TW201000484A

TW201000484A - Conjugated compound containing fused heterocyclic structure, and their use

Info

Publication number: TW201000484A
Application number: TW97124479A
Authority: TW
Inventors: Chin-Kang Sha; Chia-Lin Liu; Vellingiri Raghukumar; Jhang-Rong Ciou
Original assignee: Chin-Kang Sha
Priority date: 2008-06-30
Filing date: 2008-06-30
Publication date: 2010-01-01

Abstract

The invention discloses a conjugated compound containing a fused heterocyclic structure. The conjugated compound containing fused heterocyclic has a general structure as follows, wherein A is selected from atoms such as S or N and so on. In addition, A may further include a substituent group. R1 to R19 in the above structure may be the same or different substituent groups. The invention also discloses applications of the conjugated compound as set forth above. More particularly, the applications include applications in hole conducting materials, and light emitting materials in organic electroluminescence devices.

Description

201000484 九、發明說明：【發明所屬之技術領域】本發明係有關於具有雜多環結構之共輛化合物及其應用。 ‘ 【先前技術】 . 異駢吡咯雜環，由於具有4n+2個；r電子系統及芳香族的一些特性，因而引起合成及理論化學家感到興趣的研究主題之一。另一方面，異駢吡咯雜環本身具有一些特殊的性質，如化合物的互變異構化（tautomer)平衡、n比洛的雙稀特性、及極度的不戈'疋’ 例如如在酸性反應條件下易形成導電高分子等’使得異°引π朵 (isoindole)系統及類似雜環化合物的研究已經越來越受到化學領域以及材料領域人士的重視。有機電激發光顯示技術（Organic ElectroLuminescence ; OEL) ’ 具備了自發光、高應答速度、視角廣（超過160度）、省電、高對比 •以及成本較低、重量輕、厚度薄、可撓西、可製作大面積、高亮 * 度、可全彩化等優點，為平面顯示器中的一個明星產品。 OEL發光原理為施加直流電壓時，電洞會由陽極注入電洞傳導層之最高填滿分子軌域（Highest Occupied Molecular Orbital, HOMO)，而電子由陰極注人電子傳導層之最低未填滿分子軌域 (Lowest Unoccupied Molecular Orbital, LUMO)，因為外加電場所造成的電位差，使得載子在有機薄膜中移動，進而在發光層結合形成電子-電洞對(Electron-Hole Pairs)，並產生再結合發光。第6頁/共58頁 201000484 常見之電洞傳導材料（hole transport materials) —般具有高載子遷移率（carrier mobility)的特性。然而，大部分電洞傳導材料卻有著玻璃轉化溫度（Tg)偏低的缺陷。由於〇el元件長時間操作時會產生過多的焦耳熱，使得元件操作溫度常會超過電洞傳導材料的Tg。g操作溫度上升至接近電洞傳導材料之Tg且持續一段時間後，將造成電洞傳導材料產生再結晶的現象，導致元件的發光衰減，壽命減少。有鑑於此，仍有需要開發新的電洞傳導材料，以提高熱穩定性及降低電洞傳導層與陽極界㈣能階差，藉此延長元件使用哥命、提高發光效率。【發明内容】鑒於上述之發明背景中’為了符合產業上之要求，本發明提供-種新的具有雜多環結構之共減合物及其在有機電激發光元件中的應用。【實施方式）本發明在此所探討的方向為-種具_多環結構之共輛化合201000484 IX. Description of the invention: [Technical field to which the invention pertains] The present invention relates to a composite compound having a heteropolycyclic structure and its use. ‘ 【Prior Art】 Iso-pyrrole heterocycles, due to their 4n+2; r-electron system and some aromatic properties, have caused one of the research topics of interest to synthetic and theoretical chemists. On the other hand, the isoindole pyrrole ring itself has some special properties, such as the tautomer equilibrium of the compound, the dilute nature of n, and the extreme non-going, for example, in acidic reaction conditions. The formation of conductive polymers, etc., has made the research of isoindole systems and similar heterocyclic compounds more and more important in the field of chemistry and materials. Organic ElectroLuminescence (OEL) 'has self-illumination, high response speed, wide viewing angle (over 160 degrees), power saving, high contrast and low cost, light weight, thin thickness, flexible west It can produce large area, high brightness, full color, etc. It is a star product in flat panel display. The principle of OEL illumination is that when a DC voltage is applied, the hole is injected from the anode into the highest Occupied Molecular Orbital (HOMO) of the hole conduction layer, and the electron is injected from the cathode into the lowest unfilled electron conduction layer. The lost area (Lowest Unoccupied Molecular Orbital, LUMO), because of the potential difference caused by the external electric field, causes the carrier to move in the organic film, and then combines to form an Electro-Hole Pairs in the luminescent layer, and recombines Glowing. Page 6 of 58 201000484 Common hole transport materials generally have the characteristics of high carrier mobility. However, most of the hole conducting materials have defects in which the glass transition temperature (Tg) is low. Due to the excessive Joule heat generated by the 〇el element during long-term operation, the operating temperature of the component often exceeds the Tg of the hole conducting material. When the operating temperature rises to near the Tg of the hole conducting material and continues for a period of time, it will cause recrystallization of the hole conducting material, resulting in attenuation of the light emission of the component and a decrease in lifetime. In view of this, there is still a need to develop new hole conducting materials to improve thermal stability and reduce the energy difference between the hole conducting layer and the anode boundary (4), thereby extending the use of the components and improving the luminous efficiency. SUMMARY OF THE INVENTION In view of the above-described background of the invention, the present invention provides a novel co-compound having a heteropolycyclic structure and its use in an organic electroluminescent device in order to meet industrial requirements. [Embodiment] The present invention is directed to a common vehicle combination of a multi-ring structure.

物及其應用。灸7 , t A 為了此徹底地瞭解本發明，將在下詳盡的製程步觫+ , 田IT捉 *·或組成結構。顯然地，本發明該領域之技缻I不取疋7、 ^所熟習的特殊細節。另—方面，眾所周4 + :=Γ未一…以避免造成本發明;二之限之外，本佳體系會詳細描述如下’然而除了這些詳細描述還可以廣泛地施行在其他的體系中，且本發明的範第7頁/共58頁 201000484 圍不受限定，以其之後的專利範圍為準。本發明之第一實施例揭露一種具有雜多環結構之共辄化合物，上述具有雜多環結構之共軛化合物的一般結構如下： R12Objects and their applications. Moxibustion 7, t A In order to thoroughly understand the present invention, the following detailed steps will be carried out, and the IT will capture or construct the structure. Obviously, the technique of the present invention in this field does not take the specific details familiar to it. On the other hand, the public is 4 + : = not ... to avoid causing the invention; in addition to the second limit, the best system will be described in detail below 'however, in addition to these detailed descriptions can be widely implemented in other systems And the scope of the patents of the present invention is not limited, and the scope of the following patents shall prevail. The first embodiment of the present invention discloses a conjugated compound having a heteropolycyclic structure, and the general structure of the above conjugated compound having a heteropolycyclic structure is as follows: R12

其中，A係選自S、N等原子’ A可以更包含一取代基。上述結構中的R1〜R19可以相同或不同，且R1〜R19係獨立選自下列族群中之一者：氫原子、鹵素原子（例如：氟、氯、溴、碘）；芳香基；鹵素取代的芳香基；C1-C20鹵烷基取代的芳香基；芳香炫 * 基；芳香烯基；C1_C20鹵烧基取代的芳香烧基；具芳香基取代的 • C1-C20烷基；C1-C20烷基、C1-C20環烷基（例如：甲基、乙基、丁基、環己基）；C1-C20 烷氧基（alkoxy group);胺基（amino group);具芳香基取代的胺基；具Cl -C20烧基取代的胺基’亞石肖酸基（nitroso group);硝基（nitro group);幾·基（carbonyl group); 氰基(cyano group，-CN);具有取代基的芳香胺基；雜環基團；具有環狀的胺基(piperidine，morpholine)。在根據本實施例之一較佳範例中，當上述具有雜多環結構之第8頁/共58頁 201000484 共軛化合物中之A係表示一 N原子時，N之取代基係選自下列群組中之一者，然而N之取代基並不以下列群組為限：Wherein A is selected from atoms such as S and N, and A may further comprise a substituent. R1 to R19 in the above structure may be the same or different, and R1 to R19 are independently selected from one of the following groups: a hydrogen atom, a halogen atom (e.g., fluorine, chlorine, bromine, iodine); an aromatic group; a halogen-substituted one Aromatic group; C1-C20 haloalkyl-substituted aryl group; aromatic aryl group; aromatic alkenyl group; C1_C20 halogen group-substituted aromatic alkyl group; aryl-substituted C1-C20 alkyl group; C1-C20 alkyl group , a C1-C20 cycloalkyl group (e.g., methyl, ethyl, butyl, cyclohexyl); a C1-C20 alkoxy group; an amino group; an amine group substituted with an aryl group; Cl-C20 alkyl-substituted amine nitroso group; nitro group; carbonyl group; cyano group (-CN); aromatic having a substituent Amino group; heterocyclic group; having a cyclic amino group (piperidine, morpholine). In a preferred embodiment according to the present embodiment, when the A group of the above-mentioned conjugated compound having a heteropolycyclic structure of 8th page/58 of 201000484 represents an N atom, the substituent of N is selected from the group consisting of One of the groups, however the substituents of N are not limited to the following groups:

在根據本實施例之一較佳範例中，上述具有雜多環結構之共輛化合物中相鄰之R2與R3、R4與R5、R5與R6、R6與R7、R7與、P、9 與 R10、R10 與 R11、R11 與 R12、R12 與 R13、R15 與 R16、R18 與R19等至少有一組可以是形成一芳香環、一芳香雜環、一環烯基或是一雜環烯基之任意原子團。上述的芳香環、芳香雜環、環烯基或是雜環烯基等可以分別是五元環、六元環、或是七元環，且上述之芳香環、芳香雜環、環烯基或是雜環烯基等可以更包含一個或多個取代基。上述之取代基可以相同或不同，且上述取代基係獨立選自下列族群中之一者：氫原子、函素原子（例如：氟、氯、溴、碘）、芳香基、鹵素取代的芳香基、鹵素取代的芳香烷基、第9頁/共58頁 201000484 鹵烷基取代的芳香基、鹵烷基取代的芳香烷基、芳香基取代的 C1-C20 烷基、C1-C20 烷基、C1-C20 環烷基、C1-C20 烷氧基（aik〇Xy group)、C1-C20取代的胺基(amino group)、具有取代基的芳香胺基[例如苯胺基（aniline)]、亞硝酸基(nitroso)、硝基(nitro)、羰基 (carbonyl)、氰基（cyano，-CN)、鹵素取代的C1-C20烧基（例如 » 三氟甲烷基，CF3)、雜環取代基團。上述R2〜R19中未成環之取代基可以相同或不同，且上述R2〜 R19中未成環之取代基係獨立選自下列族群之一者：氫原子、鹵素原子、C1-C20 烧基（alkyl group)、C1-C20 環院基、烧氧基(alkoxyl group)、_素取代的C1-C20烧基、C1-C20取代的胺基（amino group)、C1-C20 醢基（acyl group)、C1-C20 醋基（ester group)、Cl-C20 醯胺基(amide group)、芳香基、鹵素取代的芳香基、鹵素取代的芳香烷基、芳香基取代的烯基、_烷基取代的芳香基、鹵烷基取代的芳香烧基、氰基(cyano)、破基(nitro)、共輛芳香環基團（aromatic group)、芳香雜環基團。根據本實施例，前述之芳香基團可以是包含苯基(phenyl)、萘基（naphthyl)、聯苯基（diphenyl)、蒽基（anthryl)、苯并菲基 (pyrenyl)、菲基(phenanthryl)與苐基（fluorenyl)或其他形式之多苯環取代基。前述的環稀基團包含環己烯（cyclohexene)、環己二烯 (cyclohexadiene)、環戊稀（cyclopentene)與環戊二烯 (cyclopentadiene)或其他形式之環烯。前述之雜環基團包括哌喃第10頁/共58頁 201000484 (pyrane)、旅洛琳(pyrroline)、α夫喃（furan)、苯并咬喃（benzofuran)、嗟吩（thiophene)、苯并嗟吩（benzothiophene)比咬（pyridine)、°|：琳（quinoline)、異啥琳（isoquinoline)、°比嗪（pyrazine)、嘴口定 (pyrimidine)、11比略（pyrrole)、aite^pyrazole)、口米唾（imidazole)、0引嗓（indole)、嗟°坐(thiazole)、異嗟》坐（isothiazole)、°惡°坐（oxazole)、異"惡嗤（isoxazole)、苯并嗟坐（benzothiazole)、苯并°惡口坐 (benzoxazole)、二氮菲（phenanthroline)或其他形式之雜環。在根據本實施例之一較佳範例中，上述具有雜多環結構之共輛化合物之結構式如下：In a preferred embodiment according to the present embodiment, the adjacent R2 and R3, R4 and R5, R5 and R6, R6 and R7, R7 and P, 9 and R10 of the common compound having a heteropolycyclic structure And at least one group of R10 and R11, R11 and R12, R12 and R13, R15 and R16, R18 and R19 may be any atomic group forming an aromatic ring, an aromatic heterocyclic ring, a monocycloalkenyl group or a heterocycloalkenyl group. The above aromatic ring, aromatic heterocyclic ring, cycloalkenyl group or heterocycloalkenyl group may be a five-membered ring, a six-membered ring or a seven-membered ring, respectively, and the above aromatic ring, aromatic heterocyclic ring, cycloalkenyl group or It is a heterocyclic alkenyl group or the like which may further contain one or more substituents. The above substituents may be the same or different, and the above substituents are independently selected from one of the following groups: a hydrogen atom, a functional atom (for example, fluorine, chlorine, bromine, iodine), an aromatic group, a halogen-substituted aromatic group. , halogen-substituted arylalkyl, page 9 of 58 pages 201000484 haloalkyl substituted aryl, haloalkyl substituted arylalkyl, aryl substituted C1-C20 alkyl, C1-C20 alkyl, C1 -C20 cycloalkyl, C1-C20 alkoxy (aik〇Xy group), C1-C20 substituted amino group, substituted aromatic amine group [eg aniline], nitrite group (nitroso), nitro, carbonyl, cyano (-CN), halogen-substituted C1-C20 alkyl (eg, »trifluoromethyl, CF3), heterocyclic substituent. The unsubstituted substituents in the above R2 to R19 may be the same or different, and the unsubstituted substituents in the above R2 to R19 are independently selected from one of the following groups: a hydrogen atom, a halogen atom, a C1-C20 alkyl group (alkyl group). ), C1-C20 ring-based, alkoxyl group, _-substituted C1-C20 alkyl, C1-C20 substituted amino group, C1-C20 acyl group, C1 -C20 ester group, Cl-C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted arylalkyl group, aryl-substituted alkenyl group, _alkyl-substituted aryl group A haloalkyl-substituted aromatic alkyl group, a cyano group, a nitro group, a total aromatic group, and an aromatic heterocyclic group. According to this embodiment, the aforementioned aromatic group may be composed of a phenyl group, a naphthyl group, a diphenyl group, an anthryl group, a pyryryl group, a phenanthryl group. And fluorenyl or other forms of polyphenyl ring substituents. The aforementioned ring-thin groups include cyclohexene, cyclohexadiene, cyclopentene and cyclopentadiene or other forms of cycloolefin. The aforementioned heterocyclic group includes piperene page 10 / total 58 pages 201000484 (pyrane), pyroline (pyrroline), alpha furan, benzofuran, thiophene, benzene And benzothiophene than pyridine, °|: quinoline, isoquinoline, pyrazine, pyrimidine, 11 pyrrole, aite^ Pyrazole), imidazole, indole, thiazole, isothiazole, oxazole, oxazole, isoxazole, benzene And benzothiazole, benzoxazole, phenanthroline or other forms of heterocyclic ring. In a preferred embodiment according to this embodiment, the structural formula of the above-mentioned compound having a heteropolycyclic structure is as follows:

其中’上述結構中的R1〜R2!可以相同或不同，且R1〜r21 係獨立選自下列族群中之一者：氫原子、氧原子、鹵素原子（例如：氟、氯、漠、硬）；芳香基；幽素取代的芳香基；Cl_C2〇齒烧基取代的芳香基；芳香烷基；芳香烯基；C1-C20鹵烷基取代的芳香烷基；具芳香基取代的C1-C20烷基；C1-C20烷基、C1-C20環烷基（例如：曱基、乙基、丁基、環己基）；C1-C20烷氧基（alkoxy gr〇UP);胺基（amino group);具芳香基取代的胺基；具C1_C20 第1〗頁/共58頁 201000484 烧基取代的胺基；亞确酸基(nitrosogroup);确基(nitrogroup);幾基（carbonyl group);氰基（cyano group,-CN);具有取代基的芳香胺基；雜環基團；具有環狀的胺基(piperidine，morpholine) 〇上述具有雜多環結構之共輛化合物中相鄰之R2與R3、R4與 R5、R5 與 R6、R6 與 R7、R7 與 R9 與 Rl〇、Rl0 與 Rll、Ru 與 • R12、R12與R13、Ri5與R16、R18與R19等至少有一組可以是形成一芳香環、一芳香雜環、一環烯基或是一雜環烯基之任意原子團。上述的芳香環、芳香雜環、環烯基或是雜環烯基等可以分別是五元環、六元環、或是七元環，且上述之芳香環、芳香雜環、環稀基或是雜每烯基等可以更包含一個或多個取代基。上述之取代武可以相同或不同，且上述取代基係獨立選自下列族群中之_者. 氫原子、氧原子、鹵素原子（例如：氟、氣、溴、碘）、芳香基、鹵素取代的芳香基、i素取代的芳香烷基、il烷基取代的芳香基、鹵烷基取代的芳香烷基、芳香基取代的C1-C20烷基、C1-C2Q ^ 基、C1-C20 J哀烧基、C1-C20 烧氧基（alkoxy group)、Cl~C2〇取代的胺基（amino group)、具有取代基的芳香胺基[例如笨胺武 (aniline)] ' 亞硝’酸基（nitroso)、硝基（nitro)、幾基（carbonyl)、& 基（cyano，-CN)、鹵素取代的C1-C20烷基（例如三氟甲燒義 CFO、雜環取代基團。上述R2〜R19中未成環之取代基可以相同或不同，且上述汉2〜 R19中未成環之取代基係獨立選自下列族群之一者：氳原子、鹵素第12頁/共58頁 201000484 原子、C1-C20 烷基（alkyl group)、C1-C20 環烷基、烷氧基（alkoxyl group)、鹵素取代的C1-C20烷基、CM-C20取代的胺基（amino group)、C1-C20 酿基（acyl group)、C1-C20 酉旨基（ester group)、C1- C20 醯胺基(amide group)、芳香基、鹵素取代的芳香基、鹵素取代的芳香烷基、芳香基取代的烯基、！|烷基取代的芳香基、鹵烷基取代的芳香烷基、氰基(cyano)、硝基(nitro)、共軛芳香環基團 (aromatic group)、芳香雜環基團。在根據本實施例之另一較佳範例中，上述具有雜多環結構之共車厄化合物之結構式如下：Wherein R1 to R2! in the above structure may be the same or different, and R1 to r21 are independently selected from one of the following groups: a hydrogen atom, an oxygen atom, a halogen atom (for example, fluorine, chlorine, desert, hard); Aromatic group; crypto-substituted aromatic group; Cl_C2 dentate-substituted aromatic group; arylalkyl group; aromatic alkenyl group; C1-C20 haloalkyl-substituted arylalkyl group; aryl-substituted C1-C20 alkyl group C1-C20 alkyl, C1-C20 cycloalkyl (eg, decyl, ethyl, butyl, cyclohexyl); C1-C20 alkoxy (alkoxy gr〇UP); amino group; Aromatic substituted amine; C1_C20 Page 1 / 58 pages 201000484 Alkyl substituted amine; nitrosogroup; nitrogroup; carbonyl group; cyano Group, -CN); a substituted amine group; a heterocyclic group; a cyclic amino group (piperidine, morpholine) 相邻 adjacent R2 and R3, R4 in a compound having a heteropolycyclic structure And R5, R5 and R6, R6 and R7, R7 and R9 and Rl〇, Rl0 and Rll, Ru and • R12, R12 and R13, Ri5 and R16, R18 and R19, etc. A rare group may be any atomic group forming an aromatic ring, an aromatic heterocyclic ring, a monocycloalkenyl group or a heterocycloalkenyl group. The above aromatic ring, aromatic heterocyclic ring, cycloalkenyl group or heterocycloalkenyl group may be a five-membered ring, a six-membered ring or a seven-membered ring, respectively, and the above aromatic ring, aromatic heterocyclic ring, ring-dense group or It is a hetero-alkenyl group or the like which may further contain one or more substituents. The above substituted moieties may be the same or different, and the above substituents are independently selected from the group consisting of hydrogen atoms, oxygen atoms, halogen atoms (for example, fluorine, gas, bromine, iodine), aryl groups, halogen substitutions. Aromatic group, i-substituted arylalkyl group, il alkyl-substituted aryl group, haloalkyl-substituted arylalkyl group, aryl-substituted C1-C20 alkyl group, C1-C2Q^ group, C1-C20 J smoldering Base, C1-C20 alkoxy group, Cl~C2〇 substituted amino group, substituted aromatic amine group [eg aniline] 'nitrite' acid group (nitroso) , nitro, carbonyl, & cyano, -CN, halogen-substituted C1-C20 alkyl (eg, trifluoromethyl CFO, heterocyclic substituent. R2~ The unsubstituted substituents in R19 may be the same or different, and the unsubstituted substituents in the above Han 2 to R19 are independently selected from one of the following groups: ruthenium atom, halogen page 12 / total 58 pages 201000484 atom, C1- C20 alkyl group, C1-C20 cycloalkyl, alkoxyl group, halogen-substituted C1-C20 alkyl, CM- C20 substituted amino group, C1-C20 acyl group, C1-C20 ester group, C1-C20 amide group, aryl group, halogen-substituted aryl group , halogen-substituted arylalkyl, aryl-substituted alkenyl, !|alkyl-substituted aryl, haloalkyl-substituted arylalkyl, cyano, nitro, conjugated aromatic ring An aromatic group, an aromatic heterocyclic group. In another preferred embodiment according to this embodiment, the structural formula of the above-mentioned common compound having a heteropolycyclic structure is as follows:

如·氣、氣、演、碘）；芳香基；齒素取代的芳香基；C1-C20鹵院基取代的芳香基；芳香烧基；芳香稀基；C1-C2G ||烧基取代的芳香烧基’具芳香基取代的C1-C20烷基；C1-C20烷基、C1-C20環烷基（例如：甲基、乙基、丁基、環己基）；C1-C20烷氧基（alkoxy group) ’胺基（amin〇 gr〇up);具芳香基取代的胺基；具ci c2〇第13頁/共58頁 201000484 烧基取代的胺基，亞確酸基(nitrile group);硝基(nitro group);幾基（carbonyl group );氰基(cyano group，_CN);具有取代基的芳香胺基，雜環基團’具有環狀的胺基(piperidine，morpholine)。上述具有雜多環結構之共車厄化合物中相鄰之R2與R3、R4與 R5、R5 與 R6、R6 與、R7 與 r8、r9 與 Rl〇、Rl〇與 r11、Rll 與 R12、R12 與 R13、R15 與 Ri6、與 Rl9、r22 與 r23、r24 與 r25、 R25 與 R26、R26 與 R”、r27 與 r28、r29 與 r30、r3〇與 r31、r31 與 R32、R32與R33、尺35與R36等至少有一組可以是形成一芳香環、一芳香雜環、一環烯基或是一雜環烯基之任意原子團。上述的芳香環、芳香雜環、環烯基或是雜環烯基等可以分別是五元環、六元環、或是七7C環，且上述之芳香環、芳香雜環、環烯基或是雜環烯基等可以更包含一個或多個取代基。上述之取代基可以相同或不同，且上述取代基係獨立選自下列族群中之一者：氫原子、氧 -原子、鹵素原子（例如：氟、氣、溴、碘）、芳香基、鹵素取代的芳香基、鹵素取代的芳香烷基、鹵烷基取代的芳香基、齒烷基取代的芳香烷基、芳香基取代的C1_C2〇烷基、C1_C2〇烷基、cl_C2〇 i哀烧基、C1-C20烷氧基（aikoxy group)、C〗_C2〇取代的胺基（amin〇 group)、具有取代基的芳香胺基[例如苯胺基、亞硝酸基(nitroso)、確基(nitro)、羰基（carb〇nyi)、氰基（cyan〇, CN)、鹵素取代的C1-C20烷基（例如三氟甲烷基，CF3)、雜環取代基團。上述R2〜R36中未成環之取代基可以相同或不同，且上述R2〜第14頁/共58頁 201000484 R36中未成環之取代基係獨立選自下列族群之一者：氫原子、鹵素原子、C1-C20 烷基(alkyl group)、C1-C20 環烷基、烷氧基(alkoxyl group)、鹵素取代的C1-C20烧基、C1-C20取代的胺基（amino group)、C1-C20 醯基（acyl group)、Cl-C20 酯基（ester group)、Cl-C20 醯胺基(amide group)、芳香基、鹵素取代的芳香基、鹵素取代的芳香烷基、芳香基取代的烯基、_烷基取代的芳香基、鹵烷基取代的芳香烷基、氰基(cyano)、硝基(nitro)、共輛芳香環基團（aromatic group)、芳香雜環基團。在根據本實施例之另一較佳範例中，上述具有雜多環結構之共輛化合物之結構式如下：Such as qi, gas, and iodine; aryl; aryl substituted aryl; C1-C20 halogen-substituted aryl; aromatic alkyl; aromatic dilute; C1-C2G || Alkyl-substituted C1-C20 alkyl; C1-C20 alkyl, C1-C20 cycloalkyl (eg methyl, ethyl, butyl, cyclohexyl); C1-C20 alkoxy (alkoxy) Group) 'amino group (amin〇gr〇up); amine group substituted with an aryl group; with ci c2 〇 page 13 / total 58 pages 201000484 alkyl group substituted amine group, nitrile group (nitrile group); A nitro group; a carbonyl group; a cyano group (_CN); an aromatic amine group having a substituent, the heterocyclic group having a cyclic phenoline (morpholine). The above-mentioned R2 and R3, R4 and R5, R5 and R6, R6 and R7 and r8, r9 and Rl〇, Rl〇 and r11, R11 and R12, R12 are in the common compound having a heteropolycyclic structure. R13, R15 and Ri6, and Rl9, r22 and r23, r24 and r25, R25 and R26, R26 and R", r27 and r28, r29 and r30, r3〇 and r31, r31 and R32, R32 and R33, ruler 35 At least one group of R36 or the like may be any atomic group forming an aromatic ring, an aromatic heterocyclic ring, a monocycloalkenyl group or a heterocycloalkenyl group. The above aromatic ring, aromatic heterocyclic ring, cycloalkenyl group or heterocycloalkenyl group, etc. It may be a five-membered ring, a six-membered ring, or a seven-seven-C-ring, respectively, and the above aromatic ring, aromatic heterocyclic ring, cycloalkenyl group or heterocycloalkenyl group may further contain one or more substituents. The groups may be the same or different, and the above substituents are independently selected from one of the following groups: a hydrogen atom, an oxygen atom, a halogen atom (for example, fluorine, gas, bromine, iodine), an aromatic group, a halogen-substituted aromatic group. , halogen-substituted arylalkyl, haloalkyl-substituted aryl, dentate-substituted aromatic Base, aryl substituted C1_C2 decyl, C1_C2 decyl, cl_C2〇i sulphonate, C1-C20 alkoxy group, C _C2 〇 substituted amine (amin〇 group), substituted Aromatic amine group (eg, anilino, nitroso, nitro, carb〇nyi, cyan〇, CN, halogen-substituted C1-C20 alkyl (eg, three) Fluoromethylalkyl, CF3), heterocyclic substituent group. The unsubstituted substituents in the above R2 to R36 may be the same or different, and the unsubstituted substituents in the above R2~14/58 page 201000484 R36 are independently selected. From one of the following groups: hydrogen atom, halogen atom, C1-C20 alkyl group, C1-C20 cycloalkyl group, alkoxyl group, halogen-substituted C1-C20 alkyl group, C1-C20 Substituted amino group, C1-C20 acyl group, Cl-C20 ester group, Cl-C20 amide group, aryl group, halogen-substituted aryl group, halogen Substituted arylalkyl, aryl substituted alkenyl, _alkyl substituted aryl, haloalkyl substituted aryl, cyano, nitro Nitro), a total of aromatic group, aromatic heterocyclic group. In another preferred embodiment according to this embodiment, the structural formula of the above-mentioned compound having a heteropolycyclic structure is as follows:

其中，上述結構中的R1 ~ R20可以相同或不同，且R丨〜R20 係獨立選自下列族群中之一者：氫原子、鹵素原子（例如：氟、氯 '溴、碘）；芳香基；鹵素取代的芳香基；C1-C20鹵烷基取代的芳香基；芳香烷基；芳香烯基；C1-C20鹵烷基取代的芳香烷基；具芳香基取代的C1-C20烷基；C1-C20烷基、C1-C20環烷基（例如.甲基、乙基、丁基、環己基）；Cl -C20烧氧基（alkoxy group); 第15頁/共58頁 201000484 胺基（amino group);具芳香基取代的胺基；具C1-C20烷基取代的胺基：亞確酸基(nitrile group);硝基(nitro group);徵基（carbonyl group);氰基(cyano group，-CN);具有取代基的芳香胺基；雜環基團，具有環狀的胺基（piperidine，morpholine);石黃胺基團 (sulfonamide)、對甲苯績胺基團（p_t〇luenesulfonamide)、苯績胺基團（benzenesulfonamide);胺曱酸或乙酸酯（methyl or ethyl carbamate) ° 上述具有雜多環結構之共軛化合物中之R20可以是選自下列群組中之一者，然而R2G並不以下列群組為限：Wherein R1 to R20 in the above structure may be the same or different, and R丨~R20 are independently selected from one of the following groups: a hydrogen atom, a halogen atom (for example, fluorine, chlorine 'bromine, iodine); an aromatic group; Halogen-substituted aryl; C1-C20 haloalkyl-substituted aryl; arylalkyl; aromatic alkenyl; C1-C20 haloalkyl-substituted arylalkyl; aryl-substituted C1-C20 alkyl; C20 alkyl, C1-C20 cycloalkyl (eg. methyl, ethyl, butyl, cyclohexyl); Cl-C20 alkoxy group; page 15 of 58 201000484 amino group An amine group substituted with an aryl group; an amine group substituted with a C1-C20 alkyl group: a nitrile group; a nitro group; a carbonyl group; a cyano group; -CN); an aromatic amine group having a substituent; a heterocyclic group having a cyclic amino group (piperidine, morpholine); a sulfonamide group; a p-toluenesulfonamide group; Benzenesulfonamide; methyl or ethyl carbamate ° conjugated with heteropolycyclic structures The compositions may be selected from the group R20 in one of those, however, R2G is not limited to the following groups:

上述具有雜多環結構之共軛化合物中相鄰之R2與R3、R4與 R5、R5 與 R6、R6 與 R7、R7 與 R8、R9 與 R10、Rl〇與 R11、R11 與 R12、與R13、R15與R16、R18與R19等至少有一組可以是形成一第16頁/共58頁 201000484 芳香環、一芳香雜環、一環烯基或是一雜環婦基之任意原子團。上述的芳香環、芳香雜環、環烯基或是雜環烯基等可以分別是五元環、六元環、或是七元環’且上述之芳香環、芳香雜環、環烯基或是雜環烯基等可以更包含一個或多個取代基。上述之取代基可以相同或不同，且上述取代基係獨立選自下列族群中之一者：氫原子、鹵素原子（例如：氟、氣、溴、碘）、芳香基、鹵素取代的芳香基、i素取代的芳香烷基、鹵烷基取代的芳香基、_烷基取代的芳香烷基、芳香基取代的C1-C20烷基、C1-C20烷基、C1-C20 環炫基、C1-C20 炫* 氧基（alkoxy group)、Cl-C20 取代的胺基(amino group)、具有取代基的芳香胺基[例如苯胺基（aniline)]、亞确酸基(nitrile)、硝基(nitro)、幾基（carbonyl)、氰基(cyano, -CN)、鹵素取代的C1-C20烷基（例如三氟曱烷基，CF3)、雜環取代基團。上述R2〜R19中未成環之取代基可以相同或不同，且上述R2〜 R19中未成環之取代基係獨立選自下列族群之一者：氫原子、鹵素原子、C1-C20 炫基（alkyl group)、C1-C20 環烧基、烧氧基(alkoxyl group)、鹵素取代的C1-C20烷基、C1-C20取代的胺基（amino gr〇up)、Cl-C20 酿基（acyl group)、CM_C20 酯基（ester group)、Cl-C20 醢胺基(amide group)、芳香基、鹵素取代的芳香基、鹵素取代的芳香烷基、芳香基取代的烯基、鹵烷基取代的芳香基、#烷基取代的芳香烧基、氰基(cyano)、石肖基(nitro)、共輛芳香環基團（aromatic group)、芳香雜環基團；續胺基團（sulfonamide)、對甲苯確胺基第17頁/共58頁 201000484 團（p-toluenesulfonamide)、苯績胺基團（benzenesulfonamide);胺曱酸或乙酸醋（methyl or ethyl carbamate)。在根據本實施例之另一較佳範例中，上述具有雜多環結構之共軛化合物之結構式如下：Among the above conjugated compounds having a heteropolycyclic structure, adjacent R2 and R3, R4 and R5, R5 and R6, R6 and R7, R7 and R8, R9 and R10, R1〇 and R11, R11 and R12, and R13, At least one of R15 and R16, R18 and R19 may be any atomic group forming a 16th page/58th page of 201000484 aromatic ring, an aromatic heterocyclic ring, a monocycloalkenyl group or a heterocyclic group. The above aromatic ring, aromatic heterocyclic ring, cycloalkenyl group or heterocycloalkenyl group may be a five-membered ring, a six-membered ring or a seven-membered ring, respectively, and the above aromatic ring, aromatic heterocyclic ring, cycloalkenyl group or It is a heterocyclic alkenyl group or the like which may further contain one or more substituents. The above substituents may be the same or different, and the above substituents are independently selected from one of the following groups: a hydrogen atom, a halogen atom (for example, fluorine, gas, bromine, iodine), an aromatic group, a halogen-substituted aromatic group, I-substituted arylalkyl, haloalkyl-substituted aryl, _alkyl-substituted arylalkyl, aryl-substituted C1-C20 alkyl, C1-C20 alkyl, C1-C20 cycloH, C1- C20 al* oxy (alkoxy group), Cl-C20 substituted amino group, substituted aromatic amine group [eg aniline], nitrile (nitrile), nitro (nitro ), carbonyl, cyano (-CN), halogen-substituted C1-C20 alkyl (eg, trifluoroalkyl, CF3), heterocyclic substituent. The unsubstituted substituents in the above R2 to R19 may be the same or different, and the unsubstituted substituents in the above R2 to R19 are independently selected from one of the following groups: a hydrogen atom, a halogen atom, and a C1-C20 炫 group. ), C1-C20 cycloalkyl, alkoxyl group, halogen-substituted C1-C20 alkyl, C1-C20 substituted amino group, Cl-C20 acyl group, CM_C20 ester group, Cl-C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted arylalkyl group, aryl-substituted alkenyl group, haloalkyl-substituted aryl group, #alkyl-substituted aromatic alkyl, cyano, nitro, aromatic group, aromatic heterocyclic group; sulfonamide, p-toluene-based Page 17 of 58 201000484 Group (p-toluenesulfonamide), benzenesulfonamide; methyl or ethyl carbamate. In another preferred embodiment according to this embodiment, the structural formula of the above conjugated compound having a heteropolycyclic structure is as follows:

係獨立選自下列族群中之一者：氫原子、鹵素原子（例如：氟、氣、溴、碘）；芳香基；鹵素取代的芳香基；C1-C20鹵烷基取代的芳香基；芳香烷基；芳香烯基；C1-C20鹵烷基取代的芳香烷基；具芳香基取代的C1-C20烷基；C1-C20烷基、C1-C20環烷基（例如：甲基、乙基、丁基、環己基）；C1-C20烷氧基（alkoxy group); 胺基（amino group);具芳香基取代的胺基；具C1-C20烧基取代的胺基；亞硝酸基(nitrile group);瑞基(nitro group);叛基（carbonyl group);氰基(cyano group，-CN);具有取代基的芳香胺基；雜環基團；具有環狀的胺基（piperidine，morpholine);續胺基團 (sulfonamide)、對甲苯績胺基團（p-toluenesulfonamide)、苯石黃胺基團（benzenesulfonamide);胺曱酸或乙酸酉旨（methyl or ethyl carbamate) 〇第18頁/共58頁 201000484 上述具有雜多環結構之共軛化合物中之R37可以是選自下列群組中之一者，然而R37並不以下列群組為限：Is independently selected from one of the following groups: a hydrogen atom, a halogen atom (eg, fluorine, gas, bromine, iodine); an aromatic group; a halogen-substituted aromatic group; a C1-C20 haloalkyl-substituted aromatic group; an aromatic alkane Aromatic alkenyl; C1-C20 haloalkyl substituted arylalkyl; aryl substituted C1-C20 alkyl; C1-C20 alkyl, C1-C20 cycloalkyl (eg methyl, ethyl, Butyl, cyclohexyl); C1-C20 alkoxy group; amino group; amine group substituted with an aryl group; amine group substituted with C1-C20 alkyl group; nitrite group ); nitro group; carbonyl group; cyano group (-CN); aromatic amine group having a substituent; heterocyclic group; having a cyclic amino group (piperidine, morpholine) ; sulfonamide, p-toluenesulfonamide, benzenesulfonamide; methyl or ethyl carbamate 〇 page 18 / total 58 pages 201000484 R37 in the above conjugated compound having a heteropolycyclic structure may be one selected from the group consisting of R37 Not limited to the following groups:

VV

上述具有雜多環結構之共軛化合物中相鄰之R2與R3、R4與 R5、R5 與 R6、R6 與 R7、R7 與 R8、R9 與 R10、R10 與 R11、R11 與 R12、R12 與 R13、R15 與 R16、R18 與 R19、R22 與 R23、R24 與 R25、 R25 與 R26、R26 與 R27、R27 與 R28、R29 與 R30、R30 與 R31、R31 與 R32、R32與R33、R35與R36等至少有一組可以是形成一芳香環、一芳香雜環、一環稀基或是一雜環烯基之任意原子團。上述的芳香環、芳香雜環、環烯基或是雜環烯基等可以分別是五元環、六元環、或是七元環，且上述之芳香環、芳香雜環、環烯基或是雜環烯基等可以更包含一個或多個取代基。上述之取代基可以相同或不同，且上述取代基係獨立選自下列族群中之一者：氫原子、鹵第19頁/共58頁 201000484 素原子（例如：氟、氯、溴、碘）、芳香基、鹵素取代的芳香基、鹵素取代的芳香烷基、_烷基取代的芳香基、函烷基取代的芳香烷基、芳香基取代的C1-C20烷基、C1-C20烷基、C1-C20環烷基、 C1-C20 烧氧基（alkoxy group)、C1-C20 取代的胺基（amino group)、具有取代基的芳香胺基[例如苯胺基（aniline)]、亞硝酸基(nitrile)、硝’基(nitro)、獄基（carbonyl)、氰基(cyano, -CN)、鹵素取代的C1-C20烷基（例如三氟甲烷基，CF3)、雜環取代基團；績胺基團（sulfonamide)、對甲苯石黃胺基團（p-toluenesulfonamide)、苯續胺基團（benzenesulfonamide);胺甲酸或乙酸醋（methyl or ethyl carbamate) ° 上述R2 ~R36中未成環之取代基可以相同或不同，且上述R2〜R36 中未成環之取代基係獨立選自下列族群之一者：氫原子、鹵素原子、C1-C20 烷基（alkyl group)、C1-C20 環烷基、烷氧基（alkoxyl group)、鹵素取代的C1-C20烧基、C1-C20取代的胺基（amino ' group)、Cl-C20 醯基（acyl group)、Cl-C20S旨基（ester group)、Cl_C20 醢胺基(amide group)、芳香基、鹵素取代的芳香基、鹵素取代的芳香烷基、芳香基取代的烯基、鹵烷基取代的芳香基、i烷基取代的芳香烧基、氰基(cyano)、确基(nitro)、共輛芳香環基團（aromatic group)、芳香雜環基團；續胺基團（sulfonamide)、對甲苯績胺基團（p-toluenesulfonamide)、苯績胺基團（benzenesulfonamide);胺曱酸或乙酸醋（methyl or ethyl carbamate)。第20頁/共58頁 201000484 以下將敘明數種根據本實施例之具有雜多環結構之共軛化合物的較佳範例之結構及其形成方式，然而，本說明書之範圍應以其後的專利範圍為準，而不應以下列範例為限。Among the above conjugated compounds having a heteropolycyclic structure, adjacent R2 and R3, R4 and R5, R5 and R6, R6 and R7, R7 and R8, R9 and R10, R10 and R11, R11 and R12, R12 and R13, R15 and R16, R18 and R19, R22 and R23, R24 and R25, R25 and R26, R26 and R27, R27 and R28, R29 and R30, R30 and R31, R31 and R32, R32 and R33, R35 and R36, etc. The group may be any atomic group forming an aromatic ring, an aromatic hetero ring, a ring dilute group or a heterocycloalkenyl group. The above aromatic ring, aromatic heterocyclic ring, cycloalkenyl group or heterocycloalkenyl group may be a five-membered ring, a six-membered ring or a seven-membered ring, respectively, and the above aromatic ring, aromatic heterocyclic ring, cycloalkenyl group or It is a heterocyclic alkenyl group or the like which may further contain one or more substituents. The above substituents may be the same or different, and the above substituents are independently selected from one of the following groups: a hydrogen atom, a halogen, a 19th page, a total of 58 pages, a 201000484 atom (for example, fluorine, chlorine, bromine, iodine), Aromatic group, halogen-substituted aryl group, halogen-substituted arylalkyl group, _alkyl-substituted aryl group, functional alkyl-substituted arylalkyl group, aryl-substituted C1-C20 alkyl group, C1-C20 alkyl group, C1 -C20 cycloalkyl, C1-C20 alkoxy group, C1-C20 substituted amino group, substituted aromatic amine group [eg aniline], nitrite (nitrile) ), nitro, carbonyl, cyano (-CN), halogen-substituted C1-C20 alkyl (eg, trifluoromethyl, CF3), heterocyclic substituent; Sulfonamide, p-toluenesulfonamide, benzenesulfonamide; methyl or ethyl carbamate ° unsubstituted substituents in R2 to R36 The same or different, and the unsubstituted substituents in the above R2 to R36 are independently selected from the following One of the group: hydrogen atom, halogen atom, C1-C20 alkyl group, C1-C20 cycloalkyl group, alkoxyl group, halogen-substituted C1-C20 alkyl group, C1-C20 substituted Amino group, Cl-C20 acyl group, Cl-C20S ester group, Cl_C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted aromatic An alkyl group, an aryl substituted alkenyl group, a haloalkyl substituted aryl group, an i alkyl substituted aromatic alkyl group, a cyano group, a nitro group, a common aromatic group, An aromatic heterocyclic group; a sulfonamide, a p-toluenesulfonamide, a benzenesulfonamide; a methyl or ethyl carbamate. Page 20 of 58 pages 201000484 The structure of a preferred example of a conjugated compound having a heteropolycyclic structure according to this embodiment and its formation will be described below. However, the scope of the present specification should be followed by The scope of patents shall prevail and shall not be limited to the following examples.

OCH, h3coOCH, h3co

CH3CH3

Ph 第21頁/共58頁Ph Page 21 of 58

Ph 201000484Ph 201000484

PhPh

Example 1 形成 N-Substituted Thieno [2,3-c] pyrroles 及 N-SubstitutedExample 1 Forms N-Substituted Thieno [2,3-c] pyrroles and N-Substituted

Thieno[2,3-c:4,5-c’]dipyrroles 與 N-Substituted pyrroloindoles 之一般流程：第22頁/共58頁 201000484General procedure for Thieno[2,3-c:4,5-c']dipyrroles and N-Substituted pyrroloindoles: Page 22 of 58 201000484

參考上述反應式’在均勻攪拌的thiophene alkyl halide/pyrrol alkyl halide與aromatic amine溶於99.5%乙醇中加入三乙基胺 (triethylamine)。讓上述反應在室溫下攪拌約3 hr，然後加熱迴流約19〜30 hr。在上述反應過程中將會逐漸析出固體沈澱物。上述固體沈澱物於反應結束後可依序進行過濾與乾燥，以獲取粗產物 (N-substituted thieno[2,3-c]pyrroles 或 N-substituted thieno[2,3-c:4,5-c’]dipyrroles 或 N-substituted pyrroloindoles)。上述粗產物可進一步藉由管柱層析（ethyl acetate/hexane 或 CH2C12/Hexane)以進行純化。Referring to the above reaction formula, triethylamine was added to a uniformly stirred thiophene alkyl halide/pyrrol alkyl halide and aromatic amine dissolved in 99.5% ethanol. The above reaction was allowed to stir at room temperature for about 3 hr and then heated to reflux for about 19 to 30 hr. A solid precipitate will gradually precipitate during the above reaction. The above solid precipitate can be sequentially filtered and dried after completion of the reaction to obtain a crude product (N-substituted thieno[2,3-c]pyrroles or N-substituted thieno[2,3-c:4,5-c ']dipyrroles or N-substituted pyrroloindoles). The above crude product can be further purified by column chromatography (ethyl acetate/hexane or CH2C12/Hexane).

其中，上述反應式中的A係表示S原子或一具有取代基之N原子；X 係表示-鹵素原子，x可以是選自m财之—者。上述反應式中之护係選自下列族群中之一者：直鏈或支鏈烧基、芳香基團、或是一雜芳香環基團。Wherein A in the above reaction formula represents an S atom or a N atom having a substituent; X represents a halogen atom, and x may be selected from the group consisting of m. The protecting system in the above reaction formula is selected from one of the following groups: a linear or branched alkyl group, an aromatic group, or a heteroaromatic ring group.

Example 2 第23頁/共58頁 201000484Example 2 Page 23 of 58 201000484

la lb lc Id le If R6 Η H H H ch3 ch2ch3 R37 Η ch3 Cl OCH 3 CH3 H ig lh li ij lk R6 ch2ch3 ch2ch2ch3 ch2ch2ch3 c6H5 C6H5 R37 ch3 ch3 Cl H Cl 5-[4-(2,2-Diphenyl-vinyl)-phenyl]-5/T-thieno[253-c]pyrrole (la). Eluent for chromatography: EA/hex (1:9). Yield 51%, dark yellow solid, mp 166-168 °C. IR (neat), 2915, 2848, 1513, 1391, 1336, 1200, 1048, 879 cm'VH NMR (500 MHz, CDC13) δ 7.35-7.20 (m, 13H), 7.10 (d, J=1.5 Hz, 1H), 7.08 (d, J=8.5 Hz, 2H), 6.97 (s, 1H) 6.96 (d, J=5.5 Hz, 1H), 6.94 (d，J=5.5 Hz，1H); 13C NMR (125 MHz) δ 143.10, 142.95, 140.12, 139.29, 135.46, 133.99, 130.68, 130.29, 128.80, 128.64, 127.64, 127.61, 127.54, 126.93,126.84, 125.96, 120.51, 115.87, 107.93, 107.83; MS (El) m/z (relative intensity) 377 (M+, 100); HRMS (El) m/z calcd for C26Hi9NS 377.1238, found 377.1241 5-[4-(2,2-Di-/i-tolyl-vinyl)-phenyl]-5Jy-thieno[2,3-c]pyiT〇le (lb). Eluent for chromatography: EA/hex (1:9).Yield 61%, pale yellow solid, mp 212-214 °C. IR (neat), 3021, 2918, 1605, 1514, 1399, 1183, 907, 816 cm1; *H NMR (400 MHz, CDC13) δ 7.26-7.19 (m, 4H), 7.16 (d5 J=7.6 Hz, 2H), 7.13-7.08 (m, 8H), 6.97 (d, J=5.2 Hz, 1H), 6.92 (d, J=6.0 Hz, 2 H), 2.41 (s, 3H) 2.38 (s, 3H); 13C NMR (100 MHz, CDC13) δ 142.91, 140.58, 139.11, 137.46, 137.22, 135.83, 133.96, 130.56, 130.16, 129.44, 128.90, 127.48, 126.85, 125.92, 125.78, 第24頁/共58頁 201000484 120.50, 115.86, 107.95, 107.84, 21.29, 21.10; MS (El) m/z (relative intensity) 405 (M+,100); HRMS (El) m/z calcd for C28H23NS 405.1551, found 405.1541. 5-{4-[2,2-Bis-(4-chloro-phenyl)-vinyI]-phenyl}-5//-thieno[2,3-c]pyrrole (lc). Eluent for chromatography: EA/hex (1:9).Yield 49%，pale yellow solid, mp 196-198 °C. IR (neat), 3029, 2866, 1602, 1515, 1490, 1477, 1398, 1089, 831 cm·1; W NMR (400 MHz, CDC13) δ 7.32 (d, J=8.8 Hz, 2H), 7.27 (d, J=8.8 Hz, 2H), 7.24 (d, J=8.0 Hz, 2 H), 7.22-7.19 (m, 3H), 7.(s, 1H), 7.13-7.11 (m, 2H), 7.08 (d, J=8.4 Hz, 2H), 6.96 (d, /=5.2 Hz, 1H), 6.92 (s, 1H) 6.91 (d, J=52 Hz, 1H); ,3C NMR (100 MHz, CDC13) δ 141.25, 140.53, 139.67, 138.12, 134.76, 134.17, 133.79, 133.75, 131.73, 130.71, 129.19, 128.80, 128.50, 127.77, 127.11, 126.18, 120.61, 115.85, 107.89, 107.78; MS (El) m/z (relative intensity) 449 (M+4, 70), 447 (M+2, 25)，445 (M+, 100); HRMS (El) m/z calcd for C26H17C12NS 445.0459, found 445.0444. 5-{4-[2,2-Bis-(4-methoxy-phenyl)-vinyl]-phenyl}-5flr-thieno[2,3-c]pyrroIe (Id). Eluent for chromatography: EA/hex (l:9).Yield 64, dark yellow solid, mp 178-179 °C. IR (neat), 3030, 2954, 2834, 1605, 1513, 1438, 1342, 1244, 1177, 1032, 834 cm'1; !H NMR (400 MHz, CDC13) δ 7.26 (d, ^8.8 Hz, 2H), 7.21 (d, J=2.4 Hz, 1 H), 7.20 (d, J=4.0 Hz, 2 H), 7.13 (d, J=8.8 Hz, 2H), 7.09 (d, J=8.8 Hz, 3 H), 6.95 (d, J=5.6 Hz, 1H), 6.90 (d, J=5.6 Hz, 1H), 6.89 (s, 1H), 6.86 (d, J=5.2 Hz, 2H), 6.83 (d, J=6.4 Hz, 2H), 3.83 (s, 3H), 3.81(s, 3H); 13C NMR (100 MHz, CDC13) δ 159.40, 159.13, 142.30, 139.02, 136.16, 136.09, 134.03, 132.51, - 131.57, 130.50, 128.85, 126.85, 125.98, 124.89, 120.57, 115.89, 114.18, 113.64, 107.98, 107.88, 55.31, 55.22; MS (El) m/z (relative intensity) 437 (M+, 100); HRMS (El) m/z calcd for C28H23NO2S 437.1449, found 437.1452. 5-[4-(2,2-Di-/7-tolyl-vinyl)-phenyl]-4-methyl-5-flr-thieno[2^-c]pyrrole (le). Eluent for chromatography: EA/hex (1:9). Yield 47%, Orange solid, mp 160-162 °C. IR (neat), 3022, 2917, 2861, 1604, 1594, 1512, 1403, 1202, 825 cm'VHNMR (400 MHz, CDC13) δ 7.25 (d, J=8.0 Hz, 2H), 7.18 (d, J-8.0 Hz, 2H ), 7.15-7.14 (m, 8H), 6.94 (s, 1H), 6.94 (s, 1H), 6.88 (s, 1H), 6.82 (s, 1H), 2.40 (s, 3H), 2.37 (s, 6H);,3C NMR (100 MHz, CDC13) δ 143.42, 140.58, 138.36, 137.55, 137.31, 137.13, 136.84, 131.83, 130.13, 129.99, 129.46, 128.93, 127.52, 125.80, 125.37, 124.89, 123.28, 117.61, 115.72, 109.12, 21.29, 21.11, 12.10; MS (El) m/z 第25頁/共58頁 201000484 (relative intensity) 420 (M+l, 100), 419 (10), 404 (2); HRMS (El) m/z calcd for C29H25NS 419.1708, found 419.1688. 5- [4-[2,2-Dipheny-vinyl] -phenyl] -4-ethyl-5^f-thieno [2,3-c] pyrrole (If). Eluent for chromatography: EA/hex (1:9). Yield 43%, yellow solid, mp 122-124 °C. IR (neat), 3020， 2932, 1601，1598, 1369, 1182, 916 cm1; *11 NMR (400 MHz, CDC13) δ 7.40-7.32 (m，8H)， 7.38-7.35 (m, 2H), 7.12 (s, 2H), 7.03 (s, 1H) , 6.97 (d, J=5.6 Hz, 1H), 6.90 (d, J=5.2 Hz, 1H), 6.79 (s, 1H), 2.77 (q, J=7.6 Hz, 2H), 1.21 (t, J=7.6 Hz, 3H); 13C NMR (100 MHz, CDC13) δ. 143.53, 143.04, 139.98, 138.64, 136.72, 130.66, 130.23, 130.03, 128.76, 128.23, 127.71, 127.65, 127.56, 126.82, 125.77,124.81, 124.04, 123.48, 116.10, 109.24, 19.32, 14.03; MS (El) m/z (relative intensity) 405 (M+, 100), 391 (17), 390 (57); HRMS (El) m/z calcd for C28H23NS 405.1551, found 405.1555. 5-[4-(2,2-Di-p-tolyl-vinyl)-phenyl]-4-ethyl-5^T-thieno[23-c]pyrrole (lg). Eluent for chromatography: EA/hex (1:9).Yield 48%, Orange solid, mp 154-156 °C. IR (neat), 3022, 2968, 2922 1604, 1511, 1404, 1110, 814 cm1; *H NMR (400 MHz, CDC13) δ 7.25 (d, J=8.0 Hz, 2H),7.19- 7.09 (m, 10H), 6.92 (d, /=5.6 Hz, 1H), 6.89 (s, 1H) 6.88 (d, J=4.8 Hz, 1H), 6.78 (s, 1H), 2.77 (q, J=7.6 Hz, 2H), 2.41 (s, 3H), 2.37 (s, 3H); ,3C NMR (100 MHz, CDC13) δ 143.48, 140.56, 138.44, 137.58, 137.32, 137.08, 130.62, 130.13, 129.96, 129.46, 128.94, 127.55, 125.80, 124.77, 124.12, 123.46, 116.15, 109.29, 21.32, 21.13, 19.95, 14.06; MS (El) m/z (relative intensity) 434 (M+l, 100), 433 (4), 420 (17), 419 (56); HRMS (El) m/z calcd for C30H27NS 433.1864, found 433.1879. 5-[4-(2,2-Di-/)-tolyl-vinyl)-phenyI]-4-propyl-5H-thieno[2,3-c]pyrrole (lh). Eluent for chromatography: EA/hex (1:9). Yield 32%, light yellow solid, mp 122-124 °C. IR (neat), 3077, 2958, 2927 2869, 1604, 1586, 1403, 1111, 813 cm'1; *H NMR (400 MHz, CDC13) δ 7.24 (d, J=8.0 Hz, 2H), 7.16 (d, J=8.4 Hz, 4H ), 7.12 (d, J=9.2 Hz, 4H), 7.09 (d, J=8.8 Hz, 2H), 6.94 (s, 1H), 6.93(d, J=5.6 Hz, 1 H), 6.88 (d, J-4.8 Hz, 1H), 6.78 (s, 1H), 2.70 (t, J=7.6 Hz, 2H), 2.40 (s, 3H) 2.37 (s, 3H), 1.56 (sex, J=7.2 Hz, 2H), 0.85 (t, /=7.2 Hz, 3H); 13C NMR (100 MHz, CDCI3) δ 143.52, 140.55, 138.48, 137.58, 137.31, 137.09, 131.15, 130.16, 129.93, 129.40, 128.93, 127.55, 125.87, 124.73, 123.34, 122.80, 116.21, 109.38, 28.47, 22.88, 21.29, 21.11, 13.96; MS (El) m/z (relative intensity) 448 (M+l, 78), 419 (100); HRMS (El) m/z 第26頁/共58頁 201000484 calcd for C31H29NS 447.2021, found 447.2043. 5-{4-[2,2-Bis-(4-chloro-phenyl)-vinyl]-phenyl}-4-propyl-5^-thieno[2,3-c]pyrrole (li).La lb lc Id le If R6 Η HHH ch3 ch2ch3 R37 Η ch3 Cl OCH 3 CH3 H ig lh li ij lk R6 ch2ch3 ch2ch2ch3 ch2ch2ch3 c6H5 C6H5 R37 ch3 ch3 Cl H Cl 5-[4-(2,2-Diphenyl-vinyl) -phenyl]-5/T-thieno[253-c]pyrrole (la). Eluent for chromatography: EA/hex (1:9). Yield 51%, dark yellow solid, mp 166-168 °C. IR (neat ), 2915, 2848, 1513, 1391, 1336, 1200, 1048, 879 cm'VH NMR (500 MHz, CDC13) δ 7.35-7.20 (m, 13H), 7.10 (d, J=1.5 Hz, 1H), 7.08 (d, J = 8.5 Hz, 2H), 6.97 (s, 1H) 6.96 (d, J = 5.5 Hz, 1H), 6.94 (d, J = 5.5 Hz, 1H); 13C NMR (125 MHz) δ 143.10, 142.95, 140.12, 139.29, 135.46, 133.99, 130.68, 130.29, 128.80, 128.64, 127.64, 127.61, 127.54, 126.93, 126.84, 125.96, 120.51, 115.87, 107.93, 107.83; MS (El) m/z (relative intensity) 377 (M+, 100); HRMS (El) m/z calcd for C26Hi9NS 377.1238, found 377.1241 5-[4-(2,2-Di-/i-tolyl-vinyl)-phenyl]-5Jy-thieno[2,3 -c]pyiT〇le (lb). Eluent for chromatography: EA/hex (1:9).Yield 61%, pale yellow solid, mp 212-214 °C. IR (neat), 3021, 2918, 1605 , 1514, 1399, 1183, 907, 816 cm1; *H NMR (400 MHz, CDC13) δ 7.26-7.19 (m, 4H), 7.16 (d5 J=7.6 Hz, 2H), 7.13-7.08 (m, 8H) , 6.97 (d, J=5.2 Hz, 1H), 6.92 (d, J=6.0 Hz, 2 H), 2.41 (s, 3H) 2.38 (s, 3H); 13C NMR (100 MHz, CDC13) δ 142.91, 140.58, 139.11, 137.46, 137.22, 135.83, 133.96, 130.56, 130.16, 129.44, 128.90, 127.48, 126.85, 125.92, 125.78, page 24 of 58 pages 201000484 120.50, 115.86, 107.95, 107.84, 21.29, 21.10; MS ( El) m/z (relative intensity) 405 (M+,100); HRMS (El) m/z calcd for C28H23NS 405.1551, found 405.1541. 5-{4-[2,2-Bis-(4-chloro-phenyl) -vinyI]-phenyl}-5//-thieno[2,3-c]pyrrole (lc). Eluent for chromatography: EA/hex (1:9).Yield 49%, pale yellow solid, mp 196-198 ° C. IR (neat), 3029, 2866, 1602, 1515, 1490, 1477, 1398, 1089, 831 cm·1; W NMR (400 MHz, CDC13) δ 7.32 (d, J=8.8 Hz, 2H), 7.27 (d, J=8.8 Hz, 2H), 7.24 (d, J=8.0 Hz, 2 H), 7.22-7.19 (m, 3H), 7.(s, 1H), 7.13-7.11 (m, 2H), 7.08 (d, J=8.4 Hz, 2H), 6.96 (d, /=5.2 Hz, 1H), 6.92 (s, 1H) 6.91 (d, J=52 Hz, 1H); , 3C NM R (100 MHz, CDC13) δ 141.25, 140.53, 139.67, 138.12, 134.76, 134.17, 133.79, 133.75, 131.73, 130.71, 129.19, 128.80, 128.50, 127.77, 127.11, 126.18, 120.61, 115.85, 107.89, 107.78; El) m/z (relative intensity) 449 (M+4, 70), 447 (M+2, 25), 445 (M+, 100); HRMS (El) m/z calcd for C26H17C12NS 445.0459, found 445.0444. -{4-[2,2-Bis-(4-methoxy-phenyl)-vinyl]-phenyl}-5flr-thieno[2,3-c]pyrroIe (Id). Eluent for chromatography: EA/hex (l: 9).Yield 64, dark yellow solid, mp 178-179 °C. IR (neat), 3030, 2954, 2834, 1605, 1513, 1438, 1342, 1244, 1177, 1032, 834 cm'1; !H NMR (400 MHz, CDC13) δ 7.26 (d, ^8.8 Hz, 2H), 7.21 (d, J=2.4 Hz, 1 H), 7.20 (d, J=4.0 Hz, 2 H), 7.13 (d, J= 8.8 Hz, 2H), 7.09 (d, J=8.8 Hz, 3 H), 6.95 (d, J=5.6 Hz, 1H), 6.90 (d, J=5.6 Hz, 1H), 6.89 (s, 1H), 6.86 (d, J=5.2 Hz, 2H), 6.83 (d, J=6.4 Hz, 2H), 3.83 (s, 3H), 3.81(s, 3H); 13C NMR (100 MHz, CDC13) δ 159.40, 159.13 , 142.30, 139.02, 136.16, 136.09, 134.03, 132.51, - 131.57, 130.50, 128.85, 126.85, 125.98, 124.89, 120 .57, 115.89, 114.18, 113.64, 107.98, 107.88, 55.31, 55.22; MS (El) m/z (relative intensity) 437 (M+, 100); HRMS (El) m/z calcd for C28H23NO2S 437.1449, found 437.1452. 5-[4-(2,2-Di-/7-tolyl-vinyl)-phenyl]-4-methyl-5-flr-thieno[2^-c]pyrrole (le). Eluent for chromatography: EA/hex (1:9). Yield 47%, Orange solid, mp 160-162 °C. IR (neat), 3022, 2917, 2861, 1604, 1594, 1512, 1403, 1202, 825 cm'VHNMR (400 MHz, CDC13 δ 7.25 (d, J=8.0 Hz, 2H), 7.18 (d, J-8.0 Hz, 2H), 7.15-7.14 (m, 8H), 6.94 (s, 1H), 6.94 (s, 1H), 6.88 (s, 1H), 6.82 (s, 1H), 2.40 (s, 3H), 2.37 (s, 6H);, 3C NMR (100 MHz, CDC13) δ 143.42, 140.58, 138.36, 137.55, 137.31, 137.13, 136.84 , 131.83, 130.13, 129.99, 129.46, 128.93, 127.52, 125.80, 125.37, 124.89, 123.28, 117.61, 115.72, 109.12, 21.29, 21.11, 12.10; MS (El) m/z Page 25 of 58 pages 201000484 (relative Intensity) 420 (M+l, 100), 419 (10), 404 (2); HRMS (El) m/z calcd for C29H25NS 419.1708, found 419.1688. 5- [4-[2,2-Dipheny-vinyl] -phenyl] -4-ethyl-5^f-thieno [2,3-c] py Rrole (If). Eluent for chromatography: EA/hex (1:9). Yield 43%, yellow solid, mp 122-124 °C. IR (neat), 3020, 2932, 1601,1598, 1369, 1182, 916 Cm1; *11 NMR (400 MHz, CDC13) δ 7.40-7.32 (m, 8H), 7.38-7.35 (m, 2H), 7.12 (s, 2H), 7.03 (s, 1H), 6.97 (d, J= 5.6 Hz, 1H), 6.90 (d, J=5.2 Hz, 1H), 6.79 (s, 1H), 2.77 (q, J=7.6 Hz, 2H), 1.21 (t, J=7.6 Hz, 3H); 13C NMR (100 MHz, CDC13) δ. 143.53, 143.04, 139.98, 138.64, 136.72, 130.66, 130.23, 130.03, 128.76, 128.23, 127.71, 127.65, 127.56, 126.82, 125.77, 124.81, 124.04, 123.48, 116.10, 109.24, 19.32 , 14.03; MS (El) m/z (relative intensity) 405 (M+, 100), 391 (17), 390 (57); HRMS (El) m/z calcd for C28H23NS 405.1551, found 405.1555. 5-[4 -(2,2-Di-p-tolyl-vinyl)-phenyl]-4-ethyl-5^T-thieno[23-c]pyrrole (lg). Eluent for chromatography: EA/hex (1:9). Yield 48%, Orange solid, mp 154-156 °C. IR (neat), 3022, 2968, 2922 1604, 1511, 1404, 1110, 814 cm1; *H NMR (400 MHz, CDC13) δ 7.25 (d, J =8.0 Hz, 2H), 7.19- 7.09 (m, 10H), 6.92 (d, /=5.6 Hz, 1H), 6.89 (s, 1H) 6.88 (d, J=4.8 Hz, 1H), 6.78 (s, 1H), 2.77 (q, J=7.6 Hz, 2H), 2.41 (s, 3H), 2.37 (s, 3H) ; 3C NMR (100 MHz, CDC13) δ 143.48, 140.56, 138.44, 137.58, 137.32, 137.08, 130.62, 130.13, 129.96, 129.46, 128.94, 127.55, 125.80, 124.77, 124.12, 123.46, 116.15, 109.29, 21.32, 21.13 , 19.95, 14.06; MS (El) m/z (relative intensity) 434 (M+l, 100), 433 (4), 420 (17), 419 (56); HRMS (El) m/z calcd for C30H27NS 433.1864, found 433.1879. 5-[4-(2,2-Di-/)-tolyl-vinyl)-phenyI]-4-propyl-5H-thieno[2,3-c]pyrrole (lh). Eluent for chromatography Yield: EA/hex (1:9). Yield 32%, light yellow solid, mp 122-124 °C. IR (neat), 3077, 2958, 2927 2869, 1604, 1586, 1403, 1111, 813 cm'1; *H NMR (400 MHz, CDC13) δ 7.24 (d, J = 8.0 Hz, 2H), 7.16 (d, J = 8.4 Hz, 4H ), 7.12 (d, J = 9.2 Hz, 4H), 7.09 (d, J=8.8 Hz, 2H), 6.94 (s, 1H), 6.93 (d, J=5.6 Hz, 1 H), 6.88 (d, J-4.8 Hz, 1H), 6.78 (s, 1H), 2.70 (t , J=7.6 Hz, 2H), 2.40 (s, 3H) 2.37 (s, 3H), 1.56 (sex, J=7.2 Hz, 2H), 0.85 (t, /=7.2 Hz, 3H); 13C NMR (100 MHz, CDCI3) 143.52, 140.55, 138.48, 137.58, 137.31, 137.09, 131.15, 130.16, 129.93, 129.40, 128.93, 127.55, 125.87, 124.73, 123.34, 122.80, 116.21, 109.38, 28.47, 22.88, 21.29, 21.11, 13.96; MS (El) m/z (relative intensity) 448 (M+l, 78), 419 (100); HRMS (El) m/z Page 26 of 58 201000484 calcd for C31H29NS 447.2021, found 447.2043. 5-{4-[ 2,2-Bis-(4-chloro-phenyl)-vinyl]-phenyl}-4-propyl-5^-thieno[2,3-c]pyrrole (li).

Eluent for chromatography: EA/hex (1:9). Yield 38%, light yellow solid, mp 136-138 °C. IR (neat), 3033, 2958, 2930 2870, 1603, 1591, 1491, 1466, 1090, 1013, 832 cm'1; 'H NMR (400 MHz, CDC13) δ 7.33 (d, J=8.4 Hz, 2H), 7.30 (d, J=1.2 Hz, 2H ), 7.23 (d, J=8.4 Hz, 2H), 7.15 (d, J=7.6 Hz, 2H), 7.11 (d, J-10 Hz, 4H), 6.97 (s, 1H), 6.92 (d, J=52 Hz, 1H) , 6.88 (d, J=4.0Eluent for chromatography: EA/hex (1:9). Yield 38%, light yellow solid, mp 136-138 °C. IR (neat), 3033, 2958, 2930 2870, 1603, 1591, 1491, 1466, 1090, 1013, 832 cm'1; 'H NMR (400 MHz, CDC13) δ 7.33 (d, J=8.4 Hz, 2H), 7.30 (d, J=1.2 Hz, 2H), 7.23 (d, J=8.4 Hz, 2H), 7.15 (d, J=7.6 Hz, 2H), 7.11 (d, J-10 Hz, 4H), 6.97 (s, 1H), 6.92 (d, J=52 Hz, 1H), 6.88 (d, J=4.0

Hz, 1H), 6.78 (s, 1H), 2.70 (t, J=7.6 Hz, 2H), 1.56 (sex, J=7.2 Hz, 2H), 0.84 (t, J=6.8 Hz, 3H); 13C NMR (100 MHz, CDC13) δ 141.19, 140.79, 139.14, 138.00, 136.09, 133.87, 131.72, 131.35, 130.07, 129.54, 129.15, 128.86, 128.64, 128.53, 127.81, 126.06, 124.94, 123.55, 122.74, 116.19, 109.34, 28.50, 22.88, 13.98; MS (El) m/z (relative intensity) 489 (M+4, 10), 487 (M+2, 45)，458 (70)，235 (100); HRMS (El) w/z calcd for C29H23C12NS 487.0928, found 487.0917. 5-[4-(2,2-Diphenyl-vinyl)-phenyI]-4-phenyl-5-ir-thieno[2,3-c]pyrrole (lj) Eluent for chromatography: EA/hex (1:9). Yield 35%, yellow solid, mp 158-160 °C. FTIR (neat), 3061, 2986, 1607, 1592, 1513, 1491, 1401, 1341, 1090, 828 cm'1.'H NMR (400 MHz, CDC13) δ 7.31-7.25 (m, 9H), 7.24 (s, 2H), 7.22 (s, 1H), 7.19-7.14 (m, 5H), 7.05(d, J=5.2 Hz 1H), 7.01(d, J=5.6 Hz, 1H), 6.97(s, 3H), 6.93(s, 1H); 13C NMR(100 MHz CDC13) 5143.40, 143.08, 139.95, 138.82, 136.27, 133.25, 132.32, 130.26, 130.09, 128.66, 128.33,128.21, 127.67, - 127.58, 127.26, 126.92, 125.95, 125.48, 124.62, 122.08, 116.43, 112.26; MS (El) m/z (relative intensity) 453(M+, 100); HRMS calcd for C32H23NS 453.1551, found 453.1547 5-{4-[2,2-Bis-(4-chloro-phenyl)-vinyl】-phenyl}-4-phenyl-5/Mhieno[2,3，c】pyrrole (lk)· Eluent for chromatography: EA/hex (1:9).Yield 27%，yellow solid mp 168-170 °C. IR (neat), 3063, 2983, 1602, 1590, 1515, 1492, 1401, 1341, 1090, 828cm1; 'H NMR (400 MHz, CDCI3) δ 7.26-7.15 (m, 12H), 7.08(d, J=8.4 Hz, 4H), 7.04 (d, J=5.2 Hz, 1H), 7.02 (d, /=5.2 Hz，1H), 6.98 (d, «7=4.8 Hz, 2H), 6.91(s，lH); 13C NMR (100 MHz, CDC13): δ 141.16, 141.05, 139.23, 137.95, 135.63, 133.78, 133.40, 132.28,131.72, 130.12, 129.06, 128.85, 128.50, 128.41, 127.87, 127.41, 126.07, 125.64, 124.80, 122.16, 116.41, 112.14; MS (El) m/z (relative intensity) 525(M+4, 80), 523(M+2, 48), 521(^, 100). HRMS calcd for C32H21CI2NS 521.0772, found 521.0776. 第27頁/共58頁 201000484Hz, 1H), 6.78 (s, 1H), 2.70 (t, J=7.6 Hz, 2H), 1.56 (sex, J=7.2 Hz, 2H), 0.84 (t, J=6.8 Hz, 3H); 13C NMR (100 MHz, CDC13) δ 141.19, 140.79, 139.14, 138.00, 136.09, 133.87, 131.72, 131.35, 130.07, 129.54, 129.15, 128.86, 128.64, 128.53, 127.81, 126.06, 124.94, 123.55, 122.74, 116.19, 109.34, 28.50 , 22.88, 13.98; MS (El) m/z (relative intensity) 489 (M+4, 10), 487 (M+2, 45), 458 (70), 235 (100); HRMS (El) w/ z calcd for C29H23C12NS 487.0928, found 487.0917. 5-[4-(2,2-Diphenyl-vinyl)-phenyI]-4-phenyl-5-ir-thieno[2,3-c]pyrrole (lj) Eluent for chromatography : EA/hex (1:9). Yield 35%, yellow solid, mp 158-160 °C. FTIR (neat), 3061, 2986, 1607, 1592, 1513, 1491, 1401, 1341, 1090, 828 cm' 1. 'H NMR (400 MHz, CDC13) δ 7.31-7.25 (m, 9H), 7.24 (s, 2H), 7.22 (s, 1H), 7.19-7.14 (m, 5H), 7.05 (d, J= 5.2 Hz 1H), 7.01 (d, J = 5.6 Hz, 1H), 6.97 (s, 3H), 6.93 (s, 1H); 13C NMR (100 MHz CDC13) 5143.40, 143.08, 139.95, 138.82, 136.27, 133.25, 132.32, 130.26, 130.09, 128.66, 128.33, 128.21, 127.67, - 127.58, 127.2 6, 126.92, 125.95, 125.48, 124.62, 122.08, 116.43, 112.26; MS (El) m/z (relative intensity) 453 (M+, 100); HRMS calcd for C32H23NS 453.1551, found 453.1547 5-{4-[2, 2-Bis-(4-chloro-phenyl)-vinyl]-phenyl}-4-phenyl-5/Mhieno[2,3,c]pyrrole (lk)· Eluent for chromatography: EA/hex (1:9). Yield 27%, yellow solid mp 168-170 ° C. IR (neat), 3063, 2983, 1602, 1590, 1515, 1492, 1401, 1341, 1090, 828 cm1; 'H NMR (400 MHz, CDCI3) δ 7.26- 7.15 (m, 12H), 7.08 (d, J=8.4 Hz, 4H), 7.04 (d, J=5.2 Hz, 1H), 7.02 (d, /=5.2 Hz, 1H), 6.98 (d, «7= 4.8 Hz, 2H), 6.91 (s, lH); 13C NMR (100 MHz, CDC13): δ 141.16, 141.05, 139.23, 137.95, 135.63, 133.78, 133.40, 132.28, 131.72, 130.12, 129.06, 128.85, 128.50, 128.41 , 127.87, 127.41, 126.07, 125.64, 124.80, 122.16, 116.41, 112.14; MS (El) m/z (relative intensity) 525 (M+4, 80), 523 (M+2, 48), 521 (^, 100). HRMS calcd for C32H21CI2NS 521.0772, found 521.0776. Page 27 of 58 201000484

Example 3Example 3

5-{4-[2,2-Bis-(3-trifluoromethyl_phenyl)-vinyll-phenyl}-5/Mhieno【2,3-c】pyrrole (2).5-{4-[2,2-Bis-(3-trifluoromethyl_phenyl)-vinyll-phenyl}-5/Mhieno [2,3-c]pyrrole (2).

Eluent for chromatography: EA/hex (l:9).Yield 47%, pale yellow solid, mp 114-116 °C. IR (neat)，3039, 2954, 2924, 2854, 1605, 1517, 1465, 1447, 1400, 1303, 1167, 1127, 801 cm.1; 'H NMR (400 MHz, CDC13) δ 7.64 (t, 2H), 7.57 (d, J=7.6 Hz, 1H), 7.51-7.38 (m, 5H), 7.25 (d, J=8.4 Hz, 2H), 7.22 (d, J=2.0 Hz, 1H), 7.12 (d J=0.8 Hz, 1H), 7.06 (d, 7=8.8 Hz, 2H), 7.05 (s, 1H), 6.97 (d, J=5.2 Hz, 1H), 6.90(d, J=5.6 Hz, 1H); 3C NMR (100 MHz) δ 145.57, 143.27, 140.17, 140.08, 134.25, 134.17, 133.83, 130.91, 130.79, 129.66, 129.52, 128.94, 127.21, 127.16, 126.29, 124.85, 124.09, 124.05,120.66, 115.84, 107.90, 107.79; MS (El) m/z (relative intensity) 514 (M+l, 100)，513 (M+, 7); HRMS (El) m/z calcd for C28H17F6NS 513.0986, found 513.0984.Eluent for chromatography: EA/hex (l:9).Yield 47%, pale yellow solid, mp 114-116 °C. IR (neat), 3039, 2954, 2924, 2854, 1605, 1517, 1465, 1447, 1400 , 1303, 1167, 1127, 801 cm.1; 'H NMR (400 MHz, CDC13) δ 7.64 (t, 2H), 7.57 (d, J=7.6 Hz, 1H), 7.51-7.38 (m, 5H), 7.25 (d, J=8.4 Hz, 2H), 7.22 (d, J=2.0 Hz, 1H), 7.12 (d J=0.8 Hz, 1H), 7.06 (d, 7=8.8 Hz, 2H), 7.05 (s , 1H), 6.97 (d, J = 5.2 Hz, 1H), 6.90 (d, J = 5.6 Hz, 1H); 3C NMR (100 MHz) δ 145.57, 143.27, 140.17, 140.08, 134.25, 134.17, 133.83, 130.91 , 130.79, 129.66, 129.52, 128.94, 127.21, 127.16, 126.29, 124.85, 124.09, 124.05, 120.66, 115.84, 107.90, 107.79; MS (El) m/z (relative intensity) 514 (M+l, 100), 513 (M+, 7); HRMS (El) m/z calcd for C28H17F6NS 513.0986, found 513.0984.

Example 4Example 4

3bR6 = -CH3 5-(4-Fluoren-9-ylidenemethyl-phenyl)-5ii-thieno[2,3-c]pyrroIe (3a). Eluent for chromatography: CHiC^/hex (2:8). Yield 60%, bright yellow solid, mp 229-230 °C. IR (neat), 3060, 2954, 1591, 1513, 1448, 1436, 1342, 1104, 1013, 860 cm'1; NMR (400 MHz, CDCI3/DMSO) δ 7.38 (d, J=7.2 Hz, 1H), 7.73 (d, J=7.2 Hz, 2H), 7.69 (d, J=8.4 Hz, 2H), 7.66 第28頁/共58頁 201000484 (d, J=6.4Hz, 2H), 7.54 (d, J=8.4 Hz, 2H), 7.41-7.32 (m, 3H), 7.26 (d, J=12 Hz, 2H), 7.10 (t, J=7.6 Hz, 1H), 7.02 (d, J=5.2 Hz, 1H), 6.99 (d, J=5.2 Hz, 1H); 13C NMR (100 MHz, CDCI3/DMSO) 5140.42, 138.70, 138.49, 138.19, 135.40, 133.74, 133.53, 130.04, 129.92, 128.04, 127.64, 126.45, 126.36, 126.05, 125.99, 125.43, 124.02, 123.44, 120.02, 119.86, 119.56, 119.08, 118.83, 115.24, 109.21, 107.21, , 107.14; MS (El) m/z (relative intensity) ' 375 (M+, 100); HRMS (El) m/z calcd for C26Hi7NS 375.1082, found 375.1069. 5-(4-FIuoren-9-ylidenemethyl-phenyl)-4-methyl-5//-thieno[2,3c]pyrrole (3b). Eluent for chromatography: EA/hex (1:9).Yield 49%? yellow solid, mp 148- 150 °C. IR (neat), 3060, 1590, 1515, 1448, 1437, 1342, 1104, 1012, 860 cm'1; 'H NMR (400 MHz, CDC13) 8 7.87 (d, J=7.6 Hz, 1H), 7.72 (d, /=8.0 Hz 2H), 7.66 (t, J=7.6 Hz, 4H), 7.41 (d, J=8.4 Hz, 2H), 7.34 (t, J=7.2 Hz, 3H), 7.11 (t, J=7.6 Hz, 1H), 6.96 (s, 1H), 6.93 (s, 2H), 2.4 (s, 3H); 13C NMR (100 MHz, CDC13) δ 146.42, 141.40, 139.86, 139.30, 139.19, 137.07, 136.26, 135.86, 132.15, 130.13, 128.79, 128.40, 127.04, 126.70, 125.89, 125.79, 125.75, 125.21, 124.22, 123.66, 120.25, 119.85, 119.61, 117.63, 115.74, 109.22, 12.25; MS (El) m/z (relative intensity) 389 (M+, 100), 389 (19) ;HRMS (El) m/z calcd for C27H19NS 389.1238, found 389.1253.3bR6 = -CH3 5-(4-Fluoren-9-ylidenemethyl-phenyl)-5ii-thieno[2,3-c]pyrroIe (3a). Eluent for chromatography: CHiC^/hex (2:8). Yield 60% , bright yellow solid, mp 229-230 °C. IR (neat), 3060, 2954, 1591, 1513, 1448, 1436, 1342, 1104, 1013, 860 cm'1; NMR (400 MHz, CDCI3/DMSO) δ 7.38 (d, J=7.2 Hz, 1H), 7.73 (d, J=7.2 Hz, 2H), 7.69 (d, J=8.4 Hz, 2H), 7.66 Page 28 of 58 201000484 (d, J= 6.4 Hz, 2H), 7.54 (d, J=8.4 Hz, 2H), 7.41-7.32 (m, 3H), 7.26 (d, J=12 Hz, 2H), 7.10 (t, J=7.6 Hz, 1H) , 7.02 (d, J=5.2 Hz, 1H), 6.99 (d, J=5.2 Hz, 1H); 13C NMR (100 MHz, CDCI3/DMSO) 5140.42, 138.70, 138.49, 138.19, 135.40, 133.74, 133.53, 130.04 , 129.92, 128.04, 127.64, 126.45, 126.36, 126.05, 125.99, 125.43, 124.02, 123.44, 120.02, 119.86, 119.56, 119.08, 118.83, 115.24, 109.21, 107.21, , 107.14; MS (El) m/z (relative intensity ) '375 (M+, 100); HRMS (El) m/z calcd for C26Hi7NS 375.1082, found 375.1069. 5-(4-FIuoren-9-ylidenemethyl-phenyl)-4-methyl-5//-thieno[2, 3c]pyrrole (3b). Eluent for chromatography: EA /hex (1:9).Yield 49%? yellow solid, mp 148- 150 °C. IR (neat), 3060, 1590, 1515, 1448, 1437, 1342, 1104, 1012, 860 cm'1; 'H NMR (400 MHz, CDC13) 8 7.87 (d, J=7.6 Hz, 1H), 7.72 (d, /=8.0 Hz 2H), 7.66 (t, J=7.6 Hz, 4H), 7.41 (d, J=8.4 Hz, 2H), 7.34 (t, J=7.2 Hz, 3H), 7.11 (t, J=7.6 Hz, 1H), 6.96 (s, 1H), 6.93 (s, 2H), 2.4 (s, 3H); 13C NMR (100 MHz, CDC13) δ 146.42, 141.40, 139.86, 139.30, 139.19, 137.07, 136.26, 135.86, 132.15, 130.13, 128.79, 128.40, 127.04, 126.70, 125.89, 125.79, 125.75, 125.21, 124.22, 123.66, 120.25 , 119.85, 119.61, 117.63, 115.74, 109.22, 12.25; MS (El) m/z (relative intensity) 389 (M+, 100), 389 (19) ; HRMS (El) m/z calcd for C27H19NS 389.1238, found 389.1253 .

Example §Example §

4a R38 = H 4b R38 = CH3 5-NaphthaIen-l-yl-5//-thieno[2,3"C]pyrroie (4a). This compound was prepared using the same procedure as that for the synthesis of compound 20. Eluent for chromatography: CH2Cl2/hex (2:8)). Yield 44%, light yellow solid, mp 90-92 °C. IR (neat), 3130, 3050, 1595, 1572, 1508, 1498, 1466, 1413, 1110, 802 cm'1; 'H NMR (400Hz, CDC13) 6 7.96-792 (m, 2H), 7.77 (d, J=8.4 Hz, 1H), 7.58-7.47 (m, 4H), 7.24 (s, 1H), 7.12 (s, 1H), 7.07 (d, J=5.2 Hz, 第29頁/共58頁 201000484 1H)，7.04 (d, *7=5.2 Hz，H); 13C NMR (1 ⑻MHz) δ 138.26, 134.06, 133.05, 129.83, 128.31， 127.99, 127.11, 126.60, 126.42, 125.00, 124.79, 123.75, 123.11，115.85, 112.05, 111.99; MS (El) m/z (relative intensity) 249 (M+, 100); HRMS (El) m/z calcd for CieHnNS 249.0612, found 249.0604. 5-(4-Methyl-naphthalen-l-yl)-5H-thieno[2,3-c]pyrrole (4b). Eluent for * chromatography: EA/hex (2:8). Yield 46%, light yellow solid, mp 150-152 °C. IR (neat), 3129, 3071, 2937, 1596, 1570, 1498, 1466, 1406, 1153, 817 cm'1; Ή NMR (400 MHz, CDC13) δ 8.07 (d，·7=8·4 Hz，1H), 7.70 (d, ·7=8·4 Hz，1H), 7.60-7.56 (m, 1H), 7.49-7.46 (m，1H), 7.42 (d, J=12 Hz, 1 H), 7.36(d, J=7.2 Hz, 1 H), 7.19 (s, 1H), 7.08 (s, 1H), 7.05 (d, J=5.6 Hz, 1H), 7.02 (d, J=5.2 Hz, 1H)，2.76 (s, 3H); 13C NMR(100 MHz, CDC13) δ 136.79, 135.06, 132.90, 129.99, 126.76, 126.47, 126.28, 125.70, 124.56, 124.33, 123.67, 123.52, 115.90, 112.28, 112.21, 19.43; MS m/z (relative intensity) 263 (M+, 100) 262 (47), 248 (44); HRMS (El) m/z calcd for C17H13CNS 263.0769, found 263.0742. The structure of this compound was confirmed by X-ray analysis.4a R38 = H 4b R38 = CH3 5-NaphthaIen-l-yl-5//-thieno[2,3"C]pyrroie (4a). This compound was prepared using the same procedure as that for the synthesis of compound 20. Eluent for chromatography: CH2Cl2/hex (2:8)). Yield 44%, light yellow solid, mp 90-92 °C. IR (neat), 3130, 3050, 1595, 1572, 1508, 1498, 1466, 1413, 1110, 802 cm'1; 'H NMR (400Hz, CDC13) 6 7.96-792 (m, 2H), 7.77 (d, J=8.4 Hz, 1H), 7.58-7.47 (m, 4H), 7.24 (s, 1H), 7.12 (s, 1H), 7.07 (d, J=5.2 Hz, page 29 of 58 pages 201000484 1H), 7.04 (d, *7=5.2 Hz, H); 13C NMR (1 (8) MHz) δ 138.26, 134.06, 133.05, 129.83, 128.31, 127.99, 127.11, 126.60, 126.42, 125.00, 124.79, 123.75, 123.11, 115.85, 112.05, 111.99; MS (El) m/z (relative intensity) 249 (M+, 100); HRMS (El) m/z calcd for CieHnNS 249.0612, found 249.0604. 5-(4-Methyl-naphthalen-l-yl)-5H-thieno[2,3-c]pyrrole (4b). Eluent for * chromatography: EA /hex (2:8). Yield 46%, light yellow solid, mp 150-152 °C. IR (neat), 3129, 3071, 2937, 1596, 1570, 1498, 1466, 1406, 1153 , 817 cm'1; Ή NMR (400 MHz, CDC13) δ 8.07 (d, ·7=8·4 Hz,1H), 7.70 (d, ·7=8·4 Hz,1H), 7.60-7.56 (m , 1H), 7.49-7.46 (m,1H), 7.42 (d, J=12 Hz, 1 H), 7.36 (d, J=7.2 Hz, 1 H), 7.19 (s, 1H), 7.08 (s, 1H), 7.05 (d, J=5.6 Hz, 1H), 7.02 (d, J=5.2 Hz, 1H), 2.76 (s, 3H); 13C NMR (100 MHz, CDC13) δ 136.79, 135.06, 132.90, 129.99 , 126.76, 126.47, 126.28, 125.70, 124.56, 124.33, 123.67, 123.52, 115.90, 112.28, 112.21, 19.43; MS m/z (relative intensity) 263 (M+, 100) 262 (47), 248 (44); HRMS (El) m/z calcd for C17H13CNS 263.0769, found 263.0742. The structure of this compound was confirmed by X-ray analysis.

5 S-Thienop^-clpyrrol-S-yl-lJ^-indazole (5). Eluent for chromatography: CHiCb/hex (2:8). Yield 52%, light brown solid, mp: 242-244 °C. IR (neat) 3443 (NH), 1644, 1506, 1347, 1153, 880 cm'1; 'H NMR (400Hz, CDC13): δ 12.31 (br, s, NH), 7.20 (s, 1H), 7.01 (s, 1H), 6.71-6.70 (m, 2H), 6.62 (d, >=2.0 Hz, 1H), 6.58 (d, J=\.6 Hz, 1H), 6.20 (d, J=52 Hz 1H), 6.04 (d, J=5.6 Hz, H); ,3C NMR (100 MHz) δ 138.44, 134.27, 133.93, 133.45, 126.80, 124.83, 123.08, 116.19, 111.99, 111.29, 108.94, 108.91; MS (El) m/z (relative intensity) 398 (M+, 100), 238 (25); HRMS (El) m/z calcd for C,3H9N3S 239.0517, found 239.0510.5 S-Thienop^-clpyrrol-S-yl-lJ^-indazole (5). Eluent for chromatography: CHiCb/hex (2:8). Yield 52%, light brown solid, mp: 242-244 °C. IR (neat) 3443 (NH), 1644, 1506, 1347, 1153, 880 cm'1; 'H NMR (400Hz, CDC13): δ 12.31 (br, s, NH), 7.20 (s, 1H), 7.01 (s , 1H), 6.71-6.70 (m, 2H), 6.62 (d, >=2.0 Hz, 1H), 6.58 (d, J=\.6 Hz, 1H), 6.20 (d, J=52 Hz 1H) , 6.04 (d, J = 5.6 Hz, H); , 3C NMR (100 MHz) δ 138.44, 134.27, 133.93, 133.45, 126.80, 124.83, 123.08, 116.19, 111.99, 111.29, 108.94, 108.91; MS (El) m /z (relative intensity) 398 (M+, 100), 238 (25); HRMS (El) m/z calcd for C, 3H9N3S 239.0517, found 239.0510.

Example 7 第30頁/共58頁 201000484 N- 〇CH3Example 7 Page 30 of 58 201000484 N- 〇CH3

H3CO 2-(2,4-dimethoxyphenyl)-2H-benzo[4,5]thieno[2,3-c]pyrrole. IR (CHCI3) : vl591， 1517, 1442, 1208, 1027, 749 cm'1 ； NMR (400 MHz, CDC13) ： 87.77 (d, J= 6.8 Hz, 1 H), 7.64 (d, J= 7.6 Hz, 1 H), 7.37 (d，·/= 1.6 Hz，1 H)，7.27〜7_22 (m, 3 H), 6.96 (d，J= 1.2 Hz, 1 H), 6.59 (d, J= 2.8 Hz, 1 H), 6.52 (dd, 8.8 Hz, J= 2.8 Hz, 1 H), 3.84 (s, 3 H), 3.80 (s, 3 H) ； 13C NMR (100 MHz, CDC13) ： 5159.8 (C), 154.1(C), 143.6 (C), 131.5 (C), 128.5 (C), 127.2 (CH), 124.5 (CH), 124 (CH), 123.3 (CH), 122.0 (C), 121.3 (CH), 112.8 (CH), 112 (CH), 104.3 (CH), 99.8 (CH), 55.8 (CH3), 55.6 (CH3) ； MS(EI) mh 309(M+,100), 308(17), 294(24), 266(6) ； HRMS(EI) m/z calcd for C,gHi5N〇2S ： 309.0823 ； found ： 309.0821.H3CO 2-(2,4-dimethoxyphenyl)-2H-benzo[4,5]thieno[2,3-c]pyrrole. IR (CHCI3) : vl591, 1517, 1442, 1208, 1027, 749 cm'1 ; NMR (400 MHz, CDC13): 87.77 (d, J= 6.8 Hz, 1 H), 7.64 (d, J= 7.6 Hz, 1 H), 7.37 (d,··= 1.6 Hz, 1 H), 7.27~7_22 (m, 3 H), 6.96 (d, J = 1.2 Hz, 1 H), 6.59 (d, J = 2.8 Hz, 1 H), 6.52 (dd, 8.8 Hz, J = 2.8 Hz, 1 H), 3.84 (s, 3 H), 3.80 (s, 3 H) ; 13C NMR (100 MHz, CDC13): 5159.8 (C), 154.1 (C), 143.6 (C), 131.5 (C), 128.5 (C), 127.2 (CH), 124.5 (CH), 124 (CH), 123.3 (CH), 122.0 (C), 121.3 (CH), 112.8 (CH), 112 (CH), 104.3 (CH), 99.8 (CH), 55.8 (CH3), 55.6 (CH3); MS(EI) mh 309(M+,100), 308(17), 294(24), 266(6) ; HRMS(EI) m/z calcd for C,gHi5N〇2S : 309.0823 ; found : 309.0821.

Example 8 OCH, N-Example 8 OCH, N-

H3CO 2-(2,5-dimethoxyphenyI)-2H-benzo [4,5] thieno [2,3-c] pyrrole. Yield 70%, mp: 164-165 "C. IR (CHC13) ： v2937, 1610, 1533, 1460, 1204, 773 cm'1 ； ή NMR (400 MHz, CDCI3) ： 57.78 (d, J= 7.6 Hz, 1 H), 7.64 (d, J= 7.6 Hz, 1 H), 7.47 (d, J- 2.0 Hz, 1 H), 7.29 -7.23 (m, 2 H), 7.07 (d, J= 2.0 Hz, 1 H), 6.98 (d, J- 8.8 Hz, 1 H), 6.95 (d, 3.2 Hz, 1 H), 6.84 (dd, J = 9 Hz, J = 3.2 Hz, 1 H), 3.80 (s, 3 H), 3.78 (s, 3 H) ； 13C NMR (100 MHz, CDCI3) ： 5153.9 (C), 146.9(C), 143.7 (C), 131.4 (C), 131.0 (C), 129.0 (C), 124.8 (CH), 124.1 (CH), 123.3 (CH), 122.6 (C), 121.4 (CH), 114.1 (CH),112.6 (CH), 112.4 (CH), 112.4 (CH), 111.6 (CH), 56.7 (CH3), 55.9(CH3) ； MS(EI) mlz 309(M+,100), 308(24), 294(18), 280(9), 279(15), 223(8), 197(10), 147(9) ； HRMS(EI) m/z calcd for C18Hi5N02S ： 309.0823 ； found ： 309.0820.H3CO 2-(2,5-dimethoxyphenyI)-2H-benzo [4,5] thieno [2,3-c] pyrrole. Yield 70%, mp: 164-165 "C. IR (CHC13) : v2937, 1610 , 1533, 1460, 1204, 773 cm'1 ; NMR NMR (400 MHz, CDCI3): 57.78 (d, J = 7.6 Hz, 1 H), 7.64 (d, J = 7.6 Hz, 1 H), 7.47 (d , J- 2.0 Hz, 1 H), 7.29 -7.23 (m, 2 H), 7.07 (d, J= 2.0 Hz, 1 H), 6.98 (d, J- 8.8 Hz, 1 H), 6.95 (d, 3.2 Hz, 1 H), 6.84 (dd, J = 9 Hz, J = 3.2 Hz, 1 H), 3.80 (s, 3 H), 3.78 (s, 3 H) ; 13C NMR (100 MHz, CDCI3): 5153.9 (C), 146.9(C), 143.7 (C), 131.4 (C), 131.0 (C), 129.0 (C), 124.8 (CH), 124.1 (CH), 123.3 (CH), 122.6 (C), 121.4 (CH), 114.1 (CH), 112.6 (CH), 112.4 (CH), 112.4 (CH), 111.6 (CH), 56.7 (CH3), 55.9 (CH3); MS(EI) mlz 309 (M+,100 ), 308(24), 294(18), 280(9), 279(15), 223(8), 197(10), 147(9); HRMS(EI) m/z calcd for C18Hi5N02S : 309.0823 ; Found : 309.0820.

Example 9 第31頁/共58頁 201000484Example 9 Page 31 of 58 201000484

N-N-

Yield 'HNMR 2-(2,3-dihydro-l,4-benzodioxin-6-yl)-2H-benzo[4,5]thieno[2,3-c]pyrrole. 68%，mp: 142-143 °C.IR (CHC13) : v2984, 1603, 1511，1246, 1065, 890, 746 cm_1 (400 MHz, CDCb) ： 67.77 (d,J= 7.6 Hz, 1 H), 7.65 (d, J= 7.6 Hz, 1 H), 7.44 (d, 2.0 Hz, 1 H)，7.29〜7.23 (m，2 H)，7.05 (d，J= 1.6 Hz，1 H), 6_99 (d, ·/= 1.2 Hz，1 H), 6.93 (d，·/ = 2 Hz, 2 H), 4.27 (s, 4 H), ； 13C NMR (100 MHz, CDC13) ： 5144.0 (C), 143.6(C), 142.2 (C), 135.1 (C), 131.2 (C),129.6 (C), 124.8 (CH), 124.2 (CH), 123.4 (CH), 121.3 (C), 117.9 (CH), 114.3 (CH), 110.6 (CH), 109.9 (CH), 109.3 (CH), 64.4 (CH2), 64.2(CH2), ； MS(EI) m/z 307(M+,100), 306(6)，251(23), 223(10)，195(4), 146(1)，； HRMS(EI) w/z calcd for C18H13N02S : 307.0667 ; found · 307.0663.Yield 'HNMR 2-(2,3-dihydro-l,4-benzodioxin-6-yl)-2H-benzo[4,5]thieno[2,3-c]pyrrole. 68%, mp: 142-143 ° C.IR (CHC13): v2984, 1603, 1511, 1246, 1065, 890, 746 cm_1 (400 MHz, CDCb): 67.77 (d, J = 7.6 Hz, 1 H), 7.65 (d, J = 7.6 Hz, 1 H), 7.44 (d, 2.0 Hz, 1 H), 7.29~7.23 (m, 2 H), 7.05 (d, J = 1.6 Hz, 1 H), 6_99 (d, ·/= 1.2 Hz, 1 H ), 6.93 (d,·· = 2 Hz, 2 H), 4.27 (s, 4 H), ; 13C NMR (100 MHz, CDC13): 5144.0 (C), 143.6(C), 142.2 (C), 135.1 (C), 131.2 (C), 129.6 (C), 124.8 (CH), 124.2 (CH), 123.4 (CH), 121.3 (C), 117.9 (CH), 114.3 (CH), 110.6 (CH), 109.9 (CH), 109.3 (CH), 64.4 (CH2), 64.2 (CH2), ; MS(EI) m/z 307(M+,100), 306(6),251(23), 223(10),195 (4), 146(1),; HRMS(EI) w/z calcd for C18H13N02S : 307.0667 ; found · 307.0663.

Example 10Example 10

NN

2-(4-isopropyIphenyl)-2H-benzo[4,5]thieno[2,3-c]pyrrole. Yield 79%, mp: 77-78〇C.IR (CHC13) ： v2914, 1553, 1503, 1464, 1286, 743 cm'1 ； lH NMR (400 MHz, CDC13) ： 57.79 (d, J= 6.8 Hz, 1 H), 7.65 (d, J= 7.2 Hz, 1 H), 7.52 (d, J= 1.6 Hz, 1 H), 7.40 (s, 1 H)，7.38 (d, J二 2·4 Hz，1 H)，7.32〜7.23 (m, 4 H), 7.13 (s, 1 H)，2.99-2.92 (m，1 H), 1.29 (s, 3 H), 1.28(s, 3 H) ； l3C NMR (100 MHz, CDC13) ： 6147.2 (C), 143.7(C), 138.9 (C), 131.2 (C) ,129.8 (C), 127.6 (CH), 124.8 (CH), 124.2 (CH), 123.4 (CH), 121.4 (CH), 121.2 (CH), 109.8 (CH), 109.2 (CH), 33.6 (CH), 24(CH3) ； MS(EI) m/z 291(1^,100), 276(32), 275(8), 249(10),248(18), 172(6), 146(12), 138(10) ； HRMS(EI) m/z calcd for C,9Hi7NS ： 291.1081 ； found ： 291.1083.2-(4-isopropyIphenyl)-2H-benzo[4,5]thieno[2,3-c]pyrrole. Yield 79%, mp: 77-78〇C.IR (CHC13) : v2914, 1553, 1503, 1464 , 1286, 743 cm'1 ; lH NMR (400 MHz, CDC13): 57.79 (d, J = 6.8 Hz, 1 H), 7.65 (d, J = 7.2 Hz, 1 H), 7.52 (d, J = 1.6 Hz, 1 H), 7.40 (s, 1 H), 7.38 (d, J 2·4 Hz, 1 H), 7.32~7.23 (m, 4 H), 7.13 (s, 1 H), 2.99-2.92 (m,1 H), 1.29 (s, 3 H), 1.28(s, 3 H) ; l3C NMR (100 MHz, CDC13) : 6147.2 (C), 143.7(C), 138.9 (C), 131.2 (C ), 129.8 (C), 127.6 (CH), 124.8 (CH), 124.2 (CH), 123.4 (CH), 121.4 (CH), 121.2 (CH), 109.8 (CH), 109.2 (CH), 33.6 (CH) ), 24(CH3) ; MS(EI) m/z 291(1^,100), 276(32), 275(8), 249(10),248(18), 172(6), 146(12 ), 138(10) ; HRMS(EI) m/z calcd for C,9Hi7NS : 291.1081 ; found : 291.1083.

Example 11Example 11

NN

2-(2,3-dimethylphenyl)-2H-benzo[4,5]thieno[2,3-c]pyrrole. Yield 76%, mp: 114-115 第32頁/共58頁 201000484 °C.IR (CHC13) ： v2933,1608,1559,1511, 1268, 807, 746 cm'1 ； !H NMR (400 MHz, CDC13)： 67.78 (dd, J= 7.6 Hz, J= 1.6 Hz, 1 H), 7.64 (dd, J= 7.6 Hz, J= 1.6 Hz, 1 H), 7.51 (d, J= 2.0 Hz, 1 H), 7.28-7.19 (m, 5 H), 7.12 (d, J= 2.4 Hz, 1 H), 2.32 (s, 3 H), 2.29 (s, 3 H) ； 13C NMR (100 MHz, CDC13) ： 8143.7 (C), 139(C), 138.1 (C), 134.8 (C), 131.3 (C),130.6 (CH), 129.7 (C), 124.8 (CH), 124.2 (CH), 123.4 (CH), 122.5 (CH), 121.3 (CH), 118.5 (CH), 109.8 (CH), 109.2 (CH), 19.9 (CH3), 19.2(CH3) ； MS(EI) m/z 277(M+,100), 276(6), 262(23), 235(8), 146(10)，； HRMS(EI)w/z calcd for C18H15NS : 277.0925 ; found : 277.0926·2-(2,3-dimethylphenyl)-2H-benzo[4,5]thieno[2,3-c]pyrrole. Yield 76%, mp: 114-115 Page 32 of 58 201000484 °C.IR ( CHC13) : v2933,1608,1559,1511, 1268, 807, 746 cm'1 ; !H NMR (400 MHz, CDC13): 67.78 (dd, J= 7.6 Hz, J=1.6 Hz, 1 H), 7.64 ( Dd, J= 7.6 Hz, J= 1.6 Hz, 1 H), 7.51 (d, J= 2.0 Hz, 1 H), 7.28-7.19 (m, 5 H), 7.12 (d, J= 2.4 Hz, 1 H ), 2.32 (s, 3 H), 2.29 (s, 3 H) ; 13C NMR (100 MHz, CDC13): 8143.7 (C), 139(C), 138.1 (C), 134.8 (C), 131.3 (C ), 130.6 (CH), 129.7 (C), 124.8 (CH), 124.2 (CH), 123.4 (CH), 122.5 (CH), 121.3 (CH), 118.5 (CH), 109.8 (CH), 109.2 (CH) ), 19.9 (CH3), 19.2 (CH3); MS(EI) m/z 277(M+,100), 276(6), 262(23), 235(8), 146(10),; HRMS(EI ) w/z calcd for C18H15NS : 277.0925 ; found : 277.0926·

Example 12 〇CH3Example 12 〇CH3

OCH, 2-(3,4,5-trimethoxyphenyl)-2H-benzo[4,5]thieno[23-c]pyrrole. Yield 85%, mp: 130-131 °C.IR (CHCb) ： v2941, 1596, 1508, 1231, 1127, 749 cm'1 ； 'H NMR (400 MHz, CDC13) ： 57.78 (dd, J= 7.6 Hz, J= 1.6 Hz 1 H), 7.65 (d, J= 7.6 Hz, 1 H), 7.48 (d, J = 2 Hz, 1 H)，7.31 〜7.23 (m，2 H)，7.10 (d, J = 2 Hz, 1 H), 6.68 (s, 2 H)，3.91 (s, 6 H)，3.87 (s, 3 H): 13CNMR(100 MHz, CDC13)： 5153.8 (C), 143.6(C), 137.2 (C), 136.6 (C), 131.0(C), 129.8 (C), 124.9 (CH), 124.2 (CH), 123.7 (C), 123.4 (CH),121.3 (CH), 110.1 (CH), 109.5 (CH), 99.3 (CH), 61.0 (CH3), 56.2(CH3) ； MS(EI) mlz 339(M+,100), 324(34), 308(7), 266(5), 210(6), 169(6) ； HRMS(E1) m/z caicd for C19H1NO3S ： 339.0929 ； found ： 339.0924.OCH, 2-(3,4,5-trimethoxyphenyl)-2H-benzo[4,5]thieno[23-c]pyrrole. Yield 85%, mp: 130-131 °C.IR (CHCb) : v2941, 1596 , 1508, 1231, 1127, 749 cm'1 ; 'H NMR (400 MHz, CDC13): 57.78 (dd, J= 7.6 Hz, J=1.6 Hz 1 H), 7.65 (d, J= 7.6 Hz, 1 H ), 7.48 (d, J = 2 Hz, 1 H), 7.31 to 7.23 (m, 2 H), 7.10 (d, J = 2 Hz, 1 H), 6.68 (s, 2 H), 3.91 (s, 6 H), 3.87 (s, 3 H): 13CNMR (100 MHz, CDC13): 5153.8 (C), 143.6 (C), 137.2 (C), 136.6 (C), 131.0 (C), 129.8 (C), 124.9 (CH), 124.2 (CH), 123.7 (C), 123.4 (CH), 121.3 (CH), 110.1 (CH), 109.5 (CH), 99.3 (CH), 61.0 (CH3), 56.2 (CH3); MS (EI) mlz 339 (M+, 100), 324 (34), 308 (7), 266 (5), 210 (6), 169 (6); HRMS (E1) m/z caicd for C19H1NO3S: 339.0929; Found : 339.0924.

Example 13 _ T^\Example 13 _ T^\

NN

^—〇CH3 OCH3 2-(3,4-dimethoxyphenyl)-2H-benzo[4,5】thieno【2,3-c】pyrrole· Yield 84%，mp: 119-120 °C. IR (CHC13) ： v2839, 1598, 1537, 1268, 1170, 726 cm'1 ； *H NMR (400 MHz, CDC13) : δ7.78 (d，6·8 Hz，1 H), 7.65 (d, J = 7.6 Hz，1 H), 7.46 (d, J = 2 Hz, 1 H)，7.30〜 7.23 (m, 2 H), 7.07 (d, 1.6 Hz, 1 H), 7.00-6.97 (m, 2 H), 6.90 (d, J= 8.4 Hz, 1 H), 3.92 (s, 3 H), 3.90 (s, 3 H) ； 13C NMR (100 MHz, CDC13) ： 6149.6 (C), 147.8(C), 143.6 (C), 134.9 (C), 第33頁/共58頁 201000484 131.2 (C), 129.6 (C), 124.8 (CH), 124.2 (CH), 123.4 (CH), 121.3 (C), 113.6 (CH), 111.6 (CH), 110.2 (CH), 109.6 (CH), 106.0 (CH), 56.2 (CH3), 56.1 (CH3) ； MS(EI) mlz 309(M+,88), 304(22), 287(10), 246 (7) ； HRMS(EI) mlz calcd for Ci8Hi5N02S ： 309.0824 ； found ： 309.0834.^—〇CH3 OCH3 2-(3,4-dimethoxyphenyl)-2H-benzo[4,5]thieno[2,3-c]pyrrole· Yield 84%, mp: 119-120 °C. IR (CHC13) : V2839, 1598, 1537, 1268, 1170, 726 cm'1 ; *H NMR (400 MHz, CDC13) : δ7.78 (d,6·8 Hz, 1 H), 7.65 (d, J = 7.6 Hz, 1 H), 7.46 (d, J = 2 Hz, 1 H), 7.30~ 7.23 (m, 2 H), 7.07 (d, 1.6 Hz, 1 H), 7.00-6.97 (m, 2 H), 6.90 (d , J = 8.4 Hz, 1 H), 3.92 (s, 3 H), 3.90 (s, 3 H) ; 13C NMR (100 MHz, CDC13): 6149.6 (C), 147.8(C), 143.6 (C), 134.9 (C), Page 33 of 58 201000484 131.2 (C), 129.6 (C), 124.8 (CH), 124.2 (CH), 123.4 (CH), 121.3 (C), 113.6 (CH), 111.6 ( CH), 110.2 (CH), 109.6 (CH), 106.0 (CH), 56.2 (CH3), 56.1 (CH3); MS (EI) mlz 309 (M+, 88), 304 (22), 287 (10), 246 (7) ; HRMS (EI) mlz calcd for Ci8Hi5N02S : 309.0824 ; found : 309.0834.

Example 14Example 14

6b R39 = OCH3 2.6- Bis-[4-(2,2 diphenyl-vinyl)-phenyl】-2,6-dHiydro-thieno[2,3-c;4,5-c’】dipyrrole (6a). Eluent for chromatography: EA/hex (1:9). Yield 59%, dark yellow solid, mp 272-274 °C. IR (neat), 2918, 2838, 1598, 1513, 1472, 1306, 1026, 694 cm1; ’H NMR (500 Hz，CDC13) δ 7.36-7.30 (m, 16H), 7.24-7.21 (m, 4H), 7.18 (d, J=2.0 Hz, 2H), 7.16 (d, ^9.0 Hz, 4H), 7.05 (d，/=8.0 Hz，4H)，7.01 (d，*7=1.5 Hz, 2H), 6.95 (s，2H); l3C NMR(125 MHz) δ 143.19, 142.62, 140.21，139.20, 134.76, 130.71, 130.32, 128.80, 128.23, 127.57, 127.53, 126.97, 122.92, 119.52, 109.42, 108.49; MS (El) m/z (relative intensity) 670 (M+, 100); HRMS (El) w/z calcd for C48H34N2S 670.2443, found 670.2432. 2.6- Bis-{4-[2,2-bis-(4-methoxy-phenyl)-vinyl]-phenyl}-2,6-dihydro-thieno[2,3-c;4,5-c ^dipyrrole (6b). Eluent for chromatography: EA/hex (1:9). Yield 60%, yellow solid, mp 228-230 °C. IR (neat), 2916, 1604, 1512, 1476, 1309, 1244, 1033, 832 cm'1; *H NMR (400Hz, CDC13) δ 7.25 (d, J=6.4 Hz, 4H), 7.18 (d, J=6.8 Hz, 4H), 7.13 (d, J=6A Hz, 4H), (7.1 l(s, 2H), 7.06 (d, J=8.8 Hz, 4H), 6.96 (d, J=1.6 Hz, 2H), 6.88 (d, J=2.00 Hz, 2H), 6.84 (d, J=8.0 Hz, 4H), 6.81 (d, J=8.8 Hz, 4H), 3.82 (s, 6H) 3.80 (s, 6H); 13C NMR (100 MHz) δ 159.28, 159.01, 141.84, 138.85, 136.18, 135.28, 132.53, 131.55, 130.48, 129.63, 128.79, 125.00, 122.91, 119.50, 114.10, 113.56, 109.38, 108.46, 55.27, 55.18; MS (El) m/z (relative intensity) 790 (M+, 100); HRMS (El) m/z calcd for C52H42N2O4S 790.2865, found 790.2863.6b R39 = OCH3 2.6- Bis-[4-(2,2 diphenyl-vinyl)-phenyl]-2,6-dHiydro-thieno[2,3-c;4,5-c']dipyrrole (6a). Eluent For chromatography: EA/hex (1:9). Yield 59%, dark yellow solid, mp 272-274 °C. IR (neat), 2918, 2838, 1598, 1513, 1472, 1306, 1026, 694 cm1; H NMR (500 Hz, CDC13) δ 7.36-7.30 (m, 16H), 7.24-7.21 (m, 4H), 7.18 (d, J = 2.0 Hz, 2H), 7.16 (d, ^9.0 Hz, 4H), 7.05 (d, /=8.0 Hz, 4H), 7.01 (d, *7 = 1.5 Hz, 2H), 6.95 (s, 2H); l3C NMR (125 MHz) δ 143.19, 142.62, 140.21, 139.20, 134.76, 130.71 , 130.32, 128.80, 128.23, 127.57, 127.53, 126.97, 122.92, 119.52, 109.42, 108.49; MS (El) m/z (relative intensity) 670 (M+, 100); HRMS (El) w/z calcd for C48H34N2S 670.2443 , found 670.2432. 2.6- Bis-{4-[2,2-bis-(4-methoxy-phenyl)-vinyl]-phenyl}-2,6-dihydro-thieno[2,3-c;4,5- c ^dipyrrole (6b). Eluent for chromatography: EA/hex (1:9). Yield 60%, yellow solid, mp 228-230 °C. IR (neat), 2916, 1604, 1512, 1476, 1309, 1244 , 1033, 832 cm'1; *H NMR (400Hz, CDC13) δ 7.25 (d, J=6.4 Hz, 4H), 7.18 (d, J=6.8 Hz, 4H), 7.13 (d, J=6A Hz, 4H), (7.1 l(s, 2H), 7.06 (d, J=8.8 Hz, 4H), 6.96 (d, J= 1.6 Hz, 2H), 6.88 (d, J=2.00 Hz, 2H), 6.84 (d, J=8.0 Hz, 4H), 6.81 (d, J=8.8 Hz, 4H), 3.82 (s, 6H) 3.80 ( s, 6H); 13C NMR (100 MHz) δ 159.28, 159.01, 141.84, 138.85, 136.18, 135.28, 132.53, 131.55, 130.48, 129.63, 128.79, 125.00, 122.91, 119.50, 114.10, 113.56, 109.38, 108.46, 55.27, 55.18; MS (El) m/z (relative intensity) 790 (M+, 100); HRMS (El) m/z calcd for C52H42N2O4S 790.2865, found 790.2863.

Example 15 第34頁/共58頁 201000484Example 15 Page 34 of 58 201000484

2,6-Di-naphthalen-l-yl-2,6-dihydro-thieno[2,3-c;4,5-c,]dipyrrole. Eluent for chromatography: EA/hex (1:9). Yield 45%, yellow solid，mp 240-241 °C. IR (neat)，3153, 3049, 1728, 1595, 1575, 1478,1401,1306,1095, 1019, 802 cm'1; ]H NMR (400Hz, CDC13) δ 7.93-7.87 (m, 6H), 7.53-7.48 (m, 8H), 7.21 (d, J=1.6 Hz, 2H), 7.00 (d, J=\.6 Hz, 2H); 13C NMR (100 MHz) δ 138.50, 134.27, 129.93, 128.25, 128.06, 128.01, 127.03, 126.59, 125.23, 123.60, 123.35, 122.02, 113.73, 112.83; MS (El) m/z (relative intensity) 414 (M+, 100); HRMS (El) m/z calcd for C28Hi8N2S 414.1191, found 414.1181.2,6-Di-naphthalen-l-yl-2,6-dihydro-thieno[2,3-c;4,5-c,]dipyrrole. Eluent for chromatography: EA/hex (1:9). Yield 45 %, yellow solid, mp 240-241 °C. IR (neat), 3153, 3049, 1728, 1595, 1575, 1478, 1401, 1306, 1095, 1019, 802 cm'1; ]H NMR (400Hz, CDC13) δ 7.93-7.87 (m, 6H), 7.53-7.48 (m, 8H), 7.21 (d, J=1.6 Hz, 2H), 7.00 (d, J=\.6 Hz, 2H); 13C NMR (100 MHz ) δ 138.50, 134.27, 129.93, 128.25, 128.06, 128.01, 127.03, 126.59, 125.23, 123.60, 123.35, 122.02, 113.73, 112.83; MS (El) m/z (relative intensity) 414 (M+, 100); HRMS ( El) m/z calcd for C28Hi8N2S 414.1191, found 414.1181.

Example 16Example 16

8-Benzenesulfonyl-2-[4-(2,2-diphenyl-vinyl)-phenyl]-2,8-dihydro-2,8-diaza-cyclopenta[a]indene. Mp 178-180°C FTIR (neat), 3056, 1626, 1604, 1518, 1494, 1468, 1446, 1417, 1368, 1283, 1236, 1181, 1170, 1027, 951, 873, 826 cm '.'HNMR (400 MHz, CDC13) δ 8.02(d, J=8.0Hz, 1H), 7.81(d, J=8.4Hz, 2H), 7.52(d, J=8.0Hz, 1H), 7.43(t,^7.6Hz 1 H), 7.37-7.17(m, 16H), 7.13(d, ^=2.0Hz, 2H), 7.10 (d, J=8.8Hz, 2H), 6.99(s, 1H). 13C NMR(lOOMHz) 143.06, 142.39, 140.18, 139.17, 137.29, 135.38, 133.48, 132.94, 130.76, 130.30, 128.80, 128.24, 127.63, 127.52, 126.79, 126.70, 125.32, 124.44, 123.93, 120.80, 120-01, 119.17, 115.00, 106.91，101.53. HRMS calced for C36H26N202S 550.1715, 第35頁/共58頁 201000484 found 550.17248-Benzenesulfonyl-2-[4-(2,2-diphenyl-vinyl)-phenyl]-2,8-dihydro-2,8-diaza-cyclopenta[a]indene. Mp 178-180°C FTIR (neat) , 3056, 1626, 1604, 1518, 1494, 1468, 1446, 1417, 1368, 1283, 1236, 1181, 1170, 1027, 951, 873, 826 cm '.'HNMR (400 MHz, CDC13) δ 8.02 (d, J=8.0Hz, 1H), 7.81(d, J=8.4Hz, 2H), 7.52(d, J=8.0Hz, 1H), 7.43(t,^7.6Hz 1 H), 7.37-7.17(m, 16H ), 7.13(d, ^=2.0Hz, 2H), 7.10 (d, J=8.8Hz, 2H), 6.99(s, 1H). 13C NMR(lOOMHz) 143.06, 142.39, 140.18, 139.17, 137.29, 135.38, 133.48, 132.94, 130.76, 130.30, 128.80, 128.24, 127.63, 127.52, 126.79, 126.70, 125.32, 124.44, 123.93, 120.80, 120-01, 119.17, 115.00, 106.91, 101.53. HRMS calced for C36H26N202S 550.1715, page 35/ Total 58 pages 201000484 found 550.1724

Example 17Example 17

8-Benzenesulfonyl-2-[4-(2,2-di-p-tolyl-vinyl)-phenyI]-2,8-dihydro-2,8 -diaza-cyclopenta[a]indene. FTIR (neat), 3151，3033, 3018, 2922, 1627, 1609, 1513, 1447, 1365, 1284, 1236, 1170, 1115, 1026, 952, 868, 827 cm-1. 'HNMR(600 MHz, CDC13)5 8.03(d, J=8.4Hz, 1H), 7.83(d, J=7.2Hz, 2H), 7.52(d, J=7.2Hz, 1H), 7.43(m, 1 H), 7.32(d, /=8.4Hz, 2H), 7.28(d, J=8.0Hz, 2H), 7.25(d, J=6.8Hz, 4H),720-7.10(m, 12H), 6.92(s, 1H), 2.41(s, 3 H), 2.36(s,3H). 13C NMR(125MHz) 142.91, 142.30, 140.50 ,138.88, 137.49, 137.28, 137.20, 135.67, 133.51, 132.82, 130.65, 130.15, 129.48, 128.91, 128.82, 127.46, 126.68, 125.70, 125.28, 124.45, 123.93, 120.79, 119.92, 119.05, 114.97, 106.89, 101.50, 21.32, 21.11 Example 18 h3co8-Benzenesulfonyl-2-[4-(2,2-di-p-tolyl-vinyl)-phenyI]-2,8-dihydro-2,8-diaza-cyclopenta[a]indene. FTIR (neat), 3151 , 3033, 3018, 2922, 1627, 1609, 1513, 1447, 1365, 1284, 1236, 1170, 1115, 1026, 952, 868, 827 cm-1. 'HNMR(600 MHz, CDC13)5 8.03(d, J = 8.4 Hz, 1H), 7.83 (d, J = 7.2 Hz, 2H), 7.52 (d, J = 7.2 Hz, 1H), 7.43 (m, 1 H), 7.32 (d, /=8.4 Hz, 2H) , 7.28(d, J=8.0Hz, 2H), 7.25(d, J=6.8Hz, 4H), 720-7.10(m, 12H), 6.92(s, 1H), 2.41(s, 3 H), 2.36 (s, 3H). 13C NMR (125MHz) 142.91, 142.30, 140.50, 138.88, 137.49, 137.28, 137.20, 135.67, 133.51, 132.82, 130.65, 130.15, 129.48, 128.91, 128.82, 127.46, 126.68, 125.70, 125.28, 124.45 , 123.93, 120.79, 119.92, 119.05, 114.97, 106.89, 101.50, 21.32, 21.11 Example 18 h3co

8-BenzenesulfonyI-2-{4-[2,2-bis-(4-methoxy-phenyl)-vinyl]-phenyI}-2 第36頁/共58頁 201000484 ,8-dihydro-2,8-diaza-cyclopenta[a]indene. FTIR (neat), 3156, 3027, 2963, 1605, 1582, 1513, 1445, 1358, 1284, 1244, 1171, 1111, 1029, 947, 832 cm'1. !H NMR (400 MHz, CDC13) δ 8.01(d, J=8.4Hz, 1H), 7.81(d, J=8.4Hz, 2H), 7.52(d, J=7.6Hz, 1H), 7.41(m, 1 H), 7.30(d, J=7.6Hz, 2H), 7.28(s,lH) , 7.24(d, J=7.6Hz, 4H),7.19(d, J=7.6Hz, 1H), 7.16-7.09(m, 6H), 6.89(d, J=7.6Hz, 2H), 6.86 (d, J=9.2Hz, 3H), 3.84(s, 3 H), 3.79(s,3H). 13C • NMR(100MHz) HRMS calced for C38H30N2〇4S 610.1926, found 610.1939 根據本實施例，由於上述之具有雜多環結構之共軛化合物包括良好的熱穩定性與高的三重態能階差等優點，所以當上述具有雜多環結構之共軛化合物應用於有機電激發光 (electroluminescence)元件與/或螢光（Fluorescence)元件中，特別是應用於螢光元件之發光材料，或是應用於有機電激發光元件與/或填光元件中的主發光體材料（host material)時，將可有效延長元件使用壽命，以及提高元件的發光效率。此外，上述之具有雜多環結構之共扼化合物亦可應用於其他有機電子元件（organic electronic devices)。上述之有機電子元件可以是有機發光元件、有機太陽能電池、有機薄膜電晶體、有機光導體、或是其他習知該項技藝者所熟悉之有機半導體元件。本發明之第二實施例揭露一種具有多層結構（multilayer structure)之有機發光二極體（OLED)，一般而言，OLED元件發光的顏色主要決定於元件内具有螢光特性的有機材料，因此OLED 可由在主發光體(host)中混入少量的高發光效率客發光體(guest)來第37頁/共58頁 201000484 提高載子的再結合效率，這些客發光體具有比主發光體小的能隙、高的發光效率以及比主發光體短的再結合生命期等特性，因此將主發光體的激子（exciton)藉由能量轉移的過程轉移至客發光體上進行快速且有效率的再結合。這除了提高發光的效率外，也可使發光的顏色橫跨整個可見光區。客發光體（guest emitter)常以共蒸鍍（co-evaporation)或分散 (dispersion)方式與主發光體共同使用，並以能量轉移（energy transfer)或載子捕獲（carrier trap)方式接受來自被激發的主發光體能量，而導致不同顏色（red，green，blue)的產生且增強元件的發光效率" 根據本實施例，上述之有機發光元件包含一對電極與至少一有機層位於上述的電極之間。其中上述的至少一有機層包括一發光層，且上述的有機層中至少有一層包含一具有雜多環結構之共輛化合物，上述具有雜多環結構之共輛化合物之一般結構如下：8-Benzenesulfony I-2-{4-[2,2-bis-(4-methoxy-phenyl)-vinyl]-phenyI}-2 Page 36 of 58 Page 201000484, 8-dihydro-2,8-diaza- Cyclopenta[a]indene. FTIR (neat), 3156, 3027, 2963, 1605, 1582, 1513, 1445, 1358, 1284, 1244, 1171, 1111, 1029, 947, 832 cm'1. !H NMR (400 MHz , CDC13) δ 8.01(d, J=8.4Hz, 1H), 7.81(d, J=8.4Hz, 2H), 7.52(d, J=7.6Hz, 1H), 7.41(m, 1 H), 7.30( d, J = 7.6 Hz, 2H), 7.28 (s, lH), 7.24 (d, J = 7.6 Hz, 4H), 7.19 (d, J = 7.6 Hz, 1H), 7.16-7.09 (m, 6H), 6.89(d, J=7.6Hz, 2H), 6.86 (d, J=9.2Hz, 3H), 3.84(s, 3 H), 3.79(s,3H). 13C • NMR(100MHz) HRMS calced for C38H30N2〇 4S 610.1926, found 610.1939 According to the present embodiment, since the above conjugated compound having a heteropolycyclic structure includes advantages such as good thermal stability and high triplet energy level difference, when the above conjugate having a heteropolycyclic structure The compound is applied to an organic electroluminescence element and/or a fluorescent element, in particular to a luminescent material of a fluorescent element, or to an organic electroluminescent element and/or a filling element. When the main illuminant material is used, it will effectively extend the life of the component and improve the luminous efficiency of the component. Further, the above conjugated compound having a heteropolycyclic structure can also be applied to other organic electronic devices. The above-mentioned organic electronic component may be an organic light-emitting element, an organic solar cell, an organic thin film transistor, an organic photoconductor, or other organic semiconductor element familiar to those skilled in the art. A second embodiment of the present invention discloses an organic light emitting diode (OLED) having a multilayer structure. Generally, the color of the OLED element is mainly determined by an organic material having a fluorescent property in the element, and thus the OLED is The recombination efficiency of the carrier can be improved by mixing a small amount of high luminous efficiency guest in the main illuminator (page 37), which has a smaller energy than the main illuminator. The gap, the high luminous efficiency, and the recombination lifetime of the main illuminator, so that the exciton of the main illuminator is transferred to the guest illuminant by the process of energy transfer for rapid and efficient re Combine. In addition to improving the efficiency of illumination, this also allows the color of the illumination to span the entire visible region. The guest emitter is often used in conjunction with the main illuminator by co-evaporation or dispersion, and is accepted by energy transfer or carrier trap. Exciting the main illuminant energy, resulting in the generation of different colors (red, green, blue) and enhancing the luminous efficiency of the element. According to the embodiment, the above organic light emitting element comprises a pair of electrodes and at least one organic layer located at the above Between the electrodes. Wherein at least one of the organic layers comprises a light-emitting layer, and at least one of the organic layers comprises a compound having a heteropolycyclic structure, and the general structure of the above-mentioned compound having a heteropolycyclic structure is as follows:

第38頁/共58頁 201000484 其中，A係選自S、N等原子，A可以更包含一取代基。上述結構中的R1〜R19可以相同或不同’且R1〜R19係獨立選自下列族群中之一者：氫原子、鹵素原子（例如：敗、氣、溴、蛾）；芳香基；鹵素取代的芳香基；C卜C20鹵烷基取代的芳香基；芳香烷基；芳香烯基；C1-C20鹵烷基取代的芳香烷基；具芳香基取代的 C1-C20烷基；C1-C20烷基、C1-C20環烷基（例如：甲基、乙基、丁基、環己基）；C1-C20 烧氧基（alkoxy group);胺基（amino group);具芳香基取代的胺基；具C1-C20烷基取代的胺基；亞石肖酸基（nitrile group) ’·硝基（nitro group);羰基（以如⑽ g_p); 氰基(cyano group，_CN);具有取代基的芳香胺基；雜環基團；具有環狀的胺基(piperidine，morpholine)。在根據本實施例之一較佳範例中，當上述具有雜多環結構之共輥化合物中之A係表示-N原子時，N之取代基侧自下列群組中之一者，然而N之取代基並不以下列群組為限：Page 38 of 58 201000484 wherein A is selected from atoms such as S and N, and A may further comprise a substituent. R1 to R19 in the above structure may be the same or different 'and R1 to R19 are independently selected from one of the following groups: a hydrogen atom, a halogen atom (for example, a gas, a bromine, a moth); an aromatic group; a halogen-substituted one. Aromatic group; C-C20 haloalkyl-substituted aryl; arylalkyl; aromatic alkenyl; C1-C20 haloalkyl-substituted arylalkyl; aryl-substituted C1-C20 alkyl; C1-C20 alkyl , C1-C20 cycloalkyl (for example: methyl, ethyl, butyl, cyclohexyl); C1-C20 alkoxy group; amino group; amine group substituted with an aryl group; C1-C20 alkyl-substituted amine group; nitrile group 'nitro group; carbonyl group (such as (10) g_p); cyano group (_CN); aromatic having a substituent Amino group; heterocyclic group; having a cyclic amino group (piperidine, morpholine). In a preferred embodiment according to this embodiment, when the A system of the above-mentioned common roll compound having a heteropolycyclic structure represents a -N atom, the substituent side of N is from one of the following groups, whereas N is Substituents are not limited to the following groups:

第39頁/共58頁 201000484Page 39 of 58 201000484

在根據本實施例之一較佳範例中，上述具有雜多環結構之共輛化合物中相鄰之R2與r3、R4與r5、r5與r6、R6與R7、r7與 R8、R9 與 R1Q、R1()與 R】1、R11 與 R12、R12 與 R13、R15 與、r18 與R19等至少有一組可以是形成一芳香環、一芳香雜環、〜環烯基或是一雜環烯基之任意原子團。上述的芳香瓖、芳香雜環、環烯基或是雜環烯基等可以分別是五元環、六元環、威是七元環，且上述之芳香環、芳香雜環、環烯基或是雜環烯基等可以更包含一個或多個取代基。上述之取代基可以相同或不同’且上述取代基係獨立選自下列族群中之一者：氫原子、鹵素原子（例如：氟、亂、漠、峨）、方香基、_素取代的芳香基、鹵素取代的方香燒基、鹵烷基取代的芳香基、齒烷基取代的芳香烷基、芳香基取代的 C1-C20 烷基、C1-C20 烷基、C1-C20 環烷基、C1-C20 烷氧基（alkoxy group)、C1-C20取代的胺基（amino group)、具有取代基的芳香胺基[例如苯胺基（aniline)]、亞确酸基(nitrile)、硝’基(nitro)、幾基 (carbonyl)、氰基（eyano，_CN)、鹵素取代的C1-C20烷基（例如三氟甲烷基，CF3)、雜環取代基團。上述R2〜R19中未成環之取代基可以相同或不同，且上述R2〜第40頁/共58頁 201000484 R19中未成環之取代基係獨立選自下列族群之一者：氫原子、鹵素原子、C1-C20 烧基(alkyl group)、C1-C20 環烧基、院氧基(alkoxyl group)、鹵素取代的C1-C20烧基、C1-C20取代的胺基（amino group)、Cl-C20 酿基（acyl group)、Cl-C20 S旨基（ester group)、Cl-C20 酿胺基(amide group)、芳香基、鹵素取代的芳香基、鹵素取代的芳香烷基、芳香基取代的烯基、lS烷基取代的芳香基、鹵烷基取代的芳香炫基、氰基(cyano)、琐基(nitro)、共輛芳香環基團（aromatic group )、芳香雜環基團。根據本實施例，前述之芳香基團可以是包含苯基(phenyl)、萘基（naphthyl)、聯苯基（diphenyl)、蒽基（anthryl)、苯并菲基 (pyrenyl)、菲基（phenanthryl)與苐基（fluorenyl)或其他形式之多苯環取代基。前述的環烯基團包含環己烯(cyclohexene)、環己二烯 (cyclohexadiene)、環戊浠（cyclopentene)與環戊二稀 (cyclopentadiene)或其他形式之環稀。前述之雜環基團包括β底喃 (卩5^3狀）、11底洛琳(？>^1'〇1丨狀）、°夫喃（£11以11)、苯并°夫喃〇6112〇£11^11)、喧吩(thiophene)、苯并 °塞吩(benzothiophene)、η比咬(pyridine)、喧琳（quinoline)、異啥淋（isoquinoline)、D比》秦（pyrazine)、續咬 (pyrimidine)、°比洛(pyrrole)、0比0坐(pyrazole)、味吐(imidazole)、0弓| 口朵（indole)、^^(thiazole)、異隹《^(isothiazole)、嗔。坐（oxazole)、異°惡°坐（isoxazole)、苯并嘆β坐（benzothiazole)、苯并α惡唾 (benzoxazole)、二氮菲（phenanthroline)或其他形式之雜環。第41頁/共58頁 201000484 在根據本實施例之一較佳範例中，上述具有雜多環結構之共軛化合物可以是應用於上述有機發光元件中之發光層。在根據本實施例之另一較佳範例中，上述具有雜多環結構之共輛化合物可以是應用於上述有機發光元件中之發光層之一主體材料。上述之發光層可以更包含一客發光體材料，且前述之客發光體材料包含一過渡金屬錯合物。上述之過渡金屬錯合物可以是選自下列族群之一者：銥(Ir)、鉑(Pt)、餓(Os)、銅（cu)、铑(Rh)、銪（Eu)、釕（Ru) 等。上述之客發光體材料可以是藍色、綠色、紅色等顏色之磷光材料。在根據本實施例之另一較佳範例中，上述具有雜多環結構之共軛化合物可以是應用於上述有機發光元件中之電洞傳導層。在根據本實施例之另一較佳範例中，上述具有雜多環結構之共軛化合物可以是應用於上述有機發光元件中之電子傳導層。形成有機發光元件的一般流程取已餘刻電路圖的ITO破璃，加入中性清潔劑：去離子水=1 : 5〇的清洗液，置於超音波雜”驗5分鐘，接著雜摘狐玻璃，再依序將玻璃置於5〇 mL的去離子水、電子級丙财震盡5分鐘，最後以氣氣吹乾。將清潔後的™玻璃放置在紫外光韻機内，時間設定為5分鐘，取出後固定在基板上（ITO面朝下），放人_中抽真空，直到腔體的真空度達到⑽t。咖進行蒸物之步驟。蒸細之條件為有機物鍍膜速率控制在1〜2 A/s之間，將所肝所期望的有_依序驗，而金屬鍍膜之速率鎂為5A/s，銀為0.5 A/s，餻.相_ … —0 : 1，鎂銀共蒸鍍之金屬膜厚為第42頁/共58頁 201000484 55 nm ’最後再鍵上一層loo nm的銀作為保護層。如果金屬選擇的是氣化鐘/銘系統，首先必須以速率為0.1 A/s蒸鍍氟化鋰，其膜厚控制為1啲，接著再鍍上一層100 nm的鋁作為保護層。於鍍膜期間，元件之旋轉速率為 20 rpm，蒸鍍結束後須等待20分鐘讓金屬電極降溫，才可將腔體回充氛氣使之回復常壓。另一方面，OLED元件製備完成後，藉由Hitach F- 4500 spectra scan spectrometer量測元件的電激螢光頻譜（el spectra)與CIE 座才示圖（CIE coordination )，此外，措由 Keithley 2400 programmable voltage-current source 量測元件的電流（current)、電壓（v〇ltage) 與亮度（brightness)等性質。上述之量測儀器皆在一大氣壓下室溫操作（約20 °C )。In a preferred example according to this embodiment, the adjacent R2 and r3, R4 and r5, r5 and r6, R6 and R7, r7 and R8, R9 and R1Q, of the compound compound having a heteropolycyclic structure, At least one of R1() and R]1, R11 and R12, R12 and R13, R15 and r18 and R19 may form an aromatic ring, an aromatic heterocyclic ring, a cycloalkenyl group or a heterocycloalkenyl group. Any atomic group. The above aromatic oxime, aromatic heterocyclic ring, cycloalkenyl group or heterocycloalkenyl group may be a five-membered ring, a six-membered ring, or a seven-membered ring, and the above aromatic ring, aromatic heterocyclic ring, cycloalkenyl group or It is a heterocyclic alkenyl group or the like which may further contain one or more substituents. The above substituents may be the same or different 'and the above substituents are independently selected from one of the following groups: a hydrogen atom, a halogen atom (for example, fluorine, chaos, desert, hydrazine), a aryl group, a aryl group substituted aryl group, Halogen-substituted aryl, haloalkyl-substituted aryl, dentate-substituted arylalkyl, aryl-substituted C1-C20 alkyl, C1-C20 alkyl, C1-C20 cycloalkyl, C1- C20 alkoxy group, C1-C20 substituted amino group, substituted aromatic amine group [eg aniline], nitrile (nitrile), nitric acid (nitro) , carbonyl, cyano (-CN), halogen-substituted C1-C20 alkyl (eg, trifluoromethyl, CF3), heterocyclic substituent. The unsubstituted substituents in the above R2 to R19 may be the same or different, and the unsubstituted substituents in the above R2 to 40/en 58 pages 201000484 R19 are independently selected from one of the following groups: a hydrogen atom, a halogen atom, C1-C20 alkyl group, C1-C20 cycloalkyl group, alkoxyl group, halogen-substituted C1-C20 alkyl group, C1-C20 substituted amino group, Cl-C20 Acyl group, Cl-C20 S ester group, Cl-C20 amide group, aryl group, halogen-substituted aryl group, halogen-substituted aryl group, aryl-substituted alkenyl group And an alkyl group-substituted aryl group, a haloalkyl-substituted aryl group, a cyano group, a nitro group, an aromatic group, and an aromatic heterocyclic group. According to this embodiment, the aforementioned aromatic group may be composed of a phenyl group, a naphthyl group, a diphenyl group, an anthryl group, a pyryryl group, a phenanthryl group. And fluorenyl or other forms of polyphenyl ring substituents. The aforementioned cycloalkenyl group comprises cyclohexene, cyclohexadiene, cyclopentene and cyclopentadiene or other forms of cycloaliphatic. The aforementioned heterocyclic group includes β-pyran (卩5^3-like), 11-Dylon (?>^1'〇1丨), °fu (£11 to 11), benzofuran 〇6112〇£11^11), thiophene, benzothiophene, pyridine, quinoline, isoquinoline, D ratio, rhazine ), pyrimidine, pyrrole, pyrazole, imidazole, 0 bow | indole, ^^ (thiazole), isoquinone "^ (isothiazole ), hehe. Oxazole, isosazole, benzothiazole, benzoxazole, phenanthroline or other forms of heterocyclic ring. Page 41 of 58 201000484 In a preferred embodiment according to this embodiment, the above conjugated compound having a heteropolycyclic structure may be a light-emitting layer applied to the above organic light-emitting element. In another preferred embodiment according to this embodiment, the above-described compound compound having a heteropolycyclic structure may be one of the host materials of the light-emitting layer applied to the above organic light-emitting element. The luminescent layer described above may further comprise a guest illuminant material, and the aforementioned guest illuminant material comprises a transition metal complex. The above transition metal complex may be one selected from the group consisting of iridium (Ir), platinum (Pt), hungry (Os), copper (cu), rhodium (Rh), ruthenium (Eu), ruthenium (Ru). ) Wait. The above guest illuminant material may be a phosphorescent material of a color such as blue, green or red. In another preferred embodiment according to this embodiment, the above conjugated compound having a heteropolycyclic structure may be a hole conducting layer applied to the above organic light-emitting element. In another preferred embodiment according to this embodiment, the above conjugated compound having a heteropolycyclic structure may be an electron conductive layer applied to the above organic light-emitting element. The general procedure for forming an organic light-emitting element is to take the ITO glass of the remaining circuit diagram, add a neutral detergent: deionized water = 1: 5 清洗 cleaning solution, placed in the ultrasonic wave for 5 minutes, then the fox glass Then, place the glass in 5 〇mL of deionized water, electronic grade C. sin for 5 minutes, and finally blow it off with air. Place the cleaned TM glass in the UV machine, set the time to 5 minutes. After being taken out, it is fixed on the substrate (the ITO face is facing down), and the vacuum is released until the vacuum degree of the cavity reaches (10) t. The step of steaming the product is carried out. The evaporation condition is controlled by the organic coating rate of 1 to 2 A. Between /s, the liver is expected to have a sequential test, while the metal coating rate of magnesium is 5A / s, silver is 0.5 A / s, 餻. phase _ ... - 0: 1, magnesium and silver co-evaporation The thickness of the metal film is 42 pages/58 pages 201000484 55 nm 'The last layer of loo nm silver is used as the protective layer. If the metal is selected as the gasification clock/ming system, the rate must first be 0.1 A/s. Evaporation of lithium fluoride, the film thickness of which is controlled to 1 啲, followed by plating a layer of 100 nm of aluminum as a protective layer. During the film, the rotation rate of the component is 20 rpm, and after the vapor deposition is finished, it is necessary to wait for 20 minutes for the metal electrode to cool down, so that the cavity can be backfilled with the atmosphere to return to normal pressure. On the other hand, after the preparation of the OLED element is completed, The electro-spectrum spectrum (el spectra) of the Hitach F- 4500 spectra scan spectrometer and the CIE coordination diagram (CIE coordination), in addition, the current of the Keithley 2400 programmable voltage-current source measuring component (current ), voltage (v〇ltage) and brightness (brightness), etc. The above measuring instruments are operated at room temperature under atmospheric pressure (about 20 ° C).

Example 19 藉由上述形成有機發光元件的一般流程，以2,6_Bis_【4-(2»2 diphenyl-vinyl)-phenyl】-2,6-dihydro-thieno[2,3-c;4,5-c，]dipyrr〇le (6a)為螢光發光材料，以形成有機發光元件，前述元件之個別結構如后：元件 A: 6a(40 nm)/Alq(40 nm)/LiF/Al 元件 B: 6a(40 nm)/TPBI(40 nm)/LiF/Al 元件 C: NPB(40 nm)/6a(10 nm)/TPBI(40 nm)/LiF/Al 元件A、B、與C之光學性質與效率量測結果如下表i〜表3所示。第43頁/共58頁 201000484 表1、元件A之量測結果 6a(40 nm)/Alq(40 nm)/LiF/Al 最大放光波長 CIE, X CIE, Y 半高全寬 (FWHM) 最大亮度 (Max Luminance) 502 0.21 0.43 84 22009 電流密度100mA/cm2 量子效率 (QE) 放光效率 (Cd/A) 發光效率/功率 (lm/w) 啟動電壓 (V) 亮度 (Luminance) 1.600 4.158 1.807 7.24 4153 電流密度20mA/cm2 量子效率 1.484 放光效率 (Cd/A) 發光效率/功率 (lm/w) 啟動電壓 (V) 亮度 (Luminance) 3.856 2.159 5.61 778 ------ 表2、元件B 之量測結果 - 最大放光 -- 6a(40 nm)/TPBI(40 nm)/LiF/Al τ~ CIE, X — CIE, Y 半高全寬 (FWHM) 最大亮度 (Max Luminance) 0.32 78 26812 電流密度100mA/cm' 發光效率/功率 (lm/w) 啟動電壓 (V) 亮度 (Luminance) 3.347 5.56 5908 電流密度20mA/cm' 發光效率/功率 (lm/w) 啟動電壓 (V) 亮度 (Luminance) 4.144 4.13 1104Example 19 By the above general procedure for forming an organic light-emitting element, 2,6_Bis_[4-(2»2 diphenyl-vinyl)-phenyl]-2,6-dihydro-thieno[2,3-c;4,5- c,]dipyrr〇le (6a) is a fluorescent material to form an organic light-emitting element, and the individual structures of the foregoing elements are as follows: Element A: 6a (40 nm) / Alq (40 nm) / LiF / Al element B: 6a (40 nm) / TPBI (40 nm) / LiF / Al element C: NPB (40 nm) / 6a (10 nm) / TPBI (40 nm) / LiF / Al elements A, B, and C optical properties and The efficiency measurement results are shown in Tables i to 3 below. Page 43 of 58 Page 201000484 Table 1, Measurement results of component A 6a (40 nm) / Alq (40 nm) / LiF / Al Maximum emission wavelength CIE, X CIE, Y Full width at half maximum (FWHM) Maximum brightness ( Max Luminance) 502 0.21 0.43 84 22009 Current Density 100mA/cm2 Quantum Efficiency (QE) Light Emitting Efficiency (Cd/A) Luminous Efficiency/Power (lm/w) Starting Voltage (V) Luminance 1.600 4.158 1.807 7.24 4153 Current Density 20mA/cm2 Quantum efficiency 1.484 Light-emitting efficiency (Cd/A) Luminous efficiency/power (lm/w) Starting voltage (V) Luminance 3.856 2.159 5.61 778 ------ Table 2, Quantity of component B Measurement results - Maximum light emission - 6a (40 nm) / TPBI (40 nm) / LiF / Al τ ~ CIE, X - CIE, Y Full width at half maximum (FWHM) Maximum brightness (Max Luminance) 0.32 78 26812 Current density 100mA / Cm' luminous efficiency / power (lm / w) starting voltage (V) brightness (Luminance) 3.347 5.56 5908 current density 20mA / cm ' luminous efficiency / power (lm / w) starting voltage (V) brightness (Luminance) 4.144 4.13 1104

第44頁/共58頁 201000484 表3、元件C之量測結果 NPB(40nmV6ail0 nmWPBIMO nmVLiF/Al 最大放光波長 CIE, X CIE, Y 半高全寬 (FWHM) 最大亮度 (Max Luminance) 470 0.15 0.21 78 18922 電流密度1 〇〇 mA/cm2 ---—- 量子效率 (QE) 2.668 放光效率 4.121 ---1 發光效率/功率 (lm/w) 啟動電壓 (V) 亮度 (Luminance) 2.573 5.03 4119 電流密度20 mA/cm2 量子效率 (QE) 2.542~~ 放光效率 _JCd/A) 發光效率/功率 (lm/w) 啟動電壓 (V) 亮度 (Luminance) 796 3.926 3.285 3.76 從表1至表3的數據可看出，根據本說明書之具有雜多環結構之共扼化合物可作為螢光發光材料以應用在有機發光二極體上，且所製備之元件可放出藍光。更好的是，上述之元件具有高亮度、高電流效率及優異的⑽座標等相當具有產錢用價值之效果。顯然地’依照上面體系中的描述，，本發明可能有許多的修正與差異。因此需要在其附加的權利要求只 < 範圍内加以理解，除了上述洋細的描述外，本發明還可以廣、、多1, > 之地在其他的體系中施行。上述僅為本發明之較佳體系而已， ^ 用以限定本發明之申請專利範圍；凡其它未脫離本發明所揭精神下所完成的等效改變或修飾，均應包含在下述申請專利範圍内第45頁/共58頁Page 44 of 58 Page 201000484 Table 3. Measurement results of component C NPB (40nmV6ail0 nmWPBIMO nmVLiF/Al maximum emission wavelength CIE, X CIE, Y full width at half maximum (FWHM) maximum brightness (Max Luminance) 470 0.15 0.21 78 18922 Current density 1 〇〇 mA/cm2 ----- Quantum efficiency (QE) 2.668 Light-emitting efficiency 4.121 ---1 Luminous efficiency / power (lm / w) Starting voltage (V) Luminance 2.573 5.03 4119 Current density 20 mA/cm2 Quantum efficiency (QE) 2.542~~ Light-emitting efficiency_JCd/A) Luminous efficiency/power (lm/w) Starting voltage (V) Luminance 796 3.926 3.285 3.76 Data from Table 1 to Table 3. It can be seen that the ruthenium compound having a heteropolycyclic structure according to the present specification can be applied as a fluorescent luminescent material to an organic light-emitting diode, and the prepared element can emit blue light. More preferably, the above-mentioned components have high brightness, high current efficiency, and excellent (10) coordinates, which are quite valuable for producing money. Obviously, the invention may have many modifications and differences in accordance with the description in the above system. Therefore, it is to be understood that the scope of the appended claims is only <RTIgt;<RTIgt;</RTI>> The above is only the preferred system of the present invention, and is intended to be used to define the scope of the claims of the present invention. Any equivalent changes or modifications made without departing from the spirit of the invention should be included in the scope of the following claims. Page 45 of 58

Claims

201000484 十、申請專利範圍： ι· 一種具有雜多環結構之共軛化合物’該具有雜多環結構之共扼化合物之一般式如下：201000484 X. Patent application scope: ι· A conjugated compound having a heteropolycyclic structure The general formula of the conjugated compound having a heteropolycyclic structure is as follows:

其中，A係選自S、N等原子，入可以更包含一取代基；上述結構中的R1〜R19可以相同或不同，且Ri〜Rl9係獨立選自下列族群中之一者：氫原子、鹵素原子、芳香基、鹵素取代的芳香基、 C1-C20鹵炫基取代的芳香基、芳香烷基、芳香烯基、cl_c2〇鹵烷基取代的芳香炫基、具芳香基取代的cl_C2〇烷基；C1-C20 烧基、C1-C20 %烧基、C1-C20 烧氧基（alkoxy group)、胺基 (amino group)、具芳香基取代的胺基、具C1-C20烷基取代的胺基、亞硝酸基（nitroso group)、确基（nitro group)、幾基（carbonyl group)、氰基（cyano group，-CN)、具有取代基的芳香胺基、雜環基團、具有環狀的胺基(piperidine，morpholine)。 2.如申請專利範圍第1項所述之具有雜多環結構之共軛化合物，第46頁/共58頁 201000484 其中上述之芳香基包含下列族群中之一者：苯基(phenyl)、萘基 (naphthyl)、聯苯基（diphenyl)、蒽基（anthryl)、苯并菲基 (pyrenyl)、菲基(phenanthry 1)與二苯并五環（fluorene)或其他形式之多苯環取代基。 3.如申請專利範圍第1項所述之具有雜多環結構之共扼化合物，其中上述之雜J哀基團包含下列族群中之一者：痕喃（pyrane)、派咯啉（pyrroline)、呋喃（furan)、苯并呋喃（benzofuran)、噻吩 (thiophene)、苯并0塞吩(benzothiophene)、口比咬(pyridine)、啥琳 (quinoline)、異喧淋（isoquinoline)、β比唤（pyrazine)、嘲咬 (pyrimidine)、口比略（pyrrole)、〇比峻（pyrazole)、咪0坐（imidazole)、 0引口朵（indole)、售0坐（thiazole)、異養坐（isothiazole)、°惡0坐 (oxazole)、異 °惡哇（isoxazole)、苯并嗟 n坐（benzothiazole)、苯并噁口坐（benzoxazole)、1，2,4_ 三-惡嗤（l，2,4-triazole)、1，2,3-三噁唑 (l，2,3-triazole)、1，2,3,4-四噁唾（l，2,3,4-tetraazole)，與二氮菲 (phenanthroline) 〇 4·如申請專利範圍第1項所述之具有雜多環結構之共輛化合物，其中上述之環烯基團包含下列族群中之一者：環己烯 (cyclohexene)、環己二烯（cyclohexadiene)、環戊烯（cyclopentene) 與環戊二烯（cyclopentadiene)。 5.如申請專利範圍第1項所述之具有雜多環結構之共軛化合物，其中上述具有雜多環結構之共軛化合物之一般式如下：第47頁/共58頁 201000484Wherein, A is selected from atoms such as S and N, and may further comprise a substituent; R1 to R19 in the above structure may be the same or different, and Ri to Rl9 are independently selected from one of the following groups: a hydrogen atom, Halogen atom, aryl group, halogen-substituted aryl group, C1-C20 halo-substituted aryl group, arylalkyl group, aromatic alkenyl group, cl_c2〇 haloalkyl-substituted aryl group, aryl-substituted cl_C2 decane a C1-C20 alkyl group, a C1-C20% alkyl group, a C1-C20 alkoxy group, an amino group, an amine group substituted with an aryl group, and an amine substituted with a C1-C20 alkyl group. a nitroso group, a nitro group, a carbonyl group, a cyano group (-CN), a substituted aromatic amine group, a heterocyclic group, and a cyclic group Piperidine (morpholine). 2. The conjugated compound having a heteropolycyclic structure as described in claim 1, wherein the aryl group comprises one of the following groups: phenyl (phenyl), naphthalene Naphthyl, diphenyl, anthryl, pyrenyl, phenanthry 1 and benzophenone or other forms of polyphenyl ring substituents . 3. The conjugated compound having a heteropolycyclic structure as described in claim 1, wherein the above-mentioned heterozygous group comprises one of the following groups: pyrane, pyrroline , furan, benzofuran, thiophene, benzothiophene, pyridine, quinoline, isoquinoline, beta (pyrazine), pyrimidine, pyrrole, pyrazole, imidazole, 0 indole, thiazole, heterotrophic ( Isothiazole), oxazole, isoxazole, benzothiazole, benzoxazole, 1,2,4_tri-oxo (l,2 , 4-triazole), 1,2,3-triazole, 1,2,3,4-tetrahydropurine (1,2,3,4-tetraazole), and A phenanthroline having a heteropolycyclic structure as described in claim 1, wherein the above cycloalkenyl group comprises one of the following groups: cyclohexene, Hexadiene (cyclohexadiene), cyclopentene (cyclopentene) with cyclopentadiene (cyclopentadiene). 5. The conjugated compound having a heteropolycyclic structure as described in claim 1, wherein the general formula of the above conjugated compound having a heteropolycyclic structure is as follows: Page 47 of 58 201000484

其中’上述結構中的r1〜r21可以相同或不同，且r1〜r2i係獨立選自下列族群中之—者：氫原子、氧原子、i素原子、芳香基、鹵素取代的芳香基、Cl-C2〇鹵烷基取代的芳香基、芳香烷基、芳香烯基、Cl-C2〇 _烷基取代的芳香烷基、具芳香基取代的 C1-C20烷基；C1-C20烷基、C1-C20環烷基、Cl_C2〇烧氧基 (alkoxy group)、胺基（amino group)、具芳香基取代的胺基、具 C1-C20烷基取代的胺基、亞硝酸基(nitroso group)、硝基(nitro group)、羰基（。訂1301^1 group)、氰基（cyano group, -CN)、具有取代基的芳香胺基、雜環基團、具有環狀的胺基(piperidine， morpholine)。6.如申請專利範圍第1項所述之具有雜多環結構之共扼化合物’其中上述具有雜多環結構之共扼化合物之一般式如下：第48頁/共58頁 201000484Wherein r1 to r21 in the above structure may be the same or different, and r1 to r2i are independently selected from the group consisting of hydrogen atom, oxygen atom, i atom, aryl group, halogen-substituted aryl group, Cl-. C2〇 haloalkyl substituted aryl, arylalkyl, aromatic alkenyl, Cl-C2〇-alkyl substituted arylalkyl, aryl substituted C1-C20 alkyl; C1-C20 alkyl, C1- C20 cycloalkyl, Cl_C2 alkoxy group, amino group, amine group substituted with an aryl group, amine group substituted with C1-C20 alkyl group, nitroso group, nitrate Nitro group, carbonyl group (1301^1 group), cyano group (-CN), substituted aromatic amine group, heterocyclic group, cyclic amino group (pieperidine, morpholine) . 6. The conjugated compound having a heteropolycyclic structure as described in claim 1 wherein the general formula of the above conjugated compound having a heteropolycyclic structure is as follows: Page 48 of 58 201000484

立選自下列族群中之—者：氣原子、氧原子、南素原子、芳香基、齒素取代料f基、C1_基取代料麵、芳香炫基、芳香烯基、ci_C2G 基取代㈣找基、具芳香基取代的C1-C20烷基；C1-C20烷基、C1-C20環烷基、C1-C20烷氧基（alkoxygroup)、胺基（amin〇groUp)、具芳香基取代的胺基、具C1-C20烧基取代的胺基、亞琐酸基(nitroso group)、罐基(nitr〇 group)、徵基（carbonyl group)、氰基(cyano group，-CN)、具有取代基的芳香胺基、雜環基團、具有環狀的胺基(piperidine， morpholine) ° 7.如申請專利範圍第1項所述之具有雜多環結構之共軛化合物，其中上述具有雜多環結構之共軛化合物之一般式如下：第49頁/共58頁 201000484 R12It is selected from the following groups: gas atom, oxygen atom, south atom, aromatic group, dentate substitution material f group, C1_ group substituted material surface, aromatic syllabic group, aromatic alkenyl group, ci_C2G group substitution (4) a C1-C20 alkyl group substituted with an aryl group; a C1-C20 alkyl group, a C1-C20 cycloalkyl group, a C1-C20 alkoxy group, an amine group (amin〇groUp), an amine substituted amine a group, an amine group substituted with a C1-C20 alkyl group, a nitroso group, a nitr〇 group, a carbonyl group, a cyano group (-CN), a substituent The aryl compound having a heteropolycyclic structure as described in claim 1, wherein the above has a heteropolycyclic ring, and a cationic compound having a heterocyclic ring structure as described in claim 1 The general formula for the conjugated compound of the structure is as follows: Page 49 of 58 Page 201000484 R12

其中，上述結構中的ri〜r2。可以相同或不同，且r1〜r20係獨立選自下賴群中之-者：氫原子、自素料、芳香基、南素取代的芳香基、C1-C2G鹵烧基取代的芳香基、芳找基、芳香烯基、C1-C20鹵烷基取代的芳香烷基、具芳香基取代的cic2〇烷基，C1-C20烷基、C1-C20環烷基、C1_C2〇烷氧基（a〖koxy group)、胺基（amino group)、具芳香基取代的胺基、具clC2〇炫基取代的胺基、亞硝酸基(nitros〇groUp)、石肖基(nitr〇gr〇Up)、戣基（carbonyl group)、氰基（cyano group，_CN)、具有取代基的芳香胺基、雜環基團、具有環狀的胺基(piperidine，morpholine)、石黃胺基團（sulfonamide)、對甲苯石黃胺基團 (p-toluenesulfonamide)、苯石黃胺基團（benzenesulfonamide)、胺甲酸或乙酸酯（methyl or ethyl carbamate)。 8.如申請專利範圍第1項所述之具有雜多環結構之共軛化合物，其中上述具有雜多環結構之共軛化合物之一般式如下：第50頁/共58頁 201000484Among them, ri~r2 in the above structure. They may be the same or different, and r1 to r20 are independently selected from the group consisting of: a hydrogen atom, a self-sugar, an aromatic group, a south-substituted aromatic group, a C1-C2G halogen-substituted aromatic group, and an aromatic group. Find a base, an aromatic alkenyl group, a C1-C20 haloalkyl substituted arylalkyl group, an aromatic substituted cic2 alkyl group, a C1-C20 alkyl group, a C1-C20 cycloalkyl group, a C1_C2 nonyloxy group (a) Koxy group), an amino group, an amine group substituted with an aryl group, an amine group substituted with a clC2 fluorene group, a nitrosium groUp group, a nitr〇gr〇Up group, a fluorenyl group ( Carbonyl group), cyano group (_CN), substituted aromatic amine group, heterocyclic group, piperididine, morpholine, sulfonamide, p-toluene P-toluenesulfonamide, benzenesulfonamide, methyl or ethyl carbamate. 8. The conjugated compound having a heteropolycyclic structure as described in claim 1, wherein the general formula of the above conjugated compound having a heteropolycyclic structure is as follows: Page 50 of 58 201000484

立選自下列族群中之一者：氫原子、鹵素原子、芳香基、_素取代的方香基、C1-C20鹵炫基取代的芳香基、芳香烧基、芳香烯基、C1-C20鹵烧基取代的芳香烧基、具芳香基取代的C1-C20 炫基，C1-C20烧基、C1-C20環院基、C1-C20烧氧基（alkoxy group)、胺基（amino group)、具芳香基取代的胺基、具C1-C20 院基取代的胺基、亞确酸基(nitroso group)、确基(nitro group)、羰基（carbonyl group )、氰基(cyano group, -CN)、具有取代基的芳香胺基、雜環基團、具有環狀的胺基(piperidine，morpholine)、石黃胺基團（sulfonamide)、對甲苯石黃胺基團 (p-toluenesulfonamide)、笨績胺基團（benzenesulfonamide)、胺甲酸或乙酸醋（methyl or ethyl carbamate)。 9.如申請專利範圍第8項所述之具有雜多環結構之共軛化合物，其中上述之R37係選自下列群組中之一者：第51頁/共58頁 201000484One of the following groups: a hydrogen atom, a halogen atom, an aromatic group, a aryl substituted aryl group, a C1-C20 halo-substituted aryl group, an aromatic alkyl group, an aromatic alkenyl group, a C1-C20 halogen group Substituted aromatic alkyl, aryl-substituted C1-C20 succinyl, C1-C20 alkyl, C1-C20 ring, C1-C20 alkoxy group, amino group, aromatic a substituted amino group, an amine group substituted with a C1-C20 compound, a nitroso group, a nitro group, a carbonyl group, a cyano group (-CN), Aromatic amine group, heterocyclic group, piperidine, morpholine, sulfonamide, p-toluenesulfonamide, amide amino group Benzenesulfonamide, urethane or ethyl carbamate. 9. The conjugated compound having a heteropolycyclic structure as described in claim 8, wherein the above R37 is selected from one of the group consisting of: 51 of 58 pages 201000484

ο ^ >ο ^ >

10. 如申請專利範圍第1項所述之具有雜多環結構之共軛化合物，其中上述具有雜多環結構之共軛化合物係應用於有機電激發光元件與/或螢光元件中。 11. 如申請專利範圍第1項所述之具有雜多環結構之共軛化合物，其中上述具有雜多環結構之共輛化合物係應用於有機電子元件中的發光材料。 12. 如申請專利範圍第1項所述之具有雜多環結構之共軛化合物，其中上述具有雜多環結構之共軛化合物係應用於有機電子元件中的電洞傳導材料。 13.如申請專利範圍第1項所述之具有雜多環結構之共軛化合物，其中上述具有雜多環結構之共輛化合物係應用於有機電激發光元件中的主發光體材料（host material )。第52頁/共58頁 201000484 14. 一種有機發光元件，包含一對電極與至少一有機層位於該些電極之間’其中該至少一有機層包括一發光層，且該些有機層中至少有一層包含一具有雜多環結構之共軛化合物，該具有雜多環結構之共輥化合物之一般結構如下：10. The conjugated compound having a heteropolycyclic structure as described in claim 1, wherein the conjugated compound having a heteropolycyclic structure is used in an organic electroluminescent element and/or a fluorescent element. 11. The conjugated compound having a heteropolycyclic structure as described in claim 1, wherein the above-mentioned compound having a heteropolycyclic structure is applied to a luminescent material in an organic electronic component. 12. The conjugated compound having a heteropolycyclic structure as described in claim 1, wherein the conjugated compound having a heteropolycyclic structure is applied to a hole conducting material in an organic electronic component. 13. The conjugated compound having a heteropolycyclic structure according to claim 1, wherein the above-mentioned compound having a heteropolycyclic structure is applied to a host illuminant material in an organic electroluminescent device (host material) ). Page 52 of 58 201000484 14. An organic light-emitting element comprising a pair of electrodes and at least one organic layer between the electrodes, wherein the at least one organic layer comprises a light-emitting layer, and at least one of the organic layers One layer comprises a conjugated compound having a heteropolycyclic structure, and the general structure of the co-roller compound having a heteropolycyclic structure is as follows:

其中’ A係選自S、N等原子，A可以更包含一取代基。上述結構中的R1〜R19可以相同或不同，且R1〜R19係獨立選自下列族群中之一者：氫原子、鹵素原子（例如：氟、氣、溴、峨）；芳香基；鹵素取代的芳香基；C1-C20鹵烷基取代的芳香基；芳香烷基；芳香烯基：C1-C20鹵烷基取代的芳香烷基；具芳香基取代的C1-C20烷基；C1-C20烷基、CKC20環烷基（例如：甲基、乙基、丁基、環己基）；C1-C20炫氧基（alkoxy group);胺基 (amino group);具芳香基取代的胺基；具C1-C20烷基取代的胺基；亞石肖酸基(nitrile group);石肖基(nitro group);幾基（carbonyl group);氰基(cyano group, -CN);具有取代基的芳香胺基；雜第53頁/共58頁 201000484 J衣基團’具有J衣狀的胺基（piperidine，morph〇line)。 15. 如申請專利範圍第14項所述之有機發光元件，其中上述之芳香基包3下列族群中之一者：苯基(phenyl)、萘基(naphthyl)、聯笨基（diphenyl)、蒽基（anthryl)、苯并菲基（pyrenyl)、菲基 (phenanthryl)與二苯并五環（flu〇rene)或其他形式之多苯環取代基。 16. 如申請專利範圍第14項所述之有機發光元件，其中上述之雜環基團包含下列族群中之一者：U底喃（pyrane)、η辰洛琳(pyrr〇line)、 0夫喃（furan)、苯并 β夫喃（benzofuran)、嗟吩（thiophene)、苯并嘆吩（benzothiophene)、°比唆（pyridine)、啥琳（quinoline)、異啥琳 (isoquinoline)、η比嘻（pyrazine)、嘴 0定（pyrimidine)、〇比洛 (pyrrole)、。比唾（pyraz〇ie)、味。坐（imidazole)、11 弓卜朵（indole)、0塞 0坐（thiazole)、異 α塞 α坐（is〇thiazole)、°惡唾（oxazole)、異 °惡 0坐 (isoxazole)、苯并嗟o^(benzothiazole)、笨并。惡唾（benzoxazole)、 1，2,4-二 °惡唾（1,2,4-triazole)、1，2,3-三 α惡嗤（i，2,3-triazole)、 1，2,3,4-四〇惡唾（1，2,3,4々6的&2〇16)’與二氮菲（卩|1611&111;111>〇11116)，或其他形式之異核芳香環。 17. 如申請專利範圍第14項所述之有機發光元件，其中上述具有雜多環結構之共軛化合物之一般式如下：第54頁/共58頁 201000484Wherein 'A is selected from atoms such as S and N, and A may further comprise a substituent. R1 to R19 in the above structure may be the same or different, and R1 to R19 are independently selected from one of the following groups: a hydrogen atom, a halogen atom (e.g., fluorine, gas, bromine, hydrazine); an aryl group; a halogen-substituted one Aromatic group; C1-C20 haloalkyl-substituted aryl group; arylalkyl group; aromatic alkenyl group: C1-C20 haloalkyl-substituted arylalkyl group; aryl-substituted C1-C20 alkyl group; C1-C20 alkyl group , CKC20 cycloalkyl (eg methyl, ethyl, butyl, cyclohexyl); C1-C20 alkoxy group; amino group; amine group substituted with an aryl group; C20 alkyl-substituted amine group; nitrile group; nitro group; carbonyl group; cyano group (-CN); aromatic amine group having a substituent; Page 53 of 58 201000484 The J-cloth group has a piperidine (morph 〇 line). 15. The organic light-emitting device of claim 14, wherein the aromatic group 3 is one of the following groups: phenyl, naphthyl, diphenyl, fluorene Anthryl, pyrenyl, phenanthryl and dibenzopentarene or other forms of polyphenyl ring substituents. 16. The organic light-emitting device of claim 14, wherein the heterocyclic group comprises one of the following groups: pyrane, pyrr〇line, 0 Furan, benzofuran, thiophene, benzothiophene, pyridine, quinoline, isoquinoline, η ratio Pyrazine, pyrimidine, pyrrole, pyrrole. More than saliva (pyraz〇ie), taste. Imidazole, 11 indole, thiazole, is〇thiazole, oxazole, isoxazole, benzo嗟o^(benzothiazole), stupid. Benzoxazole, 1,2,4-di-, 1,2,4-triazole, 1,2,3-triazole, 1,2, 3,4-four abominous saliva (1,2,3,4々6 &2〇16)' with phenanthroline (卩|1611&111;111>〇11116), or other forms of heteronuclear aromatic ring. 17. The organic light-emitting device according to claim 14, wherein the general formula of the above conjugated compound having a heteropolycyclic structure is as follows: Page 54 of 58 201000484

立選自下列族群中之一者：氫原子、氧原子、鹵素原子、芳香基、鹵素取代的芳香基、C1-C20鹵烷基取代的芳香基、芳香烧基、芳香烯基、C1-C20鹵烷基取代的芳香烷基、具芳香基取代的C1-C20烷基；C1-C20烷基、C1-C20環烷基、C1-C20烧氧基（alkoxy group)、胺基（amino group)、具芳香基取代的胺基、具C1-C20烧基取代的胺基、亞硝*酸基(nitroso group)、硝基(nitro group)、羰基（carbonyl group)、氰基（cyano group, -CN)、具有取代基的方香胺基、雜環基團、具有環狀的胺基(piperidine， morpholine) ° 18.如申請專利範圍第14項所述之有機發光元件，其中上述具有雜多環結構之共輊化合物之一般式如下：第55頁/共58頁 201000484One of the following groups: hydrogen atom, oxygen atom, halogen atom, aryl group, halogen-substituted aryl group, C1-C20 haloalkyl-substituted aryl group, aromatic alkyl group, aromatic alkenyl group, C1-C20 Haloalkyl substituted arylalkyl, aryl substituted C1-C20 alkyl; C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkoxy group, amino group An aryl group-substituted amine group, a C1-C20 alkyl group-substituted amine group, a nitroso group, a nitro group, a carbonyl group, a cyano group, CN), a arylamino group having a substituent, a heterocyclic group, and a fluorocarbon having a ring-shaped amino group. The organic light-emitting element according to claim 14, wherein the above-mentioned heteropoly The general formula of the ruthenium compound of the ring structure is as follows: Page 55 of 58 page 201000484

立選自下列族群中之一者：氫原子、_素原子、芳香基、齒素取代的芳香基、C1-C20鹵烧基取代的芳香基、芳香烧基、芳香烯基、C1-C20鹵烷基取代的芳香烷基、具芳香基取代的cl_C2〇烧基；C1-C20烷基、C1-C20環烷基、C1-C20烷氧基（alk〇xy group)、胺基（amino group)、具芳香基取代的胺基、具cl_C2〇院基取代的胺基、亞硝酸基(nitroso group)、確基(nitro group)、羰基（carbonyl group )、氰基（cyano group, -CN)、具有取代基的 ^香胺基、雜環基團、具有環狀的胺基(piperidine，morpholine)、績胺基團（sulfonamide)、對曱苯石黃胺基團 (p-toluenesulfonamide)、笨石黃胺基團（benzenesulfonamide)、胺甲酸或乙酸西旨（methyl or ethyl carbamate)。 19.如申請專利範圍第18項所述之有機發光元件，其中上述具有雜多環結構之共軛化合物中之R37係選自下列群組中之一者：第56頁/共58頁 201000484One of the following groups: a hydrogen atom, a sulfonium atom, an aryl group, a dentate-substituted aryl group, a C1-C20 halogen group-substituted aryl group, an aromatic alkyl group, an aromatic alkenyl group, and a C1-C20 halogen group. Alkyl-substituted arylalkyl, aryl-substituted cl_C2 anthracenyl; C1-C20 alkyl, C1-C20 cycloalkyl, C1-C20 alkoxy (alk〇xy group), amino group An aryl group-substituted amine group, an amine group substituted with a cl_C2 oxime group, a nitroso group, a nitro group, a carbonyl group, a cyano group (-CN), a substituent having a substituent, a heterocyclic group, a cyclic amino group (piperidine), a sulfonamide, a p-toluenesulfonamide, a stupid stone Benzene sulfonamide, urethane or ethyl carbamate. 19. The organic light-emitting device according to claim 18, wherein the R37 of the above conjugated compound having a heteropolycyclic structure is selected from one of the group consisting of: 56 of 58 pages 201000484

Cl Cl--Cl 〇 W ;、^o 人;Cl Cl--Cl 〇 W ;, ^o person;

20.如申請專利範圍第14項所述之有機發光元件，其中上述具有雜多環結構之共軛化合物係應用於該有機發光元件的發光層。第57頁/共58頁The organic light-emitting device according to claim 14, wherein the conjugated compound having a heteropoly ring structure is applied to the light-emitting layer of the organic light-emitting element. Page 57 of 58