TW200421936A - Light-emitting device - Google Patents

Abstract

The present invention provides a novel light-emitting device being capable of application in various areas and having excellent characters and efficiency of light-emitting. The invention relates to a light-emitting device containing at least one platinum complex represented by the following general formula (1): (wherein, ring A, ring B, ring C, every two independently, represent optionally substituted nitrogen-containing aromatic heterocyclic groups by coordination of nitrogen atom and platinum atom, and the remaining ring represents optionally substituted aryl group or optionally substituted heteroaryl group; Y represents halogen atom, or a direct bond or bonding via oxygen atom (-O-) or sulfur atom (-S-) to an optionally substituted aryl group or optionally substituted heteroaryl group (exception: adjacent two rings are nitrogen-containing aromatic heterocyclic group, Y is not a chlorine atom; non-adjacent two rings are nitrogen-containing aromatic heterocyclic group, Y is halogen atom).

Description

200421936 (1) Description of the invention: [Technical field to which the invention belongs] The present invention relates to a light-emitting element capable of converting electric energy into light. Specifically, it relates to novel light-emitting elements applicable to the fields of display elements, displays, backlights, electronic photographs, illumination light sources, recording light sources, exposure light sources, reading light sources, signs, signboards, and interior design. [Prior technology] At present, the development of various display elements is in full swing. Among them, organic electric field light-emitting elements (hereinafter referred to as organic EL (Electroluminescence) elements) can be used at low power bursts. The light emission is regarded as a potential candidate and attracts the main subject θ, A-1. For example, a light-emitting element that forms an organic thin film by evaporation of an organic compound has been known. The light-emitting element is made of a light-emitting material (eg, base acid) compound (hereinafter referred to as Alq) as an electron transporting material. , Can greatly improve the light emitting characteristics. Furthermore, although the applicability of this type of organic EL element in color displays has been enthusiastically reviewed in recent years, it is necessary to make the color display red, Di Duo and Luo Chu _ Ba, Yise and Jianse Temple various colors of light-emitting elements and improve their efficiency. Tienan light-emitting element special, place > car is ·, yr + ^ 卞% "raw hand slave, in addition to the use of fluorescent materials in the organic EL element light-emitting layer, but also connected to the wrong brake | 邳 有 礅 礅 用Phosphorescent material. Generally speaking, in the process of light emission from the stone, the singlet excited state is changed to three to excite the molecule from the ground state to the excited state, which causes the so-called cross-term phenomenon and then; ^ (] ntersystem crOssing) without radiation During the process of migration (n〇 ^ ad) 〇active 315J82 200421936 t-η), the light exhibits luminescence from the triplet excited state to the ground state. If the triplet state of the singlet energy disk of the organic phosphorescent substance is used, it can be estimated that high efficiency can be achieved. In this case, it is possible to extend the life of the organic element. Regarding organic EL elements using such a phosphorescent light-emitting material, it has been reported to use phosphorescence from an orthometalated iridium complex such as ginseng (2-phenylpyridine) iridium complex (lr (ppy) 3). Green light emitting element

Physics Letters, 75, 4 (1999)). Also, it has been reported as (2,3,7,8, i2, i3 17,1 8-octaethyl-2 1Η, 23Η -IIbline compound_n, n, n, n) platinum (ptEpD (U.S. Pat. No. 6,303,238; M.A. Baldoet et al., 3, 95 (1998), 15b 154). The The platinum complex is a red phosphorescent substance with a high external quantum efficiency reportedly 4. However, a more efficient phosphorescent substance is still being sought. Furthermore, if a light emitting element using a platinum complex is focused, It has been reported that the oxygen (2-benzylpyridine) platinum complex Pt (ppy) 2 and its analogs have been reported. In addition, it has also been reported as (6-phenyl-2,2, · bipyridyl-C, N, N) Chlorinated (II) and its derivatives as platinum complexes (E c. Connstable et al., J. Chem. Soc. Dalton Trans., 1990, 443-449; Tsz-Chun Cheung et al., J. Chem. Soc. Dalton Trans., 1996, 1 645-1651; Yurngdong Jahng et al.? Inorganica Chimica Acta 5 267 (1998), 265-270? Siu-Wai Lai et al.? Inorg. Chem. 5 38 (] 999) 404 6-405 5). The platinum complex is reported to be present Phenomenon of external light absorption and fluorescent luminescence. It has been reported that using this property, a platinum complex compound 8 15182 200421936 will be contained in polyethylene glycol, which is used to analyze living and ancient limb proteins (Chi-Ming Che et al Chem, m · C⑽mun · 2002, 2556-2557). However, there have been no reports on the application of this platinum complex to light-emitting elements such as, and, in addition, L elements. Right In the early days, it has the phenomenon of ultraviolet light absorption and fluorescent light emission. In other words, its heart 1 is not used in organic EL devices, and even if it can be used for organic θrussian components, is it better than the current general The organic EL element used is more preferable, and it is difficult to predict it. It is not easy to predict in this Japanese Patent Publication No. 175884. Although the external data / Wenge Temple data are not recorded, it is disclosed that the nitrogen-containing cyclic group and The carbon atom-containing% -like groups are each coordinated with two of each. The platinum complexes that are deposited are used as metal complexes for light-emitting elements. The platinum complexes specifically disclosed are two, one, and one. · All 4 mounting bases are independent of each other and platinum Position, 4 loops, which are each thin ... Only 2 of the clothes-like bases are bonded and the knife is in coordination with the ground, and 4 loops are made by the workers. Moreover, it is coordinated by J. Suzin, but it is not revealed that three to eight bad groups of η days become bond-like energies and complexes with platinum respectively. In recent years, the dyes used in filters have been changed. +, Θ $ this color filter first benefit or ^ phase photosensitive material ^ wood shaking, sensitizing dyes, dyes for paper poly dyeing, laser dyes, cutting off Fluorescent medicaments and organic light-emitting elements ^ The first substances, and the demand for them is, Luminescent material. Asia is eager to develop new organic light-emitting elements, in which organic substances are vacuum-evaporated and laminated for one-piece processability and large area to achieve high-brightness light emission. In other words, it is desirable to make 315) 82 9 π pieces by coating. However, two aspects of its luminous efficiency are t 'components that were previously manufactured by coating methods, especially in terms of points. Light-emitting materials. Various reviews have been conducted, among which the practical use of generation display elements has been enthusiastically entering the characteristics of light-emitting elements. The organic EL device using phosphorescent light-emitting materials is still not ready, Yuan: 2 ::, although the dawn has begun However, it seems that the optimization of its research is misleading about the luminescence characteristics, luminous efficiency, color purity, and structure of phosphorescent phosphorescent materials in order to solve these problems. As far as the current situation is concerned, Xinfa is expected by all parties. And the development of an effective manufacturing method of the material [Summary of the Invention] The present invention is #in the above-mentioned conditions> can be used in various fields # | 丨 κ 丁, the purpose is to provide elements. Pi has good light-emitting characteristics and light-emitting efficiency Xinlai Luminescence [Embodiment] The best form for carrying out the present invention This month, a commercial compound represented by the following general formula 关于 on a light-emitting element:

巧, Qiaodan

JO 315182 200421936 Nitrogen-containing aromatic heterocyclic groups coordinated by a nitrogen atom and a gardenia with a substituent: The remaining ring represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent. _ Prime atom, either an aryl group which may have a substituent or a aryl group which may be directly bonded or bonded via an oxygen atom (a 00 or 'atom d) ^ heteroaryl (with the limitation that the two adjacent rings In the case of a nitrogen aromatic heterocyclic group, Y is not a chlorine atom; the two adjacent rings are a nitrogen-containing aromatic heterocyclic group k, and Y is a halogen atom)]. Preferred examples of the platinum complex represented by the general formula [1], for example, the platinum complex represented by the following general formula ΠΊ:

(In the formula,% A] and ring 3] are each independent, and represent a nitrogen-containing aromatic heterocyclic group which may have a substituent, and a ring coat... χ represents a halogen atom). Eight Preferred examples of the platinum complex represented by the general formula [1], for example, the platinum complex represented by the following general formula [la ']: π 315182 200421936

[la,] (where 'ring c'] represents an aryl group or a heteroaryl group; RI, Chi 2 and r 3 are independent of each other, and represent hydrogen atom +, alkyl group, alkylated alkyl group, aralkyl group, alkenyl group, alkyne Aryl, aryl, amine, mono- or di-alkyl amine, mono- or di-aryl amine, alkoxy, aryloxy, heteroaryloxy, alkoxyquinyl, fluorenyl, amine, alkoxy Ethylamino, aryleneoxyamino, sulfoamido, sulfamoyl, μmethylamido, alkylthio, arylthio, heteroarylthio, fluorenyl, arylene, urea, and imidamine Radical, radical H from prime atom, cyano 1 acid radical, fluorene, sulfonyl radical, hydroxamic acid radical, phosphinic acid radical, hydrazine radical, aliphatic heterocyclic radical, aromatic heterocyclic radical, substituted Group or polymerizable group; X, a plurality of R, each other, a plurality of R2 each other, and / or a plurality of r3 each other, may form a condensed ring together with their bonded cymbals or ring C; It also represents the number of substituents R, R2 and R3 with m3, mi represents an integer of 0 to 3, and represents an integer of 0 to 4. In addition, when the above integer is 'plural R', plural R2 and plural R3 may be the same as each other Can also be different). A more preferable example of a ship complex represented by the general formula [1,], for example, the following complex represented by the general formula Π b ′] 15182 12 200421936

[lb,] (II: ~, R3, x, ~ and ~ and other complexes represented by the general formula Π] ^ f Platinum complexes represented by the general formula [1 ,,]: shell

Example 'e.g. the following (wherein'% B2 and ring c2 are each independently A and represent a nitrogen-containing aromatic heterocyclic group which may have a substituent 'ring A 2 represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent Also, ring B2 and ring C2, ring q and ring A2, or ring B2, ring C2 and ring eight 2 may be bonded to each other to form a fused ring; χ represents a halogen atom). 13 315182 Preferred examples of platinum complexes represented by the general formula Π ′ ′], for example, the face complexes represented by the following general formula [1 a ’′]. 13 315182

Bicyclic A2 represents an aryl group which may have a substituent or a substituent which may have a substituent: =; R1 and R3 are each independently and represent a hydrogen atom, an alkyl group, a functional group: a square alkyl group, an alkenyl group, an alkynyl group, and an aryl group. Amino, $ or dialkylamino, diarylamino, carboxy, aryloxy, heteroaryloxy, canyl, phenyl, amido, serino, aryloxy, amino, etc. Sulfonyl group, amino group, carbamoyl group, thiosulfanyl group, arylthio group, sulfanyl group, sulfenyl group, urea group, transition group, radical group, 1 group, 1 element atom, earth, continuous acid group , Retarder, stilbyl, fluorenyl, sulfinyl, phenyl, fine aliphatic heterocyclic, aromatic heterocyclic I yv%, radical, substituted silane, or polymerizable beauty. Forked 'plural R' And / 斿 斿 '3 铍 ^ beryllium put a R, can also be bonded with them! To form a fused ring; also, ring b, 2 and ring c, 2, ring c, 2 and ring two ^ B '2 and ring C, 2 and ring 2 or 3, 2 can also be combined with each other to form a condensed ring; m] mi don't represent the substituent r〗 & r3 and m3 represent an integer of 0 to 4, the number of, Ώ table An integer from 0 to 1, double, m, and m] and m1 are sound helmets of 2 or more. And plural R3 numbers 4, the same).丨 Here, it may be the same or different from each other; X and the above general formula [1] as described below are better examples of the platinum complexes [1 ,,]] f, such as the platinum complex shown by Xiao iU j Things: 14 1 ^ 5ΐδ2 200421936

(In the formula, ring B2 and ring (: 2 are each independently and represent a nitrogen-containing aromatic heterocyclic group which may have a substituent, and ring A2 and ring E are each independently and represent an aryl group which may have a substituent or a group which may have a substituent Heteroaryl; ring A2 and ring C2, ring C2 and or ring A2, ring C2 and ring B2 may be bonded to each other to form a fused ring; and '% 82, ring Jg2, ring C2 and / or ring E have a substitution In the case of a radical, each of the substitutions is a substituent which can be coordinated or bonded to a metal, and the atom coordinated or bonded to J in the substituent can be coordinated or bonded to a metal atom). A preferred example of the button complex represented by '' Ί is, for example, the platinum complex represented by the following general formula:

[laM where A2 and ring E are the same as above; R, fluorenyl 'is alkyl, arane A, and so on, "from independent" or m "" group, block, aryl, amine, '-Alkylamino group, or arylamino group, alkoxyme, kumeigan-earthen milk group, heteroaryloxy its carbonyl group, aryloxycarbonyl group, alkoxy group " son-in-law pericardial carbonylamino group, 315 丨 82 15 200421936 Oxycarbonylamino, amino, amino, methylamine, thiothio, heteroarylthio, sapphire blue, & ^ 1 ^ mm , Shimizu amine group, search group, thio group, halogen atom, grape: a moon earth, sulfonic acid group, carboxyl group, nitroxime acid group, sulfinic acid group, hydrazine group, fat self-violence , Fangxiang heterocyclic beauty, substituted silane groups or polymerizable groups; and clothing y 'feet and 11 can be combined with their two D than 17 fixed ring to form a fused ring; rule] disk. % A2, or Ri and R3 can form a condensed ring together; m] and m3 eight μ clothing 1 long m represents a substituent Han] and the number, m] represents 0 to 3 of the whole race 3 person counts; m represents Integer from 0 to 4 = 'when W is an integer of 2 or more' R] and (iv) a plurality of one another: a handle may also be the same mutually different; and, a plurality of R1 and / or a plurality of R3, breaking and the like may be spot bonded to the pyridine ring together form a fused -

ry. The substituent of eight K, selected A = or cyclofluorene can be coordinated with a metal or can be bonded to a metal; when it is a group, it can be coordinated or bondable by the substituent. Coordination or bonding of Mon atoms). A better example of the platinum complex represented by the general formula [1 ...], for example, the platinum complex represented by the following process [1 b '' '':

(Wherein Ri alkynyl, aryl, amine, mono or dialkylamino, mono or 315) 82 16 200421936 diarylamino, alkoxy, —y carbonyl, aryloxy, donkeyamine Sulfuryl, oxalyl, aryloxyamino, sulfamoyl, sulfanilyl carbonylamino, aryloxycarbonylamino, sulfonylsulfanyl, sulfenylsulfanylthio, sulfanyl Group, heteroarylthio group, atom, cyano group, continuous acid group, H amine group; ^ group, Wei group, halohydrazino group, aliphatic heterocyclic group, nitro group, hydroxamic acid group, sulfinic acid And JR; gold] gold R2 Λ square heterocyclic group, substituted silane group or two fluorene ring, or fluorene two ... and R, R2 and R3 can be with them m2, m3 And m4 respectively form a condensed ring with a jacket and a stupid ring; m1 'knife is the J table and does not replace its m] represents the number of integers 2, R, R3, and R4 from 0 to 3, ~ Zhengzhi, m2 and a Integers from 0 to 5. 3? Not integers from 0 to 4, when Table 1714, a plurality of R] 'A plurality of R2, m, and m4 integers of 2 or more may be the same or different; R] ^ I several R3 and plural R4 between each other and / or R4 between each other, can be matched : M 'R2 to each other, R3 to each other, fused rings; In addition, when pyridine or benzene ring of R ,, R2,, ° ° together form a substituent bonded to a metal, _ can be used as Metal-coordinating or bondable atoms and metal atoms: Coordination or bonding at this position or bond in ° xuan substituent. In the present invention, the platinum complexes formed by A, ring β, and ring C shown in Table 1 of the general formula [1] above are formed by a ligand of the ring and connected to or through the oxygen atom (CU). Or sulfur is a human halogen atom or a straight, aryl group at the tenth position of item L or a heteroaryl group which may have a substituent, and may have a substituent if the adjacent two rings are platinum containing gas 2 Conjugate (restricted Fangxiang Momozi, non-adjacent two rings are each ^, volume ¥, Y is not a chlorine atom)]. For aromatic heterocyclic groups, y is 315182 17 200421936. Among them, any of ring A, € B, and ring c represents & coordinated by nitrogen atom and atom, and the remaining i is determined by carbon atom and #Atomic bond ring group. The equal percentage of b may be a single ring, a polycyclic ring, or a fused ring, respectively, and ring a and the ring 袠 B may form a fused ring, or ring A may form a fused ring together with ring C and ring B. This #complex is an orthometallic platinum complex. Li Dazhuang'er'mei, metallized complex (〇rth〇metaiated c〇〇 ^^, ^ Shiyamamoto Akio "Basics and Applications of Organometallic Chemistry" pp. 150 to 232 (Shanghuafang Company, 1982) ); Or H Yersin, "Photochemistry and Photophysics of Coordination Compounds (PhQtGehemistry and

PhotophySlcs of coordination Compounds) j 71 JL 77 f and 135th to i 仏 i, u 丄 王 // _ _ _ year issued etc., etc. Bélag (s_㈣㈣) company, China. The general name of the compound group that has been contained. Daimei's 2 general formula [1] can represent a 3-gas aromatic heterocyclic group represented by ring A, mB and ring C, and the general formula [can have substituents & ... Private heteronuclear groups, and nitrogen-containing aromatic heterocyclic groups which may have substituents represented by the general formula [1 ,,] Central ring J 2 Yi 2 Independent nitrogen-containing aromatic heteroaromatic heterocyclic group. Yi Zhiyuan, and the nitro-containing aromatic heterocyclic group substituted with lice may be, for example, 2 to 15 carbon atoms and at least and i as a hetero sheet; Wang 1] and 芏 > has 1 hetero chip: lice atom The heterocyclic group may also have 1 to 3 fragrant hetero-P-gans ten times, the original temple. In addition, the above nitrogen-containing aromatic I group may be a monocyclic ring containing 315,182 (... or 6 members is preferred), and also a heterocyclic group containing fangfang aromatic group.

base. Gas-containing A A ring or conjugation ring

DttD well ring, daphne ring, π pyrazonol may be, for example, a pyridine ring, a pyrimidine ring, a lin%, an isotiline ring, a singularity ring, a zero ring, a salivary ring, a sigh. Zeng Lin ring, benzene Benzalimidine ring, quinjunline ring, naphthyl ring, substituted nitrogen-containing aromatic heterobi = azole ring and benzothiazole ring, etc. At least one hydrogen atom is substituted 2 ^ nitrogen-containing aromatic above The heterocyclyl group may be a hydrocarbon group, a substituted second-generation nitrogen-containing aromatic heterocyclic group. Taking an aliphatic heterocyclic group, an aromatic two, an aliphatic heterocyclic group, a substituted alkoxy group, and a substituted fluorene group Soil, substituted aromatic heterocyclic group, sublimation, aryloxy group, substituted aryloxy group, aromatic ... give substituted arylalkoxy group, heteroaryl group, alkoxycarbonyl group, Guan 4 ρI — substitution Chain-chain lactamthione, 〃 μ ", alkoxycarbonyl, fluorenyl, fluorenyl, dioxo,: 'membered thio, arylthio, heteroarylthio, halide atom, butane-yang So, amine, substituted amine, hydrazine, cyano, nitro, _, its, retarder, lysate, succinylamino, amine group, substituted fluorenyl group, aminomethyl XI , Substituted carbamoyl group, sulfonyl group, sulfonyl group, sulfinyl group, sulfinyl group, ureido group, substituted ureido group's mercapto group, fluorenylamino group, substituted silyl group, and Polymerizable group and so on. The group may be, for example, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an aryl group, and the like. The minor group may be straight-bonded, branched, or cyclic, such as an alkyl group having 1 to 15 carbons (and preferably 1 to 10 carbons, more preferably 1 to 6 carbons). Specifically, such as methyl, ethyl, n-propyl, 2-propyl, n-butyl, 2-butyl, isobutyl, third butyl, n-pentyl'2-pentyl, third pentyl Group, 2- 19 315182 200421936 methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, n-hexyl, 2-hexyl, hexyl? -Methylpentyl, 3-methylpentyl, 4-methylpentyl, 2-methylpent-3-yl, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. The dilute group may be linear or branched, for example, an alkenyl group having 2 to 15 carbons (and preferably carbon = 2 to 10, more preferably 2 to 6 carbons). Specifically, alkenyl, 1-butenyl, fluorenyl and hexadecyl. The block group may be linear or branched, for example, a block group having 2 to carbon atoms, preferably two to two carbon atoms, and more preferably 2 to 6 carbon atoms, specifically 5, such as ethynyl, 1- Propyne, what? k Discuss pentamyl and hexamethylene. U Bu Dingyi, 3 · Dingwei, such as aryl groups with 6 to 14 carbon atoms, specifically, phenyl, phenyl, and dibenzyl. + Soil ^ at least 1 hydrogen branch is replaced by a shirting group: aromatic group with 7 to 12 carbon atoms, specifically such as fluorenyl, -non-ethyl, b-propyl and 3-naphthyl Base etc. Aliphatic heterocyclyl is, for example, a carbon number with preferably ... heteroatoms, such as nitrogen, and (and other heteroatoms ... members (... or 6 = two primary: or sulfur atom heterocyclyl '... or thick) Cycloaliphatic heterocycles ::: ㈣ Specific examples, such as crocodyl radicals, veins. Anthyl tetrafuranyl and tetrahydropyranyl, etc. * Horse brownline, aromatic heterocyclic groups are, for example, 2 to carbon ^ To 3 are preferred) heteroatoms, such as gas atoms, 1 less (and 5 to 8 members of the temple heteroatom (and 5 凫 L, sub or sulfur atom-shell is preferred) monocyclic Heteroaryl 3) 5182 20 200421936 Hetero AI or fused% heteroaryl, specifically, for example, furyl, aryl, etc., dense. Base, 0-based group ... Sialophilic, thiasialyl, benzomethyl, benzothienyl, dioxin: fluorene: linyl, phenyl, phosphino, phthaloyl, quinavalinyl, naphthyl bis, benzofluorenyl, Benzophosphyl, benzothiawyl, etc. The A 2 group may be linear, branched, or cyclic, for example, carbon number] C :: In terms of "oxy, ethoxy, n-propyl Oxy, 2 n-butoxy, 2 · butoxy, iso Oxy group, ^ lactyl group: 2-methyl τ oxy group, w butyl butoxy group, 2, 2 < methyl bis: ^ mesalanyl group, 2. methyl pentyl oxy group, 3 'methyl hydrazone Oxy, 4-methy || selenium, 5-methylpentyloxy, cyclohexyloxy, etc. The pentylaryloxy group can be, for example, a phenoxy group, a carbonoxy group, and anthracenyloxy group having 6 to 14 carbon atoms. Early soil 'specifically' such as aralkyloxy may be, for example, 7 to 12 carbon atoms such as benzyloxy '2-phenethoxy, b-propoxy, A, dilactyl, specifically propyl Oxydecabutoxy, 2-phenylbutoxy = benzene7 " oxy and Ibenzyl, 丨 -phenpentyloxy, Ibenzyl, 4-benzylbenzylbenzyl 2-benzylbenzyl , 3 • phenpentyloxy, lice-ben-pentyloxy,! -Phenhexyloxy, pentyl, hexadecyloxy-hexyloxy, hexadecyloxy ^ Hexyloxy contains, for example, at least! Atoms (eg, nitrogen, oxygen, or sulfur atoms are preferred) Heteroaryloxy groups to M, specifically, such as' :) have a carbon number of 2 2'pyrimidinyloxy and 2-quinolinyloxy Etc. ▲ 2 'phenoxy, oxo can be straight-chain' split-like or cyclic, such as carbon number 2 to 315182 2] 200421936 1 The alkoxycarbonyl group of 9 is specifically, such as methoxycarbonyl, oxocarbyl, n-propylna, n-butadiene, third-butoxyfluorene, and oxo-2-: ... 2-ethylhexyloxy, Lauryloxyalkyl, stearyloxycarbonyl, cyclohexyloxycarbonyl, etc. Aryloxyalkyl may be, for example, aryloxyalkyl having 7 to 20 carbon atoms, specifically, such as phenoxycarbonyl and naphthyloxycarbonyl. An aralkyl j carbonyl group may be, for example, an aralkyloxy carbonyl group having 8 to 15 carbon atoms, and specifically, 'such as a benzyloxycarbonyl group, a phenethyloxycarbonyl group, and a 9 · g methoxycarbonyl group may be linear. Or branched, for example, the number of carbons derived from fatty acids such as fluorene or aromatic acid! To the acid group of 18, specifically, such as ^ fluorenyl, ethoxy, propyl, butyl, and pentamidine Base, pentyl, hexyl, lauryl, stearyl, and benzyl. The fluorenyloxy group may be a fluorenyloxy group having a carbon number of 2 to 8 from a carboxylic acid, and specifically, such as ethyl alcohol, propyl alcohol, butyl alcohol, di: oxy, pentyl Oxy, hexanox, lauric oxy, stearyloxy, etc. The alkylthio group may be linear, branched, or cyclic, for example, an alkylthio group having 6 to 6 carbon atoms, specifically, #sulfanyl, ethylthio, n-propylthio, propylthio, n Butylthio, 2-butylthio, isobutylthio, tertiary butylthio, pentylthio, hexylthio, and cyclohexylthio. The arylthio group may be, for example, an arylthio group having 6 to 14 carbon atoms, and specifically, such as a phenylthio group, a naphthylthio group, and the like. The aralkylthio group may be, for example, an aralkylthio group having 7 to 12 carbon atoms, specifically, such as sulfanylthio group, 2-phenylethylthio group, and the like. ° 315) 82 200421936 _ For example, the right sulfur m 1 3 now has 1 (even 1 to 3 is preferred) lu ^ Lumei's heterosulfur, specifically, such as pyridine Thio, 2-benzimidazole 4, 2-benzylthio and 2-benzothiasialthio. The _ prime atom may be a fluorine atom, a chlorine atom, a daughter, a desert atom, a gardenia, and the like. The M-dioxy group may be, for example, a diphenyl dioxy group having a carbon number of i to 3, and so on. Dimethyldioxy, diethylenedioxy, propylenedioxy, and the like. Substituted nicotyl, such as substituted alkenyl, substituted alkenyl,,! Substituted blocks, substituted aryl groups and substituted aryl groups. The disubstituted alkyl group is at least one hydrogen atom of the above alkyl group, and the alkyl group, alkoxy group, and alkoxy group are substituted by alkyl group, diyl group, halogen atom, amine group, or substituted amine group. atom. The substituted amino group is the same as the above-mentioned substituted amino group. A halogenated group substituted by a halogen atom, that is, a * alkylated group 'is the number of carbons in which at least i hydrogen atoms of the above alkyl group are halogenated (such as disordered, chlorinated, desertified, or mothized) by a halogen atom! To M (and the number of charcoal is 1 ^ 10 is more preferred, and the number of charcoal is 1 to 6 is more preferred) dentition group, specifically 'such as chloromethyl, methyl, trifluoromethyl, 2 -Chloroethyl, 3-propyl, and 3,3,3-trifluoropropyl. A substituted aryl group is at least one hydrogen atom of the above-mentioned aryl group. The above-mentioned aryl group is substituted by an alkyl group, a halogenated alkynyl group, a thiol group, a halogen atom, an amine group, or an aryl group a substituted with a substituted amine group. An aryl group in which two hydrogen atoms adjacent to the group are substituted with a substituent such as a secondary dioxy group. The substituted amine group, halogenated thiol group, fluorinated oxy group, halogen atom, substituted amine group and fluorene dioxy group are the same as above, and X, substituted amine group is the same as the substituted amine group described later. Specific examples of aromatic groups substituted by sintered groups are 315182 23 200421936, such as fluorenyl and difluorenyl. The substituted arsenyl group is at least the above arylene group! An aralkyl group substituted with a hydrogen atom by a substituent such as an alkyl group, a halogenated alkyl group, an alkoxy group, a halogen atom, an amine group, or a substituted amine group, or the adjacent two hydrogen atoms of the aryl group in the above aralkyl group are replaced by Aralkyl substituted with substituents such as butanedioxy. The alkyl group, the halogenated alkyl group, the alkoxy group, the halogen atom, and the substituted amine group are the same as those described above, and the substituted amine group is the same as the substituted amine group described later. The substituted aliphatic heterocyclic group is an aliphatic heterocyclic group in which at least i hydrogen atoms of the aforementioned aliphatic heterocyclic group are substituted with a substituent such as an alkyl group, an alkyl group, an alkoxy group, or a hydrogen atom. ρ Α η ^ as clothing base. Alkyl, alkylated, alkoxy and halogen atoms are the same as described above. The substituted aromatic heterocyclic group is a heterocyclic group in which at least i nitrogen atoms of the above-mentioned heteroaryl group are substituted with a substituent, amidinyl group, a silk group, a halogen compound and the like. Alkyl, "alkyl, alkoxy, and halo atoms are the same as those described above, and the alkoxy group is at least one chlorine atom of the above oxy group. The alkyl groups substituted by iso-substituents, such as ^^^ group, alkyl group, silk group, and functional element atoms, are the same as above, and 7 f ..., and substituted amino groups are the same as the substituted amino groups described below.

A substituted aryl group, at least one hydrogen atom of which is an alkoxy group, is a halogenated group, a halogenated minor group, a twisted group, and a "W atom, an amine group, or a substituted amine group ... η group, The above aryloxy group is adjacent (two hydrogen atoms are stretched to a single lactyl group, etc. to a square lactyl group. Carboxyl group, alkylated alkyl group, alkoxy group 315182 24 200421936 group, i element atom, and alkylenedioxy group It is the same as above, and the substituted amine group is the same as the substituted amine group described later. The substituted aralkoxy group is at least one hydrogen atom of an aralkyloxy group, a halogenated group, a halogenated alkyl group, or an alkoxy group. , Halogen atom, amine group or substituted amine group and other substituted aryl alkoxy groups, or the two aryl groups in the above aryl alkoxy group adjacent to the aryl group are substituted by alkylene dioxy group and other aryl alkoxy groups The alkyl group, alkyl group, alkoxy group, halogen atom, and alkylenedioxy group are the same as above, and the substituted amine group is the same as the substituted amine group described later. The substituted amine group is, for example, an amine An amine group in which one or two hydrogen atoms are substituted by a substituent such as a protecting group. A protecting group can be used as an amine protecting group, and any Any kind can be used, for example, those described in "PROTECTIVE GROUPS IN ORGANIC SYNTHESIS, Second Edition (JOHN WILEY & SONS, INC.)" Can be used as the amine-protecting group. Specific examples of the amine-protecting group, such as alkyl, Aryl, aralkyl, fluorenyl, alkoxycarbonyl, aryloxycarbyl, and arylfluorenyl, etc. Alkyl, aryl, aryl, aryl, alkynyl, aryloxybenzyl, and aryloxycarbyl Aralkyloxycarbonyl groups are the same as above. Specific examples of amine groups substituted with alkyl groups, that is, amine groups substituted with alkyl groups, such as N-fluorenylamino, N, N-diamidino, N, N-diamine Ethylamino, N, N-diisopropylamino and N-cyclohexylamine and other mono or dialkylamino groups, etc. Specific examples of aryl groups substituted with aryl groups, that is, aryl groups substituted with aryl groups, such as N-aniline, diphenylamino, N-naphthylamine, N-Cylenylaniline and other mono- or diarylamino groups, etc. An amine group substituted with an aralkyl group, that is, an amine group substituted with an aralkyl group Specific examples, such as mono- or diaralkylamino groups such as N-benzylamino and N, N-dibenzylamino groups, etc. Amino groups substituted with fluorenyl groups, that is, 315182 200421936, such as fluorene Amine, Acetylamine , Propylamino, pentamidine, pentamidine, hexanoic acid, and ammonium acetic acid amino groups, etc. Specific examples of amine groups substituted with oxalyl groups, that is, alkoxycarbonylamino groups, Such as fluorenyloxycarbonylamino, ethoxycarbonylamino, n-propoxycarbonylamino, n-butoxycarbonylamino, tertiary butoxycarbonylamino, pentyloxycarbonylamino and hexyloxycarbonylamino, etc. Specific examples of oxycarbonyl-substituted amine groups, that is, aryloxycarbonylamino groups, such as amine groups in which one hydrogen atom of the amine group is substituted with the above aryloxycarbonyl group, specifically, such as phenoxycarbonylamino and naphthyloxycarbonyl Amine groups, etc. Specific examples of aryl groups substituted with aralkyloxycarbonyl groups, that is, aralkyloxycarbonylamino groups, such as benzyloxycarbonylamino and the like. The luteinic acid amine group is, for example, a substituted group represented by RS〇2_NH- (R represents an unsubstituted alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an aromatic group or a substituted aromatic group, etc.) Of sulfonamide. The alkyl group, substituted alkyl group, aryl group, substituted aryl group, aralkyl group, and substituted aralkyl group represented by R described above are the same as those described above. Specific examples of the sulfanilino group include a mesylsulfonamido group and a p-phenylsulfonamido group. A substituted sulfamoyl group is one or two hydrogen atoms of the amine group in the sulfamoino group, the above-mentioned alkyl group, the above-mentioned substituted alkyl group, the above-mentioned aryl group, the above-mentioned substituted aryl group, the above-mentioned aralkyl group Or the above-mentioned substituted aralkyl groups substituted by a substituent such as an aralkyl group, and specifically, such as N-fluorenylsulfonyl, N, N-difluorenylamino and N-phenylamine Wait. The substituted amine group is one or two hydrogen atoms of the amine group in the amine group. The above-mentioned alkyl group, the above-mentioned substituted alkyl group, the above-mentioned aryl group, the above-mentioned substituted aryl group, the above-mentioned aralkyl group Or the amine group substituted with the substituents such as the substituted aralkyl group, specifically, such as N-fluorenylamino group, N, N- 26 315182 200421936 diethylamino group and N-benzene Methylamine formyl and the like. Mei is, for example, a substituted stilbene group represented by -s〇2_ (R is the same as above). Specific examples of fluorenyl, such as phenyl and p-toluene. The subgroup is, for example, an arylene group represented by -s0- (R is the same as above). Specific examples of sub-gamma are, for example, formyl and benzylidene. 〃, the substituted ureido group is i or 2 chlorine atoms of the amine group in the ureido group and / or the i hydrogen group of the imide group in the ureido group is the above-mentioned alkyl group, the above-mentioned substituted alkyl group, the above-mentioned aryl group 2. Urea groups substituted with substituents such as the above-mentioned substituted aryl group, the above-mentioned fluorenyl group, or the above-mentioned substituted aromatic compound, specifically, such as hydrazone and N-phenylureido. Substituted phosphoramido is at least one hydrogen atom of the phosphoric acid group in phosphoramido, the above-mentioned substituted silk, the above-mentioned group, the above-mentioned substituted aryl, the above-mentioned aralkyl, or the above-mentioned substituted The & amino group substituted with a substituent such as an aralkyl group, specifically, such as ethylphosphonium group and phenylphosphonium group. The substituted silane group is, for example, the three hydrogen atoms of the silane group are the above-mentioned alkyl group, the above-mentioned substituted alkyl group, the above-mentioned aryl group, the above-mentioned substituted aryl group, the above-mentioned aralkyl group or the above-mentioned substituted aralkyl group, etc. Tri-substituted silyl groups substituted by substituents, specifically, such as trimethylsilyl, tertiary butyldifluorenylsiliconyl, tributyldiphenyl ^ ylbenzyl, and triphenyl; g Tongji and so on. The bonding group is a group having a polymerizable double bond or a bond such as an ethyl group, an acrylic group, an ethylene group, and a (fluorenyl) propenyloxy group, or an oxetanyl group or Ring-opening polymerizable cyclic test groups such as tetrazine, pyrimidine, 315182, 200421936, etc. Among these substituents, substituted hydrocarbyl groups, substituted aliphatic heterocyclic groups, substituted aromatic heterocyclic groups, substituted alkoxy groups, substituted = square oxy groups, substituted arylalkoxy groups , Substituted heteroaryloxy, alkoxycarbonyl, aryloxy truncated, aryleneoxy, aryl, acid, oxanyl, aralkylthio, arylthio, heteroarylthio, butane Dioxy, substituted amine, hydrazine, hydroxamic acid, substituted amine sulfonyl, substituted amine fluorenyl, sulfonyl, sulfhydryl, substituted ureido, The phosphonic acid amine group or the substituted silyl group may be further substituted with a group selected from the above-mentioned group of substituents. In the general formula U], an aryl group which may have a substituent represented by ring man, ring B, and ring c; an aryl group which may have a substituent represented by ring c] in general formula [η]; and general formula [1 " ] ,,,], [1 ~], and [1 ^,], an aryl group which may have a substituent represented by ring eight 2 such as an aryl group and a substituted aryl group, etc. Aryl groups such as heteroaryl groups and substituted heteroaryl groups. Earthenyl groups may be monocyclic, polycyclic or fused ring aryl groups, such as aryl groups having 6 to 14 carbon atoms, specifically, such as benzene Group, Chai group, onion group, biphenyl group, etc. The substituted aryl group is an aryl group in which at least i chlorine atoms of the above aryl group are substituted with a substituent. The substituent is a nitrogen substituted aromatic heterocyclic ring which has been previously substituted. The substituents described in the substituent part of the group are the same as the substituents. Heteroaryl is, for example, 2 to 5 carbons and contains at least 1 (and 2 to 3 4 as ethyl) chain atoms (such as nitrogen atom, oxygen Atoms or heteroatoms such as sulfur atoms) of 5 to 8 shells (5 or 6 members are preferred), monocyclic heteroaryl, polycyclic or fused pepper-type heteroaryl, specifically, for example, furan Radical, thienyl, pyridine 315 182 28 200421936 base, pyrimidinyl, pyridyl, daphthyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, benzofuranyl, benzothienyl, quinolinyl, isofluorinyl, quinoxaline Groups, phthaloyl groups, quinazoline groups, naphthyl groups, "zolinolinyl groups", benzoxazole groups, benzoxazolyl groups, benzothiazolyl groups, and the like. A substituted heteroaryl group is a heteroaryl group substituted with at least t group of the above heteroaryl group. The substituent is the same as the substituents detailed in the substituent section of the previously substituted nitrogen-containing aryl = ring group. For example, when ring C2 and ring B2 are bonded to each other to form a condensed ring, specific examples of the condensed ring include U0-morpholine ring and 4,5_diaza_9Y western homocyclic ring, such as ring When the ring Cl (or ring Ci and ring Bι) or ring A] and ring C are bonded to form a fused ring, the specific details of the fused ring " for example, H = and 7,8-benzoquinoline ring, etc. ^ The ring A, ring C and ring B; itA], ring q and ring b]; or% B2, ring I and ring & can be bonded to each other to form a coupled ring. In the general formula (I), the halogen atom represented by Y may be, for example, a chlorine atom, an iodine atom, or a fluorine atom. When Y is an aryl group which may have a substituent or a heteroaryl group which may have a substituent, which is bonded directly or via an oxygen atom (4) or a sulfur atom (i), the aryl group which may have a substituent or The heteroaryl group having a substituent is the same as the aryl group which may have a substituent shown in Ring A 2 or a heteroaryl group which may have a substituent. The above-mentioned general formulas [1,], [la,], [lb,], [1 ,,] and [la J τ] The halogen atom shown may be, for example, a chlorine atom, a bromine atom, or an iodine atom. 1 '' '] and the general formula [la' ''], the ring E represents an aryl group which may have a substituent and a heteroaryl group which may have a substituent. The formula shown in 315182 29 200421936, and the definitions of the various substituents shown in the general formulas R2 and R3 and the description of the substituents with ring C are shown in [], [1,], [1 ,,] and [ The ring B in 1 ,,,] is exactly the same. Preferable specific examples of the complexes related to the present invention represented by the general formula [1] 'include, for example, platinum complexes represented by the following (Γ-1) to (1, · 32).

315182 30 200421936

Preferred specific examples of the platinum complex of the present invention represented by the general formula [1 ”] include, for example, the platinum complexes represented by the following (ΓM) to (1, -36). 31 315182 200421936

(r-2)

(r-i2)

315182 200421936 (1-13)

(1-14)

(1-16)

(1 " -19)

(1〃 to 23)

33 315182 200421936

(1 " a 34)

(Γ a 35)

(1-36)

Preferred specific examples of the platinum complex of the present invention represented by the general formula [1 '' '] are, for example, platinum complexes represented by the following (factory `` -1) to (Γ' '-15) Etc. 34 315) 82 200421936

1-13 1-14 1 ...- 15

The button complex of the present invention represented by the general formula [1 '] can be synthesized, for example, by the following method. That is, such as "organometallics", volume 18, pages 3 3 37 to 3341 (1999) (〇rganometall i cs 1 9 9 9,] 8, 3 3 3 7 to 3 34 As described in 1), a platinum compound of potassium tetrachloroplatinate and a ligand of [], 3-bis (2-Πpyridyl) benzene can be heated and stirred in a solvent such as acetic acid to prepare 35 315182 200421936. . The fine compound used as a raw material may be tetrachloropyrrolate, tetrabromotamate or tetrachloride acid steel ... and other hydrates may also be used. . As the reaction solvent, acetamidine, 2-ethoxyethanol, acetonitrile, or the like may be used, or these solvents may be reacted by adding water to form an aqueous solvent. X, the reaction temperature can be carried out at 30 to 50 ° C, and preferably 70 to 100 t :. The platinum complex compound paid in this step is usually a hydrate. It is difficult to perform purification such as sublimation in the original state, and it cannot be used as a light-emitting element material because of water. To remove water of hydration, organic metal compounds such as Grignard reagent can be used to remove water of hydration. In addition, in the step of removing the hydrated water, by using a Zirina reagent containing a different 1 * element atom different from the halogen atom bonded to the conjugate hydrate, at about G i 8G ° C (and about C is more temperature-sensitive, and the conversion of hydrated water to remove elementary atoms can be performed together. Among the Grignard reagents used herein, carbaryl quinine reagent and aryl quinine reagent can be used. However, aryl quinine reagent is more preferable, and stylyl quinine reagent is particularly preferable. The surface complex of the present invention represented by, [] can be, for example, a platinum diene complex represented by the following general formula U]

Pt (X) 2 (D) [2] (where 5 jL j », t is not a non-co-diene compound, X represents a halogen atom) and a compound represented by the general formula [3]

Η [3] 36 315182 200421936 (wherein 1B2 and ring c2 are each independently aromatic hetero ρ Δ indicates that τ has a nitrogen-containing substituent as a fluorenyl group, and the α2 table must not be right%. The aryl group of the soil may have soil extraction, and 垓 Β2 and the ring c, the ring c, the ring c2, and the ring A2 can be produced by ❼ or ring dagger. ~ To form a condensed ring) reaction easily, A platinum diene represented by the formula 17 [1] having a desired halogen original error. Difficulties in obtaining or difficult to synthesize the master 1 Yi Rishou, can make it easy to obtain or synthesize the diene complex compound represented by the formula [2], and for the introduction of desired, plain tablets for , Price: [3] the expression of the other. The reaction of the halogenating agent used by Jingzi to achieve this situation can make the platinum diene complexes represented by the general formula [21 # # 『31 所 #-L ', the compounds represented by the general formula, and the guide The halogenating agent used for the halogen atom of the eighth period king :: 1 reaction; also, 'the compound represented by the general formula [2] ... the dilute error 2 can be reacted, and then it can be introduced into The halogen atom used by the king of d is reacted with a halogenating agent. In the latter case, that is, in the case of performing a two-stage reaction, it is possible to perform the second-stage reaction in the same batch without isolating the product after the previous reaction. . Also, "when producing a complex of the surface represented by the general formula [1 ,,] with a desired halo atom", when a complex of the structure represented by the general formula II ,,] with other halo atoms is available, may be The inversion complex, that is, the inversion complex represented by the general formula 具有 having other dentin atoms, is directly reacted with a halogenating agent for introducing a desired dentin atom. In the general formula [2], can the halogen atom represented by X be a chlorine atom? ,,; stinking 315182 37 200421936 atom, moth atom or fluorine atom, etc. In the general formula [2], the two _ prime atoms represented by χ may be the same ::: but the same prime prime atom is preferred, and furthermore, from the "He," the same prime prime atom of this temple with a chlorine atom In formula U], the non-conjugated diene compound represented by D may or may not be A & 7 and 榀 ± " unfolded 'non-co-diene compound is cyclic non-conjugated Dienelated talents, which can be any of monocyclic, polycyclic, fused cyclic or crosslinked cyclic. Non-conjugated diene compounds can also be non-co-diluted compounds substituted with substituents. 'It is a substituted non-common dilute compound. The above-mentioned substituted group is not limited as long as it is a substituent that does not adversely affect the manufacturing method, and the substituted group may be used with a previously substituted nitrogen-containing aromatic compound. The heterocyclic groups have the same substituents as described in the description of the substituents. Among these non-conjugated 2-ene compounds, cyclohexyl octadiene, bicyclic [221] heptadiene-2,5-diene, and 1,5-hexadiene and the like are preferred, and hexadiene and the like are more preferred non-co-diluted compounds. In the method for producing a facet complex represented by the general formula [1], The compound represented by the general formula [3] of the diadiene complex reaction represented by [2] is a compound having a ring B2, a ring c2, and a ring eight 2 and a ring and a ring C2 are used to match the turn atom. Compound having the function of bonding a carbon atom on a ring A2 to a platinum atom. The definitions and specific examples of the ring, ring C2, and ring A? Are as described previously. The general formula [3] Preferred examples of the compound include, for example, the compound represented by the following general formula [3a]: 38 315] 82 200421936 (wherein ring B ': the same).

[3a], η], and the above-mentioned example, for example, the present invention represented by (1, M) to (1, '36) ... a complex (has three ligands and has a halogen atom) (Original metallization button complex) is a preferred embodiment, and the structural towel is formed by removing platinum and a part after removing the prime atom. In the manufacturing method of the present invention, when producing the initial complex represented by the desired formula of the prime element *, the platinum diene complex represented by the general formula [2] having the desired southern prime atom is produced. The compound used when the composition is difficult to obtain or the synthesis is not easy can be, for example, a metal halide, a halide dish or a halide-type inorganic halogenating agent, or an organic halogenating agent. The metal halide may be, for example, lithium fluoride, lithium chloride, lithium bromide, lithium iodide, sodium fluoride, sodium chloride, sodium bromide, sodium iodide, potassium fluoride, potassium chloride, desertification, moth pupae , Metal ions such as cesium fluoride, cesium chloride, desertification and moth, or magnesium fluoride, magnesium chloride, magnesium bromide, magnesium iodide, chloride, > calcium odor, or iodide Alkaline earth metal halides such as calcium. The phosphorus ion may be, for example, phosphorus trichloride or phosphorus tribromide. The halogens may be halogens such as fluorine, chlorine, bromine or iodine. Examples of the organic halogenating agent include succinimides such as N-chlorosuccinimide and N-bromosuccinimide. 39 3) 5182 200421936 This temple halogenating agent is particularly preferably a metal halide. Next, the formation and generation of the platinum complex of the present invention represented by the general formula ΠΊ can be explained using the following reaction schemes 1 to 3. Clothing method

Reaction Scheme 1 is a description of a combination of a platinum diene represented by the general formula [2] (hereinafter referred to as a platinum diene complex [2]) and a chemical compound represented by the general formula [3] (hereinafter referred to as a compound) [3]) Reaction to produce a compound represented by the general formula H,]] (hereinafter referred to as a platinum complex π "]) in the production method (hereinafter abbreviated as" 1 "). The K-platin platinum complex [1 ,,] is the reverse depletion complex [2] and compound [3] in the presence of an appropriate solvent, and inverse storage under the influence of emotional gases as needed = easy to manufacture . Furthermore, the manufacturing method can also use an ultrasonic generating device to perform a reaction as required. The amount of the platinum diene complex [2] and the compound [3], for the platinum diene complex [2]: the compound [3] can usually be from 0.5 to 20 equivalents (in addition to 0, 8 The range of 5 to 5 equivalents is preferred) is appropriately selected. The atmosphere production method 1 '' is preferably performed in the presence of a solvent. May be, for example, n, n-dimethylformamide, formamide, or N, N-dimethylacetamide, and other amines; ethano-containing organic compounds, such as dioxin, 315182 40 ^ 0421936 Chlorinated hydrocarbons hydrocarbons §5 ^, Hydrogen 0-Ethane-Chloroethane, Λ ^ 'from chloroform, halogens such as carbon tetrachloride or o-dichlorobenzene, etc. , Toluene or dimethyl ether; etc .: Fatty butyl methyl esters such as burned decanoate or cyclohexane, dimethyl hydrocarbons, diethyl ether, diisopropyl! ^ Riboacetam, ethylene glycol diethyl ether, four 5 — Dioxane, or a slice of methyl ethyl _, methigen 5, stilbene, and other ethers; acetone, 2-propanol, n-butyl / ketone, or cyclohexanone, and other ketones; methanol, ethanol, alcohol Alcohols, such as 12 propane I or 2-ethoxyethanol, ethylene glycol, n-butane malonate + 6 S methyl ester, ethyl acetate, θ or methyl propionate, etc. — etc. .These, xuan # monomethylarsenic and other subarsenic species and water t 'snails can be used separately. Compared with the soil >', more than one suitable combination can be used. Alcohol — hexaoxane or ¾3 — ethyl ether, tetrahydro Ethers such as ran, M_di-4 1,3-dioxane, isobutyl ketone or P〃-producing methyl ethyl ethyl hydrazone, methyl decahexanone ketones' methanol, ethanol, 2-propanol , N-butanol, glycerine; ethyl alcohol, such as ethyl alcohol, propylene glycol, i, ΓΓ alcohols, and water, etc. These preferred solvents can be used individually for four or two or more. The amount of the refrigerant used may be any amount as long as it allows the reaction to proceed sufficiently. However, the platinum diene complex [2] usually has a capacity of 1 to 200 times. It is more preferable to use a capacity of 1 to 50 times. The manufacturing method i "is preferably performed under an inert gas atmosphere, and the inert gas may be nitrogen or argon. # The optimal reaction temperature can usually be appropriately selected from the range of 25 to 30 (TC (60 to 2000t: 80 to 150 7 is preferred)). Although the reaction time naturally depends on the reaction temperature and other The reaction conditions are different, but the evening is less than 315182 41 200421936 and usually it is from 10 minutes to 72 hours per day. (2 30 days to 48 hours is preferred, and 1 to 12 hours is f ^ (土 、 + »马 更 铨) is suitable to choose the dry fence. Reaction scheme 2

Pt (X) 2 (D) [2]

C2 N

Halogen solvents [3]

Reaction Scheme 2 illustrates the use of platinum diene ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^ Qiu Yi Japanese compound [2] and compound [3] and the use of & the desired halogen atom to the South and abroad This reaction is performed to produce a platinum complex 铷 M y γ,, with a desired halogen atom. (1) (hereinafter referred to as "platinum complex [Id"]) "(hereinafter referred to as" manufacturing method 2 "). 4 white complex [1 d" 1 Corkscrew A _, x Winter turnover dilute complex [2], compound [3] and halogen agent for introduction of desired halogen atom / ten purpose, mixed in the presence of a suitable solvent 'as required under an inert gas bamboo shoots tick lice It can be easily produced by the reaction. 1. The platinum-ene complex [2] and compound [3] are reacted in the presence of an appropriate solvent under an inert gas as required. After the reaction is completed, The product will be isolated by processing, etc., and then #Up will be obtained, in the presence of a suitable solvent, & under inert gas as needed. And the desired halogen film for introduction; '' Neutral + the halogenating agent used for the reaction can easily obtain the platinum complex [Id ,,]. In this case, the platinum diene complex [2] and the compound [3] obtained from the reaction The compound can also be subjected to post-treatment such as single ionization, and the halogenated agent (i.e., the platinum complex can be produced in a single batch) [Id ,,]. In addition, it can also be dissolved in the solvent and then added with the solvent. And the reaction system of the compound [3] can be directly added to the reaction), which can be more efficiently and easily added to the halogenating agent as it is. The reaction system is added. In addition, the agent used in the above manufacturing method can be added as required. The type of halogenating agent and the amount of the preferred halogenating agent are used for the platinum complex [1, Generally speaking, it can be appropriately selected in the range of! To _ equivalents (... to 20 equivalents is better, and] to 10 equivalents is better. ≫, Zeng Zai, the toothing agent used therein, As mentioned earlier, because it is a halogenating agent for V to enter the desired dentition atom, it is of course corrected 3. That is, when uC1 (chlorine atom) of platinum: dilute complex [2], the dentifying agent is used. Chlorinated emulsifiers) other oxidizing agents (fluorinated compounds, deserts or eucalyptus, etc.). The same: when X-F (11 atoms), the fluorinating agent (gasification) is used as the chemical agent. Yin Buzhi Halogenating agents (such as chloride, bromide, or sulphide) (broadening agents), halogenating agents are halogenating agents other than brominating agents (bromides). Fluorinated chlorides or reading compounds, etc.), (hard atoms), the halogenating agent is a halogenating agent (fluoride, chloride or bromide platinum monoene complex) other than iodinating agent (iodide) [2 And the amount of the compound [3] are the same as those of the manufacturing method Γ, and the type of the solvent is the same as that of the manufacturing method 1, and the medium. As long as the amount of the medium used is sufficient to allow the reaction to proceed sufficiently, the amount There is no particular limitation, however, when the platinum diene complex [2], the compound] and the densification || two copies, said / V r-e, etc., once there is a h-reaction, and the platinum diene complex [2] In the case of chemical compound 43 315) 82 200421936 [3] first reaction, the amount of solvent used is the same as that in the manufacturing method. In addition, if the platinum complex formed by the reaction of the platinum diene complex [2] with the compound [3] is once isolated, the amount of the solvent in the subsequent reaction is usually from 1 to 2 for the platinum complex. It is appropriately selected within a range of OO times the capacity (and preferably the capacity is doubled). Reaction κ such as mono-analyte complex [2], compound [3] and halogenating agent should be mixed, and the inverse temperature and reaction time when platinum diene complex [2] reacts with the compound in advance, and the manufacturing method丨 ,, and the same. The reaction of the platinum a complex [1] and the halogenating agent in the case where the wrong a substance [1] is once separated is described in 0 ς, μ.尻 逋 Hanging k 25 to 300 ° C (and 60 to 2000t: better, 80 to 150. Guangyan φ &, ^ & C is more suitable) The reaction room is normally selected; the reaction room usually ranges from 10 minutes to 7 hours. &Quot; The owner 72 is small (and 30 minutes to 48 hours is better, and 1 to 12 hours is better). In addition, the reaction of the succindiene complex [2] with the compound [3], and the subsequent depot transfer with the halogenating agent, ... is carried out in the first batch of Table, the reaction time is the olefine complex [ 2] Minutes after the reaction with the compound "-Kiss [3] (30 minutes to 48 hours J ^ pay is better, 丨 12 hours as a more halogenated agent added to anti-coupon φ # # Also live) Jun It takes 30 minutes to 48 hours] 4 (while stables, 1 to 12 hours is more preferable). The reaction is carried out at any position of the manufacturing method 2 ". Method, if necessary, can be combined with ultrasonic generation, and any method can also be carried out under the inert gas atmosphere ... j Μ ^, month, soil milk pull (which is better 'and inert gas spotting', /, Clothing making method 1 is the same as in the example. Reaction 315182 44 200421936

Reaction Scheme 3 is a description of a manufacturing method (hereinafter referred to as a manufacturing method) of using a platinum complex [丨 "] as a raw material compound to manufacture a hetero complex [1 d]] (a platinum complex having a desired halogen atom ΠΊ). 3 ,,). The white complex [1 d ”] is the surface complex [Γ '] obtained in the above manufacturing method 1 in the presence of an appropriate solvent (if necessary, under an inert gas atmosphere) and for introduction into the desired The halogenating agent used for the halogen atom can be easily reacted by ° The type and amount of the halogenating agent, the type and amount of the halogenating agent and solvent used, the reaction temperature and the reaction time are the same as those of the halogenation in the manufacturing method 2. The steps are the same. In the manufacturing method 3 ", it is also possible to perform a reaction using an ultrasonic generating device as required. In addition, the manufacturing method 3 "is preferably performed under an inert gas atmosphere, and the inert gas is the same as that exemplified in the manufacturing method 1". Production Example 3, In, if the platinum complex in which X is chlorine in general formula [1 "] is reacted with an ilizing agent used for the introduction of a tooth element other than chlorine, the general formula [1e"] can be produced. Representation of the wrong composition: 315182 200421936

(In the formula, ring I, ring I, and ring are the same as above; χ] represents a fluorine atom, a bromine atom, or an iodine.) The above-mentioned production method 丨, to 3 "double dilute complex [2] With compound [3], 'commercially available products' can be used or they can be produced by a suitable method. The complex obtained in this way can be post-treated, isolated and purified as required. The method of post-treatment is, for example, Extraction of reactants, filtration of precipitates, crystallization from the addition of solvents, and distillation of solvents, etc. These post-treatments can be performed separately or appropriately in combination. The methods of isolation and purification are, for example, column chromatography, Recrystallization, sublimation, and the like can be performed independently, and can also be appropriately used in combination. On the other hand, the platinum complex of the present invention represented by the general formula [1 '' '], for example, 3, can be obtained by The platinum diene complex represented by the general formula [2b] is reacted with the compound represented by the general formula [3] to become a platinum complex compound represented by the general formula [ic ,,], and then And the general formula [4] EMgX2 [4] (wherein E represents an aryl group which may have a substituent or an aryl group which may have a substituent Heteroaryl 'X- represents a halogen atom) is obtained by the reaction of the Grignard reagent represented by the general formula [1]. The novel complex of the present invention represented by the general formula [1], for example, is also 315182 46 200421936. 5] M2PtX4 [5] (In the formula, M represents an alkali metal eyebrow, mm: _ prime atom on the compound disk) The only compound represented by the above general formula [3] is anti-palsy, also + 4, reaction 'Becomes the uranium complex represented by the above general formula flc ,, l, and then the formula [lc] is obtained. Λί4] The Grignard reagent represented by the formula is the same, and the general formula [1 ,,,] represents The origin of the complex * 4; For example, the platinum compound represented by the above general formula [2b] can be converted into the quinine reagent; *, and then 1 s " Oral formula [4] The grid film J Han I, .k is obtained by the above-mentioned one. The compound of the formula [M represents a compound reaction, a complex, can be produced by the following fi manufacturing method 1 ,, to manufacturing method 3 ,, The manufacturing method r of the 甶 甶 歹 clothing, the platinum _ timidity represented by the general formula [2b] above ^ ^ first known complexes such as two gas · two two you), and the above General formula, ~ eight tables For example, the ratio of the compound is determined. For example, in a 2-ethoxyethanol base group, such as a private acetonitrile compound, the reaction temperature is 50 C to 150 C (and 80 to} 2〇 ^). (Quanyu) under stirring for 1 hour to several days (preferably 2 hours to the factory day) to reverse the transmission of the order to the platinum complex compound represented by the above formula "1 c ,, 1, such as chlorine (6 · benzyl · 2,2 t] pyridine) platinum. Then, the photocatalyst is reacted with a Grignard reagent such as phenylcyclohexyl compound represented by the above general formula "41 本 _ ， I formula [4]" at the reaction temperature. To 100t (and 20 to E is better). Minutes to 4 hours (and preferably hours) to allow the reaction to proceed to the platinum complex of the present invention represented by the general formula U, such as [6-phenyl-2,2'-bifluorene ratio chelate ( C, N, N)] Bunky stick). These reactions are preferably carried out in an emotional gas such as nitrogen 3I51S2 47 200421936 or argon.

A platinum complex such as potassium tetrachloroplatinate represented by the general formula [5] and a compound such as 6-phenylbipyridine represented by the general formula [3] in a solvent such as acetic acid at a reaction temperature of 5 ( TC to 15 (TC (and preferably 80 to 120) for 1 hour to several days (and preferably 2 hours to 2 days) to obtain a platinum complex represented by the general formula [lc ,,] A substance such as chloro (6-phenyl2, _- pyridine) platinum is then reacted with the above-mentioned manufacturing method 1, and the Grignard reagent represented by the above-mentioned general formula [4], to obtain the general formula [丨 ,,,] represents a complex of the present invention, such as [6-phenylbipyridyl (C, N, N)] benzyl (Π). These reactions are carried out under an inert gas such as nitrogen or argon. Medium is better ... Milk such as dichloro (1,5 • ring platinum dioctadiene represented by the above general formula [2b]) platinum, and Greiner reagent such as benzyl represented by the above general formula [4] Magnesium evolution, at a reaction temperature (re to) 0 (rc (and preferably 20 to 80 t)): 30 minutes to 4 hours (and preferably 3 to 3 hours) to obtain gas ( Aryl) (1,5-cyclooctane dilute) chains, followed by Let the obtained compound be a compound represented by the above-mentioned general formula m, such as 6-phenyl_2,2, _bi-sneeze, at a reaction probability of 0C to 200C (and preferably 80 to 110t) 2 hours to 5 hours (and preferably 18 hours to 3 days) are used to conduct the reaction, and the compound of the present invention of the above general formula Π ,,, and ^ may be superposed. These reactions are inert such as money It is better to carry out in gas. ^ Furthermore, the general formula called “Zouyou dilute complex” refers to a starting compound such as tetrazolium, "a and two fields, such as], 5-dioxin or ... Ene 315) 82 48 and so on, such as acetic acid, 2-ethoxyethanol temperature SOHMOt, and heated 15 in the "Temperature solvent" to obtain reactively. Knife, within 3 hours, it can be easily used as the raw material. In addition to the platinum compound, potassium tetrakidronate and tetrachloropyrrolate, etc., it can also be 1 potassium ^, but it can also be, although acetic acid, 2-ethoxyethyl can be used for their hydrates. It can be used as a reaction solvent in isotropic, volume, and neutral force = & _ 2 acetonitrile, etc .: "Add water to the agent to become an aqueous solvent for reaction. The light-emitting element of the present invention will be described. [] Table The complex of the light-emitting element of the present invention is only required, and the use of the complex element of s-platinum complex is lacking: "There is no special method or form of use, etc. ^ Electric =: complex-emitting An object, or a combination of materials and materials, is better. = The light-emitting element that is characteristic is, for example, an organic EL element. ^ ^ The light-emitting machine layer of the present invention is a complex compound represented by the formula 明The formation method is not particularly limited, however, electricity, electron beam, electron beam, molecular lamination method, coating method, or inkjet / wanxing method can be used, and it is more preferable to use only one coating method from the aspect of characteristics. "The surface of ... resistance heating steam ore and the platinum complex compound represented by the general formula []] of the present invention emit light 2 'is to form a light emitting layer between the anode and the cathode-the counter electrode or contains The elements of the plurality of organic compound thin films can also be protective layers in addition to the light-emitting layer. Second: the transmission layer, the electron injection layer, and the electron transport layer. There can also be substances with other functions 315182 49 200421936 between the layers. The formation of each reed β, can use various materials. The anode is used to supply positive holes to the positive layer. The anode layer, the positive hole transport layer, and the light-emitting layer can be used. The function function is good. For example, the material family on oxygen ^ y is more commonly known as ITO), etc. 4.8 s Indium emulsified indium tin (hereinafter abbreviated) Si V-electric metal oxide, or gold and these metals and Niji Nisi Metal, or with iodized steel or this. Materials or laminates, or J ^ Shiguahua Tongsi inorganic conductive material ~ or polypyrrole and other right β β or ♦ female, polythiophene this month looking for organic conductive materials, of which conductive metal oxide is preferred And: two degrees, stacked layers of temples, and transparency, etc. are particularly good in terms of productivity and southern conductivity Q. The anode film is appropriately selected to be 5 π π water-like sequence "I near material π 5 can often be 10_ to 5 / ^ 50nm to]" m is better, with 1f) n dry surrounding, and It is more preferable to use 100nm to 501 for the anode and the animal.% Poles are used on the soda-lime glass " board etc. to form # # bismuth is broken or the transparent resin base is less soluble from the glass. For ions, use # 用 / 对. In order to reduce lime and break glass, it is better to use two = glass without inspection. Also, use the thickness of the plate,… = stone, etc. to block the coating is better It is only necessary to keep the mechanical strength less and restrict it. However, when using broken glass, it is usually 0.2mm or more, and any person that is 0.7mm or more is ashamed, and the anode is used in the production of anodes. Although it can be used with various materials ... various methods, but α is used for ten months, as an example, you can use electron inflammation, seven, and five methods, resistance heating evaporation method to remove, sputtering dispersion coating, etc. 丨/ Pre-reaction method (sol-gel method, etc.) and ϊ Τ 0 s ^, / to form a film. The anode can also be used to lower the y and p locations of the element by using a method other than washing. Improve luminous efficiency. For example, in the case of 315182 50 1 but 〇, use Uv_ since fruit. Six milk treatment and plasma treatment will have a significant effect on the cathode for lightning; / layer, etc. / / should go to the electron injection layer, The electron transport layer and the light-emitting layer are selected under the close contact of the adjacent layers of the stack, such as the electron-in layer, the electron-transport layer, and the light-emitting layer, etc., and the beach potential and stability. The material of the cathode can be selected. Plutonium compounds, metallurgical compounds, alloys, metal halides, metal oxygen ^ ± A blade ^ mixture of temples, such as lithium, sodium, metal and complex compounds lost by Zhongsi, eight or eight emulsions, magnesium The so-called alkaline earth metals and fluorosilver alloys such as calcium and calcium: their: two potassium alloys or their mixed metals, the town's function function "v:; ::: and rare earth metals such as thorium. . It is more preferable to use aluminum, lithium-aluminum alloy, or mixed metal with temple, or A ^ — silver alloy or mixed metal thereof, etc. The cathode may also be a laminated structure containing the above compounds and mixtures. The thickness of the yin ^ plate can be appropriately selected with the dead material, and is usually in the range of [] to $ " ⑴ 之 摩 has been around, and preferably 50nm to 1V m, and 100nm to 1 μm is better. The cathode of the cathode, #, can be electron beam method, subtractive plating method and resistance heating strip plating method, or all belong to Zhuang. '^ Genus hunting is deposited by early body, and more than two ingredients can be deposited at the same time. Elimination, π μ > ^ ', a plurality of metals are simultaneously vaporized to form an alloy with ° °, and a pre-prepared alloy can also be evaporated. The cathode and anode are preferably the ones with lower film resistance. 〆 & The material of the light layer, as long as an electric field is applied, a layer having the function of injecting electrons from the anode L / Za / main entrance layer and the positive hole transport layer to provide a place where positive holes and children are combined and emit light is provided. Can be any material 315) 82 51 200421936. The light-emitting layer can be doped with fluorescent materials and phosphorescent materials with high luminous efficiency. For example, benzo derivatives, triphenylamine derivatives, benzoμ derivatives, and benzothiazole Derivatives, "Vinyl Styrene Derivatives, Polyphenyl Derivatives, Dibenzyl Butadiene Derivatives, Tetraphenyl Butadiene Derivatives, Naphthimidine Derivatives, Cumarin Derivatives' Perylene (pery) ene derivative, Benzone derivative H derivative, Nitrogen (other than e) derivative It scented organisms, 3 isopadiene derivatives, stilbene anthracene Derivatives, 嗤 or. Styrone derivatives, D Billot parallel mouth bite derivatives, 嚷 二 嗤 and bite bite = , Styrylamine derivatives, aromatic dimethylene materials, 8_: metal complexes of linol derivatives or various monsoon complexes represented by rare earth complexes, etc., or polythiophene, poly Its successes include A + benzyl, polyphenylene methacrylate, silane compounds, organic silane derivatives, etc. Among them, stealing the above-mentioned materials—species of the invention—the structure of the “intersecting layer” can also be the same — Group by, or — Multiple layers formed by a single province, only ^ ^ 5 and formed by a plurality of layers ~. Although the film thickness of the% light layer is not particularly limited, "㈣ the range of melon is better, and 5 is Better. In the production method of the light-emitting layer, although it comes to _ Hosoda + there is no special limitation, but it can be built: pen writing method, ore reduction method, resistance heating steaming method: cloth method (spin coating method, tweezing method and dip coating method) Methods such as "method, main Φ ^ ^ Beme method and LB method" Among them, resistance heating vaporization method and coating method are preferred. The materials of the square positive hole injection layer and the positive hole transport layer are found in the positive hole. Function, the function of rotating positive holes; /, It has the function of injecting electrons from the anode, and any material can be used. Specific: and resistance:?: Triazole derivatives, oxadiazole derivatives,- , Biology, Biology, Imidazole derivatives, 315182 200421936 ♦ Aryl derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amine-substituted Chalcone derivatives, styrylanthracene derivatives, ketone derivatives, hydrazinone derivatives, stUbene derivatives, azane derivatives, aromatic tris Tertiary amine compound, styrylamine compound, aromatic diimidene compound, oxoline (por phyrin) -based compounds, poly-stone-fired compounds, poly (N-vinyl) derivatives, aniline copolymers, thiophene oligomers, and conductive polymer oligomers such as polythiophene, organic boot derivatives , And the platinum complex compound of the present invention. Although the film of Wusi positive hole injection layer and positive hole transport layer is not limited in particular, it is ^^ up to, and is in the range of 1nm to 5 # m. 5 nm to 1 ^ is better ^ ... ^ π flat soil 1 is more preferably 10 nm to 500 nm. Among them, the positive hole injection layer and the positive hole transport sound " 乂 ^ 〇I increased as The single-layer structure formed by one or two or more of the above materials can also be used as a "multi-layer structure formed by a plurality of layers of one composition or different compositions. The method of making the tie / main entrance layer and the positive hole transport layer, Vacuum evaporation method, secondary method, cold dragon injecting the above-mentioned positive hole injection transport agent to dissolve or disperse it in the solvent "soil cloth method (¼ coating method, casting method, dip coating method, etc.) and inkjet method can be used. XI method B inch 'can be dissolved or dispersed together with the resin component, resin component example " J 士 来 气 乙Polyene, Polycarbonate, Polystyrene, Hydrolyl Acrylic Acid, Imada Butyl Methacrylate, Polyester, Poly Maple, Polyphenylene Oxide, Polybutylene, Poly (N -Vinyl yesterdayazole), hydrocarbon resin, ketone tree a, oxy resin, I S & s girl, ethyl cellulose, ethyl acetate, AB S resin (acrylonitrile · butane # one return, (The vinyl resin), alkyd resin, epoxy resin, and stone ketone resin, etc. As long as the material of the electron injection layer and the electron carousel layer has the function of injection from the cathode 53 3I5I82 200421936 into the bun, the function of conveying electrons, and The function of blocking the positive hole injected from the anode can be any material. The positive hole having the function of blocking the injection of positive holes from the anode blocks the handyman; the ionization potential of the ^ layer can be selected to be higher than the ionization potential of the light-emitting layer. Specific examples thereof include triazole derivatives, oxazole derivatives, polycyclic compounds, heteropolycyclic compounds such as copper cuproln, succinyl derivatives, Phylline I bamboo bio, diphenyl diamine ^ Dimethane derivatives, methane derivatives, aromatic ring tetracarboxylic anhydrides, metal phthalocyanines, thiopyran dioxides, anthraquinone diketone biomimetics, carbodiimide derivatives, xendyl groups Metallic complexes of styrylpyrazine derivatives, phthalocyanine derivatives such as naphthalene, perylene, and 8-quinolinol derivatives. Metallic complexes as ligands. Compounds are representative of various complexes, complexes, organosilane derivatives, and benzylamine complexes. Although the thickness of the thunder, main entrance layer and pen conveying layer is not limited, it is usually ... Hanging in the range of 1nm to 5 // m, and preferably 5nm r1 // m, 10_ to __ is better. Among them, the electron 2 :: and the electron transporting layer may be a multilayer structure formed of one or two of the above materials with a shape of: layer structure k 'or a plurality of layers of the same or different composition. The formation method of the lightning layer and the electron transport layer can be the dioxin method or the LB method, the above-mentioned positive hole is injected into the transport agent to dissolve, or the method of ridge medium coating method (spin coating method, casting method, dip coating method, etc.) And inkjet gas goes. When applying the coating method, it can be dissolved or divided together with the resin component == The components can be used in the case of the positive hole injection layer and the positive hole rotation layer. Only stay for 4 and 6 ’As long as it has the function of inhibiting moisture or oxygen to promote the inferior components 315182 200421936, any material is suitable. Specific and +, such as indium, tin, lead, gold, silver, copper, aluminum, titanium and nickel and other metals, oxidation :, silicon oxide, aluminum oxide, germanium oxide, nickel oxide, calcium oxide, barium oxide, three Metal oxides such as ferric oxide, dioxin trioxide, and titanium oxide, sharpen metal fluorides such as hafnium, lithium fluoride, aluminum fluoride, and calcium fluoride, polyethylene, polypropylene, and polymethyl acrylic acid. , Polyimide, polyurea, polytetrafluoroethylene, polychlorotrifluoroethylene, polydichlorodifluoroethylene, copolymers of chlorotrifluoroethylene and dichlorodifluoroethylene, tetrafluoroethylene and containing at least one copolymer A copolymer obtained by copolymerizing a mixture of monomers, a fluorinated copolymer having a cyclic structure in a main chain of copolymerization, a water-absorbing substance having a water absorption rate of 1% or more, and a moisture-proof substance having a water absorption rate of 0% or less. . The method for forming the protective layer is not particularly limited, and examples thereof include a vacuum evaporation method, a sputtering method, a reactive sputtering method, an mbe (molecular beam epitaxy) method, and a cluster ion beam. ) Method, ion plating method, plasma polymerization method (high frequency excited ion plating method), plasma chemical vapor deposition method (CVD, Chemical Vapor Deposition) method, laser CVD method, thermal cVD method, gas source (gas s 〇urce) CVD method and coating method. Examples The present invention is described in detail below with reference examples and examples, but the present invention is not limited thereto. Furthermore, in the following reference examples and examples, the devices used for the measurement of physical properties are shown below. 1)] H-NMR spectrum: GEMINI 2000 device (manufactured by Varian) or DRX-500 device (manufactured by Bruker) 55 315) 82 200421936 Internal standard substance: reading '2) Organic element analysis ·· CHN coating machine mt_5 type device (manufactured by Yanagi Co., Ltd.) Hook absorption spectrum analysis: v — 55〇 (manufactured by JASC0) 4) emission spectrum analysis ·· F-4500 (manufactured by Yoritsu Corporation) ) "Unless specifically noted in the text, the purity of the product is 100%. Metallic compounds are only available in the manufacture of benzene" Volume 18, pages 3337 to 3341 (1999) (01-gan〇metallics 1999,% The description in p 333m4i) is produced according to the following reaction formula.

N

PdCI2 (PPh3) 2, LiCI j J + II:] ————-

Br Br n " SnBu3 toluene, reflux 3

2.5 g of 1 dibenzyl, 7.9 g of (2-pyridyl) tributylstannane (stannane), 0.60 g of di (diphenylphosphine) dichloropalladium, and lithium chloride were combined in 25 ml of toluene, and refluxed. Stir for 3 days. After cooling to room temperature, it was washed with water and purified by Shixi gel column chromatography. # To 1.4 g of the target compound as a colorless liquid. 'H ^ NMR (CDC13): 〇.22 ^ 7. 29 (m. 2H), 7.59 (t, J-7.8 Hz, 1H), 7.73- 7.87 (m, 4H), 8. · 07 (dd, J = i. 8Hz, 7.8Hz, 2H), 8.61-8. 76 (m, 3 H). ___ ΙιΑ · "3? 5ϋ21 ^^^ Manufactured by Benzhi 315182 56 200421936 In the same manner as in Reference Example i, m5_1.4§, (2-pyridyl) tributylstannane 5. · Hydroxyl and chlorinated ... g were mixed with Toluene 14m). , /, Medium, and sub-reflux for 3 days. Human: After washing with water, # purified by w column chromatography to obtain: the target compound Ug as a white solid. Where j is 7'HsT7R (CDCl3) 22-7 ····, 7 ′ t · Η), δ.44 (t, j = i · η), 8 7 3: t, J = 4.8Hz, 1.6Hz, 2H). · 3 (db 曱 i i i by the same method as the reference '' 2,4_ dimobenzyl, ㈣ phenyl) tributyltin m 仏 tribenzyl) dichloride .... 8g In the toluene chest, and refluxed for 3 minutes to cool:: After warming, washing with water ## Purified by Shixi gel column chromatography to obtain 2.9 g of the target compound as a colorless liquid. 7 · 0 9-7. 27 1 (dd , J-2. 62, 1 H), 8. 6 4 JH ^ NMR (CDC 1: δ 3. 9 2 (S, 3H) (m, 3H), 7.67- 7.87 (m, 4H ), 8. χ Η 2 > 8. 6 Η ζ, 1Η), 8. 3 7 (d, j = 2. 4Η 8. 7 4 (m, 2 Η). 4 Platinum complex Π, 1) In the following example, 28 g of i, 3-bis (2 ludinyl) benzyl and 0.5 g of potassium tetrachloroportate produced in Reference Example i were mixed in 10 ml of acetic acid and stirred at 80 t for 3 days. After cooling to room temperature, The precipitated solid was filtered and dried to obtain 0.44 g of the platinum complex (], 1) dihydrate as a yellow solid. Elemental analysis: Calculated (C 3 8.60; Η 3.04;) ττ 5 63) 315182 57 will get the reduced Γ value (C 3 8.27; H2.94; N5 · 50) Tetrahydrogen (1M) dihydrate 0.20g and ethyl magnesium chloride,: s / hydrate (LOOM) 1.31111 mixed with tetrahydrofuran I0ml. Stir for 2 hours. After the reaction solution is extracted with dichloromethane, the D-tube is reduced to a yellow solid crystal tube (a methane / methanol = 1/0 to 20/1) to obtain a version of the target compound. (L, -l) 0.10 g. Elemental analysis: calculated value (C41.61; H2.40; N6.07) found (C 41.58; Η 2.35; N 194) ~~-Chunong Jinnong L1 2) The mixture obtained in the first half of Reference Example 4; the dihydrate produced from the dextrose compound (1M), and the phenyl! Tetramethylfuran solution (i 〇4M) of the US desert was mixed with 4mi :! '22 ..., heated under reflux for 3 hours. After taking the reaction solution with dichloromethane and chloroform, neutral chromatography was performed (dichloromethane / methanol = 1/0 to 20/1) The target starting complex u, 40-26 g was obtained as a yellow solid. Ή-NMR (DMSO-dfi): 5 7 3 2 (t! J =? 7HZ (1H) > _ 5 2-7. 5 5 (m '2H), 7 .... d, Bu 7 · 7HZ, 2H), 8. 10—8 · " ⑹' 2H), δ · " (", jq. 6Hz, 7. 9Hz, 2H ), 9. 27 -9. 40 (m, 2H) Elemental analysis: Calculated value (C 3 7.96; H219; Ν53 · 53%) Measured value (C 37 · 89; Η 2 · 13; N 5.13%) Determination of the solution of the compound In the fluorescence spectrum, the λ max of the fluorescence is 49l.4nm and 523.6nm (CH2C12). Case 6 of the Imperial Examination (Hydrogen, 3, 3, 4 g of Tetrahydropyrene solution of E.ben i.ig] was added to 3 g of magnesium, and 315182 58 200421936 produced phenylmagnesium iodide. 0.44 g of the platinum complex (i'i) dihydrate obtained in the first half of Cangkao Example 4 was added to the solution, and the mixture was stirred at reflux for 3 hours. After cooling to room temperature, the reaction solution was extracted with chloromethane, By performing neutral silica gel column chromatography (dioxane / fase = 1/0 to 20/1), the target platinum complex (l, -3) 0.1 was obtained as a yellow solid. g. NMR (DMS〇-cU): (5 7.36 (t, Bu 7.7HZ, 1H), 7.49-7.52 (m, 2H), 7.77 (d, J-7 '7ΗZ , 2Η), 8 · 10-8 · 13 (m, 2H), 8 · 17 (dt, JL 6Hz, 7.5Hz, 2H), 9.61-9. 71 (m, 2H). Elemental analysis: calculation Value (C 34.73; only 2_G () 'N 5.06%) Measured value (C 34.70; 2.25, N 4.96 ° / 〇) 7 Platinum complex (1'-5) Manufactured in Reference Example 2 Fluoro_3,5_di (2 ′) is 0.4g and 0.68g of potassium tetrachloroplatinate mixed with acetic acid] .4′1 ′ and stirred at 90 ° C for 3 days. Cool to After room temperature, the precipitated solid was filtered 0.56 g of yellow solid was obtained without drying. 0.40 g of the obtained yellow solid and a tetrakis Dfnan solution of phenylmagnesium bromide (1.04M) 2.4m were mixed in 8 ml of tetrahydrofuran, and Learned 3] The reaction solution was extracted with dichloromethane, and the target platinum (dichloromethane / methanol = 1/0 to 20/1) was obtained by performing neutral stone condensation. ^ The yellow solid is called bamboo compound (1, 5) 0 · Π g. 1 Η-NMR (DMS 〇-d «): δ 7 · 5 6-7 s 〇,” 9 (m, 2 Η). 7 ( d J-10. 3Hz, 2H), 8 * 94,

, (M, 4H) Q 7 — 9.4 3 (m, 2 H). 'y · 2 315182 59 200421936 ——HiUALr'j 1) ((6-Momma-2 · 2, dipyridinium platinum dichloride qm) was added to Schlenk's flask [(1 , 2,5,6-77 4) -1,5-Hexanyl] platinum dichloride (jj ^ Goomg, ι · 44,] 0 equivalent) and 6-benzyl-2,2'-linked D Specific bite (4000: ηg, 1.72 ηιπ1, 1.2 equivalents), the inside was replaced with nitrogen. Then, 2-ethoxyethanol (100 mi) was added and heated to disturb under reflux. After stirring for 1 hour for reaction, the solvent was removed under reduced pressure. The obtained red-orange residue was purified by silica gel column chromatography (eluent: monochloromethane / methanol = 20/1), Then, hexane / dichloromethane was recrystallized, and 648 mg (l, '_ 2l) of an orange powder was found to be 648 mg in a yield of 97.4 ° / 〇. Ή-NMR (500MHz, CDvCl.): Δ 7. 10 (dt, J = l. 4, 7 '5 H z > 1H), 7. 16-7. 24 (m, 1 H), 7. 38 (dd, J = 1 4, 7 * 5 Hz, 1H ), 7. 5 0-7. 6 5 (m, 3H), 7. 6 8 (d dd, J = 1.3 Hz, 5. 3, 7. 9 H z, 1 H), 7.88 (t , J = 8 ° H 2 * 1H), 7-94 (dt,] = 7.9, 0.9 Hz, 1 H) 8. 09 (dt, J = " 1 · 6, 7. 9HZ, 1 H), 9 · 0 4-9. 0 9 (m, ih). Excitation wavelength : 330 · 0ηη, fluorescence emission wavelength: 559.4 nm. The platinum complex (1 "-2 5) (76.6, diphenyl gAN) platinum chloride (II)) was reported in a Schlenk, s flask ), [(1,2,5,6ι γ 1 hexamethylene di]] dichloride (11) (500 mg, 1.44 m mol, ι · 〇 equivalent) and 6,6, diphenyl-2, 2. Coupling ratio. Set (5 3 4 mg, 1 · 7 2 mm ο 1, 1.2!), Replace the inside with nitrogen. Then, add 2-ethoxyethanol (25 and heat to reflux). After stirring for 4 hours to carry out the reaction, go to Mingtian under reduced pressure> Gu media. The obtained reddish brown residue was subjected to main chromatography by Shixi gel tube 4 (, '六 315 丨 82 60 200421936, liquid analysis: two Refined with chloromethane) and then recrystallized from hexane / dichloromethane,% to platinum complex Ub as orange powder, 597 mg, yield 77. ! H-NMR (500 MHz, CD2C12): < 5 7. 0 7 (dt > J: = 1 g 7. 5Hz, 1H), 7. l4 (dt, J = i. 5, 7. 5HZ , ιΗ) η 38 (dd, J = 5 >? 5Hz > 1H) ^? 46 ^ 7 5 5 (m, 3 Η), 7.56- 7. 64 (m, 2H), 7.68-7 · 74 (m, '3H), 7 75 (dd, J = i. 3 > Ί 9Hz > 1HK η 95 (t, J =, 8 1Hz > 1H), 8. 〇〇 (dd, j is called 3,7 · 9Hz, 1H), s 0; = 7.9HZ, iH). '' Diphenyl dilinate ^ platinum (im made in Schlenk flask, [(1,2,5,6-77 4) -1,5-hexadienyl] dichloride dichloride (II ) (500 mg, 44 44 1τ1τ100, i · 0 equivalent) and 2, 1, 2 diphenyl one U0-phenanthrene (574 mg, 1.72 mmol, 1.2 equivalent), the interior was replaced with nitrogen. Then, added 2-ethoxyethanol (10 ml) was heated and stirred under reflux for 3 hours for reaction, and the solvent was distilled off under reduced pressure. The obtained red-orange residue was subjected to silica gel column chromatography (solvent Analytical solution: dichloromethane / methanol = 100/1), and then recrystallized from hexane / dichloromethane to obtain a complex compound (1 b-9) 7 0 6 mg, yield 87.2%.] H-NMR (500 MHz, CD2C 12): 6 7. ix (d t > J == 1 4 9-7. 58 7 (m, 1H) '7 '80-7. 9 丄 (m, 5 Hz' 1H) '8 · 42 (d, j = 8 · 6Hz 8 · 5Hz, 1 H) 0 7. 4Hz, 1 H), 7. 1 6-7. 2 4 (m, 1H), 7 ·., (M, 4 H), 7.6 3-7. 7.. 9 6 (d ,: 1 ⑴, 8. 5 0 (d, 8. H) .: 315182 61 200421936 Gold-C, N, N) Chlorinated Button (π)) [(1,2,556-a 4) -i55-hexadienyl] dichloride (11) (500 mg, 1.44 mmol, 1.0 equivalent) and 254,7,9-tetraphenyl were added to a gram flask. -1,10-phenanthroline (837 mg, 1.72 mmol, 1.2 equivalents), the inside was replaced with nitrogen. Then, 2-ethoxyethanol (25 ml) was added and heated, and the mixture was stirred for 3 hours under reflux for reaction, and then the solvent was distilled off under reduced pressure. The obtained red plate-colored residue was purified by silica gel column chromatography (eluent: dichloromethane / methanol = 100/1), and then recrystallized from hexane / dichloromethane to obtain Platinum complex of red-orange powder (lb ,,-15) 988 mg, yield 96.1%. ] H-NMR (500MHz, 7.5Hz, 1 Η), 7.20 5〇-7. 8 0 (m, 1 Η Η) (m, 4 Η), 7. 9 5 (s, CD2C I 2) : 〇7. 1 0 (dt 'J = 1.3, (dt, J = 1.5? Η 5Hz, 1H), 7.' 7 * 8 3 (s, 1H), 7. 85-7. 92 1 H) 0 Pt * In a Schlenk flask, add the #complex (η〇 ((6-benzyl-2,2, -bipyridyl) π, N, N) chloride obtained in Reference Example 8) into a Schlenk flask. Platinum Li Chuan 50000 Qiu, i.⑽ mol 1.0 §) and sodium bromide (8) 1 mg, 5.42 — 〇1, 50 equivalents), the internal ions were replaced with II gas. Then Add 2 · ethoxyethanol. After adding and stirring under reflux for 3 hours, go under reduced pressure:-put, prepare, and extract by silica gel column chromatography (eluate :] Chloroxane / 曱% 5G / 1) Refined to give a red complex compound ("j) ⑷ mg, yield 81.5%. 315182 62 200421936 H-NMR (50 MHz, CD2Ci2 ): δ 7 · 〇9 (6 Η z, 1 Η), 7. 15-7 2 ι r 'J ~ 1 * 4, 7 · 6 H z, 1 H), dd, J = 1.3, 5.3 , 7 · 7 H z, J = 1 (m ^ 1H) ^ 7 · 38 (dd, ^… 7.64 (-, 2H), 7. 66 u H), 8. 〇9 (dt, J = l, 7 7 '7 · 7 · 7 · 9 6 (m, 3-, 1H). The complex "platinum iodide qmxy": Born in a Schlenk flask and added in the same manner as in Reference Example 8 Compound 0 ,,-Chuan ((6-phenyl-2,2, -biazide_C, N, N) pyrene chloride ^ (522mgM.13mm〇M.〇tt) ^^^^ (847mg 5 65mm 〇ij 5.0 eq.) The inside of Shaw was replaced with nitrogen. Then, 2-ethoxyethene UO_ was added and heated, and the mixture was reacted for 3 hours under reflux, and then the solvent was sprayed under reduced pressure. The residue was purified by gel column chromatography (eluent: dichloromethane / methanol = 50/1), and then reconstituted from dichloromethane / ether.

BB (m, 3 Η), 7.7.8 Hz, 1 Η), 8 (m, 1 Η) 0 丨 M Η z, CD 2 C 1 2): (5, J = 1.7, 7. 4 Η z, 4-8. 〇〇 (m, 2 H), δ. 14-8.. 2 5 (m ,: excitation wavelength: 3 3 5.0 nm, fluorescence emission wavelength: 5614 nm. 05-7. 1 4 (m, 8 * 25 (m, 1 Η), 9. 54-9 · 60 m :: -Bipyridinide _ 0 ^ N, N) Platinum (II) iodide) Manufactured in Schlenk flask Added [(1,2,5,6_ π Hong adipenyl] digassed (1)) (300mg '0.862mm 〇], 10 equivalents) and phenyl 63 15 182 200421936 (0) mg, l.034mmoI,! 2 equivalents) and sodium iodide (646 calls, 4.310mm, 5.0 equivalents), the inside was replaced with nitrogen. Then, 2 ethoxyethanol (6ml) was added and heated After stirring for 3 hours under reflux, the solvent was distilled off under reduced pressure. The obtained brown residue was subjected to silica gel column chromatography (eluent: dichloromethane / methanol = 50%). 1) Refining, followed by recrystallization from dichloromethane / ether, to obtain platinum complex (1'3) 4 3 4mg as an orange powder, yield 91.0%.] Physical properties of H-NMR and the like The platinum complexes obtained in Reference Example 13 were consistent. The production was carried out successively. [0,2,5,61 4) -1,5-hexadienyl] dichloride was added to a Schlenk flask. (II) (30mg, 0.862mm, 〇equivalents) and 6-benzyl_2,2, · Lianzhao bite (240mg, as usual, 12 # amount), replace the interior with nitrogen.- Then, 2-ethoxyethanol㈣) was added and heated to reflux for 1 hour, and then filled with steel (646 mg, 4 3 i 〇 〇〇Ι〇ι, 5_〇 equivalent), After stirring at the same temperature for 2 hours, the solvent was distilled off under reduced pressure. The obtained orange residue was purified by silica gel column chromatography (eluent: digas roasting / methanol radon, and then recrystallized from dichloromethane roasting / ethanonium to obtain = orange powder.) Compound (1 ,, _3) 468 mg, yield% 1%. The physical properties of the circle and the platinum complex obtained in Reference Example 13 are the same. From the reference examples] 3 to 15, the results can be judged. In the second stage of the production method of the present invention (Reference Example 13), desired gold complexes can be produced in high yields. However, if a platinum diene complex, compound [3], and a dentifying agent are mixed, The reaction of the manufacturing method of the present invention (Reference Example M) will be able to know the desired platinum complex in a higher search 315182 64 200421936. In addition, J uses the same batch method to determine the manufacturing method of the present invention (Reference Example 1) Ride this to get the desired white complex in higher yield. Platinum moth (π) was added to the Schlenk flask. The platinum complex (Ref, 9) obtained in Reference Example 9 was added. 25) ((6,6, dibenzyl_2,2, _bipyridinyl_c, n, n) platinum chloride ⑴)) (_ g 0.5 5 8 mm 0, ι · 〇 When magic and Sodium iodide (called 418, 2 79 U], 5.0 equivalents), the inside was replaced with nitrogen. Then, 2-ethoxyethanol (15 ml) was added and heated, and the mixture was reacted for 6 hours under reflux, and then distilled off under reduced pressure. Solvent. The residue was purified by silica gel column chromatography (eluent: monochloromethane) and then recrystallized from hexane / dichloromethane to obtain a platinum complex (1, -7) 329 mg, yield 93 7%. LH-NMR (500 MHZ, CD.C 12): 5 7. 0 0-7. 0 8 (m, 2 H), 7 * 37 — 7. 42 (m, 1H), 7.46-7. 5 6 (m, 3 H), 7. 60 ~ 7 * 6 7 (m, 1H), 7. 7 0-7. 7 7 (m, 3H) , 7. 7 8 (d

d 'J = l · 3' 7. 8Hz, 1 H), 8. 0 2 (dd, J = i. 3, 7. 9 H z '1H), 8. 0 4 (t, J = 7.9 H 2, 1 H), 8. 10 (t, J = 7. 8 H 2 > 1 H), 8. 17-8. 3 4 (m, 1H) 0 Example 17 platinum complex (1 ” -1〇) ((2,9-diphenyl-1,10-phenanthroline-C, N, N) platinum iodide (im in a Schlenk flask and added Reference Example 10 to obtain Platinum complex (1 ,, -29) ((2,9-diphenyl-phenanthroline-C, N, N) platinum chloride (11)) (300 mg, 0.534 mm ο 1 ^ 1.0 equivalent) and Elvara (400mg, 2.67 0mmο 1,5.0 equivalents), replace the inside with nitrogen. Then, add .2-ethoxyethanol (1 5 m) 65 315] 82 200421936 and heat it under reflux. After stirring the reaction for 3 hours, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: dichloromethane), and then recrystallized from hexane / dichloromethane. 283 mg of platinum complex (l "_l0) was obtained as a red-orange powder with a yield of § 丨 丨%: 0 7 · 0 6-7 · 1 4 (m, 79-7. 95 (m, 5H) , 5-8. 4 0 (m, 1 H), 8 (d, J = 8.7 Hz, lH) o 2 7 5-NMR (500M Hz, CD2C12) H) '7. 5 0 — 7. 6 2 (m, 4 Η), 7.98 (d, J = 8. 4 Η z, 1H), 8. 2 1 (d, J = 8 · 4 H z, 1 H), 8.53 Excitation wavelength: 324nm, fluorescence emission wavelength · 587 4nm. ~~ rabbit difference · House (-phenanthroline-C, N, N) moth disease white ril)) was produced in a Schlenk flask, adding a reference example; [i] the platinum complex (1 ”-35) G2,4,7, tetraphenyl no-phenanthroline compound ιΝ, Ν) chloride Platinum (π)) (5 μg, 0.700 μb equivalent) and sodium iodide (525 mg, 350,000 μm equivalent) and the interior was replaced with nitrogen. Then, ethoxyethanol (25 ml) was added and After heating for 6 hours under agitation under reflux, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: dichloromethane), and then from hexane / It was recrystallized from dichloromethane to obtain 541 mg of platinum complex (l'15) as a red powder with a yield of 95.9%. 7. Ο 6 — 7 5-7. 9 3 1 Η). 1 4 (m, 2 (m, 5 Η), H-NMR (5 〇 Ο ΜΗ z \ CD2C 1 2): δ, 7 * 52 ~ 7 · 6 7 (m, 14 Η), 7 8 9 7 (s, 1 Η), 8. 26- 8. 42 (m, excitation wavelength · 325η] τι, fluorescence emission wavelength · 614 2_. ~~~ pyridine 315182 66 200421936 (υ [6-phenyl- Synthesis of 2,2, -bipyridyl (C, N5N)] platinum chloride (II)) ci

AcOH

Pt-ci

,, N

\ -J "%-N f IN Pt-CI i! In a Schlenk flask, add [(1,2,5,6-77 hexadienyl) platinum (II) dichloride (500mg, i. 44 mmol) and 6-phenyl-2,2, -bipyridine (400 mg, 1.72 mmol), the interior was replaced with nitrogen. Then, 2-ethoxyethanol (10 ml) was added and heated to 80. After reacting for 2 hours, the solvent was distilled off under reduced pressure. The obtained red-orange residue was purified by silica gel column chromatography (eluent: dichloromethane / methanol = 20/1). Then, it was recrystallized from hexane / dichloromethane to obtain the target compound 648 as an orange powder. The yield was 97.4%. Η), 7. 16 —7 2 4 (m? 1 Η) 5 Η 2, 1 Η), 7. 5 0-7. 6 5 (ιη 3 Hz '5. 3, 7.9 Η ζ, 1 Η ), 7 7 .9 4 (dt, J-7 9, 0 9 Η ζ 6,7 · 9 Η ζ, 1 Η) 5 9 .0 4-9. 〇 (d 1 Η) 8. 〇9 (dt , J = i '(2) Initial complex, u ,,,-2) ([6-phenyl-2,2, bipyridine. Fixed compound (c, n, n)] phenyl platinum (II)) Synthesis ^ 315 182 67 200421936

, N R Q

THF

MgBr > -N V-—J / \ In a Schlenk flask, add [6-phenyl-2,2, -bipyridyl (C, N, N) J weathered platinum (II) (400mg), in After heating and drying under reduced pressure, nitrogen substitution was performed. To this was added 4 mL of tetrahydrofuran, and then a tetrahydrofuran solution of phenyl magnesium bromide (800 mm) was added dropwise at 20 t). The contents become a dark red solution 'and then the mixture is stirred, and the color is gradually stimulated. After the suspension was simmered at room temperature for 3 hours, the solvent was reduced below sakizaki, and dichloromethane was added to the red residue of 2 to add 1% of red water X: and the organic layer was added. Refined by street tube du chromatography_: dichloromethyl oyster). Place the tube part at 40 s, s / b, and add hexane to the bamboo. The crystals were collected by filtration, and dried under reduced pressure. The invention 46 was drawn to 80%, which was the color-repellent powder, '13 matter (l "'-2) 3 7 5mg, and the yield was 85.9%. ^ -NMR (CD2C 12 ) δ: 6. 9 7 ^ ?: · 49 (m, 2H), 7. " (m, 1H 广 6Η) '7 · ...

0. ° '8 · 2 H z, 1 Η), 7. 6 8 (dd J > π, 7 · 6 5 (dd' J, j = 8.2, * 6,7 * 8 H z, 1 H), 8. ⑴, 7.85 ", 0 Hz, 1H), 7 ς · 5, 7. 9HZ, 1 0.9HZ, 1H), 8. 03 (dt, J: (d S3- 8. 56 (m, 1H) ppm. ~ Bundle 佥 ΑΩ: 丄 li1 into (1) one gas (] cyclooctadiene) (n)) combination 315182 68 200421936

AcOH, h2o ^ PtCl ^ fcod) Cang Kao Experimental Chemistry Lecture 4th Edition (Japanese version, Maruzen), i 8 volumes, organometallic complexes, 4 13 pages, 〇g potassium tetrachloroplatinate dissolved in 16mL of distilled water After adding 1 mL of cyclooctadiene and 24 mL of acetic acid, the mixture was stirred at 90 C for 30 minutes. The precipitated cream-colored solid was collected by filtration, washed with water and methanol, and dried to obtain a cream-colored solid m g with a yield of $ 0 · 1%. ] Η-NMK (DMS O-De) δ: 2 3-5.52 (m, 4Η) p pm. 7 — 2 · 5 1 (m, 8 Η), 5. 2 (2) Synthesis of pentafluorobenzyl (1,5-cyclooctadiene) platinum (II) chloride

F

F

Mg ’THF PtCl2 (c〇d)

· &Amp; ... 18— 廿 -shaped / umL · Drip Magnesium

g σ into pentafluorobenzyl magnesium bromide. In: a: Zhongtian Λ F to the two colors π s Lu Liyi add the above (1) a lice (1,5, octadiene) button (11) 〇, in the obtained master reserve one, Liushangan a C is stirred for 2 hours, and the reaction is ended by adding water during the night. — Subtract ,, g β you ν After the soil is removed by the worm, the residue is passed by / 气 模 = 1 / η_ Residual, purified by θ column chromatography (eluent: 曱 1/1), yielded 82.8% as a white solid. 'Product 0.784 g,.! Η-NMR (CDC) 2' 7 2 (in, 4 H), 4 (m, 2 H) pp Ir "〇: 2. 28-2. 8 7 — 5. .01 ( m

4 5 (m, 4 H) 2H), 5… S 2. 6 1 ～

315182 69 200421936 (3) of molybdenum complex (1 ", 1) ([6-phenyl-2- (2-pyridyl) anhydropyridine (Team (:)] pentafluorophenyl platinum (II)) synthesis

Add pentafluorophenyl u, 5-cyclooctadiene) platinum chloride (11) 0.8 g, 6-phenyl-2- (2-pyridyl) pyridine (K3g And 20 mL of acetic acid 'stirred at 80 ° C for 2 days. The obtained orange solution was concentrated under reduced pressure' and purified by silica gel column chromatography (eluent: toluene / chloroform ^ 丨 / 丨) Obtained was 485 g of the platinum complex (1 "M) of the present invention as an orange solid with a yield of 51.7%. JH ~ NMR (DMSO-De) 〇: 7 (dt > J = 1.5, 7.4 Η z) Hz), 7. 6 5 (dd, J = 7 η (m, 1 H), 8. 0 4 (d, J = g 〇Hz, 1H), 8. 25 (dd, j 3 3 ( m, 2 H), 8. 5 2 (dd, 6 — 6 7-6 8 0 (m, 1 H) > 6.9, 7 0 3 (dty J = 1 3, 7 .3, 1 4 H z) 9 7. 6 8-7 7 1 • 0 H z, 1 H) y 8. 1 8 (t 7 J = 8 = 8 0, 0 7 H z), 8 .3 0 —8. J = 8 6, 1 1 H z, 1 H) PP mu ~~~ bipyridyl (1) [6-benzyl-2,2, -bipyridyl ((: 5N, N)) of platinum (II) chloride synthesis

AcOH + n Ra 315182 70 200421936 In a Schlenk flask, 10 g of potassium tetrachloroplatinate (n) and 0.56 g of 6-fluoro_2,2, _bipyridine were added, and acetic acid was added thereto and heated. Keep it at 80. (: Reaction day 2. The reaction liquid was cooled, the red-orange precipitate obtained by filtration, washed with water and methanol, and then dried to obtain 0.95 g of the target compound as a color shifting powder, yield 71.4% ° J = 1.4 , 7. 5 H z, (dd, J = 1.4, 7. 7. 68 (ddd, J = 1., J = 8. 0 H z, 1 H), 8. 09 (dt, J = 1 1 H) ppm〇1H), 7. 1 6-7. 24 1H), 7. 3 8 5 Η z, 1 Η), 7. 5 0-7. 6 5 (m, 3 Η), 3Hz, 5. 3, 7. 9Hz, 1H), 7. 8 8 (t 7.94 (dt, J = 7. 9, 0.9Hz, 1H), 6, 7. 9Hz, 1H), 9. 04 ^ 9 09 (m, osmium platinum complex (i ,,, 2) ([6-benzyl j, 2, · bipyridine (c, n, n)] phenyl platinum (II)) Synthesis

Add [6-phenyl-252, bipyridine obtained in (1) above to a Schlenk flask, add mouth halides (C, N, N)], vaporize (n), 4 g, and 4 ml of tetrahydrofuran, and then benzene 1.7 ml of a tetrahydrofuran solution of methylmagnesium bromide (1 · ⑽m〇] / L) was added dropwise under a nitrogen blanket. After stirring at 20 C for 3 hours, the solvent was distilled off under reduced pressure, and the obtained residue was extracted with dichloromethane. It was purified by silica gel column chromatography (eluent · dichloromethane), and 70 mg of the platinum complex (1 ,, q) of the present invention was obtained as an orange powder, yield 84.8. /. . Reference Example 22 (1 315182 71 200421936 (Synthesis 01 Pentafluorobenzyl platinum (11) > > Synthesis of (1) 6- (2-naphthyl) -2,2 bipyridine Chem. Ber ·, 109, 3864-3868 (1 976) and Tetrahedron Letter, 23, 529 1-5294 (1982)) were operated. In a Schlenk flask substituted with nitrogen internally, 2-bromo was added. 5 g of naphthalene and 30 ml of diethyl ether, and at -50. (: Slowly add 4.5 m of n-butyllithium in hexane solution (1.6 mol / L) and keep it as it is and stir it for} hours, then raise the temperature to 20 ° C And mix for 1 hour. Then, add 2,2, _ Lianzhao bite 〇94g, let fall for 2 hours. Take the solution with material B and remove the solvent, and the obtained oily substance is unloaded with 22 mg of f acid. The acetone solution was just oxidized in ml. The solution was reduced after repeated dehydration, and was purified by Shixi coagulation column chromatography (eluent: methylbenzyl / ethyl acetate, to obtain 0.7 g of the target compound as a white powder. Yield do. • H: _ (C? Ci “: 7 3 6 _7 39 7 * 56 (m, 2H), 7 89-« no / = 9 6 HH 〇2 (1 " '6H), 8.35 (dd, j 6 'I 8HZ, 1H), 8. 44 (dd, Η) ρριτ]. 72 (γπ, 2 (2) platinum Compound (1) M Togo said the synthesis of benzyl sulfonium), "compound (N paste) = above] Reference Example 2. (2) pentafluorophenyl (^ yixin dichloride chloride) synthesized in the same way (II) 0.23g and the orange solution paid above will be concentrated under reduced pressure, (eluent: toluene / gasoline, ^ Column chromatography on W Ma Yan and colored solid of the present invention 315182 72 200421936 0.04 g of facial complex (l ,,, -12), yield 13.50 / O. H-NMR (CDC 1 3) δ: 7. 1 7 (S, 1H)? 7 > 2 3 ^ 7 3 χ: ,, 2H) '7. 4 3 — 7. 4 7 (", 2H), 7. 67-7. 70 (nw, 7. 74 (dd, J = 7. 9, 0.8HZ , IH), 7. 89 (dd 'j (.2, 0.8HZ, 1H), 7. 9 5 (S, called, 7. 9 7-8.0 im, 2H), 8. 06 (dt, J = 1. 6 8 -36 (m > 1H) ppm〇〇H-1H) '8 · 30- (benzyl phenanthroline phenyl # πι)) Synthesis and synthesis in the same manner as in Reference Example 20 The pentyl chloride (cyclooctane dilute) chloride (11) 0.23 § and 2,9-diphenylphenanthroline 0.59 g, 20 mL of acetic acid was added and stirred at 8 (rc 2). The obtained orange = liquid was concentrated under reduced pressure, and purified by slicing coagulation column chromatography (eluent: methoform-1 / 1) to obtain the platinum complex of the present invention as orange η ,, 10λη r ( 12) 0.04 §, yield 12.70 / 〇. 1 Η-NMR (CD 2 Cl (dt, j =} • 4, 7. 3 H z, 1 H), 7. 16 2H), 7. 5 7 (dd, = 8 · 4Hz, 1 H), 7 8 * 9Hz, 1 H), 8. JUHz, 1H) ppm. (c: 2Cl2) ό: 6. 7. ~ 6 .... m, 1H), 6.96.4, 7_ he, 1H), 7.02 ..., J ": 3 '7. 6 3H), 7.45-7. 47 (m' 6H2, 1H),? 8 0 (d, j only Q u ^ WJls B,:, 1H), 8. 4 5 (d, J 2 8 8. 7Hz, 1H) (m, 2H), 7. 9 7 ( d, J = 8.51 (d > The organic EL device is constructed as shown in Fig. 1. On the top, a positive layer (e), a light-emitting layer (made by Jingcai material and dopant material 315182 73 200421936) (sentence, positive hole block layer (c), electron transport layer (b) and cathode (Al / LiF) (a) structure, anode anode and cathode are connected respectively The wires are formed to form a voltage that can be applied between the anode ⑴ and the cathode (a). The anode (f) is an ITO film and is coated on the glass substrate (g). A positive hole transport layer (e) uses the following compounds (a- NPD), a thickness of 40 nm was formed on the anode by vacuum evaporation.

The light-emitting layer (d) containing a host material and a doped phosphorescent light-emitting material uses the following compounds (CBP), respectively

/ Compound (1, _2) passed in Exam 5 (Example η, Two (,) (Consistent Example 2), or Compound α-υ (Consistent Example 3) obtained in Reference Example 20 The vacuum evaporation method was used to form a 35-nm-thick layer on the positive hole rotation layer (e). The positive hole block layer was prepared by using the following compound (BCP), and the light-emitting layer (d ) Is formed to a thickness of 40 nm .... 315182 74 200421936

The electron transport layer (b) is a 5_thick cathode that expands Alq by vacuum vaporization. It is a layered body of 0.5nm ^ and 16〇111 " A1 in order from the electron transport layer side. Make up. In addition, when the organic compound layer and the cathode layers of the organic EL element manufactured in this embodiment were vacuum-evaporated, the degree of vacuum was 8 × 10-5Pa. ...... When a positive voltage is applied to the anode (f) side of the organic EL element that is served, and a negative voltage is applied to the cathode (f) side, it is used. In the case of the object (1 _2) (example), it can be confirmed that the light can be stably emitted from non- =. In addition, it can achieve H m fly with very high brightness 4 pieces with a voltage other than 5v. (0 inch is δ.3% high efficiency. In addition, green light emission (emission tip per wavelength: 500 fine) due to the light emitting layer (d, used compound (1,2)) can be obtained. ':' N) In the case of using the compound (H) (Example 2), it can be confirmed that:!: 丨 Low electricity can stably produce yellow light emission. The light emission spectrum obtained by the organic rainbow element is similar to that obtained by evaporation on a quartz substrate ( ι ”_ 21) and the light-emitting layer formed by CBP and the light-excitation light emission of the separate film are due to the reason that the organic EL element can obtain the light emission caused by the light-emitting layer (21) used in the light-emitting layer. Moreover, the light-emitting layer ⑷ As for a single film, as a result of analyzing the time variation of the luminous intensity of the illuminated version of Okita Shot, it can be calculated that the life of the broken state of the 315182 200421936 4 light source is 2. 8 # s, which is obviously observed from the organic EL element of the present invention. The luminescence phenomenon is phosphorescence. The external quantum efficiency (from The ratio of the number of photons emitted from the outside of the device to the number of electrons injected into the device is calculated), and the efficiency is 22% at a brightness of 100 cd / m2. Electricity is repeated, iii) When the compound (^) is used (Example 3) As shown in Table 3, the luminous quantum efficiency of the element is the second rate at the brightness of 100cd / m2. In addition, only color-to-color emission due to the compound (1_1) used in the light-emitting layer (d) (light emission peak wavelength: 554 nm) can be obtained. 〇Organic made from the compound (1,2) in Example 1 The characteristics of the device are shown in Table 1 for the characteristics of the organic EL device made using the compound (m) in Example 2 and the characteristics of the organic device made using the compound (1), · 丨 in Example 3. Table 1 Element structure characteristics Example number ------_ Positive hole transport layer Light emitting layer Positive hole block layer Electron transport layer CIE color complex point @ 100cd / m2 External quantum efficiency @ 100cd / nf (%) Luminous efficiency @ 100cd / nr 〇nVW) 1 a _NPD 3% (Γ-2): CBP BCP Aiq3 0.26, 0.60 8.3 13 2 -----_ a -NPD 3% (1 ,, -21): CBP BCP Alq3 0.49, 0.50 2.2 2.5 3 a -NPD 3% (Γ, -1): CBP BCP AIq3 0.48, 0.51 3.2 4.3 Rabbit Ghost Examples 4 to 6 Except using compound (], 1) obtained in Reference Example 4 or compound (] 'obtained in Reference Example 6 -3) Except for the compound (], 2) in place of Example], the elements of Examples 4 and 5 were produced in the same manner as in Example]. Also, 3) 5182 76 200421 936 The compound of Example 6 was prepared using 6% of the compound (1'-3). The El characteristics were evaluated. The characteristics of the organic el devices manufactured in Examples 4 to 6 are shown in Table 2 and shown in Table 2. Example 2 Λ Element structure ------- Characteristics Positive hole rotation layer Light emitting layer Positive hole bulk layer Electron transport layer CE Chromaticity point @ 100cd / m2 External quantum efficiency @ 100cd / m2 (%) Luminous efficiency @ 100cdto2 (lmAV) Η <: 1 a -NPD 3% (1,1): CBP BCP Alq3 0 · 26, 0 · 60 6.6 11.1 〇a -NPD 3% (15-3): CBP BCP Alq3 0 · 275 0.60 5.8 6.1 VJ a -NPD 3% (r4): CBP BCP ^ Alq3 0.28? 0.60 5.9 6.3 The clothing has the same element structure as in Example 2, and the light emitting layer (d) ^ 5 objects (1 ,, -2) are doped The amount of the element of Example 7 was $%. Moreover, the element structure was the same as that of Example 2, and the light-emitting layer (d) was doped with a platinum complex (丨 "_3) obtained by referring to J 3% And 6% of Example 8 and Example 9 One by one, a platinum complex (1′1 〇) having the same element structure as that of Example 2 and the light-emitting layer (d) doped in Reference Example 17 was prepared. 3% of the components of Example 10 and Reference Example 18 Platinum complexes (1'15) 3% Example 11 of the embodiment of the element. Evaluate the characteristics of their components. The characteristics of only the organic EL elements fabricated in Examples 7 to π are shown in Table 3. 315182 77 200421936 Table 3 Example No. CIE Chroma Point @ 100cd / m2 External Quantum Efficiency @ 100cd / m2 (%) Luminous Efficiency @ 100cd / m2 (lm / W) 7 6% (1'21): CBP 0.49 , 0.50 2.1 2.5 8 —----—-— 3% (1--3): CBP ----_ 0.50? 0.49 4.3 6.8 9 6% (1 ,, -3): CBP 0.515 0.49 4.4 6.8 10 3% (1-.10): CBP 0.64, 0.36 6.4 3.1 11 6% (1, '15): CBP 0.67, 0.33 4.1 1.0 ^ The result above can be used to determine the organic EL device using the platinum complex of the present invention, Shows very good characteristics. The light-emitting element having the specific orthometallic button complex of the present invention is applicable to various display elements, and is particularly suitable for the production of high-efficiency organic EL element materials. [Brief description of the drawings] ^ ® is a structural example of an organic EL element using the first complex of the present invention. (c) ⑷ (e) (g) second electrode (metal electrode, cathode) (b) electron transport layer i-hole block layer and doped material (d ope) material (f) first electrode (transparent electrode, Anode) light emitting layer (host material i-hole transport layer glass substrate 3151S2 78

Claims (1)

200421936 Patent scope: A light-emitting element represented by a platinum complex containing one or more of the following general formula [n [1] Any of the substituents in clothing A, ring B, and ring c must be coded to indicate a nitrogen-containing aromatic hetero% group whose lice atom is coordinated with a platinum atom. The ¾ 'group with a substituent may be a heteroaryl group with a + group; γ # φ -100 is a halogen atom, or directly bonded or via a deaf atom) or Shifen 2. Atom GS-) bonded aryl group which may have a substituent may have a substitution of Mei Shao 4 ^ — soil τ aryl (restricted condition is that the adjacent two rings are chaotic party. , Y is not a chlorine atom, and the non-adjacent two rings contain a chaotic scented aromatic group 谔 * + and '', Yakiri, γ is a halogen atom)]. 2. For example, the light-emitting element of item 1 of the patent application, wherein the platinum complex compound represented by the formula "Buzhi platinum complex" is represented by the following platinum complex compound represented by the general formula [Γ]: (In the formula, 3 which may have a substituent] 5 j 82 79 200421936 nitrogen-containing aromatic heterocyclic group, ring C] represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent; X represents a halogen atom) . 3. The light-emitting element according to item 2 of the scope of patent application, wherein the button complex represented by the general formula [1,] is a platinum complex represented by the following general formula [1a ']: [la,] (where 'ring c,] represents an aryl group or a heteroaryl group; R], ... and R3 are independent of each other, and represent a lice atom, an alkyl group, an alkyl group, an aralkyl group, an alkenyl group, and an alkyne Aryl, aryl, amine, mono- or dialkylamino, mono- or diarylamino, alkoxy = aryloxy, heteroaryloxy, alkoxycarbonyl, amido, amido Amino aryloxycarbonylamino, sulfonamido, sulfamidino, carbamoyl-pentyl, carbamoyl, arylcarbon, heteroarylthio, sulfanyl, sparite, etc .: Phosphoric acid Amine, mesityl, sulphydryl, selenium atom 'cyano: radical, glass, nitro, hydroxamic acid, sulfinyl, hydrazine, aliphatic heterocyclic, aromatic heterocyclic, Substituted silane groups or polymerizable beauty. Also, a plurality of R] each other, a plurality of feet 2 between each other, and / or a plurality of r3 between each other 'may form a condensed ring with their bonded pyridine ring or ring c; X represents a prime atom and "don't represent a substituent two R- and" the number of ml represents an integer of 0 to 3,] 屮 and claw 3 express. Integer to 4 · ', and heart ... 3 is 2 or more Integer: complex 315182 80 several R, last R2 . R3 from each other a plurality may be identical or different from each) of platinum complexes shown perilous T W J First coat ° to the following general formula [lb,] The platinum complexes represented by: 4. The light-emitting elements such as the scope of patent application (2), the significance of which). 5. The light-emitting element according to item} in the scope of patent application, wherein the # complex compound represented by the general formula ⑴ is a platinum complex compound represented by the following general formula II ,,]: [1 ”] r X (wherein ring B2 and ring C2 are independent and represent a nitrogen-containing aromatic heterocyclic group which may have a substituent, and ring M represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent Also, ring B2 and ring C2, ring C2 and ring A: 'Or every B2, ring (: 2 and ring, each other can also be bonded to form a fused bad, X represents _ prime atom). 3) 5182 8 ) 6. If the light-emitting element of item 5 of the patent application κ encloses 罘, in which the molybdenum complex represented by the general formula ΠΊ is from & : (R3) m3 [la ,,] (wherein, jmr.'s heteroaryl ^ represents an aryl group which may have a substituent or may have a substituent, R and R. Each is independent and expresses an alkyl group, an aromatic p I / Λ tick atom, an alkane Group, haloamino group, mono = diluted group, alkynyl group, aryl group, amine group, mono- or dibasic group is formed into one amine group, alkoxy group, alkoxy group, acid oxy group, acid amine group, hydrazone Carboxamides: milk-based, amine-based, amine-continuous, and amine-based: Carboamino, arylthio, sulfanyl, sulfonyl, urea / cubylthio, heterogeneous, ± tender, Phosphoryl ether amine group, ammonium group,-group, i element atom 1 group, lutein acid group ilyl group, sub-group;. Tertiary group, nitro group, hydroxy post-acid linoleic acid group, hydrazine group, aliphatic hetero Strict—Cyclopentyl or polymerizable groups can be taken; X ^, fragrant heterocyclic group, R3 'can also bond with them to form a ring. Number: R1 and / or plural b, 2 and ring e , s, ask to open / form a fused ring; Also, ring 2 with 2 and 2 and ring a2, ring can also be combined with each other to form a condensed ring; ... C2hA2 R, and ~ ", mi indicates. To 32: respectively The whole religion of substituents · v 1 rz. 4] and 11 ^ 2 or more to each other and a plurality number may be the same two 8 "plural R1 7. The application range of the Patent! * 'X are as defined above). " ", where the general formula is shown in Table 3) 5182 82 [1 ,,,] Xunyou ~ / Into the dagger valley is self-independent, meaning that it may have a substituent or a heteroaryl group that may have a substituent; rings a2 and C 9 NC /, Clothing h, or ring A2, ring c: 2 and the ring & each other may form a fused ring with each other. ^, ，, and A2 'frame B2, ring c2, and / or ring E have taken. Substituent group ~, if the substituent is a g-position or bond-receiving group of the metal, it can be coordinated or bonded by a coordinating or bonding atom in the substituent). S 8. The light-emitting element according to item 7 of the scope of patent application, wherein the general formula. The complex complex represented by is a complex complex represented by the following general formula [Η ,,,]: t3 IX (wherein ring A and private E are the same as above; R1 and R3 each independently 83 represents an alkyl group, a halogenated alkyl group, an aralkyl group, an alkenyl group, an alkynyl group, an aryl group, an amine group, a mono- or dialkylamine Base, mono- or diarylamino, alkoxy, aryloxy, heteroparaxyl, alkoxycarbonyl, aryloxycarbonyl, fluorenyl, fluorenyl, alkoxyquinyl, aryloxyfluorenyl, Fermented amine group, amine sulfonyl group, amine methyl fermented soil; IL group, arylthio group, heteroarylthio group, ruthenium group, submersed glutenyl group, urea Li amine group, ㈣ '㈣, έ 素Atom, cyano, luteinic acid, carboxyl, nitro, hydroxamic acid, sulfinic acid, hydrazine, aliphatic hetero% group, aromatic heterocyclic group, substituted silane group or polymerizable group; , = And ^ can be combined with two of them. Fixed rings together form fused rings; R and ring A2, or 戸 Δ n 3 ν R and%, can form fused rings together; m] my knife Do not denote the number of substituents R] and r3, m represents a positive number from 0 to 3, and W represents an integer from 0 to 4; and] evening bismuth. Let m and m3 be 2 or more < positive number% , Plural R1 and plural display · You may be the same here or each other. "'' The last several R] and / or multiple R3, can be… 璟 璟 回 回 π 舁 舁, j 吡 broken and other bonded Pi coats /, together to form a fused ring In addition, the third one obtained from its inflammation & A2 and / or ring E generation group can be coordinated with metal or can be replaced by B π—,, and the mongolian bond replaces a guard, which can be replaced by that Can be coordinated or atomic coordinated or bonded in a radical). Atoms and metals of gas, such as platinum, represented by the luminescent element in item 7 of the scope of patent application, < Λ ^ Τ 'general formula Π ,,'] The white complex 3 is the following general formula [lb ,, or: "" Yibu face complex 315182 84 200421936 (In the formula, R1, R2, R3 and R4 are each independently and represent alkyl, haloalkyl, aralkyl, alkenyl, alkynyl, aryl, amino, mono or dialkylamino, mono or diaryl Amino group, alkoxy group, aryloxy group, heteroaryloxy group, alkoxycarbonyl group, aryloxycarbonyl group, fluorenyloxy group, fluorenylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfoxamine group, Amine group, amine group, sulfanyl group, arylthio group, heteroarylthio group, sulfonyl group, sulfinyl group, ureido group, phosphoramido group, hydroxyl group, thiol group, halogen atom, cyano group , Sulfonic group, carboxyl group, nitro group, hydroxamic acid group, sulfinic acid group, hydrazine group, aliphatic heterocyclic group, aromatic heterocyclic group, substituted silane group or polymerizable group; and R2 and R3 , And R1, R2, and R3 can form two fused rings together with their two pyridine rings, or pyridine ring and benzene ring; m], m2, m3, and m4 represent the substituents R1, R2, R3, and R4, respectively Number, m] represents an integer from 0 to 3, m2 and m3 represent integers from 0 to 4, m4 represents an integer from 0 to 5, and m], m2, m3, and m4 are integers of 2 or more, a plurality of R1 , Plural R2, plural R3 A plurality of R4 may be the same or different from each other; furthermore, R1, R2, R3, and / or R4 may form a condensed ring together with the pyridine ring or benzene ring to which they are bonded; In addition, R1, R2, R3, and / or R4 are substituents that can be coordinated with or can be bonded to a metal. 85 315182 5 can be converted to a coordinated or bondable atom in the substituent With metal 1 (such as drink or bond). The light-emitting element according to the first item in the scope of the patent, wherein the light-emitting element is a plurality of organic layers including a light-emitting layer or a light-emitting layer formed between eight pairs of electrodes, and at least one layer contains more than one general formula. 1 i-plane complex. • If applied, the light-emitting element in item 2 of the ~% patent range, wherein the light-emitting element is a compound that forms a light-emitting layer between electrodes, or a plurality of organic strips containing a light-emitting layer, and at least one of which contains more than one Formula [1,] Table 12 & And the light-emitting element according to item 3 of the patent scope, wherein the light-emitting element is a light-emitting layer formed between counter electrodes, or a plurality of organic layers including a light-emitting layer, and at least one of the layers contains more than one general formula [la,] Of platinum complex. ', 13. The light-emitting element according to item 4 of the scope of patent application, wherein the light-emitting element is a light-emitting layer formed between a pair of electrodes or a plurality of organic compound layers containing a light-emitting layer, and at least one of the layers contains more than one general formula [lb ,] Platinum complex. 14. The light-emitting element according to item 5 of the scope of patent application, wherein the light-emitting element is a light-emitting layer formed between a pair of electrodes or a plurality of organic compound layers containing a light-emitting layer, and at least one of the layers contains more than one general formula [丨 "] A complex compound represented by the same. For example, the light-emitting element of the sixth scope of the application for a patent, wherein the light-emitting element is a plurality of organics that forms a light-emitting layer between pen electrodes or contains a light-emitting layer ~ < S6 315182 or more general formulas [la ' '] Surface. At least one of the layers contains a platinum complex as shown. 16 = Please! The light-emitting element of the seventh item, wherein the light-emitting element forms a light-emitting layer between the electrodes or contains a light-emitting layer. A plurality of organic substance layers, and at least one of which contains more than one platinum complex compound represented by the general formula [1 ,,,]. In: The light-emitting element of item 8 of the patent, wherein the light-emitting element is between the two electrodes. Form a light-emitting layer or a plurality of organic compounds containing a light-emitting layer, and at least one of the layers contains one or more platinum complexes represented by the general formula [la ,,,]. 18 :: = The light-emitting element of the ninth item, wherein the light-emitting element II = forms a light-emitting layer or a complex organic molybdenum complex containing a light-emitting layer in between. Layer ... A light-emitting element of any of the above-mentioned general formula [lb ,,] in Table 19 · ^ in the scope of patent application No. 10, Xiyan apricot-i β 18 members. The prerequisite components are organic + 20. ^ 0 Ψ ^ ^ .. The package of prerequisite components (organic £ L · component). The light-emitting element according to any one of claims 1 () to t, ^ ^, and 19 of the patent application scope, wherein Y, a platinum compound a of ^ k in the at least one layer, can be used as an organic electric field element. (Organic element). ; ^ The role of each combination of materials 315 182 87