current value, the driving was performed at a constant current, and the luminance was measured. The result is 8 U% of the initial brightness of the fading after 5 hours of 6 〇 [Comparative Example 3] 323308 159 201211203 <Preparation and evaluation of organic EL elements> In addition to the concentration of 2.2% by weight The solution in the benzene solvent is dissolved in the dimeric compound MC-3 with 2.2 weight of the dimer compound E dissolved in the agricultural degree to make the ratio of the luminescent organic gold to 70:30, and the solution is adjusted in the medium. The organic EL device was produced in the same manner as in the case of the composition 5 of the first example and the point 13 in which the film U was formed at a rotation speed of 2400 rPm by the substitution ratio. In Comparative Example 1, the ruthenium luminescence which can be obtained from the element is obtained by applying a self-luminous organometallic compound (4) with respect to the obtained organic EL element. The component has a peak "luminescence" from the 2._open = Yucai (10) has a maximum luminous efficiency of 23.2; 3V shows a circle... After setting the current value of the second embodiment of the organic EL element obtained above, the electric power becomes _ 0cd/m was changed. As a result, the brightness was measured after 5.3 hours, and the time for measuring the brightness [Example U] was reduced to 80% of the initial brightness. <Production and Evaluation of Organic EL Element> II: Molecule The concentration of the compound _ in the diastereous compound Me_4 is such that the ratio of the organic to gold is 92. The solution of the glutamic acid in the xylene solvent is mixed by the weight of the group (10) t of the example 5 to prepare the composition. 14 was replaced with a cloth at a temperature of 2540, and the composition 14 was formed into a film by a spin coating method, and the same as that of Example 5 was used as an organic EL device. 323308 160 201211203 The obtained organic EL device was added. After the voltage, the EL luminescence from the luminescent organometallic compound compound MC-4 having a peak at 625 nm is obtained. The element emits light at a temperature of 2.41 V, and shows a 〇〇〇cd/m at 4.5 V. Illumination, maximum luminous efficiency is 11. 70cd/A When the initial luminance of the organic EL device obtained above was set to 8000 cd/m 2 , the current value was set, and then the driving was performed at a constant current, and the temporal change of the luminance was measured. As a result, the luminance was attenuated to 10 80 after the initial luminance. %. This is a 7.1 times longer than the comparative example 4. [Example 12] &lt;Production and Evaluation of Organic EL Element&gt; In addition to the polymer compound F at a concentration of 1.8% by weight The mixture of the solution dissolved in the xylene solvent and the solution in which the luminescent organometallic conjugate compound MC-3 is dissolved in the bisphenol solvent at a concentration of 1.8% by weight is mixed in a weight ratio of 92.5:7.5. The same procedure as in Example 5 was carried out in the same manner as in Example 5 except that the composition 15 was replaced with the composition of Example 5, and the composition 15 was spin-coated and formed at a rotational speed of 2570 rpm. After the voltage is applied to the obtained organic EL device, the EL light having a peak at 600 nm from the luminescent organometallic complex compound MC-3 can be obtained from the device. The device starts to emit light at 2.29V, at 4 . 2V shows that the luminescence of l〇〇〇cd/m2 has a maximum luminous efficiency of 31.20 cd/A. The initial luminance of the organic EL element obtained above is set to a value other than cd/m2, and the current value is set. The measurement was performed to measure the temporal change of the luminance. As a result, the luminance was attenuated to 161 323 308 201211203 80./◦ after the 593·8 hours, and this was compared with the comparative example 5, which showed a long life 5. 5. Times. [Example 13] &lt;Preparation and evaluation of organic EL device: In addition to a solution in which a polymer compound ρ was dissolved in a diphenylbenzene solvent at a concentration of 1.8% by weight and a luminescent organic metal was dissolved at a concentration of 18% by weight The solution in which the compound of the compound MC-5 is dissolved in the diphenylbenzene solvent is mixed in a weight ratio of 92.5:7.5, the composition 16 is prepared to replace the composition 6 of the embodiment 5, and the composition is The organic EL device was fabricated in the same manner as in Example 5 except that the material 16 was formed by spin coating® at a rotation speed of 2,740 rpm. After applying a voltage to the obtained organic EL device, EL light having a peak at 615 nm of the self-luminous organometallic compound compound MC-5 can be obtained from the device. The luminescence of the luminescence of the 10,000 cd/m2 is shown to be 20.40 cd/A. After setting the current value so that the initial luminance of the organic EL device obtained above was 8000 cd/m2, the driving was performed at a constant current, and the temporal change in luminance was measured. As a result, the luminance was attenuated to 80% of the initial luminance after 49. 6 hours. 9倍。 This is compared with the comparative example 6 shows a long life 8.9 times. [Example 14] &lt;Synthesis of Polymer Compound K&gt; 9,9-bis(4-n-hexylphenyl)-2,7-bis (4, 4, 5, 5-) was mixed under an inert gas atmosphere. Tetradecyl-1,3,2-dioxaborolan-2-yl)-indole (2.77 g), 9,9-dioctyl-2,7-bis (4, 4, 5 , 5-tetradecyl-1,3,2-dioxaborolan-2-yl)-$(〇. 943g), 9,9-bis(3-n-hexylbenzene 162 323308 201211203 base) -2, 7-dibromo (i. 86g), 2, 4-bis(4-bromophenyl)-6-(4-n-dodecylphenyl)-1,3,5-triterpene ( 0.999g), N,N,_bis(4-bromophenyl) 州川'-bis(2,6-dimethyl-4-t-butylphenyl)_14-phenylenediamine (0. 581g) And a stupid (ii4mL) ' stir while heating. To the mixture was added bis(triphenylphosphine)palladium dichloride (3.7 mg) and heated to 1 〇〇C, and 20% by weight aqueous solution of tetraethylammonium ethoxide (18.5 g) was added dropwise to heat. Reflux. Next, phenylboric acid (〇·〇65〇g), bis(triphenylphosphine) dichloride (3.70 mg), and 20% by weight of tetraethylammonium hydroxide aqueous solution (18.5 g) were added. Heated back through the night. After removing the aqueous layer from the reaction mixture, sodium N,N-diethyldithiocarbamate dihydrate (2.91 g) and ion-exchanged water (58 mL) were added, and the mixture was stirred at 85 ° C for 2 hours. After separating the organic layer of the reaction mixture from the aqueous layer, the organic layer was washed twice with ion-exchanged water twice, 3% by weight of an aqueous acetic acid solution, and ion-exchanged water three times. The organic layer was dropped into methanol and the resulting precipitate was filtered, and dried to give a solid. This solid was dissolved in toluene, and the resulting solution was passed through a column of ruthenium/alumina which was previously passed through benzene. The passed solution was dropped into methanol to precipitate a precipitate. The precipitate was collected by filtration, and dried to obtain a polymer compound (hereinafter referred to as "molecular compound" (") 4.25 g. The polymer compound K was subjected to polystyrene-converted quantity average amount measured by the analysis condition 2. (Μη) and weight average molecular weight (MW) are Mn=14xl〇5, 4. 3xl05. From the monomer loading ratio, the polymer compound κ is presumed to have 323308 163 201211203 with the following constituent units. The constituent unit of Zeng Gan (10) is a unit and is selected from (PA) ^6^13 (PB) c6h13

C12H25 36/14 Μβ/ΝΗ^-Ν Me ^/~Me t-Bu t-Bu 27.5/15/7.5 (wherein Me represents methyl 'n, which means n-butyl <production and evaluation of organic EL elements> ', the concentration of X 1.8% by weight of the polymer compound dissolved in the solution solvent in the toluene solvent. + 曰, a ', 18 weight concentration makes the luminescent organic all-compromise compound MC ~ 4 w The solution of the solution of the solution of the solution in the diterpene benzene solvent is mixed in such a manner that the weight is 92_5 · 7.5, and the composition 17 is prepared to replace the composition 6 of the embodiment 5, and The composition 17 was produced in the same manner as in Example 5 except that the composition 17 was spin-coated and formed at a rotation speed of 200 rpm. The organic EL element was applied to the obtained organic EL element. EL luminescence having a peak from 625 (10) from the luminescent organometallic complex compound MC_4 was obtained. The luminescence was started from 2. The luminescence of the (4)/amperance was shown on page 4. (4), and the maximum luminous efficiency was 11.40 cd/ A. The current value is set such that the initial luminance of the organic EL element obtained above is 8 〇〇〇 cd/m 2 , and then the electricity is set. The flow was driven and the time change of the luminance was measured. As a result, the twist was attenuated to 80% of the initial luminance after 71·1 hour, which was 4.44 times longer than that of Comparative Example 4. 164 323308 201211203 [Example 15] <Preparation and evaluation of organic EL device> A solution in which a polymer compound κ was dissolved in a diphenylbenzene solvent at a concentration of 1.8% by weight and a luminescent organic metal at a concentration of 1.8% by weight were used. The solution of the complex compound MC-3 dissolved in the diphenylbenzene solvent is mixed in a weight ratio of 92.5:7.5, and the composition 18 is prepared to replace the composition 6 of the embodiment 5, and The composition 1 was produced by the same manner as in Example 5 except that the film was formed by spin coating at a rotation speed of 2120 rpm, and an organic EL device was produced. After the voltage was applied to the obtained organic EL device, the device was obtained. The EL luminescence from the luminescent organometallic compound compound MC-3 having a peak at 600 η π is obtained. The device starts to emit light at 2.26 V, and exhibits a light emission of 1 Q〇〇cd/m 2 at a frequency of 3.9 V, and the maximum luminous efficiency is 30. . 90cd/A. When the initial luminance of the obtained organic EL device was set to 8000 cd/m2, the current value was set, and the driving was performed at a constant current, and the time for measuring the luminance was changed. As a result, the luminance was attenuated to 360% after the initial brightness of 360. In the case of the comparative example 5, the lifetime is 3.49 times. [Example 16] <Production and evaluation of organic EL device> The polymer compound κ was dissolved in a concentration of 1.8% by weight. The solution in the diterpene benzene solvent and the solution in which the luminescent organometallic conjugate compound MC-5 was dissolved in the xylene solvent at a concentration of 1.8% by weight were mixed so that the weight ratio became 92.5:7.5, and the composition was prepared. μ was replaced in the same manner as in Example 5 by substituting the point of the composition 6 of Example 5 and the composition 19 by spin coating and 323308 165 201211203 at a rotational speed of 2090 rpm. EL component. After the voltage is applied to the obtained organic EL element, the EL light having the peak of the self-luminous organometallic compound compound MC-5 at 61151111 can be obtained from the element. The light-emitting efficiency of 19.000 volts is shown at 2.27 V, and the luminous efficiency of i000 cd/m 2 is shown at 4.3 V, and the maximum luminous efficiency is 19.60 cd/A. After setting the current value so that the initial luminance of the organic EL element obtained above was 8 〇〇〇 cd/m 2 , the driving was performed at a constant current, and the time at which the luminance was measured was changed. As a result, the luminance was attenuated to 80% of the initial luminance after 297.1 hours.倍倍。 The longer life of 5. 35 times compared with the comparative example 6. [Example 17] &lt;Synthesis of Polymer Compound L&gt; In a noble gas atmosphere, 9,9-bis(4-n-hexylphenyl)_2,7-bis(4,4,5,5-tetra was mixed). Mercapto-1,3,2-dioxaborolan-2-yl)-indole (〇.7542), 9,9-dioctyl-2,7-bis (4,4,5, 5-tetradecyl-1,3,2-φ dioxaborolan-2-yl)- (0.259 g), 9,9-bis(3-n-hexylphenyl)-2,7 -dibromo (〇.6022), 2,4-bis(4-bromophenyl)-6-(3,5-bis(4-t-butylphenyl)phenyl)-1,3,5 - three tillage (0.210g), N,N,-bis(4-bromophenyl)-ν, Ν'-bis(2,6-dimethyl-4-tert-butylphenyl)-1,4 - phenylenediamine (〇. i59g) and toluene (35mL) were stirred while heating. Di-hydrogenated bis(triphenylphosphine)le (l. 〇mg) was added to the mixture and heated to 100 ° C, and 20% by weight aqueous solution of tetraethylammonium hydroxide (7. 64 g) was added dropwise. hour. Next, phenylboric acid (0.035 g), bis(triphenylphosphine)palladium dichloride 166 323308 201211203 (1.0 mg), and 20% by weight aqueous tetraethylammonium hydroxide solution (7.6) were added. Heat the reflux overnight. After removing the aqueous layer from the reaction mixture, sodium N,N-diethyldithiocarbamate trihydrate (0.40 g) and ion-exchanged water (8 mL) were added at 85. Stir under the arm for 2 hours. After the organic layer of the reaction mixture was separated from the aqueous layer, the organic layer was washed twice with 36 wt% hydrochloric acid twice, 2.5 wt% aqueous ammonia solution twice, and ion-exchanged water four times. The organic layer was dropped to sterol to precipitate a precipitate. The sediment was filtered and dried to obtain a solid. This solid was dissolved in toluene, and the resulting solution was passed through a column in which the toluene was oxidized in advance. The passed solution was dropped into decyl alcohol, and the resulting precipitate was collected by filtration and dried to obtain a polymer compound (hereinafter referred to as "polymer compound L") 1.21 g. The mass average molecular weight (Mn) and the average molecular weight (Mw) of the weight of the polystyrene were measured by the amount of 4 Mn = 7. 3xl04, Mw = 2. 1X 105, respectively. From the monomer loading ratio, the polymer compound L is presumed to have the following constituent units and the molar ratio, and the constituent unit of *(pA) and the qi unit selected from (PB) are mutually polymerized. A polymer compound. (ΡΑ)

^6^13 35.5/14 C6H13 c8h17 CjH17 (PB) c6h13

^ ^ ^ Me Ο-Me Me-〇t-Bu t-Bu t-Bu 32.5/10/7.5 t-Bu (wherein Me represents a methyl group and t_Bu represents a third butyl group 167 323308 201211203 &lt;Organic EL element Preparation and evaluation> The concentration of toluene H=2.G% by weight is such that the reduction of the polymerized compound in the dimethyl group 4 is reduced by the weight of the compound Mr 9, the λ λ λ and the ItU The solution in the &amp; 5: 7 5 U 3 benzene solvent is mixed by weight twisting, the composition 20 is prepared to replace the cloth and the point of the composition of 35 nrT is 6 and the composition 2G is spin coated.

An organic EL device was produced in the same manner as in Example 5 except that the film was formed at a rotational speed. Spontaneously: Γ: The organic EL element is applied with a voltage, and the EL metal compound compound MC_2 which can be obtained from the element has a peak at 615 nm, and the element emits light from 2.2_ at the beginning of the period. The luminescence 'maximum luminous efficiency is 18.20 cd/A. The initial luminance of the organic EL element known as j is set to 8 cd/jfl2, and the driving current is driven by a constant current to measure the temporal change of luminance. As a result, the luminance was attenuated to the initial luminance after 238 hours.倍倍。 3. The ratio of the longevity was 3.78 times. [Example 18] &lt;Preparation and evaluation of organic EL device&gt; In addition to the solution in which the polymer compound L was dissolved in a diphenylbenzene solvent at a concentration of 2.0% by weight, and the luminescence at a concentration of 2.0% by weight The solution in which the organometallic compound compound MC-3 is dissolved in the diterpene solvent is mixed in such a manner that the weight ratio becomes 92·5:7.5, and the composition 21 is prepared to replace the composition 6 of the embodiment 5, and The organic EL element was produced in the same manner as in Example 5, except that the film was formed by spin coating at a rotation speed of 3000 rpm, in the same manner as in Example 5, 323308 168 201211203. After applying a voltage to the obtained organic EL device, EL light having a peak at 600 nm of the self-luminous organometallic compound compound MC-3 can be obtained from the device. The device started to emit light at 2.24 V, and showed light emission of l〇〇〇cd/m2 at 4.2 V, and the maximum luminous efficiency was 29.80 cd/A. The current value was set such that the initial luminance of the organic EL device obtained above was 8000 cd/m2, and then driven at a constant current to measure the temporal change in luminance. As a result, the luminance was attenuated to #80% of the initial luminance after 517.3 hours. This is a long life with respect to the comparative example 5, 5.2 times. [Example 19] &lt;Preparation and evaluation of organic EL device&gt; The solution in which the polymer compound G was dissolved in the dimethyl solvent at a concentration of 1.8% by weight and the luminescence at a concentration of 1.8% by weight The solution in which the organometallic compound compound MC-4 is dissolved in the xylene solvent is mixed in a weight ratio of 92.5:7.5, and the composition 22 is prepared to replace the composition 6 of the embodiment 5, and An organic EL device was produced in the same manner as in Example 5 except that the composition 22 was spin-coated and formed at a rotation speed of 2,500 rpm. After the voltage was applied to the obtained organic EL device, the self-luminous organometallic compound compound MC-4 obtained from the device had a peak-EL emission at 625 nm. This element started to emit light from 2.4^, and showed a luminous efficiency of i〇〇〇cd/m2 of '1.4 〇cd/A at 4 6V. The initial luminance of the organic EL element obtained above was set to 8 〇〇〇cd/m2, and the current was driven by a constant current, and the time for measuring the luminance was changed to 323308 169 201211203. As a result, the luminance was attenuated to 80% of the initial luminance after 86 hours. This is a long life of 5.38 times compared with the comparative example 4. [Example 20] &lt;Preparation and evaluation of organic EL device&gt; A solution in which a polymer compound cerium was dissolved in a diphenylbenzene solvent at a concentration of 1.8% by weight and a concentration of 1.8% by weight was used. The solution of the organometallic complex compound MC-3 dissolved in the dimethyl solvent is mixed in a weight ratio of 92.5:7.5, and the composition 23 is prepared to replace the composition of the embodiment 6 An organic EL device was produced in the same manner as in Example 5 except that the composition 23 was spin-coated and formed at a rotation speed of 2370 rpm. After applying a voltage to the obtained organic EL device, EL light having a peak at 600 nm of the self-luminous organometallic compound compound MC-3 can be obtained from the device. The light-emitting efficiency of the light-emitting illuminating efficiency of 31 cd/m is shown in Fig. 3V. When the initial value of the organic EL element obtained above was set to 8000 cd/m2, the current value was set, and then driving was performed at a constant current to measure the temporal change in luminance. As a result, the luminance was attenuated to 80% of the initial luminance after 308.1 hours. This is a long life of 2.99 times compared with the comparative example 5. [Example 21] &lt;Production and Evaluation of Organic EL Element> A solution in which the polymer compound G was dissolved in a xylene solvent at a concentration of 1.8% by weight and a luminescent organic metal at a concentration of 1.8% by weight The solution of the complex compound MC-5 dissolved in the xylene solvent is mixed in a manner of a weight of 170 323308 201211203 to be 92.5:7.5, and the composition 24 is prepared to replace the composition 6 of the embodiment 5, and An organic EL device was produced in the same manner as in Example 5 except that the composition 24 was spin-coated and formed at a rotation speed of 2,500 rpm. After applying a voltage to the obtained organic EL device, EL light having a peak at 615 nm of the self-luminous organometallic compound compound MC-5 can be obtained from the device. The element started to emit light from 2.39 V and showed a light emission of 1000 cd/m 2 at 5.0 V, and the maximum luminous efficiency was 20.40 cd/A. The current value was set such that the initial luminance of the organic EL device obtained above was 8000 cd/m2, and then driven at a constant current to measure the temporal change in luminance. As a result, the luminance was attenuated to 80% of the initial luminance after 443.4 hours. This is a long life of 7.99 times compared with the comparative example 6. [Comparative Example 4] &lt;Preparation and evaluation of the organic EL device, except that the polymer compound was dissolved in a diterpene solvent at a concentration of 1.4% by weight and the luminosity was adjusted at a concentration of 1.4% by weight. The solution in which the organometallic compound compound MC-4 is dissolved in the dimethyl solvent is mixed in a weight ratio of 92.5:7.5, and the composition 25 is prepared to replace the composition 6 of the embodiment 5, and An organic EL device was produced in the same manner as in Example 5 except that the composition 25 was spin-coated and formed at a rotation speed of 2000 rpm. After applying a voltage to the obtained organic EL device, EL light having a peak at 625 nm of the self-luminous organometallic compound compound MC-4 can be obtained from the device. The element emits light from 2.59V, and shows the luminescence of the i〇〇〇cd/ 323308 171 201211203 m2 at the 5· IV. The maximum luminescence effect makes the organic EL obtained from the above. After setting the current value, the initial brightness of the member &amp; amp changes to _cd/m2. As a result, the brightness is on ^;: the time of turning, 骇 brightness is 8〇%. After lb.u, the attenuation was reduced to the initial brightness [Comparative Example 5] <Preparation and evaluation of organic EL elements>

Except that the concentration of _, Ψ ^ ^ ^ , 4 > will be determined by a concentration of 1.5% by weight, and the solution of the molecular compound H dissolved in the dimethyl methacrylate mixture is 1% by weight of 1 曰A. The concentration of the luminescent organometallic complex compound MC-3 is dissolved...no The solution which is cold-dissolved in a toluene solvent is mixed in a manner of a weight of 5.7, and the composition 26 is prepared to replace the «Example 5 The organic EL device was produced in the same manner as in the Example except that the point of the composition 6 and the film formation of the film were rotated by a spin coating at a rotational speed of 295 G rpm. 5V, starting from 2.46V, at 4. 5V, the light-emitting organometallic compound compound MC-3 is obtained from the element. The luminescence of 1 〇〇〇 cd / m 2 is shown, and the maximum luminous efficiency is 29.1 〇 cd / A. The current value was set such that the initial luminance of the organic EL element obtained above was 8 〇〇〇 cd/m 2 , and then driven at a constant current to measure the temporal change in luminance. As a result, the brightness is 80% of the initial brightness after the muscle tendon is small. [Comparative Example 6] &lt;Production and Evaluation of Organic EL Element 323308 172 201211203 A solution in which a polymer compound hydrazine was dissolved in a xylene solvent at a concentration of 1.. 4% by weight was used and a concentration of 1.4% by weight was used. The solution in which the luminescent organometallic complex compound MC-5 is dissolved in the diphenylbenzene solvent is mixed so that the weight ratio becomes 92·5:7.5, and the composition 27 is prepared to replace the composition 6 of the embodiment 5. An organic EL device was produced in the same manner as in Example 5 except that the composition 27 was spin-coated and formed at a rotation speed of 2 〇 rpm.

After applying a voltage to the obtained organic EL device, EL light having a peak at 615 nm of the self-luminous organometallic compound compound MC-5 can be obtained from the device. The light-emitting efficiency is 18.60 cd/A. The light-emitting efficiency is 18.60 cd/A. When the initial value of the organic EL element obtained above was set to 8000 cd/m2, the current value was set, and the time during which the driving was measured was changed by a constant current. As a result, the luminance was attenuated to 80% of the initial luminance after 55·5 hours. [Example 22] &lt;Synthesis of Compound Μ_11&gt; * Synthesis of CM-16

CM-14

(wherein Me represents a methyl group and t-Bu represents a third butyl group.) In a separable flask in which an internal gas is replaced by an argon gas, 3,5-dibromo 173 323308 201211203 -4-decyl benzoic acid is added. Compound CM-14, 60 g, 205 mmol), compound CM-15 (200 g, 430 mrool), bis(triphenylphosphine)palladium dichloride (8 6 g, 12 mmol, 6 mol%) and toluene (13 mL). Heat to 90 C while stirring. Next, 20% by weight of a tetraethylammonium hydroxide aqueous solution (600 mL) was dropped. After the completion of the dropwise addition, the mixture was heated to reflux for 24 hours. The reaction solution was transferred to a separatory funnel, and washed with 0.5 mol/L hydrochloric acid and 1 wt% saline. The organic layer was dehydrated with magnesium sulfate, and then passed through a funnel filled with silicone to decompress the solvent. Take care of it. The obtained residue was recrystallized from a gas-methanol-based Φ to obtain a white compound CM-16.

(wherein Me represents a methyl group and t-Bu represents a third butyl group.) A compound CM-16 (41 g '50 mmol), monochlorobenzene (i〇〇) is added to a separable flask in which internal gas is replaced by argon gas. mL) and DMF (0.1 mL) were heated and stirred at Φ 60 °C. Next, Thionyl chloride (12.5 g, 105 mmo, 2.1 equivalent) was slowly dropped. After heating and stirring for 10 hours or more, the vehicle was depressurized to remove the solvent. Monochlorobenzene (200 mL) and 4-bromobenzonitrile (18 g, 100 mmol) were added to the residue, and the reactor was ice-cooled and stirred. Next, the five gasified hydrazine (15 g, 50 mmol) was dripped slowly, and after completion of the dropping, the temperature was raised to room temperature, and the mixture was stirred for 48 hours or more. The resulting reaction mixture was added dropwise to a 25% by weight aqueous ammonia solution while stirring. When the organic layer is precipitated or forms an emulsion, it is diluted with chloroform into 174 323308 201211203. The aqueous layer was removed from the reaction solution, and the organic layer was washed twice with ion-exchanged water and dehydrated with sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was dissolved in chloroform. The mixture was passed through a funnel filled with silica gel, and then the solvent was evaporated under reduced pressure. The obtained residue was recrystallized from a chloroform-decanol system to obtain a white compound oxime-11. [Simple description of the diagram] None. [Main component symbol description] • None.

175 323308

Claims (1)

201211203 VII. Patent application scope: 1. A molecular compound containing a repeating unit represented by the formula (丨) and a repeating unit represented by the formula (2). (wherein R1, R2, R3, R4 and R5 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group. , aralkoxy, arylalkylthio, fluorenyl, decyloxy, decylamino, quinone imine, imine residue, substituted fluorenyl, substituted fluorenyloxy, substituted fluorenylthio, a monovalent aromatic heterocyclic group, a heteroaryloxy group, a heteroarylthio group, an aralkenyl group, an aralkynyl group, a substituted carboxyl group or a cyano group, and at least one of R1, R2, R3, R4 and R5 represents a group other than a hydrogen atom, an adjacent group of R, R2, R3, R4 and R5 may be bonded to each other to form a ring; and An and An are each independently represented to have an alkyl group, a decyloxy group, an alkyl group. Thio, aryl, aryloxy, arylthio, arylalkyl, aralkyloxy, arylalkylthio, decyl, decyloxy, decylamino, quinone imine, sub Amine residue, substituted fluorenyl group, substituted fluorenyloxy group, substituted fluorenylthio group, monovalent aromatic heterocyclic group, heteroaryloxy group, heteroaryl group, aralkenyl group, arylalkyne group, substitution Silk and cyano Aromatic group constituting the divalent group of the substituent group) 3,233,081,201,211,203 (wherein, An represents an aryl group or a monovalent aromatic heterocyclic group; and An represents a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an aromatic group; Alkyl, aryloxy, arylalkylthio, decyl, decyloxy, decylamino, quinone imine, imine residue, substituted amine, substituted fluorenyl, substituted fluorenyloxy a substituted mercaptothio group, a substituted mercaptoamine group, a monovalent aromatic heterocyclic group, a heteroaryloxy group, a heteroarylthio group, an aralkenyl group, an aralkynyl group, a substituted carboxyl group, or a cyano group; Represents alkyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, arylalkyl, aralkoxy, arylalkylthio, decyl, decyloxy, Amidino, oximine, imine residue, substituted amine, substituted fluorenyl, substituted fluorenyloxy, substituted fluorenylthio, substituted fluorenylamino, monovalent aromatic heterocyclic, hetero Aryloxy, heteroarylthio, aralkenyl, aralkynyl, substituted carboxy or cyano; when plural R6 are present, these R6 may be the same or different; a represents 〇 or 1 'exist 2 A can be the same or different). 2. The polymer compound according to claim 1, wherein at least one of the above-mentioned 1^, 1^, 1^, 1^ and ¥ is an alkyl group-containing group, and the alkyl group-containing group The polymer compound according to claim 1, wherein at least one of R1, R2, R3, R4 and R5 is at least one of the above-mentioned R1, R2, R3, R4 and R5. A burnt group having 12 or more carbon atoms. 4. The polymer compound according to claim 1, wherein the above R2 and R4 are an alkyl group-substituted aryl group. 5. The polymer compound according to claim 1, wherein the Ar4 hydrogen atom, an alkyl group, an aryl group or a monovalent aromatic heterocyclic group is used. 6. The polymer compound according to claim 1, wherein the An and Ar2 groups are each independently a divalent aromatic group represented by the formula (3) or the formula (4). (3) (wherein R' represents an argon atom or an alkyl group). 7. The polymer compound according to claim 1, wherein the repeating unit represented by the above formula (1) and the repeating unit represented by the above formula (2) are all repeating units constituting the polymer compound. The total ratio is 30% or more. 8. The polymer compound according to claim 1, wherein the repeating unit represented by the formula (5), 323308 201211203 -Ar5 (5) (wherein Ars represents an aryl group or a divalent group) Aromatic heterocyclic group). 9. The polymer compound according to claim 8, wherein the repeating unit represented by the above formula (5) is a repeating unit represented by the formula (6), (wherein, Are and An each independently represent an alkyl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, an arylalkyl group, an aralkyloxy group, an arylalkylthio group. , mercapto, anthracenyloxy, fluorenylamino quinone imine, imine residue, substituted amine, substituted fluorenyl, substituted fluorenyloxy, substituted fluorenylthio, substituted fluorenylamine, heteroaryl Alkoxy, heteroarylthio, aralkenyl, arylalkynyl, substituted carboxy, or cyano; R represents non-alkyl, alkoxy, alkylthio, aryl, aryloxy, aryl Thio group, aryl alkyl group, aryl alkoxy group, arylalkylthio group, mercapto group, decyloxy group, arylamino group, flavonimide, imine residue, substituted amine group, substituted thiol group, Substituted fluorenyloxy, substituted mercaptothio, substituted mercaptoamine, monovalent aromatic heterocyclic, heteroaryloxy, heteroarylthio, aryl, aralkynyl, substituted carboxy or Cyano; a means 0 or 1, the presence of 2 a may be the same or different; when there are a plurality of R7 'these may be the same or different). 10. The polymer compound according to item 8 of the patent application, wherein the first unit of the formula (5) of the above formula 323308 4 201211203 is selected from the repeating unit represented by the formula (7) and the formula (8). Among the groups of repeating units shown, R8 Wherein R8 and R9 each independently represent alkyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, arylalkyl, aralkoxy, arylalkyl Thiothio group, mercapto group, decyloxy group, decylamino group, quinone imine group, imine residue, substituted amine group, substituted fluorenyl group, substituted fluorenyloxy group, substituted fluorenylthio group, substituted fluorenylamino group , an aromatic heterocyclic group, a heteroaryloxy group, a heteroarylthio group, an aralkenyl group, an aralkynyl group, a substituted carboxyl group or a cyano group) Wherein 'R and R each independently represent alkyl, alkoxy, alkylthio, aryl, aryloxy, arylthio, arylalkyl, aralkyloxy, arylalkyl Thiothio group, mercapto group, decyloxy group, decylamino group, quinone imine group, imine residue, substituted amine group, substituted fluorenyl group, substituted fluorenyloxy group, substituted fluorenylthio group, substituted fluorenylamino group a monovalent aromatic heterocyclic group, a heteroaryloxy group, a heteroarylthio group, an aryl group, an aralkynyl group, a substituted sulfo group or a cyano group; b represents 0 or 1). 11. The polymer compound according to claim 8, wherein the repeating unit, y, y, and y, as shown in the above formula (1), 5 323 308 201211203, are all the repeating units constituting the polymer compound. Repeating unit (7) The repeating unit represented by the formula (2) and the above formula (5) 12. The total ratio of the patent application is 80 mol% or more. And a polymer compound according to the above formula (9), wherein the repeating unit is (9) (wherein Ar8 Λ 13 aryl or divalent ^ Ar9, Am and Aru each independently represent an aromatic heterocyclic group independently; and Ar&quot;, Arlz and Aru each independently represent or a monovalent aromatic A heterocyclic group; X&amp;y is a composition of each of them, but the value of X + y is 〇 or 1). a molecular compound, which is combined with a product of the high-gloss material described in claim 1 of the patent application, a self-hole transmission material, an electron transport material, and a call, and at least one of the materials. The group of the three items of the heart; the luminescent material is a luminescent organic metal complex compound. A liquid composition comprising the polymer compound described in claim 1 and a solvent or a dispersion medium. 16. A thin mash comprising a polymeric compound as described in the scope of the patent application. 17. An element comprising: an electrode comprising an anode and a cathode, and an organic layer comprising a compound of the polymer 323308 6 201211203 according to the patent scope f i disposed between the electrodes. 18. A planar light source having the elements described in claim 17 of the patent application. 19. A display device comprising the components of the first application of the patent application. 20. a compound of the formula (i), (wherein, Ra, Rf and Rg each independently represent a hydrogen atom or a burnt group; and Rb, Re, Rd and Re each independently represent an alkyl group or an alkyl group substituted by an alkyl group; and Ar1 and Ar2 are each independently The representation may have a group selected from the group consisting of an alkyl group, an alkoxy group, a thiol group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an aralkyloxy group, an arylalkylthio group, a fluorenyl group. , anthraceneoxy, decylamino, quinone imine, imine residue, substituted fluorenyl, substituted fluorenyloxy, substituted ylthiol, monovalent aromatic heterocyclic, heteroaryloxy, a divalent aromatic group of a substituent in a group consisting of a heteroarylthio group, an aralkenyl group, an arylalkynyl group, a substituted carboxyl group, and a cyano group; X represents a halogen atom, a boric acid stabilizing residue, an arm residue, and a formula a group represented by (a-1), a group represented by formula (a-2), a group represented by formula (a-3) or a group represented by formula (a-4), wherein two X may be Same or different) 7 323308 201211203 (wherein RT represents an alkyl group or an aryl group) - MgXA (a-2) (wherein XA represents a halogen atom) - ZiXA (a^3) (wherein XA is synonymous with the foregoing) -Sn(RT)3 (wherein RT means synonymous with the foregoing, and the three RTs present may be the same or different). 323308 201211203 IV. Designated representative map: (1) The representative representative of the case is: There is no schema in this case. (2) A brief description of the symbol of the representative figure: None. 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 3 323308