TW200906909A

TW200906909A - Polymers containing sulfo group and intermediate thereof, and organic electroluminescent element containing the polymer

Info

Publication number: TW200906909A
Application number: TW097112290A
Authority: TW
Inventors: Michiru Sekiguchi; Kazuhiko Togashi
Original assignee: Mitsui Chemicals Inc
Priority date: 2007-04-04
Filing date: 2008-04-03
Publication date: 2009-02-16
Also published as: JPWO2008126393A1; WO2008126393A1; JP5372742B2

Abstract

To provide polymers that are favorably usable for organic electroluminescent elements and their intermediates, and a method for producing them, and organic electroluminescent elements that contain the polymers. This invention provides polymers containing sulfo group and their intermediates that are characterized by the structure in which sulfo group is introduced into the polymers that contain at least one repeating unit shown in the formula (1) in the polymer chain. (in the formula, Z1 to Z4 represent substituted groups. P1, P2 represent the whole number of 0 to 5, and P3, P4 represent the whole number of 0 to 4. X1 to X4 represent monovalent aromatic groups, and X1 and X2 or X3 and X4 can be connected with each other to form a ring. Y represents a divalent aromatic group, and Ar1 to Ar4 represent divalent aromatic groups, that can be identical or different from each other. These divalent aromatic groups can be the aromatic groups with rings formed by aromatic groups connected with each other. T1 and T2 represent groups that are chosen from a group of a single bond, - (CH2) t-, -CH=CH-, -C=C-, -O-, -S-, -CQ1Q2-, -CO-, -SO-, -SO2-, SiE2-, that can be identical or different from each other. t represents the whole number of 1 to 20. Q1 and Q2 represent alkyl groups or aromatic groups, that can be connected with each other to form a ring. E represents a hydrogen atom, an alkyl group, or an aromatic group. m, n represent the whole number of 0 to 2. )

Description

200906909 九、發明說明：【發明所屬之技術領域】去，ϋ 關於含崎基之新穎高分子化合物及其中間體。再明係關於含該化合物之有機電致發光元件。【先前技術】地游3來:^於，用有機化合物之功能材料的研究開發正積極丨機化合物作為元件細 enielement:有機EL元細發，有活力 =合產生激子(_)，利用先。有機紐發光元件可於數V〜數十而^ 應用於各種發光元件顯示;权有機電致發光元件，期待最近，由於可利用印刷法圖案化之特徵，就答本咕女^ 物而言’對於使用了共⑽發光高分子=雷有機^合子有機電致發光元件：高分子有機EL 有^1牛(高分200906909 IX. Description of the invention: [Technical field to which the invention pertains] Go, ϋ About the novel polymer compound containing a group of bases and its intermediates. Further, it relates to an organic electroluminescence device containing the compound. [Prior Art] Ground Tour 3: ^, research and development of functional materials using organic compounds are positively active as a component fine enielement: organic EL element fine hair, active = combined exciton (_), use first . The organic light-emitting element can be applied to various light-emitting element displays in a few V to tens of times; the right organic electroluminescent element is expected to be recently used, because it can be characterized by the printing method, For the use of a total (10) luminescent polymer = Ray organic zygote organic electroluminescent device: high molecular organic EL has ^ 1 cattle (high score

面板或可U式顯示n之材料之崎，正在大晝面TV ^有機電致發光元件中，係使用;電该發光層上疊層的電洞輸送層或電子轸 f發光層，或在件特性壽命，一般會鄰接於陽極而使用雷、ζ仁了提高元電致發光元件之中，電洞注入層之材料(洄、;;入H鬲分子有機含為導電性高分子之聚嗟吩衍生物(聚(3 4二二才，）’例如已知稱PEDOT。）與為高分子質子酸之聚(苯 ^^氧嗟吩）：以下之分散液材料(以下簡稱PED0T/PSS。义)(以下稱PSS。）之三芳胺聚合體(專利文獻2)等。文獻丨）’或含有磺基 200906909 ^日本特開2000一91081號公報獻2】中國專利申請公開第助666號說明書【發明内容】發明欲鮮決之問, 劑之二性，為以水作為溶但以水作為溶劑，被以 Γ: .分子量之PSS，因此，亦二t问刀子ED0T ’過度使用高題。再者，且古姑m 亦破礼摘具凝集性難以形成均質薄膜之n C希具望有 =rss之具線入層的㈣有‘於芳= 合;\’於專利文獻2中記載具 _so)、水等極性溶$中一―錄甲^甲醯胺(DMF)、二甲基亞石風但是，對於有機溶劑^容解度並^能種算m製備溶劑之溶解性，及壽ί之化合物之有機電致發光元件’希望在效率儿人i發明之目的在於提供適於有機電致發光元件之新藉古八名解;』其：間體，及含該化合物之有機電致發光元件。、门刀 -解決课韻之方法入4案f8狀等’為了達成上述課題而努力探討，結果發現且無祕性’能軸均質_，藉由使賴 ^ 的有機電致發光元件，乃完成本發明。此伃至I長可〒亦即，本發明提供以下⑴〜(21丨。 ⑴-種含有石黃基之高分子化合物，係為對於在高分子且 ^至少1個通式⑴所示重複單位之高分子化合物導人續基^ 構造。 200906909The panel or the material of the U-type display n, is used in the large-surface TV ^ organic electroluminescent element; the electric hole transport layer or the electronic 轸f light-emitting layer laminated on the light-emitting layer, or in the piece The characteristic life is generally adjacent to the anode, and the material of the hole injection layer is improved by using the thunder and the coix seed, and the material of the hole injection layer (洄;; The derivative (poly (3 4 225), for example, known as PEDOT.) and the polymer protonic acid (benzene oxy porphin): the following dispersion materials (hereinafter referred to as PED0T/PSS) (hereinafter referred to as PSS.) Triarylamine polymer (Patent Document 2), etc. Document 丨) ' or contains sulfo group 200906909 ^Japanese Patent Laid-Open No. 2000-91081 pp. 2] Chinese Patent Application Publication No. 666 No. 666 [ SUMMARY OF THE INVENTION In order to solve the problem of the invention, the second nature of the agent is that water is used as the solvent but water is used as the solvent, and the PSS of the molecular weight is used. Therefore, the ED0T of the knife is too high. Furthermore, the Gu Gu m also has a n-grain-like agglomerate that is difficult to form a homogeneous film, and the n C is expected to have a line of the rss (4) having 'Yu Fang = combination; \' described in Patent Document 2 _so), water, etc., polar solution, medium-to-one, methylidene (DMF), dimethyl sulphate, but for organic solvents, the solubility of the solvent can be calculated, and The organic electroluminescent device of the compound of Shouli 'is hoped that the efficiency of the invention is to provide a new solution for the organic electroluminescent device;": its: the organic body containing the compound Photoluminescent element. , the door knife - the method of solving the rhyme into the 4 cases f8-like, etc. - In order to achieve the above-mentioned problems, we tried to find out that there is no secretive 'energy uniformity _, by making the organic electroluminescent element of Lai ^ complete this invention. That is, the present invention provides the following (1) to (21). (1) A polymer compound containing a fluorescein group, which is a repeating unit represented by at least one formula (1) in a polymer. The polymer compound leads to the continuation of the structure ^ 200906909

(1)(1)

(式中，z1〜y表示取代基;ρι、p2表示〇〜5之整數示。Μ之整數;X1〜X4表示i價之芳香族基，χ1* χ2 Ρχ3【二可=彼，鍵結成環;γ表示2價芳香族篆Arl〜 S i:此ί: ?芳香族基…此等2價芳香族基可為= 族基彼=結^成環的芳香族基。Τ1與Τ2為擇自於單鍵、- CO-、-SO—、」奶c=c—、—0—、—s—、—cqV—、-相同或不同.t表2 S1E厂所構成群組之基，彼此可為可彼此鍵結成絲或芳香族基，亦之整數）表不虱原子、烷基或芳香族基;m、η表示〇〜2 子鏈有續基之高分子化合物’其中’係、為對於在高分基而成的構造1 1彳崎式(2)所示重複單位之高分子化合物導入磺 200906909(wherein, z1 to y represent a substituent; ρι and p2 represent an integer of 〇~5. An integer of Μ; X1 to X4 represent an aromatic group of an i-valent group, χ1* χ2 Ρχ3 [two can be a part, a bond is formed into a ring γ represents a divalent aromatic 篆Arl~S i: this ί: ?Aromatic group... These divalent aromatic groups may be an aromatic group of a group of a group of 结1 and Τ2. In the single bond, -CO-, -SO-, "milk c=c-, -0-, -s-, -cqV-, - the same or different. t Table 2 S1E plant group basis, each other In order to bond to each other to form a silk or an aromatic group, the integer is also a non-halogen atom, an alkyl group or an aromatic group; m and η represent a polymer compound of the 〇~2 sub-chain having a contiguous group, wherein In the structure of the high-division group, the polymer compound of the repeating unit shown in the formula 1 (1) is introduced into the sulfone 200006909

(3)如⑴或(2)之含有磺基之高分子化合物，其中，γ所示基為通式(a—1)所示基。(3) A polymer compound containing a sulfo group according to (1) or (2), wherein the group represented by γ is a group represented by the formula (a-1).

(式中，Q 為擇自於單鍵、0、S、CH2、CMe2、CO、SO、S〇2、 8¾、SiMe2所構成群組之基，k表示0〜2之整數。） (4) 如⑴〜(3)中任一項之含有磺基之高分子化合物，其中，前述P1〜p4至少1個為丨以上整數，前述Ζι〜Z4彼此可為相同或不同、’各表示擇自於綾基、羥基、胺基、單取代胺基、二取代胺基，及通式(la)〜(3a): ~(〇)l -D(la) -〇(C = 〇)-D(2a) —(C-=〇)〇 —d (3a) (式中，D表示無取代或經取代之直鏈狀、分支鏈狀或環狀碳 1〜8之烷基、無取代或經取代之碳數4〜12之〗價芳= 構代之碳數7〜2。之芳烧基’L表示。或丨)所示“ (5) 如⑴〜⑶中任一項之含有磺基之高分子化合物，其中，十 200906909 述p1〜P4各為0。又，本發明包含以下者。 ⑹-種有機電場發光材料，包含⑴至(5)項中任基之高分子化合物。％之3有石頁 ⑺一種有機電致發光元件材料，其特徵在於:將項之含有雜之高分子化合胁騎在麵賴讀^5)中任— 性溶Γ(7)之有機1致發光元件賴，財，前财機溶劑為極 (9)-種有機電致發光元件，係在丨對電極間，鱗 Ξ中任—項之含有磺基之高分子化合物至少1種之層至少1層分子=====+如紐概之高為==)ΐ層有機電致發光元件，其中，前述電荷注入輪送層 (i2m)之錢f致發光元件，財，包含前述電洞注送層至少2層。询 (13)-種兩分子化合物，於高分子鏈巾縣通式⑴所示重位至少1個。卞(wherein Q is a group selected from the group consisting of a single bond, 0, S, CH2, CMe2, CO, SO, S〇2, 83⁄4, SiMe2, and k represents an integer of 0 to 2.) (4) The sulfo group-containing polymer compound according to any one of (1) to (3), wherein at least one of P1 to p4 is an integer of 丨 or more, and Ζι to Z4 may be the same or different from each other, and each of the expressions is selected from Mercapto, hydroxyl, amine, monosubstituted amine, disubstituted amine, and formula (la)~(3a): ~(〇)l -D(la) -〇(C = 〇)-D(2a) —(C-=〇)〇—d (3a) (wherein D represents an unsubstituted or substituted linear, branched or cyclic carbon 1-8 alkyl group, unsubstituted or substituted carbon The number of aryl groups of the number 4 to 12 = the number of carbon atoms of the structure = 7 to 2. The aryl group "L" or "丨" is shown as "(5) The polymer containing a sulfo group according to any one of (1) to (3) Further, the present invention includes the following: (6) An organic electroluminescent material containing the polymer compound of any one of (1) to (5). (7) An organic electroluminescent device material characterized by: Miscellaneous polymer compounding threats riding in the face of the ^5) in the middle - the sexual solution of bismuth (7) of the organic light-emitting elements Lai, Cai, the former machine solvent is the extreme (9) - kind of organic electroluminescent elements , at least one layer of at least one layer of a polymer compound containing a sulfo group in the sputum between the counter electrodes, at least one layer of the molecule =====+ as high as ==) ΐ layer organic electricity The light-emitting element, wherein the charge injection layer (i2m) has a light-emitting element, and comprises at least two layers of the hole injection layer. (13) - a compound of two molecules, in a polymer chain towel At least one of the weights shown in the general formula (1) of the county.

(式中，Z1〜Z4表示取代基;p1、p2表示〇〜5之整數、p3、〆 10 200906909 表示0〜4之整數;χι〜χ4表示1 奸 X4可以彼此鍵結成環;Y表示2價芳香族基X2、X3與或不同，表* 2價芳香縣，又，此“’二此可為相同基彼此鍵結形成環之芳香族基# I 2 ^魏基可為芳香族 —、—CH = CH—、—CeC_ 〜；；—T 為擇自於單鍵、~(CH2)t CO-、-SO-、—s〇 —、_SiP 、—S~、—CQiQ2-、— 相同或不同;t表示1〜^之整數.Ql2及H鱗組之基，彼此可為可彼此鍵結綠E表錢肝基或料族基，亦之整數。）凡丞次方香族基;m、n表示0〜2 (Η)如(13)之高分子化合物，其 (2)所示重複單位至少}個。、甲於同刀子鏈中具有以通式 χΙχ2(wherein, Z1 to Z4 represent a substituent; p1 and p2 represent an integer of 〇~5, p3, 〆10 200906909 represents an integer of 0 to 4; χι~χ4 indicates that 1X4 can be bonded to each other in a ring; Y represents a 2 valence The aromatic group X2, X3 is different or different, and the table * 2 valence aromatic county, and this "' two of these can be the same group to bond with each other to form a ring of aromatic groups # I 2 ^ Weiji can be aromatic -, - CH = CH—,—CeC_ 〜;;—T is selected from a single bond, ~(CH2)t CO-, -SO-, —s〇—, _SiP, —S~, —CQiQ2-,—the same or different ;t represents an integer of 1~^. The base of the Ql2 and H scale groups may be mutually bondable to each other. The green E is expressed as a liver or a base group, and is also an integer.) Wherever the 香香 fragrant base; m, n represents a polymer compound of 0 to 2 (Η), such as (13), which has at least one repeating unit represented by (2), and has a general formula of 于2 in the same knife chain.

(式中，Ζ1 〜Ζ4、ρ1 〜|34、. V4 τ (2) 合物。 (15) 一種錢發光树㈣，、包分子化高分在於·_之 git光兀件，係在1對<1極間，夾持含有(13) 或(14)項之冋刀子|匕合物至少1種 ⑽如(取有機電致發光元件曰& 物之層，為電荷注人輸送層。 -τ mm冋刀于化口 ⑽如⑽之有機電致發光元件，其中，前述電荷注入輸送層， 200906909 為電洞注入輸送層。送層之錢紐發光元件，射，包讀《洞注入輸 (21)—種有機電致發光元件，係夾持含 =二之:r層，並卿)之高得到高效率及長壽命之有機較發光元件。化口物【實施方式】實施發明之噩祛彬熊以下，說明本發明相關細節。本發明之含有縣之於子化合物，係觸於單奴高分子蝴轉人絲而成的 ^，㈣子鏈中至少具有1個通式(”所示重複單位之高分子化 il⑴為其有用中間體(以下稱「中間體高分子化合物」）。(In the formula, Ζ1 ～Ζ4, ρ1 ～|34, . V4 τ (2) compound. (15) A money illuminating tree (4), the GSM optical element with a high molecular weight of the package, is in 1 pair. <1 pole, at least one type (10) of the knives containing the (13) or (14) entanglement (for example, the layer of the organic electroluminescent element 曰 & - τ mm 冋于 (10) The organic electroluminescent element of (10), wherein the charge injection transport layer, 200906909 is a hole injection transport layer. (21) An organic electroluminescence device, which is an organic light-emitting device which has a high efficiency and a long life, and which has a high density and a long life. The following is a description of the details of the present invention. The sub-compound of the present invention is formed by touching a single-nuclear polymer to a human filament, and the (four) sub-chain has at least one formula (" The polymerized il (1) showing a repeating unit is a useful intermediate (hereinafter referred to as "intermediate polymer compound").

(1) 八、入。 (式中，Ζ1〜Ζ4，示，代基;ρί、ρ2表示〇〜5之整數之整數;\〜χ絲丨價之芳香絲、χ1與χ2、以同或不同’表示2價芳香族基，又，=芳香;ί::二 12 200906909 香族基彼此鍵結形成環之芳香族基;τ1與τ2為擇自於單鍵、— (CH2)t— ' —CH=CH— ' —C^C— ' —〇— ^ —S— > ~CQ!Q2 — 一CO—、一SO S〇2 SiE2 —所構成群組之基，彼此可為相同或不同，t表示1〜20之整數;Q1及Q2表示燒基或芳香族某·，亦可彼此鍵結成環;E表示氫原子、烷基或芳香族基;m、n '二〜2之整數。） ' 磺基數不特別限制’每個重複單位之磺基平均數為〇1〜2〇個，較佳為0.5〜10個，更佳為1〜8個。通式(1)中，Ρ1〜Ρ4至少1個為1以上之整數之情形，〜ζ4 7示取代基彼此可為相同或不同，各為擇自於羧基、羥基、胺基、早取代胺基、—取代胺基，及通式(la)〜(3a): 一 (〇)l —D(la) —0(C = Ο)—D (2a) -(C = 0)〇-D(3a) 0為無取代或經取代之直鏈狀、分支鏈狀或環狀竣數 1〜8之絲、無取代或經取代之碳數4〜12之 =;代之碳數7〜2。之織，“示。或二i 支鏈之1V D之無取代或經取代之直鏈狀、分 20之菩Vi反數1〜8之烷基、D之無取代或經取代之碳數7〜 s 3 之較佳例及具體例，例如與就通式(1)之中X1〜X4及通式(a—2)之中a产與八产反取代基所示後❹，囉者。㈣私基》方純雜％基上之 D之方魏烴基或料族雜環基之具體例，例如:笨基、卜 13 200906909 二吡啶基、1^基4 1 基、2 —喹啉基、4-吡啶基、3 塔听基、基、2 —如基、定基、5—时基、3- 并咬喃基、4: _ ^并七^基2、3 —°夫喃基、2-吱喃基、2-笨 …塞吩基、：心4 ί夫錄、3 —齡基、2 2 —噻唑美、9 ? αο / —本开噻吩一2 —基、2 —噚唑基、吟唾—3:α、~^巧5基、2—苯并嗜唾基、2-苯并，嗤基、〇之^^ J：笨基苯基、3 —苯基苯基、4—苯基苯基等。環狀院Α。之取代基，例如®素原子、直鏈、分支鏈或 2或城絲，可為無取代亦可為經取代。烧基以碳支鏈或ϊίίί ’碳數1〜8者更佳。無取代或經取代之直鏈、分 ^衣狀丈元基之具體例，例如:後述D«之烧基。㈣ζ Γζ <單取代胺基及二取代胺基之具體例，例如:ν-甲基 ^ 乙基胺基、Ν—苯基胺基、Ν-(1-萘基)胺基、Ν-(2 =)胺基、Ν，Ν-二曱基胺基、Ν，Ν—二乙基胺基、Ν，Ν—二苯土月女土、Ν，Ν—一(1 一萘基)胺基、Ν，Ν—二(2一萘基)胺基、9Η_ 味唾-9-基、10Η-啡嗟呼―10 —基(1〇Η —沖⑽脇―—1〇 — yi)、10Η 一㈣啡一 10—基(簡—phen〇xazine—10—yl)、Ν—苯基〜Ν—(1 —萘基)胺基、Ν—苯基—Ν —(2—萘基)胺基、Ν一苯基— Ν —(1—蒽基)胺基、Ν —苯基一Ν — (9一蒽基)胺基、Ν—苯基_Ν 〜(1 —菲基)胺基、Ν—苯基一Ν —(2—菲基)胺基、ν —苯基一Ν — (3 —菲基)胺基、N—苯基一N —(4—菲基)胺基、N—苯基一N—(9 二菲基)胺基、N—苯基一N — (1 —芘基)胺基、N—苯基—N_(2 —(1) Eight, enter. (wherein Ζ1~Ζ4, shows, algebra; ρί, ρ2 represents an integer of 〇~5; ～ χ 丨之之之芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香芳香, 且:=香;ί::二12 200906909 The aromatic groups are bonded to each other to form a ring aromatic group; τ1 and τ2 are selected from a single bond, —(CH2)t— '—CH=CH— '—C ^C— ' —〇 — ^ —S— > ~CQ!Q2 — a CO—, a SO S〇2 SiE2—the basis of the group formed, which may be the same or different, and t represents an integer from 1 to 20 ; Q1 and Q2 represent an alkyl group or an aromatic group, and may be bonded to each other to form a ring; E represents a hydrogen atom, an alkyl group or an aromatic group; m, n 'an integer of 2 to 2.) 'The number of sulfo groups is not particularly limited' The average number of sulfo groups per repeating unit is 〇1 to 2〇, preferably 0.5 to 10, more preferably 1 to 8. In the general formula (1), at least one of Ρ1 to Ρ4 is an integer of 1 or more, and ζ47 indicates that the substituents may be the same or different from each other, each selected from a carboxyl group, a hydroxyl group, an amine group, and an early substituted amine group. , - substituted amine group, and formula (la) ~ (3a): one (〇) l - D (la) - 0 (C = Ο) - D (2a) - (C = 0) 〇 - D (3a 0 is an unsubstituted or substituted linear, branched or cyclic filament having a number of 1 to 8, a non-substituted or substituted carbon number of 4 to 12; and a carbon number of 7 to 2. Weaving, "expressed or substituted 1V D of 1V D unsubstituted or substituted linear, 20 radix Vi inverse 1~8 alkyl, D unsubstituted or substituted carbon number 7 Preferred examples and specific examples of the s 3 are, for example, those of the above-mentioned (1), X1 to X4, and the general formula (a-2), which are represented by a and octagonal anti-substituents. (4) A specific example of a D-hydrocarbyl group or a heterocyclic group of a D group on the basis of a pure base, for example, stupid base, b 13 200906909 dipyridyl, 1^yl 4 1 , 2 -quinolinyl , 4-pyridyl, 3-tower, base, 2- — group, group, 5-time group, 3- and thiol, 4: _ ^ and -7, 2, 3 —°, and 2, - 吱基, 2- stupid... thiophene, : heart 4 ί 录、, 3 - age base, 2 2 - thiazolyl, 9 ? αο / — thiophene-2-yl, 2-carbazolyl,吟 — - 3: α, ~ ^ 巧 5 base, 2- benzo-salophilic, 2-benzo, fluorenyl, oxime ^^ J: stupidyl phenyl, 3-phenylphenyl, 4-benzene A phenyl group, etc. a substituent such as a carboxylic acid, a linear chain, a branched chain or a 2 or a city wire, which may be unsubstituted or substituted. Carbon branch or ϊίίί 'The carbon number is 1 to 8. The specific example of the unsubstituted or substituted straight chain or the divided fabric is, for example, the D« burnt base described later. (4) ζ Γζ <single substitution Specific examples of the amine group and the disubstituted amine group are, for example, ν-methyl^ethylamino group, anthracene-phenylamino group, anthracene-(1-naphthyl)amino group, anthracene-(2=)amino group, Ν,Ν-didecylamino, hydrazine, hydrazine-diethylamino, hydrazine, hydrazine-diphenyl earth, female soil, hydrazine, hydrazine-mono(1-naphthyl)amine, hydrazine, hydrazine (2-naphthyl)amine group, 9Η_味唾-9-yl, 10Η-morphine ―10-based (1〇Η-冲(10) threat——-1〇—yi), 10Η一(四)啡一10-基(Jane-phen〇xazine-10-yl), fluorenyl-phenyl-indole-(1-naphthyl)amine, fluorenyl-phenyl-indole-(2-naphthyl)amine, fluorenyl-phenyl —(1—fluorenyl)amino, fluorenyl-phenyl-indole-(9-fluorenyl)amino, fluorenyl-phenyl-hydrazide~(1-phenanthryl)amino, fluorenyl-phenyl-hydrazine-( 2-phenanthryl)amino, ν-phenyl-indole-(3-phenanthryl)amino, N-phenyl-N-(4-phenanthryl)amino, N-phenyl-N-(9 Acetyl, N-phenyl-N — (1 — Yl) amine, N- phenyl -N_ (2 -

芘基)胺基、N—苯基一N —(4—芘基)胺基、n—苯基一N—(2— S 基)胺基、N —苯基一N — (5—苊基)胺基、n—苯基一N — (3—螢蒽基)胺基、N—苯基一N-(l —聯伸三苯基)胺基、N—苯基—n—(2Amidino, N-phenyl-N-(4-fluorenyl)amine, n-phenyl-N-(2-S-)amino, N-phenyl-N-(5-fluorenyl) Amino, n-phenyl-N-(3-fluorenyl)amine, N-phenyl-N-(l-linked triphenyl)amine, N-phenyl-n-(2)

〜聯伸三苯基)胺基、N—苯基一N — (1 —稠四苯基)胺基、N—苯基 —N—(2—稠四苯基)胺基、N—苯基一N—(9 —稠四苯基)胺基、N 〜苯基一N — (3—茈基)胺基、N—苯基一N —(4—喹啉基)胺基、N 14 200906909 —苯基一N — (2_嗤琳基)胺基、N—苯基一N —(2 —°比咬基)胺基、 N —苯基一N — (3 —吼11 定基)胺基、N —苯基一N — (4 —D比n定基)胺基、N—苯基一N —(2 —嘧啶基)胺基、N—苯基一N —(3—噻吩基) 胺基、N—苯基一N —(2—苯基苯基)胺基、N—苯基一N — (3—笨基苯基)胺基、N—苯基一N — (4—苯基苯基)胺基、n，N—雙[4 一 (二苯基胺基)苯基]胺基、N，N—雙[3 — (二苯基胺基)苯基]胺基、N,N 一雙[4一 {Ν'—苯基一Ν’一(2—萘基)胺基}苯基]胺基、n，N—雙[3 —{Ν'—苯基— Ν' —(2 —萘基)胺基}苯基]胺基、ν，Ν—雙[4— {Ν' — 苯基一Ν' —(1 —萘基)胺基}苯基]胺基、Ν，Ν—雙[3 — {Ν'—苯基一 —(1 —萘基)胺基}苯基]胺基、ν,Ν —雙[4-(9Η—卡唑—9-基)笨 -基]胺基、Ν，Ν —雙[3 —(9Η-中坐—9-基)苯基]胺基、ν,Ν—雙(4 — 績基苯基)胺基、Ν,Ν_雙[1—(8 —續基萘基)胺基、ν，ν—二[2 —(8 —石黃基萘基)]胺基、Ν —(4 —績基苯基)—ν —[1—(8—續基萘基)] 胺基、Ν—(4 —磺基苯基)一Ν—[2 — (8 —磺基萘基胺基、3,6一二，基_9Η-十坐—9 —基、Ν，Ν—雙[4—{雙(4，—石黃基苯基)胺基)笨，]胺基、Ν，Ν—雙[4 —(3,6-二續基—阳―咔唑—&基)苯基]胺 :、Ν，Ν-雙(4-曱基苯基)胺基、ν,Ν-雙(4—乙基苯基)胺基、 ΝΝ:^:ΐ丙ίίί)ΐ基、Ν，Ν—雙(4 —異丙基苯基)胺基、雙(4-第二基苯基)胺基、Ν，Ν一雙 νΓϊΓ^ Ν，Ν—雙(4一新戊基苯基)胺基、ΝΝ—雙~-stranded triphenyl)amine, N-phenyl-N-(1--tetraphenyl)amine, N-phenyl-N-(2-tallowtetraphenyl)amine, N-phenyl- N-(9-fused tetraphenyl)amino, N~phenyl-N-(3-indenyl)amino, N-phenyl-N-(4-quinolinyl)amino, N 14 200906909 — Phenyl-N-(2_嗤-linyl)amine, N-phenyl-N-(2-reptyl)amino, N-phenyl-N-(3-indolyl)amine, N-phenyl-N-(4-D-n-n-)amino, N-phenyl-N-(2-pyrimidinyl)amine, N-phenyl-N-(3-thienyl)amine, N-phenyl-N-(2-phenylphenyl)amino, N-phenyl-N-(3-phenylphenyl)amino, N-phenyl-N-(4-phenylphenyl) Amino, n,N-bis[4-(diphenylamino)phenyl]amine, N,N-bis[3-(diphenylamino)phenyl]amine, N,N Bis[4-{Ν'-phenyl-anthracene-(2-naphthyl)amino}phenyl]amine, n,N-bis[3 —{Ν'-phenyl- Ν' —(2 — Naphthyl)amino}phenyl]amine, ν,Ν-bis[4-{Ν'-phenyl-anthracene-(1-naphthyl)amino}phenyl]amine ,Ν,Ν—bis[3 — {Ν'-phenyl-(1-naphthyl)amino}phenyl]amine, ν,Ν-bis[4-(9Η-carbazole-9-yl) Amino, anthracene, fluorene-bis[3—(9Η-中坐-9-yl)phenyl]amine, ν, Ν-bis(4-phenylphenyl)amine, hydrazine, hydrazine _ bis [1- (8 - contigyl naphthyl) amine, ν, ν - bis [2- (8 - fluorenyl) naphthyl), Ν - (4 - phenyl) - ν - [1-(8-thenylnaphthyl)]amino, Ν-(4-sulfophenyl)-anthracene-[2 - (8-sulfonaphthylamino group, 3,6-two, yl--9Η) - Ten sitting - 9 - base, Ν, Ν - bis [4-{bis(4,- schistyl)amino) stupid,] amine, hydrazine, hydrazine - bis [4 - (3,6-续, 阳, 双-bis(4-ethylphenyl)amine, Ν, bis-(4-mercaptophenyl)amine, ν, Ν-bis(4-ethylphenyl)amine , ΝΝ:^:ΐ丙ίίίίί)ΐ,Ν,Ν—bis(4-isopropylphenyl)amine, bis(4-secondylphenyl)amine, hydrazine, hydrazine, 双νΓϊΓ^ Ν , Ν-bis(4-monopentylphenyl)amine, ΝΝ-double

胺基以[r(4一甲基-2-戊基么U 24各f同取，，且"各上或，P〜P4可以為零。 1王通式(1)中，χ1〜X4獨立地表示1價关巷故I A 埃煙基或1價料麵縣。鱗射香 15 200906909 X1與X2、X3與X4可以彼此鍵結之芳香族烴基之情形，構成該基之莩基為無取代或經取刊〜20更佳。另-方面，此等基為無取H數以卜3G較佳’碳數e 之情形，構成該基之環碳數以3〜3 ^經取代之芳香族雜環基〜X4可為相同基或不同基^ 钕佳，碳數3〜20更佳。χ] 基、Μ 基以雜環基之具體例，例如:苯 2 —菲基、3 —菲基、4〜菲基、9〜菲|葱基、9—蒽基、丨一菲基、伸苯基、2 —聯伸苯基、卜芘其 =2—氟一9—菲基、1—: 危基、3-料基、丨—聯伸站基、4—祐基、2—第基 .苯基、2-稠四苯基、9 —稠聯伸三苯基、卜稠t 琳基、4〜吼η定基、3 —^比。定基、2^π〜並基' 4—啥琳基、2 —D 基、5-，定基、3 —D荅听基% =基、2 —♦定基、4-♦ 3 一夫喃基、2-料基、2—基、 2 —二苯料喃基、31吩λ、2tT夫储、4 —二苯并咬喃基二苯并噻吩一2 —基、2 —崎4其、1塞吩基、二苯并噻吩一4-基、 —苯并麵基、2—苯㈣。坐^、nm2—苯并+坐基、 —苯基苯基、4-苯基苯基、‘聯：3其基、2-苯基苯基、：對聯三苯一2 —基、間聯三苯—夂本=基、+對聯三苯+基 X1與X2、X3與X4可她間聯二本—3 —基等。 -此鍵結形成環之情形之具體例，I j環。X1與X2、X3與X4招巧穴犯-二苯基、 X〜X之1價芳香族基，尚包含通式卜2)所示基。The amine group is taken as [r(4-methyl-2-pentyl) U 24 each f, and " each or, P~P4 can be zero. 1 king formula (1), χ1~X4 Independently indicates the IA smoky base or the valence noodle county of the 1st price. The case of the aromatic hydrocarbon group in which X2 and X2, X3 and X4 can be bonded to each other, the thiol group constituting the base is none. Substituting or retrieving ~20 is better. On the other hand, these bases are in the case of no H number, and 3G is preferably 'carbon number e, and the ring carbon number of the base is 3~3 ^ substituted. The group heterocyclic group ~X4 may be the same group or a different group, preferably having a carbon number of 3 to 20. The specific examples of the heterocyclic group are, for example, benzene-2-phenanthryl, 3-phenanthrene. Base, 4~phenanthrenyl, 9~phenanthrene|onion base, 9-fluorenyl group, fluorene phenanthrene group, phenylene group, 2 -strand phenyl group, diazepam = 2 - fluoro- 9-phenanthryl group, 1 - : dangerous base, 3-feeding base, hydrazine-coupling station base, 4-youji, 2-diyl. phenyl, 2-thick tetraphenyl, 9-fused triphenyl, di-t-lin, 4 ~吼η定基,3—^ ratio.定基,2^π〜基基' 4—啥琳基, 2—D base, 5-, fixed base, 3—D荅 listen base % = Base, 2- ♦ group, 4-♦ 3 hexanyl, 2-butyl, 2-yl, 2-diphenyl moryl, 31 λ, 2tT, 4-dibenzo- benzoyl And thiophene-2-yl, 2-sodium 4, 1 phenantyl, dibenzothiophene-4-yl, benzoheptyl, 2-phenyl (tetra). sitting ^, nm2 - benzoxanthene, Phenylphenyl, 4-phenylphenyl, 'linked: 3, 2-phenylphenyl, conjugated triphenyl-2-yl, m-triphenyl- fluorene = yl, + conjugated triphenyl + Base X1 and X2, X3 and X4 can be linked to each other - 3 - base, etc. - A specific example of the case where the bond forms a ring, I j ring. X1 and X2, X3 and X4 are tricky - diphenyl The group and the monovalent aromatic group of X to X further include a group represented by the formula (2).

(a-2) (式中，Aral、Ara2 本-w® 上 μ •ί表示1〜2之整數。）々不貝之方香族基，可以彼此鍵結成環 16 200906909(a-2) (wherein, Aral, Ara2, and -w® are on μ • ί means an integer from 1 to 2.) 々之 fangs, which can be bonded to each other in a ring 16 200906909

Aral、A/2獨立地表* 代亦可經取代。員方香知基’ 1價芳香族基可以無取Aral, A/2 independent table * generation can also be replaced. Member Fang Xiangzhiji's 1-valent aromatic group can be taken

Ar、Ar之1價芳香族香族雜環基。此等基可為盔、土，包3 1價芳香族烴基或1價芳環。此等基為無取代或^忑，代，可為經取代，可以彼此鍵結成環之碳數以ό〜30較佳，护^、之芳香族烴基之情形，構成該基之無取代或經取代之芳香族^ 6〜20更佳。另-方面，此等基為〜30較佳，碳數3〜2〇更伟衣土 ^情形，構成該基之環之碳數以3 W、Α产之芳香族夫可為相同基或不同基。 Γ 〜X4之具體例中所示者。^土或方日私雜環基之具體例，例如χι .蔡基、9-菲基較佳。匕專具體例之中，苯基、1 —萘基、2 —A monovalent aromatic aromatic heterocyclic group of Ar and Ar. These groups may be helmets, soils, or a trivalent aromatic hydrocarbon group or a monovalent aromatic ring. These groups are unsubstituted or substituted, and may be substituted, and may be bonded to each other to form a ring having a carbon number of ό30, preferably an aromatic hydrocarbon group, which constitutes an unsubstituted or substituted group of the group. Replace the aromatic ^ 6~20 better. In another aspect, the base is preferably -30, and the carbon number is 3 to 2 Å, and the carbon number of the ring constituting the base is 3 W, and the aromatic sulphate may be the same base or different. base. Γ ~X4 is shown in the specific example. Specific examples of the soil or the Japanese private heterocyclic group, for example, χι. Caiji, 9-phenanthryl is preferred. Among the specific examples, phenyl, 1-naphthyl, 2 —

Aral、Ara2可以彼此鍵結情形之具體例，例如9H〜 j Ar、Ar彼此鍵結形成環之 5H—二苯并[b,f]氮呼—^等Y —基、10H—啡噻畊一1〇 —基、Specific examples in which Aral and Ara2 can be bonded to each other, for example, 9H to j Ar, Ar are bonded to each other to form a ring of 5H-dibenzo[b,f]azepine-^, and the like, and 10H-morphine 1〇—基,

Ara2縣上之取代基，及Μ、基、經基、胺基 '單取代胺其、衣基上之取代基，例如:擇自於羧 -D, (1，a)代胺基、二取代胺基，及通式(l，a)〜⑽： ^^0 = 0)-01 (2'a) 〜(C = 〇)〇-Di(3ia) 數1 代或經取代之直鏈狀、分支鏈狀切狀破 —叙n 基、無取代或經取代之钱4〜… ‘:、、取代或經取代之碳數7〜2〇 ^ 4之)方香族基、二通式㈣所示基較佳。，=基’ L，表〜。或”所示基， 1，芳香族烴基或料族轉基上之f j L'G/佳夕〜香族烴基或苦未旎Μ卢盆L 之取代基，及Ar 、Ar32之芳又，取代數不^較^土〇〜t取代基之取代位置不特別限制。例如之f ^分支鏈或剩道基之具體例，基正丙基異丙基、正丁基、異丁基、第二丁基、 17 200906909 第二丁基、正戊基、異戊基、新戊基、第三戊基、正己基、」—甲基戊基、4-甲基-2-戊基、2—乙基丁基、2-乙基己基、正庚基、1-甲基己基、正辛基、卜曱基庚基、2_丙基戊基、2,2 —二曱基己基、2,6 —二曱基—4—己基、3,5,5 —三甲基戊基、環己基、環己基甲基、環戊基、2—乙基丁基、3,3~二曱基丁基、二甲基己基、卜降福基、2—降箱烧曱基、環丁基、1 ΓΛ基H 4— ?基環己基、3 — f基環己基、2— f基環己基、二J f'己基、2,5 —二曱基環己基、2,6 -二甲基環己基、3,4 —甲基％己基、3,5 —二甲基環己基、環庚基、環辛基、 -乙乙氧基甲基、正丁氧基甲基、正己氧基甲基、（2 其t、正辛氧基甲基、正癸氧基甲基、2—甲氧基乙 2丁，—其Λ基5基、2二正丙氧基乙基、2-異丙氧基乙基、美丁土故正戊氧基乙基、2 —正己氧基乙基、2 —(2，一乙 :—正庚氧基乙基、2 —正辛氧基乙基、2-( 2, 基丙基、3-乙氧基丙基Γ己祿乙基2—曱減丙基、3一甲氧 -(正3戊二3 —異丙氧基丙基、3〜(正丁氧基)丙基、3 丙基、4—甲氧(乙基己虱基)丙基、3 —環己氧基異丙‘丁A ：〜乙氧基丁基、4 —正丙氧基丁基、4- 基丁基、5乌氧氧f 丁基、4 —正已氧基丁基、4 —正辛氧 -乙氧基己基=氧=氧t气基、r正乙氧基戊基、6 基己基、4—甲氧美璟p其土7 土 " 丁氧基己基、6~正己氧甲氧基辛基、二氫糠乙氧基庚基、7—異丙氧基庚基' 基f基、2—(2，—乙氧基乙氧基)乙基、2 丙氧基乙基、2,4烯mu减乙氧基)丙基、2—烯 18 200906909 丙氧基丁基、节氧基甲基、2—节氧基乙基、2 —苯乙基乳乙基:2-(4.-甲基节氧基)乙基、2_(2，_曱基节氧基)乙基、 2-(4’-氟节氧基)乙基、2 —(4’—氯节氧基基、3 —节氧基丙基、 3 — (4'—曱氧基苄氧基)丙基、4—苄氧基丁基、2一（苄氧基甲乙基、2 — (4’一甲基苄氧基甲氧基)乙基、基甲基、4—曱基苯氧基甲基、3一曱基苯氧基曱基、2 — 苯氧基甲基、4-甲氧基苯氧基甲基、4—氣苯氧基甲基、4 — ，，氧基曱基、2—氯苯氧基甲基、2—苯氧基乙基、2 —(4，—甲基苯氧基)乙基、2 —(4’—乙基苯氧基)乙基、2 —(4,—曱氧基苯氧基) 、2-(4’一氣苯氧基)乙基、2_(4’_溴苯氧基)乙基、2一(1，— ，氧基)乙基、2 — (2’一萘氧基)乙基、3一苯氧基丙基、3_(2,—萘丙基、4—苯氧基丁基、4 —(2ι—乙基苯氧基)丁基、5 —(4,二第二丁基苯氧基)戊基、6 —(2’一氣苯氧基)己基、8 —苯氧基辛基、 2 —(2' —苯氧基乙氧基)乙基、3 —(2,一苯氧基乙氧基)丙基、4 — (2, 一苯氧基乙氧基)丁基、正丁基硫甲基、正己基硫曱基、2—曱基硫乙基、2〜乙基硫乙基、2 —正丁基硫乙基、2 —正己基硫乙基、2 —正辛基硫乙基、 2—正癸基硫乙基、3—甲基硫丙基、3—乙基硫丙基、3〜正丁基硫丙基、4一乙基硫丁基、4 —正丙基硫丁基、4 —正丁基硫丁基、 5—乙基琉戊基、6—甲基疏己基、6—乙基硫己基、6 —正丁基碗 -己基、8—曱基硫辛基、2 —(2’一曱氧基乙基硫)乙基、4__( 3，一乙 —氧基丙基硫)丁基、2 — (2' —乙基硫乙基硫）乙基、2 —埽丙基硫乙基、2—苄基硫乙基、3 —(4'—曱基苄基琉)丙基、4—苄基硫丁基、 2 — (2'—苄氧基乙基硫）乙基、3 —(3'—苄基硫丙基硫)丙基、2一苯基硫乙基、2 —(4f—甲氧基苯基硫)乙基、2 — (2'—苯氧基乙基硫）乙基、3 —(21—苯基硫乙基硫)丙基、 2 —羥基乙基、2 —羧基丙基、3 —羥基丙基、3 —經基丁基、4 —羥基丁基、6 —羥基己基、5—羥基庚基、8—羥基辛基、2一羥基環己基等。 ' 19 200906909 等基可為香:念族雜環基。此族烴基之_，構成該基之環碳數或=代之芳香碳數以4〜取代之方魏雜環基之情形，構成該基之環之 & ^ O2~itk5%T^ 5 ^'Ηα：^ —吡啶基、2-吡咬基土、2 —哺^基;2—喹，、4—比啶基、3 塔畊基、4…答听基、2—比=基二…密咬基、5 —咖定基、3- .并吱喃;&、4~二苯并吱喃λ、土 _ af°南基、2一吱喃基、2-苯 -噻吩基、4 =〜二苯并吱喃基、3—塞吩基、2 2 一塞唾基、、二笨并齡—2 —基、2 —，坐基、。卡唾-3-基、\2—苯并射基、2—苯并咪唾基、 D，之芳纽/ 基苯基苯基、4—苯基苯基等。環狀烧基取代基，例如鹵素原子、直鏈、分支鏈或原子’例如:氟原子、氣原子、溴原子、碘原子。碳數3 =取代亦可為經取代。院基以八古絲灿七戸心ί 數1〜8者更佳。無取代或經取代之直鏈狀、二、分支iDf之具體例’例如:D,之無取代或經取代之直鏈狀77支鏈狀或J展狀烷基所示者。無甲取^或^取代之碳數7〜2〇之芳院基之具體例，例如: 二“笑Λ基卞基、α—乙基节基、苯乙基、α_甲基苯乙基、p ^ ^ 土、α，α—二曱基苄基、α，α—二甲基苯乙基、4—甲基 Ϊ 2乙二，基、3—曱鮮基、2—甲鮮基、4—乙基节 ί基、4—異丙基节基、4—第三丁基节基、2-第三三雜絲、4 —環己鮮基、4 —正辛基节基、 I 4二基、4~~烯丙基节基、4一节基节基、4—苯乙基节：本基、4 —(4’_甲基苯基抒基、4—曱氧基节基、2-T氧暴卞基、2〜乙氧基苄基、4—正丁氧基苄基、4 —正庚氧基苄 20 200906909 —正癸氧基苄基、4一正十四烷氧基苄基、4—正十五烷氧 T基、 —二甲氧基节基、4—甲氧基曱基节基、4—異丁氧基甲基卞基^ 4 — ；)^丙氧基苄基、4—乙烯基氧曱基苄基、4—苄氧基苄基、 4—苯乙基氧苄基、4一苯氧基苄基、3一苯氧基苄基、4 —羥基苄，二3一羥基苄基、2 —羥基苄基、4 —羥基一3—曱氧基苄基、土4一氟、2—氟苄基、4—氯苄基、3 —氯苄基、2—氯苄基、3,4 — 二氯ΐ基L2 —糠基、二苯基甲基、1_萘基甲基、2一萘基甲基等。、A it早取代胺基、或一取代胺基之取代基，例如:無取代或經 -取代之直鏈狀、分支鏈狀或環狀烷基。該烷基，以碳數丨〜16者較佳二碳數1〜8者更佳。烷基之具體例’例如D,之烷基所示者。單取代fee基及一取代胺基之具體例，例如N—曱基胺基、N — 乙基胺基、N—苯基胺基、N — (1 一萘基)胺基、N —(2一萘基)胺基、 N，N—二曱基胺基、N,N一二乙基胺基、N，N—二苯基胺基、N，N -二(1 —萘基)胺基、N，N—二(2-萘基)胺基、9H-咔唑—9-基、 10H-啡《塞啡—1〇 —基、i〇H—„非今井—1〇一基、N—苯基—N—〇一奈基)胺基、N—苯基—N — (2—萘基)胺基、N—苯基—(1 — 恩基)胺基、N—苯基—n — (9—蒽基)胺基、]Sf—苯基一Ν —(1 —菲基)胺基、N—苯基(2—菲基)胺基、N—苯基一N—(3—菲基) 胺基、N—苯基一:K一(4—菲基)胺基、N—苯基一N —(9—菲基)胺 -基、苯基一N —(1—芘基)胺基、N 一苯基—N — (2—芘基)胺基、a substituent on Ara2, and a substituent of a fluorenyl group, a hydrazino group, a hydrazino group, an amino group, a monosubstituted amine, and a thiol group, for example, a carboxy-D, (1, a) amino group, a disubstituted group Amino group, and formula (l, a) to (10): ^^0 = 0)-01 (2'a) ~ (C = 〇) 〇-Di (3ia) number 1 or substituted linear, Branched chain-like cut-formed n-base, unsubstituted or substituted money 4~... ':, substituted or substituted carbon number 7~2〇^ 4) Fangxiang group, two formula (4) The base is preferred. , = base 'L, table ~. Or "the indicated group, 1, a substituent of the fj L'G / Jia Xi ~ aroma hydrocarbon group or the Kushui Lu basin L on the aromatic hydrocarbon group or the group of the base group, and the aromatic and substituted Ar and Ar32 The substitution position of the number of the substituents is not particularly limited. For example, a specific example of the f ^ branching chain or the remaining group, n-propyl isopropyl, n-butyl, isobutyl, and second Butyl, 17 200906909 second butyl, n-pentyl, isopentyl, neopentyl, third amyl, n-hexyl, "-methylpentyl, 4-methyl-2-pentyl, 2-B Butyl, 2-ethylhexyl, n-heptyl, 1-methylhexyl, n-octyl, decylheptyl, 2-propylpentyl, 2,2-didecylhexyl, 2,6-di 4- 4-hexyl, 3,5,5-trimethylpentyl, cyclohexyl, cyclohexylmethyl, cyclopentyl, 2-ethylbutyl, 3,3-didecylbutyl, dimethyl己基, 卜降福基, 2—lower sulphonate, cyclobutyl, 1 fluorenyl H 4 —cyclohexyl, 3 — f cyclohexyl, 2-f cyclohexyl, di J f hexyl, 2,5-dimercaptocyclohexyl, 2,6-dimethylcyclohexyl, 3,4-methyl-hexyl, 3,5-di Cyclohexyl, cycloheptyl, cyclooctyl, -ethylethoxymethyl, n-butoxymethyl, n-hexyloxymethyl, (2, t, n-octyloxymethyl, n-decyloxy Base, 2-methoxyethyl 2, - fluorenyl 5, 2 - di-n-propoxyethyl, 2-isopropoxyethyl, butyl pentoxide, 2-pentyloxyethyl Oxyethyl, 2-(2,1-ethyl:-n-heptyloxyethyl, 2-n-octyloxyethyl, 2-( 2,propyl,3-ethoxypropyl Γ 禄乙Base 2 - hydrazine minus propyl, 3 - methoxy-(n- 3 pentane 3 -isopropoxypropyl, 3 〜 (n-butoxy) propyl, 3 propyl, 4-methoxy (ethyl hexyl) Mercapto)propyl, 3-cyclohexyloxyisopropyl 'but A: ~ethoxybutyl, 4-n-propyloxybutyl, 4-butylbutyl, 5-oxooxyl-butyl, 4- Orthobutyloxy, 4-n-octyloxy-ethoxyhexyl = oxygen = oxygen t gas group, r n-ethoxypentyl group, 6 hexyl group, 4-methoxyxan p soil 7 soil " Butoxy hexyl, 6-n-hexyloxymethoxyoctyl, indoline ethoxyheptyl, 7-isopropoxyheptyl'yl-f-yl, 2-(2,-ethoxyethoxy) Ethyl, 2 propoxy B 2,4 olefinic mu minus ethoxy)propyl, 2-ene 18 200906909 propoxy butyl, ethoxymethyl, 2-hydroxyethyl, 2-phenylethyl lactyl: 2- (4.-Methyl hydroxy)ethyl, 2-(2,-fluorenyloxy)ethyl, 2-(4'-fluoro-ethoxy)ethyl, 2-(4'-chlorooxyl Base, 3-hydroxypropyl, 3-(4'-methoxybenzyloxy)propyl, 4-benzyloxybutyl, 2-monobenzyloxyethyl, 2- (4'- Methylbenzyloxymethoxy)ethyl, methyl, 4-nonylphenoxymethyl, 3-monophenylphenoxymethyl, 2-phenoxymethyl, 4-methoxybenzene Oxymethyl, 4-phenoxymethyl, 4-, oxyindenyl, 2-chlorophenoxymethyl, 2-phenoxyethyl, 2-(4-methylphenoxy) Ethyl, 2-(4'-ethylphenoxy)ethyl, 2-(4,-methoxyphenoxy), 2-(4'-phenoxy)ethyl, 2-(4) '_Bromophenoxy)ethyl, 2-(1,-,oxy)ethyl, 2-(2'-naphthyloxy)ethyl, 3-phenoxypropyl, 3-(2,-naphthalene Propyl, 4-phenoxybutyl, 4-(2i-ethylphenoxy)butyl, 5-(4, two Second butyl phenoxy)pentyl, 6 —( 2′ monophenoxy)hexyl, 8-phenoxyoctyl, 2-(2′-phenoxyethoxy)ethyl, 3-—( 2, monophenoxyethoxy)propyl, 4-(2,monophenoxyethoxy)butyl, n-butylthiomethyl, n-hexylthiol, 2-mercaptothioethyl, 2~ethylthioethyl, 2-n-butylthioethyl, 2-n-hexylthioethyl, 2-n-octylthioethyl, 2-n-decylthioethyl, 3-methylthiopropyl , 3-ethylthiopropyl, 3-n-butylthiopropyl, 4-ethylthiobutyl, 4-n-propylthiobutyl, 4-n-butylthiobutyl, 5-ethylindole Base, 6-methyl chlorohexyl, 6-ethylthiohexyl, 6-n-butyl bowl-hexyl, 8-mercaptothiooctyl, 2-(2'-methoxyethylthio)ethyl, 4__ (3,1-ethyl-propyl propyl)butyl, 2-(2'-ethylthioethylthio)ethyl, 2-mercaptopropylthioethyl, 2-benzylthioethyl, 3- (4'-Mercaptobenzylhydrazine) propyl, 4-benzylthiobutyl, 2-(2'-benzyloxyethylsulfanyl)ethyl, 3-(3'-benzylthiopropylsulfide) Propyl, 2-phenylthio , 2-(4f-methoxyphenylthio)ethyl, 2-(2'-phenoxyethylsulfanyl)ethyl, 3-(21-phenylthioethylsulfanyl)propyl, 2-hydroxyl Ethyl, 2-carboxypropyl, 3-hydroxypropyl, 3-bromobutyl, 4-hydroxybutyl, 6-hydroxyhexyl, 5-hydroxyheptyl, 8-hydroxyoctyl, 2-hydroxycyclohexyl Wait. ' 19 200906909 The base can be a fragrant: nucleus heterocyclic group. The olefin of this group constitutes the ring carbon number of the group or the case where the number of aromatic carbons is replaced by a 4~-substituted tetra-heterocyclic group, which constitutes the ring of the group & ^ O2~itk5%T^ 5 ^ 'Ηα:^—pyridyl, 2-pyrylene, 2—feeding base; 2-quine, 4-pyridyl, 3 towering, 4... answering base, 2-ratio=base two...密基基,5-咖定基,3-. and 吱 ;; &, 4~ dibenzopyrene λ, soil _ af ° Nanji, 2-monoanyl, 2-phenyl-thienyl, 4 = ~ Dibenzopyranyl, 3-destenyl, 2 2 -Sedyl, 2nd and 2nd, 2 -, S,. Carboxy-3-yl, \2-benzoinyl, 2-benzopyranyl, D, aryl/phenylphenyl, 4-phenylphenyl and the like. A cyclic alkyl group such as a halogen atom, a linear chain, a branched chain or an atom 'e.g., a fluorine atom, a gas atom, a bromine atom, or an iodine atom. Carbon number 3 = substitution may also be substituted. The base of the school is better with eight ancient silks and seven hearts. Specific examples of the unsubstituted or substituted linear, di- or branched iDf are, for example, D, unsubstituted or substituted linear 77-chain or J-extended alkyl. Specific examples of the aromatic base of the carbon number 7~2〇 without the substitution of ^ or ^, for example: 2 "Laughing fluorenyl, α-ethyl, phenethyl, α-methylphenethyl , p ^ ^ soil, α,α-dimercaptobenzyl, α,α-dimethylphenethyl, 4-methylindole 2 ethyl, ketone, 3-indanyl, 2-methyl fresh base, 4-ethyl benzyl, 4-isopropyl benzyl, 4-tert-butyl, 2-third tris, 4-cyclohexanyl, 4-n-octyl, I 4 Dibasic, 4~~allyl, 4-blocky, 4-phenethyl group: base, 4-(4'-methylphenylindenyl, 4-anoxyl group, 2-Toxythiol, 2~ethoxybenzyl, 4-n-butoxybenzyl, 4-n-heptyloxybenzyl 20 200906909 - n-decyloxybenzyl, 4-n-tetradecyloxy Benzyl, 4-n-pentadecanyloxy T-based, -dimethoxyoxyl, 4-methoxyindenyl, 4-isobutoxymethylindolyl 4 - ; Benzyl, 4-vinyloxenylbenzyl, 4-benzyloxybenzyl, 4-phenylethyloxybenzyl, 4-phenoxybenzyl, 3-phenoxybenzyl, 4-hydroxybenzyl Di- 3-hydroxyl Base, 2-hydroxybenzyl, 4-hydroxy-3-oxooxybenzyl, 4-fluoro, 2-fluorobenzyl, 4-chlorobenzyl, 3-chlorobenzyl, 2-chlorobenzyl, 3 4 — Dichloroindenyl L 2 —fluorenyl, diphenylmethyl, 1-naphthylmethyl, 2-naphthylmethyl, etc. A, an early substituted amino group, or a substituted amino group substituent, For example, an unsubstituted or substituted-substituted linear, branched or cyclic alkyl group. The alkyl group is preferably a carbon number of 1616 or more preferably a divalent number of 1 to 8. A specific example of the alkyl group. 'A. For example, D, the alkyl group is shown. Specific examples of the mono-substituted fe-based group and the mono-substituted amino group, such as N-decylamino group, N-ethylamino group, N-phenylamino group, N-(1) Anaphthyl)amine, N-(2-naphthyl)amine, N,N-didecylamino, N,N-diethylamino, N,N-diphenylamino, N, N-bis(1-naphthyl)amine, N,N-bis(2-naphthyl)amine, 9H-carbazole-9-yl, 10H-morphine, "Serbian-1", i〇H —„非今井—1〇一基,N—Phenyl—N—〇-N-yl) Amine, N—Phenyl-N —(2-naphthyl)amine, N—Phenyl—(1—恩Amino group, N- Base—n —(9-fluorenyl)amine,]Sf—phenyl-indole—(1-phenanthrenyl)amine, N-phenyl(2-phenanthryl)amine, N-phenyl-N— (3-phenanthryl) Amino, N-phenyl-: K-(4-phenanthryl)amino, N-phenyl-N-(9-phenanthryl)amine-yl, phenyl-N-(1 —mercapto)amino, N-phenyl-N —(2-indenyl)amine,

_ 苯基一N一(4〜芘基)胺基、N—苯基一N —(2—苐基)胺基、N 一苯基—N—(5 —苊基)胺基、N—苯基一N —(3 —熒蒽基)胺基、N —苯基一N — (l—聯伸三苯基)胺基、N—苯基—N —(2一聯伸三苯基)胺基、N—苯基一N —〇一稠四苯基)胺基、N—苯基—N—(2一稠四苯基)胺基、苯基一N —(9 —稠四苯基)胺基、N—苯基一N —(3—茈基)胺基、N—苯基一N — (4—喹琳基)胺基、N—苯基一N (2—啥琳基)胺基、n—苯基_n—(2 —η比n定基)胺基、n一苯基一 N—(3 — η比咬基)胺基、苯基一N—(4一吼。定基)胺基、N—苯基 21 200906909 —N — (2 —嘧啶基)胺基、N—苯基一N—(3—噻吩基)胺基、N—苯基_N—(2—苯基苯基)胺基、N—苯基一N —(3—苯基苯基)胺基、 N—苯基一 N—(4—苯基苯基)胺基、N，N—雙[4 —(二苯基胺基)苯基] 胺基、N，N—雙[3-(二苯基胺基)苯基]胺基、n，N—雙[4-{Ν’-苯基一Ν'— (2—萘基)胺基}苯基]胺基、ν，Ν—雙[3 — {Ν'—笨基一Ν' —(2—萘基)胺基}苯基]胺基、Ν，Ν—雙[4_ {Ν' —苯基一 Ν1 — (1 —萘基)胺基}苯基]胺基、Ν，Ν—雙[3 — {Ν'—苯基—Ν’ — (1 —萘基)胺基} 苯基]胺基、Ν，Ν—雙[4一(9Η —咔唑一9-基)苯基]胺基、Ν，Ν_雙[3 -(9Η -咔唑—9 -基)苯基]胺基、Ν，Ν -雙(4 -續基苯基)胺基、Ν,Ν —雙[1一(8-磺基萘基)胺基、ν，Ν—二[2 — (8 —磺基萘基)]胺基、& 一(4 —磺基苯基)—N-[l—(8-磺基萘基)]胺基、Ν —(4-磺基苯基) —Ν— [2 —(8 —磺基萘基)]胺基、3,6 —二磺基一9Η—咔唑一9 — 基、Ν，Ν—雙[4—{雙(4，—磺基苯基)胺基}苯基]胺基、Ν，Ν —雙[4 一 (3,6 —二磺基—9Η—咔唑一 9-基)苯基]胺基、ν，Ν —雙(4—曱基苯基)胺基、Ν，Ν—雙(4一乙基苯基)胺基、Ν，Ν—雙(4 —正丙基苯基）胺基、Ν，Ν-雙(4—異丙基苯基)胺基、Ν，Ν—雙(4 —正丁基苯基）胺基、Ν，Ν—雙(4一異丁基苯基)胺基、Ν，Ν—雙(4一第二丁基苯基） =基、Ν，Ν —雙(4—第三丁基苯基)胺基、Ν,Ν—雙(4一正戊基苯基）、Ν，Ν—雙(4一異戊基苯基)胺基、Ν，Ν—雙(4 —新戊基苯基） ^基、Ν，Ν~~雙(4 一第三戊基苯基)胺基、Ν，Ν 一雙(4_正己基苯基）月女基、Ν，Ν—雙[4一(1 —甲基戊基)笨基]胺基、Ν，Ν—雙[4~(4—曱基一 2〜戊基)苯基]胺基等。通式⑴中，Υ以碳數4〜9〇之2價芳香族基較佳。以-Υ-所示基’包含通式(lb): -A-(B-A)u- (lb) (式中，A表示2價芳香族基，_B_表示單鍵、伸烷基、_〇_、 -S-、-CO-、_s〇_、_s〇r、_SiH2_及_siMe2，u 表示〇〜2 之整數。）所不基。又，A可彼此鍵結成環。 u以〇〜1之整數較佳。 22 200906909 A以兔數4〜60之2價芳夭f ±J_ 或2價芳香族雜環基。 "土乂佳’包含2價芳香族烴基 Δ 七 1 A之2價芳香族烴基或2 經取代。該基為無取代或經取代之環基，可為無取代亦习 ^ 6〜3〇較佳。另一方面，該二族烴基之情形’該基碳彰土之情形，_該基碳數以4〜3〇“：、'代或經取代之芳香族雜環例如舆通式(1)$》或芳香族雜it基上代基‘方香族煙基'或芳香族雜取 -I 90 ，第—基、2,7·咔唑二其^ 基、9,瓜蒽二基、并呋喃二I、π二二，花一基、2,8~-二羞龙岵吐_ J8〜比二基、_Phenyl-N-(4-fluorenyl)amine, N-phenyl-N-(2-indenyl)amine, N-phenyl-N-(5-fluorenyl)amine, N-Benzene a group of N-(3-fluorofluorenyl)amine, N-phenyl-N-(l-linked triphenyl)amine, N-phenyl-N-(2-mono-triphenyl)amine, N-phenyl-N-fluorene-thick tetraphenyl)amino group, N-phenyl-N-(2-monotetraphenyl)amino group, phenyl-N-(9-thick tetraphenyl)amino group , N-phenyl-N-(3-indenyl)amino, N-phenyl-N-(4-quinolinyl)amino, N-phenyl-N(2-indenyl)amine, N-phenyl_n-(2-n-n-n-decyl)amino group, n-phenyl-N-(3-n-octyl)amino group, phenyl-N-(4-indenyl)amino group , N-phenyl 21 200906909 —N — (2-pyrimidinyl)amino, N—phenyl-N—(3-thienyl)amino, N—phenyl_N—(2-phenylphenyl) Amine, N-phenyl-N-(3-phenylphenyl)amine, N-phenyl-N-(4-phenylphenyl)amine, N,N-bis[4-(diphenyl) Amino)phenyl]amino, N,N-bis[3-(diphenylamino)phenyl]amino, n,N-bis[4-{Ν'-phenyl Ν'-(2-Naphthyl)amino}phenyl]amino, ν, Ν-bis[3 — {Ν'-stupyl- Ν'-(2-naphthyl)amino}phenyl]amino , Ν, Ν—double [4_ {Ν'-phenyl-indole-1-(1-naphthyl)amino}phenyl]amine, hydrazine, hydrazine-bis[3 — {Ν'-phenyl-Ν' — (1 -naphthyl)amino}phenyl]amino, anthracene, fluorene-bis[4-(9-oxindole-9-yl)phenyl]amino, hydrazine, hydrazine _ double [3 - (9 Η - Oxazole-9-yl)phenyl]amino, anthracene, fluorene-bis(4-renylphenyl)amino, hydrazine, hydrazine-bis[1 -(8-sulfonaphthyl)amine, ν, Ν-bis[2-(8-sulfo-naphthyl)]amino, &-(4-sulfophenyl)-N-[l-(8-sulfonaphthyl)]amino, Ν—( 4-sulfophenyl)-fluorene-[2-(8-sulfo-naphthyl)]amino, 3,6-disulfo- 9-oxazole- 9-yl, hydrazine, hydrazine-bis[4- {bis(4,-sulfophenyl)amino}phenyl]amino, hydrazine, hydrazine-bis[4-(3,6-disulfo- 9-oxindole-9-yl)phenyl]amine Base, ν, Ν — bis(4-nonylphenyl)amino, hydrazine, hydrazine-bis(4-ethylphenyl)amino, hydrazine, hydrazine-bis(4-n-propylphenyl)amino , Ν, Ν-bis (4-isopropyl) Phenyl)amine, anthracene, anthracene-bis(4-n-butylphenyl)amine, anthracene, anthracene-bis(4-isobutylphenyl)amine, anthracene, anthracene-bis (fourth second Butylphenyl) = phenyl, hydrazine, hydrazine - bis(4-t-butylphenyl)amine, hydrazine, hydrazine-bis(4-n-pentylphenyl), hydrazine, hydrazine-bis (4-iso) Amyl phenyl)amino, anthracene, fluorene-bis(4-n-pentylphenyl)^yl, anthracene, fluorene~~bis(4-monopentylphenyl)amino, hydrazine, hydrazine 4_n-hexylphenyl) Months, Ν, Ν-bis[4-(1-methylpentyl)]amino, anthracene, anthracene-bis[4~(4-indolyl- 2~ pentyl) Base) phenyl]amino group and the like. In the formula (1), the fluorene is preferably a divalent aromatic group having 4 to 9 carbon atoms. The group represented by -Υ- contains the general formula (lb): -A-(BA)u- (lb) (wherein A represents a divalent aromatic group, and _B_ represents a single bond, an alkylene group, _〇) _, -S-, -CO-, _s〇_, _s〇r, _SiH2_, and _siMe2, u represents an integer of 〇~2.) No base. Also, A may be bonded to each other to form a ring. u is preferably an integer of 〇~1. 22 200906909 A The number of rabbits 4 to 60 is 2 aryl 夭 f ± J_ or a divalent aromatic heterocyclic group. "Tujiajia' contains a divalent aromatic hydrocarbon group of 2 or more aromatic hydrocarbon groups Δ7 1 A or 2 substituted. The group is an unsubstituted or substituted ring group, and may be unsubstituted or preferably 6 to 3 Å. On the other hand, in the case of the divalent hydrocarbon group, the base carbon is in the range of 4 to 3 Å ":, 'substituted or substituted aromatic heterocyclic ring, for example, oxime (1) $ Or an aromatic hetero-indolyl group, 'Fangxiang smoky group' or aromatic miscible-I 90 , s-yl, 2,7-oxadiazole, 9, quinone diyl, and furan I, π two two, flower one base, 2,8~-two shame dragon vomiting _ J8~ than two base,

所示基及通式(比―2)Base and formula (ratio - 2)

(1 b -> 2) 23 200906909 基、1，8—祐二基、2,7-吟唑二基、3,7 本并吱喃二基及前述通式(lb — 1) ，5 基、2,7_第二基、9，1〇—葱: 二苯并嚷吩二基、3,7 —j(1 b -> 2) 23 200906909 base, 1,8-youdiyl, 2,7-carbazolediyl, 3,7 mercaptodiyl and the above formula (lb-1), 5-base, 2,7_Second base, 9,1〇-onion: dibenzoquinone diyl, 3,7 —j

b 代之5— 伸烷基，以碳數1〜6之伸妗萁如几佳。火双G之伸心基較佳，碳數1〜3之伸烧基更 f取代或經取代之伸院基之具體 3 ΐΐ t； ^ 1,3 伸=環伸己基、3,3,5-三甲伸庚基、u—二苯基亞曱基、基亞甲基、 ίίΐί，取代基，例如漱基、芳香族基或芳燒基。化ίίί之絲’例如:無取代或經取代之直鏈狀、分支鏈狀 ‘基、1 ί戌ΐί:基、第二丁基、第三丁基、正戊基、異戊基、 2H、丁^基、正已基、卜甲基戊基、4-甲基-2-戊基、〜屯/在/、2—乙基己基、正庚基、甲基己基、正辛基、1 甲I二f_V甘2 —丙基戊基、正壬基、2,2 —二曱基庚基、2,6 —二丄基庚基、3,5,5〜三甲基己基、正癸基、卜乙基辛基、正甲基癸基、正十三基、〗—己基庚基、正十四基、正 24 200906909 十五基、1一己基辛基、正十六基、環己基、環己基曱基、里丙基環己基)甲基、（2 —異丙基環己基)乙基、環戊基、2〜基0 3-二甲基丁基、U —二甲基己基、格烯基、異其土、丄 =，基、2—降如完甲基、丄—雙環[2.2 2]辛基、丄—金剛^、3 環Ϊί剛ί、甲甲基、環丁基、^甲峨基、4二甲基 %己基、3-甲基壤己基、2—甲基環己基、2,3—二土二曱ΐ環己基、2,6〜二甲基環己基、3,4-二甲基ί:二 —一甲基環己基、2,4,6 —三甲基環己基、33二又土、， 42,6=異丙基環己基、4〜第三丁基環己“ 、基、2-苯基環己基、環庚基、環辛=: 芳香:經取代之芳香族烴基或 ?6〜％者較佳。無取代或經取代之碳數石反數以4〜30者較佳。方香族雜3衣基中，構成環之芳香族烴基或芳香族雜環基芳香族烴基或芳香族雜产〜Χ之具體例所示者。 X1〜X4之芳香族烴基或料代基，例如與通式⑴之中伸垸基上之雜基基上之取代基同樣者。基較佳。芳院基之具體例，例碳數7〜20之芳燒 — 通式(1)中，Ari〜Ar4 之方烷基所示者。 ,取代之2價芳香族基，包了破 =可為相同或不同之無取代 !^30之2價芳香族雜環基1 A3〇4之2價芳香族煙基或之方香族烴基更佳。 f丞Ar〜Ar以相同基較佳，相同 “方香族基同樣者，斤不基，例如與通式(1) u .或一〇〜】之整數且B ㈣雄)之中中Υ之示基。又，Α可之方香族基，亦即 ^〜〜之2/芳^=鍵結成環。 A或日知基，以通式(a-3) 25 200906909 (a_3) too v (式中’ V表示0〜2之整數。）所示基較佳，v為〇〜1之整數更佳。 —與丁為擇自單鍵、—(CH2)t---CH=CH-、 • 、~*~s—、—CQ}Q2-、—CO—、—SO—、-sa 群組之基’彼此可為相㈤或不同，以單鍵、」 —〇---s---cq、2—所示基更佳。 10之整數較佳。Q1及Q2表示烷基或芳 t表示1〜20之整數，香族基，亦可彼此鐽紝士、卢u主-:二\ /入X仏小玩丞哀 j 2 --、不 u今、/丨、呈、你 Q及Q之烧基之具體例，例如前述—Β—所示伸絲上之燒 Q1及原子、絲或芳香族基基之具體例所示者峨之綱嶋，b Substituting 5—alkylene, with a carbon number of 1 to 6 as good as a few. The excision base of the fire double G is preferred, and the extension number of the carbon number 1 to 3 is more than the specific substitution of the substituted or substituted base 3 ΐΐ t; ^ 1,3 extension = ring extension hexyl, 3, 3, 5 a trimethyl-denyl group, a u-diphenylarylene group, a benzylidene group, an ylylene group, a substituent such as a fluorenyl group, an aromatic group or an aryl group. Ίίίί的丝', for example: unsubstituted or substituted linear, branched chain 'group, 1 ί戌ΐί: group, second butyl, tert-butyl, n-pentyl, isopentyl, 2H, Butyl, n-hexyl, benzylidene, 4-methyl-2-pentyl, hydrazine/in /, 2-ethylhexyl, n-heptyl, methylhexyl, n-octyl, 1 methyl I f_V Gan 2 -propylpentyl, n-decyl, 2,2-didecylheptyl, 2,6-didecylheptyl, 3,5,5-trimethylhexyl, n-decyl, bisethyl Base, n-methyl decyl, n-tridecyl, hexyl heptyl, n-tetradecyl, n = 24 200906909 fifteen, 1-hexyloctyl, n-hexadecyl, cyclohexyl, cyclohexyl fluorenyl, Ripropylcyclohexyl)methyl, (2-isopropylcyclohexyl)ethyl, cyclopentyl, 2~yl 0 3-dimethylbutyl, U-dimethylhexyl, gekenyl, heterogeneous Soil, 丄 =, base, 2 - such as methyl, hydrazine - bicyclo [2.2 2] octyl, hydrazine - Donkey Kong ^, 3 ring Ϊ ί Gang, methyl, cyclobutyl, methyl thiol, 4 Dimethyl% hexyl, 3-methyllopylenyl, 2-methylcyclohexyl, 2,3-di-dioxacyclohexyl, 2,6 Dimethylcyclohexyl, 3,4-dimethyl ί: bis-methylcyclohexyl, 2,4,6-trimethylcyclohexyl, 33 bis-xyl, 42,6 = isopropylcyclohexyl 4~T-butylcyclohexanyl, phenyl, 2-phenylcyclohexyl, cycloheptyl, cyclooctyl =: aromatic: substituted aromatic hydrocarbon group or ?6~% is preferred. Unsubstituted or substituted The carbon number of the carbon number is preferably from 4 to 30. The aromatic aromatic hydrocarbon group or the aromatic heterocyclic aromatic hydrocarbon group or the aromatic heterogeneous product of the ring is shown in the formula. The aromatic hydrocarbon group or the substituent group of X1 to X4 is, for example, the same as the substituent on the hetero group on the fluorene group in the formula (1). The group is preferably a specific example of the aryl group, and the carbon number is exemplified. 7 to 20 of the aromatic burning - in the general formula (1), the Ari ~ Ar4 square alkyl group. The substituted divalent aromatic group, wrapped broken = can be the same or different unsubstituted! ^ 30 The divalent aromatic nicotyl group or the divalent aromatic hydrocarbon group of the divalent aromatic heterocyclic group 1 A3〇4 is more preferable. f丞Ar~Ar is preferably the same group, and the same is the same as the square fragrance group. , for example, an integer with the formula (1) u. or a 〇~] (Iv) Male B) shown in the group in Υ. In addition, the square of the fragrant group, that is, ^~~2/fang^=bonded into a ring. A or a Japanese base is represented by the formula (a-3) 25 200906909 (a_3) too v (wherein 'V represents an integer of 0 to 2). Preferably, the base is more preferably v is an integer of 〇~1. - and Ding is selected from the single bond, -(CH2)t---CH=CH-, •, ~*~s-, -CQ}Q2-, -CO-, -SO-,-sa group basis 'It can be phase (five) or different from each other, and the base shown by a single bond, "-〇---s---cq, 2- is better. An integer of 10 is preferred. Q1 and Q2 indicate that the alkyl group or the aryl t represents an integer of 1 to 20, and the scent group can also be a gentleman, a ru, a master, a singer, a singer, a singer, a singer, a singer, a singer, a singer, a singer, a singer Specific examples of the base of the group of the Q, Q, and Q, for example, the above-mentioned Β--showing the outline of the burnt Q1 on the wire and the atomic, silk or aromatic base,

E之烷基之具體例，例如Q1及Q2之烷基之罝辨之芳香族基^如Q1及Q2之芳香族基之具體例所^所示者，E ?ί、;?基S香族雜環基’例如χ1〜X4之具體例所示者 η 本發明之含有續基之高分子化合物 =通式(2)所示錢單位至少〗個之高分子化二子鏈中，有用中間體(以下稱為「中間體高分子化“ ^，通式(2) 2分子1 化合f，以高分子鏈中具有將通式(2)之」中心^石頁基 f物之χ〜X4、Υ及苯環中至少1個以綠基體南分子化 1個較佳。、取代之重複單位至少 26 200906909 XVX2Specific examples of the alkyl group of E, for example, the aromatic group of the alkyl group of Q1 and Q2, such as the specific examples of the aromatic group of Q1 and Q2, E?, ?? The heterocyclic group ', for example, a specific example of χ1 to X4, η. The polymer compound containing a thiol group of the present invention = at least one of the polymerized di-sub-chains of the formula (2), and a useful intermediate ( Hereinafter, it is referred to as "intermediate polymerization" ^, and the formula (2) 2 molecule 1 is compounded with f, and the polymer chain has a structure of the formula (2). And at least one of the benzene rings is preferably molecularly catalyzed by a green matrix. The repeating unit of substitution is at least 26 200906909 XVX2

(a-1) ς!·Η H Q 為擇自於單鍵、0、s、CH2、CMe2、c〇、so、so2、 SlH2 Sfe2所構成群組之基，k表示G〜2之整數+ 2(a-1) ς!·Η H Q is the base of the group consisting of single keys, 0, s, CH2, CMe2, c〇, so, so2, and SlH2 Sfe2, and k is the integer of G~2 + 2

之含有續基之高分子化合物，可藉由將高分子鏈中具 g例如k式⑴所示重複單位至少、J個之高分子化合物予以續化而 _又，對於在高分子鏈中具有通式(1)所示重複單位至少1個之咼分子化合物導入磺基而成之含有磺基之高分子化合物中，亦可，成鹽。鹽不特別限制，例如鐘、納、鉀、_、轉無機鹽類、氛=甲基胺、三乙基胺K、咪料有機賴或與胺基酸類又，高分子鏈中具有通式⑴所示重複單位至少j個之高分化合物之數平均分子量，補·H聚苯乙稀換算刀〜1000000，較佳為3000〜500000。更佳為4〇〇〇〜2〇〇〇〇〇。本發 27 200906909 明之含有磺基之高分子化合物之數平均分子量亦同。又，高分子鏈中具有通式(】)所示重複單位至少1個之高八匕=，可將為聚合反應部位之末端宫能基利用無取代或：：分ϊίϊϊί、二取代胺基、直鍵、分支键或環狀貌基、具直鏈) 取ίϊίϊϊϊΐί綠氧基、羧基、絲基絲、綠等予以古八if明對於高分子鏈中具有通式⑴所示重複單位至少1個之 I二日日物導人有續基之構造的含有績基之高分子化合物，及，化上物」=刀子鏈中具有通式(1)所示重複單位至少1個之高分子例: 八體例’例如以下所例示者’但是本發明不限此等具體 1〜中，表示通式⑴之中pl〜p4為〇(零)者，下述表义广’各對應之具體例以Y、Ar1、Ar2、Ar3、Ar4、Τ1、T2、 m、η、X1、χ2、v3 χ1 χ2 Λ χ、Χ4之組合表不。The polymer compound containing a contiguous group can be renewed by a polymer compound having at least a repeating unit of at least g represented by formula (1) in the polymer chain, and further has a pass in the polymer chain. In the polymer compound containing a sulfo group in which at least one of the repeating unit compounds represented by the formula (1) is introduced into a sulfo group, a salt may be formed. The salt is not particularly limited, and is, for example, a bell, a nano, a potassium, a _, an inorganic salt, an aryl group, a methylamine, a triethylamine K, a sodium amide or an amino acid, and a polymer chain having a formula (1) The average molecular weight of the compound having at least j high-dividing compounds is shown in the repeating unit, and the H-polystyrene conversion knife is 1,000,000, preferably 3000 to 500000. More preferably 4〇〇〇~2〇〇〇〇〇. The number average molecular weight of the polymer compound containing a sulfo group is also the same as that of the present invention. Further, in the polymer chain, there is at least one repeating unit represented by the formula (]), and the upper end of the polymerization reaction site can be used as an unsubstituted or ::: ϊ ϊϊ ϊϊ 、, disubstituted amine group, Straight bond, branch key or cyclic base, with linear chain) ϊ 绿绿 green 、羧基绿绿绿绿绿绿绿绿绿绿绿绿绿对于对于对于对于对于对于对于对于对于对于对于对于对于对于对于对于对于对于对于对于对于对于对于对于对于对于In the case of a polymer compound containing a base of a structure having a continuation basis, and a chemical substance of the first day of the present invention, a polymer having at least one repeating unit represented by the general formula (1) in the knife chain is as follows: The eight-body example 'is exemplified below', but the present invention is not limited to the specific ones, and the pl~p4 in the general formula (1) is 〇 (zero), and the following examples are broadly defined. , Ar1, Ar2, Ar3, Ar4, Τ1, T2, m, η, X1, χ2, v3 χ1 χ2 Λ χ, Χ4 combination of the table.

Tr=Tr=

(R- 1) X4.%3 28 200906909 【表1】(R-1) X4.%3 28 200906909 [Table 1]

29 20090690929 200906909

30 200906909 【表3】例示化合物編號 Y Ar\ Ar3 n, m τ'τ2 Ar2, Ar4 χ!νΆ A2-1 0 / 〇ώ〇 A2-2 0 / C6H,3·^—^C6H,3 A2-3 "^Sjr^YJT 0 / σΝΌ A2-4 0 / A2-5 0 / A2-6 0 / σΝχ9 A2-7 <y〇r 0 / / σΝ€〇 A2-8 -QrQr 0 / / aNx^ A2-9 0 / / A2-10 ~Ότ 0 / / σΝχχ£) ό 31 20090690930 200906909 [Table 3] Exemplary compound number Y Ar\ Ar3 n, m τ'τ2 Ar2, Ar4 χ!νΆ A2-1 0 / 〇ώ〇A2-2 0 / C6H,3·^—^C6H,3 A2- 3 "^Sjr^YJT 0 / σΝΌ A2-4 0 / A2-5 0 / A2-6 0 / σΝχ9 A2-7 <y〇r 0 / / σΝ€〇A2-8 -QrQr 0 / / aNx^ A2-9 0 / / A2-10 ~Ότ 0 / / σΝχχ£) ό 31 200906909

【表4】【Table 4】

32 200906909 【表5】例示化合物編號 Y Ar1, Ar3 n, m T1. T2 Ar2, Ar4 χνΆ A3-1 HjC ch3 0 / / αΝΌ A3-2 CbHit CsH17 0 / / αΝΌ A3-3 H3C CH, 0 / / A3-4 HaC CH3 0 / / 〇ώ〇 A3-5 ο- ^8^17,〇8Η17 0 / / 0¾ A3-6 HjC CH, 0 / / A3-7 Ό~ H3C CH, <P〇r 0 / / ㈣购㈣ A3-8 H3c ch3 0 / / α'ι? A3-9 H3C CH, 0 / / αΝ€〇 A3-10 h3c ch3 0 / / σΝ〇ο 33 / κ 200906909【表6】例示化合物編號. Υ Ar\ Ar3 n, m t\t2 Ar2, Ar4 V，〆％ Α3-1 1 叹CH， 0 / / 〇Ci'Clo Α3-1 2 ~Qr H,C CH, 0 / // oHnNo ό AS-13 ~J\JT HjC CH, 0 / aMi>Nx>wX) ό ό A3-14 ~J^)r H3C CH, 0 / aNx>^) Α3-1 5 h3CvCH, ~^〇r 0 / αχ^Νχ>Νρ i/ Α3-16 "Qr H3C CH, 0 / 0¾¾ ό Α3-1 7 ~Qr H3C CH, ^>b- 0 / / ό Α3-1 8 0 / / σΝχχχτ° ό Α3-19 ~^]r HjC CH， 0 / / 34 200906909 【表7】例示化合物編號 Y Ar1, Ar3 n, m τ'τ2 Ar2, Ar4 V ./v A4-1 普 0 / / 0¾ A4-2 XT 0 / / 0¾ A4-3 备 0 / / 〇rNO A4-4 0 / / 0¾ A4-5 0 // / αΝΌ A4-6 ~^JT <P〇r 0 / / 0¾ A4-7 0 / / 咖 A4-8 ~JOr 0 / / 〇ώ〇 A4-9 9 0 / / 0¾ A4-10 ? ~^cy(y~ 0 / / 0¾ A4-1 1 ~^)r 0 / / αΝΌ A4-1 2 Or 0 / / 0¾ 35 200906909 【表8】32 200906909 [Table 5] Exemplary compound number Y Ar1, Ar3 n, m T1. T2 Ar2, Ar4 χνΆ A3-1 HjC ch3 0 / / αΝΌ A3-2 CbHit CsH17 0 / / αΝΌ A3-3 H3C CH, 0 / / A3-4 HaC CH3 0 / / 〇ώ〇A3-5 ο- ^8^17,〇8Η17 0 / / 03⁄4 A3-6 HjC CH, 0 / / A3-7 Ό~ H3C CH, <P〇r 0 / / (4) Purchase (4) A3-8 H3c ch3 0 / / α'ι? A3-9 H3C CH, 0 / / αΝ€〇A3-10 h3c ch3 0 / / σΝ〇ο 33 / κ 200906909 [Table 6] Illustrative compounds No. Υ Ar\ Ar3 n, mt\t2 Ar2, Ar4 V, 〆% Α3-1 1 叹CH, 0 / / 〇Ci'Clo Α3-1 2 ~Qr H,C CH, 0 / // oHnNo ό AS -13 ~J\JT HjC CH, 0 / aMi>Nx>wX) ό ό A3-14 ~J^)r H3C CH, 0 / aNx>^) Α3-1 5 h3CvCH, ~^〇r 0 / αχ^ Νχ>Νρ i/ Α3-16 "Qr H3C CH, 0 / 03⁄43⁄4 ό Α3-1 7 ~Qr H3C CH, ^>b- 0 / / ό Α3-1 8 0 / / σΝχχχτ° ό Α3-19 ~ ^]r HjC CH, 0 / / 34 200906909 [Table 7] Exemplary compound number Y Ar1, Ar3 n, m τ'τ2 Ar2, Ar4 V ./v A4-1 Pu 0 / / 03⁄4 A4-2 XT 0 / / 03⁄4 A4-3 Standby 0 / / 〇rNO A4-4 0 / / 0 3⁄4 A4-5 0 // / αΝΌ A4-6 ~^JT <P〇r 0 / / 03⁄4 A4-7 0 / / Coffee A4-8 ~JOr 0 / / 〇ώ〇A4-9 9 0 / / 03⁄4 A4-10 ? ~^cy(y~ 0 / / 03⁄4 A4-1 1 ~^)r 0 / / αΝΌ A4-1 2 Or 0 / / 03⁄4 35 200906909 [Table 8]

36 200906909 【表9】36 200906909 [Table 9]

例示化合物編號 Y Ar1, At·3 n, m T1,T2 Ar2, Ar4 XV〜〜巳 1-11 -a- 0 / / σΝ€ι Θ1-12 & -o- 0 / / αΝΌ 巳 1-13 ch3 〇tp- -o 0 / / σΝΌ B1-14 0 / / αΝο 巳卜15 ~Q)~ 0 / / σΝΌ B1-16 CeH|3 CgH ,3 0 / / σΝΌ 巳 1-17 ^8^!? CeH17 ~Q)~ 0 / / σΝΌ 巳 1-18 Op pa 0 // / σΝΌ 巳 1-19 OP 〇- 0 / / σΝΌ 巳 1-20 tr 0 / / σΝΌ 巳 1-21 i/a 0 / / σΝΌ 巳 1-22 j〇rgXX 吾 0 / / σΝΌ 巳 1-23 M 6 2 ^Sia 0 / / σΝΌ B1-24 0 σΝΌ 37 200906909 【表10】Exemplary compound numbers Y Ar1, At·3 n, m T1, T2 Ar2, Ar4 XV~~ 巳1-11 -a- 0 / / σΝ€ι Θ1-12 & -o- 0 / / αΝΌ 巳1-13 Ch3 〇tp- -o 0 / / σΝΌ B1-14 0 / / αΝο 巳卜 15 ~Q)~ 0 / / σΝΌ B1-16 CeH|3 CgH ,3 0 / / σΝΌ 巳1-17 ^8^!? CeH17 ~Q)~ 0 / / σΝΌ 巳1-18 Op pa 0 // / σΝΌ 巳1-19 OP 〇- 0 / / σΝΌ 巳1-20 tr 0 / / σΝΌ 巳1-21 i/a 0 / / ΝΌ ΝΌ 巳 1-22 j〇rgXX 吾 0 / / σΝΌ 巳 1-23 M 6 2 ^Sia 0 / / σΝΌ B1-24 0 σΝΌ 37 200906909 [Table 10]

/ 例示化合物編號 Y Ar1, Ar3 n, m T1,T2 Ar2, Ar4 ν.Λ 巳2-1 XX 0 / / 0¾ 巳2-2 JCX 0 / / 巳2-3 0 / // σΝΌ 巳2-4 0 / / 〇ΓΝΌ B2-5 0 / / 咖巳2-6 0 / / αΝΌ 巳2-7 0 / / 0¾ 巳2-8 % -O^O- 0 / / σΝΌ 巳2-9 0 / / αΝο 巳 2-10 ~J\)rl\)r 0 / σΝΌ 38 200906909 【表11】例示化合物編號 Y Ar1, Ar3 n, m 丁1,T2 Ar2, Ar4 巳 2-11 导Or 0 / / B2-12 0 / / σΝΌ 巳 2-13 ch3 ch3 0 / / σΝΌ 巳 2'14 h3c ch3 ~^y~Qr 0 / / σΝΌ 巳 2-15 0 / / 巳 2,16 C8H17,C9H17 〜cA> 0 / σΝΌ 巳 2-17 0 / 巳2M8 qp pa 0 / / 咖m B2-19 xrs\x 0 / / 0¾ B2-20 tr 0 / / αΝΌ 巳 2-21 ^0~0" 0 / σΝτ〇巳 2-22 0 / / σΝΌ B2-23 M jaSiTa 0 / 39 200906909 【表12】例示化合物編號 Y Ar1, Ar3 n, m t\t2 Ar2, Ar4 χνΆχ3 巳3-1 众 H3C ch3 0 / / 0¾ 巳3-2 众 h3c ch3 0 / / 巳3-3 H3C CH, 0 / / 〇τΝΌ 巳3-4 H3c CH3 0 / / σΝτ〇巳3-5 > h3c ch3 0 / / 咖巳3-6 H3C CH, 0 / / Cs〜m 巳3-7 言 HsC CH3 0 / / αΝο 巳3-8 H3C CH, 0 / // 咖巳3-9 ch3 ^Qr 0 / / σΝΌ 巳 3-10 <P〇r H3c CHj 0 / / αΝο 40 200906909 【表13】/ Illustrative compound number Y Ar1, Ar3 n, m T1, T2 Ar2, Ar4 ν.Λ 巳2-1 XX 0 / / 03⁄4 巳2-2 JCX 0 / / 巳2-3 0 / // σΝΌ 巳2-4 0 / / 〇ΓΝΌ B2-5 0 / / Curry 2-6 0 / / αΝΌ 巳 2-7 0 / / 03⁄4 巳 2-8 % -O^O- 0 / / σΝΌ 巳2-9 0 / / αΝο巳2-10 ~J\)rl\)r 0 / σΝΌ 38 200906909 [Table 11] Exemplary compound number Y Ar1, Ar3 n, m D1, T2 Ar2, Ar4 巳2-11 Guide Or 0 / / B2-12 0 / / σΝΌ 巳2-13 ch3 ch3 0 / / σΝΌ 巳2'14 h3c ch3 ~^y~Qr 0 / / σΝΌ 巳2-15 0 / / 巳2,16 C8H17,C9H17 ~cA> 0 / σΝΌ 巳2-17 0 / 巳2M8 qp pa 0 / / 咖 m B2-19 xrs\x 0 / / 03⁄4 B2-20 tr 0 / / αΝΌ 巳2-21 ^0~0" 0 / σΝτ〇巳2-22 0 / / σΝΌ B2-23 M jaSiTa 0 / 39 200906909 [Table 12] Illustrated compound number Y Ar1, Ar3 n, mt\t2 Ar2, Ar4 χνΆχ3 巳3-1 H3C ch3 0 / / 03⁄4 巳3-2 Public h3c ch3 0 / / 巳3-3 H3C CH, 0 / / 〇τΝΌ 巳3-4 H3c CH3 0 / / σΝτ〇巳3-5 > h3c ch3 0 / / Curry 3-6 H3C CH, 0 / / Cs~m 巳3-7 言HsC CH3 0 / / αΝο 巳3-8 H3C CH, 0 / // Curry 3-9 ch3 ^Qr 0 / / σΝΌ 巳3-10 <P〇r H3c CHj 0 / / αΝο 40 200906909 [Table 13]

例示化合物編號 Y Ar1, Ar3 n, m T1, T2 Ar2, Ar4 V ,X4 〜巳 3-11 m3c ch3 0 / / 0¾ 巳 3-12 普~〇 H5C ch3 0 / / αΝΌ 巳 3-13 HjC CH3 0 / / σΝΌ B3-14 ch3 ch3 h3c ch3 ~^o~ 0 / / αΝΌ B3-15 h3c ch3 H3C CH3 0 / / σΝΌ 巳 3-16 h3c ch3 ~φ> 0 / / 〇„Η,^αίΗΐ3 B3-17 CgHiTCaHi? ^CH> M ch3 0 / / 〇τΝτ〇 B3-1S Q^17,Q^17 HjC CH, 0 / / 巳 3-19 qp HaC CH3 0 / / c„h,3-C^ ^ο,η,, 巳 3-20 〇S> xrhx H3C CH, <^〇r 0 / / σΝΌ B3-21 XX h3c ch3 0 / / αΝο 巳 3-22 h3c ch3 0 / / αΝΌ 巳 3-23 H3C CH3 0 / / σΝΌ 巳 3-24 Me2 jaSia h3c ch3 0 / / σΝΌ 41 200906909 【表14】Exemplary compound numbers Y Ar1, Ar3 n, m T1, T2 Ar2, Ar4 V , X4 〜巳3-11 m3c ch3 0 / / 03⁄4 巳3-12 Pu ~〇H5C ch3 0 / / αΝΌ 巳3-13 HjC CH3 0 / / σΝΌ B3-14 ch3 ch3 h3c ch3 ~^o~ 0 / / αΝΌ B3-15 h3c ch3 H3C CH3 0 / / σΝΌ 巳3-16 h3c ch3 ~φ> 0 / / 〇„Η,^αίΗΐ3 B3-17 CgHiTCaHi? ^CH> M ch3 0 / / 〇τΝτ〇B3-1S Q^17, Q^17 HjC CH, 0 / / 巳3-19 qp HaC CH3 0 / / c„h,3-C^ ^ο, η,, 巳3-20 〇S> xrhx H3C CH, <^〇r 0 / / σΝΌ B3-21 XX h3c ch3 0 / / αΝο 巳3-22 h3c ch3 0 / / αΝΌ 巳3-23 H3C CH3 0 / / σΝΌ 巳3-24 Me2 jaSia h3c ch3 0 / / σΝΌ 41 200906909 [Table 14]

42 200906909 【表15】42 200906909 [Table 15]

例示化合物編號 Y Ar1, Ar3 n, m T'T2 Ar2, Ar4 巳 4-11 普分 0 / / 〇ώ〇 B4-12 ~o~ 0 / / 〇ώ〇 B4-13 ch3 ~o~ 0 / / 〇ώ〇巳 4-14 h3c ch3 Or 0 / / 0¾ B4-15 ~^\)γ 0 / / 0¾ 巳 4-16 'J\)r 0 / / 0¾ 巳 4-17 C8H1^C8H17 ~JOr 0 / / 训典心巳 4-18 qp ρχχ ~o~ 0 / / 0¾ 巳 4-19 Or 0 / / 〇ώ〇巳 4-20 tr ~^\)γ 0 / / 〇ώ〇巳 4-21 jyxx ~JOr 0 / / 〇ώ〇 B4-22 ~o~ 0 / / 0¾ 巳 4-23 Me^ jaSixx ~Qt~ 0 / / 0¾ 43 200906909 【表16】例示化合物編號 Y Ar\ Ar3 n, m t\t2 Ar2, Ar4 χνχ2 χ4^χχ3 B5-1 ja 0 / / 0¾ 巳5-2 0 / / 0¾ 巳5-3 0 / / 0¾ 巳5-4 0 / / 〇ώ〇 B5-5 0 / / c6H,3^mCeHl3 巳5-6 曾 0 / / 0¾ B5-7 -ΟΌ- 0 / / 〇ώ〇巳5-8 &5 ~Or^y~ 0 / / 〇ώ〇巳5-9 0 / / 0¾ 巳 5-10 ~Φ> 0 / / 0¾ 44 200906909 【表17】 fIllustrative compound number Y Ar1, Ar3 n, m T'T2 Ar2, Ar4 巳4-11 general score 0 / / 〇ώ〇B4-12 ~o~ 0 / / 〇ώ〇B4-13 ch3 ~o~ 0 / / 〇ώ〇巳4-14 h3c ch3 Or 0 / / 03⁄4 B4-15 ~^\)γ 0 / / 03⁄4 巳4-16 'J\)r 0 / / 03⁄4 巳4-17 C8H1^C8H17 ~JOr 0 / / Training Mind 4-18 qp ρχχ ~o~ 0 / / 03⁄4 巳4-19 Or 0 / / 〇ώ〇巳4-20 tr ~^\)γ 0 / / 〇ώ〇巳4-21 jyxx ~ JOr 0 / / 〇ώ〇B4-22 ~o~ 0 / / 03⁄4 巳4-23 Me^ jaSixx ~Qt~ 0 / / 03⁄4 43 200906909 [Table 16] Example compound number Y Ar\ Ar3 n, mt\t2 Ar2 , Ar4 χνχ2 χ4^χχ3 B5-1 ja 0 / / 03⁄4 巳5-2 0 / / 03⁄4 巳5-3 0 / / 03⁄4 巳5-4 0 / / 〇ώ〇B5-5 0 / / c6H,3^ mCeHl3 巳5-6 曾0 / / 03⁄4 B5-7 -ΟΌ- 0 / /〇ώ〇巳5-8 &5 ~Or^y~ 0 / / 〇ώ〇巳5-9 0 / / 03⁄4 巳5 -10 ~Φ> 0 / / 03⁄4 44 200906909 [Table 17] f

例示化合物編號 Y Ar1, Ar3 n, m t\t2 Ar2, Ar4 巳 5-11 0 / / 0¾ B5-12 0 / / 〇ώ〇巳 5-13 ch3 ch3 0 / / 0¾ 巳 5-14 h3c ch3 χΛχ 0 / / 〇ώ〇巳 5-15 0 / / 0¾ 巳 5-16 0 / / 0¾ 巳 5-17 ^8Ηΐ7,〇9Η17 ^CH> 0 / / C6H13·^—O'CeH^ B5-18 Op mx ^)~G~ 0 / / 0¾ B5-19 〇〇 0 / / 0¾ 巳 5-20 tr 0 / / 0¾ 巳 5-21 j〇\X 0 / / 0¾ B5-22 ^a'xx 0 / / 〇ώ〇巳 5-23 Me3 uSiia 0 / / 0¾ 45 200906909 【表18】Exemplary compound number Y Ar1, Ar3 n, mt\t2 Ar2, Ar4 巳5-11 0 / / 03⁄4 B5-12 0 / / 〇ώ〇巳5-13 ch3 ch3 0 / / 03⁄4 巳5-14 h3c ch3 χΛχ 0 / / 〇ώ〇巳5-15 0 / / 03⁄4 巳5-16 0 / / 03⁄4 巳5-17 ^8Ηΐ7,〇9Η17 ^CH> 0 / / C6H13·^—O'CeH^ B5-18 Op mx ^ )~G~ 0 / / 03⁄4 B5-19 〇〇0 / / 03⁄4 巳5-20 tr 0 / / 03⁄4 巳5-21 j〇\X 0 / / 03⁄4 B5-22 ^a'xx 0 / / 〇ώ 〇巳5-23 Me3 uSiia 0 / / 03⁄4 45 200906909 [Table 18]

例示化合物編號 Y Ar\ Ar3 n, m T\Ta Ar2, Ar4 XV〜〜 B6-1 众 h3c ch3 0 / / 0¾ 巳6-2 XX h3c CH3 0 / / CeH13^JCI^-^'C6H13 巳6-3 H3C CH, r^Cr · 0 / / 〇ώ〇 B6-4 0 / / 0¾ 巳6-5 H3C CHj 0 / / 0¾ 巳6-6 H3C CH, 0 / / 0¾ 巳6-7 首 H3C CH, 0 / / 0¾ 巳6-8 H3c ch3 <^〇r 0 / / 〇ώ〇巳6-9 h3c ch3 0 / / 0¾ B6-10 HjC CH3 ^P〇~ 0 / / 0¾ 46 200906909 【表19】Illustrative compound number Y Ar\ Ar3 n, m T\Ta Ar2, Ar4 XV~~ B6-1 public h3c ch3 0 / / 03⁄4 巳6-2 XX h3c CH3 0 / / CeH13^JCI^-^'C6H13 巳6- 3 H3C CH, r^Cr · 0 / / 〇ώ〇B6-4 0 / / 03⁄4 巳6-5 H3C CHj 0 / / 03⁄4 巳6-6 H3C CH, 0 / / 03⁄4 巳6-7 First H3C CH, 0 / / 03⁄4 巳6-8 H3c ch3 <^〇r 0 / / 〇ώ〇巳6-9 h3c ch3 0 / / 03⁄4 B6-10 HjC CH3 ^P〇~ 0 / / 03⁄4 46 200906909 [Table 19]

例示化合物編號 Y Ar1, Ar3 n, m T'T2 Ar2, Ar4 V .〆％巳 6-1 1 H3c ch3 ~0-Or 0 // / 0¾ 巳6M2 h3c ch3 ^〇T 0 / / 〇ώ〇 B6-13 H3C CH, 0 / / 〇ώ〇巳 6-14 ch3 ch3 HjCvCH3 0 / / 〇ώ〇巳 6-15 h3c ch3 xj'xy h3c CH3 0 / / 0¾ 巳6-16 0 / / CsH)3JD—〇LCeHi3 巳 6-17 CeHiiCgH! 7 <H> h3c CH, 0 / / 0¾ 巳 6-18 CgH^CgH-i 7 H3c CHj ^Or 0 / / 巳 6-19 mx HjC ch. 0 / / 〇ώ〇 B6-20 xrs^a h3c ch3 0 / 0¾ 巳 6-21 tr HjC CH3 0 / / 〇ώ〇巳 6-22 j〇\x H3C CH, ~Φ〇τ 0 / 0¾ B6-23 HjC CH, ^fOr 0 / / 0¾ 巳 6-24 Me2 HjC CH3 ^>b- 0 / / 0¾ 47 200906909 【表20】例示化合物編號 Y Ar1, Ar3 n, m T1,T2 Ar2, Ar4 V，八 C1-1 1 単秸含 CH3 0¾ C1-2 ~^)r 1 単结含 CH, -w> c6H,3^aCsHi3 C1-3 ~Q]r 1 単結含 H^： CH3 ~^Or aNx) C1-4 1 単結含 CH3 c3h,^〇-cbh„ C1-5 ~^y~ 1 単结含 HiC CH, -dV C8h17^€iC6Hi3 C1-6 1 単秸合 ^Όγ aNx? C1-7 ~J\jT ~Qlr 1 単结合 CH, -〇5> aNO〇 C1-8 ~Qlr 1 単秸合 CH3 -W> C1-9 ~Qt~ ~Jvy~ 1 単ί吉合 hVh, C1-10 ^JT 単秸合 CH, ~^〇r aNoNx) ό 48 200906909 【表21】Exemplary compound number Y Ar1, Ar3 n, m T'T2 Ar2, Ar4 V .〆% 巳6-1 1 H3c ch3 ~0-Or 0 // / 03⁄4 巳6M2 h3c ch3 ^〇T 0 / / 〇ώ〇B6 -13 H3C CH, 0 / / 〇ώ〇巳6-14 ch3 ch3 HjCvCH3 0 / / 〇ώ〇巳6-15 h3c ch3 xj'xy h3c CH3 0 / / 03⁄4 巳6-16 0 / / CsH)3JD— 〇LCeHi3 巳6-17 CeHiiCgH! 7 <H> h3c CH, 0 / / 03⁄4 巳6-18 CgH^CgH-i 7 H3c CHj ^Or 0 / / 巳6-19 mx HjC ch. 0 / / 〇ώ 〇B6-20 xrs^a h3c ch3 0 / 03⁄4 巳6-21 tr HjC CH3 0 / / 〇ώ〇巳6-22 j〇\x H3C CH, ~Φ〇τ 0 / 03⁄4 B6-23 HjC CH, ^ fOr 0 / / 03⁄4 巳6-24 Me2 HjC CH3 ^>b- 0 / / 03⁄4 47 200906909 [Table 20] Exemplary compound numbers Y Ar1, Ar3 n, m T1, T2 Ar2, Ar4 V, eight C1-1 1単 straw contains CH3 03⁄4 C1-2 ~^)r 1 単 knot contains CH, -w> c6H,3^aCsHi3 C1-3 ~Q]r 1 単 knot contains H^: CH3 ~^Or aNx) C1-4 1単 knot contains CH3 c3h, ^〇-cbh„ C1-5 ~^y~ 1 単 knot contains HiC CH, -dV C8h17^€iC6Hi3 C1-6 1 単合 Ό Ό a a nx? C1-7 ~J\jT ~ Qlr 1 単 combines CH, -〇5> aNO〇C1-8 ~Qlr 1 単合CH3 -W> C1-9 ~Qt~ ~Jvy~ 1 単ί吉合 hVh, C1-10 ^JT 単草合CH, ~^〇r aNoNx) ό 48 200906909 [Table 21]

例示化合物編號 Y Ar"1, Ar3 n, m T'T2 Ar2, Ar4 C1 Ί 1 1 單鍵 M ch3 ~φ> aNJ〇rNX>NJ〇 ό 6 C1-1 2 -Qr 1 單鍵 CH3 σΝ€^) C1-13 ^JT 1 單鍵 Hf CH3 ^J-Cr ^ ί/ C1-14 ~~Qr 1 單鍵 CH, V ~φ> ό C1-15 ~JOr 1 單鍵 CH3 〇ΓΝ〇Ν^ ό C1-16 ^~^JΓ ~J\JT 1 單鍵 Hi CH, σΝχχχτ° ό C1-17 ~JOr 1 單鍵 HVHa axg C1-1 8 <JT 單鍵 CH, C1-19 ~Qr 1 單鍵 αΝτ〇 C1-20 ~J\JT ^JT 1 單鍵 XX 49 200906909 【表22】例示化合物編號 Y Ar\ Ar3 n, m T1,T2 Ar2, Ar4 C2-1 H3C ch3 1 單鍵 αΝΌ C2-2 ^8^!? C8H17 1 單鍵 σΝο C2-3 ~〇~ H，C CH3 1 單鍵 7 C2-4 H3C CHj <β〇Γ 1 單鍵 0¾ C2-5 <y CeH17 C8H17 1 單鍵 ~~Qt~ 0¾ C2-6 HjC CH3 單鍵 ^JT CeH, C2-7 ~JOr h3c ch3 單鍵 C2-8 H3C^,CH3 ^Cr 單鍵 ~Qir σΝχ9 C2-9 H3C CH, ~o~(y~ 1 單鍵〇rNTO C2-10 CH, 1 單鍵 ^y~ 50 200906909 【表23】例示化合物編號 Y Ar1, Ar3 n, tn T'T2 Ar2, Ar4 V .Λ C2-1 1 h3cvCH, 1 單鍵 C2-12 H,C CH3 f 單鍵 σΝτχχ) ό C2-13 "Or HjC 〇H3 1 單鍵 ~^\jr αΝχ>ΝοΝΧ) ό ό C2-14 HaC CH, ^〇r 1 單鍵 ~〇~ σΝ€^ C2-1 5 h3c ch3 ~φ> 1 單鍵 a€rNt>,r) C2-16 h3C CH3 1 單鍵 ό C2-1 7 ^\jr H3C CH, t 單鍵分 αΝοΝ^ ό C2-1 8 H3c CH, -<Λ> 1 單鍵〇rNXXJ3r° ό C2-19 HjC CH, 1 單鍵 Or 51 200906909 【表24】Exemplary compound number Y Ar"1, Ar3 n, m T'T2 Ar2, Ar4 C1 Ί 1 1 single bond M ch3 ~φ>aNJ〇rNX>NJ〇ό 6 C1-1 2 -Qr 1 single bond CH3 σΝ€^ ) C1-13 ^JT 1 Single bond Hf CH3 ^J-Cr ^ ί/ C1-14 ~~Qr 1 Single bond CH, V ~φ> ό C1-15 ~JOr 1 Single bond CH3 〇ΓΝ〇Ν^ ό C1 -16 ^~^JΓ ~J\JT 1 Single key Hi CH, σΝχχχτ° ό C1-17 ~JOr 1 Single key HVHa axg C1-1 8 <JT single key CH, C1-19 ~Qr 1 Single key αΝτ〇 C1-20 ~J\JT ^JT 1 Single bond XX 49 200906909 [Table 22] Exemplary compound number Y Ar\ Ar3 n, m T1, T2 Ar2, Ar4 C2-1 H3C ch3 1 Single bond αΝΌ C2-2 ^8^ !? C8H17 1 Single key σΝο C2-3 ~〇~ H,C CH3 1 Single key 7 C2-4 H3C CHj <β〇Γ 1 Single key 03⁄4 C2-5 <y CeH17 C8H17 1 Single key~~Qt~ 03⁄4 C2-6 HjC CH3 Single key ^JT CeH, C2-7 ~JOr h3c ch3 Single key C2-8 H3C^,CH3 ^Cr Single key~Qir σΝχ9 C2-9 H3C CH, ~o~(y~ 1 single bond 〇rNTO C2-10 CH, 1 single bond ^y~ 50 200906909 [Table 23] Exemplary compound number Y Ar1, Ar3 n, tn T'T2 Ar2, Ar4 V .Λ C2-1 1 h3cvCH, 1 single bond C2- 12 H,C CH3 f Single key σΝτχχ) ό C2-13 "Or HjC 〇H3 1 Single key~^\jr αΝχ>ΝοΝΧ) ό ό C2-14 HaC CH, ^〇r 1 Single key~〇~ σΝ€ ^ C2-1 5 h3c ch3 ~φ> 1 single key a€rNt>,r) C2-16 h3C CH3 1 single key ό C2-1 7 ^\jr H3C CH, t single key division αΝοΝ^ ό C2-1 8 H3c CH, -<Λ> 1 Single key 〇rNXXJ3r° ό C2-19 HjC CH, 1 Single key Or 51 200906909 [Table 24]

例示化合物編號 Y Ar1, Ar3 n, m T1.T2 Ar2, Ar4 V .x，V D1-1 ~o~ 1 -〇- 0¾ D1-2 1 -o- CeHl3-O^C^CeH„ D1-3 ~J^)r 1 -o- σΝΌ D1 -4 ~J^jT 1 -o- ~o~ ιΓτΝγ^ι CbHiz-^^ ^^C0H17 D1-5 ~〇~ ™o~ 1 -o- D1-6 ~o~ 1 -o- D1-7 ~JOr 1 -〇- ~o~ σΝ€〇 D1-8 ~JVJT 1 -o- D1-9 ^Q~ ~^jt -o- D1 -10 ~o~ -ο- 〇rNXXJ〇 6 52 200906909 【表25】例示化合物編號 Y Ar\ Ar3 n, m t\t2 Ar2, Ar4 V ,X4 〜 D1-1 1 1 -o- aNoNdNjD ό ό D1-12 ~〇- 1 -0 - σΝ€^ρ D1-13 ~Qr 1 -0 - aN€rNx>Nr) ^ d/ D1-14 ~Όγ ~Qr 1 -o - ~J^jT ό D1 -1 5 ~Qr 1 -o- αΝΌΝ^ ό D1-16 ~Qr ~^JT O~ ό D1-17 ~o~ -Or 1 -o - σΝ^ D1-18 ~o~ 1 -o- Or 53 200906909 【表26】例示化合物編號 Y Ar1, Ar3 n, m T\T2 Ar2, Ar4 V ,x4〜 D2-1 -O- 1 -o- 〇ώ〇 D2-2 -〇 1 -o- ~dy^y~ D2-3 1 -o- αΝΌ D2-4 1 ~O^}~ D2-5 -ο- 1 -o- D2-6 1 -o- σΝχ9 D2-7 -Qir 1 -o- 〇rN€0 D2-8 ~JOr 1 -o- D2-9 ~Qir -o- ^Ch^D~ D2-10 ^)r 1 -o- αΝ€ίΝχ) ό 54 200906909 【表27】例示化合物編號 Y Ar1, Ar3 n, m t\t2 Ar2, Ar4 D2-1 1 1 -〇 - aN€rNx>Nj〇 ό ό D2-12 Or ^o~ 1 〇τΝτχ^ D2-13 1 -〇- D2-14 ~JOr 1 -o- αΝχ>5ί) ό D2-15 ~JVJT 1 ~0 — σΝΌι』 ό D2-16 ~^JT ~Qt~ 1 σΝχχο° ό D2-17 ~o- <xy σΝχ§ D2-18 ~o~· -o- (f^ 55 200906909 【表28】Exemplary compound number Y Ar1, Ar3 n, m T1.T2 Ar2, Ar4 V .x, V D1-1 ~o~ 1 -〇- 03⁄4 D1-2 1 -o- CeHl3-O^C^CeH„ D1-3 ~J^)r 1 -o- σΝΌ D1 -4 ~J^jT 1 -o- ~o~ ιΓτΝγ^ι CbHiz-^^ ^^C0H17 D1-5 ~〇~ TMo~ 1 -o- D1-6 ~o~ 1 -o- D1-7 ~JOr 1 -〇- ~o~ σΝ€〇D1-8 ~JVJT 1 -o- D1-9 ^Q~ ~^jt -o- D1 -10 ~o~ - Ο- 〇rNXXJ〇6 52 200906909 [Table 25] Illustrative compound number Y Ar\ Ar3 n, mt\t2 Ar2, Ar4 V , X4 ~ D1-1 1 1 -o- aNoNdNjD ό ό D1-12 ~〇- 1 - 0 - σΝ€^ρ D1-13 ~Qr 1 -0 - aN€rNx>Nr) ^ d/ D1-14 ~Όγ ~Qr 1 -o - ~J^jT ό D1 -1 5 ~Qr 1 -o- ΝΌΝ ό ό D1-16 ~Qr ~^JT O~ ό D1-17 ~o~ -Or 1 -o - σΝ^ D1-18 ~o~ 1 -o- Or 53 200906909 [Table 26] Illustrative compound number Y Ar1 , Ar3 n, m T\T2 Ar2, Ar4 V , x4~ D2-1 -O- 1 -o- 〇ώ〇D2-2 -〇1 -o- ~dy^y~ D2-3 1 -o- αΝΌ D2-4 1 ~O^}~ D2-5 -ο- 1 -o- D2-6 1 -o- σΝχ9 D2-7 -Qir 1 -o- 〇rN€0 D2-8 ~JOr 1 -o- D2 -9 ~Qir -o- ^Ch^D~ D2-10 ^)r 1 -o- αΝ€ίΝχ) ό 54 200906909 [Table 27] Illustrative compound number Y Ar1, Ar3 n, mt\t2 Ar2, Ar4 D2-1 1 1 -〇- aN€rNx>Nj〇ό ό D2-12 Or ^o~ 1 〇τΝτχ^ D2-13 1 -〇- D2-14 ~JOr 1 -o- αΝχ>5ί) ό D2-15 ~JVJT 1 ~0 — σΝΌι』 ό D2-16 ~^JT ~Qt~ 1 ΝχχΝχχο° ό D2-17 ~o- <xy σΝχ§ D2-18 ~o~· -o- (f^ 55 200906909 [Table 28]

例示化合物編號 Y Αγ1, Ar3 η, m τ\τ2 Ar2, Ar4 V ,X4 〜 D3-1 1 -ο- Ηί CH3 〇ώ〇 D3-2 ~ο~ 1 -ο- H^： CH3 ^j-〇- D3-3 1 -ο- CH, 咖 D3-4 ~ο~ 1 -ο- CH, -W> 〇8Ηι^〇ε8ΗΐΓ D3-5 ~^)τ 1 CH3 CeHl^NOc6H,3 D3-6 ~ο~ t —0一 -ob- σΝχ9 D3-7 -ο- CH3 σΝ€〇 D3-8 ~ο~ -ο - HjC CH3 αΝο^ D3-9 ~^jt ~ο~ -ο- ch3 D3-10 ^\)γ 1 -ο- Hyc ch3 ~Φ> αΝοΝο ό 56 200906909 【表29】例示化合物編號 Y Ar1, Ar3 n, m T'T2 Ar2, Ar4 D3-11 1 -o- CH, 〇lnJ〇tn€lnjD ό 0 D3-12 ~Ότ 1 -o- HP CH3 αΝχχ^) D3-13 1 -o- Hi CH3 <^Cr αχ/χ>ΝΧϊ ^ e/ D3-14 ~Qr 1 -o- CH3 ό D3-15 t -o- CH, ~O~xy ό D3-16 -o- CH, ~Φ> αΝ€ιΝο° ό D3-17 -o- CH3 crxg D3-18 -o- H#： CH, ~O-Qr 57 200906909 【表30】Illustrative compound number Y Αγ1, Ar3 η, m τ\τ2 Ar2, Ar4 V , X4 ~ D3-1 1 -ο- Ηί CH3 〇ώ〇D3-2 ~ο~ 1 -ο- H^: CH3 ^j-〇 - D3-3 1 -ο- CH, Coffee D3-4 ~ο~ 1 -ο- CH, -W> 〇8Ηι^〇ε8ΗΐΓ D3-5 ~^)τ 1 CH3 CeHl^NOc6H,3 D3-6 ~ο ~ t —0一-ob- σΝχ9 D3-7 -ο- CH3 σΝ€〇D3-8 ~ο~ -ο - HjC CH3 αΝο^ D3-9 ~^jt ~ο~ -ο- ch3 D3-10 ^\ γ 1 -ο- Hyc ch3 ~Φ> αΝοΝο ό 56 200906909 [Table 29] Exemplary compound number Y Ar1, Ar3 n, m T'T2 Ar2, Ar4 D3-11 1 -o- CH, 〇lnJ〇tn€lnjD ό 0 D3-12 ~Ότ 1 -o- HP CH3 αΝχχ^) D3-13 1 -o- Hi CH3 <^Cr αχ/χ>ΝΧϊ ^ e/ D3-14 ~Qr 1 -o- CH3 ό D3- 15 t -o- CH, ~O~xy ό D3-16 -o- CH, ~Φ> αΝ€ιΝο° ό D3-17 -o- CH3 crxg D3-18 -o- H#: CH, ~O- Qr 57 200906909 [Table 30]

例示化合物編號 Y Ar1, Ar3 n, m t\t2 Ar2, Ar4 E1-1 众 1 -o- 〇ΓΝΌ E1-2 b-q ~JOi~ 1 -o- αΝΌ E1-3 1 -o- <y σΝΌ E1-4 ~Qir 1 -o- σΝΌ E1-5 ~JOr 1 -0 - ^Qir σΝΌ E1-6 ^JT 1 -o- ~o~ E1-7 曾 ~JOr 1 -o - σΝΌ E1-8 ~Qir -o- 咖 E1-9 % ^jT ^JT αΝο E1 -10 ^JT -o- ~o~ αΝο 58 200906909 【表31】例示化合物編號 Y Ar1, Ar3 n, m t\t2 Ar2, Ar4 v，〆％ E1-1 1 1 -o- 0¾ Et-12 -o t -o- -o 0¾ E1 -13 ~^cy~ 1 -o- 〇rNO E1-14 ch3 ch3 1 -o- σΝΌ E1-1 5 h3c ch3 1 -o- aNO E1 -16 jcftx 1 -o- aNo E1-17 CeH,, CSH ,3 -〇 - 〇rNO E1-18 CgHn cbh17 ^0Γ —0- 咖 E1-19 Qp Svk Or -o - σΝο E1-20 xrs^a <)r -o- 咖 E1-21 tr ~J\JT 1 -o- ~〇~ σΝΌ E1-22 j〇\x 1 -o- 0¾ E1-23 jagbk -o 1 -o~ ~Qt~ 〇ΓΝΌ E1-24 Me2 jaSixx -^ir 1 -0" ^JT σΝΌ 59 200906909 【表32】Exemplary compound number Y Ar1, Ar3 n, mt\t2 Ar2, Ar4 E1-1 1 -o- 〇ΓΝΌ E1-2 bq ~JOi~ 1 -o- αΝΌ E1-3 1 -o- <y σΝΌ E1- 4 ~Qir 1 -o- σΝΌ E1-5 ~JOr 1 -0 - ^Qir σΝΌ E1-6 ^JT 1 -o- ~o~ E1-7 Zeng~JOr 1 -o - σΝΌ E1-8 ~Qir -o - Coffee E1-9 % ^jT ^JT αΝο E1 -10 ^JT -o- ~o~ αΝο 58 200906909 [Table 31] Exemplary compound numbers Y Ar1, Ar3 n, mt\t2 Ar2, Ar4 v, 〆% E1- 1 1 1 -o- 03⁄4 Et-12 -ot -o- -o 03⁄4 E1 -13 ~^cy~ 1 -o- 〇rNO E1-14 ch3 ch3 1 -o- σΝΌ E1-1 5 h3c ch3 1 -o - aNO E1 -16 jcftx 1 -o- aNo E1-17 CeH,, CSH ,3 -〇- 〇rNO E1-18 CgHn cbh17 ^0Γ —0- Coffee E1-19 Qp Svk Or -o - σΝο E1-20 xrs ^a <)r -o- 咖 E1-21 tr ~J\JT 1 -o- ~〇~ σΝΌ E1-22 j〇\x 1 -o- 03⁄4 E1-23 jagbk -o 1 -o~ ~Qt ~ 〇ΓΝΌ E1-24 Me2 jaSixx -^ir 1 -0" ^JT σΝΌ 59 200906909 [Table 32]

例示化合物編號 Y Ar1, Ar3 n, m T'T2 Ar2, Ar4· V，八 E2-1 1 -o - σΝΌ E2-2 1 -o - 0¾ E2-3 1 -o- ~G^O~ 〇τΝΌ E2-4 ^JT 1 -o- σΝΌ E2-5 1 -o- αΝΌ E2-6 ~^JT 1 -o- CeH,^N€lC6Hl3 E2-7 甘 ~JOr 1 -o- ~JSJT^JT αΝΌ E2-8 ~^cy~ 1 -o- <xy αΝΌ E2-9 1 —0 ~ αΝο E2-10 <P〇r -o- -J\)r^jr 0¾ 60 200906909 【表33】例示化合物編號 V Ar\ Ar3 n, m T1,T2 ArS, Ar4 E2-11 1 -o- 〇rNO E2-12 -0^0- ~o~ 1 -〇- -oo- 0¾ E2-13 1 -o- 〇rN€) E2-14 ch3 ch3 1 -o- αΝΌ E2-15 h3c ch3 1 -o- σΝΌ E2-16 -〇 1 -o- αΝΌ E2-1 7 C«H,3,CRHn 1 —〇- αΝΌ E2-18 CeH!? CbH17 ''Φ〇Γ ~Qir 1 -o- 〇ΓΝΌ Ε2Ί9 OS> mx -Or 1 -o~ αΝο E2-20 〇S> ~o~ 1 -o- 〇ΓΝι〇 E2-21 tr ~^y~ -o - -oo σΝΌ E2-22 ji/a ~Qir —〇 _ αΝΌ E2-23 ~JOr -〇_ σΝΌ E2-24 Me2 JDrSixx ~o~ -o- ~^y^y~ αΝο 61 200906909 【表34】 ί 例示化合物編號 Υ Ar1, Ar3 n, m t\t2 Ar2, Ar4 V ,X4 〜 Ε3-1 1 -o - H^= ch3 C"O Ε3-2 ~Qt~ 1 -o- Hf CH, (7¾ Ε3-3 d-p ~^jr 1 -o- CH3 〇τΝΌ Ε3-4 1 -o- ^o~ 〇τΝΌ Ε3-5 ~JOr 1 -o- CHj ~<>o~ 0¾ Ε3-6 ~J〇}~ 1 -o- ΗίνεΗ, Ε3-7 曾 ~Qir 1 -o- W CH3 αΝΌ Ε3-8 Or -o- Ηβ CH, αΝΌ Ε3-9 -o- Hfi CH3 αΝο Ε3-10 ~<Ρ〇Γ ~~o~ -〇- CH3 ~^Όγ σΝΌ 62 200906909 【表35】Exemplary compound number Y Ar1, Ar3 n, m T'T2 Ar2, Ar4·V, eight E2-1 1 -o - σΝΌ E2-2 1 -o - 03⁄4 E2-3 1 -o- ~G^O~ 〇τΝΌ E2-4 ^JT 1 -o- σΝΌ E2-5 1 -o- αΝΌ E2-6 ~^JT 1 -o- CeH,^N€lC6Hl3 E2-7 Gan~JOr 1 -o- ~JSJT^JT αΝΌ E2 -8 ~^cy~ 1 -o- <xy αΝΌ E2-9 1 —0 ~ αΝο E2-10 <P〇r -o- -J\)r^jr 03⁄4 60 200906909 [Table 33] Example compound number V Ar\ Ar3 n, m T1, T2 ArS, Ar4 E2-11 1 -o- 〇rNO E2-12 -0^0- ~o~ 1 -〇- -oo- 03⁄4 E2-13 1 -o- 〇rN €) E2-14 ch3 ch3 1 -o- αΝΌ E2-15 h3c ch3 1 -o- σΝΌ E2-16 -〇1 -o- αΝΌ E2-1 7 C«H,3,CRHn 1 —〇- αΝΌ E2- 18 CeH!? CbH17 ''Φ〇Γ ~Qir 1 -o- 〇ΓΝΌ Ε2Ί9 OS> mx -Or 1 -o~ αΝο E2-20 〇S> ~o~ 1 -o- 〇ΓΝι〇E2-21 tr ~ ^y~ -o - -oo σΝΌ E2-22 ji/a ~Qir —〇_ αΝΌ E2-23 ~JOr -〇_ σΝΌ E2-24 Me2 JDrSixx ~o~ -o- ~^y^y~ αΝο 61 200906909 [Table 34] ί Illustrative compound number Υ Ar1, Ar3 n, mt\t2 Ar2, Ar4 V , X4 ～ Ε 3-1 1 -o - H^= ch3 C"O Ε3-2 ~Qt~ 1 -o- Hf CH, (73⁄4 Ε3-3 dp ~^jr 1 -o- CH3 〇τΝΌ Ε3-4 1 -o- ^o~ 〇τΝΌ Ε3-5 ~JOr 1 -o- CHj ~<>o~ 03⁄4 Ε3-6 ~J〇}~ 1 -o- ΗίνεΗ, Ε3-7 曾~Qir 1 -o- W CH3 αΝΌ Ε3-8 Or -o- Ηβ CH, αΝΌ Ε3-9 -o- Hfi CH3 αΝο Ε3-10 ~<Ρ〇Γ ~~o~ -〇- CH3 ~^Όγ σΝΌ 62 200906909 [Table 35]

63 200906909 【表36】63 200906909 [Table 36]

例示化合物編號 Y Ar1, Ar3 n, m t\t2 Ar2, Ar4 Wv F1-1 XX ^lr 1 -o- ~Qt~ 〇ώ〇 F1-2 ~^\jT 1 -〇 - ~^\jT 〇ώ〇 F1-3 1 〇ώ〇 F1-4 <y 1 -o- *O~ 〇ώ〇 F1-5 1 -o - ~o~ 〇ώ〇 F1-6 甘 ~o~ 1 -o- ~^]r 0¾ F1-7 -o- ~^cy~ 0¾ F1-8 ~~^JT -o- <y 〇ώ〇 F1-9 ~^S-Qr ~JOr 1 -o- 0¾ F1-10 ~^)r 1 ^)r 〇ώ〇 64 200906909 【表37】例示化合物編號 Y Ar1, Ar3 n, m T'T2 Ar2, Ar4 v，八 F1-1 1 OOr ~o~ 1 -o- 〇ώ〇 F1-12 1 -o- 0¾ F1 -13 ch3 ~o~ 1 -o- ~ζ)τ ‘ 〇ώ〇 F1-14 ~^]r 1 -o- ~^)r 〇ώ〇 F1-15 ~J^JT 1 -o- ~^Qt~ 0¾ F1-16 CeH13 CeH13 ~JOr 1 -o- ~Qir 〇ώ〇 F1-17 ◦8Η1ζ^ΑΗ17 ~Qir 1 -o- ^JT 0¾ F1 -1 8 〇s> ~JOr 1 -〇- ~Qir 0¾ F1-19 xrsKa ~^JT 1 -o- ~^JT 0¾ F1-20 tr 1 -o- ~〇JT 0¾ F1-21 i/ia ~Jv)r 1 -o- ~Qir 0¾ F1-22 ~o~ -o- 0¾ F1 -23 Me^ jaSixx ~JOr -o- ~o~ 0¾ 65 200906909 【表38】Exemplary compound number Y Ar1, Ar3 n, mt\t2 Ar2, Ar4 Wv F1-1 XX ^lr 1 -o- ~Qt~ 〇ώ〇F1-2 ~^\jT 1 -〇- ~^\jT 〇ώ〇 F1-3 1 〇ώ〇F1-4 <y 1 -o- *O~ 〇ώ〇F1-5 1 -o - ~o~ 〇ώ〇F1-6 甘~o~ 1 -o- ~^] r 03⁄4 F1-7 -o- ~^cy~ 03⁄4 F1-8 ~~^JT -o- <y 〇ώ〇F1-9 ~^S-Qr ~JOr 1 -o- 03⁄4 F1-10 ~^) r 1 ^)r 〇ώ〇64 200906909 [Table 37] Exemplary compound numbers Y Ar1, Ar3 n, m T'T2 Ar2, Ar4 v, eight F1-1 1 OOr ~o~ 1 -o- 〇ώ〇F1- 12 1 -o- 03⁄4 F1 -13 ch3 ~o~ 1 -o- ~ζ)τ ' 〇ώ〇F1-14 ~^]r 1 -o- ~^)r 〇ώ〇F1-15 ~J^JT 1 -o- ~^Qt~ 03⁄4 F1-16 CeH13 CeH13 ~JOr 1 -o- ~Qir 〇ώ〇F1-17 ◦8Η1ζ^ΑΗ17 ~Qir 1 -o- ^JT 03⁄4 F1 -1 8 〇s> ~JOr 1 -〇- ~Qir 03⁄4 F1-19 xrsKa ~^JT 1 -o- ~^JT 03⁄4 F1-20 tr 1 -o- ~〇JT 03⁄4 F1-21 i/ia ~Jv)r 1 -o- ~Qir 03⁄4 F1-22 ~o~ -o- 03⁄4 F1 -23 Me^ jaSixx ~JOr -o- ~o~ 03⁄4 65 200906909 [Table 38]

例示化合物編號 Y Ar\ Ar3 n, m T'T2 Ar2, Ar4 v .八 F2-1 XX Ό~ 1 -o- 〇ώ〇 F2-2 ~o~ 1 -o- 〇ώ〇 F2-3 1 -〇- 〇ώ〇 F2-4 -8- ~Qr 1 -o - 0¾ F2-5 1 -o- 0¾ F2-6 曾 ~Qir 1 -o- 0¾ F2-7 ~Ότ 1 -o- 0¾ F2-8 ~J^)r -o- 〇ώ〇 F2-9 ~€p〇r ~^JT -o- 0¾ F2-10 Or -o- 0¾ 66 200906909 【表39】例示化合物編號 Y Ar\ Ar3 n, m T'T2 Ar2, Ar4 V . F2-1 1 普分 1 -〇- 0¾ F2-1 2 典 ~^]r 1 -〇— -^irOr 〇ώ〇 F2-13 ch3 ch3 1 -o- -^y^ur 0¾ F2-14 h3c ch3 "oxy ~JOr -o- -ζ)τ〇Γ 〇ώ〇 F2-1 5 jcftx 1 -o- 〇ώ〇 F2-16 -oS- 1 -o- 0¾ F2-17 ^CH> -o- 〇ώ〇 F2-1 8 〇S> 0ΧΧ <JT -Qr^r 0¾ F2-19 xr^a ^JT -o- 0¾ F2-20 tr ~^JT 1 -o- 0¾ F2-21 j〇\x 1 -o- 〇ώ〇 F2-22 ja'tx 1 -o- 0¾ F2-23 Me2 jas,xx ~JOr 1 -o- -J%urJ\jr 0¾ 67 200906909 【表40】 :/ 例示化合物編號 Y Ar1, Ar3 n, m t\t2 Ar2, Ar4 V ,，X3 F3-1 1 -o- ch3 〇ώ〇 FS-2 b-q 1 -o- HVH3 0¾ F3-3 1 MaC CH3 C*〇 F3-4 1 -〇- HjC CH3 〇ώ〇 F3-5 ^JT 1 -o- CH3 0¾ F3-6 言 ~^)r 1 -〇一 W ch3 ~O~(y 0¾ F3-7 ~ΟίΓ -o- CH3 ~Ό-0~ 0¾ F3-8 -o- CH3 0¾ F3-9 ~^P〇r ^]r 1 -o- CH3 〇ώ〇 F3-10 -^Qr ~Q]r 1 -o - Ch3 〇ώ〇Illustrative compound number Y Ar\ Ar3 n, m T'T2 Ar2, Ar4 v . eight F2-1 XX Ό~ 1 -o- 〇ώ〇F2-2 ~o~ 1 -o- 〇ώ〇F2-3 1 - 〇- 〇ώ〇F2-4 -8- ~Qr 1 -o - 03⁄4 F2-5 1 -o- 03⁄4 F2-6 Zeng ~Qir 1 -o- 03⁄4 F2-7 ~Ότ 1 -o- 03⁄4 F2-8 ~J^)r -o- 〇ώ〇F2-9 ~€p〇r ~^JT -o- 03⁄4 F2-10 Or -o- 03⁄4 66 200906909 [Table 39] Illustrative compound number Y Ar\ Ar3 n, m T'T2 Ar2, Ar4 V . F2-1 1 General 1 -〇- 03⁄4 F2-1 2 典~^]r 1 -〇— -^irOr 〇ώ〇F2-13 ch3 ch3 1 -o- -^y ^ur 03⁄4 F2-14 h3c ch3 "oxy ~JOr -o- -ζ)τ〇Γ 〇ώ〇F2-1 5 jcftx 1 -o- 〇ώ〇F2-16 -oS- 1 -o- 03⁄4 F2- 17 ^CH> -o- 〇ώ〇F2-1 8 〇S> 0ΧΧ <JT -Qr^r 03⁄4 F2-19 xr^a ^JT -o- 03⁄4 F2-20 tr ~^JT 1 -o- 03⁄4 F2-21 j〇\x 1 -o- 〇ώ〇F2-22 ja'tx 1 -o- 03⁄4 F2-23 Me2 jas,xx ~JOr 1 -o- -J%urJ\jr 03⁄4 67 200906909 [Table 40 】 :/ Illustrated compound number Y Ar1, Ar3 n, mt\t2 Ar2, Ar4 V ,, X3 F3-1 1 -o- ch3 〇ώ〇FS-2 bq 1 -o- HVH3 03⁄4 F3-3 1 MaC CH3 C *〇F3-4 1 -〇- HjC CH3 〇ώ〇F3-5 ^JT 1 -o- CH3 03⁄4 F3-6 言~^)r 1 -〇一W ch3 ~O~(y 03⁄4 F3-7 ~ΟίΓ -o- CH3 ~Ό-0~ 03⁄4 F3-8 -o- CH3 03⁄4 F3-9 ~^P〇r ^]r 1 -o- CH3 〇ώ〇F3-10 -^Qr ~Q]r 1 -o - Ch3 〇ώ〇

6S 200906909 【表41】例示化合物編號 Y Ar\ Ar3 n, m t\t2 Ar2, Ar4 F3-1 1 -〇-s-〇- ~J^r 1 -o- HP ch3 〇ώ〇 F3-1 2 分ch3 《％ 'JYJT 1 CH3 ^Qr 0¾ F3-13 ch3 040- ch3 ~Qir 1 -o - ch3 -〇V 0¾ FG-14 h3c ch3 ~JOr 1 -o — CH3 -〇5> 0¾ F3-1 5 j〇Ra ~^JT 1 -o- W CH3 ~Φ> 0¾ F3-16 CeH 13 1 -〇一 H/： CH, -o-o- 〇ώ〇 F3-1 7 CeHu -o- HtC cm. 0¾ F3-1 8 CK> mx ~Qir -o- hVH3 <^Qr 〇ώ〇 F3-1 9 5P xrsXa -o- HjC CH3 -W> 〇ώ〇 F3-20 tr ~^y~ 1 -0' 0¾ F3-21 i/a 1 -o~ H^C CH3 〇ώ〇 F3-22 /Ax ~~Qr 1 -0' Ch3 〇ώ〇 F3-23 Me^ 1 -0' CHj 〇ώ〇 69 200906909 【表42】 f6S 200906909 [Table 41] Exemplary compound number Y Ar\ Ar3 n, mt\t2 Ar2, Ar4 F3-1 1 -〇-s-〇- ~J^r 1 -o- HP ch3 〇ώ〇F3-1 2 points Ch3 "% 'JYJT 1 CH3 ^Qr 03⁄4 F3-13 ch3 040- ch3 ~Qir 1 -o - ch3 -〇V 03⁄4 FG-14 h3c ch3 ~JOr 1 -o — CH3 -〇5> 03⁄4 F3-1 5 j 〇Ra ~^JT 1 -o- W CH3 ~Φ> 03⁄4 F3-16 CeH 13 1 -〇一H/: CH, -oo- 〇ώ〇F3-1 7 CeHu -o- HtC cm. 03⁄4 F3-1 8 CK> mx ~Qir -o- hVH3 <^Qr 〇ώ〇F3-1 9 5P xrsXa -o- HjC CH3 -W> 〇ώ〇F3-20 tr ~^y~ 1 -0' 03⁄4 F3-21 i/a 1 -o~ H^C CH3 〇ώ〇F3-22 /Ax ~~Qr 1 -0' Ch3 〇ώ〇F3-23 Me^ 1 -0' CHj 〇ώ〇69 200906909 [Table 42] f

例示化合物編號 Y Ar’，Ar3 π, m τ1, τ2 Ar2, Ar4 (31-1 1 -s- σΝυ GT-2 1 -(CH2)5- ~o~ σΝΌ G1-3 1 -(CH2)6- ~Qir αΝΌ G1-4 ~O~ 1 -(CH2)8_ ~^JT σΝυ G1-5 ~ΟίΓ 1 _c=c- -^Qjt 〇τΝΌ G1-6 ~〇~ -c= c- ~^jt αΝυ G1-7 ~ίΏτ H3 乂 h3 ~^JT σΝΌ G1-8 ~ίΏτ 2 h3c ch3 σΝΌ G1-9 ^XJT 1 Q 0¾ (31-10 ~o~ ~Ό~ 1 qp ~^JT αΝο 70 200906909 【表43】例示化合物編號 Y Ar\ Ar3 π, m τ\τ2 Ar2, Ar4 V . Λ 31-1 1 ~JOr 1 Op ~o~ σΝΌ G1-12 ~J^)r 1 -co- σΝΌ G1-13 ~J^JT 1 -so- σΝΌ (31 -1 4 -S02- "^\JT 0¾ G1-15 -SiH2- σΝΌ <31-16 ~JOr -SiMe2- ~^JT αΝυExemplary compound number Y Ar', Ar3 π, m τ1, τ2 Ar2, Ar4 (31-1 1 -s- σΝυ GT-2 1 -(CH2)5- ~o~ σΝΌ G1-3 1 -(CH2)6- ~Qir αΝΌ G1-4 ~O~ 1 -(CH2)8_ ~^JT σΝυ G1-5 ~ΟίΓ 1 _c=c- -^Qjt 〇τΝΌ G1-6 ~〇~ -c= c- ~^jt αΝυ G1 -7 ~ίΏτ H3 乂h3 ~^JT σΝΌ G1-8 ~ίΏτ 2 h3c ch3 σΝΌ G1-9 ^XJT 1 Q 03⁄4 (31-10 ~o~ ~Ό~ 1 qp ~^JT αΝο 70 200906909 [Table 43] Exemplary compound number Y Ar\ Ar3 π, m τ\τ2 Ar2, Ar4 V . Λ 31-1 1 ~JOr 1 Op ~o~ σΝΌ G1-12 ~J^)r 1 -co- σΝΌ G1-13 ~J^ JT 1 -so- σΝΌ (31 -1 4 -S02- "^\JT 03⁄4 G1-15 -SiH2- σΝΌ <31-16 ~JOr -SiMe2- ~^JT αΝυ

71 200906909 【表44】71 200906909 [Table 44]

例示化合物編號 Y Ar1, Ar3 π, m τ\τ2 Ar2, Ar4 V .八 G2-1 ~ο~ 1 -s- 0¾ G2-2 1 -(CH2)5- 0¾ G2-3 1 -(CH2)6- ~l%yj\jr αΝυ G2-4 "〇~ 1 -(CH2) 8- σΝυ G2-5 -〇 1 -c= c- ~J\JT〇r αΝΌ G2-6 1 -c= c- 咖 G2-7 ~ίΌτ H3^H3 -^jrQjr αΝυ G2-8 Ό- Q -^yjrQir σΝΌ G2-9 1 qp σΝΌ G2-10 〇 -〇 1 ~^%y~Qjr αΝΌ 72 200906909 【表45】Illustrative compound number Y Ar1, Ar3 π, m τ\τ2 Ar2, Ar4 V .8 G2-1 ~ο~ 1 -s- 03⁄4 G2-2 1 -(CH2)5- 03⁄4 G2-3 1 -(CH2)6 - ~l%yj\jr αΝυ G2-4 "〇~ 1 -(CH2) 8- σΝυ G2-5 -〇1 -c= c- ~J\JT〇r αΝΌ G2-6 1 -c= c- Coffee G2-7 ~ίΌτ H3^H3 -^jrQjr αΝυ G2-8 Ό- Q -^yjrQir σΝΌ G2-9 1 qp σΝΌ G2-10 〇-〇1 ~^%y~Qjr αΝΌ 72 200906909 [Table 45]

73 200906909 【表46】乂. 例示化合物編號 Y Ar\ Ar3 π, m τ'τ2 Ar2, Ar4 V .八 G3-1 1 _ε- hjc ch3 σΝΌ GG-2 1 -(CH2)5- h3c ch3 ^〇r σΝτ〇 G3-3 1 -(CH2)6- H^C CH3 σΝΌ G3-4 1 -(CH2)8- 叹 CH3 σΝΌ G3-5 -Ο- 1 -c= c- H3C CH3 -W> σΝΌ G3-6 ~J^JT 1 -c= c- H3C CH, σΝΌ G3-7 η3^ρη3 H,C CHj ~Φ> σΝΌ G3-8 Ό- 1 Q CH3 <P〇r σΝν G3-9 -ο ~^)Γ 1 qp h3c ch3 σΝΌ G3-10 ~JOr 1 o^P> h3c ch3 ^5> σΝΌ 74 200906909 【表47】例示化合物編號 Y Ar1, Ar3 n, m T'T2 Ar2, Ar4 G3-1 1 1 -co- h3c ch3 ~Φ> σΝο G3-1 2 ~J^JT 1 _s〇_ H3C CH3 -〇5> 0¾ G3-1G 1 -S02- H3C Ch3 αΝΌ G3-14 ^y~ -SiH2- H；jC CH3 0¾ *33-15 -SiMe2- HgC CH3 σΝΌ73 200906909 [Table 46] 乂. Exemplary compound number Y Ar\ Ar3 π, m τ'τ2 Ar2, Ar4 V . Eight G3-1 1 _ε- hjc ch3 σΝΌ GG-2 1 -(CH2)5- h3c ch3 ^〇 r σΝτ〇G3-3 1 -(CH2)6- H^C CH3 σΝΌ G3-4 1 -(CH2)8- CHCH3 σΝΌ G3-5 -Ο- 1 -c= c- H3C CH3 -W> σΝΌ G3 -6 ~J^JT 1 -c= c- H3C CH, σΝΌ G3-7 η3^ρη3 H,C CHj ~Φ> σΝΌ G3-8 Ό- 1 Q CH3 <P〇r σΝν G3-9 -ο ~ ^)Γ1 qp h3c ch3 σΝΌ G3-10 ~JOr 1 o^P> h3c ch3 ^5> σΝΌ 74 200906909 [Table 47] Exemplary compound number Y Ar1, Ar3 n, m T'T2 Ar2, Ar4 G3-1 1 1 -co- h3c ch3 ~Φ> σΝο G3-1 2 ~J^JT 1 _s〇_ H3C CH3 -〇5> 03⁄4 G3-1G 1 -S02- H3C Ch3 αΝΌ G3-14 ^y~ -SiH2- H; jC CH3 03⁄4 *33-15 -SiMe2- HgC CH3 σΝΌ

75 200906909 【表48】、\75 200906909 [Table 48], \

例示化合物編號 Y Ar\ Ar3 n, m T\T2 Ar2, Ar4 νΆ . H1-1 ~JOr 1 ~ s - 〇ώ〇 H1-2 1 -(CH2)5- ~ζ)τ 0¾ H1-3 1 -(CH2)6- Ό~ 0¾ Η1-4 ~J\y~ ^JT 1 -(CH2)8- C*〇 ΗΤ-5 ~Qlr 1 -c=c- ~Qlr 〇ώ〇 Η1-6 -c= c- ~Qr 0¾ H1 -7 ~o~ h3c>ch3 0¾ Hl-8 ~Qr ~J^)r 2 h3 父 h3 0¾ H1-9 1 Q ~o~ 0¾ H1-10 ~^JT 1 qp 0¾ 76 200906909 【表49】 f \Exemplary compound number Y Ar\ Ar3 n, m T\T2 Ar2, Ar4 νΆ . H1-1 ~JOr 1 ~ s - 〇ώ〇H1-2 1 -(CH2)5- ~ζ)τ 03⁄4 H1-3 1 - (CH2)6- Ό~ 03⁄4 Η1-4 ~J\y~ ^JT 1 -(CH2)8- C*〇ΗΤ-5 ~Qlr 1 -c=c- ~Qlr 〇ώ〇Η1-6 -c= C- ~Qr 03⁄4 H1 -7 ~o~ h3c>ch3 03⁄4 Hl-8 ~Qr ~J^)r 2 h3 Parent h3 03⁄4 H1-9 1 Q ~o~ 03⁄4 H1-10 ~^JT 1 qp 03⁄4 76 200906909 [Table 49] f \

例示化合物編號 Υ Ar\ Ar3 n, m τ'丁2 Ar2, Ar4 Η 1-1 1 ~^)r 1 qp ~o~ 0¾ Η1-12 ~^ζ)τ 1 -co- 0¾ Η1 -13 ~^JT 1 -so- ~^JT 〇ώ〇 Η1-14 ~J^JT -S02- ^JT 0¾ Η 1-1 5 ~^y~ -SiH2- ^JT 0¾ Η1-16 ~JOr -SiM«2- ^JT 0¾ 77 200906909 【表50】例示化合物編號 Υ Ar\ Ar3 n, m T'T2 Ar2, Ar4 V . X? V H2-1 1 -s- 0¾ H2-2 1 -(CH2)5- 0¾ H2-3 1 -(CH2)6- ~^)rQ]r 〇ώ〇 H2-4 ό~ 1 -(CH2)8- -Q]r^y- 〇ώ〇 H2-5 1 -c=c- ~0~Ό~ 0¾ H2-6 ~o~ 1 _ CH C- 0¾ H2-7 η3^οη3 -^y-^ur 0¾ H2-8 ^JT Q 0¾ Η 2-9 ~I\JT 1 qp 0¾ Η2-10 1 qp 0¾ 78 200906909 【表51】例示化合物編號 Y Ar\ Ar3 n, m t\t2 Ar2, Ar4 χνΆ H2-1 1 ~J\JT 1 -co- 0¾ H2-T 2 -Or 1 -so- -^UT^JT C*〇 H2-13 1 -S02- 0¾ H2-14 'J^}~ -SiH2- 0¾ H2-15 ~o~ -SiMe2- 〇ώ〇Illustrative compound number Υ Ar\ Ar3 n, m τ'丁2 Ar2, Ar4 Η 1-1 1 ~^)r 1 qp ~o~ 03⁄4 Η1-12 ~^ζ)τ 1 -co- 03⁄4 Η1 -13 ~^ JT 1 -so- ~^JT 〇ώ〇Η1-14 ~J^JT -S02- ^JT 03⁄4 Η 1-1 5 ~^y~ -SiH2- ^JT 03⁄4 Η1-16 ~JOr -SiM«2- ^ JT 03⁄4 77 200906909 [Table 50] Exemplary compound number Υ Ar\ Ar3 n, m T'T2 Ar2, Ar4 V . X? V H2-1 1 -s- 03⁄4 H2-2 1 -(CH2)5- 03⁄4 H2- 3 1 -(CH2)6- ~^)rQ]r 〇ώ〇H2-4 ό~ 1 -(CH2)8- -Q]r^y- 〇ώ〇H2-5 1 -c=c- ~0 ~Ό~ 03⁄4 H2-6 ~o~ 1 _ CH C- 03⁄4 H2-7 η3^οη3 -^y-^ur 03⁄4 H2-8 ^JT Q 03⁄4 Η 2-9 ~I\JT 1 qp 03⁄4 Η2-10 1 qp 03⁄4 78 200906909 [Table 51] Exemplary compound number Y Ar\ Ar3 n, mt\t2 Ar2, Ar4 χνΆ H2-1 1 ~J\JT 1 -co- 03⁄4 H2-T 2 -Or 1 -so- -^ UT^JT C*〇H2-13 1 -S02- 03⁄4 H2-14 'J^}~ -SiH2- 03⁄4 H2-15 ~o~ -SiMe2- 〇ώ〇

79 200906909 【表52】例示化合物編號 Y Ar\ Ar3 n, m τ\τ2 Ar2, Ar4 H3-1 1 -s~ HaCvCH;> 〇ώ〇 H3-2 Ο- 1 -(CH2)5- H,C CH, 0¾ H3-3 1 _ (CH2)6_ H3c ch3 ~0-O~ 〇ώ〇 H3-4 '^JT ~^JT 1 -(CH2)8- H3C 0¾ H3-5 ~Οίϊ~ 1 -c= c- h3c ch3 0¾ H3-6 -c= c- h3c ch3 ^Qr 0¾ H3-7 ^jT ^YJT H父H3 CH，〇ώ〇 H3-8 ~^〇Γ Q HaC CH, 0¾ H3-9 1 qp h3c ch3 ^Q~ 〇ώ〇 H3-1 0 1 h3C Ch3 Ό-λ>· 0¾ 80 200906909 【表53】例示化合物編號 Y Ar1, Ar3 n, m T\T2 Ar2, Ard H3-1 1 1 -co- h3c ch3 0¾ H3-1 2 ^JT 1 -so_ 0¾ H3-13 _ηΟ_ 1 -S02- hjC ch3 0¾ H3-1 4 ~JOr -SiH2- h3c ch3 ^>Λ>· 0¾ H3-1 5 -O' -SiMe2_ H3c ^pH3 -^-Or 0¾ 其次，說明本發明對於高分子鏈中具有通式(1)所示重複單位至少1個之高分子化合物中導入有磺基之化合物之製造方法。為原料之在高分子鏈中具有通式(1)所示重複單位至少1個之高分子化合物，例如通式(3): \ Η / ν ^χ3 ^N-hAr2—T14-Ar1—Ν—Y—N~Ar3f T2—(3) X2 ^ Η η X4 (式中，X1〜X4、Ar1〜Ar4、Τ1、Τ2、Υ及m、η如通式⑴。）所示化合物與通式(4):79 200906909 [Table 52] Illustrative compound number Y Ar\ Ar3 n, m τ\τ2 Ar2, Ar4 H3-1 1 -s~ HaCvCH;> 〇ώ〇H3-2 Ο-1 -(CH2)5-H, C CH, 03⁄4 H3-3 1 _ (CH2)6_ H3c ch3 ~0-O~ 〇ώ〇H3-4 '^JT ~^JT 1 -(CH2)8- H3C 03⁄4 H3-5 ~Οίϊ~ 1 -c = c- h3c ch3 03⁄4 H3-6 -c= c- h3c ch3 ^Qr 03⁄4 H3-7 ^jT ^YJT H Parent H3 CH, 〇ώ〇H3-8 ~^〇Γ Q HaC CH, 03⁄4 H3-9 1 Qp h3c ch3 ^Q~ 〇ώ〇H3-1 0 1 h3C Ch3 Ό-λ>· 03⁄4 80 200906909 [Table 53] Exemplary compound numbers Y Ar1, Ar3 n, m T\T2 Ar2, Ard H3-1 1 1 - Co- h3c ch3 03⁄4 H3-1 2 ^JT 1 -so_ 03⁄4 H3-13 _ηΟ_ 1 -S02- hjC ch3 03⁄4 H3-1 4 ~JOr -SiH2- h3c ch3 ^>Λ>· 03⁄4 H3-1 5 -O '-SiMe2_H3c^pH3 -^-Or 03⁄4 Next, a method for producing a compound having a sulfo group introduced into a polymer compound having at least one repeating unit represented by the formula (1) in the polymer chain of the present invention will be described. A polymer compound having at least one repeating unit represented by the formula (1) in a polymer chain as a raw material, for example, the formula (3): \ Η / ν ^ χ 3 ^ N-hAr2 - T14-Ar1 - Ν - Y—N~Ar3f T2—(3) X2 ^ Η η X4 (wherein, X1 to X4, Ar1 to Ar4, Τ1, Τ2, Υ, and m, η are represented by the formula (1).) The compound and the formula (4) ):

(式中，X表示鹵素原子，Ζ1〜Ζ'ρ1〜ρ4同前述。）所示化合物，於驗存在下，藉由以Pd觸媒等使聚合以製造。 81 200906909 X之A素原子之例，例如:氣原子、氯原子、溪原子本發明之含有磺基之高分子化合物，八；、，子。以如通式⑴所示重複單位至少1個之高分子化石黃化使用之石黃化劍，^ Γ u 氧不石頁化使用之石黃化劑，例如硫酸、發煙硫酸、三氧、：物、氯硫酸、氟硫酸、醯胺硫酸等，使用之碭“ Ϊ.「人物三合物’為_、胺類、硫化物類等路易士酸之許合物，例如:Ν，Ν—二甲基甲醯胺•二势士自夂之錯氧化硫錯合物、対·：氧化^辑;^化硫錯5物、二吟燒•三合物、三伽.三氧二=物、三乙基胺氧化硫錯與塑溶劑或溶劑中進行。反應使用之溶劑，。要是不二氯乙炫、四氯乙龄減麵二%、四氯化碳、 ^苯=甲ί 乙〒類V工、、四氫咬味、二气垸、二甲基^三^、乙腈、 -咪^糊、N—甲基轉。—甲基乙_、Μ —二甲基成磺醯氣，並將其水解而得。蚪。又，亦可藉由氯硫酸合應溶劑&出之子方法不特別限制。於產物從反應溶劑之情形，^4 2心分離而單離，於溶解在反劑使析出，再渡去溶劑之方法或添加適當溶除去：形鹽^形’可於過遠後進行水洗，藉此脂等。了使崎金屬、驗土類金屬等之氫氧化物或離子交換樹 82 200906909 ==吸附處理：=^、、^沉透析膜、逆滲透膜、超過據膜等處理方财又換膜說明本發明之有機電場發光材料。式⑴所======高分子鍵中具有通 ί作ί 件巾使狀電酿才子化t物致發光元件㈣’可於將本剌之高分發明之高分子化合物予以單直接使用’也可將本 -丁酉旨、乙酸戊酉旨、乳酸乙_旨溶=乙酸乙醋、乙酸，溶劑;二丁趟、四氯咬喃、n ·^二=醇 ==，N3rn，r 甲等。此等溶劑之中，以極性溶劑較佳亞解極性溶劑 s:可於其上之繼對於甲苯等煙系溶劑== 其次，說明本發明之有機電致發光元件。本發明之有機電致發光元件，係在i f/電極之間，夹持含有 83 200906909 電極之間，夾。有機電致發光元件，通常係於1對可考量發光層使^之化二種f光成分之發光層至少丨層而成。電子輸送之各功能水平洞輸送、電子注入及例如吏用ί電子注入輪送層。 =〜功能、電子輪：二：可電將== Γ 情形，可為在發光層陰極側設^子輪送功能之層夾住之構成的3 ％雛人輪送層及電子注入輸送(wherein, X represents a halogen atom, and Ζ1 to Ζ'ρ1 to ρ4 are the same as defined above.) The compound shown is produced by polymerization using a Pd catalyst or the like in the presence of the test. 81 200906909 Examples of the A atom of X, for example, a gas atom, a chlorine atom, a stream atom, a polymer compound containing a sulfo group of the present invention, VIII; A stone yellowing agent used for the polymerized stone yellowing of at least one unit of the repeating unit as shown in the general formula (1), and a stone yellowing agent such as sulfuric acid, fuming sulfuric acid, trioxane, or the like , chlorosulfuric acid, fluorosulfuric acid, decylamine sulphuric acid, etc., used in the "Ϊ. "Characteristic triads" are _, amines, sulfides and other Lewis compounds such as bismuth, bismuth-dimethyl醯醯 • • 二二 • • • • • • 氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化氧化The ethylamine oxidized sulfur is reacted with a solvent or a solvent. The solvent used in the reaction, if not dichloroethylene, tetrachloroethyl age minus 2%, carbon tetrachloride, ^benzene = methyl acetamidine V Work, tetrahydrobite, dioxane, dimethyl^3, acetonitrile, -methane, N-methyltrans.-methylethyl _, hydrazine-dimethyl sulfonate, and The method of hydrolyzing is also not particularly limited. The product is separated from the reaction solvent by the reaction solvent, and is dissolved in the anti-agent. Precipitation, further removal of the solvent or addition of appropriate dissolution: the shape of the salt can be washed away after too long, thereby using lipids, etc.. The hydroxide or ion exchange tree of the metal, soil, etc. 82 200906909 ==Adsorption treatment: =^,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, In the key, there is a ί 作使使使使 t t t t t t 物物物物物物物物物物物物物物物物物物物物物物物物物物物物物物物物物物物物物酉、, lactic acid B _ _ solution = acetic acid vinegar, acetic acid, solvent; dibutyl hydrazine, tetrachlorine, n · ^ two = alcohol ==, N3rn, r A, etc. Among these solvents, with polar solvents Preferred sub-polar solvent s: may be followed by a solvent for toluene such as toluene == Next, the organic electroluminescent device of the present invention will be described. The organic electroluminescent device of the present invention is between if/electrodes , clamped between 83 200906909 electrodes, clips. Organic electroluminescent elements, usually tied to 1 pair Considering the luminescent layer, the luminescent layer of the two kinds of f-light components is at least 丨 layered. The function of the electron transport is horizontal hole transport, electron injection and, for example, 电子 electron injection into the wheel layer. 2: It can be electric == Γ In case, it can be a 3 % chick transfer layer and electron injection transport which is formed by sandwiching the layer of the wheel on the cathode side of the light-emitting layer.

L 單層構造:: ί:ϊ入j送層及發光層各層，可為可以在層中，送収電子私輸送層，本發明之有播此之層及具輸送功能之層。或其中間體高分中以;^月2^基之高分子本發明之有機ΐ;發巧輸送層更佳。化合物或其中間體高分子化中可H月^含，石黃基之高分子本發明有機電致發光元件之播I早獨使用，亦可併用多數。. 極/電洞注入輸送層/發光層成，別限制’例如(EL-1)陽 (EL—2)陽極/電洞注入輪^，丄入輸达層/陰極型元件(圖1}、陽極/發光層/電子注入钤送^光層7陰極型元件(圖2)、（EL —3) 光層/陰極型元件(圖“H兀件(圖3)、（EL-4)陽極/發者’可為將發光層4以電洞注入輸送 84 200906909 ^層夾入方式，製成風一5)陽極2/電洞注入元件(圖m @ ^子注入輪送層5/陰極6型光層而言，將發光者巧成狐―4)類型之元件，就發元修-6) 型的分4a及電子注A 士八<A ^ 入輸运成分3a、發光成之類型的元件(圖6);广形態’夾持於1對電極間分如及發光Z 層而言，使物主入輸送成的元件(圖7);(EL-8):上^形，，失持於1對電極間之類型成分5a混合之…开/^ 而言’使發光成分4a及電子注人 •又，電洞注入^ =，,夫持於1對電極間之類型的元件(圖8)。注入輸送層至少’可具含有本發明高分子化合物之電洞態4?明ί；多機不限於該等元件構成，在各型間’心S㈡=^子注·層之型元件、（EL-5)¾^牛光3構成，為(EL —υ型元件、（EL —2) 為狐-!)型元件牛;型元件或風―7)型元件，更佳件。件姐―2)型兀件、忸-5)型猶或(EL —7)型元以下發陽勵注入輸送層/ 致發光元件之構成要素，詳細説明 I型元件圖1中，1表示基板、2夺千^ 一表示發光層、5表示電子:主#^極、3表7^電洞注人輸送層、4 本發明之麵紐層、6表示陰極、7表示電源。 .坡璃等玻軌聚S旨、聚碳特別限制，以透明至半m支持於基板1較佳，基板則不矽酸鹽玻璃耸诂掠& 土板較佳，材質可使用鈉鈣玻璃、硼酸酯、聚砜、聚醚砜、聚丙烯酸 200906909 酯、聚甲基丙烯酸甲酯、平可使用半透龍膠片材、絲=烯等透·高分子。又，材所構成之基板。再者，可於趣將此等組合之複合片換膜、介電體反射臈，而控制=色。’、、且5例如彩色遽膜、色轉陽極2’以使用工作函數較大之人為電極材料較佳。陽極使用之電極材料^如H 2合物作鈷、鎳、鈀、釩、鎢、氧化銦(In2〇3)、二:、卜,:銀、銅、可以單獨使用，射可 =)多。此等電極材料如蒸鍍法、濺鍍法等方法，形成在由將此等電極材料例構造，也可為多声成，之上。又’陽極可為1層下，更G 5= =%極曰之片電阻，較佳為設定在數百Ω以定，-般而：，—^右^^極之厚度視使用之電極材料材質而疋般而5，5又疋在5〜1000nm左右，更佳為1〇〜^向電洞注入輸送層3，含有—化 = 易注入電洞_之功能及輸送注入之電洞之有使油極各明之有，紐發光元件之電洞注入輪送層’可使用本發且電；Ϊ:㈡ί子化合物或其中間體高分子化合物及/或其‘ 1、if田^輸达功月匕之化合物(例如駄青衍生物、三芳胺衍生物、 ίLi 物、·衍生物、腙衍生物、笑衍生物吻坐琳L Single-layer structure: ί: Into the j-feed layer and the light-emitting layer, it is possible to send and receive an electronic private transport layer in the layer, and the layer of the present invention and the layer having the transport function. Or the intermediate of the high score of the intermediate; the polymer of the present invention; the organic hydrazine of the invention; the transport layer is better. In the macromolecularization of a compound or an intermediate thereof, it may be a compound of the present invention. The polymer of the organic electroluminescence device of the present invention may be used alone or in combination. The pole/hole is injected into the transport layer/light-emitting layer, and is not limited to, for example, (EL-1) anode (EL-2) anode/hole injection wheel ^, into the transport layer/cathode type element (Fig. 1}, Anode/light-emitting layer/electron injection/transfer layer 7 cathode type element (Fig. 2), (EL-3) light layer/cathode type element (Fig. "H element (Fig. 3), (EL-4) anode / The sender's can be used to inject the light-emitting layer 4 into the hole by the hole. The layer is sandwiched into the wind. 5) The anode 2/hole injection element (Fig. m @^ sub-injection layer 5/cathode 6 type) In the case of the optical layer, the illuminator is a component of the type of fox - 4), and the element 4a of the EB-type -6) and the electronic ampere A s8 <A ^ into the transport component 3a, the type of illuminating The component (Fig. 6); the wide form 'clamped between the pair of electrodes, such as the illuminating Z layer, allows the object to be transported into the component (Fig. 7); (EL-8): the upper shape, the loss The type component 5a held between a pair of electrodes is mixed with ... opening / ^ for the light-emitting component 4a and the electron injection, and the hole is injected into the ^ =, the type of the element between the pair of electrodes (Figure 8) The injection transport layer may at least have a hole state 4 containing the polymer compound of the present invention? ί;Multiple machines are not limited to these components, and each type is composed of 'heart S (two) = ^ sub-note layer type element, (EL-5) 3⁄4^ 牛光 3, which is (EL - υ type element, (EL —2) For the fox-!) type of component cattle, type component or wind -7) type component, better piece. Piece sister - 2) type of piece, 忸-5) type or (EL-7) type below The constituent elements of the injecting and transporting layer/inducing light-emitting element are described in detail in Fig. 1. In Fig. 1, 1 denotes a substrate, 2 denotes a thousand, denotes a light-emitting layer, and 5 denotes an electron: main #^ pole, 3表7^电The hole-injecting layer, the surface layer of the present invention, 6 means a cathode, and 7 means a power source. The glass rails such as glass are particularly limited, and the carbon is particularly limited, and the substrate 1 is preferably transparent to a half m. The non-sulphate glass towering & soil is better, the material can use soda lime glass, boric acid ester, polysulfone, polyethersulfone, polyacrylic acid 200906909 ester, polymethyl methacrylate, flat can be used half The film consisting of a through-film material, a wire, a olefin, etc., and a substrate made of a material. Further, the composite sheet can be exchanged for the film and the dielectric body can be reflected and controlled, and the color is controlled. , And 5, for example, a color enamel film, a color turning anode 2' is preferably an electrode material using a person having a larger work function. The electrode material used for the anode, such as H 2 compound, is used for cobalt, nickel, palladium, vanadium, tungsten, indium oxide ( In2〇3), 2:, Bu,: Silver, copper, can be used alone, and the shot can be =). These electrode materials, such as vapor deposition method, sputtering method, etc., are formed by the example of such electrode materials. , can also be multi-sound, above. Also 'anode can be under 1 layer, more G 5 = =% extreme sheet resistance, preferably set to hundreds of ohms to determine, - like:, -^ The thickness of the right ^^ pole depends on the material of the electrode material used, and 5,5 is also entangled at about 5~1000nm, more preferably 1〇~^ is injected into the hole into the transport layer 3, containing -chemical = easy to inject holes The function of _ and the hole for transporting and injecting make the oil electrode clear, and the hole of the new light-emitting element is injected into the polling layer', and the present invention can be used; Ϊ: (2) ί子化合物 or its intermediate polymer compound and / Or its '1, if field ^ loses the compound of Gongyue (such as indigo derivatives, triarylamine derivatives, ίLi, derivatives, anthracene derivatives, Xiaoyan Biological kiss sitting

If平Γ Γ生物、聚苯乙块㈣沖邮⑽难其衍 -成呈ί，及其Μ物 '聚~N—乙烯基味蝴中至少1種形 g。八〜同左入輸送功能之化合物，可單獨使用，或亦可併用多本每月之有機電致發光元件，較佳為電洞注入輸送層中基之高分子化合物或其中間體高分子化合物。本 ^入^電致發光元件中，能使用之其他具制注人輸送功能之化=物，例如:三芳胺衍生物(例如4,4,—雙讲__苯基—(4，，— I基苯基）胺基]-U，—聯苯、4,4，—雙^—苯基—N_(3，，—甲基苯基)胺基卜1，1'_聯苯、4,4，—雙苯基_N—(3"_甲氧基苯& 86 200906909 胺基]一 1，Γ —聯苯、4,4'一雙[N—苯基一 N —(Γ —萘基)胺基]一；^， —聯苯、3,3' —二曱基一4,4’一雙[N—苯基一N —(3，，一甲基"苯基)胺基]—1，Γ-聯苯、1，1一雙[4· —[Ν,Ν-二(4”一甲基苯基贿基]苯基] 環己烧、9，10 —雙[Ν —(4’一曱基苯基)一Ν —(4”一正丁基苯基）胺基]菲、土 3,8 —雙(Ν，Ν—二苯基胺基)一6—苯基菲η定、4—甲基—ν,Ν— 雙[4”，4”’ —雙[Ν，，Ν' —二(4—曱基苯基)胺基]聯苯—‘基]笨胺、Ν,Ν， —雙[4一(二笨基胺基)苯基]—Ν,Ν1-二苯基-1,3 —二胺基苯、Ν，Νι 一雙[4一(二苯基胺基)苯基]—Ν，Ν，一二苯基一 1，4一二胺基苯、5,’5” -雙[4 —(雙[4 —甲基苯基]胺基)笨基-2,2, ： 5，,2” -聯三屢吩、！义5 —參(一苯基胺基)苯、4,4’，4"—參(9 H—吟啥一9-基)三笨美胺、 4,4’，4” 一參[N，N —雙(4”’ 一第三丁基聯苯—4””-基)胺基]^苯基胺、I，3,5 —參[Ν—Κ —二苯基胺基)苯]等]、聚噻吩及其衍生物: 聚一N—乙烯基咔唑及其衍生物更佳。本發明之含有磺基之高分子化合物或其中間體高分子化合物與其他具電洞注入輸送功能之化合物併用之情形，電洞注入輪送層中所占此等高分子化合物之含量，較佳為〇1質量％以上，為0.5〜99.9質量〇/〇，又更佳為3〜97質量0/〇。土 3之§有石頁基之高分子化合物或其中間體高分子化二物，其他^電洞注人輸送功能之化合物併狀情形，本發明之高分子化合物或其中間體高分子化合物所構成丄層與 ς ，、電，同注入輸送功能之化合物構成之層，可以疊層。聂声 ::所iii:，磺基之高分子化合物或其中間體高= iti上，疊層其他具電職人輸送魏之化合物所構電子接^輸送層中’具電洞注人輸送功能之化合物可與 -28375^#八用。電子接ί性化合物，除了曰本特開平” 尚有FeCl3“日= 载之ΤΒΡΑΗ(參(4一漠苯基)六氯銻酸鋁)以外，有Cl3日本特開期-遍5號公報記載之參(五氟苯基) 87 200906909If Γ Γ Γ 、、、、、、、、、、四四四四四四 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 10 The compound of the eight-to-left-in transport function may be used alone or in combination with a plurality of monthly organic electroluminescent elements, preferably a macromolecule compound or an intermediate polymer compound thereof which is injected into the transport layer. In the electroluminescent device, other chemical substances that can be used for the production of a person, such as a triarylamine derivative (for example, 4, 4, - double talk __phenyl-(4,, - I-phenyl)amino]-U,-biphenyl, 4,4,-bis-phenyl-N-(3,-methylphenyl)aminodibu 1,1'-biphenyl, 4, 4,-bisphenyl_N-(3"_methoxybenzene& 86 200906909 Amino]-1, fluorene-biphenyl, 4,4'-double [N-phenyl-N-(Γ-naphthalene) Amino group]-;^,-biphenyl, 3,3'-dimercapto- 4,4'-double [N-phenyl-N-(3,,monomethyl"phenyl)amino group ]-1, Γ-biphenyl, 1,1 double [4·—[Ν,Ν-bis(4′′)methylphenyl brimbyl]phenyl]cyclohexene, 9,10 —double [Ν — (4'-Amidinoylphenyl)-anthracene-(4"-n-butylphenyl)amino]phenanthrene, soil 3,8-bis(indole, fluorene-diphenylamino)-6-phenylphenanthrene η定, 4-methyl-ν, Ν-bis[4",4"'-bis[Ν,,Ν'-bis(4-quinolylphenyl)amino]biphenyl-yl] Ν,Ν, —双[4一(二笨基胺)phenyl]-oxime, Ν1-diphenyl-1,3-diaminobenzene, Ν, Νι 一双[4 (diphenylamino)phenyl]-indole, indole, mono-diphenyl-1,4-diaminobenzene, 5, '5"-bis[4-(bis[4-methylphenyl]amine Base) Stupid base-2, 2, : 5,, 2" - Joint three repeated phenotypes, meaning 5 - ginseng (monophenylamino) benzene, 4, 4', 4 " - ginseng (9 H - 吟啥a 9-yl) triphenylamine, 4,4',4" one-[N,N-bis(4"'-tert-butylbiphenyl-4"-yl)amino]-phenylamine , I, 3, 5 - ginseng [Ν-Κ-diphenylamino)benzene], etc.], polythiophene and its derivatives: poly-N-vinylcarbazole and its derivatives are more preferred. When the sulfo group polymer compound or its intermediate polymer compound is used in combination with other compounds having a hole injection transport function, the content of the polymer compound in the hole injection transfer layer is preferably 〇1 mass. % or more, 0.5 to 99.9 mass 〇 / 〇, and more preferably 3 to 97 mass 0 / 〇. 土 3 § has a stone base polymer compound or its intermediate polymerized two, other ^ hole In the case of a compound in which a human delivery function is combined, the polymer compound of the present invention or an intermediate thereof is polymerized The layer composed of the ruthenium layer, the ruthenium, the electricity, and the compound injected into the transport function can be laminated. Nie Sheng:: iii:, the sulfo group polymer compound or its intermediate high = iti, lamination other The electric compound transports the compound in the electron transport layer of Wei's compound. The compound with the function of electron injection can be used with -28375^#. The electronic compound, except for the 曰本特开平" There is still FeCl3" Day = 载 ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( ( (

烷等硼化合物類等路易士酸。併用電子接受性化合物之情形，電子接受性化合物之含量，相對於電洞注入輸送層，以0.丨〜5〇質量％之範圍較佳。 M 發光層4，含有一化合物，該化合物具:電洞及電子之注入功能、此電洞及電子之輸送功能、藉電洞與電子之再結合使產生激子之功能。發光層，可使用本發明之含有磺基之高分子化合物或其中間體高分子化合物及/或其他具發光功能之化合物至少丨種形成。 •其他具發光功能之化合物，例如:吖咬_衍生物、啥吖唆酮j (quinacridone)衍生物、二酮基吡咯并吡咯衍生物、多環^香族化合忽〒如紅螢婦㈣聽}、惠、稠四苯m(chrys:e;、十環烯(decacyclene)、暈苯(coronene)、四苯基環戊二烯、五苯基環戊二烯二9，1〇 —二苯基蒽、9，1〇一雙(苯基乙炔基)蒽、丨，4—雙(9, —乙炔基蒽基)苯、4,4'—雙(9"一乙炔基蒽基)聯苯、二苯并[f，f]二節[l，2,3-cd : l',2’，3’-lm]花衍生物]、三芳胺衍生物(例如具電洞注入輸送功能之化合物，例如前述化合物）、有機金屬錯合物[例如參(8 —羥基喹啉)鋁、雙(1〇—苯并[h]羥基喹啉）破2 (2海·基本基)苯并嗟13坐之辞鹽、4 —經基η丫π定之鋅鹽、3 羥基頁酮之鋅鹽、5 —羥基黃酮之鈹鹽、5 —羥基黃酮之鋁赜]、 ”芪衍生物[例如U，4,4—四苯基—丁二烯、、孤 ^4,4雙(2’2 —^一本基乙細基)聯苯、4,4' —雙[(1，1，2 —三苯基） ‘乙烯基]聯笨]、香豆素衍生物(例如香豆素1、香豆素6、香豆素f、 ^子素30香豆素、香豆素138、香豆素151、香豆素152、二153、香豆素307、香豆素3H、香豆素314、香豆素334、Lewis acid such as a boron compound such as an alkane. In the case of using an electron-accepting compound, the content of the electron-accepting compound is preferably in the range of 0. 丨 to 5 〇 mass% with respect to the hole injection transport layer. The M light-emitting layer 4 contains a compound having a function of injecting holes and electrons, a function of transporting the holes and electrons, and a function of generating excitons by recombination of holes and electrons. The light-emitting layer can be formed at least by using the sulfo group-containing polymer compound of the present invention or an intermediate polymer compound thereof and/or other compound having a light-emitting function. • Other compounds with luminescent functions, such as: bite _ derivatives, quinacridone derivatives, diketopyrrolopyrrole derivatives, polycyclic ^ fragrant compounds, such as red virgins (four) listening }, Hui, fused tetraphenyl m (chrys: e;, decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene 2,1 fluorene-diphenyl Base, 9,1, bis(phenylethynyl)anthracene, anthracene, 4-bis(9,-ethynylfluorenyl)benzene, 4,4'-bis(9"-ethynylfluorenyl)biphenyl , dibenzo[f,f] two-section [l,2,3-cd : l',2',3'-lm] flower derivatives], triarylamine derivatives (such as compounds with hole injection transport function) , for example, the aforementioned compound), an organometallic complex [for example, ginseng (8-hydroxyquinoline) aluminum, bis(1〇-benzo[h]hydroxyquinoline), 2 (2 sea·base) benzopyrene 13 Sit in the salt, 4 - zinc salt determined by the base η 丫 π, zinc salt of 3 hydroxy ketone, bismuth salt of 5-hydroxyflavone, aluminum hydrazine of 5-hydroxyflavone], "deuterium derivative [such as U, 4 , 4-tetraphenyl-butadiene, orphan 4,4 double (2'2-^-based ethylidene)biphenyl, 4 , 4'-bis[(1,1,2-triphenyl) 'vinyl] phenyl], coumarin derivatives (eg coumarin 1, coumarin 6, coumarin f, ^ 30 coumarin, coumarin 138, coumarin 151, coumarin 152, di 153, coumarin 307, coumarin 3H, coumarin 314, coumarin 334,

Dr^/m33^、香丑素343、香豆素5〇0)、哌喃衍生物(例如DCM1、彡、，納衍生物(例如Nile red)、苯并噻唑衍生物、苯并噚唑Dr^/m33^, fragrant 343, coumarin 5〇0), piperidine derivatives (eg DCM1, hydrazine, nano derivatives (eg Nile red), benzothiazole derivatives, benzoxazole

苯并咪唑衍生物、吡啡衍生物、桂皮酸酯衍生物、聚一N 卡嗤及其衍生物、聚嗟吩及其衍生物、聚苯及其衍生物、策弗及其竹生物、 88 200906909 I本乙炔及其衍生物、聚聯苯乙快及其讨生物、聚聯二苯乙炔(polyterphenylenevinylene)及其衍生物、聚奈乙块及其衍生物、聚嗟吩乙炔及其衍生物等。尤其，吖啶酮衍生物、喹吖啶酮衍生物、多環芳香族化合物、三芳胺衍生物、有機金屬錯合物及芪衍生物較佳，多環芳香族化合物、金屬錯合物更佳。戍本發明之有機電致發光元件，於發光層包含本發明之基之高分子化合物或其中間體高分子化合物較佳。只Benzimidazole derivatives, pyridin derivatives, cinnamic acid ester derivatives, poly-N-carbenes and their derivatives, polybenzazole and its derivatives, polyphenylene and its derivatives, Zefer and its bamboo organisms, 88 200906909 I acetylene and its derivatives, polybiphenyl bromide and its biological, polyterphenylenevinylene and its derivatives, poly(ethylene bromide) and its derivatives, polypene acetylene and its derivatives, etc. . In particular, acridone derivatives, quinacridone derivatives, polycyclic aromatic compounds, triarylamine derivatives, organometallic complexes and anthracene derivatives are preferred, and polycyclic aromatic compounds and metal complexes are preferred. .有机 The organic electroluminescence device of the present invention preferably comprises a polymer compound of the present invention or an intermediate polymer compound thereof in the light-emitting layer. only

量％ •本發明之含有磺基之高分子化合物或其中間體高分子化合物土其^具發光功能之化合物併用之情形，發光層中所占本發二之 ^有續基之高分子化合物之比例，較佳為調節成㈣卜列·質又’發光層可如 J.Appl.Phys.，65、3610(1989)、曰本特開今 5-2=2號公報所記載，由主化合物及客化合物(攙雜物)形成。你含有石黃基之高分子化合物或其中間體高分子化名 f恭光層之主化合物使用，χ，可作為客化合物使用。主之高分子化合物或其中間體高分子化合物作為%) The polymer compound containing a sulfo group of the present invention or an intermediate polymer compound thereof, wherein the compound having a luminescent function is used in combination, and the polymer compound of the present invention having a thiol group The ratio is preferably adjusted to (4) pleats and the luminescent layer can be as described in J. Appl. Phys., 65, 3610 (1989), 曰本特开今5-2=2, by the main compound. Formation of a guest compound (noise). You have a polymer compound of the fluorescein base or an intermediate thereof. The main compound of the cheongguang layer is used, and it can be used as a guest compound. The main polymer compound or its intermediate polymer compound

5 /成發光層之情形，客化合物例如前述其他具發光# 此之化合物，其巾以多環料族化合物較佳。… J —作含有績基之高分子化合物或其中間體高分子化合物子物至少1種料料卿成。 4 7b知之化合入右機電致發光元件，較佳為發光層中含有本發明之 3 X；明分子化合物，作為主材料。作為主_ L i向分子化合物或其中間體高分子化合物 ......且仙其他具絲魏德合物之情形，發光層中 89 200906909 各材料之使用量，相對於本發明之含〇。或其中間體高分子化合物，為㈣丨〜***化合物質量％，更佳為(U〜20質量％。又，客0材吳^=為請〜30 用多數。各材枓可早獨使用，亦可併本發明之含有續基之高分子化合物物，作為客材料使用而形成發光層之情形，主材料 Γ 化if胺衍生物、有機金屬錯合物及笑衍生物較ί方i %方香私化合物、有機金屬錯合物更佳。平住夕你么含树基之高分子化合物或其巾f高分子化合物作為客材料使用之情形，該化合物較佳為使狀⑻ 更佳為_〜30質量％，又更佳為（U〜20質量％。貝里/〇電子注人輪送層5為含-化合物之層，該化合物具使得極注^電子變得容易之魏及/或具輸送注人電子之魏。κ 電子注入輪送層使用之具電子注入功能之化合物，例如至屬錯合物、噚二唑衍生物、***衍生物、三啩衍生物、茈衍生物二喹啉衍生，、喹噚啉衍生物、二苯基醌衍生物、硝基取代苐酮衍生物、二氧硫哌喃衍生物等。又，有機金屬錯合物，例如參(8 ―羥基喹啉)鋁等有機鋁錯合物、雙(1〇—苯并[h]羥基喹啉)鈹等有機鈹錯合物、5 —經基黃酮之鈹鹽、5一羥基黃酮之鋁鹽等。較佳為有機銘錯合物，更佳為具無取代或經取代之8 —羥基喹啉配位基之有機銘錯合物。具無取代或經取代之8—羥基喹啉配位基之有機鋁錯合物，例如通式(a)〜通式所示化合物。 (F)3 -Al(a) (式中’ F表示無取代或經取代之8一羥基喹啉配位基。） (F)2 — A1—〇—M(b) (式中’ F同前所述，〇一μ表示酚酸配位基，Μ表示具笨基之石炭數6〜24之煙基。） 90 200906909 (F)2 ~A1-0-A1-(F)2(c) (式中，F同前所述。）具無取代或經取代之8 —經基嗤琳配位基之有機銘錯合物之具體例，例如參(8 —羥基喹琳)鋁、參(4一甲基—8 —羥基喹啉)鋁、參(5—甲基一8 —羥基喹啉)鋁、參(3,4 —二曱基—8_羥基喹啉）鋁、參(4,5 —二甲基一8 —羥基喹琳)鋁、參(4,6~二曱基_8_羥基啥琳)铭、雙(2—甲基一8 —經基σ查淋)(酿酸)|呂、雙(2_甲基—g — 羥基喹琳)(2—甲基驗酸)鋁、雙ρ—曱基一8 —羥基喹琳)(3一曱基酚酸)鋁、雙(2 —曱基一8-羥基喹啉)(4-曱基酚酸)鋁、雙(2—甲基一8 —經基啥琳)(2—笨基i分酸)鋁、雙(2一甲基—8 ^羥基喹啉)(3 —苯基酚酸)鋁、雙(2—曱基一8 —羥基喹啉)(4—苯基酚酸)鋁、雙(2—曱基~ 8—羥基喹琳)(2,3 —二甲基驗酸)鋁、雙(2 ~甲基一8—羥基喹啉)(2,6-二曱基酚酸)鋁、雙(2—曱基—8 —經基啥琳)(3,4 —二甲基紛酸)銘、雙(2 —曱基一8~經基啥淋)(3,5 —二曱基驗酸)1呂、雙(2—曱基一8—經基喧琳)(3,5~二一第三丁基盼酸) 鋁、雙(2 —曱基一8-Μ基喹淋)(2,6—二苯基紛酸)鋁、雙(2一曱基 —8 —經基啥琳)(2,4,6 —三苯基紛酸)銘、雙(2—曱基—8 —經基喧啉)(2,4,6 —三甲基酚酸)鋁、雙(2 —曱基一8 —羥基喹啉)(2,4,5,6 —四曱基酴酸)紹、雙(2—曱基一8 —經基啥淋)(1 —萘驗酸)|呂 '雙(2 — 曱基一8 —羥基喹啉)(2—萘酚酸)鋁、雙(2,4 —二曱基一8 —羥基喹啉)(2 —苯基酚酸)鋁、雙(2,4 一二曱基一8 —羥基喹啉)(3 —苯基酚酉^) 在呂、雙(2,4 —二曱基一8 —經基口奎琳)(4—苯基酉分酸)|呂、雙(2,4 —二曱基一 8 —羥基喹啉)(3,5—二曱基酚酸)鋁、雙(2,4 —二曱基一8 —羥基喹啉)(3,5 —二一第三丁基酚酸)鋁、雙(2—曱基一8 —羥基喹啉）鋁一μ—側氧基一雙(2—曱基一8 —羥基喹啉)鋁、雙(2,4 —二曱基-8 —羥基喹琳)鋁—μ —側氧基—雙(2,4 —二曱基一8一羥基喹啉)鋁、雙(2—曱基一4一乙基一8 —羥基喹啉)鋁 ~μ—側氧基·—雙(2 —甲基一4 —乙基一8—經基喧琳)|呂、雙(2~甲 91 200906909 基二其甲t基―8 —經基啥琳）1呂—卜侧氧基—雙(2一甲基—4 叙-H 料)紹、雙(2—甲基—5—氰基―8 —經基輕) 甲美匕itΐ —雙(2—甲基—5-氰基-8-羥基喹啉)鋁、雙(2 — —51—甲f —8 —經基啥卵呂1—側氧基-雙(2—甲基 5 —齓甲基一8 —經基啥琳)鋁。能之化合物可以單獨制，亦可併用多數。電極材料較佳。陰極使用之雷極㈣就=¥幻生化合物作為納-鉀合金令y :、例，、鐘-銦合金、納、錳、m鐘合金u合金 =玎鈦、石墨薄層。此等電極材料可以單獨使用，亦;;用%孟數氟化鍾、陰極，可藉由將此等電極材料以例如^^用夕= 蒸鑛法、離子鍵膜(ion plati )法、顧法、離子注入輸送層之上。族木―離子束法，形成在電子又，陰極可為一層構造，亦可兔农數百Ω以下較佳。陰極厚产用°陰極之片電阻以 -1000- , i〇4fnJ，5 致發光元件之發光，陽極或陰極本發明之有機電透明較佳’一般而言，陽極或電極’以透明至半 .之透過率絲7齡X上較佳從L之材懈度奴域得發光光 “又，本發明之有機電致發光元件，光層及電子注入輸送層至少一層人：二、人輸送層、發氧淬熄劑，不特別限制，例如紅熄劑。單線態呋喃，較佳為紅螢烯。鏢錯5物、二苯基異苯并含有單線態氧淬熄劑之層，洞注入輸送層，更佳為電 ‘入輪误恳限佳為發光層或電有早線恶氧淬_之情形，可在 :似人輪送層含可在與電洞注入輸送層鄰接之層(例^中均句含有，亦注入輸送層)之附近含有。單&自二，層、具發光功能之電子早線恶餅熄劑之含量，為構成含^ 92 200906909 層洞注^輪送層)之全體量之0.01〜50質量％，較佳為0.05 〜30質，更佳為〇1〜2〇質量％。機電膽先元件之形成方法，不制限制，例如使用一二络鍍法、離子化蒸鍍法或溶液塗布法。、、同、、主含高分子化合物之層為電祖入輸送層之情形，電例如方法，以使用溶液塗布法較佳，溶液塗布法，塗法，線ί 4布法、微凹版塗布法、凹版塗布法、棍二;法、柔版印刷法、平版印刷峰__法, 層之形射法’可使用真空蒸鏟法、離子化墓r法 :離發光層為化==為=，錄法、離子化蒸麟或溶液塗布法形成。二工条之形Si塗;开離子化_或溶液“ΐ層In the case of 5 / into a light-emitting layer, a guest compound such as the above-mentioned other compound having a light-emitting compound is preferably a polycyclic compound compound. ... J - at least one material of the polymer compound containing the base or its intermediate polymer compound. 4b is known to be incorporated into a right electroluminescent device, preferably a light-emitting layer containing the 3X of the present invention; a molecular compound as a host material. As the main _L i molecular compound or an intermediate polymer compound thereof, and in the case of other filamentized weidite, the amount of each material used in the luminescent layer 89 200906909 is relative to the yttrium of the present invention. Or an intermediate polymer compound thereof, which is (%) 奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶奶Further, in the case where the polymer compound containing a retentate of the present invention is used as a guest material to form a light-emitting layer, the main material deuterated the amine derivative, the organometallic complex, and the laughing derivative are more than It is better to use a compound of a fragrant compound or an organic metal complex. In the case where a polymer compound containing a tree base or a polymer compound thereof is used as a guest material, the compound is preferably a shape (8). ～30% by mass, and more preferably (U~20% by mass. The Berry/〇Electronic injection layer 5 is a layer containing a compound which has an advantage of making the electrons easy and/or A compound having an electron injecting function, such as a complex, an oxadiazole derivative, a triazole derivative, a triterpene derivative, or an anthracene derivative, which is used for transporting electrons into a rotating layer. Quinoline-derived, quinoxaline derivative, diphenylanthracene derivative, nitrate Substituting an anthrone derivative, a dioxetane derivative, etc. Further, an organometallic complex such as an organoaluminum complex such as ginseng (8-hydroxyquinoline)aluminum, bis(1〇-benzo[h] An organoruthenium complex such as hydroxyquinoline), an anthracene salt of 5-pyroflavonoid, an aluminum salt of 5-hydroxyflavone, etc., preferably an organic complex, preferably an unsubstituted or substituted 8 An organic complex of a hydroxyquinoline ligand. An organoaluminum complex having an unsubstituted or substituted 8-hydroxyquinoline ligand, for example, a compound of the formula (a) to the formula. F) 3 -Al(a) (wherein 'F represents an unsubstituted or substituted 8-hydroxyquinoline ligand.) (F) 2 — A1—〇—M(b) (wherein F is the same as before The 〇-μ represents a phenolic acid ligand, and the Μ represents a ketone group having a stupid carbon number of 6 to 24.) 90 200906909 (F) 2 ~ A1-0-A1-(F) 2(c) ( Wherein F is as described above.) Specific examples of unsubstituted or substituted 8-organic complexes of the quinone ligand, such as ginseng (8-hydroxyquinoline) aluminum, ginseng (4) Monomethyl-8-hydroxyquinoline aluminum, ginseng (5-methyl-8 hydroxyquinoline) aluminum, ginseng (3 , 4 -dimercapto-8-hydroxyquinoline) aluminum, ginseng (4,5-dimethyl-8 hydroxyquinoline) aluminum, ginseng (4,6~didecyl _8_hydroxy 啥 lin) , bis (2-methyl-8)-based σ 查淋 ( ( ( ( ( ( ( ( Lulu, bis (2-methyl-g-hydroxyquinoline) (2-methyl acid) aluminum, double ρ-曱Base 8-octahydroxyquinoline (3-monophenolic acid) aluminum, bis(2-indenyl-8-hydroxyquinoline) (4-nonylphenolate) aluminum, bis(2-methyl-8) Aluminium, bis(2-methyl-8-hydroxyquinoline) (3-phenylphenolate) aluminum, bis(2-indenyl-8-hydroxyquine) Porphyrin) (4-phenylphenolate) aluminum, bis(2-indolyl-8-hydroxyquinoline) (2,3-dimethyl acid) aluminum, bis(2-methyl-8-hydroxyquinoline) ) (2,6-dimercaptophenolic acid) aluminum, bis(2-indenyl-8-transformyl) (3,4-dimethyl chlorate) Ming, double (2 - 曱基一8~啥啥 )) (3,5 - 曱曱基基 ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) ) (2 - fluorenyl-8-decyl quinone) (2,6-diphenyl phthalic acid) aluminum, bis(2-indolyl-8-methylpyrazine) (2,4,6-triphenyl) Sour and sour) Ming, double (2 - 曱—8 — via porphyrin (2,4,6-trimethylphenolate) aluminum, bis(2-indolyl-8-hydroxyquinoline) (2,4,5,6-tetradecanoic acid) ) Shao, Shuang (2 - fluorenyl- 8 - by hydrazine) (1 - naphthalene acid) | Lu 'double (2 - fluorenyl-8 hydroxyquinoline) (2-naphthol acid) aluminum, double (2,4-dimercapto- 8-hydroxyquinoline) (2-phenylphenolic acid) aluminum, bis(2,4-didecyl-8-hydroxyquinoline) (3-phenylphenolphthalein^) In Lu, bis (2,4 - dimercapto- 8 - via quinine) (4-phenylindole acid) | Lu, bis (2,4-dihydrazino-8-hydroxyquinoline) 3,5-dimercaptophenolic acid) aluminum, bis(2,4-dihydrazino-8-hydroxyquinoline) (3,5-di-di-t-butylphenolate) aluminum, bis(2-indenyl) 8-8-hydroxyquinoline) aluminum-μ-oxyl-bis(2-indenyl-8-hydroxyquinoline)aluminum, bis(2,4-didecyl-8-hydroxyquinoline)aluminum-μ Side oxy-bis(2,4-difluorenyl-8 hydroxyquinoline) aluminum, bis(2-indenyl-4-ethyl-8-hydroxyquinoline)aluminum~μ-sideoxy--double (2 - methyl - 4 - ethyl - 8 - via 喧喧琳) | Lu, Shuang (2 ~ A 91 200906909 base 2 its t-based - 8 -琳)1吕-卜- oxy-bis(2-methyl- 4 s-H material) Shao, bis (2-methyl-5-cyano-8-trans-base light) 甲美匕itΐ-double ( 2-methyl-5-cyano-8-hydroxyquinoline)aluminum, bis(2--51-methyl-f-8)-based guanidine egg- 1 side-oxy-bis(2-methyl-5-oxime Methyl-8 - via 啥 )) aluminum. The compounds can be made separately or in combination. The electrode material is preferred. The thunder pole used in the cathode (4) = phantom compound as a nano-potassium alloy y:, for example, clock-indium alloy, nano, manganese, m alloy u alloy = bismuth titanium, graphite thin layer. These electrode materials can be used alone or in combination; and the phenanthrene fluoride clock and the cathode can be used, for example, by using the electrode material, the ion plati method, and the ion plati method. Method, ion implantation on the transport layer. The family wood-ion beam method is formed in the electrons, and the cathode can be a layer structure, and it is also preferable that the rabbit farmer is several hundred ohms or less. The cathode is thickly produced with a sheet resistance of the cathode of -1000-, i〇4fnJ, the luminescence of the luminescent element, the anode or the cathode of the invention is preferably transparent. In general, the anode or the electrode is transparent to half. The transmittance of the silk at the age of 7 is better than that of the material of the L. The organic electroluminescent device of the present invention, the optical layer and the electron injecting and transporting layer are at least one layer of human: second, the human transport layer, The oxygen quenching agent is not particularly limited, and is, for example, a red quenching agent. Singlet-type furan, preferably red fluorene. Layer 5, diphenyl isophthalene containing a singlet oxygen quenching agent, hole injection and transport The layer, more preferably, the electric in-wheel misalignment is preferably the illuminating layer or the electric early-stage aerobic quenching _, in the case where the human-like rotating layer contains a layer adjacent to the hole injection transport layer (for example) ^Mean sentence contains, also injected into the vicinity of the transport layer). Single & from the second layer, with the function of the luminescent function of the electronic early line of the eclipse, the content of the composition is composed of ^ 92 200906909 layer hole injection round The total amount is 0.01 to 50% by mass, preferably 0.05 to 30, more preferably 〇1 to 2% by mass. The method for forming the biliary element is not limited, and for example, a one-two-coating method, an ion-vapor deposition method, or a solution coating method is used. The same, the main polymer-containing layer is an electro-amplitude into the transport layer. For example, a method using a solution coating method, a solution coating method, a coating method, a line coating method, a micro gravure coating method, a gravure coating method, a stick two method, a flexographic printing method, a lithographic peak method , the layer shape method can be used vacuum steaming method, ionization tomb r method: from the luminescent layer is == =, recording method, ionized steaming or solution coating method. ; open ionization _ or solution

L 劑(己燒、辛烧、魏、甲;1中:;乍=么，’例一奈·#烴系溶劑;丙酮、甲基乙基酮乙基本、卜甲基 fΥ繼化烴系溶劑;乙酸乙醋、：酸Τΐ乙 =、甲基赛路蘇、乙基赛路蘇、、：=、已醇、〜二甲基甲_、N，N—二甲基甲乙乳ί胺乙，:本甲其-醚系溶劑抑甲基—2—七坐姻、二甲基亞颯等極性“r k比洛嗣、υ 早獨使用，亦可併用多數。將電洞注入爲'、水。溶劑可以入輪送層各層成分分散於溶劑之情 ^光層、電子注月化刀散方法例如可使_磨 93 200906909 2粒=方Ϊ料振盈器、研磨機—)、均質機等，使分散成物，高物或其中間體高分子化合之層後，將上層使用烴系成含該高分子化合物合物作為電洞注人輪送層使&之，2其’將該高分子化層，光層以塗布疊用之黏結劑樹脂?^U光電子注入輸送層等各層可使聚酉旨、聚魏垸、烯基㈣、聚芳醋、聚苯乙烯、碳酸醋、聚醯胺、聚醉以脸=甲^曰 '聚丙婦酸甲醋、聚_、聚烯、聚苯氧塗度難用，又，亦可併用多數。法製作所望厚度之濃度制，施^塗布 0.5:30質量％。使用黏結劑樹月旨之^形'，盆^^ ’ 2為 =:對:形成電洞注入輪送層係相對於各成分===== 不特為子注人輸送層等各層之膜厚，於鈍性物質中(例如石蠟夜體,、曰山二？或將兀件密封氣碳油)並保護。保護層使用"：=，'=有^^ '含^石之氧樹脂、矽酮樹脂、環氧矽酮樹脂 '聚‘烯，:氟 —、聚_、聚醯亞胺、聚醯胺醯亞胺、聚對ί甲J§:聚 94 200906909 璃埽金、無 ==如，、非晶珍土、電絕緣性玻例如光硬化性樹脂’。保镬声使用之=物、金屬硫化物），再者，多數。 ”產a使用之材料可以單獨使用，亦可併用，護f，1層構造’也可為多層構造。么月之有機電致發光元件，可在帝搞4Π*罟你盔仅雄γ 之金ft化物臈(例如氧化_、金屬氟化膜為保濩膜層）本發明之有機電致發光元件，可在陽極 1面設置界面層（中間物、酉:例如:有_化合物、聚魏、芳香族胺衍生聚處使;極’例㈣極可在其表面⑽、氨/過氧化氫、或電使用本電致發光元件，通常可作為直流驅動型之元件 3光為ΐ流驅動型元件使用。又，本發明型，x亦可為TFT(:t(riment)型、單純矩陣驅動型等被動驅動初主，¾勃冤壓通常為2〜3〇ν。本發了可使用於面板型光源(例如時鐘电^二7〇件件糾LED料光蝴、各麵發光元行動電話•行動終端_示元件Μ :各種^ r用在習知導3電化 ΐίί 巴兀仟(£CD)、抗靜電劑等用途。 τ屯致變【實施例】實施7，料施觸本發明更詳細説明，但本發料限於以下 95 200906909L agent (hexilated, simmered, Wei, A; 1 in:; 乍 = 么, '例一奈·# hydrocarbon solvent; acetone, methyl ethyl ketone ethyl, methyl methyl hydrazine hydrocarbon solvent; acetic acid Ethyl vinegar, acid Τΐ B =, methyl 赛路苏, ethyl 赛路苏,, =, hexane, dimethyl dimethyl ketone, N, N-dimethyl ethane acetamide, The methyl-ether-based solvent inhibits the polarity of methyl 2-n-satin, dimethyl hydrazine, etc. The rk is used in combination with 嗣, υ, and may be used in combination. The hole is injected into water and the solvent. The components of each layer of the infeed layer are dispersed in the solvent. The optical layer and the electronic injection method can be dispersed, for example, to make the _ mill 93 200906909 2 grains = square material vibrating device, grinding machine -), homogenizer, etc. After the polymer, the high substance or the intermediate thereof is polymerized, the upper layer is made of a hydrocarbon compound to form the polymer compound compound as a hole injection layer, and the polymer is polymerized. The layer and the light layer are coated with a layer of a binder resin, a photoelectron injection layer, and the like, and the layers can be used for the polymerization, polyfluorene, alkenyl (tetra), polyaryl vinegar, polystyrene, carbonated vinegar, polyfluorene. , drunk with face = A ^ 曰 'polyglycolic acid methyl vinegar, poly _, polyene, polyphenylene oxide coating is difficult to use, but also can be used in combination. The method is used to make the concentration of the desired thickness, apply 0.5 coating: 30% by mass. Use the binder tree to form the shape of the moon, the pot ^^ ' 2 is =: pair: forming a hole injection rounding layer relative to each component ===== not special for the human injection layer The film thickness of each layer is protected in a blunt substance (for example, paraffin night body, 曰山二? or the sealing member is sealed with carbon oil). The protective layer is used ":=, '=有^^ ' contains ^ Stone Oxygen Resin, Anthrone Resin, Epoxy Ketone Resin 'Poly' Aene, Fluorine-, Poly-, Poly-imine, Polyamidamine, Poly-J-J: Poly 94 200906909 Gold, no ==, for example, amorphous rare earth, electrically insulating glass such as photocurable resin '. used to protect the sound of sound, metal sulfides, and, more, most." It can also be used in combination, and the f-layer structure can also be a multi-layer structure. The organic electroluminescent element of the present invention can be used in the emperor to make 4 Π * 罟盔盔仅 γ γ γ 臈臈臈臈臈臈臈臈臈臈臈臈、、、、、、、、、、、、、、、、、、、、 An interfacial layer can be placed on the surface of the anode (intermediate, yttrium: for example: _compound, poly-wei, aromatic amine-derived polycondensation; polar 'example (iv) can be on its surface (10), ammonia/hydrogen peroxide, or electricity In the present electroluminescence device, it is generally used as a DC drive type element 3 light for a trickle drive type element. Further, in the present invention type, x can also be passive (such as a t (riment) type or a simple matrix drive type). Drive the initial, 3⁄4 Burgundy is usually 2~3〇ν. This can be used for panel-type light sources (such as clock electric ^ 2 〇件纠纠 LED 、、、、、、、、、、、、、、、、、、、、 _ shows the components Μ: various ^ r used in the conventional guide 3 electrification ΐ ί 兀仟 £ (£CD), antistatic agent, etc. τ 屯【 [Examples] Implementation 7, the material touches the present invention to explain in more detail, However, this release is limited to the following 95 200906909

又，各實施例中之分子量’藉由凝膠滲透層析(GPC)，測定聚苯乙烯換算之數平均分子量。 A (GPC分析條件）裝置：凝膠滲透層析GPC 101(Shodex社製）檢測器：示差折射計管柱：GPCK—806LX3(8.0mmI.D.x30cm，Shodex 社製）管柱溫度：40度溶劑：氯仿注入量：1〇〇μ1 流速：lml/min 標準物質：單分散聚苯乙烯(Shodex社製）紫外線吸收光譜，使用以下裝置測定，求吸收極大波長 (Xmax) ° (UV(Xmax)) 使用島津製作所製紫外可見分光光度計uv—2500PC測定。成膜性評價，以原子力顯微鏡(Atomic Force Microscope， AFM)，觀察表面粗糙度以確認。 (AFM測定條件）裳置：Seiko Instruments製掃描探針顯微鏡SPI—3800N .分析條件：測定模式DFM Cantilever SI—DF20 測定範圍5μηΡ<5μιη 磺基數，係以元素分析決定。 [實施例1] 例示化合物Al —1之製造於Ν,Ν'-雙[對(9Η—咔唑—9-基)苯基]— Μ—苯二胺ug、 2,5 —雙(4，一溴苯基)一3,4—二苯基噻吩l」9g、第三丁醇鈉061g 及鄰二曱苯25ml之混合物中，於氮氣流下’添加參(二苯亞曱基 96 200906909 =酮)二纪9. 8mg及三苐三丁基膦17.3mg之鄰二液。於氮鼠圍下，於135度娜4小時。使反應液回至室温，將反應液以謂管柱層析精製後，倒到丙酮中，據Further, the molecular weight in each of the examples was measured by gel permeation chromatography (GPC) to determine the average molecular weight in terms of polystyrene. A (GPC analysis conditions) Device: Gel permeation chromatography GPC 101 (manufactured by Shodex) Detector: Differential refractometer column: GPCK-806LX3 (8.0 mmI.D.x30 cm, manufactured by Shodex) Column temperature: 40 degrees Solvent: chloroform injection amount: 1 〇〇 μ1 Flow rate: 1 ml/min Standard material: monodisperse polystyrene (manufactured by Shodex) Ultraviolet absorption spectrum, measured by the following means, and the absorption maximum wavelength (Xmax) ° (UV (Xmax) ) Measured by UV-Vis spectrophotometer uv-2500PC manufactured by Shimadzu Corporation. The film formation property was evaluated by observing the surface roughness with an Atomic Force Microscope (AFM). (AFM measurement conditions) Sputum: Scanning probe microscope SPI-3800N manufactured by Seiko Instruments. Analysis conditions: Measurement mode DFM Cantilever SI-DF20 Measurement range 5 μηΡ < 5 μιη Sulf number was determined by elemental analysis. [Example 1] The exemplified compound Al-1 was produced in Ν,Ν'-bis[p-(9Η-carbazole-9-yl)phenyl]-non-phenylenediamine ug, 2,5-bis (4, In a mixture of monobromophenyl)-3,4-diphenylthiophene 1", 061 g of sodium butoxide, and lycopene 25 ml, the addition of ginseng (diphenylarylene 96 200906909 = ketone) under a nitrogen stream 2, 2 mg of oligarchic acid of 9. 8 mg of trigeminal and 17.3 mg of tributylphosphine. Under the nitrogen mouse, at 135 degrees Na for 4 hours. The reaction solution was returned to room temperature, and the reaction solution was purified by column chromatography and poured into acetone.

Al —l)1.45g黃色固體。分子量：21000 UV(Xmax) ·· 346nm(曱笨） [實施例2] 例示化合物A1 —3之製造Al - l) 1.45 g of a yellow solid. Molecular weight: 21000 UV (Xmax) · 346 nm (曱 )) [Example 2] Production of exemplified compound A1-3

—將實施例1中使用N，N，一雙[對(9H—咔唑〜9_基)笨基]—14 —苯二胺1.30g改為使用N，N，一雙[對(N，N〜二笨基胺基基]二 1，4—苯二胺1.26g，除此以外，依照實施例i之方法，得到你^ 合物A1 —3之高分子化合物1.39g。數平均分子量：25000 [實施例3] 例示化合物A1 —4之製造將實施例1中使用N，N’_雙[對(9H—咔唑—9-基)苯基]—1，4 一苯二胺1.30g改為使用Ν,Ν' —雙[對(3,6 —二己基—9H—味嗤1 9-基)苯基]— 1,4—苯二胺2.10g ’除此以外依照實施例1之方法， _得到例示化合物A1—4之高分子化合物1.91g。數平均分子量：21600 [實施例4] 例示化合物A1 —5之製造將實施例1中使用Ν,Ν' —雙[對(9H—咔唑一9-基)苯基]— 1,4 一苯二胺l_30g改為使用Ν，Ν’ —雙[對{Ν—(對辛基苯基)—(對己基苯基)胺基}苯基]—1,4—苯二胺2.10g ’除此以外依照實施例1 之方法，得到例示化合物A1 — 5之高分子化合物1.91g。數平均分子量：18800 [實施例5] 97 200906909 例示化合物Al —8之製造將實施例1中使用N，N’一雙[對(9H—咔唑—9-基)苯基]—1,4 一苯二胺1.3〇g改為使用N，N'_雙[對{N—苯基一n—(4—苯基笨基)胺基}本基]—1，4—^—胺1.59g，除此以外依照實施例1之方法，得到例示化合物A1 —8之高分子化合物丨51g。數平均分子量：Π300 [實施例6] 例示化合物A1 —9之製造將實施例1中使用Ν,Ν1-雙[對(9H-咔唑—9-基)苯基]— 1,4 —笨二胺1.30g改為使用Ν，Ν'-雙[對{Ν，Ν—二(4-笨基苯基)胺基} 苯基]—1，4—苯二胺1.91g，除此以外依照實施例1之方法，得到例示化合物A1 —9之高分子化合物1.83g。數平均分子量：15600 [實施例7] 例示化合物A1 —10之製造將實施例1中使用N，N' —雙[對(9H—咔唑一9-基)苯基]— 1,4 —苯二胺1.30g改為使用N，N’一雙[對{N-苯基一N —(4-二苯基胺基苯基)胺基}苯基]—1，4一苯二胺1.97g，除此以外依照實施例1 之方法5彳寸到例不'化合物A1 — 10之局分子化合物1.72g。數平均分子量：24100 [實施例8] 例示化合物A1 —11之製造將實施例1中使用Ν,Ν’一雙[對(9H—咔唑一9-基)苯基]一 1，4 —苯二胺1.30g改為使用Ν,Ν’一雙[對{Ν，Ν—二(4~二苯基胺基苯基)胺基}苯基]一 1，4一苯二胺2.69g，除此以外依照實施例1之方法，得到例示化合物A1 —11之高分子化合物2.29g。數平均分子量：27200 [實施例9] 例示化合物A1 —12之製造 98 200906909 將實施例1中使用N，N’一雙[對(9H—咔唑一9-基)苯基]—1,4 —笨二胺1.30g改為使用Ν,Ν' —雙[對[N-苯基一Ν-〇^(9Η〜咔唆一9-基)苯基}胺基]苯基]— 1,4—苯二胺1.97g，除此以外依照實施例1之方法，得到例示化合物A1 —12之高分子化合物i.76g。數平均分子量：14300 [實施例10] 例示化合物A1 —13之製造將實施例1中使用N，N’一雙[對(9H-咔唑一9-基)笨基^ — —^—fe 1.30g改為使用N，N —雙[對[N，N—二{對(9只~~u卡〇坐一9_ 墓)苯基}胺基]苯基]—I，4—苯二胺2.67g，除此以外依照實施例i 之方法，得到例示化合物A1 —13之高分子化合物2.24 f 數平均分子量：25800 §〇 [實施例11] 例示化合物A1 —14之製造將實施例1中使用Ν,Μ —雙[對(9H—咔唑一9-基)苯某 —本一胺1.30g改為使用N，Nf—雙[對{N—苯基一N〜(4 —w一苯基~N— 1 —萘基)胺基苯基)胺基}苯基]—丨’彳―苯二胺2 此 g夕if照實施例1之方法’得到例示化合物A1 一14之高^子化合數平均分子量：22100 [實施例12] 1列不化合物—15之製造將實施例1巾使用Ν,Ν，-雙[對(9H—柯―9 4 :苯二胺1.30g改為使用取，—雙[對{N—苯基，:4本二二苯，N—2__胺基苯基)胺基}苯基卜苯二心((N除此 ^ ^貫施例1之方法，得到例示化合物A1 —15之高分子化合數平均分子量：21100 [實施例13] 99 200906909 例示化合物Al —17之製造將實施例1中使用N，N，一雙[對(9H—咔唑—9-基)笨美]一 14 —笨二胺1.30g改為使用N，N，一雙[對{N—笨基—N —基)胺基}苯基]—1，4—笨二胺1.69g，除此以外依照實施例i之方法，得到例示化合物A1 —17之南分子化合物u〇g。數平均分子量：16200 [實施例14] 例示化合物A1 —18之製造將實施例1中使用Ν,Ν1 —雙[對(9H—咔唑—9-基)苯基]一 1,4 ~~本一胺1.30g改為使用Ν，Ν’ —雙[對苯基—Ν—(9—蒽基)胺基}苯基]一1，4—苯二胺1.69g，除此以外依照實施例丨之方法，得到例示化合物A1 —18之高分子化合物168g。數平均分子量：13300 [實施例15] 例示化合物A2 —2之製造將實施例1中使用N，N，一雙[對(9H—咔唑—9-基)苯基]一 1,4 —本一胺1.30g改為使用；N，1ST —雙[對(3,6 —二己基一9Ιί—叶0生一 9-基)苯基苯基]— 1,4—苯二胺2.304g，除此以外依照實施例1之方法’得到例示化合物A2-2之高分子化合物2 〇2g。數平均分子量：23100 [實施例16] 例示化合物A2 —6之製造將實施例1中使用N，N，一雙[對(9H—咔唑—9-基)苯基]〜1,4 —本一胺1.30g改為使用N，N’一雙[4—{對]^~苯基一n — (1 —萘基) 胺基}苯基苯基]一 1,4—苯二胺i.8〇g’除此以外依照實施例1之方法，得到例示化合物A2 — 6之高分子化合物1；72g。數平均分子量：21100 [實施例17] 例示化合物A2 —7之製造 100 200906909 將實施例1中使用N，N’一雙[對(9H—咔唑一9-基)苯基]—1，4 —苯二胺1.30g改為使用n，N，-雙[4一 (對N-苯基一N—(2—萘基) 胺基}笨基苯基]—1,4—苯二胺1.8g，除此以外依照實施例1之方法’得到例示化合物A2 — 7之高分子化合物1.75g。數平均分子量：14100 [實施例18] 例示化合物A3 —1之製造將實施例1中使用N，N'—雙[對(9H—咔唑—9-基)苯基]—1,4 -苯二胺1.30g改為使用ν,：ΝΓ —雙{2 —(7—Ν，Ν~二苯基胺基一9,9 —二曱基)苐基}一1，4~苯二胺1.76g，除此以外依照實施例1之方法，得到例示化合物A3 —1之高分子化合物1.71g。數平均分子量：20600 [實施例19] 例示化合物A3 —2之製造將實施例1中使用N，N’一雙[對(9H—咔唑〜9-基)苯基]—1，4 ~苯二胺1.30g改為使用ν,Ν’一雙{2 —(7—N，N-二苯基胺基一9,9 ~—辛基)第基} —M—苯二胺2.59g，除此以外依照實施例1之方法，得到例示化合物A3 —2之高分子化合物2.17g。數平均分子量：24100 [實施例20] 例示化合物A3 —4之製造將實施例1中使用N，N'—雙[對(9H—咔唑〜9_基)苯基]—1,4 ~苯二胺1.30g改為使用N，N’ 一雙[2 — {7 — (9H —味嗅一9-基)一9,9 ~二曱基}筅基]一 1，4一苯二胺1.75g ’除此以外依照實施例1之方法，得到例示化合物A3 —4之高分子化合物l.66g '/ 數平均分子量：26100 [實施例21] 例示化合物A3 —6之製造將實施例1中使用N，N' —雙[對(9H—味嗓〜9_基)苯基]—1,4 101 200906909 —笨二胺13〇g改為使用N，N，一雙[2—{7 — (3,6—二己基一911-吟唑一9-基)一9,9 —二曱基}第基;I—1，4—笨二胺2.54g，除此以外依照實施例1之方法，得到例示化合物A3 — 6之高分子化合物2.11g。數平均分子量：27800 [實施例22] 例示化合物A3 —7之製造將實施例1中使用Ν,Ν'—雙[對(9H—咔唑一9-基)苯基]一 1，4 ~苯二胺u〇g改為使用ΚΝ，一雙Ρ—{7 —(Ν—(對辛基笨基)—ν 厂(對己基苯基)胺基)一9,9 —二曱基}第基卜笨二胺2 58g，除此以外依照實施例1之方法，得到例示化合物A3 —7之高分子化合物2.32g。數平均分子量：32100 [實施例23] 例示化合物B1 — 1之製造 ^將實施例1中使用N，N' —雙[對(9H—咔唑一9-基)苯基]_ι,4 :苯二胺l.3〇g改為使用N，N，—雙[對{N，N_二(4—己基苯基)胺基} 笨基]—1,3—苯二胺1.98g，除此以外依照實施例1之方法，得到例示化合物Bl —1之高分子化合物LWg。數平均分子量：19400 [實施例24] 例示化合物B1 ~2之製造 —將實施例1中使用N，N，一雙[對(9H—咔唑一9-基)苯基]—14 ''苯二胺1.30g改為使用N,N，—雙[對—二苯基胺基基]二 3_，3f〜二胺基聯苯L43g，除此以外依照實施例〗之方法，得到例示化合物B1 — 2之馬分子化合物i.45g。數平均分子量：15600 [實施例25] 例示化合物—5之製造將實施例1中使用N，N’-雙[對(9H-咔唑—9-基)苯基]—μ 102 200906909 ~本二胺1.30g改為使用]Si，lSr —雙[對{(N—(對辛基苯基)—n—(對己基苯基)胺基)苯基} —1，5 —萘二胺2‘20g，除此以外依照實施例1 之方法’得到例示化合物B1 — 5之高分子化合物U5g。數平均分子量：22000 [實施例26] 例示化合物B1 —6之製造將實施例1中使用N，N'—雙[對(9H—味哇—9-基)苯基]—14 〜本二胺l.3〇g改為使用N，N' —雙[對(Ν,Ν—二苯基胺基)苯基]—- In Example 1, N, N, a pair of [p-(9H-carbazole~9-yl) styryl]-l-phenylenediamine 1.30g was used instead of N, N, a pair [N, (N, In the same manner as in Example i, 1.39 g of a polymer compound of the compound A1-3 was obtained, except that 1.26 g of N-diphenylaminoamino]di-1,4-phenylenediamine was obtained. 25000 [Example 3] Production of exemplified compound A1-4 The N,N'-bis[p-(9H-carbazole-9-yl)phenyl]-1,4-phenylenediamine 1.30 g was used in Example 1. Instead of using Ν, Ν ' - bis [p-(3,6-dihexyl-9H- miso 19-yl)phenyl]-1,4-phenylenediamine 2.10 g 'except according to Example 1 Method, _ obtains 1.91 g of the polymer compound of the exemplified compound A1-4. Number average molecular weight: 21600 [Example 4] Production of the exemplified compound A1-5 The use of Ν, Ν'-double [pair (9H-) in Example 1 Indole-9-yl)phenyl]-1,4-phenylenediamine l_30g was changed to use hydrazine, Ν'-bis[p-{Ν-(p-octylphenyl)-(p-hexylphenyl)amino} Phenyl]-1,4-phenylenediamine 2.10 g 'In addition to the method of Example 1, an exemplary compound A1-5 was obtained. Molecular compound 1.91 g. Number average molecular weight: 18800 [Example 5] 97 200906909 Preparation of the exemplified compound Al-8 The N,N'-double [p-(9H-carbazole-9-yl)phenyl group used in Example 1 ]-1,4-phenylenediamine 1.3〇g was changed to use N,N'_bis[p-{N-phenyl-n-(4-phenylphenyl)amino}yl]-1,4- The polymer compound 丨51g of the exemplified compound A1-8 was obtained according to the method of Example 1. The number average molecular weight: Π300 [Example 6] Production of the exemplified compound A1-9 Example 1 In the use of hydrazine, Ν1-bis[p-(9H-carbazol-9-yl)phenyl]-1,4-phenylene diamine 1.30g was changed to use Ν, Ν'-double [to {Ν, Ν-two ( In addition, 1.83 g of the polymer compound of the exemplified compound A1-9 was obtained according to the method of Example 1, except that 1.91 g of 4-phenylphenyl)amino}phenyl]-1,4-phenylenediamine was obtained. :15600 [Example 7] Production of exemplified compound A1-10 The N,N'-bis[p-(9H-carbazol-9-yl)phenyl]-1,4-phenylenediamine 1.30 was used in Example 1. g is changed to use N, N' a pair [for {N-phenyl-N-(4-diphenylamino) Further, according to the method of Example 1, the method of Example 1 was carried out, except that the compound of the compound A1-10 was 1.72 g. The number average molecular weight: 24100 [Example 8] Production of exemplified compound A1-11 The hydrazine, Ν'-double [p-(9H-carbazol-9-yl)phenyl]-1,4-diphenylamine 1.30 g was used in Example 1. Instead of using Ν, Ν 'a pair of [p-{Ν, Ν-bis(4-diphenylaminophenyl)amino} phenyl]-1,4-phenylenediamine 2.69g, in addition to the implementation In the method of Example 1, 2.29 g of the polymer compound of the exemplified compound A1-11 was obtained. Number average molecular weight: 27200 [Example 9] Production of exemplified compound A1-12 98 200906909 N,N'-double [p-(9H-carbazole-9-yl)phenyl]-1,4 was used in Example 1. - Stupid diamine 1.30g is changed to use Ν, Ν ' - bis [p-[N-phenyl- Ν-〇^(9Η~咔唆9-yl)phenyl}amino]phenyl]-1,4 A polymer compound i.76 g of the exemplified compound A1-12 was obtained according to the method of Example 1, except that 1.97 g of phenylenediamine was obtained. Number average molecular weight: 14300 [Example 10] Production of the exemplified compound A1 - 13 The N, N'-double is used in Example 1 [p-(9H-carbazole-9-yl) stupid base ^-^-fe 1.30 g is changed to use N, N - double [for [N, N - two { pairs (9 ~ ~ u card 〇 sit a 9_ tomb) phenyl} amino] phenyl] - I, 4-phenylenediamine 2.67 g, otherwise, according to the method of Example i, the polymer compound of the exemplified compound A1-13 was obtained. 2.24 f number average molecular weight: 25,800 § 〇 [Example 11] Manufacture of the exemplified compound A1 - 14 , Μ - bis [p-(9H-carbazole-9-yl) benzene - this amine 1.30g instead use N, Nf - double [for {N-phenyl-N~(4-w-phenyl~ N-1-1-naphthyl)aminophenyl)amino}phenyl]-丨'彳-phenylenediamine 2 This method is obtained by the method of Example 1 to obtain the high compound number of the exemplified compound A1-14. Average molecular weight: 22100 [Example 12] 1 column of non-compound-15 was produced. Example 1 was used for the use of Ν, Ν, - bis [(9H-Ke- 9 4 : phenylenediamine 1.30g was used instead, - Double [p-{N-phenyl,: 4 dibiphenyl, N-2_-aminophenyl) amine} phenyl benzene ((In addition to the method of Example 1, the polymer compound number average molecular weight of the exemplified compound A1-15 was obtained: 21100 [Example 13] 99 200906909 Production of the exemplified compound Al-17 The N used in Example 1 , N, a pair [p. (9H-carbazole-9-yl) stupid] -14 - stupid diamine 1.30g instead use N, N, a pair of [p-{N-stupyl-N-yl) amine The south molecular compound u〇g of the exemplified compound A1-17 was obtained according to the method of Example i except that the base phenyl]-1,4-pisuccinamine was 1.69 g. Number average molecular weight: 16200 [Example 14] The production of the exemplified compound A1-18 was carried out in Example 1, using hydrazine, hydrazine 1 - bis[p-(9H-carbazol-9-yl)phenyl]- 1,4 ~~1. An exemplified compound A1-18 was obtained according to the method of Example —, except that bis[p-phenyl-indole-(9-fluorenyl)amino}phenyl]-1,4-phenylenediamine 1.69 g. Polymer compound 168 g. Number average molecular weight: 13300 [Example 15] Production of exemplified compound A2-2 The N, N, one pair [p-(9H-carbazole-9-yl)phenyl]-one was used in Example 1. 1,4 - the original amine 1.30g was changed to Use: N, 1ST - bis [p-(3,6-dihexyl- 9 Ι ̄ _ _ _ _ 9-yl) phenylphenyl]-1, 4-phenylenediamine 2.304g, in addition to Example 1 The method 'to obtain the polymer compound 2 〇 2g of the exemplified compound A2-2. Number average molecular weight: 23100 [Example 16] Production of exemplified compound A2-6. N, N, a pair of [p-(9H-carbazole-9-yl)phenyl]~1,4-beneficially used in Example 1. 1. A. 1.30g of an amine is used instead of N, N', a pair of [4-{p.]^~phenyl-n-(1-naphthyl)amino}phenylphenyl]-1,4-tetraphenylamine. A polymer compound 1 of the exemplified compound A2-6; 72 g was obtained according to the method of Example 1 except for 8 g. Number average molecular weight: 21100 [Example 17] Production of exemplified compound A2-7 100 200906909 The N,N'-double [p-(9H-carbazole-9-yl)phenyl]-1,4 was used in Example 1. - 1.30g of phenylenediamine is replaced by n, N, - bis [4 - (p-N-phenyl-N-(2-naphthyl)amino)} phenyl phenyl]-1,4-phenylenediamine 1.8 g, except that the polymer compound of the exemplified compound A2-7 was obtained in accordance with the method of Example 1. 1.75 g. Number average molecular weight: 14100 [Example 18] Production of the exemplified compound A3-1 The use of N in Example 1, N'-bis[p-(9H-carbazole-9-yl)phenyl]-1,4-phenylenediamine 1.30g was changed to use ν,: ΝΓ - double {2 - (7 - Ν, Ν ~ diphenyl) A polymer compound of the exemplified compound A3-1 was obtained in accordance with the method of Example 1, except that 1.67 g of a arylamino-9,9-diindenyl) fluorenyl}-1,4-diphenyleneamine was obtained. Average molecular weight: 20600 [Example 19] Production of exemplified compound A3-2 The N,N'-double [p-(9H-carbazole~9-yl)phenyl]-1,4-benzene was used in Example 1. The amine 1.30g is changed to use ν, Ν 'a pair of {2 - (7-N, N-diphenylamino-9,9 ~- In addition, 2.17 g of the polymer compound of the exemplified compound A3-2 was obtained according to the method of Example 1. The number average molecular weight: 24100 [Example 20] Illustrative compound A3 -4) The use of N,N'-bis[p-(9H-carbazole~9-yl)phenyl]-1,4-phenylenediamine 1.30g in Example 1 was changed to N, N' [2 - {7 - (9H - odorant-9-yl)-9,9-didecyl} fluorenyl]-1,4-phenylenediamine 1.75 g 'In addition to the method of Example 1, Illustrative compound A3-4 polymer compound 1.66g '/ number average molecular weight: 26100 [Example 21] Production of exemplified compound A3-6 The N,N'-double [pair (9H- miso) used in Example 1 〜9_基)Phenyl]-1,4 101 200906909 - Stupid diamine 13〇g is changed to N, N, a pair [2—{7 — (3,6-dihexyl-911-carbazole-9 Further, according to the method of Example 1, 2.11 g of the polymer compound of the exemplified compound A3-6 was obtained, except that the compound was subjected to a compound of the compound of the compound A3-6. Number average molecular weight: 27800 [Example 22] Production of exemplified compound A3-7 In Example 1, hydrazine, Ν'-bis[p-(9H-carbazole-9-yl)phenyl]-1,4-diphenyldiamine u〇g was used instead of hydrazine, a pair of hydrazines-{7-( Further, according to the method of Example 1, except that ν-(p-octyl phenyl)- ν (p-hexylphenyl)amino)- 9,9-didecyl}diyl bromide 2 58 g was obtained. The polymer compound of the compound A3-7 was exemplified by 2.32 g. Number average molecular weight: 32100 [Example 23] Production of exemplified compound B1 - 1 Using N, N' - bis [p-(9H-carbazole-9-yl)phenyl]_ι, 4: benzene in Example 1 The diamine l.3〇g was changed to use N,N,-bis[p-{N,N-di(4-hexylphenyl)amino}phenyl]-1,3-phenylenediamine 1.98 g, The polymer compound LWg of the exemplified compound B1-1 was obtained in the same manner as in Example 1. Number average molecular weight: 19400 [Example 24] Production of exemplified compound B1 ~ 2 - N, N, a pair of [p-(9H-carbazole-9-yl)phenyl]-14''benzene was used in Example 1. The divalent amine 1.30g was replaced with N,N,-bis[p-diphenylamino]di 3_,3f~diaminobiphenyl L43g, except that the exemplified compound B1 was obtained according to the method of the example. 2 horse molecular compound i.45g. Number average molecular weight: 15600 [Example 25] Production of exemplified compound-5 The N,N'-bis[p-(9H-carbazole-9-yl)phenyl]-μ 102 200906909 ~ Ben 2 was used in Example 1. The amine 1.30g was changed to use]Si,lSr-bis[p-{(N-(p-octylphenyl)-n-(p-hexylphenyl)amino)phenyl}-1,5-naphthalenediamine 2' A polymer compound U5g of the exemplified compound B1-5 was obtained in the same manner as in Example 1 except for 20 g. Number average molecular weight: 22000 [Example 26] Production of exemplified compound B1-6 The use of N,N'-bis[p-(9H-flavor-9-yl)phenyl]- 14-present diamine in Example 1 L.3〇g is changed to use N,N'-double [p-(Ν,Ν-diphenylamino)phenyl]-

奈一胺1.37g ’除此以外，依照實施例1之方法，得到例示化合物B1 —6之高分子化合物1.40g。數平均分子量：23800 [實施例27] 例示化合物B1—7之製造將實施例1中使用Ν，Ν· —雙[對(9H—咔唑—9-基)苯美]—14 一苯二胺1.30g改為使用Ν,Ν，_雙[對(ν，ν〜二笨基^基基]二 3,6—芘二胺1.53g ’除此以外依照實施例1之方法，得物~7之高分子化合物l,51g。 ’ 數平均分子量：21600 [實施例28] 例示化合物B1 — 8之製造將實施例1中使用Ν,Ν，-雙[對(9H —咔唑—9_其)苯夷 4 〜苯二胺UOg改為使用Ν，Ν，一雙[對(ν，ν〜二苯^ ^ ’ 巧-肛胺，，除此以外依照實施例1之; 5物Β1 —8之南分子化合物i.53g。數平均分子量：14700 [實施例29] 例示化合物B1 —9之製造將實施例1中使用N，N，一雙[對(9H—咔唑—9_美其〜苯二胺13Gg改為使用N，N’ —雙[對(耶〜二苯基^基g基卜 103 200906909 3,7-二苯并吱喃二胺1.46g，除此以外依照實施例i之方法，得到例示化合物B1 —9之高分子化合物。數平均分子量：28400 [實施例30] 例示化合物B1 — 10之製造將貫施例1中使用N，N'—·雙[對(9H—π卡嗤一9-基)笨基]—1，4 ~~笨二胺1.3〇g改為使用Ν,Ν1 —雙[對(Ν,Ν—二苯基胺基)苯基]— 2,8二二苯并噻吩二胺1.49g，除此以外依照實施例丨之方法，得到例示化合物B1 —10之高分子化合物145g。 k平均分子量：16200 -[實施例31] 例示化合物B1 —11之製造將實施例1中使用Ν,Ν，一雙[對(9H—咔唑一9-基)苯基]一；1，4 —苯二胺l.3〇g’改為使用Ν，Ν’ —雙[對(Ν,Ν—二苯基胺基)苯基] 二4,4’·硫雙苯胺1.49g，除此以外依照實施例i之方法，得到例示化合物B1 —11之高分子化合物1.50g。數平均分子量：12300 [實施例32] 例示化合物B1 —12之製造 -將實施例1中使用Ν,Ν1—雙[對(阳一咔唑一9_基)苯基]—1;4 本一胺UOg改為使用1 ~(9,9 —二曱基苐基)—NJST —雙[對 —二笨基胺基)苯基]一3,7 —咔唑二胺1.86g，除此以外依照實施例 1之方法，得到例示化合物B1 — 12之高分子化合物i.68g。數平均分子量：11400 [實施例33] 例示化合物Bl~ 13之製造將實施例1中使用Ν,Ν1—雙[對(9H—味唾—9-基)苯基]―丄4 〜苯二胺1.3〇g改為使用4,4,一(1—曱基亞乙基)一雙[N—{對化^ —一苯基胺基)苯基}苯胺]1.51g，除此以外依照實施例1之方法， 104 200906909 得到例示化合物Bl —13之高分子化合物1.55g。數平均分子量：13800 [實施例34] 例示化合物B1 —14之製造將實施例1中使用Ν,Ν，一雙[對(9H—咔唑一9-基)苯基]—1，4 一苯二胺1.30g改為使用3,3,一(1—甲基亞乙基)一雙β—'ί對一二苯基胺基)苯基}苯胺]1.51g，除此以外依照實施例1之方法’ 得到例示化合物B1 —14之高分子化合物1.49g。數平均分子量：12900 '[實施例35] • 例示化合物B1 —15之製造將實施例1中使用N，N，一雙[對(9H—咔唑一9-基)苯基]— 1,4 -苯二胺1.30g改為使用1,1 一雙[{N-4 —(4’一N,N—二苯基胺基) 苯基}一4-胺基苯基]環己烷1.6〇g ’除此以外依照實施例1之方法，得到例示化合物B1 —15之高分子化合物L59g。數平均分子量：21200 [實施例36] 例示化合物B1 —17之製造將實施例1中使用Ν,Ν，一雙[對(9H一咔唑一9-基)苯基]— 1,4 一苯二胺1.3〇g改為使用Ν，Ν'—雙[對(Ν,Ν —二苯基胺基)苯基]〜 9,9 —二辛基一2,7—苐二胺1.93g，除此以外依照實施例1之方法，得到例示化合物B1 —17之高分子化合物L76g。數平均分子量：34800 [實施例37] 例示化合物B1 —18之製造將實施例1中使用Ν，Ν'—雙[對(9H —咔唑一9_基)苯基]〜1ί4 —苯二胺1.3〇g改為使用4,4’一(9Η—亞葬一基)一雙[Ν—{餅 (N，N—二苯基胺基)苯基}苯胺]1.77g，除此以外依照實施例1之方法，得到例示化合物B1 —18之高分子化合物1.63g。 105 200906909 數平均分子量：21100 [實施例38] 例示化合物B1 — 20之製造將實施例1中使用N,1ST—雙[對(9H—°卡唑一9·基)苯基]— 1,4 —苯二胺1.30g改為使用N，N'—雙[對(Ν,Ν—二苯基胺基)苯基]~ 2,6~吡啶二胺1.27g，除此以外依照實施例1之方法，得到例示化合物B1—20之高分子化合物1.36g。數平均分子量：12000 [實施例39]In the same manner as in Example 1, 1.40 g of the polymer compound of the exemplified compound B1-6 was obtained. Number average molecular weight: 23800 [Example 27] Production of exemplified compound B1-7 The hydrazine, bis-bis[p-(9H-carbazole-9-yl)phenylene]-l-phenylenediamine used in Example 1 was used. 1.30g instead of using Ν, Ν, _ bis [p. (ν, ν 〜笨二 ^ ] ] ] 二二二 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5 1.5 ' 依照依照依照依照依照依照依照 ~ ~ ~ ~ ~ ~ ~ High molecular compound l, 51 g. 'Number average molecular weight: 21600 [Example 28] Production of exemplified compound B1-8 The hydrazine, hydrazine, and - bis [p-(9H-carbazole- 9_) was used in Example 1. Benzene 4 phenylene diamine UOg was changed to use hydrazine, hydrazine, a pair [p. (ν, ν~ diphenyl ^ ^ ' 巧 - an anal amine, otherwise in accordance with Example 1; 5 Β 1 - 8 Southern molecular compound i.53g. Number average molecular weight: 14700 [Example 29] Production of exemplified compound B1-9 The N, N, and a pair of [N-(9H-carbazole-9-methicone-benzene) were used in Example 1. The diamine 13Gg was changed to use N,N'-bis[p-(ye~diphenyl)-g-g-103 103 200906909 3,7-dibenzofurandiamine 1.46 g, except the method according to Example i A polymer compound of the exemplified compound B1-9 is obtained. Molecular weight: 28400 [Example 30] The production of the exemplified compound B1-10 will be carried out in Example 1, using N,N'-·double [p-(9H-π卡嗤一 9-yl) stupid]-1,4 ~ ~ stupi diamine 1.3 〇 g was changed to use Ν, Ν 1 - bis [p-(Ν, Ν-diphenylamino)phenyl]-2,8 didibenzothiophene diamine 1.49 g, in addition to the implementation By way of example, 145 g of the polymer compound of the exemplified compound B1-10 was obtained. k Average molecular weight: 16200 - [Example 31] Production of the exemplified compound B1-11 The hydrazine, hydrazine, and a pair of 9H-carbazole-9-yl)phenyl]-; 1,4-phenylenediamine l.3〇g' was changed to use Ν,Ν'-bis[p-(Ν,Ν-diphenylamino)benzene In the same manner as in Example i, 1.50 g of the polymer compound of the exemplified compound B1-11 was obtained. The number average molecular weight: 12300 [Example 32] exemplified compound B1 -12 - The use of Ν, Ν 1 - bis [p-(yang-carbazole-9-yl)phenyl]-1; 4 of the present amine UOg in Example 1 was changed to use 1 ~ (9, 9 - two曱基苐基)—NJST — bis[p-diphenylamino)phenyl]- 3,7-carbazole The polymer compound i.68g of the exemplified compound B1-12 was obtained according to the method of Example 1. The number average molecular weight: 11400 [Example 33] The production of the exemplified compounds B1 to 13 was carried out in Example 1. Using Ν, Ν1—double [p-(9H-flavor-9-yl)phenyl]-丄4~phenylenediamine 1.3〇g was changed to use 4,4,1(1-indenylethylene) pair Further, 1.51 g of the polymer compound of the exemplified compound B1-3 was obtained according to the method of Example 1, except for the method of Example 1 (N-{p-diphenylamino)phenyl}aniline]. Number average molecular weight: 13800 [Example 34] Production of exemplified compound B1-14 The hydrazine, hydrazine, and a pair of [p-(9H-carbazol-9-yl)phenyl]-1,4-benzene were used in Example 1. 1.30 g of the diamine was changed to use 3,3, mono(1-methylethylidene)-bi-β-'-p-diphenylamino)phenyl}phenylamine] 1.51 g, in addition to Example 1 Method '1. Ig of the polymer compound of the exemplified compound B1-14 was obtained. Number average molecular weight: 12900 '[Example 35] • Production of exemplified compound B1-15 The N, N, a pair of [p-(9H-carbazole-9-yl)phenyl]-1,4 was used in Example 1. - phenylenediamine 1.30g instead of 1,1 pair [{N-4 —(4'-N,N-diphenylamino)phenyl}- 4-aminophenyl]cyclohexane 1.6〇 In the same manner as in Example 1, except that the polymer compound L59g of the exemplified compound B1-15 was obtained. Number average molecular weight: 21200 [Example 36] Production of exemplified compound B1-17 The hydrazine, hydrazine, and a pair of [p-(9H-carbazole-9-yl)phenyl]-1,4-benzene were used in Example 1. Diamine 1.3〇g was changed to use Ν,Ν'-bis[p-(Ν,Ν-diphenylamino)phenyl]~ 9,9-dioctyl- 2,7-decanediamine 1.93g, Further, according to the method of Example 1, the polymer compound L76g of the exemplified compound B1-17 was obtained. Number average molecular weight: 34800 [Example 37] Production of exemplified compound B1-18 The hydrazone, Ν'-bis[p-(9H-carbazole-9-yl)phenyl]~1ί4-phenylenediamine used in Example 1 was used. 1.3〇g was changed to use 4,4′-one (9Η-sub-burial one base) a pair of [Ν-{cake (N,N-diphenylamino)phenyl}aniline] 1.77g, in addition to the implementation In the method of Example 1, 1.63 g of the polymer compound of the exemplified compound B1-18 was obtained. 105 200906909 Number average molecular weight: 21100 [Example 38] Production of exemplified compound B1-20 The N,1ST-bis[p-(9H-°carbazol-9)phenyl]-1,4 was used in Example 1. - 1.30 g of phenylenediamine is used instead of 1.27 g of N,N'-bis[p-(indenylhydrazine-diphenylamino)phenyl]~ 2,6-pyridinediamine, except according to Example 1. In the method, 1.36 g of the polymer compound of the exemplified compound B1-20 was obtained. Number average molecular weight: 12,000 [Example 39]

例示化合物B1—21之製造將實施例1中使用N，N'—雙[對(9H—咔唑一9-基)笨基]—1,4 —苯二胺1.30g改為使用N，N' —雙[對(N，N—二苯基胺基)苯基]— 4,4’一二胺基二苯基g同1.49g，除此以外依照實施例1之方法，得到例示化合物B1 — 21之高分子化合物1.46g。數平均分子量：18200 [實施例40] 例示化合物B1 —22之製造將實施例1中使用N，N’一雙[對(9H—咔唑一9-基)笨基]—1，4 -苯二胺UOg改為使用N，N，—雙[對⑽以—二苯基胺基基卜 4,4’一磺醯基雙苯胺i.56g，除此以外依照實施例1之方法，得到例示化合物B1 —22之高分子化合物i.59g。數平均分子量：22000 [實施例41] 例示化合物B2 —2之製造將實施例1中使用Ν,Ν，一雙[對(9H—咔唑—9_基)茉美〗_14 —苯二胺L30g改為使用Ν，Ν’_雙[4〜{4，一ν、ν—土梦基5苯基}苯基]-1,3-苯二胺2‘30g，除此以外3實施Κ 之方法，得到例示化合物Β2-2之高分子化合物2 :、Production of the exemplified compound B1-21 The use of N,N'-bis[p-(9H-carbazole-9-yl)phenyl]-1,4-phenylenediamine 1.30g in Example 1 was changed to N, N An exemplary compound B1 was obtained according to the method of Example 1 except that the bis(p-(N,N-diphenylamino)phenyl]-4,4'-diaminodiphenyl group was the same as 1.49 g. — 21 polymer compound 1.46 g. Number average molecular weight: 18200 [Example 40] Production of exemplified compound B1-22 The N,N'-double [p-(9H-carbazole-9-yl)phenyl]-1,4-benzene was used in Example 1. The diamine UOg was replaced with N,N,-bis[(10)-diphenylaminophenyl 4,4'-sulfonyldiphenylamine i.56g, except that the method of Example 1 was used to obtain an exemplification Polymer compound i.59g of compound B1-22. Number average molecular weight: 22000 [Example 41] Production of exemplified compound B2-2 The hydrazine, hydrazine, and a pair of [p-(9H-carbazole-9-yl)mosamine]_14-phenylenediamine L30g were used in Example 1. In order to use Ν, Ν '_ bis [4 〜 {4, ν, ν - 梦基 5 phenyl} phenyl]-1,3-phenylenediamine 2'30g, in addition to the method of 3, The polymer compound 2 of the exemplified compound Β2-2 was obtained:

數平均分子量：19500 S 106 200906909 [實施例42] 例示化合物B2—15之製造將實施例1中使用N，N’一雙[對(9H —咔唑一9-基)苯基]—1，4 一苯二胺 1.30g 改為使用 1，1 —雙[{N—4 —(4，一N，N—二(4—己基苯基)胺基苯基)苯基}—4 —胺基苯基]環己烧2.64g，除此以外依照實施例1之方法，得到例示化合物B2 —15之高分子化合物2.20g。數平均分子量·‘ 13700 [實施例43] 例示化合物B2 —17之製造Number average molecular weight: 19500 S 106 200906909 [Example 42] Production of exemplified compound B2-15 The N,N'-double [p-(9H-carbazol-9-yl)phenyl]-1 was used in Example 1. 4 1-phenylenediamine 1.30g instead of 1,1 - bis[{N-4-(4,-N,N-bis(4-hexylphenyl)aminophenyl)phenyl}-4-amino A polymer compound of the exemplified compound B2-15 was obtained in an amount of 2.20 g of the compound of the compound B2-15. Number average molecular weight·' 13700 [Example 43] Manufacture of the exemplified compound B2-17

將實施例1中使用N，N’一雙[對(9H —咔唑一9-基)苯基]—1，4 -一苯二胺1.30g改為使用n，N' —雙[4—·^Ν，Ν—二(4—己基苯基) 胺基}苯基笨基]-9,9-二辛基-2,7—苐二胺2.97g，除此以外依照實施例1之方法，得到例示化合物Β2—π之高分子化合物2.34g。數平均分子量：32100 [實施例44] 例示化合物B2—18之製造將實施例1中使用N，N' —雙[對(9H —咔唑一9-基)苯基]—1，4 —苯二胺L3〇g改為使用4,4'一(911 一亞第一9 —基)一雙[N—{4 — (對pN，N—二(4〜己基苯基)胺基)苯基苯基}苯胺]2 81g，除此以外依 -照實施例1之方法，得到例示化合物B2—18之高分子化合物 2.21g。數平均分子量：18600 [實施例45] 例示化合物B3 —2之製造 #將1施例1中使用Ν,Ν，一雙[對(9H—咔唑一9-基)苯基]—1,4 —苯二胺130§改為使用N，Nf —雙[7—{Ν,Ν-二(4—己基苯基)胺 —二曱基—2—第基]—I3 —苯二胺2.47g，除此以外依照貫施例1之方法，得到例示化合物B3 —2之高分子化合物2.03g。數平均分子量：22000 107 200906909 [實施例46] 例示化合物B3 —16之製造In Example 1, N,N'-double [p-(9H-carbazole-9-yl)phenyl]-1,4-phenylenediamine 1.30g was used instead of n, N'-double [4- · Ν, Ν-bis(4-hexylphenyl)amino}phenylphenyl]-9,9-dioctyl-2,7-nonanediamine 2.97 g, except the method according to Example 1 The polymer compound 2.34 g of the exemplified compound Β2-π was obtained. Number average molecular weight: 32100 [Example 44] Production of exemplified compound B2-18 The N,N'-bis[p-(9H-carbazol-9-yl)phenyl]-1,4-benzene was used in Example 1. The diamine L3〇g was changed to use 4,4'-one (911 first sub- 9-base) one pair [N-{4 - (for pN,N-di(4-hexylphenyl)amino)phenyl) Further, according to the method of Example 1, except that phenyl}aniline] 2 81 g, 2.21 g of the polymer compound of the compound B2-18 was obtained. Number average molecular weight: 18600 [Example 45] Manufacture of exemplified compound B3-2 #1 In Example 1, use Ν, Ν, a pair of [p-(9H-carbazole-9-yl)phenyl]-1,4 - phenylenediamine 130 § uses N, Nf - bis [7 - {Ν, Ν-bis(4-hexylphenyl)amine-dimercapto-2-yl)-I3-phenylenediamine 2.47g, Otherwise, according to the method of Example 1, 2.03 g of the polymer compound of the exemplified compound B3-2 was obtained. Number average molecular weight: 22000 107 200906909 [Example 46] Production of exemplified compound B3-16

將實施例1巾個ν,ν’ι[對(9Η—_—9^苯基卜M -苯二胺 1.30g 改為使用 1，1-雙[{N —%一二曱基—7 —(4，—N，N --(4 -己基苯基)胺基）-2、薄基卜4—胺基苯基]環己烧 2.8丄g，除此以外依照實施例1 <方法，得到例示化合物的―10 之兩分子化合物2.33g。數平均分子量：28400 [實施例47]Example 1 towel ν, ν 'ι [p. (9Η-_-9^ Phenyl M-phenylenediamine 1.30g was changed to use 1,1-double [{N-%-didecyl- 7- (4,-N,N-(4-hexylphenyl)amino)-2, thiophenyl 4-aminophenyl]cyclohexane 2.8 丄g, in addition to the method of Example 1 < 2.33 g of a two-molecule compound of -10 of the exemplified compound was obtained. Number average molecular weight: 28,400 [Example 47]

例示化合物B3 —18之製造將實施例1中使用Ν,Ν，一雙[對(9H一咔唑_9_基)苯基]一 1,4 —本二胺 1.30g 改為使用 Ν,Ν1 —雙[9,9一二曱基—7—{Ν,Ν—二(4 —己基苯基）胺基}一 2 —蕹基]—9,9 —二辛基一2,7 —苐二胺 3.14g，除此以外依照實施例1之方法，得到例示化合物Β3_18 之高分子化合物2.71g。數平均分子量：24600 [實施例48] 例示化合物B3 —19之製造將實施例1中使用N，N’一雙[對(9H—η卡。坐一9-基)苯基]一 1，4 . 本一胺1.3〇g改為使用4,4' —(9Η —亞第—9 —基)一雙[N—{9,9 —二甲基一7 — (N，N—二(4 一己基苯基）胺基）一2 —苐基}苯胺]2.98g，除此以外依照實施例1之方法，得到例示化合物B3 — 19之高分子化合物2.47g。數平均分子量：11800 [貫施例49] 例示化合物B4—1之製造將實施例1中使用N，N，一雙[對(9H〜咔唑—9_美)茉其14 ^二胺L30g”使用取，一雙[對(9Hn“—^ 本-知1.26g，除此以外依照實施例丨 <方法，得到例示化合物 108 200906909 B4—1之高分子化合物i.38g。數平均分子量：13500 [實施例50] 例示化合物B4—16之製造將實施例1中使用Ν；ΝΓ一雙[對(9H—咔唑一9_基)笨基]—込4 —苯二胺1.30g改為使用Ν，Ν，-雙[對(9Η—咔唑—9-基)笨— 9,9 —二辛基一2,7〜第二胺i.92g，除此以外依照實施例1之方法，得到例示化合物B4—16之高分子化合物187g。彳數平均分子量：28400 ' [實施例51] .. 例示化合物B4—17之製造將實施例1中使用N，N，一雙[對(阳一咔唑—9_基)笨基]—14 —苯二胺1.3〇g改為使用N，N，-雙[對(3,6〜二己基—9Η:π卡唑二 9-基)苯基]—9,9~二辛基—2,7—蕹二胺2.63g，除此以外依照實施例1之方法’得到例示化合物B4—17之高分子化合物2.32g。數平均分子量：31200 [實施例52] 例示化合物B5-1之製造將實施例1中使用N，N' —雙[對(9H—咔唑一9-基)苯基]—1，4 —苯二胺改為使用Ν,Ν1 —雙[4 —(9Η〜π卡唾基)苯基苯基] 一 1，3 —苯二胺1.58g，除此以外依照實施例丨之方法，得到例示化，合物B5—1之南分子化合物1.44g。數平均分子量：29200 [實施例53] 例示化合物B5 —16之製造將實施例1中使用Ν,Ν’ —雙[對(9H—味。坐—9-基)苯基]—14 —苯二胺1.30g改為使用Ν，Ν' —雙[4 —(9Η〜味唾—9-基)苯基苯基] —9,9_二辛基_2,7—苐二胺2.24g，除此以外依照實施例}之方法，得到例示化合物B5 —16之高分子化合物l 99g。 109 200906909 數平均分子量：24000 [實施例54] 例示化合物B5 — 17之製造將實施例1中使用Ν,Ν' —雙[對(9H—咔唑一9-基)苯基]〜ι，4 一 —胺 1.3〇g 改為使用 Ν,Ν' —雙[4 —(3,6 —二己基一9tl—η卡π坐— 9-基)苯基苯基]-9,9 —二辛基—2,7—葬二胺2.96g，除此以外依照實施例1之方法’得到例示化合物B5 —17之高分子化合物2.57g。數平均分子量：19500 [實施例55] 例示化合物B6—1之製造將實施例1中使用Ν,Ν，一雙[對(9H—咔唑一9-基)苯基]— 1,4 一苯二胺1.30g改為使用ν，Ν，一雙[9,9 — 二曱基一7 — (9l·l — 咔唑一 9-基)一2—第基]—l，3~笨二胺l.75g，除此以外依照實施例l之方法’得到例示化合物Β6—1之高分子化合物1.65g。數平均分子量：21300 [實施例56] 例示化合物B6 —2之製造將實施例1中使用N，N，一雙[對(9H—咔唑一9-基)苯基]—1，4 —苯二胺1.3〇§改為使用1^^ —雙[9,9-二曱基一7-(3,6 —二己基 ’ 一9H—咔唑一9-基)一2-葬基]—1,3—苯二胺2.46g，除此以外依照實施例1之方法，得到例示化合物B6 — 2之高分子化合物2.22g。 '數平均分子量：24800 [實施例57] 例示化合物B6—16之製造將實施例1中使用N，N’一雙[對(9H—咔唑一9-基)苯基]— 1,4 —本一胺1.30g改為使用1,1 —雙[{N〜9,9 —二曱基一7 —(3,6—二己基一 9H—咔唑一 9-基）一2 —第基}一4一胺基苯基]環己烷 2.80g，除此以外依照實施例1之方法，得到例示化合物b6__16 之高分子化合物2.46ίχ。 no 200906909 數平均分子量：21500 [實施例5 8] 例示化合物B6 — 17之製造將實施例1中使用Ν,Ν，—雙[對(9H-咔唑—9-基)苯基卜1,4 一苯二胺1.30g改為使用Ν,Ν’一雙[9,9 —二甲基一7 — (9Η —咔唑〜 9-基)一2—第基卜9,9 —二辛基一2,7-第二胺2.41§，除此以外依照實施例1之方法，得到例示化合物Β6 — 17之高分子化合物 2.10g。數平均分子量：30100 [實施例59] 例示化合物Β6—18之製造將實施例1中使用Ν，Ν，一雙[對(9Η—咔唑一9-基)苯基]一1，4 一苯二胺1.30g改為使用ν，Ν' —雙[9,9-二曱基一7—(3,6 —二己基一9Η—咔唑一9-基）—2—第基]—9,9 —二辛基一2,7 —苐二胺 3.13g，除此以外依照實施例1之方法，得到例示化合物Β6—18 之南分子化合物2.61g。數平均分子量：28500 [實施例60] 例示化合物B6—19之製造將實施例1中使用Ν,Ν，一雙[對(9H—咔唑一9-基)苯基]—1,4 —苯二胺1.30g改為使用4,4’一(9Η—亞苐一9—基)一雙[Ν—{9,9 * —二曱基一 7 —(9H—味嗤一9-基)一2—苐基}苯胺]2.26g，除此以外依照實施例1之方法，得到例示化合物B6—19之高分子化合物 1.98g ° 數平均分子量：19400 [實施例61] 例示化合物C1—20之製造將實施例1中使用N，N'—雙[對(9H—咔唑一9-基)苯基]一 1,4 -苯二胺1.30g改為使用N，N’ -雙[4 — (3 ’ 一Ν,Ν -二(4 —辛基苯基) 111 200906909 胺基苯基)苯基]—1，4—苯二胺2.54g，除此以外依照實施例1之方法，得到例示化合物C1 —20之高分子化合物2.1 lg。數平均分子量：13900 [實施例62] 例示化合物D1 — 5之製造將實施例1中使用Ν,Ν—雙[對(9H—咔唑一9-基)苯基]— 1,4 —笨二胺1.30g改為使用]Sf，N' —雙[4— {4’一Ν—(4—辛基苯基)一ν —(4 —己基苯基)胺基笨氧基}笨基]—1，4 —笨二胺2,49g，除此以外依照貫施例1之方法，得到例示化合物D1 — 5之高分子化合物 -2.20g 〇 -數平均分子量：31000 [實施例63] 例示化合物D1 —6之製造 #將實施例1中使用Ν,Ν，一雙[對(9H—咔唑一9-基)苯基]一1,4 ~笨二胺1.30g改為使用ν，Ν’一雙[4—{4，一Ν—苯基—ν—(1 —萘基)胺基苯氧基}苯基]—I,4〜笨二胺j 8?g，除此以外依照實施例！之方法，得到例示化合物Dl〜6之高分子化合物177g。數平均分子量：24500 [實施例64] 例示化合物D1 — 7之製造 —將實施例1中使用N，N，〜雙[對(9H —咔唑一9-基)苯基]一 1,4 〜笨二胺1.3〇g改為使用ν,Ν，一雙[4一{4'一N—苯基—(2—萘基)¾基本氧基}苯基]—1，4〜笨二胺i.87g，除此以外依照實施例丄方法，得到例示化合物之高分子化合物169g。婁文平均分子量：24100 [實施例65] 例示化合物E1—6之製造〜將實施例1中使用Ν，：ΝΓ~~雙[對(9H—咔唑一9-基)苯基]一 1,4 —笨二胺1.3〇g改為使用ν，Ν'〜雙[4—{4,一Ν — (4—辛基苯基)一Ν 112 200906909 —(4 —己基本基♦基本氧基}本基]—1，5~~萘二胺2.6〇g，除此以外依照實施例1之方法，得到例示化合物El —6之高分子化厶物 2.31g。 σ 數平均分子量：25000 [實施例66] 例示化合物Gl —1之製造將實施例1中使用Ν,Ν，一雙[對(9Η〜咔唑一9-基)笨基j —Manufacture of the exemplified compound B3-18. In Example 1, the use of hydrazine, hydrazine, a pair of [p-(9H-carbazole-9-yl)phenyl]-1,4-indiamine 1.30g was used instead of hydrazine, Ν1 —双[9,9-二曱基-7-{Ν,Ν-bis(4-hexylphenyl)amino}}2-indenyl]-9,9-dioctyl-2,7-苐2 In the same manner as in Example 1, except that the amine was 3.14 g, 2.71 g of the polymer compound of the exemplified compound Β3_18 was obtained. Number average molecular weight: 24600 [Example 48] Production of exemplified compound B3-19 The N,N'-double [p-(9H-η卡. sit- 9-yl)phenyl]-1,4 was used in Example 1. The original amine 1.3〇g is changed to use 4,4'-(9Η-亚第第9-基) a pair [N-{9,9-dimethyl-7-(N,N-two (4 one) Further, according to the method of Example 1, 2.87 g of the polymer compound of the exemplified compound B3-19 was obtained, except that hexylphenyl)amino)amino-2-indenyl}aniline] was 2.98 g. Number average molecular weight: 11800 [Scheme 49] Manufacture of the exemplified compound B4-1 to use N, N, a pair of [Examples (9H~carbazole-9-meth)mosa 14^diamine L30g" Using the same, a pair of [9Hn"-^--- 1.26g, except the method of the example 丨 < method, the polymer compound i.38g of the exemplified compound 108 200906909 B4-1 was obtained. Number average molecular weight: 13500 [Example 50] Production of exemplified compound B4-16 The hydrazine used in Example 1; hydrazine-bis[((9H-carbazole-9-yl))]-phenylene-phenylenediamine 1.30g was used instead. Ν, Ν, - bis [p-(9Η-carbazole-9-yl) stupid-9,9-dioctyl-2,7~2~2, i.92g, except the method of Example 1, The polymer compound 187g of the compound B4-16 is exemplified. The number average molecular weight of the compound B14-16: 28400 ' [Example 51] .. Production of the exemplified compound B4-17 The N, N, and a pair of the use of Example 1 [Yang (Yang Yiqi) Azo- 9-yl) stupyl]- 14-phenylenediamine 1.3〇g is replaced by N,N,-bis [p-(3,6-dihexyl-9):pyrazoledi-9-yl)phenyl] —9,9~dioctyl-2,7-decanediamine 2.63 g, in addition to The method of Example 1 gave 2.32 g of the polymer compound of the exemplified compound B4-17. Number average molecular weight: 31200 [Example 52] Production of the exemplified compound B5-1 The N, N'-double [pair] used in Example 1 (9H-carbazole-9-yl)phenyl]-1,4-phenylenediamine was changed to use hydrazine, hydrazine 1 - bis[4 -(9 Η~π carbyl)phenylphenyl]-1,3 — In the same manner as in Example 丨, 1.44 g of the south molecular compound of the compound B5-1 was obtained, except that 1.58 g of phenylenediamine was obtained. Number average molecular weight: 29200 [Example 53] Production of the exemplified compound B5-16 In Example 1, Ν, Ν'-double [p. (9H-flavor. sit-9-yl) phenyl]-14-phenylenediamine 1.30g was used instead of Ν, Ν'-double [4 - (9Η~ A polymer of the exemplified compound B5-16 was obtained according to the method of Example} except that 2.14 g of salicyl-9-yl)phenylphenyl]-9,9-dioctyl-2,7-nonanediamine was used. Compound l 99 g. 109 200906909 Number average molecular weight: 24000 [Example 54] Production of exemplified compound B5-17 The hydrazine, Ν'-bis[p-(9H-carbazole-9-yl)phenyl group] used in Example 1 was used. ~ι,4 一—amine 1.3〇g For the use of Ν, Ν'-double [4 - (3,6-dihexyl-9tl-η卡π坐-9-yl)phenylphenyl]-9,9-dioctyl-2,7-buried two 2.57 g of the polymer compound of the exemplified compound B5-17 was obtained in the same manner as in Example 1 except that the amine was 2.96 g. Number average molecular weight: 19500 [Example 55] Production of exemplified compound B6-1 The hydrazine, hydrazine, and a pair of [p-(9H-carbazol-9-yl)phenyl]-1,4-benzene were used in Example 1. 1.30g of diamine is changed to use ν, Ν, a pair of [9,9-dimercapto-7-(9l·l-carbazole-9-yl)- 2-yl]-l, 3~ stupidiamine Further, 1.75 g of the polymer compound exemplified as the compound Β6-1 was obtained according to the method of Example 1 except for the procedure of Example 1. Number average molecular weight: 21300 [Example 56] Production of exemplified compound B6-2 N, N, a pair of [p-(9H-carbazole-9-yl)phenyl]-1,4-benzene was used in Example 1. Diamine 1.3〇§ Use 1^^-bis[9,9-dimercapto-7-(3,6-dihexyl'- 9H-carbazole-9-yl)- 2-burial]-1 Further, according to the method of Example 1, 2.22 g of the polymer compound of the exemplified compound B6-2 was obtained, except that 2.46 g of 3-phenylenediamine was used. 'Number average molecular weight: 24,800 [Example 57] Production of exemplified compound B6-16 The N,N'-double [p-(9H-carbazol-9-yl)phenyl]-1,4- was used in Example 1. 1.1g of the present amine is changed to 1,1 - double [{N~9,9-dimercapto- 7-(3,6-dihexyl- 9H-carbazole-9-yl)- 2 -diyl} A polymer compound of the exemplified compound b6__16, 2.46 χ, was obtained according to the method of Example 1 except that 2.80 g of 4-aminophenyl]cyclohexane was used. No 200906909 Number average molecular weight: 21500 [Example 5 8] Production of exemplified compound B6-17 The hydrazine, hydrazine, and bis[[(9H-carbazole-9-yl)phenyl) 1,4 were used in Example 1. 1.30g of monophenylenediamine is used instead of Ν, Ν 'a pair of [9,9-dimethyl-7-(9Η-carbazole~9-yl)- 2-diylbu 9,9-dioctyl- The polymer compound 2.10 g of the exemplified compound Β6-17 was obtained according to the method of Example 1 except for the 2,7-second amine. Number average molecular weight: 30100 [Example 59] Production of exemplified compound Β6-18 The hydrazine, hydrazine, and a pair of [p-(9-oxindole-9-yl)phenyl]-1,4-benzene were used in Example 1. 1.30g of diamine is changed to use ν,Ν'-bis[9,9-dimercapto-7-(3,6-dihexyl- 9-oxindole-9-yl)-2-yl]-9, In the same manner as in Example 1 except that 9-dioctyl-2,7-nonanediamine was 3.13 g, 2.61 g of the mp. Number average molecular weight: 28500 [Example 60] Production of exemplified compound B6-19 The hydrazine, hydrazine, and a pair of [p-(9H-carbazol-9-yl)phenyl]-1,4-benzene were used in Example 1. 1.30g of diamine is changed to 4,4'-(9Η-Aachen-9-yl)-double [Ν-{9,9*-dimercapto- 7-(9H- miso-9-yl) The polymer compound of the exemplified compound B6-19 was obtained according to the method of Example 1 except that 2-mercapto}aniline] 2.26 g was obtained. 1.98 g ° number average molecular weight: 19400 [Example 61] Manufacture of the exemplified compound C1-20 In Example 1, N,N'-bis[p-(9H-carbazole-9-yl)phenyl]-1,4-diphenyldiamine 1.30g was used instead of N,N'-bis[4—( An example compound was obtained according to the method of Example 1 except that 3'-anthracene, bis-(4-octylphenyl) 111 200906909 aminophenyl)phenyl]-1,4-phenylenediamine 2.54 g Polymer compound 2.1 lg of C1-20. Number average molecular weight: 13900 [Example 62] Production of the exemplified compound D1 - 5 The hydrazine, hydrazine-bis[p-(9H-carbazole-9-yl)phenyl]-1,4-stuppy was used in Example 1. 1.30g of amine was changed to use]Sf,N'-bis[4-{4'-indolyl-(4-octylphenyl)- ν-(4-hexylphenyl)aminophenyloxy]styl]- 1,4 - 2,49 g of the stilbene diamine, except the method of Example 1, the polymer compound of the exemplified compound D1 - 5 - 2.20 g 〇 - number average molecular weight: 31000 [Example 63] exemplified compound D1 Manufacture of -6. In Example 1, Ν, Ν, a pair of [p-(9H-carbazole-9-yl)phenyl]-1,4-diphenylamine 1.30g was used instead of ν, Ν' Bis [4-{4, fluorenyl-phenyl-v-(1-naphthyl)aminophenoxy}phenyl]-I,4~stupolediamine j 8?g, in addition to the examples! By the method, 177 g of the polymer compound of the exemplified compounds D1 to 6 was obtained. Number average molecular weight: 24,500 [Example 64] Manufacture of the exemplified compound D1-7 - N, N, ~ bis [p-(9H-carbazol-9-yl)phenyl]-1,4~ was used in Example 1. The stupid diamine 1.3〇g is changed to use ν, Ν, a pair of [4-{4'-N-phenyl-(2-naphthyl) 3⁄4 basic oxy}phenyl]-1,4~ stupid diamine i In the same manner as in Example 丄, 169 g of the polymer compound of the exemplified compound was obtained. Dimensional average molecular weight: 24100 [Example 65] Manufacture of the exemplified compound E1-6 - The hydrazine used in Example 1 was: ΝΓ~~bis[p-(9H-carbazole-9-yl)phenyl]-1, 4 - stupid diamine 1.3 〇 g changed to use ν, Ν '~ double [4 - {4, a Ν - (4-octyl phenyl) a Ν 112 200906909 — (4 — hexane basic ♦ basic oxy} In the same manner as in Example 1, 2.31 g of the polymerized anthracene of the exemplified compound El-6 was obtained in the same manner as in Example 1. The average molecular weight of σ number: 25,000 [Examples] 66] Production of exemplified compound G1-1 The use of hydrazine, hydrazine, and a pair of [in the case of (9 Η~ carbazole-9-yl) stupid j-

~苯二胺1.30g改為使用N，N’一雙[4—{4'—N，N—二苯基胺基苯基硫}笨基]一1，4 —苯二胺1.72g，除此以外依照實施例！之方法，得到例示化合物G1 — 1之局分子化合物i.6gg。 -數平均分子量：16200 [實施例67] 一含有磺基之高分子化合物之製造，其中，高分子鏈中，具例不化合物A1 — 1所示重複單位中之苯環至少丨個經磺基取^ 複單位至少1個一將高分子鏈中具有至少1個實施例丨得到例示化合物八1 — 1 所不重複單位的高分子化合物135g溶於氯仿43Jg，於氮 =，裝入98%硫酸20g，於室温攪拌h5小時。將反應液倒至【 ^2〇(ω，滤取析出物。將得到之固體以乙腈洗;條至濾 ’於70度進行8小時減壓乾燥，得到粗產物157g褐色固^ =物1.57g溶於50%甲醇水9〇ml，加入陰離子交換樹脂(_ 二二，AmberliteIRA400 —〇HAG)160ml，於室溫攪拌 5 小時。 =交換樹賴去後，使濾液濃縮個，於7G度進行7小题 ^。將得狀固體溶於曱醇3〇ml，以？苯8〇ml使再沈蹲成 j目的化合物1.5lg褐色固體。該化合物溶於甲醇，不溶於二冉者、該化合物於溶液狀態未觀察到凝集性。又，^一重複單位之平均磺基數從下述計算式計算。平均續基數={(例示化合物A1 —”之重複單位分子 ^刀析値(％)-(例示化合物Ai — D之重複單位中之硫數\疏原= 113 200906909 =〇〇}+{硫原子量增G —硫缝分析値(％)χ(縣分子量—氣原硫元素分析値13.6% 每一重複單位之平均磺基數：5.3個 UV(Imax) ： 341nm(MeOH) [實施例68] 含有續基之高分子化合物之製造，其中，高分子鏈中示化合物A1-3所示重複單位巾之苯環至少丨個經钱取之' 複單位至少1個重1. benzenediamine 1.30g was changed to use N, N'-double [4-{4'-N,N-diphenylaminophenylsulfinyl]phenyl]-1,4-phenylenediamine 1.72g, Other than this in accordance with the embodiment! In the method, the molecular compound i.6gg of the compound G1-1 is exemplified. - number average molecular weight: 16200 [Example 67] Production of a polymer compound containing a sulfo group, wherein, in the polymer chain, at least one sulfo group in the repeating unit represented by the compound A11-1 135 g of a polymer compound having at least one of the polymer chains having at least one of the examples obtained in the polymer chain to obtain the exemplified compound VIII 1 - 1 non-repeating unit is dissolved in 43 g of chloroform, and nitrogen is added to 98% sulfuric acid. 20 g, stirred at room temperature for 5 hours. The reaction solution was poured to [^2 〇 (ω, the precipitate was collected by filtration. The obtained solid was washed with acetonitrile; and the mixture was filtered and dried at 70 deg. for 8 hours under reduced pressure to give crude product 157 g brown solid = 1.57 g Dissolve in 9 〇ml of 50% methanol water, add 160 ml of anion exchange resin (_2, Amberlite IRA400 - 〇HAG), stir at room temperature for 5 hours. = After the exchange tree is removed, the filtrate is concentrated and 7 at 7G. Substance ^. Dissolve the solid in 3 〇ml of decyl alcohol, and then re-sink into a brown solid of 1.5 g of the compound of benzene. The compound is soluble in methanol, insoluble in diterpene, the compound is No agglutination was observed in the solution state. Further, the average number of sulfo groups in the repeating unit was calculated from the following formula: Average number of repeating groups = {(exemplified compound A1 -" repeating unit molecule ^ 値値 (%) - (exemplary compound Ai - the number of sulfur in the repeat unit of D / sparse = 113 200906909 = 〇〇} + { sulfur atomic weight increase G - sulfur seam analysis 値 (%) χ (county molecular weight - gas elemental sulfur element analysis 値 13.6% each repeat Average sulfo number per unit: 5.3 UV (Imax): 341 nm (MeOH) [Example 68] High score with retentate Manufacturing of the compound, wherein the compound shown in the polymer chain repeating units of the towel take the phenyl ring by at least one money Shu A1-3 'units of at least one complex weight

將實補67巾制實補丨得狀例示化合物M —丨之高八 -子化合物l_35g改為使用實施例2得到之例示化合物八丨―3 分子化合物1.35g，除此以外，進行實施例67記載之操作，= 目的高分子化合物1.60g。又基數，依據實施例67記載之方法，計算每一重複單位之平均磺每一重複單位之平均磺基數：3 5個 [實施例69]In the case of the actual compound 67, the compound exemplified as the exemplified compound M- 丨八八八～～～～～～～～～～～～ The operation described is = 1.60 g of the target polymer compound. Further, based on the method described in Example 67, the average sulfo number per repeat unit of each repeat unit was calculated: 3 5 [Example 69]

含有磺基之高分子化合物之製造，其中，高分子鏈中，具例示化合物A1 —10所示重複單位中之苯環至少丨個經磺基取代^重，複單位至少1個將實施例67中使用實施例1得到之例示化合物Α1 — ι之高分，子化合物1.35g改為使用實施例7得到之例示化合物A1 —1〇之高分子化合物1.35g，除此以外進行實施例67記載之操作，得到目的高分子化合物1.5lg。又’依據實施例67記載之方法，計算每一重複單位之平均石薔基數。 ” 每一重複單位之平均磺基數：5.5個 [實施例70] 含有磺基之高分子化合物之製造，其中，高分子鏈中，具例 114 200906909 示化合物Al —11所示重複單位中之苯環至少1個經石黃基取代之重複單位至少1個將實施例67中使用實施例1得到之例示化合物Α1 — ι之高分子化合物l_35g改為使用實施例8得到之例示化合物Ai —η之高分子化合物1.35g，除此以外進行實施例67記載之操作，得到目的南分子化合物1.57g。又，依據實施例67記載之方法，計算每一重複單位之平均磺基數。每一重複單位之平均磺基數：5.9個 [實施例71] 含有磺基之尚分子化合物之製造，其中，高分子鏈中，具例示化合物A1 —13所示重複單位中之苯環至少丨個經磺基取代之複單位至少1個將實施例67中使用實施例1得到之例示化合物Α1 — ι之高分子化合物1.35g改為使用實施例1〇得到之例示化合物A1 —13 2 高分子化合物1.35g，除此以外進行實施例67記載之操作，得到目的高分子化合物1.58g。某婁又，依據實施例67記載之方法，計算每一重複單位之平均碏每一重複單位之平均磺基數：6.0個 [實施例72] 一含有磺基之高分子化合物之製造，其中，高分子鏈中，具例示化合物A1 —17所示重複單位中之苯環至少丨個經磺基取複單位至少1個 ~ s 將實施例67中使用實施例1得到之例示化合物Ai — 丨之高分子化合物1.35g改為使用實施例13得到之例示化合物之高分子化合物1.35g，除此以外進行實施例67記載之操作目的之高分子化合物1.43g。 f 1 又，依據實施例67記載之方法，計算每一重複單位之平均碏 115 200906909 基數。每一重複單位之平均磺基數：4.9個 [實施例73] 含有磺基之高分子化合物之製造，其中，高分子鏈中，具例示化合物A2 —6所示重複單位中之苯環至少丨個經碏基取^ 複單位至少1個將貫施例67中使用實施例1得到之例示化合物八丨—丨之高分子化合物1.35g改為使用實施例16得到之例示化合物A2 —6之高分子化合物1.35g，除此以外進行實施例67記載之操作，得= 的之高分子化合物1.49g。、又，依據實施例67記載之方法，計算每一重複單位之平均碏基數。每一重複單位之平均磺基數：5.2個 [實施例74] _含有磺基之高分子化合物之製造，其中，高分子鏈中，具例示化合物A2 —7所示重複單位中之苯環至少丨個經磺基取代之複單位至少1個將貫施例67中使用實施例1得到之例示化合物A1 — 1之高分子化合物1.35g改為使用實施例17得到之例示化合物A2 —7之高，分子化合物1.35g ’除此以外進行實施例67記載之操作，得到= 的之高分子化合物1.47g。，又，依據實施例67記載之方法，計算每一重複單位之平均碏基數。 < 每一重複單位之平均磺基數：5.1個 [實施例75] 含有磺基之高分子化合物之製造，其中，高分子鏈中，具例示化合物A3 —1所示重複單位中之苯環至少1個經磺基取代之重複單位至少1個將實施例67中使用實施例1得到之例示化合物A1 — 1之高分 116 200906909 子化合物1.35g改為使用實施例18得到之例示化合物A3 —丨之高分子化合物1.35g，除此以外進行實施例67記載之操作，= 的之馬分子化合物1.44g。、又’依據貝施例67 §己載之方法，計异每一重複單位之平均磺基數。 ” 每一重複單位之平均磺基數：4.7個 [實施例76] 一含有磺基之高分子化合物之製造，其中，高分子鏈中，具例不化合物A3 —4所示重複單位中之苯環至少1個經磺基取代 '複單位至少1個將實施例67中使用實施例1得到之例示化合物Ai — i之高分子化合物1.35g改為使用實施例2〇得到之例示化合物A3 —4之高分子化合物1.35g ’除此以外進行實施例67記載之操作，得到目的之尚分子化合物1.55g。又，依據實施例67記載之方法，計算每一重複單位之平均石基基數。每一重複單位之平均磺基數：5.0個 [實施例77] 一含有磺基之高分子化合物之製造，其中，高分子鏈中，具例示化合物B1 — 6所示重複單位中之苯環至少1個經磺基取代之重複單位至少1個將實施例67中使用實施例1得到之例示化合物A1 — 1之高分子化合物1.35g改為使用實施例％得到之例示化合物B1 —6之高分子化合物1.35g，除此以外進行實施例67記載之操作，得到目的之局分子化合物1.46g。又，依據實施例67記載之方法，計算每一重複單位之平均石备基數。每一重複單位之平均磺基數：5 〇個 [實施例78] 117 200906909 含有磺基之1¾分子化合物之製造，其中’南分子鍵中’具例示化合物B1—9所示重複單位中之苯環至少1個經續基取代之重複單位至少1個將實施例67中使用實施例1得到之例示化合物A1 — 1之高分子化合物1.35g改為使用實施例29得到之例示化合物B1 —9之高分子化合物1.35g，除此以外進行實施例67記載之操作，得到目的之高分子化合物1.46g。又，依據實施例67記載之方法，計算每一重複單位之平均磺基數。每一重複單位之平均磺基數：4.9個 [實施例79] 含有磺基之高分子化合物之製造，其中，高分子鏈中，具例示化合物B1 — 12所示重複單位中之苯環至少1個經磺基取代之重複單位至少1個將實施例67中使用實施例1得到之例示化合物A1 — 1之高分子化合物1.35g改為使用實施例32得到之例示化合物B1 — 12之高分子化合物1.35g ’除此以外進行實施例67記載之操作，得到目的之高分子化合物1.67g。又，依據實施例67記載之方法，計算每一重複單位之平均石黃基數。每一重複單位之平均磺基數：6.2個 [實施例80] 含有石黃基之高分子化合物之製造，其中’高分子鏈中，具例示化合物B1 — 13所示重複單位中之苯環至少1個經磺基取代之重複單位至少1個將實施例67中使用實施例1得到之例示化合物八丨―〗之高分 ^化合物1.35g改為使用實施例33得到之例示化合物—13之高分子化合物1.35g，除此以外進行實施例67記載之操作，得到目的之南分子化合物1.5〇g。 118 200906909 又，依據實施例67記載之方法，計算每一重複單位之平均磺基數。每一重複單位之平均磺基數：5.2個 [實施例81] 含有石黃基之南分子化合物之製造，其中’南分子鍵中，具例示化合物B1 —14所示重複單位中之苯環至少1個經磺基取代之重複單位至少1個The production of a polymer compound containing a sulfo group, wherein, in the polymer chain, at least one of the benzene rings in the repeating unit represented by the exemplified compound A1-10 is substituted by a sulfo group, and at least one compound unit is used. The exemplified compound Α1 - ι high score obtained in Example 1 was used, and the sub-compound 1.35 g was replaced with the polymer compound 1.35 g of the exemplified compound A1 -1 oxime obtained in Example 7, except that the case described in Example 67 was carried out. The operation was carried out to obtain 1.5 g of the objective polymer compound. Further, the average number of sarcophagi of each repeating unit was calculated in accordance with the method described in Example 67. The average number of sulfo groups per repeating unit: 5.5 [Example 70] The production of a polymer compound containing a sulfo group, wherein, in the polymer chain, a compound of the formula 114 200906909 shows a benzene in a repeating unit represented by the compound Al-11 At least one repeating unit substituted with at least one rhizome-based ring, the polymer compound l_35g of the exemplified compound Α1 -1 obtained in Example 67 in Example 67 was changed to the exemplified compound Ai-η obtained in Example 8. The procedure described in Example 67 was carried out, except that 1.35 g of the polymer compound was obtained, to obtain 1.57 g of the objective molecular compound. The average number of sulfo groups per repeat unit was calculated according to the method described in Example 67. The average number of sulfo groups: 5.9 [Example 71] The production of a molecular compound containing a sulfo group, wherein, in the polymer chain, at least one of the benzene rings in the repeating unit represented by the exemplified compound A1-13 is substituted with a sulfo group. At least one of the compound units of Example 67 used in Example 67 was replaced with the exemplified compound A1 obtained in Example 1 using the polymer compound 1.35 g of the exemplified compound Α1 -1 obtained in Example 1. In the same manner as described in Example 67, except that 1.35 g of a polymer compound was used, the desired polymer compound was obtained in an amount of 1.58 g. Further, according to the method described in Example 67, the average of each repeating unit was calculated. The average number of sulfo groups in the repeating unit: 6.0 [Example 72] The production of a polymer compound containing a sulfo group, wherein, in the polymer chain, at least one of the benzene rings in the repeating unit represented by the exemplified compound A1-17 The sulfo group is at least one unit of s. In the example 67, the polymer compound 1.5g of the exemplified compound Ai- oxime obtained in Example 1 is used instead of the polymer compound 1.35g of the exemplified compound obtained in Example 13, except Further, 1.43 g of the polymer compound of the operation object described in Example 67 was carried out. f 1 Further, the average 碏115 200906909 base number of each repeating unit was calculated according to the method described in Example 67. The average number of sulfo groups per repeating unit: 4.9 [Example 73] The production of a polymer compound containing a sulfo group, wherein, in the polymer chain, the benzene ring in the repeating unit represented by the exemplified compound A2-6 is at least At least one of the thiol-based compounding units is used in Example 67, and the polymer compound 1.35g of the exemplified compound octagonal-indole obtained in Example 1 is used instead of the exemplified compound A2-6 obtained in Example 16. The procedure described in Example 67 was carried out, except that 1.35 g of the molecular compound was obtained, and 1.49 g of the polymer compound of = was obtained. Further, the average number of fluorenyl groups per repeat unit was calculated according to the method described in Example 67. The average number of sulfo groups per unit: 5.2 [Example 74] _ Manufacture of a polymer compound containing a sulfo group, wherein, in the polymer chain, at least one benzene ring in the repeating unit represented by the exemplified compound A2-7 At least one of the complex units of the base substitution is 1.35 g of the polymer compound exemplified in Example 67 using the exemplified compound A1-1 obtained in Example 1, and the molecular compound 1.35 is used instead of the exemplified compound A2-7 obtained in Example 17. The operation described in Example 67 was carried out, and 1.47 g of a polymer compound of ? was obtained. Further, the average enthalpy number of each repeating unit was calculated in accordance with the method described in Example 67. < The average number of sulfo groups per repeating unit: 5.1 [Example 75] The production of a polymer compound containing a sulfo group, wherein, in the polymer chain, the benzene ring in the repeating unit represented by the exemplified compound A3-1 is at least At least one repeating unit substituted with a sulfo group. The high score 116 of the exemplified compound A1 -1 obtained in Example 67 in Example 67 was changed to the compound of the formula A3 - 得到 obtained by using Example 18 The procedure described in Example 67 was carried out, except that 1.35 g of the polymer compound was used, and 1.44 g of the compound of the horse was determined. And, according to the method of Bayesian 67 §, the average number of sulfo groups per repeat unit is calculated. The average number of sulfo groups per repeating unit: 4.7 [Example 76] The production of a polymer compound containing a sulfo group, wherein, in the polymer chain, the benzene ring in the repeating unit represented by the compound A3-4 At least one sulfonyl substituted 'complex unit at least one of the polymer compound 1.5g of the exemplified compound Ai-i obtained in Example 67 used in Example 67 was changed to the exemplified compound A3-4 obtained in Example 2 The polymer compound 1.35 g was subjected to the operation described in Example 67 to obtain 1.55 g of the desired molecular compound. The average stone base number per repeat unit was calculated according to the method described in Example 67. The average number of sulfo groups per unit: 5.0 [Example 77] The production of a polymer compound containing a sulfo group, wherein, in the polymer chain, at least one benzene ring in the repeating unit represented by the exemplified compound B1-6 is sulfonated. The repeating unit of the radical substitution is at least one. The high molecular compound 1.35g of the exemplified compound A1-1 obtained in Example 67 in Example 67 is changed to the height of the exemplified compound B1-6 obtained by using the example %. The procedure described in Example 67 was carried out, except that 1.35 g of the molecular compound was obtained, to obtain 1.46 g of the desired molecular compound. Further, the average number of bases per repeat unit was calculated according to the method described in Example 67. The average number of sulfo groups: 5 〇 [Example 78] 117 200906909 The manufacture of a 13⁄4 molecular compound containing a sulfo group, wherein the 'Southern molecular bond' has at least one benzene ring in the repeating unit represented by the exemplified compound B1-9 At least one repeating unit of the hydrazine-substituted compound 1.35 g of the polymer compound exemplified in Example 67 using the exemplified compound A1 -1 obtained in Example 1 was changed to the polymer compound 1.35 g of the exemplified compound B1-9 obtained in Example 29. The procedure described in Example 67 was carried out to obtain 1.46 g of the desired polymer compound. The average number of sulfo groups per repeating unit was calculated according to the method described in Example 67. The average number of sulfo groups per repeating unit: 4.9 [Example 79] Production of a polymer compound containing a sulfo group, wherein, in the polymer chain, benzene in a repeating unit represented by the compound B1-12 is exemplified At least one repeating unit having at least one sulfo group substituted in the ring. 1.35 g of the polymer compound exemplified in Example 67 using the exemplified compound A1 -1 obtained in Example 1 was changed to the exemplified compound B1-12 obtained in Example 32. The polymer compound 1.35 g was subjected to the operation described in Example 67 to obtain 1.67 g of the intended polymer compound. The average number of the base of each repeating unit was calculated according to the method described in Example 67. The average number of sulfo groups per unit: 6.2 [Example 80] The production of a polymer compound containing a diphthyl group, wherein in the polymer chain, at least one benzene ring in the repeating unit represented by the exemplified compound B1-13 is sulfonated. The repeating unit of the radical substitution is at least one. The high molecular weight compound 1.35g of the exemplified compound obtained in Example 67 used in Example 67 is changed to the polymer compound 1.35 g of the exemplified compound 13 obtained in Example 33. The operation described in Example 67 was carried out, and 1.5 g of the desired molecular compound of the south was obtained. 118 200906909 Further, the average number of sulfonic groups per repeating unit was calculated in accordance with the method described in Example 67. The average number of sulfo groups per repeating unit: 5.2 [Example 81] The manufacture of a south molecular compound containing a Schistosyl group, wherein the 'Southern molecular bond has at least one benzene ring in the repeating unit represented by the exemplified compound B1-14 At least 1 repeating unit substituted by sulfo group

將實施例67中使用實施例1得到之例示化合物A1 — 1之高分子化合物1.35g改為使用實施例34得到之例示化合物B1 —14之高分子化合物1.35g，除此以外進行實施例67記載之操作，得到目的之高分子化合物1.51g。又，依據實施例67記載之方法，計算每一重複單位之平均碏基數。一每一重複單位之平均磺基數：5.3個 [實施例82] 含有磺基之高分子化合物之製造，其中，高分子鏈中，具例示化合物B1 — 15所示重複單位中之苯環至少丨個經磺基取^ 複單位至少1個In the example 67, 1.35 g of the polymer compound of the exemplified compound A1 - 1 obtained in Example 1 was used instead of the polymer compound 1.35 g of the exemplified compound B1-14 obtained in Example 34, except that the case of Example 67 was described. The operation was carried out to obtain 1.51 g of a desired polymer compound. Further, according to the method described in Example 67, the average enthalpy number of each repeating unit was calculated. The average number of sulfo groups per repeating unit: 5.3 [Example 82] The production of a polymer compound containing a sulfo group, wherein, in the polymer chain, the benzene ring in the repeating unit represented by the exemplified compound B1-15 is at least 丨At least 1 unit of sulfo group

將實施例67中使用實施例1得到之例示化合物A1 —丨之高分子化合物1.35g改為使用實施例35得到之例示化合物 —高分子化合物1.35g，除此以外進行實施例67記載之操作，目的之高分子化合物丨52g。 ' J 又’依據實施例67記載之方法，計算每一重複單位之平均石黃每一重複單位之平均磺基數：5.4個 [實施例83] 含有續基之高分子化合物之製造，其中，高分子鍵中，呈巧合物m-重複單位中之笨縣少^ 複單位至少1個土％代之重 119 200906909 將貫施例67中使用實施例1得到之例示化合物Αι — 1古子化合物1.35g改為使用實施例37得狀例示化合物= 南分子化合物1.35g ’除此以外進行實施例67記載目的之高分子化合物1.60g。 ’ 件到基數，依據實施例67記載之方法，計算每—重複單位之平均错每一重複單位之平均磺基數：6J個 [實施例84]The procedure described in Example 67 was carried out except that 1.35 g of the polymer compound 1-1 of the exemplified compound A1 obtained in Example 1 was used instead of the exemplified compound obtained in Example 35, the polymer compound 1.35 g. The target polymer compound 丨52g. 'J again', according to the method described in Example 67, the average number of sulfo groups per repeat unit of each repeating unit was calculated: 5.4 [Example 83] Production of a polymer compound containing a recurring group, wherein, Among the molecular bonds, it is a clever compound in the m-repeat unit. The stupid county is less than the compound unit. At least one soil % is replaced by the weight 119. 200906909 The exemplified compound obtained in Example 1 using Example 1 is —ι-1 ancient compound 1.35. In the same manner as in Example 37, except that the compound of Example 37 was used, 1.60 g of the polymer compound of the object described in Example 67 was used. From the piece to the base number, the average error per unit of repeating unit was calculated according to the method described in Example 67: the average number of sulfo groups per repeating unit: 6 J [Example 84]

含有磺基之高分子化合物之製造，其中，高分子鏈中，且 -示化合物B4—1所示重複單位中之苯環至少〗個經碏基二二複單位至少1個 ^重將實施例67中使用實施例1得到之例示化合物Al — i之高分子化合物1.35g改為使用實施例49得到之例示化合物1 ^古分子化合物1.35g，除此以外進行實施例67記載之操作，得= 的之而分子化合物1.44g。又，依據實施例67記載之方法，計算每一重複單位之平均碚基數。〃每一重複單位之平均磺基數：4.9個 [實施例85] 含有石黃基之咼分子化合物之製造，其中’高分子鏈中，具例 •-示化合物D1—6所示重複單位中之苯環至少1個經磺基取代之，複單位至少1個將實施例67中使用實施例1得到之例示化合物Al ~ 1之高分子化合物1.35g改為使用實施例63得到之例示化合物di — 6之高分子化合物1.35g，除此以外進行實施例67記載之操作，得到目的之焉分子化合物1.49g。又，依據實施例67記載之方法，計算每一重複單位之平均供基數。貝每一重複單位之平均磺基數：5.2個 120 200906909 [實施例86] 一含有磺基之高分子化合物之製造，其中，高分子鏈中，具例示化合物D1 —7所示重複單位中之苯環至少1個經磺基取代複單位至少1個〃皇將貫施例67中使用實施例1得到之例示化合物A1 — 1之高分子化合物1.35g改為使用實施例64得到之例示化合物di —7 分子^合物1.35g，除此以外進行實施例67記載之操作，得到= 的之咼分子化合物1.51g。又，依據實施例67記載之方法，計算每一重複單位之平均石备基數。〃 . 每一重複單位之平均磺基數：5.3個 [實施例87](有機電致發光元件之製作）、將具厚度200腿之ITO透明電極(陽極)之玻璃基板，使用中，巧劑、Semicoclean(Fumchi化學製）、超純水、丙酮、乙醇，進订超音波洗滌。將此基板以氮氣乾燥，再以uv/臭氧洗滌。首先， = ITO透明電極上，就電洞注人材料而言，使用實施例67得到之 :有磺基之高分子化合物之曱醇溶液(將高分子化合物20mg溶於 4mj之溶液），以旋轉塗布法形成2〇nm厚度之膜，於熱板上乾燥(1〇〇度、30分鐘)形成層。其次，將此玻璃基板固定在蒸 =衣置之基板支座，將蒸鍍槽減壓至3xl〇-4Pa。將n,n，—二〇」，基)一N，N’一二笨基聯苯胺以蒸鍍速度〇 2nm/sec蒸鍍4〇nm之厚，其次將參(8二羥基喹啉)鋁以蒸鍍速度0.2nm/sec蒸鍍5〇nm之。再者，將氟化鋰以〇.2nm/sec蒸鍍0.5nm之厚度。於其上蒸 ’’又、呂作為^極:製作有機電致發光元件(有機EL元件-1)。’、、、欢&又，瘵鍍係保持蒸鍍槽為減壓狀態實施。對製作之有機電致 f加直流電壓，5G度、乾燥氛圍下，以·A/cm2之机在度使連績驅動。確認初期為4.05V、亮度288cd/m2之 f色發光。將該元聽1⑽度放置1小時，球認發光特性無大變 121 200906909 2〇〇/^ ^ [比較例i]有機電致發光元件之壽命評價製作有機電致發度衰相對於初期亮 /~~\ 一CH.—r.M—The production of a polymer compound containing a sulfo group, wherein, in the polymer chain, and at least one of the benzene rings in the repeating unit represented by the compound B4-1, at least one unit of the fluorenyl group is at least one unit weight. 67. Using the polymer compound 1.35 g of the exemplified compound Al-i obtained in Example 1 and using the exemplified compound 1 ^ paleomolecular compound 1.35 g obtained in Example 49, the operation described in Example 67 was carried out, and = The molecular compound was 1.44g. Further, according to the method described in Example 67, the average enthalpy number of each repeating unit was calculated.均 Average number of sulfo groups per repeating unit: 4.9 [Example 85] Manufacture of a molecular compound containing a Schistosyl group, wherein 'polymer chain, with an example--showing compound D1-6 At least one benzene ring is substituted with a sulfo group, and at least one compound is used. The polymer compound 1.35g of the exemplified compound AA-1 obtained in Example 67 in Example 67 is used instead of the exemplified compound di obtained in Example 63. The operation described in Example 67 was carried out, except that 1.35 g of the polymer compound of 6 was obtained, to obtain 1.49 g of the desired molecular compound. Further, according to the method described in Example 67, the average number of supply units per repeat unit was calculated. The average number of sulfo groups per repeat unit: 5.2 120 200906909 [Example 86] The production of a polymer compound containing a sulfo group, wherein, in the polymer chain, the benzene in the repeating unit represented by the compound D1-7 is exemplified. At least one sulfonyl-substituted complex unit of at least one ring is used. In Example 67, the polymer compound 1.35g of the exemplified compound A1-1 obtained in Example 1 was used instead of the exemplified compound di obtained in Example 64. The operation described in Example 67 was carried out, except that 1.35 g of the molecular compound was obtained, and 1.51 g of the molecular compound of = was obtained. Further, according to the method described in Example 67, the average number of bases per repeating unit was calculated. 〃 . The average number of sulfo groups per repeating unit: 5.3 [Example 87] (Production of organic electroluminescence device), a glass substrate having an ITO transparent electrode (anode) having a thickness of 200 legs, in use, a fine agent, Semicoclean (made by Fumchi Chemical), ultrapure water, acetone, ethanol, and ultrasonic cleaning. The substrate was dried with nitrogen and washed with uv/ozone. First, on the ITO transparent electrode, in the case of the hole-injecting material, the thiol solution of the polymer compound having a sulfo group (a solution of the polymer compound 20 mg in a solution of 4 mj) was used to rotate. A film having a thickness of 2 nm was formed by a coating method, and dried on a hot plate (1 degree, 30 minutes) to form a layer. Next, the glass substrate was fixed to a substrate holder for steaming, and the vapor deposition bath was depressurized to 3 x 1 〇 -4 Pa. The n,N,-difluorene, yl)-N,N'-di-diphenylbenzidine is evaporated to a thickness of 4 〇nm at a vapor deposition rate of nm2 nm/sec, followed by ginseng (8-dihydroxyquinoline) aluminum. 5 〇 nm was deposited at a vapor deposition rate of 0.2 nm/sec. Further, lithium fluoride was evaporated to a thickness of 0.5 nm at 2.0 nm/sec. The organic electroluminescent element (organic EL element-1) was produced by steaming on it. In addition, the 瘵 plating system is carried out while maintaining the vapor deposition tank in a reduced pressure state. For the production of organic electric f and DC voltage, 5G degrees, in a dry atmosphere, the machine is driven by the A/cm2. It was confirmed that the initial color was 4.05 V and the luminance of 288 cd/m 2 was emitted. The element was placed at 1 (10) degrees for 1 hour, and the luminescence characteristic of the ball was not changed greatly. 121 200906909 2〇〇/^ ^ [Comparative Example i] Life evaluation of the organic electroluminescence device was made to produce organic electroluminescence with respect to the initial light/ ~~\ 一CH.—rM—

(7)(7)

PEDOTPEDOT

液(使高分子化合物20mg^^6旷7 f f 合物之甲醇溶成厚6〇nm之膜。於Ιϊ ==e4mi之溶液），以旋轉塗布法形之膜表面，結果已形成了均句的膜。以AFM進行之表面到定結果如表55所示。衣囬祖糙度測 [比較例2]成膜性評價 122 200906909 將實施例67得到之高分子化合物改為使用前述 PEDOT/PSS(BAYER 公司、商品名 BaytronP)式(7)，與實施例 88 以同樣方法成膜並觀察，結果相較於使用實施例67得到之高分子化合物成膜者，認為膜厚不均。以AFM進行之表面粗糙度測定結果如表55所示。 [比較例3]成膜性評價 f實施例67得到之高分子化合物改為使用將式(8)所示可從市面^到1聚合體(ADS公司製分子量28000 : ADS254BE)磺化得含有磺基之三芳胺聚合體(以下，稱為「式(8)之磺酸取代體」）， /、實施例88以同樣方法嘗試成膜，但難溶於甲醇，無法成膜。The liquid (so that the methanol of the polymer compound 20 mg^^6旷7 ff is dissolved into a film having a thickness of 6 〇nm. The solution of Ιϊ==e4mi) is formed by a spin coating method, and the result has formed a uniform sentence. Membrane. The surface-to-determination results by AFM are shown in Table 55. [Reference Example 2] Film Formability Evaluation 122 200906909 The polymer compound obtained in Example 67 was changed to the above-mentioned PEDOT/PSS (BAYER Company, trade name Baytron P) formula (7), and Example 88. When the film was formed in the same manner and observed, the film thickness was not uniform as compared with the film formation of the polymer compound obtained in Example 67. The surface roughness measurement results by AFM are shown in Table 55. [Comparative Example 3] Film-forming property evaluation f The polymer compound obtained in Example 67 was sulfonated to obtain a sulfonated product from a commercially available product (molecular weight: 28000: ADS254BE, manufactured by ADS Corporation) as shown in the formula (8). The triarylamine polymer (hereinafter referred to as "sulfonic acid substituent of the formula (8)) / / Example 88 was attempted to form a film in the same manner, but was insoluble in methanol and could not form a film.

⑻ 式(8)之磺酸取代體以下列方法合成。入=式(8)所示聚合體〇.4〇〇g溶於氯仿13.〇g，於氮氣流下，裝硫酸6g，於室溫攪拌48小時D將反應液倒入乙腈6〇ml中， ^ f出物。將得到之固體以乙腈洗滌至濾液之PH成為5，於70 又進仃8小時減壓乾燥，得到目的化合物〇.38g褐色固體。 =，與實施例67同樣進行，計算每一重複單位之平均素分析値1.0%(8) The sulfonic acid substituent of the formula (8) was synthesized in the following manner. The polymer 〇.4〇〇g of the formula (8) was dissolved in chloroform 13. 〇g, and 6 g of sulfuric acid was placed under a nitrogen stream, and stirred at room temperature for 48 hours. The reaction liquid was poured into 6 乙 acetonitrile. ^ f. The obtained solid was washed with acetonitrile until the pH of the filtrate became 5, and the mixture was dried under reduced pressure for further 8 hours to afford the title compound s. =, in the same manner as in Example 67, the average analysis of each repeating unit was calculated 値 1.0%

實施例88 ---—__ 母重複單位之平均績基數：〇 2個【表55】Example 88 ----__ Average number of bases of the mother repeat unit: 〇 2 [Table 55]

記載化合物 PED0T/PSSDocumented compound PED0T/PSS

, 代體| _^成膜 55可知，本發明之含有磺基之高分子化合物，相較於 123 86 200906909 ，膜性, a representative body | _^ film formation 55, the sulfonate-containing polymer compound of the present invention, compared to 123 86 200906909, film properties

Baytr「D式(8)之續酸取代體’呈現非常良好之成 [貫，^ 89]〜[實施例107]成膜性評價例67得到之高分子化合物改為實施例68〜實施例 It 有雜之高分子化合物，與實施例88以_方法進杆出 \並觀察，結果形成了均勻的膜。AFM之表面粗糙度測定結如表56所示。％Baytr "D-type (8) acid-substituent" showed very good results [Cross, ^89] ~ [Example 107] Film-forming property Evaluation Example 67 The polymer compound was changed to Example 68 to Example It The heteropolymer compound was observed and extruded in the same manner as in Example 88, and a uniform film was formed. The surface roughness measurement of AFM is shown in Table 56.

【表56】 —zL 試樣表面粗糙度Ra/nm 實施例89 — - 實施例68記載化合物 0.52 實施例90 實施例69記載化合物 0.49 實施例91 實施例70記載化合物 0.65 實施例92 實施例71記載化合物 0.53 實施例93 實施例72記載化合物 0.58 實施例94 實施例73記載化合物 0.61 實施例95 實施例74記載化合物 0.39 實施例96 實施例75記載化合物 0.49 實施例97 實施例76記載化合物 0.52 實施例98 實施例77記載化合物 0.61 實施例99 實施例78記載化合物 0.44 實施例100 實施例79記載化合物一 - 0.51 實施例101 實施例80記載化合物 0.42 實施例102 實施例81記載化合物 0.49 實施例103 實施例82記載化合物 0.55 實施例104 實施例83記載化合物 0.53 實施例105 f施例84記載化合物 0.42 實施例106 實施例85記載化合物 0.45 實施例107 膏施例86記載化合物 0.51 比較例2 PEDOT/PSS 1.02 比較例3 式(8)之磺酸取代體 ----- --- 無法成膜 124 200906909 由表56可知，本發明之含有磺基之高分子化合物，相較於 BaytronP及式⑻之磺酸取代體，呈現非常良好的成膜性。、 [實施例108](有機電致發光元件之製作續基體之評價）、將形成有圖案之具厚度150nm之ITO透明電極的玻璃基板(濺鑛成膜品；片電阻15Ω) ’依序以中性洗劑、Semic〇clean(Fumchi 化學製）、超純水、丙酮、異丙醇進行超音波洗滌後，以氮氣氣汽，燥，最後實施紫外線臭氧洗滌。其次，將實施例67得到之含^ 續基之高分子化合物之f醇溶液(2.G重量％)雌轉塗布法，形成厚65nm之膜，於熱板上減壓乾燥(1〇〇度、〗小洞注入輸送層。戌弟I窀其次，將AmericanDyeSource公司製高分子化合 ADS259BE(式14)之二^苯忠夜(2_〇重量％)以旋轉塗布法形成厚 50nm之膜，於熱板上於氮氣氛圍下進行加熱處理(18〇度小形成第2電洞注入輪送層。[Table 56] - zL sample surface roughness Ra / nm Example 89 - - Example 68 describes compound 0.52 Example 90 Example 69 describes compound 0.49 Example 91 Example 70 describes compound 0.65 Example 92 Example 71 Compound 0.53 Example 93 Example 72 describes compound 0.58 Example 94 Example 73 describes compound 0.61 Example 95 Example 74 describes compound 0.39 Example 96 Example 75 describes compound 0.49 Example 97 Example 76 describes compound 0.52 Example 98 Example 77 describes compound 0.61 Example 99 Example 78 describes compound 0.44 Example 100 Example 79 describes compound 1 - 0.51 Example 101 Example 80 shows compound 0.42 Example 102 Example 81 shows compound 0.49 Example 103 Example 82 Recorded Compound 0.55 Example 104 Example 83 Description Compound 0.53 Example 105 f Example 84 Description Compound 0.42 Example 106 Example 85 Compound 0.45 Example 107 Paste Example 86 Description Compound 0.51 Comparative Example 2 PEDOT/PSS 1.02 Comparative Example 3 sulfonic acid substituent of formula (8) ----- --- Film formation 124 200906909 It is understood from Table 56 that the sulfo group-containing polymer compound of the present invention exhibits very good film formability compared to Baytron P and the sulfonic acid substituent of the formula (8). [Example 108] (Evaluation of the substrate for the production of an organic electroluminescence device), a glass substrate (sputtering film-forming product; sheet resistance 15 Ω) having a patterned ITO transparent electrode having a thickness of 150 nm was sequentially Neutral lotion, Semic〇clean (made by Fumchi Chemical), ultrapure water, acetone, and isopropanol were ultrasonically washed, dried with nitrogen gas, and finally subjected to ultraviolet ozone washing. Next, the f-alcohol solution (2. G weight%) of the polymer compound containing the hydroxy group obtained in Example 67 was subjected to a female transfer coating method to form a film having a thickness of 65 nm, and dried under reduced pressure on a hot plate (1 degree). 〗〖Injection of the small hole into the transport layer. The second generation of the polymer, ADS259BE (Formula 14), which is made of American DyeSource, is formed into a film having a thickness of 50 nm by spin coating. The hot plate was heat-treated under a nitrogen atmosphere (18 degrees to form a second hole to be injected into the transfer layer).

CaH*i7 〇eH-i7 (14) i 5)之其f = f酿人輸送層沖洗處錢，將聚第(式 2二L f 重置％)以旋轉塗布法形成厚—m之膜，於 …板上減壓乾燥(140度、3〇分鐘)形成發光層。 ' 、CaH*i7 〇eH-i7 (14) i 5) its f = f brewing layer wash money, the poly (form 2 2 L f reset %) to form a thick-m film by spin coating, The luminescent layer was formed by drying under reduced pressure (140 °, 3 〇 minutes) on a plate. ' ,

C0H17 CeHt7 (15) i膜;蒸 IT。作為陽極'LiF二件施板 125 200906909 觀察發光。亮度以T〇PCON亮度計BM—8測定。以施加直流，於乾燥氛圍下乂 lum^/cm之疋電流禮度使連續驅 ί ° 500ed/J^0 動，、，、口果冗度降低率為22%。結果如表S7所示。 [實施例109]〜[實施例127] 二亡1 108 =，形成電洞注入輸送層時，將使用實施例67得至j之έ有磺基之高分子化合物，改為使用實施例68〜實施例％得到之含有續基之高分子化合物，除此以外，依照實施例1〇8記載，操作，製作有機電致發光元件。再者，與實施例1〇8同樣，對§亥元件施加直流電壓，測定該元件之特性，結果如表57所示。 • [比較例A—1] 貫施例108中，形成第1電洞注入輸送層時，將使用實施例 67得到之高分子化合物，改為使用前述pED〇T/pss(BAYER公司、商品名BaytronP)式(7)，除此以外，依照實施例1〇8記載之操作，製作有機電致發光元件。再者，與實施例108同樣，對該元件施加直流電壓，測定該元件之特性，結果如表57所示。【表57】有機電致發光元件第1電洞注入輸送層亮度 (cd/m2) 電壓 (V) 降低率 (%) 實施例108 實施例67記載化合物 162 5.1 22 實施例109 實施例68記載化合物 154 5.3 26 實施例110 實施例69記載化合物 144 5.5 19 實施例111 實施例70記載化合物 146 4.9 23 實施例112 實施例71記載化合物 160 5.4 20 實施例113 實施例72記載化合物 139 5.5 18 實施例114 實施例73記載化合物 157 5.3 28 實施例115 實施例74記載化合物 153 5.2 26 實施例116 實施例75記載化合物 159 5.1 25 126 200906909 實施例117 實施例76記載化合物 162 5.4 26 實施例118 實施例77記載化合物 140 5.7 21 實施例119 實施例78記載化合物 150 5.4 26 實施例120 ^施例79記載化合物 153 5.3 17 實施例121 實施例80記載化合物 142 5.7 25 實施例122 實施例84記載化合物 144 5.4 20 實施例123 實施例82記載化合物 152 5.5 26 實施例124 實施例83記載化合物 158 5.2 22 實施例125 實施例84記載化合物 151 5.5 25 實施例126 實施例85記載化合物 154 5.8 19 實施例127 實施例86記載化合物 138 5.2 29 比較例Α-1 PEDOT/PSS 105 5.4 55 [實施例128]C0H17 CeHt7 (15) i film; steamed IT. As an anode 'LiF two-piece plate 125 200906909 Observed luminescence. The brightness was measured by a T〇PCON luminance meter BM-8. By applying direct current, the current 礼 lum ^ / cm in a dry atmosphere makes the continuous drive ί ° 500 ed / J ^ 0 movement,,,,,,,,,,,,,,,,,,,, The results are shown in Table S7. [Example 109] to [Example 127] Two deaths 1 108 =, when a hole injection transport layer was formed, the polymer compound having a sulfo group obtained in Example 67 was used, and the use of Example 68 was changed. Example 1 An organic electroluminescent device was produced in the same manner as in Example 1 to 8 except that the polymer compound having a retentate was obtained. Further, in the same manner as in the first to eighth embodiments, a DC voltage was applied to the element, and the characteristics of the element were measured. The results are shown in Table 57. [Comparative Example A-1] When the first hole injection transport layer was formed in Example 108, the polymer compound obtained in Example 67 was used, and the above pED〇T/pss (BAYER, trade name) was used instead. An organic electroluminescent device was produced in accordance with the procedure described in Examples 1 to 8 except for Baytron P) (7). Further, a DC voltage was applied to the device in the same manner as in Example 108, and the characteristics of the device were measured. The results are shown in Table 57. [Table 57] Organic Electroluminescence Element First Hole Injection Transport Layer Brightness (cd/m2) Voltage (V) Reduction Rate (%) Example 108 Example 67 Description Compound 162 5.1 22 Example 109 Example 68 Compound 154 5.3 26 Example 110 Example 69 shows compound 144 5.5 19 Example 111 Example 70 shows compound 146 4.9 23 Example 112 Example 71 describes compound 160 5.4 20 Example 113 Example 72 describes compound 139 5.5 18 Example 114 Example 73 describes compound 157 5.3 28 Example 115 Example 74 describes compound 153 5.2 26 Example 116 Example 75 describes compound 159 5.1 25 126 200906909 Example 117 Example 76 describes compound 162 5.4 26 Example 118 Example 77 Compound 140 5.7 21 Example 119 Example 78 describes compound 150 5.4 26 Example 120 ^ Example 79 describes compound 153 5.3 17 Example 121 Example 80 shows compound 142 5.7 25 Example 122 Example 84 describes compound 144 5.4 20 Example 123 Example 82 shows compound 152 5.5 26 Example 124 Example 83 describes compound 158 5.2 22 Example 125 Compound according to Example 84 5.5 151 126 25 cases described in Example 85 Compound 154 5.8 19 Example 127 86 embodiment the compound described in Example 29 5.2 138 Comparative Example Α-1 PEDOT / PSS 105 5.4 55 [Example 128]

將形成有圖案之具厚度150nm之ITO透明電極的玻璃基板(濺鑛成膜〇口，片電阻15Ω)，依序以中性洗劑、Semicoclean(Furuchi 巧學製）、超純水、丙酮、異丙醇進行超音波洗滌後，以氮氣氣流乾燥’最後進行紫外線臭氧洗滌。其次，將前述pED〇T/pSS以旋轉塗，法形成厚65nm之膜，於熱板上減壓乾燥(200度、1小時），形成第上電洞注入輸送層。其次，將實施例3合成之高分子化合物之曱f溶液(1.5重量％)，以旋轉塗布法形成厚50nm之膜，於熱板上於氣氣氛圍τ進行加熱處理(⑽度、丨小時），形成第2電洞注入輸送層。述聚^之二Ψ 制〉认輸送層進行沖洗處理後，將前膜二曱液/.2重量％)藉旋轉塗布法形成厚60nm之二:壓:乾燥040度、30分鐘），形成發光層。其次，將將氟化鐘 Ξ^ΙΙΙΙ： 127 200906909A glass substrate having a patterned 150 nm thick ITO transparent electrode (sputtering film opening, sheet resistance 15 Ω), followed by a neutral detergent, Semicoclean (Furuchi), ultrapure water, acetone, After ultrasonic washing with isopropyl alcohol, it was dried with a nitrogen gas stream and finally subjected to ultraviolet ozone washing. Next, the above pED〇T/pSS was spin-coated to form a film having a thickness of 65 nm, and dried on a hot plate under reduced pressure (200 °, 1 hour) to form an upper hole injection transport layer. Next, the 曱f solution (1.5% by weight) of the polymer compound synthesized in Example 3 was formed into a film having a thickness of 50 nm by a spin coating method, and heat-treated in a gas atmosphere τ on a hot plate ((10) degrees, 丨 hours). Forming a second hole injection transport layer. After the rinsing treatment of the transport layer, the front film diterpene solution /. 2% by weight) by spin coating method to form a thickness of 60nm two: pressure: dry 040 degrees, 30 minutes), the formation of luminescence Floor. Secondly, will be the fluorinated clock Ξ ^ ΙΙΙΙ: 127 200906909

有機電致發光元件。將此有機電致發光元件中，ITO作為陽極、 LiF/Al作為陰極，施加直流電壓並通過玻璃基板觀察發光。亮度以TOPCON亮度計BM—8測定。 & X 對於製作之有機電致發光元件施加直流電壓，於乾燥氛圍下以10mA/cm2之定電流密度使連續驅動。確認初期有5 4v、亮度 151cd/m2之藍色發光。從初期亮度500cd/m2進行200小時之連續驅動’結果免度之降低率為28%。結果如表58所示。、 [實施例129]〜[實施例153] 將實施例128中’形成第2電洞注入輸送層時，實施例3得到之高分子化合物改為使用實施例4、8、10、15、19、21、22 : 23、25、41、42、43、44、45、46、47、48、51、54、56、57、 59、61、62、65得到之高分子化合物，除此以外依照實施例之操作，製作有機電致發光元件。再者，與實施例&8同樣對該元件施加直流電壓，測定該元件之特性，結果如表58所示。μ [比較例Β — 1] 58所示。將貫施例128中，形成第2電洞注入輸送層時，實施例3得到之高分子化合物改為使用前述ADS259BE(式14)，除此以外依照實施例128之操作，製作有機電致發光元件。再者，與實施 128同樣地對該元件施加直流電壓，測定該元件之特性，^果如表 [比較例Β — 2] 到之為==輸=號=Organic electroluminescent element. In the organic electroluminescence device, ITO was used as an anode and LiF/Al was used as a cathode, and a direct current voltage was applied thereto to observe light emission through a glass substrate. Brightness was measured by TOPCON Luminance Meter BM-8. & X A DC voltage was applied to the produced organic electroluminescence device, and continuous driving was performed at a constant current density of 10 mA/cm 2 in a dry atmosphere. It was confirmed that there was a blue light of 5 4v and a brightness of 151 cd/m2 at the beginning. The continuous driving for 200 hours from the initial luminance of 500 cd/m2 was reduced by 28%. The results are shown in Table 58. [Example 129] to [Example 153] When the second hole was injected into the transport layer in Example 128, the polymer compound obtained in Example 3 was changed to use Examples 4, 8, 10, 15, and 19. 21, 22: 23, 25, 41, 42, 43, 44, 45, 46, 47, 48, 51, 54, 56, 57, 59, 61, 62, 65, the polymer compound obtained, in addition to The operation of the examples produced an organic electroluminescent device. Further, a DC voltage was applied to the device in the same manner as in the example & 8, and the characteristics of the device were measured. The results are shown in Table 58. μ [Comparative Example Β — 1] 58 is shown. In the example 128, when the second hole was injected into the transport layer, the polymer compound obtained in Example 3 was changed to the above-mentioned ADS259BE (Formula 14), and otherwise, the organic electroluminescence was produced in accordance with the operation of Example 128. element. Further, a DC voltage is applied to the device in the same manner as in the implementation 128, and the characteristics of the device are measured. The results are as shown in the table [Comparative Example 2-2] ======

對該元件施加1流1：壓，測定該元件之特性，與實施例128同樣地 ’結果如表58所示。 128 200906909The current was applied to the device at a pressure of 1 to 1, and the characteristics of the device were measured. The results are shown in Table 58 as in the case of Example 128. 128 200906909

【表58】有機電致發光元件第2電洞注入輸送層亮度 (cd/m2) 電壓 (V) 降低率 (%) 實施例128 實施例3記載化合物 151 5.4 28 實施例129 實施例4記載化合物 147 5.2 19 實施例130 實施例8記載化合物 153 5.0 29 實施例131 實施例10記載化合物 150 5.2 18 實施例132 實施例15記載化合物 157 5.5 26 實施例133 實施例19記載化合物 159 5.2 22 實施例134 實施例21記載化合物 164 5.3 16 實施例135 實施例22記載化合物 157 5.2 21 實施例136 實施例23記載化合物 148 5.6 25 實施例137 實施例25記載化合物 139 5.7 29 實施例138 實施例41記載化合物 148 5.6 28 實施例139 實施例42記載化合物 142 5.4 24 實施例140 實施例43記載化合物 150 5.5 28 實施例141 實施例44記載化合物 157 5.5 21 實施例142 實施例45記載化合物 137 5.8 25 實施例143 實施例46記載化合物 144 5.5 24 實施例144 實施例47記載化合物 152 5.4 24 實施例145 實施例48記載化合物 157 5.3 26 實施例146 實施例51記載化合物 152 5.5 26 實施例147 實施例54記載化合物 156 5.4 21 129 200906909 實施例148 實施例56記载化合物 144 5.7 19 實施例149 實施例57記載化合物 151 5.6 25 實施例150 實施例59記載化合物 162 5.5 23 實施例151 實施例61記載化合物 147 5.4 25 實施例152 實施例62記盤化合物 138 5.6 28 實施例153 實施例65記載化合物 141 5.5 29 比較例B-1 比較例B-1記載化合物 105 5.4 55 比較例B-2 比較例B-2記载化合物 122 5.8 38 [實施例155] 將形成有圖案之具厚度150nm之ITO透明電極的玻璃基板(濺鍍成膜品；片電阻15Ω)，依序以中性洗劑、Semic〇dean(Furuchi 化學製)、超純水、丙酮、異丙醇進行超音波洗滌後，以氮氣氣流乾燥’敢後實施紫外線臭氧洗務。其次，將實施例67得到之含有石頁基之尚分子化合物之曱醇溶液(2‘〇重量％)藉旋轉塗布法形成厚 65nm之膜，於熱板上進行減壓乾燥(1〇〇度、丨小時），形成第工電洞注入輸送層。其次，將實施例3得到之高分子化合物之曱苯溶液(I.5重量％)藉旋轉塗布法形成厚5〇nm之膜，於熱板上於說氣氛圍下進行加熱處理(180度、1小時）’形成第2電洞注入輸送層。、、其次’以甲苯將第2電洞注入輸送層進行沖洗處理後，將前述聚第之二曱苯溶液(1.2重量％)藉旋轉塗布法形成厚6〇nm之膜’於熱板上減壓乾燥(M0度、30分鐘），形成發光層。並次玻璃基板固定在紐裝置之基板支座，於發光層之上，籠化鐘 (LiF)使用銦舟，以蒸鑛速度〇 2麵/秒製作膜厚〇.5·之膜後 f (A1)以鎢舟加熱，以蒸鍍速度2 〇nm/sec形成膜厚i〇〇nm之鋁層’完成陰極。以此方式，可製具尺寸2inmx2nim之發光分的有機電致發光元件。此有機電致發光元件中，以Ιτ〇作為 f UF/Al作為陰極’施加直流電壓，並通過玻璃基板觀察發光。觉度以TOPCON亮度計BM-8測定。 130 200906909 對製γ乍之有機電致發光元件施加直流電壓，於乾燥氛圍下以 1 OmA/cm之疋電流选度使連續驅動。確認初期有ν、亮度 165cd/m之藍色發光。從初期亮度5〇〇cd/m2進行2〇〇小時之連續驅動，結果亮度降低率為26%。結果如表59所示。 [實施例156]〜[實施例ι80] 貫施例155中於電洞注入輸送層形成時，將使用實施例3得到之高分子化合物改為使用實施例4、8、10、15、19 21、22、 23、25、4卜 42、43、44、45、46、47、48、51、54、56、57、 59、61、62、65得到之高分子化合物，除此以外依照實施例之操作，製作有機電致發光元件。再者，與實施例155'同樣，對該元件施加直流電壓，測定該元件之特性，結果如表59所示。【表59】 ’、有機電致發光元件第2電洞注入輸送層亮度 (cd/m2) 電壓 (V) 降低率 (%) 實施例155 實施例3記載化合物 165 5.3 26 實施例156 實施例4記載化合物 153 5.1 25 實施例157 實施例8記載化合物 147 5.2 「24 實施例158 實施例10記載化合物 155 5,3 22 實施例159 實施例15記載化合物 139 5.4 27 實施例160 實施例19記載化合物 161 5.3 28 實施例161 實施例21記載化合物 168 5.2 28 實施例162 實施例22記載化合物 157 5.3 21 實施例163 實施例23記載化合物 149 5.5 19 實施例164 實施例25記載化合物 142 5.4 24 實施例165 實施例41記載化合物 137 5.5 29 實施例166 實施例42記載化合物 148 5.4 27 實施例167 實施例43記載化合物 156 5.5 21 實施例168 實施例44記載化合物 139 5.7 20 實施例169 實施例45記載化合物 146 5.2 27 131 200906909 ( 實施例170 實施例46記載化合物 138 實施例171 實施例47記載化合物 159 實施例172 實施例48記載化合物 155 實施例173 實施例51記載化合物 167 實施例174 實施例54記載化合物 162 實施例Π5 實施例56記載化合物 154 實施例176 實施例57記載化合物 139 實施例177 實施例59記載化合物 163 實施例178 1 實施例61記載化合物 147 實施例179 1 實施例62記載化合物 155 實施例180 實施例65記載化合物 135[Table 58] Organic Electroluminescence Element Second Hole Injection Transport Layer Brightness (cd/m2) Voltage (V) Reduction Rate (%) Example 128 Example 3 Description of Compound 151 5.4 28 Example 129 Example 4 147 5.2 19 Example 130 Example 8 describes compound 153 5.0 29 Example 131 Example 10 describes compound 150 5.2 18 Example 132 Example 15 describes compound 157 5.5 26 Example 133 Example 19 describes compound 159 5.2 22 Example 134 Example 21 describes compound 164 5.3 16 Example 135 Example 22 describes compound 157 5.2 21 Example 136 Example 23 describes compound 148 5.6 25 Example 137 Example 25 describes compound 139 5.7 29 Example 138 Example 41 describes compound 148 5.6 28 Example 139 Example 42 shows compound 142 5.4 24 Example 140 Example 43 describes compound 150 5.5 28 Example 141 Example 44 shows compound 157 5.5 21 Example 142 Example 45 shows compound 137 5.8 25 Example 143 Example 46 describes compound 144 5.5 24 Example 144 Example 47 describes compound 152 5.4 24 Example 145 Example 48 describes compound 157 5.3 26 Example 146 Example 51 describes compound 152 5.5 26 Example 147 Example 54 shows compound 156 5.4 21 129 200906909 Example 148 Example 56 describes compound 144 5.7 19 Example 149 Example 57 Recorded Compound 151 5.6 25 Example 150 Example 59 Description of Compound 162 5.5 23 Example 151 Example 61 Description of Compound 147 5.4 25 Example 152 Example 62 Disk Compound 138 5.6 28 Example 153 Example 65 Description of Compound 141 5.5 29 Comparative Example B-1 Comparative Example B-1 Description of Compound 105 5.4 55 Comparative Example B-2 Comparative Example B-2 describes Compound 122 5.8 38 [Example 155] A glass having a pattern of 150 nm thick ITO transparent electrode was formed. The substrate (sputtered film-forming product; sheet resistance 15 Ω) was ultrasonically washed with a neutral detergent, Semic〇dean (Furuchi Chemical), ultrapure water, acetone, and isopropyl alcohol, and then dried by a nitrogen gas stream. Dare to implement UV ozone washing. Next, a decyl alcohol solution (2' 〇% by weight) of the sulfhydryl group-containing compound obtained in Example 67 was formed into a film having a thickness of 65 nm by a spin coating method, and dried under reduced pressure on a hot plate (1 degree). , 丨 hours), forming the first hole injection into the transport layer. Next, the ruthenium benzene solution (I.5 wt%) of the polymer compound obtained in Example 3 was formed into a film having a thickness of 5 〇 nm by a spin coating method, and heat-treated under a gas atmosphere on a hot plate (180 degrees, 1 hour) 'The second hole is injected into the transport layer. Then, after the second hole is injected into the transport layer with toluene for rinsing treatment, the polydiphenylene solution (1.2% by weight) is formed by spin coating to form a film having a thickness of 6 〇 nm on the hot plate. The film was dried by pressure (M0 degree, 30 minutes) to form a light-emitting layer. The glass substrate is fixed on the substrate support of the new device, above the luminescent layer, and the caged clock (LiF) is made of indium boat, and the film thickness is 以2/sec. A1) Heating with a tungsten boat, forming an aluminum layer having a film thickness i〇〇nm at a vapor deposition rate of 2 〇nm/sec. In this way, an organic electroluminescence element having a luminescence fraction of 2 inmx 2 nim can be produced. In this organic electroluminescence device, a DC voltage was applied as 阴极τ〇 as f UF/Al as a cathode, and light emission was observed through a glass substrate. The sensitivity was measured by TOPCON Luminance Meter BM-8. 130 200906909 A direct current voltage is applied to an organic electroluminescent device of γ 乍, and is continuously driven at a current of 1 OmA/cm in a dry atmosphere. It was confirmed that there was a blue light with ν and a luminance of 165 cd/m at the beginning. The continuous driving was performed for 2 hours from the initial luminance of 5 〇〇 cd/m 2 , and as a result, the luminance reduction rate was 26%. The results are shown in Table 59. [Example 156] to [Example ι80] When the hole injection transport layer was formed in Example 155, the polymer compound obtained in Example 3 was changed to use Examples 4, 8, 10, 15, 19 21 Polymer compounds obtained by 22, 23, 25, 4, 42, 43, 44, 45, 46, 47, 48, 51, 54, 56, 57, 59, 61, 62, 65, in addition to the examples The operation is to fabricate an organic electroluminescent element. Further, in the same manner as in Example 155', a DC voltage was applied to the device, and the characteristics of the device were measured. The results are shown in Table 59. [Table 59] ', Organic Electroluminescent Element Second Hole Injection Transport Layer Brightness (cd/m2) Voltage (V) Reduction Rate (%) Example 155 Example 3 Description Compound 165 5.3 26 Example 156 Example 4 Recorded Compound 153 5.1 25 Example 157 Example 8 Description of Compound 147 5.2 "24 Example 158 Example 10 Description of Compound 155 5,3 22 Example 159 Example 15 Description of Compound 139 5.4 27 Example 160 Example 19 Description of Compound 161 5.3 28 Example 161 Example 21 describes compound 168 5.2 28 Example 162 Example 22 describes compound 157 5.3 21 Example 163 Example 23 describes compound 149 5.5 19 Example 164 Example 25 describes compound 142 5.4 24 Example 165 Example 41 describes compound 137 5.5 29 Example 166 Example 42 shows compound 148 5.4 27 Example 167 Example 43 describes compound 156 5.5 21 Example 168 Example 44 shows compound 139 5.7 20 Example 169 Example 45 shows compound 146 5.2 27 131 200906909 (Example 170 Example 46 describes compound 138 Example 171 Example 47 describes compound 159 Example 172 Example 48 shows compound 155 Example 173 Example 51 shows compound 167 Example 174 Example 54 shows compound 162 Example Π 5 Example 56 shows compound 154 Example 176 Example 57 describes compound 139 Example 177 Example 59 Recorded Compound 163 Example 178 1 Example 61 Description of Compound 147 Example 179 1 Example 62 Description of Compound 155 Example 180 Example 65 Description of Compound 135

從表57〜表59可知，將本發明之含有磺基之高分及开>成其中間體之本發明之高分子化合物作為電洞注入二物之有機EL元件，發光亮度高且發光效率優異，再二乞低，於元件壽命之點優越。儿度降低率【產業利用性】使^本發明之含有磺基之高分子化合物及成為其如明之高分子化合物得到之有機電致發光作说源、各種發光鱗、顯示it件、標識、感測i作為面板型光【圖式簡單說明】形態㈣&賴較佳實施 ==機電致發光砂-例之剖面概略圖 :H機電_&元件一例之剖面概略 Ξ 4 致發光元件一例之剖面概略圖圖致發光元件一例之剖面概略圖係有機電致發光元件-例之剖面概略圖圖 132 200906909 圖7係有光元件一例之剖面概略圖。圖8係有機電致元件一例之剖面概略圖。疋件一例之剖面概略圖。【主要元件符號說明 1基板 2陽極 3電洞注入輪送層 3a電洞注入輸送成分 4發光層 4a發光成分 5電子注入輪送層 5a電子注入成分 5"電洞注入輸迭層 6陰極 7電源 133As can be seen from Table 57 to Table 59, the organic EL element of the present invention in which the polymer compound of the present invention containing a high concentration of a sulfo group and an intermediate thereof is incorporated as a hole has high luminance and luminous efficiency. Excellent, second to none, superior in terms of component life. The degree of reduction in the degree of use [Industrial use] The organic compound containing the sulfo group of the present invention and the organic electroluminescence source obtained as the polymer compound of the present invention, various luminescent scales, display elements, logos, and senses i is used as the panel type light [Simplified description of the drawing] Form (4) & preferred implementation == electromechanical illuminating sand - example cross-sectional overview: H electromechanical _& component example cross-sectional outline Ξ 4 section of the illuminating element BRIEF DESCRIPTION OF THE DRAWINGS FIG. 7 is a schematic cross-sectional view showing an example of a light-emitting element. FIG. 7 is a schematic cross-sectional view showing an example of an organic light-emitting element. Fig. 8 is a schematic cross-sectional view showing an example of an organic electroluminescent element. A schematic cross-sectional view of an example of a piece. [Main component symbol description 1 substrate 2 anode 3 hole injection rounding layer 3a hole injection transport component 4 light emitting layer 4a light emitting component 5 electron injection wheeling layer 5a electron injection component 5 " hole injection layer 6 cathode 7 power supply 133

Claims

200906909 十、申請專利範圍：係為對於高分子鏈中具有 1. 一種含有磺基之高分子化合物，通式⑴··200906909 X. Patent application scope: It is a polymer compound containing a sulfo group in the polymer chain, and the formula (1)··

(1 Λ 表示L之整基^; ρ2表示Q〜5之整數、Ρ3、ρ4 X4可以彼此鍵結成環;Y二香又矣基;勺X2、X3與同或不同，表示2價芳香於其，方9私基，Ar〜Ar彼此可為相族基彼此鍵結形成環之关二二’此等2價芳香族基可為芳香 ——CH=CH___，錢;T與护係擇自於單鍵、—(CH2)t .CO- ^ -so- . ^so!： Js：,0''' -s~ ' ' 相同或不同;t表示整意2「所f成群組之基，彼此可為 :可彼此鍵結成環;E表示氫原子敌^及Q絲烧基或芳香族基，亦之整數）所示重複單位^少'丨彻或芳香族基；m、η表示0〜2 構造。之鬲分子化合物導入磺基而成之 2.如申請專利範圍第1項一對於在高分子鏈中具有通式(2) . 3有磺基之高分子化合物，其係為 134 (2) 200906909 xVx2(1 Λ denotes the whole base of L^; ρ2 denotes an integer of Q~5, Ρ3, ρ4 X4 may be bonded to each other to form a ring; Y is fragrant and sulfhydryl; and spoons X2 and X3 are the same or different, indicating a divalent aromatic , square 9 private base, Ar ~ Ar can be mutually bonded to each other to form a ring of two or two 'the two divalent aromatic groups can be aromatic - CH = CH___, money; T and the protection system from Single key, —(CH2)t .CO- ^ -so- . ^so!: Js:,0''' -s~ ' ' is the same or different; t means the meaning of 2 "f" They may be: they may be bonded to each other to form a ring; E represents a hydrogen atom and a Q-alkyl group or an aromatic group, and an integer thereof) is a repeating unit of less than a 'definitely or aromatic group; m, η represents 0~ 2 structure. The molecular compound is introduced into the sulfo group. 2. According to the first item of the patent application, the polymer compound having the general formula (2). 3 having a sulfo group in the polymer chain is 134 ( 2) 200906909 xVx2

一（式Λ: Zl〜z4、ρ1 〜Ρ4、χ1 〜X4、γ 及 m、η 同前）所tf重丨個之高分子化合物導人縣而成之構造。 3.如申請專利範圍第1項之含有磺基之高分子化合物，其中該Y所示基為通式(a—丨)所示基：(Formula: Zl~z4, ρ1~Ρ4, χ1~X4, γ and m, η are the same as before) The structure of the polymer compound that is tf is one of the most important. 3. The sulfo group-containing polymer compound according to claim 1, wherein the group represented by Y is a group represented by the formula (a-丨):

a — 1 ) (式中，Q為擇自於單鍵、〇、s、现、⑽巧、c〇、s〇、处 SiH2、SiMe2所構成群組之基，k表示〇〜2之整數）。 4.如申請專利範圍第2項之含有石黃基之高分子化合物，其中該Y所不基為通式(a—丨)所示基：a — 1 ) (wherein Q is a group selected from the group consisting of a single bond, 〇, s, present, (10), c〇, s〇, SiH2, SiMe2, and k is an integer of 〇~2) . 4. A polymer compound containing a fluorescene group according to item 2 of the patent application, wherein the Y group is not a group represented by the formula (a-丨):

(a 一 1 ) (式中 ’ Q 為擇自於單鍵、〇、s、CH2、CMe2、c〇、s〇、s〇、 SiH2、SiMe2所構成群組之基，k表示〇〜2之整數）。 2 U申，專利範圍第！項之含有磺基之高分子化合物，其 135 200906909 胺基，及通式(la)〜(3a): 一 (〇)l —D(la) —0(C = 0)-D(2a) ~(C = 〇)〇-D(3a) 碳數棘代之紐狀、分支雜或環狀之数8之^基·、、、取代或經取代之碳數4〜12之1價芳香族某、無取代或經取代之碳數7〜2() 基構成群組之基。之认基，L表不0或⑽示基所中，圍第1項之含祕之高分子化合物，其項中;二?之有含機有電IS:合物包含申請專糊第 > 至6 弟1至6項中任-項之含有糾月寻利乾圍之狀態使用。 -基之_子化合物溶解於有機溶劑機-H中料利圍帛8項之有機電致發光元件材料，A中1古機〉谷劑為極性溶劑。卞利^千具中该有 10. —種有機電致發光元件，係專利範圍第1至6項中任1之含有持含有申請種之層至少1層而成。有頁基之向刀子化合物至少i 11. 如申請專利範圍第10項含有=基之高分子化合物之層，為電荷注人件’其中，該電荷有機電致發光元件，其中，該含該項之有機電致發光元件，其中，包 Μ-種高分子化合物，於高分子鏈中具有至少⑽通式⑴ 136 200906909 r(a-1) (wherein Q is a group selected from the group consisting of a single bond, 〇, s, CH2, CMe2, c〇, s〇, s〇, SiH2, SiMe2, and k represents 〇~2 Integer). 2 U Shen, the scope of patents! A sulfo group-containing polymer compound, 135 200906909 amine group, and formula (la)~(3a): one (〇)l - D(la) - 0(C = 0)-D(2a) ~ (C = 〇)〇-D(3a) The number of carbonaceous spines, the branching or the number of rings, the number of 8 or The unsubstituted or substituted carbon number 7~2() groups form the group of the group. The acknowledgment, the L table is not 0 or (10) in the base, the polymer compound containing the secret of the first item, in the item; the second is the machine-containing electricity IS: the compound contains the application for the paste > To the 6th to 6th of the 6th to 6th, the item contains the status of the correction of the moon. - The base compound is dissolved in an organic solvent machine-H, which is an organic electroluminescent device material of 8 items, and the A machine is a polar solvent. There are 10. organic electroluminescent elements in the ^利^千具, which are composed of at least one layer containing the layer of the application of the first to sixth aspects of the patent range. a substrate-based knives compound at least i. 11. The layer of the polymer compound containing the base of claim 10, which is a charge injection member, wherein the charge organic electroluminescence device, wherein the An organic electroluminescence device, wherein the inclusion polymer compound has at least (10) in the polymer chain of the formula (1) 136 200906909 r

(1) 表示。〜4 p2f示G〜5之整數、P3、P4 X4可以彼此锤从，一表，1彳貝之芳香族基，X1與X2、X3盥同或不同2價芳香族基，Arl〜Ar4彼此可為相此鍵結形成環之料t A Tl * Tf ^價耗祕可為料族基彼 CH=CH、^方麵基;T與丁為擇自於單鍵、-(CH2)「、— -SO-^so 0 —、〜S-、-_——CO-、同;t表示1〜成群組之基，彼此可為相同或不結成環.μ - 數，Q Q表示烧基或芳香絲，亦可彼此鍵戶;ΪΪΪΪΓ原子、烧基或芳香族基-、n表示。〜2之整數）子鏈中圍第14項之高分子化合物，其中，於高分千鏈肀具有至少1個以通式(2): 137 (2) 200906909 XVX2(1) indicates. 〜4 p2f shows an integer of G~5, P3, P4 X4 can be hammered from each other, a table, an aromatic group of 1 mussel, X1 and X2, X3 are the same or different divalent aromatic groups, and Arl~Ar4 can be mutually In order to form a ring, the material of the bond t A Tl * Tf ^ can be the base of the group of CH=CH, ^, and the T and D are selected from a single bond, -(CH2)", - SO-^so 0 —, —S—, —_—CO—, and the same; t represents a group of 1 to group, which may be the same or not ringing each other. μ - number, QQ means alkyl or aromatic silk , or may be bonded to each other; a ruthenium atom, a ruthenium group or an aromatic group -, n represents an integer of ~2) a polymer compound of the 14th item in the sub-chain, wherein the high-stranded thousand-chain 肀 has at least one By the general formula (2): 137 (2) 200906909 XVX2

(式中，Ζ1〜Ζ4、ρ1〜ρ4、X1〜χ4、γ及單位。及m、η同前）所示重複 16. —種有機電致發光元件材料’包令由或I5項之高分子化合物。 ^ 3申§月專利範圍第14項 Π. —種有機電致發光元件材料，直圍第14或丨5項之高分子化合物於溶解在使中請專利範 18. -種有機電致發光元件，係於i 之狀態使用。 :利範圍第U或15項之高分子化合物至少/種之 c. 有該棒其中，含 20. 如申請專利範圍第19項邊9 電荷注入輸送層為電洞注入輸送層。、電致發光元件，其中，該 21. 如申請專利範圍第2〇項含該電洞注入輸送層至少2層。幾電致發光元件，其中，包 22. —種有機電致發光元件專利範圍第1項之含有續基之高八^十電極間，夾持含有申請層，並夾持含有申請專利範圍第*14化1物至少1種之層至少1 層至少1層而成。貝之而分子化合物至少1種之 138(In the formula, Ζ1~Ζ4, ρ1~ρ4, X1~χ4, γ and units. And m, η are the same as before) repeat 16. A kind of organic electroluminescent device material 'Package or I5 item polymer Compound. ^ 3 § § Patent Range No. 14 Π. A kind of organic electroluminescent device material, the polymer compound of the 14th or the 丨5th column is dissolved in the patent. 18. Organic electroluminescent device , used in the state of i. : The polymer compound of the U or 15th item of the range is at least / in the c. There is a stick which contains 20. As in the scope of claim 19, the charge injection layer is a hole injection transport layer. An electroluminescent device, wherein the second embodiment comprises at least two layers of the hole injecting and transporting layer as in the second aspect of the patent application. a plurality of electroluminescent elements, wherein the package 22 is an organic electroluminescent element, the first item of the patent range 1 includes a high-altitude eight-ten electrode, the clamping contains the application layer, and the clamping contains the scope of the patent application* At least one layer of at least one of 14 layers is formed of at least one layer. At least one of the molecular compounds