TWI287570B - Polymer compound and polymer luminescent element using the same - Google Patents

Abstract

A polymer compound is provided. The polymer compound is characterized by containing one repeating unit represented by the formula (1), and having a polystyrene-reduced number average molecular weight of 10<3> to 10<8>. Wherein Ar1 and Ar2 each represent an aromatic hydrocarbon group or a heterocyclic group; X1 and X2 represent C(=O) or C(R1)(R2) for one, and O, S or C(=O) for another one; M represents O-C(=O), C(=O)-O, O, S, C(=O) or the like; Z1 represents -CR=CR- or -C=C-; and d represents 0 or 1.

Description

[Technical Field] The present invention relates to a polymer compound and a high molecular light-emitting device (hereinafter, also referred to as a polymer led (light-emitting diode)) using the polymer compound. [Prior Art] Since a high molecular weight luminescent material is different from a low molecular weight luminescent material, it can be dissolved in a solvent and can form a luminescent layer using a light-emitting element according to a coating method. There are many studies on this aspect, For example, polyphenylene extended ethylene derivatives, polyfluorene derivatives, polyphenylene derivatives, and the like are known. Further, in the case where the ortho positions constituting the aromatic ring of the biphenyl ring are bonded to each other, and the biphenyl group having a structure of 5 to 7 members is formed by two to three atoms or a group of atoms, A polymer compound represented by the following formula is disclosed in Patent No. 01/96454.

Bajia, A and B indicate that cm_N=CR1_, CR1=CR2 (called. This ° already contains this polymer compound as a matrix, and this mixture is a private one, 'and this metal 硪In order to form a light-emitting layer, in addition, in the patent of the Japanese Patent Laid-Open No. 8_81, a tetrazolium m-diyl derivative, there is no poly(4,5,9,1〇[Inventive content J, the inventor, etc. can be used as a light Innovative high scores for material use 314723 5

I25/3/U compound concentrates on the result of the study, the ring, and has the aromatic ring to have two aromatic compounds in the repeating unit, which is suitable for the high score X of the structure formed by the combination of the meaning bond Only then can the material or the cost of the invention. In the end, the present invention relates to a repeating unit represented by the average number of polystyrenes (1) in terms of polystyrene. = knife 1 is 1χ 1〇3 to lx 1〇8 high score X1 X2

(1) A tetravalent aromatic hydrocarbon group or 4 [wherein, Ar丨 and Ar2 each independently represent a heterocyclic group of a valence. X1 and X2 represent either - c (, or c (ri) (r2) and the other is 〇, S, c (=0), s (= Q), sc > 2, Si (R3) (R4) , N(R5), from 6), P(R7) or p(=o)(r8). Wherein 'R丨, R2, R3, R4, R5, R6, R7mR4^ represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkylamino group, an aryl group, an aryloxy group, Arylthio, arylamino, aralkyl, arylalkoxy, arylalkylthio, arylalkylamino, fluorenyl, decyloxy, decylamino, imido, substituted methylation, Substituted for a decyloxy group, a substituted formazan thiol group, a substituted carbarylamino group, a monovalent heterocyclic group, an aralkenyl group, an arylethynyl group or a cyano group.) Μ represents a formula (2), a formula (3) Or the formula (4) represents the basis. 314723 6 1287570 [wherein, y1 and γ2 independently represent 〇, s, c(=〇), s(=〇), S〇2, C(R9)(Rl.), Si(Ru)(Rl2), n(r13), B(R14), p(Ri5) or P( = 〇)(R16). (wherein R9, R1, Rii, Ru, r13, r14, r15 and r16 each independently represent a hydrogen atom, a dentate atom, an alkyl group, an alkoxy group, an alkylthio group, an alkylamino group, a #基基, Oxyl, arylthio, arylamino, aralkyl, arylalkoxy, arylalkylthio, arylalkylamino, decyl, decyloxy, decylamino, imido, substituted hydrazine a decyl group, a substituted methoxyalkyloxy group, a substituted carbaryl thio group, a substituted methantylamino group, a heterocyclic group of an anthracene group, an aralkenyl group, an arylethynyl group or a cyano group.) However, γ ΐ is c(r9) ( When r1〇) and si(Rll) (Rl2) are not, Y1 and γ2 are not the same. ] -γ3 = γ4_ (3) [wherein, Υ3 and Υ4 each independently represent Ν, Β, Ρ, C(R17) or Si(R18) 〇 (wherein, R17 and Ru independently represent a hydrogen atom, a halogen atom, Alkyl, alkoxy, alkylthio, alkylamino, aryl, aryloxy, arylthio, arylamino, aralkyl, arylalkoxy, arylalkylthio, arylalkylamine Base, benzyl, decyloxy, decylamino, imido, substituted, methoxyalkyl, substituted, methoxy, substituted, methyl thio, substituted decylamino, monovalent heterocyclic, aral , arylethynyl or cyano.)] -Y5- (4) [wherein Y5 represents 〇, s, c( = 0), S( = 0), S02, C(R19)(R20),

Sl(R2))(R22), N(R23), b(r24), p(R25) or p(= 〇)(r26). 7 314723 1287570 (wherein R19, R20, R21, R22, R23, r24, r25 and R26 each independently represent a hydrogen atom, a dentate atom, an alkyl group, an alkoxy group, a sulfur-burning group, an alkylamino group, an aryl group, Aryloxy, arylthio, arylamino, aralkyl, aryl alkoxy, arylsulfanyl, arylamino, aryl, acidoxy, arylamino, imine, substituted a decyl group, a substituted methoxyalkyloxy group, a substituted formazanylthio group, a substituted megrolylamino group, a monovalent heterocyclic group, an aralkenyl group, an arylethynyl group or a cyano group.]]

Zi means -CR36 = CR37- or -Ce C-. R36 and R37 each independently represent a hydrogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group or a cyano group. d is 〇 or 1 〇 ] [Embodiment] Hereinafter, the polymer compound of the present invention and a polymer light-emitting device using the polymer compound will be described in detail. In the formula (1), 'Ar1 and Ar2 each independently represent a tetravalent aromatic hydrocarbon group or a tetravalent heterocyclic group. Both of Ari and Ar2 are preferably a tetravalent aromatic hydrocarbon group, and both of them are preferably a monocyclic tetravalent aromatic hydrocarbon group. Here, the tetravalent aromatic hydrocarbon group means the atomic group remaining after removing four hydrogen atoms from the benzene ring or the condensed ring, and is usually a carbon number of 6 to 6 Å, preferably 6 to 20, and can be exemplified as follows. Compound. Here, the substituent may be substituted on the aromatic hydrocarbon group, and the substituent may be exemplified by a porphin atom, a hydroxyl group, an alkyl group, an alkoxy group, an alkylthio group, an alkylamino group, an aryl group, an aryloxy group, or an aromatic sulfur. Alkyl, arylamino, aralkyl, arylalkoxy, arylalkylthio, arylalkylamino, fluorenyl, decyloxy, decylamino, imido, substituted f矽alkyl, substituted hydrazine a decyloxy group, a substituted methanyl thio group, a substituted carbaryl amino group, a fluorene heterocyclic ring 314723 8 1287570, a aryl group, an aryl ethynyl group or a cyano group. Does not contain the carbon number of the substituent. The carbon number of the hydrocarbon group can be exemplified as follows.

The term "bicyclic group means the atomic group remaining after removing four nitrogen atoms from the heterocyclic compound", and the 5?^ double oxime is from 4 to 60, preferably to 20. Further, in the anti-number of the same substituent 'the base' of the heterocyclic group % ^ ^ , upper, and the fluorene hydrocarbon group, the carbon number of the substituent is not included. 314723 9 1287570

11 314723 1287570

(2 2) 12 314723 1287570

(2 4) 秘加如如)6:v ^c&gt;- )6c:&gt;- ^ 被, (2 5) In the above formula, ΪΤ independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group , alkylthio, alkylamino, aryl, aryloxy, arylthio, arylamino, aralkyl, arylalkoxy, arylalkylthio, arylalkylamino, decyloxy, Amidino, arylalkenyl, arylalkynyl, monovalent heterocyclic or cyanide 314723 1287570. R'' independently represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, a substituted indenyl group, a fluorenyl group, or a monovalent heterocyclic group. X1 and Ar2 are bonded to the adjacent positions of the aromatic ring carbon of Ar1, and X2 and Ar 1 are preferably bonded to the adjacent positions of the aromatic ring carbon of Ar2.

-X1- X2- can be exemplified as the following: 00 0 0 0 0 0 0 11 II II II II II II II 1 C 0 -1 έ 1 S - ―C- -c- ―CS— -C a 0 0 R3 I Ο f 0 R6 0 R7 0 0 II II _ 1. Π 1 Μ 1 η 丄 II II

I

IN R1_ o R1lc s 1R1C- one 1P——c

OHS 1R—6 —r8o=&lt;

3 _ R—£ I R1丨 C R7I- 2 丨Ri 6 RII 丨r2r1—c; 5 RI —r2r1—/

_no ONHn 2 1 j R RIC w -ΟΙ Ο一-π- r R2 R2 R8 which is ···

II 一 C一 ο- Ο

II • C a S — 0 0 II il • C a C — R1

I -c-o- R1

I -c-s-

O R3 II • C a Si —

O R5 -C-N-

Of -li-L R1 R3 •U- R2 R4 R1 R5i i One C—N—

For better X]-X2- to 14 314723 1287570 ο -Ο one - or R1

I —c — o — is better, to ο

II —c— ο — is better. -Υ^γ2- can be exemplified as follows. ]5 314723 1287570

16 314723 1287570

—N=B— —N=P- _N=C— •N=Si-

R 18 - B = P - a B = C - & B = Si - - P = C -

R 18

R 17 18 -P=Si—

R C=Si— R17 R18 wherein, from the viewpoint of the stability of the compound, N=C—•B=C—P=rC —

R t7

• C=Si—R17 R1S is better -Y5- can be exemplified as the following 17 314723 1287570 0 0 0

Η II II Ο - S - C - S - 8 - ιι Ο

It is better. In the formula (1), Μ is -YLY2-, and Υ1 and Ar2 are bonded to each other at the adjacent position of the aromatic ring carbon of Ar1, and Y2 and Ar1 are bonded to the adjacent position of the aromatic ring carbon of Ar2. In the formula (1), Μ is -Y^Y2-, and Y1 and X2 are preferably C(=0). In the combination of -Y^Y2- and -X^X2-, -Υ^Υ2- and -Χ^Χ2- in the repeating unit, the ortho positions of the aromatic ring are bonded to each other to become a C2 symmetric group, preferably - Υ^Υ2- is 0

II — 0 — C — — χΐχ, Μ — C — 〇 — is better. In the present invention, the polymer compound may have a trans group represented by the formula (1): 314723 1287570 The alkyl group may be any of a straight chain, a branched chain or a cyclic group, and the carbon number is usually from about 1 to about 20. Specific examples thereof include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclohexyl, heptyl, octyl, 2-ethylhexyl, Anthracenyl, fluorenyl, 3,7-didecyloctyl, lauryl, trifluoromethyl, pentafluoroethyl, perfluorobutyl, perfluorohexyl, perfluorooctyl, and the like. The alkoxy group may be any of a straight chain, a branched chain or a cyclic chain, and the carbon number is usually from about 1 to about 20. Specific examples thereof include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a third butoxy group, a pentyloxy group, a hexyloxy group, and a cyclohexyloxy group. Pentyloxy, octyloxy, 2-ethylhexyloxy, decyloxy, decyloxy, 3,7-dimethyloctyloxy, lauryloxy, trifluoromethoxy, pentafluoroethoxy , perfluorobutoxy, perfluorohexyloxy, perfluorooctyl, methoxymethoxy, 2-methoxyethoxy, and the like. The alkylthio group may be any of a straight chain, a branched chain or a cyclic chain, and the carbon number is usually from about 1 to about 20. Specific examples thereof include sulfoniumthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group, tert-butylthio group, pentylthio group, hexylthio group, cyclohexylthio group, Butylthio, octylthio, 2-ethylhexylthio, sulfonylthio, sulfonylthio, 3,7-dimethyloctylthio, laurylthio, trifluoromethylthio and the like. The alkylamino group may be any of a straight chain, a branched chain or a cyclic group, and may be a monoalkylamino group or a dialkylamino group, and the carbon number is usually from about 1 to about 40. Specific examples thereof include a methylamino group, a diammonium group, an ethylamino group, a diethylamino group, a propylamino group, a dipropylamino group, an isopropylamine group, a diisopropylamino group, a butylamino group, an isobutylamino group, and a third. Butyryl, pentylamino, hexylamino, cyclohexylamino, heptylamino, octylamine 20 314723 1287570, 2-ethylhexylamino, decylamino, decylamino, 3,7-dioxin Alkylamino group, laurylamine 'cyclopentylamino': cyclopentylamino, decylamino, cyclohexyl, pyrrolidinyl, piperidinyl, bistrifluoromethylamino and the like. The aryl group may have a substituent and the carbon number is usually from about 3 to about 6 Torr. Specific examples thereof include a phenyl group and a c 2 alkoxyphenyl group (Ci i2 represents a carbon number of i to 12. The same applies hereinafter.), a phenyl group, a naphthyl group, a 2-naphthyl group, and a five-gas group. Wait. The aryloxy group may have a substituent on the aromatic ring, and the carbon number is usually about 3 to about, and specifically, for example, an anthraceneoxy group, a C112 alkoxyphenoxy group, a Cm2 phenoxy group, a 1-naphthyloxy group, Naphthyloxy, pentafluorophenoxy, and the like. The arylthio group may have a substituent on the aromatic ring, and the carbon number is usually from about 3 to about 6 Å, and specifically, for example, a phenylthio group, a Cb12 alkoxyphenylthio group, a 19 1-12 alkylphenylthio group, 1-nathio, 2-naphthylthio, pentafluorophenylthio and the like. The arylamine group may have a substituent on the aromatic ring, and the carbon number is usually about 3 to 6 Å, and specific examples thereof include an anilino group, a diphenylamino group, a Cl.12 alkoxyanilide group, and a di(C!·) 2 group. An oxygenated phenyl)amino group, a bis(〇γΐ2anilino)amino group, a naphthylamino group, a 2-naphthylamino group, a pentafluoroaniline group, or the like. The aryl fluorenyl group may have a substituent, and the carbon number is usually from about 7 to 60, and specifically, for example, a phenyl-C 】 2 alkyl group, an alkoxy phenyl group 〇 112 alkyl group, a 1 -12 alkyl phenyl group - Cl -12 An alkyl group, a 1-naphthyl-cv12 alkyl group, a 2-naphthyl-CVi2 group, and the like. The arylalkoxy group may have a substituent, and the carbon number is usually from about 7 to 60', and specific examples thereof include a phenyl-Cb! 2 alkoxy group, (^12 oxiranyloxyalkyloxy C 2 alkylbenzene) Alkyl-c^2 alkoxy, bhnaphthyl-O^-12 alkoxy, 2 314723 21 1287570 naphthyl 12 alkoxy, etc. The arylalkylthio group may have a body group and the carbon number is usually 7 to 6 〇. Specific examples thereof include phenyl-C "2 alkylthio group, Cii2 alkoxyphenyl hydrazine 2 alkylthio group, C, -12 alkylphenyl-Cm 2 alkylthio group, and naphthyl group. An alkylthio group, a 2-naphthyl-Cm 2 alkylthio group, etc. The carbon number of the arylalkylamine group is usually from about 7 to 60, and specifically, for example, a phenyl-CV12 acrylamine group or a Cu oxyphenylene group 〇 112 amine group, CM2 alkylphenyl-Cm2 alkylamino group, bis(C^2 alkoxyphenylphosphonium) alkyl group, bis(C!•丨2 alkylphenyl-Cm2 alkyl) amine group, ^Naphthyl-Ci...alkylamino group, 2-Nylidene-C1-12 acrylamine group, etc. The carbon number of the brewing group is usually from about 2 to 20, and specifically, for example, ethyl hydrazino group, propyl fluorenyl group, butyl fluorenyl group, and the like are exemplified. Butyl, trimethyl ethane, phenyl fluorenyl, trifluoroethyl fluorenyl, pentafluorophenyl fluorenyl, etc. Usually, it is about 2 to 20, and specifically, for example, an ethoxy group, a propenyloxy group, a butoxy group, an isobutyloxy group, a trimethylacetoxy group, a benzoquinoneoxy group, a trifluoroacetonitrile group. Base, pentafluorobenzoyloxy, etc. The carbon number of the guanamine group is usually from about 2 to 20, and specifically, for example, amidino group, acetamino group, acrylamide group, butylammonium group, and benzophenone Amidino, trifluoroacetamido, pentafluorophenylamine, dimethylamino, diethylamine, dipropylamine, dibutylammonium, benzoylamino, Bis-trifluoroethylamine, bis-pentafluorobenzamide, amber succinimide, quinone imine, etc. The carbon number of the imine group is usually from about 2 to about 20, and specifically, for example, A compound which can be represented by the following structural formula: 22 314723 1287570

The substituted methadone group can be exemplified by: diterpene carbazide, triethyl fluorite, turmeric, tri-n-propyl fluorene, diisopropyl fluorite, and third Butyl methacrylate, dimethyl ketone, succinyl, succinyl, succinyl, trimethyl carbazide, triterpene, diphenylmethyl sulphate Anthracenyl group, tert-butyldiphenylalkylene group, dimethylphenylformamyl group, and the like. The substituted formazan group can be exemplified by: trimethyl sulfonyloxy, triethyl methoxyalkyloxy, tri-n-propylmethyl decyloxy, triisopropylmethyl decyloxy, and third butyl decane. Methyl dimethyl decyloxy, triphenyl methoxyalkyloxy, tri-p-xylylmethyl decyloxy, tribenzylmethyl decyloxy, diphenylmethyl methoxyalkyloxy, tert-butyl Phenyl nonyloxy, dimethylphenylformamoxy and the like. The substituted formylthio group may, for example, be a trimethyldecanethio group, a triethylmethylsulfanylthio group, a tri-n-propyldecylthio group, a triisopropyldecylthio group or a tert-butylmethylcarbonyl group. Methyl decylthio, triphenylmethanesulfanyl, tri-p-dimethylphenylmethanesulfanyl, trimethylsulfonylthio, diphenylmethylmethylsulfanyl, tert-butyldiphenyl A decylthio group, a dif 23 314723 1287570 phenyl phenyl sulfenyl group, and the like. The substituted decylamine group can be exemplified by, for example, trimethylmethyl sulphate, triethyl decylamino, tri-n-propylmethyl decylamino, triisopropylmethyl decylamino, and tert-butyl fluorene. a decyl dimethyl dimethyl decylamino group, a triphenyl sulfonium amine group, a tri-p-dimethylphenyl decylamino group, a tri-T-methyl carbaryl amine group, a diphenyl fluorenyl decylamino group, Tertiary butyl diphenyl decylamino group, triterpene phenyl carbamoylamino group, bis(trimethylmethyl decyl) amine group, bis(triethylmethyl decyl) amine group, two (three positive) Propylmethylalkyl)amine, bis(triisopropyldecyl)amino, bis(t-butyldecyldimethyldimethylalkyl)amine, bis(triphenyldecyl) Amino, bis(tri-p-nonylphenyl fluorenyl)amino, bis(tribenzylmethylindenyl)amine, bis(diphenylmethylformamidinyl)amine, bis(t-butyl Diphenylalkylalkyl)amine, bis(dimethylphenyl)alkylamine, and the like. The 1-membered heterocyclic group means the atomic group remaining after removing one hydrogen atom from the heterocyclic compound, and the carbon number is usually from about 4 to 60, and specifically, for example, a thiol group or a Cm alkyl thiol group. , pyrrolyl, furyl, pyridyl, alkylpyridyl, imidazolyl, pyrazolyl, σ sylylene, thiosaltyl, thiadiazide and the like. φ π 丞, triazolyl, 噚, etc. can be bonded to Arl or A by means of an ether bond, a thioether bond, an alkyl group, an amine group, an alkenyl group, an alkynyl group or the like. The aryl group in the ethynyl group can be exemplified by the same. The south molecular compound of the present invention has two or more kinds of complex units with the above aryl group. The polymer compound of the present invention may contain an inverse fluorination-free property or a charge-transfer 314723 24 1287570 excipient group having a benzene ring, a condensed ring, an independent benzene ring or a condensed ring 2 as shown in the formula (1). The bond is bonded directly or via a bond such as a vinylidene group, and is usually a carbon number of 6 to 60, preferably 6 to 20, and is exemplified by a phenyl group (for example, the following formula (26)), Naiji Base (the following formula (27)), a thiol group (the following formula (28)), a stretched phenyl group (the following formula (29)), a diphenyl group (the following formula (3)), condensation A cyclic compound group (the following formula (3 1)) or the like. There may be a substituent on the extended aryl group. The substituent may, for example, be a hydrazine atom, an alkyl group, an alkoxy group, an alkylthio group, an alkylamino group, an aryl group, an aryloxy group, an arylthio group, an arylamino group, an aralkyl group or an arylalkoxy group. Sulfate, aryl, amine, s, s, s, s, s, s, s, s, s, s, s, s, s, s, s, s, s, s, s, s, s An alkenyl group, an arylethynyl group or a cyano group, and the carbon number of the extended aryl group does not include the carbon number of the substituent. (26)

(2 7) 26 314723 1287570

(2 8) ~O^- ~o~^ ~o ~^ b^-q ^-p (2 9)

In the present invention, the divalent heterocyclic group means the meaning of the remaining atomic group after removing two hydrogen atoms from the heterocyclic compound, and the carbon number is usually from 4 to 60, 27 314723 !287570 to 4 to 20 carbon Among them, a heterocyclic group is preferred. Further, the heterocyclic group may have a substituent, and the carbon number of the substituent is not included. In the case of an organic compound having a cyclic structure, the element constituting the ring contains not only carbon but also a hetero atom such as nitrogen, phosphorus, butterfly, orthodontic or anthracene in the ring. The heterocyclic group of 2 Å can be exemplified by the following: a hetero atom of a fluorene-containing divalent heterocyclic group; for example, a pyridinediyl group (the following formula (32)), a diaza A phenyl group (the following formula (33), a quinolinediyl group (the following formula (34)), a quinoxalinediyl group (the following formula (35)), and an acridinediyl group (the following formula (36)) ^bibipyridinediyl (the following formula (37)), phenanthrolinediyl (the following formula (38)), etc. A group containing a hetero atom such as ruthenium, nitrogen, oxygen, sulfur, or selenium and having a ruthenium structure ( The following formula (39)): The 5-membered ring heterocyclic group containing a hetero atom such as hydrazine, nitrogen, oxygen, sulfur or selenium can be exemplified by the following formula (40): hydrazine, nitrogen, oxygen, sulfur, The 5-membered ring condensed heterocyclic group of a hetero atom such as a code can be exemplified by: (the following formula (41)), stupid thiadiazole-4,7-diyl or benzophenanthridine β-spin-4,7- A dibasic ring heterocyclic group containing a hetero atom such as sulfur and bonded at the position of the hetero atom to form a dimer or oligomer, and is exemplified as: (Expression (42) below) a 5-membered heterocyclic group containing a hetero atom such as a hydrazine, a nitrogen, an oxygen, a sulfur or a hydrazine, and a group bonded to a phenyl group at the alpha position of the hetero atom: It can be exemplified (the following formula (43)). (3 2) 28 314723 1287570 (3 3) δτ ^ 0 8 ^ . (3 4)

(3 6) 29 314723 1287570 (3 7)

(4 0) 30 314723 1287570

In ja:-

(4 1)

^S!r ^ (4 2)

(43) wherein R' independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkylamino group, an aryl group, an aryloxy group, an arylthio group, an arylamine group, or an aryl group. An alkoxy group, an aryl I thiol group, an arylamine group, a methoxy group, a decyl group, an aralkenyl group, an aryl group, an i-valent heterocyclic group or a cyano group. R" independently represents an alkyl group, an aryl group, an aralkyl group, a substituted formyl group, an acid group, or a monovalent heterocyclic group. 314723 3] 1287570 Furthermore, a divalent heterocyclic group is also For example, a trivalent luminescent complex compound or the like may be contained, and examples thereof include a divalent metal complex compound exemplified below.

314723 1287570

The polymer compound of the present invention can contain a repeating unit other than the above (1), and is preferable in terms of luminous efficiency, and may be an anti- ^* 一稷稷 shown by the following formula (7). 33 314723 128757〇(7) -Ar4 + N~Ar5 + r33 wherein Ar4 and Ar5 are independent and Ar4 is also s aryl or divalent heterocyclic, and argon can be bonded to each other to form Base, ^ %. Also, R33 represents an alkyl group,

The monovalent heterocyclic group may be a group represented by the following formula (9), or a group represented by the formula (9). g is a number of 1 to 4 (8) Λ ... wherein Ar6 is an exoaryl or a divalent privilege, 浐a ^ ^, which is a ring group. R34 represents a hydrogen atom 70 group, a square group, a monovalent heterocyclic group, and ginseng. Or may be represented by the following formula (9); soil Z3 represents -CR40 = CR41- or -Cs "jin, R4G and R41 are respectively independent ir" atom, alkyl, aryl, u J independent and 2 integer Heart base or cyano group. U 0j

Ar7

N

Ar8 R42 (9) R43 where 'Ar and Ar8 will be divided into I*

^ 42 The knife is independent of the aryl or the divalent JS base. R represents a hydrogen atom, an alkyl group, a aryl group, a tetra- or a monovalent heterocyclic group. Further, R ^ represents an alkyl group, an aryl group or a valence of '1 Å < _ % group. i is a meal of 1 to 4. The g w of the formula (7) can be dried. Further, a preferred specific example of #π', and the latter may be exemplified as follows, and the substituent may have a substituent on the acyclic ring or the heterocyclic group. 314723 34 1287570

The number average molecular weight of the polymer compound of the present invention is 10 to 10 8 in terms of polystyrene for 35 314723 1287570. The total number of repeated constructions may vary from one to another, from the viewpoint of film formation, and the total number of repeated structures is preferably from 5 to 10,000, preferably from 10 to 10,000, and from 20 to 10,000. Up to 50000 is the best. The polymer compound of the present invention may be a random copolymer, a block copolymer or a graft copolymer, or a polymer having such an intermediate structure, and a block random copolymer. In order to obtain a fluorene molecular compound having a high quantum yield of fluorescence, a random copolymer having a ruthenium or a relatively complete y? copolymer of a block or graft copolymer is preferred. There are more than three pieces of information on the main key for the branch and the end part is the same. Female 〇 〇 Our shape or dendrimer is also included. The unit of the yoke of the polymer compound of the present invention is connected to the unit of the yoke, or the structure of the repeating unit = ' can be a non-co-connected repeating unit, for example: -^, yoke #彳刀. If you don't do the following, you will be given a postal combination with the singularity of the squad, and the following ones. Here, the R-based hydrogen atom, the aryl group of 60 on the carbon number, and the group selected from the group consisting of carbon number 4 to ana 6 to the heterocyclic group of A-Ben 〇 6〇, and Ar The table is not the inverse of the hydrocarbons of 6 to 6 石. T 314723 36 1287570

At the end of the polymer compound of the present invention, 眭 B, /, the activity of the combination is substantially ruined. Second, the luminescent property or the durable life of the component is lowered to protect the stability of the disease. It is preferable to have a bond with the main chain of the main chain 4::, for example, a structure in which a bond is bonded via a carbon-carbon bond, a square group or a heterocyclic group. : 'Because the light emission from the film is utilized, it is preferred that the polymer compound of the present invention has a fluorescent state in a solid state. The excellent solvent of the polymer compound of the present invention may, for example, be: methylene chloride, dioxane, tetrahydrofuran, methyl bromide, xylene, 13 5-dimercaptobenzene, tetrahydronaphthalene or decalin, n-Butylbenzene and the like. Although it differs depending on the structure or molecular weight of the high molecular compound, it is usually possible to dissolve 0. 1 weight 〇/〇 or more in these solvents. The method of producing the polymer compound of the present invention will be described. The polymer compound of the present invention can be produced by using a compound represented by the following formula (丨〇) 37 314723 1287570 as a raw material and condensed and polymerized X1. X2 D1--Ar1

At2. -D2 (10) Μ (wherein, Ar1, Ar2, χΐ, .n2 v X and M are the same as formula (1). D1 and D respectively represent _ 素 atom, ^ 趟 ^ ^ alkyl sulfonic acid Salt, aryl sulfonate borate, fluorenylmethyl, fluorenyl, sulfhydryl methyl, monodentate methyl, boric acid, formazan, cyanomethyl or Base.) Here, the base is a certain sputum - * The soil is not as good as: methane sulfonate, ethane sulfonate, trifluoromethanesulfonate - Liyi - Sifangji continued S The salt base is not particularly limited as follows: a benzenesulfonate group, a p-benzoate, a ^^^--, a soil, etc., and an arylalkylsulfonate group can be exemplified by a T-sulfonate group or the like. The borate group can be exemplified by a group represented by the following formula. OMe OEt a &lt; —B, OMe OEt

The hydrazine methyl group is not as good as the group represented by the following formula. CH2SPh2X (wherein x represents a halogen atom.) The town methyl group is exemplified by a group represented by the following formula.

-CH2PphsX (wherein, X represents a halogen atom.) 314723 38 1287570 The rhein methyl group can be exemplified by a group represented by the following formula. -CH2PO(OR,,,) 2 (wherein R&quot;' represents an alkyl group, an aryl group or an aryl group.) The monohalogenated fluorenyl group can be exemplified by a fluoromethyl group, a chloromethyl group, a bromomethyl group or an iodonium group. base. The method of condensation polymerization has a vinyl group in the main chain, and other monomers may be used as needed, for example, a polymerization by a Wittig reaction between a compound having an aldehyde group and a compound having a sulphate group. [2] Polymerization by a reaction of a compound having an acid group and a squara base group, by a polymerization of a Heck reaction between a compound having an ethyl group and a compound having a γ atom [4] Polymerization by a gram reaction of a compound having a vinyl group and a sulfonium atom, [5] by a compound having an aldehyde group, a compound of a fluorenylphosphonate group, Ouna. Öss. Polymerization of the 〇rner-WadsW〇rth-Emmons) method, [6] by the combination of the enamel-Russian method of a compound having a sulfonate group and a pyridylphosphonate group, m A de-massing hydrogen method of two or more compounds of a functionalized methyl group: polycondensation, polycondensation of a sulfonium salt decomposition method of a compound having two or more sulfonium groups, [9] by blood of a compound having an aldehyde group There is a combination of B, Fen, and acetonitrile. ♦ The method of finding the gram of the Fenergael reaction of the substance, “11*1 burial from the eye (4) (10) 聚合 a method of polymerization of the McMurry reaction of the compound of the cleavage, etc. (1) to [11] The polymerization is shown as follows: 314723 39 1287570 (1) 0HC-Ar-CH0 + X: Ph3P+H2C-Ar*-CH2P+Ph3 χ-test / -^ —[—Ar-------- ---------------Ar1, 〔2〕 OHC——Ar——CH2P+Ph3 X*

Ar-:

[3] Test /

Ar-—....... + Br-Ar'-Br-► —hAr

Ar·

(4) Br-Ar base -! Palladium catalyst

Ar-- n 〔5〕 40 314723 1287570 OHC-Ar-CHO + (R0)2(0)PH2C—Ar· CH2P(0)(0R)2 fAr :-Ar'

n 〔6〕 OHC-Ar-CH2P(〇)(〇R)2

n

[9] OHC-Ar-CHO + MCCH2—Ar'· -ch2cn test ten r_

[10] Inspection OHC - Ar-CH2CN -

n 41 314723 [11] 1287570 〇hc~a卜CH0 —_ Further, in the method for producing a polymer compound of the present invention, the case where the vinyl group does not have a vinyl group in the main chain can be exemplified by [12] by Suzuki ( Suzuki) a method of conducting polymerization by coupling reaction, [13] a method of performing polymerization by a Grignard reaction, [14] a method of polymerizing by a Ni(〇)(nickel oxide) catalyst, [ 15] A method of oxidizing polymerization by means of an oxidizing agent such as FeCl3 (evaporized iron), an oxidative polymerization method of an electrochemical type, or a method of decomposing an intermediate polymer having an appropriate leaving group, [12] to [16] The polymerization method is as follows. [12] °

Br-

Ar-Br (RO)2B-Ar'——B(OR)2 R is a hydrogen atom, alkyl catalyst test

[13] Nickel catalyst

Br--Ar-MgBr [14] [15]

R

Y is S, NH

Br-Ar-Br

Oxidative polymerization

n 3]4723 42 [16] 1287570

ROCO 〇COR

Thermal decomposition

R, because of the ease of structural control, it is preferred to carry out polymerization by reaction, polymerization by gram reaction, polymerization by Ona-Russian, Emmon method, by Kneif The polymerization of the Nagel reaction and the method of carrying out the polymerization by the coupling reaction, and the method of polymerizing by the Ni(0) catalyst by the Grignard reaction. Further, from the viewpoints of the convenience of the repulsion-acquisition and the polymerization reaction, it is preferred to carry out the polymerization by a method of "reaction: polymerization, and polymerization by a Grignard reaction, by Ni (〇 a method of performing polymerization by using a catalyst. When the polymer compound of the present invention is used as a polymer, it is produced by the purity of the polymer compound, and the above-mentioned separation operation is carried out in a sufficient manner. , ' Staying = Fully remove unreacted monomers, by-products, catalyst residues, etc. 4 %: The conditions are sufficient to remove the remaining solvent, that is, the shading and the high T-substrate deterioration See 'to dry in an inert gas' is preferred. The drying of the ancient heat and the deterioration of the temperature is not a good result. The polymer compound of η Ming can be used as an active component of a light-emitting material to be used as a charge transporting material, an organic semiconductor material, or as a conductive material by f (dGping). The eight substances: the medium-eight-night/night-crystalline polymer compound means that the high-molecular molecule exhibits a liquid crystal phase. The liquid crystal phase can be confirmed by polarized light 314723 43 1287570 颏u mirror, differential scanning calorimetry, calender diffraction measurement, etc., and compounds having liquid crystallinity are known. Raw or aerated anisotropy. (Synthetic metal (Synthetic

Metals) U9, (2001) p. 537) In terms of its orientation, it can be used as a directional method for liquid crystals, such as "Basic and Application of Liquid Crystals" (Mr. Matsumoto Masahiro, Kakuda City) Co-authored 'Industrial Survey, published in 1991, Chapter 5, "Structure and Physical Properties of Strong Dielectric Liquid Crystals" (Fukuda Tatsuo, Takenaka Hideo, published by Grosvenor, 1990) Chapter 7, "Liquid Crystals" The methods described in Volume 3/Zhang (1999), pages 3 to 16, etc. Among them, the wiping method, the photo-alignment method, the shear stress applying method or the lift coating method are simple and useful in the material orientation method and are easy to use. The t-wiping method is a method of gently wiping the surface of a substrate with a cloth or the like. The substrate for glass or polymer film can be used to wipe the substrate for the substrate, and gauze or cloth such as polyester, cotton, nylon or enamel can be used. In addition, if an orientation film is formed on the substrate, it can be more ancient--P". Here, the alignment film may, for example, be polyimine, polyamine, r VA (vinyl alcohol), polyester, nylon or the like, and a commercially available alignment film for liquid crystal may also be used by Tian. The crepe film can be formed by spin coating or flexographic printing, and the cloth to be used is wiped, and the gusset is appropriately selected for the film. The UW sand Γ method is a method of forming an orientation film on a substrate, and illuminating or irradiating the uv light by polarized "outer line" light, and has a directional function. The oriented film can be exemplified by: Sub-"melamine, poly 314723 44 1287570 vinyl cinnamate, and commercially available alignment film for liquid crystal can also be used. In the wiping method or photo-alignment method, interposed between the substrates subjected to the above-mentioned processing The oriented polymer material can be oriented. In this case, the substrate must be used as a material to achieve the liquid crystal phase or the isophase n temperature setting, and the polymer material can be placed before the substrate; Only the polymer material may be applied to the substrate subjected to the orientation treatment. The coating of the polymer may be performed by placing the polymer on the substrate and setting it to a Tg (glass transition temperature) or higher. The temperature of the liquid crystal phase or the isotropic phase is applied in one direction by a rod or the like, or a solution dissolved in an organic solvent is prepared, and it can be carried out by a spin coating method or a flexographic printing method. Variable stress application method refers to placement on a substrate The polymer material 枓 is placed on another substrate. The method of shifting the substrate-to-direction at a temperature that can be a liquid crystal phase or an isotropic phase. In this case, the substrate is used in a method of performing a wipe or a light directing method. The substrate for the orientation treatment described above, that is, the y garment has a higher degree of susceptibility. The substrate can be made of glass or a polymer film, or a metal roller can be used as a substrate for the movement of the stress. Refers to the method of immersing the substrate in a polymer solution, and then using the organic solution as a polymer solution, or the lifting degree of the substrate is not particularly limited, and can be selected and adjusted according to the orientation degree of the polymer. Material ^ The polymer compound of the present invention is used as a light-emitting of a polymer LED to achieve the effect of its purity on the luminescence property, and the first body is obtained by distillation. , sublimation purification, recrystallization, etc., 'polymerization after coating, and preferably, after synthesis, purification treatment according to re-precipitation 45 314723 1287570 precipitation purification, chromatography separation, etc. &gt;, due to utilization from the film Illumination or For the sake of light, the knives of the present invention are preferably those which have fluorescence or phosphorescence in a solid state. The excellent solvent for the polymer compound of the invention can be exemplified by chloroform, methane, dichloroethane, tetrahydrofuran, Toluene, xylene, monomethyl, tetrahydronaphthalene, decalin, n-butylbenzene, etc. Although it differs depending on the structure or molecular weight of the macromolecular substance, it can usually be dissolved in these solvents. 1% by weight or more. Next, the polymer LED of the present invention will be described. The molecular LED of the present invention is characterized in that it has a light-emitting layer between electrodes made of an anode and a cathode, and the light-emitting layer has the present invention. Further, the polymer LED of the present invention includes a polymer LED in which an electron transport layer is provided between a cathode and a light-emitting layer, and a hole transport layer is provided between the anode and the light-emitting layer. The polymer LED is a polymer LED in which an electron transport layer is provided between a cathode and a light-emitting layer, and a hole transport layer is provided between the anode and the light-emitting layer. In the polymer LED of the present invention, at least one of the electrodes and the light-emitting layer is provided with a return molecular LED adjacent to the electrode and containing a layer of a conductive polymer; at least one of the electrodes and the light-emitting layer is also A polymer LED having an insulating layer adjacent to the electrode and having a film thickness of 2 nm or less is provided. Specifically, configurations such as the following... to d) can be exemplified. a) anode / luminescent layer / cathode 46 314723 1287570 b) anode / hole transport layer / luminescent layer / cathode C) anode / luminescent layer / electron transport layer / cathode d) anode / hole transport layer / luminescent layer / electron transport Layer/cathode (herein, the / mark indicates that each layer is adjacent to each other and is laminated.) / Here, the light-emitting layer refers to a layer having a light-emitting function, and the hole-transporter refers to a transfer hole. The layer of function, the layer of electron transport refers to the layer that has the function of transmitting electrons. In addition, it is known that the electron transport layer and the hole transport layer are slightly charge transport layers. The light-emitting layer, the hole transport layer, and the electron transport layer may each be independently a layer or more. Further, among the charge transport layers disposed adjacent to the electrodes, and having an effect of improving charge implantation efficiency from the electrodes and having a driving voltage for lowering the elements, the charge implant layer is generally referred to as a charge implant layer. Into the implant layer). Furthermore, in order to improve the adhesion between the electrodes or the improvement of the charge from the electrodes, the aforementioned charge implantation may be provided adjacent to the electrodes: or &amp; an insulating layer having a thickness of 2 Å or less In order to improve the adhesion of the interface, it is also possible to insert a thin buffer layer at the interface of the charge transport layer or the light-emitting layer. Regarding the order or the number of layers, and the thickness of each layer, it can be appropriately used under the "efficiency or component durability life. In the present invention, a charge implant layer (electron implant layer, hole implant g) spoon π knife is provided. The LED can be exemplified by a tt&quot;3 molecular LED which is connected to the cathode and is provided with electricity 314723 47 1287570, and a 鬲 molecular LED which is adjacent to the anode and is provided with a charge of eight shields. For example, specifically: The following structures e) to p). 岣 anode / charge implant layer / luminescent layer / cathode 0 anode / luminescent layer / charge implant layer / cathode g) anode / charge implant layer / luminescent layer / charge implant layer /cathode h) anode / charge implant layer / hole transport layer / light-emitting layer / cathode 1) anode / hole transport layer / light-emitting layer / charge implant layer / cathode implant layer / hole transport layer / light-emitting layer / Charge implant layer/cathode k) % pole/electricity implant layer/light-emitting layer/charge transport layer/cathode l) anode/light-emitting layer/electron transport layer/charge implant layer/cathode-in layer/light-emitting layer state.) Yangshuo /:: two layers / hole transport layer / light emitting layer / charge transport layer / cathode P = two layers / light emitting layer / electron transport layer / charge implant layer / Cathode = Electrode, Implant Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Charge Implant Layer / Cathode Electric Lamp Charge Implant Layer Specific examples can be exemplified by a layer containing a conductive polymer, I is disposed between the anode and the hole transporting layer and contains a material having a value of the intermediate value of the hole transporting material contained in the hole transporting layer (P〇tentiaI); a layer of a material between the cathode virtual electric layer and containing an electron affinity having a value intermediate between the cathode material and the second transport material contained in the electron transport layer. The electron such as the charge implant layer contains a conductive polymer material. The electrical conductivity of the electrical polymer is preferably 1 〇.5 S/cm or more i 〇 3 s / c ^ ¥ 314723 48 1287570 = when the leakage current between the illuminating pixels is preferably below. More preferably 10 s/cm or more 1〇ls/cr 5s/cmVi ^ ^ ^ ^ ^ ^ (d_) Suitable ions (10) &quot;&quot; See below for the type of ion doped in the conductive polymer, such as The electrons are dry, such as the hole-implanted layer, which is an anion, and the example of the secondary acid-ion diode is exemplified. · Examples of polyphenylenes can be exemplified by sub- and camphor-reduced acid ions, and cations and the like are inferior: the film thickness of the ion, the nano-ion, the unloading ion, and the tetrabutyl-doped charge-implanting layer can be, for example, one. 〇〇 is 2nm to 5〇nm. Weight 1 soil = material of the charge-implanted layer, the appropriate choice from the electrode or the relationship between the material and the material is the biological, take ^ can be as good as the polyaniline and its extension 1 And its derivatives, its derivatives and derivatives, polyphenylenes and JL and "Ho bio, poly-extension thiophene and its derivatives, polyquinoxaline: derivatives, polyquinoxalines and their derivatives The material, the conductive polymer such as a polymer having an amine structure, a metal phthalocyanine (Bronze Moon Temple), carbon, or the like is contained in the main chain or the branch. —Insulation of a film thickness of 2 or less has a function of facilitating charge implantation. The material of the insulating layer may be, for example, a metal fluoride, an emulsifier, or an organic insulating material. The polymer LED provided with the insulating layer having a thickness of two or less is provided with a polymer led layer which is provided adjacent to the cathode and has an insulating layer of 314723 49 1287570 and a thickness of 2 nm or less, and is provided adjacent to the anode and provided with a film. A polymer led of an insulating layer having a thickness of 2 nm or less. Specifically, for example, the following configurations of q) to ab) are exemplified. q) Insulation layer/light-emitting layer/cathode thickness: 2 nm or less, anode layer/light-emitting layer, film thickness: 2 nm or less, insulating layer, cathode, anode, film thickness: 2 nm or less, insulating layer, light-emitting layer, film thickness, 2 nm or less Insulation layer/cathode t) anode/film thickness 2 nm or less insulating layer/hole transport layer/light emitting layer/thin pole phantom anode/hole transport layer/light emitting layer/insulating electrode with film thickness of 2 nm or less v) anode/film thickness Insulation layer below 2nm / singular transmission layer / under the insulation layer / cathode film 厗 7 pole / film thickness 2 below the insulation layer / luminescent layer / electron transport layer / cathode anode / 3⁄4 optical layer / electron transport layer / Insulation layer having a film thickness of 2 Å or less / cathode anode / insulating layer having a film thickness of 2 nm or less (four) layer / electron transport layer / insulating layer having a film thickness of 2 nm or less / cathode z) anode / film thickness 2 nm transmission layer / underlying insulating layer / hole transport layer / light-emitting layer / electron aa) anode / hole transport layer / hair insulating layer / cathode light layer / electron transport layer / film thickness of 2nm or less thick insulation layer / hole transport layer (four) 曰 film thickness The thickness of the light-emitting layer in the LED of the insulating layer/cathode of 2 nm or less is driven by the power plant and the hair Efficiency ",, mode field value can be selected, but for example, from ^ 314,723,501,287,570 preferably from 2nm to 500 nm, more preferably 511,111 to 2〇〇nm. In the polymer LED of the present invention, a light-emitting material other than the above polymer compound may be used in combination with the light-emitting layer. Further, in the polymer LED of the present invention, the light-emitting layer ’ containing the light-emitting material other than the polymer phosphor may be laminated to contain the polymer fluorescent luminescent layer. The luminescent material can be used by a well-known person. Among the low molecular compounds, for example, a naphthalene derivative, an anthracene or a derivative thereof, perylene or a derivative thereof, a p〇lymethine system, a xanthene coumarin, or the like can be used. a pigment, a cyanine or the like, a metal complex of hydroxyquinoline or a derivative thereof, an aromatic amine, tetraphenylcyclopentadiene or a derivative thereof, or tetraphenylbutane Aene or a derivative thereof or the like. Specifically, for example, a person who is described in Japanese Patent Laid-Open No. SHO 57-5i78i, No. 59-194393, and the like can be used. The method of film formation of the light-emitting layer is not established, but a method of forming a film from a solution can be exemplified. From the film forming method of the solution, for example, a spin coating method, a washing molding method, a micro gravure coating method, a gravure coating method, a strip coating method, a light coating method, a wire rod coating method, or the like can be used. Dip coating method, nozzle spray coating method, screen printing method, flexographic printing method, offset printing method, and inkjet printing method coating method. When the polymer LED of the present invention has a hole transporting layer, the hole transporting material used may be exemplified by, for example, a polyethylene-based scent or its street organism, a poly-stone or a derivative thereof, in a branch or a main a polyoxo sulphate derivative y having an aromatic amine in the chain, a porphyrin derivative, an arylamine derivative, or even a derivative, a triphenyldiamine derivative, a polyaniline or a derivative thereof, a polythiophene Or its 314723 51 1287570 Ho, polypyrrole or its derivatives, poly(p-phenylene vinyl) or its derivatives, or poly(2,5-threhenylthione) or its derivatives. Or a polyoxazolidine or a derivative thereof, a polyfluorene or a living organism, a polyoxyalkylene compound having an aromatic amine compound group in a branched or main chain, polyaniline or the like A polymer hole transporting material such as a derivative, a polythiophene or a derivative thereof, a poly(p-(ethylene)) or a derivative thereof, or a poly(2,5-thienylthione) or a derivative thereof is preferred. , further comprising a polyethylene core or a derivative thereof, poly(tetra) or a derivative thereof, having an aromatic amine in a branch or a main chain The polyoxyalkylene derivative is preferred, and the low molecular hole transport material is distinguished by the use of a polymer binder. It can be derived from, for example, a vinyl monomer by polyvinylcarbazole or its derivative. The compound, the cationic polymerization or the radical polymerization to obtain a cut or a derivative thereof can be exemplified by, for example, Chemical Review Journal d, Vol. 89, p. 1359, 0989, and the compounds described in the British Patent GB 23 00 196. . The synthesis method can also use these methods, but it is most suitable for the Kipping method. Acupoint transmission = reduction or what its biology, due to the absence of vacancies in the structure of the stone-like oxygen-burning skeleton, the structure of the material in the branch or the main chain is a low-twist hole. The above can be exemplified by the following: in the branched or main chain /, the hole transporting aromatic amine. The film-forming method of the 28-transport layer is not particularly limited. In terms of the eight-transport material, a method of forming a mixture of the glazed sage and the scorpion splicing agent can be exemplified. In addition, in the high-scoring M«J i ^ 八八 transmission materials, J cases are not formed by a solution. 314723 52 1287570 k &gt; The film formed by the solution of the grain is used for the film, and the ^^ is used more, as long as it is capable of dissolving the hole transfer material, it is not particularly limited. ^ m 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 疋 岭 岭 疋 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 岭 气 岭 气 气 气Aromatic furnace, Hechenggong, 合, _, methyl ethyl ketone, etc., solvent, ethyl acetate, B &amp; L, S, ethyl fibrin acetate Ester-based solvent. The film formation method from the solution can be used: spin coating from solution, % 'main molding method, gravure coating method, gravure coating method, strip coating method' roll coating method, steel wire Coating methods such as a bar coating method, a dip coating method, a spray coating 2, a die printing method, a flexographic printing method, an offset printing method, and inkjet printing. It is also suitable for those who do not excessively hinder the charge transfer, and the absorption of visible light is not too strong. The polymer adhesive d can be as follows: polycarbonate, polyacrylate, polydecyl acrylate, water methyl methacrylate, styrene, polyvinyl chloride, polyoxane, a two-hole transport layer The optimum value of the film thickness varies depending on the materials used. ^ It is necessary to select the appropriate value according to the driving voltage and luminous efficiency. Ten 隹S, two or less, should not cause pinhole thickness. If it is too thick, then The driving voltage of the component is increased; ^ h ^ and . Therefore, the film thickness of the hole transporting layer is, for example, preferably from 1 nm to 1 JJL Yj [\ 5 P / ^ nm to 500 nm, more preferably from 5 nm to 200 nm. The inventive polymer LED has a white-headed rabbit transport material, and can be exemplified by, for example, an oxadiazole derivative 蒽醍53 314723 1287570, or a derivative thereof, a benzoquinone or a derivative thereof, a naphthoquinone or a derivative thereof, and an awakening Or a derivative thereof, tetracyanoquinodimethane or a derivative thereof, an anthrone derivative, monophenyldicyanoethylene or a derivative thereof, a diphenanthrene derivative, or 8-quinoquine or a derivative thereof a metal coordination compound, polyquinoline or a derivative thereof, polyquinoxaline or a derivative thereof, polyfluorene or a derivative thereof. Wherein, the oxadiazole derivative, benzoquinone or a derivative thereof, hydrazine or a derivative thereof, or a metal coordination compound of 8-hydroxyquinoline or a derivative thereof, polyquinoline or a derivative thereof, polypyre Or a quinone or a derivative thereof, polyfluorene or a derivative thereof, preferably 2-(4-biphenyl)-5-(4-t-butylphenyl), oxazole, benzoquinone, enamine , quinolinol phenol) aluminum, polyquinoline is more preferred. The film formation method of the electron transport layer is not particularly limited, but in the low molecular electron transport material, a vacuum deposition method in which n is terminated by (4), or a method in which a film is formed from a solution or a molten state can be exemplified. The polymer material can be exemplified by a method of forming a film from a solution or a molten state. When forming a film from a solution or a molten state, a mixture is used. J 1 幵 鬲 鬲 鬲 鬲 鬲 鬲 鬲 鬲 鬲 鬲 鬲 鬲 鬲 鬲 鬲 鬲 鬲 鬲 鬲 J J J J J J J J J J J J J J J J J J J J J J J J J J J J J J - an ether-based solvent such as lactine or dichloroethane, or an ether-based solvent such as a medium emulsion of 1:1; a toluene, a dimethyl group, etc., a hydrazine, a solvent, a methyl ethyl ketone, etc. A ketone-based solvent; a solution of a hydrocarbon in a solution of etaza: γτ> ·* 酉 、, an ester-based solvent such as ττ^ Τ-based fibrin acetate. G ® 欠丁! From the solution or molten state of the Tengshi* method spin coating strip coating pancreas method can be cast molding, micro gravure coating method, πη gravure coating method 31472, 54 !28757 Coating methods such as enamel, spray coating, inkjet printing, roll coating, wire rod coating, dip coating, screen printing, flexographic printing, offset printing, and the like. The polymer binder to be mixed is suitable for those who do not excessively hinder the charge transfer, and which does not absorb too much visible light. The polymer binder may, for example, be poly(N-vinylcarbazole), polyaniline or its derivative: polybenzaldehyde 2 derivative thereof, poly(p-phenylene vinylene) or a derivative thereof, poly ^'5-Extenient thiophene-extended ethylene) or its derivatives, polycarbonate, polyacrylic acid, hydrazine, polymethacrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, or Polyoxane and the like. ^ ^ The film thickness of the sub-transport layer is different depending on the material used. As long as the appropriate value is selected according to the driving voltage and the luminous efficiency, it is necessary to make the pinhole thickness, such as too thick, Then the driving power of the component is not suitable. Therefore, the film thickness of the electron transporting layer is, for example, preferably from 2 nm to 50 nm, and more preferably from 5 nm to 2 Å. The substrate of the π-molecule LED of the present invention is not particularly limited as long as it is formed into a layer in which an organic substance is formed, and examples thereof include glass, plastic, polymer film, and ruthenium substrate. In the case of an opaque substrate, the opposite electrode is preferably transparent or translucent. In the present invention, at least one of the electrodes made of the anode and the cathode is transparent or opaque, and the anode side is preferably transparent or translucent. The material of the anode may be a conductive metal oxide film, a translucent metal film or the like. Specifically, it can be used: indium oxide, oxidized, tin oxide, and 314723 55 1287570 f made of conductive glass made of indium, tin, oxide (ITO), indium, zinc, oxide, or the like of the composite. Membrane, etc., or gold, white, silver, or copper, preferably γ Τ μ ' / system, 0, indium, rhodium oxide, tin oxide. The production method can be mentioned: direct medium selection, + η two / special product method, sputtering method, ion plating method, plating method #. Further, the anode may be an organic transparent conductive film which is used for the amine or a derivative thereof, polythiophene or a living organism thereof. The film thickness of the electrode can be appropriately selected in consideration of light penetration and electrical conductivity. 'For example, it is 1 〇 nm to ～1 to 1 ,, and 20 to lAm is preferable, 50 nm to 5 〇〇 nm. For better. And 'on the anode, for easy charge-implantation of phthalocyanine derivatives, conductive ancient eight sons ☆; see 'can be set from V-electricity knives, carbon layer, compound or metal fluoride, organic genus Battle the following layers. The average film thickness of the H-bar material 枓4 is 2nm. The cathode material used in the polymer LED is the best. For example, calcium sharp, '钡, aluminum, antimony, vanadium, zinc, antimony, indium are used. Metals such as mirrors, etc., and two or more of them are infused into two, pin, one or more kinds of alloys, graphite or graphite with gold, silver, tin, copper, fission, titanium, J' or the like. Interlayer compounds, etc. Combination:, crane, tin, magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium &quot; can be used for gold, bell-alloy, chain-indium alloy, and slag alloy. Zhong-Minghe is a laminated structure of two or more layers. The film thickness of the cathode cathode can be determined, and the electrical conductivity can be considered, for example, i 〇 nm to i 〇 / / m, and it is preferable to select nm to 1 / m, and 314723 56 1287570 to 5 〇11„1 to 5〇〇nm4 is better. The cathode can be produced by vacuum-bonding the metal film to the layer which is thermocompression-bonded, and the layer between the organic layers can be placed at the cathode. The average film thickness of the compound or metal vapor, the ancient her layer, or the organic insulating material below the metal oxygen 2

After the use of the two cathodes, the agricultural patch protects the polymer LED (four) layer. In order to be able to use the polymer for long-term stability, the core protection component is preferably a protective layer and/or a protective cover. The protective layer can be used for the second/genus oxides such as the ancient octagonal compound and the metal-depleted compound, and the metal fluoride 35 boride temple. Further, a method in which a protective cover can be a glass plate or a plastic plate treated with a low water permeability on the surface, and the cover is placed on the element substrate by using a heat-effect resin or a photo-curable resin is applicable. When a sheet is used to maintain space, it is easy to prevent damage to the component. If an inert gas such as nitrogen or argon is enclosed in the space, the oxidation of the cathode can be prevented, such as 爯太兮. In the slab, the drying of the sputum, such as yttrium oxide, can be used to suppress damage to the components caused by moisture adsorbed during the manufacturing process. It is preferable to take measures of any one or more of them. Further, the charge transport layer and the light-emitting layer are provided between the electrodes formed of the anode and the cathode, and the charge transport layer may also contain the polymer LED of the polymer compound of the present invention. The polymer light-emitting device of the present invention can be used as a planar light source, a segment display device, a dot matrix display device, and a backlight of a liquid crystal display device. When the polymer LED of the present invention is used to obtain a planar light-emitting 57 314723 1287570, the planar anode and the cathode may be disposed to overlap each other. Further, in order to obtain a pattern-like luminescence, #: a method of arranging a mask having a pattern-like aperture in the front surface-like luminescence surface δ. Also, winter is not a hair. The organic layer of p is formed to be extremely thick to form a substantially non-luminous method, and any or both of the electrodes of the anode or the cathode are formed into a pattern to form a pattern according to any of the methods, and several The electrode ^ is independently configured to be 〇N/〇FF (on/off), and a display element of a segment type capable of displaying numbers or characters and simple marks can be obtained. Further, in order to create a matrix element, the anode and the cathode are formed in a stripe shape and arranged so as to be vertically intersectable. Partial color display and multi-color display can be realized by a method of separately applying a plurality of polymer phosphors having different luminescent colors, or a method using a color filter or a fluorescent conversion color filter. The dot matrix component can also be passively driven or combined with a TFT (thin film transistor) for active driving (3 such as "dr1Ving". These display components can be used as computers, televisions, mobile line terminals, mobile phones^ The display device of the car navigation system, the viewfinder of the video camera, etc. is used. The planar light-emitting element is a self-generated thin light type, and can be applied to a planar light source for backlight of a liquid crystal display device or as a planar shape. In addition, if a flexible substrate is used, it can also be used as a curved light source or a display device. '' Hereinafter, the present invention will be described in more detail, and ββ ^丨J 不贝施For example, the present invention is not limited by the examples. Here, the average molecular weight is a compound obtained by using tetrahydrofuran as a compound and a gel permeation 314723 58 1287570 polyphenyl chromatography (GPC). 1 The average molecular weight of ethylene conversion 〇 &lt; Synthesis of monomer 1 &gt; 8 and ^ bromo-3,7-dimercaptooctyl 22 lg, and potassium carbonate 6 〇 g in N, N- - A | Tiangu a, monomethylcarbamide 450g in 100 C The reaction was carried out for 28 hours. After cooling the @座, the reaction solution was allowed to stand, and the mixture was separated into two layers. Then, the upper layer was recovered, and the recovered solution was washed with water, and the washed solution was washed with water until it was washed. In the middle ~ τ note the horse. Then, after the oil layer is dried under reduced pressure, use the rubber tube column, station ^ & not king, hunting by mobile phase toluene / hexane: &quot;, unreacted i-al After the removal of the 4,7-dimethyl xinyuan and hanhuaic acid four-milk substitute, the dialkyloxy substituent is extracted from the mobile phase chloroform. The solvent is distilled off from the fractionated solution. After drying, it was dried under reduced pressure to obtain 6.5 g of a dialkoxide substitution. The resulting dialkoxy substitution, chemical shift from proton nucleus resonance spectroscopy (NMR) and hydroxyl groups at positions 2, 7 and 3, 8 The result of investigation on the reactivity between 1-bromo-3,7-didecyloctane is presumed to be 2,7-dihydroxy-3,8-bis(3,7-dimethyloctyloxyl)benzene. And pyran [5,4,3-cde][l]benzopyran-5,l〇-dione. The obtained chemical is referred to as monomer i. &lt;Synthesis of Polymer Compound 1&gt ; react monomer 1 with trifluoromethane orthoic anhydride The monomer 1 of the three gas methane sulfonate 0.59g, and 9,9-dioctyl-2,7·oxadicarboxylate 〇.37g, and potassium carbonate lg, dissolved in toluene 20g and ions After exchanging water in 2〇g, it was boiled in nitrogen to carry out nitrogen exchange in the system. Adding 0.02 g of the catalyst {Pd(pph3)4} to the solution was dissolved in nitrogen gas 314723 59 1287570 in advance and A solution of degassed toluene in 1 ml was stirred at room temperature for 10 minutes, and then reacted under a loot: for 5 hours. Here, the reaction was carried out in a nitrogen atmosphere. After the reaction solution was cooled, toluene was added, and the toluene layer was collected after liquid separation. The toluene solution was washed with 1 equivalent of hydrochloric acid, washed with 2% aqueous ammonia, and finally washed with ion-exchanged water. After the toluene solution was purified by passing through a column packed with alumina, the toluene solution was poured into methanol and subjected to precipitation purification. After the precipitate formed was recovered, it was dried under reduced pressure to give a crystal. This obtained polymer is referred to as a polymer compound i. The polymer compound i has a number average molecular weight of 2 〇 xW' in terms of polyethylene and a weight average molecular weight of 5.6 χ 1 〇 4. The following shows the structure of the repeating unit contained in the polymer compound 丨 estimated from the feed.

Example | Shi ΐ Divided into the compound 姊i... ^早&quot;m-A-anhydride reaction station &quot; II gas-burning stone vinegar vinegar 〇.63§ and 2,2,, 吼. After the determination of 氢 = hydrogen π 喃 ( (dehydration) in 3Gg, nitrogen nitrox, into (a) gas exchange. To the solution, bis(1,5-cyclooctanedipine) and &lt;(9)Qing (10) were added to obtain 5 g, and the mixture was heated at room temperature for a period of 2 minutes, and then heated at 314723 60 1287570 ° C for 3 hours. Here, the reaction was carried out in a nitrogen atmosphere. After cooling the reaction solution, a mixed solution of 25% ammonia water 10 ml/methanol 1 〇〇ml/ion exchanged water 200 ml was added, and the mixture was stirred for about 1 hour. The solution was allowed to stand at room temperature overnight and then filtered to recover the resulting precipitate. After the precipitate was dried, it was dissolved in toluene. After filtration to remove insolubles, the solution was purified by passing through a column packed with alumina. Next, the solution was poured into methanol and refined into a chamber. The precipitate formed was recovered, and: after washing with ethanol, the polymer G G2 was obtained. The obtained polymer is referred to as polymer compound 2. Sun Wei is divided into compounds

A 1 a -T ~ biguanide molecular weight J 4 · 5 χ 103, and the weight average molecular Jin Ding ^ knife miles is 7.2 Χ 1 〇 3. The structure of the repeating unit contained in the polymer compound 2 estimated from the contents is shown below. Outside the 'Using a polarizing microscope', the result of observing the surname s / ' of the polymer compound 2 under orthogonal polarized light ((10) SSnicol) is judged from its texture,

曰B confirm that the molecular compound 2 is a liquid 0

Example 3 &lt;Synthesis of Polymer Compound 3 The trifluoroanthracene pyroxantine obtained in Example 1 was changed.

ϋΟ | Early ugly 1 and difluoromethane fluorescein to obtain a single § 曰 0.63g and Ν, Ν-bis(4-bromophenyl)-Ν, Ν, _ 314723 61 1287570 bis (4-n-butyl Phenyl phenyldiamine oxime. 23g and 2,2, · 联二哦 bite 〇. 39g dissolved in tetrahydrofuran (dehydrated) 30g, stagnation in nitrogen, gas exchange in the sputum. Add bis (1,5-cyclooctane-diluted) nickel (O) {Ni(COD) 2} 0.7 g to the solution, stir at room temperature for 10 minutes, then raise the temperature, and react at 60 ° C for 3 hours. The reaction was carried out under a nitrogen atmosphere. After cooling the reaction solution, a mixed solution of 25% ammonia/1 〇〇ml/100 ml of ion-exchanged water was added and stirred for about 1 hour. After standing overnight, it was filtered to recover the precipitate formed. Then, the precipitate was dried and dissolved in toluene. After filtration to remove insolubles, the solution was purified by passing through a column packed with alumina. The solution was poured into methanol and purified by precipitation. The resulting precipitate was recovered, washed with methanol, and dried under reduced pressure to give a polymer G G 3 g. The polymer is called polymer compound 3. The average molecular weight of the polymer compound 3 in terms of polystyrene is 5·3χ1〇3, and the weight average molecular weight of the rabbit is 1〇14 刀. The following shows the structure of the 禝 口 / j j 高分子 高分子 314 314 高分子 高分子 高分子 高分子 高分子 314 314 314 314 314 314 314 314 314 314 314 314 314 314 314 314 314 314 314 314 314 314 314 314 314 314 314 314

Ο

C4H9 C4H9 complex Ife Example 4 &lt;Synthesis to Molecular Compound 4&gt; The monomer 1 obtained in Example 1 was reacted with trifluoromethanesulfonic anhydride to obtain a monomer 1 of trifluoromethanesulfonate 〇.25 g and 1,4- 0.66 g of dibromo-2,5-bis(3,7-dimethyloctyloxy)benzene and 2,2,-bipyridinium. 61 g were dissolved in tetrahydrofuran (dehydrated) 40 g, and boiled in nitrogen. , carry out nitrogen exchange in the system. Bis(1,5-cyclooctadiene)nickel (0){Ni(C0D)2} l.lg was added to the solution and allowed to react at room temperature for 24 hours. Here, the reaction was carried out under a nitrogen atmosphere. Next, a mixed solution of 25% ammonia water 10 ml/methanol 30 ml/ion exchanged water 60 ml was added to the reaction liquid, and the mixture was stirred for about 1 hour. This solution was allowed to stand at room temperature overnight and then filtered to recover the resulting precipitate. Then, the precipitate was dried and dissolved in toluene. Filter to remove insolubles. Next, the solution was washed with 1 equivalent of hydrochloric acid, and then separated, and then washed with about 63 314723 1287570 2.5% ammonia water, and the liquid layer was layered to form an ionic benzene layer. Next, the obtained toluene solution was poured into methanol, and the resulting precipitate was recovered by washing with water, and purified by precipitation with methanol and Qinzhin% _ 〇 ^. Compound 0. The polymer obtained is referred to as "polystyrene of the polymer compound 4". The structure of the polymer compound 4 estimated by the package is not the structure of the product.

κ冬 has changed the number of different dandans to 4.8 Χ and the average weight molecular weight is 7〇χ 1〇3. Bottom: Knife I/Example 5 &lt;Synthesis of Polymer Compound 5&gt; The monomer 1 obtained in Example 1 was reacted with trifluoromethanesulfonic anhydride to obtain a trifluoromethanesulfonate 〇.25 g of the monomer 1 and 0.72g of 3,7-dibromo-2,8-dioctyloxydibenzothiophene and 2,2,-bipyridinium. 55g dissolved in 40g of tetrahydro D-propan (dehydrated), after nitrogen Boiling in the middle, nitrogen exchange in the system. Bis(1,5-cyclooctadiene)nickel (〇) {Ni(COD) 2} 1.0 g was added to the solution, and the mixture was reacted at room temperature for 24 hours. Here, the reaction was carried out in a nitrogen atmosphere. 64 314723 1287570 Next, a mixed solution of 25% aqueous ammonia i〇mi/sterol 3〇mi/ion-exchanged water in 60 ml was added to the reaction mixture, and the mixture was stirred for about 1 hour. This solution was allowed to stand at room temperature overnight and then filtered to recover the resulting precipitate. Then, the precipitate was dried and dissolved in toluene. Filter to remove insolubles. Next, the solution was washed with 1 equivalent of hydrochloric acid and separated, and then washed with about 2.5% ammonia water to separate the solution, and then the toluene layer was washed with ion-exchanged water. Secondly, the patient's toluene solution was injected into the hyperthyroidism. The resulting precipitate was washed with methanol and dried under reduced pressure to give a polymer (0.05 g). This obtained polymer is referred to as polymer compound 5. The polymer compound 5 has a number average polystyrene conversion of UXW and a weight average molecular weight of 1 δ χΐ〇4. The following shows repeated iterations of the polymer compound 5 estimated from the contents. ^21^ι〇0

ο OPC&quot;. OC1

Example 6 &lt;Synthesis of Polymer Compound 6&gt; The reaction obtained by the reaction of fluorononanesulfonic anhydride was as follows: Monomer 1 obtained in Example 1 and 25 g of trifluoromethane sulphate and 3 in 314723 65 1287570. 7_二漠代_2,8_dioctyloxydibenzothiophene 〇.45gAN Dongshuang(4-Molyphenyl) like bis(26_2; phenyl-4_t-butylphenyl)], 4' succinyldiamine oxime. 33g and 2,2,. bisbipyridine 0 · 5 5 g dissolved in tetrahydro oxime / w, , ... A Fu (dehydration) 40g, boiled in nitrogen, Enter the nitrogen exchange in the crucible. To this solution was added bis(15 cyclooctane (o){N1(COD) 2} 1.0 g, and reacted at room temperature for 40 hours': here, the reaction was carried out in a nitrogen atmosphere. To the reaction solution, methanol (5Gml/ion exchange water was added to the solution) and stirred for about 1 hour. The solution was allowed to stand at room temperature for a sinking. Then, after drying the chamber, 2 In a medium. After filtering to remove insoluble matter, the solution is purified by passing through a column packed with aluminum telluride. Then, 16 of this solution is injected with decyl alcohol to precipitate and refine. The precipitate formed is recovered, and ethanol is used. After washing, the polymer G.35 g was obtained by drying under reduced pressure, and the obtained polymer compound 6 was converted into a polymer compound 6 estimated from the polystyrene equivalent of the polymer compound 6. Made with repeating units, Diandian 314723 66 1287570

HnC80 OC8H17

Example 7 &lt;Measurement of absorption spectrum and fluorescence spectrum&gt; Both of the molecular compounds 1 to 6 were easily dissolved in chloroform. The 〇·2〇/chloroform solution was spin-coated on a quartz plate to prepare a film of the polymer: the UV of the film was measured using a self-recording spectrophotometer UV365 manufactured by Shimadzu Corporation and a fluorescent knife photometer 85 曰. Visible absorption spectroscopy and fluorescence chromatography. The fluorescence peak wavelengths and relative intensities of the polymer compounds 丨 to 6 are shown in Table 1. 314723 67 1287570 Table 1 South Molecular Compound 1 2 3 4 5 6 m 8 Fluorescence Peak Wavelength (nm) 438 428 598 437 442 531 Fluorescence Intensity (au) 6.7 1.2 0.01 2.8 0.7 0.07 &lt;Manufacture and Evaluation of Components&gt; On a glass substrate to which an IT tantalum film is attached by a sputtering method to a thickness of 150 nm, a solution of poly(vinyl dihydroxythiophene)/polystyrenesulfonic acid (Bayer) by spin coating method is used. Films were formed at a thickness of 5 〇 nm and dried on a hot plate at /201 for 5 minutes. Next, a 1.5 wt (weight 1)% toluene solution of the polymerized material 1 was used to form a film in accordance with the thickness by a spin coating method. Further, after drying under reduced pressure for 8 hours at rc, after depositing lithium fluoride to about 4 nm, calcium was deposited as a cathode to about 2 nm, and then about 50 nm was deposited to prepare a polymer LED. The degree of vacuum at the time of deposition is 1 to 8 χ 10·6 Τ〇ΓΓ (Torr). A voltage is applied to the obtained element to obtain EL luminescence from a polymer compound! The luminescence onset voltage is about 7.6 V (volts) and luminescence The efficiency is about 〇i4cd/A, and the highest luminance is about i〇0cd/m2° EL peak wavelength and the peak wavelength of the film of the polymer compound i is slightly--, and it is confirmed that it is emitted from the polymer compound EL. Advantages of use] The polymer compound of the present invention can be used as a light-emitting material. Therefore, the knives can be used as a polymer LED. The polymer can be used as a planar light source as a backlight, 3:4723 68 1287570 A device such as a flat panel display. 69 314723

Claims (1)

1287570 No. 92114227 The patent application scope of the patent application is to modify the polymer compound, which is characterized by a single number, and the average number of polystyrene conversions (February 9, 1996) contains the repeated molecular weight shown in formula (1). 3 to ι〇8, X1 — Χ2 (1) [In the formula, Ar1 and Ar2 are still hitting this--you are a separate aromatic hydrocarbon group or a tetravalent heterocyclic group in which J is independently represented; X1 and X2 indicate that either side is c(=〇) or C ( Ri)(r2), and the other is 〇, s, c(=o), Si(=0), s〇2, Si(R3)(R4), n(r5), B(P6), P( R7) or p(=〇)(R8); (wherein, R1, R2, R3, r4, R5, R6, R7 and r8 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group , alkylamino, aryl, aryloxy, arylthio, arylamino, aralkyl, arylalkoxy, arylalkylthio, arylalkylamino, fluorenyl, decyloxy, hydrazine Amine, imine, substituted formazan, substituted formazanoxy, substituted forylidenethio, substituted forylideneamino, monovalent heterocyclic, aralkenyl, arylethynyl or cyanide )) represents a group represented by formula (2), formula (3) or formula (4); -Υ'-Υ2- (2) [wherein, Υ1 and Υ2 independently represent 〇, s, c (=〇 ), s(=〇), 1 314723 (amendment) 1287570 S〇2, C(R9)(R10), Si(Rn)(R12), N(R13), B(R14), P(R15) or P( = 0)(R16), (where R9, R10, R1 1. R12, R13, R14, R15 and R16 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkylamino group, an aryl group, an aryloxy group, an arylthio group, an arylamine group, Aralkyl, arylalkoxy, arylalkylthio, arylalkylamino, fluorenyl, decyloxy, decylamino, imido, substituted, carboxyalkyl, substituted, methoxyalkyl, substituted a decylthio group, a substituted megrolylamino group, a monovalent heterocyclic group, an arylalkenyl group, an arylethynyl group or a cyano group. However, when Y1 is other than C(R9)(R1G) or Si(Ru)(R12) , Y1 and Y2 will not be the same] -Y3=Y4- (3) [wherein, Υ3 and Υ4 respectively represent Ν, Β, Ρ, C(R17) or Si(R18), where R17 and R18 respectively Independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkylamino group, an aryl group, an aryloxy group, an arylthio group, an arylamino group, an aralkyl group, an aryl alkoxy group, an aryl group. Alkylthio, arylalkylamino, fluorenyl, decyloxy, decylamino, imido, substituted, carboxyalkyl, substituted, carboxyalkyloxy, substituted, methanylthio, substituted, dimethylamino, monovalent Heterocyclic, aralkenyl, aryl Alkynyl or cyano)] -Y5- (4) [wherein Y5 represents 〇, S, c(=0), s(=0), so2, C(R19)(R20), Si(R21)( R22) ' n(R23), B(R24), P(R25) or P( = 0)(R26), (wherein, R19, R20, R21, R22, r23, r24, r25 and 314723 (amendment) 2 1287570 R26 independently represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkylamino group, an aryl group, an aryloxy group, an arylthio group, an arylamine group, an arylalkyl group, an arylalkoxy group. Alkyl, arylalkylthio, arylalkylamino, fluorenyl, oxy, decylamino, imido, substituted formazan, substituted formazanoxy, substituted forylidenethio, substituted Methymidine, monovalent heterocyclic, aralkenyl, arylethynyl or cyano)] 21 represents _匸1136 = 〇1137- or _(: three (:-, 1136 and 1^7 are independent Represents a hydrogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group or a cyano group, and d represents no or 1]. 2. The polymer compound according to the first item of the patent application, wherein, in the formula (1, the formula is represented by the formula (2). 3. In the polymer compounding of the patent range f 2, ^] and ^ The bond is bonded to the adjacent position of the aromatic ring carbon of Arl, the χ and 2ΑΓ are bonded to the adjacent position of the aromatic ring carbon of Ar2, and the Υ and Ar are bonded to Ar1 $ # # # &gt; i + The adjacent position of the J 妷 ,, Y2 and Ari ... ...... in the adjacent position of the aromatic ring carbon of Ar. 4 · As claimed in the patent range 丨 molecular compound, wherein, in the formula = item 3 The height of the Ren-item 5. If the patent application scope is the first, the Ar and Ar2 are benzene rings. 'In the high score of 4 items of the stalking J dry coffer, γ1 and X2 are (c=0). Formula α &amp;: Application: In the polymer compound of the fifth item of the patent range, Υ1 and χ2 are (c=〇), :in the formula (1) 7. As claimed in the patent scope, /X is 〇 (gas atom) The molecular compound, the high of any of the two items or the third item, is in the repeating unit 314723 (amendment) shown in the formula (1), and the 10 1287570 full repeating unit is 10 mol% or more. Patent item i The polymer compound according to any one of the items 2 or 3, wherein the polymer compound is liquid crystal. 9. The polymer compound according to any one of the claims, the second item or the third item, Among them, there is a fluorescent material in a solid state. Door 1〇. A polymer electronic component 'characterized by: a polymer compound containing the towel range 1 to 9 of the patent. u. A southern molecular light-emitting element, It is characterized in that a light-emitting layer is provided between the electrodes formed by the anode and the cathode, and the light-emitting layer contains the polymer compound of any one of items 1 to 9 of the patent application. The feature is as follows: ^ φ | &gt; s has the two-molecule light-emitting element of claim 11 of the patent scope. 13· A segment display device, characterized by ·, as a · containing the U of the patent application scope Polymer light-emitting device 14 · A dot matrix display device, which is: a polymer light-emitting device containing the patent application scope item 11. $ $15· A liquid crystal display device characterized by ^ν τ 为Patent application area 11 The molecular light-emitting element is used as a backlight. 314723 (Revised) 4