TW201111475A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents
Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDFInfo
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- TW201111475A TW201111475A TW099123922A TW99123922A TW201111475A TW 201111475 A TW201111475 A TW 201111475A TW 099123922 A TW099123922 A TW 099123922A TW 99123922 A TW99123922 A TW 99123922A TW 201111475 A TW201111475 A TW 201111475A
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- substituent
- compound
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- organic electroluminescent
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 117
- 125000001424 substituent group Chemical group 0.000 claims description 87
- 125000003118 aryl group Chemical group 0.000 claims description 61
- -1 amine compounds Chemical class 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 230000005684 electric field Effects 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 24
- 239000010410 layer Substances 0.000 claims description 20
- 239000012044 organic layer Substances 0.000 claims description 19
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
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- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 125000003367 polycyclic group Chemical group 0.000 claims description 10
- 125000002723 alicyclic group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 5
- 239000002019 doping agent Substances 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
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- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005264 aryl amine group Chemical group 0.000 claims description 2
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- 150000003431 steroids Chemical class 0.000 claims 1
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- 230000007704 transition Effects 0.000 claims 1
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- 238000004519 manufacturing process Methods 0.000 abstract description 6
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- 238000002360 preparation method Methods 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
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- 238000000605 extraction Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
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- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
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- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 3
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- PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 description 3
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- LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 description 3
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- GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 3
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
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Description
201111475 六、發明說明: 【發明所屬之技術領域】 本發明係關於新穎有機電場發光化合物及使用該化 合物之有機電場發光裝置,更特別地,本發明係關於用作 A t %發光材料之新穎有機電場發光化合物以及使用該化 合物作為主體(host)之有機電場發光裴置。 【先前技術】 就碟光發光材料的主體材料而言,CBP是目前為止最 廣為人知者。已報導使用電洞阻擋層(包含BCP與BAlq)之 具有高效率的0LED,以及使用BAlq衍生物作為主體之具 有高性能之0LED。 雖然這些材料提供良好的電場發光 Celectn)luminescence)之優勢’但是因為它們具有低玻璃 溫度以及非常差的熱安定性,因此缺點為於真空中之 尚溫沈積製程期間可能降解。由於0LED之功率效率(power efflcieney)錢義為(Π/電壓)x電流效率,因此功率效率 與,壓歧比。為了得到較低的咖之功率祕,則功率 1路*際上’使用鱗光發光材料的〇led比使用螢 m 1的_提供較高的電流致率(燭光/安培 == 而,當使用現行材料(例如叫⑽等)作為 ===主體時’就功率效率(流明/瓦(竭)而 5 u為其具有高驅動電壓(driv; 卜"亥0LED裝置並沒有令人滿意的操作壽命。因 94945 3 201111475 此,亟需發展出具有更安定及較高性能之主體材料。 【發明内容】 技術問題 為了克服上揭傳統技術之問題,本發明之發明人付出 極大努力,而發明了新穎有機電場發光化合物,其實現具 有優異的發光效率及顯著改善的壽命性質之有機電場發光 裝置。 本發明之目的係提供有機電場發光化合物,該化合物 具有提供較傳統主體材料或摻雜劑材料更佳之發光效率及 裝置壽命與適當色座標,同時克服上述問題。本發明之另 一目的係使用該有機電場發光化合物而提供一種高效率及 長壽命之有機電場發光裝置。 技術方案 本發明係提供以化學式1表示之有機電場發光化合 物,及使用該化合物之有機電場發光裝置。相較於現行主 體材料,由於本發明之有機電場發光化合物呈現良好發光 效率及優異壽命性質,因此其可用於製造具有極佳操作壽 命之0LED裝置。 [化學式1]
” vp 其中,環A及環B表示6員芳香環或6員雜芳香環; p及r表示0至2之整數,及q及s表示2至4之整 4 94945 201111475 數’限制條件為P+rM,p+q=4及r+s=4 ;
Ll及L2獨立地表不化學鍵、含有或不含有取代基之 (C6 C3〇)伸芳基、含有或不含有取代基之(C3-C30)伸雜芳 基、含有或不含有取代基之5員至7員伸雜環炫基、與一 個或多個含有或不含有取代基之芳香環稠合之5員至7員 伸雜環絲、含有或不含有取代基之⑹-⑽)伸環烧基、 與一個或多個含有或不含有取代基之芳香環稠合之 (C3 C30)伸環烷基、含有或不含有取代基之(C2_C3〇)伸烯 基、含有或不含有取代基之(C2_C3〇)伸炔基、含有或不含 有取代基之伸(C6-C30)芳基(C1-C30)烷基、-〇—或—S_ ;
An及An獨立地表示氫、鹵素、含有或不含有取代基 之(C1-C30)烷基、含有或不含有取代基之(C6_C3〇)芳基、 與—個或多個含有或不含有取代基之(C3-C30)環烷基稠合 之經取代或未經取代之(C6_C30)芳基、含有或不含.有取代 基之(C3-C30)雜芳基、含有或不含有取代基之5員至7員 雜環烷基、與一個或多個含有或不含有取代基之芳香環稠 δ之5員至7員雜環烧基、含有或不含有取代基之(c3_c3〇) 環烷基、含有或不含有取代基之與一個或多個芳香環稠合 之(C3-C30)環烷基、氰基、-NRllRl2、-SiRl3Rl4Rl5、-〇Rie、 含有或不含有取代基之(C6-C30)芳基(C1-C30)烷基、含有 戈不含有取代基之(C1-C30)烧基胺基、含有或不含有 一取代基2(C3_C30)雜芳基、含有或不含有取代 基之(C6-C30)芳基胺基、含有或不含有取代基之(C2_C3()) 稀基、含有或不含有取代基之(C2-C30)炔基、羧基、硝基、 5 94945 201111475
或經基’或Αιί及An可藉由含有或不含有稠合 環之(C3-C60)伸烷基或(C3-C30)伸烯基與相鄰取代基鍵 聯,以形成脂環、或單環或多環之芳香環;
Rn至RZg獨立地表示含有或不含有取代基之(c卜C3〇) 烷基、含有或不含有取代基之(C6-C3〇)芳基、或含有或不 含有取代基之(C3-C30)雜芳基,或心至—可藉由含有或 不含有稠合環之(C3-C30)伸烷基或(C3-C30)伸烯基與相鄰 取代基鍵聯,以形成脂環、或單環或多環之芳香環; X!至X8獨立地表示CL或N ;但排除其中X,至Χ8皆為 CRzi或皆為Ν之情況, Y 表示化學鍵、-(CR22R23)m-、_(r24)c=c(R25)_ -N(R26)-、-s-、—〇_或_Si(R27)(R28)_ ; R2i 至 ^係與 l 至 R2〇定義相同;以及 m表示1或2的整數; 該雜環院基或雜芳基可包括一個或多個選自N、〇 及S i之雜原子。 【實施方式】 在本發明中,、、烷基〃、、、烷氧基,,及其他包含、、烷基, 部分之取代基係包含直鏈及分枝鏈烷基兩者,且、、環烷 包含單環烴以及多環烴❹金職基或雙魏基。此處所 述術語m指經由自芳香烴去除—個氫原子後所得 之有機基。各環包括含有4至7個環原子(較佳為含有5 至6個環原子)之單環或稠合環系。亦包含經由化學鍵鍵聯 94945 6 201111475 一個或多個芳基之結構。該芳基之具體實例包含,但不限 於苯基、萘基、聯苯基、蒽基、茚基、第基、菲基、聯伸 三苯基(triphenylenyl)、芘基、茈基、蒯基(chrysenyl)、 稍四苯基(naphthacenyl)及丙二稀合荞基 (fluoranthenyl) ° 此處所述術語雜方基意指具有作為芳香環骨架原 子之選自N、0及8的i至4個雜原子’以及作為剩餘芳香 環骨架原子的碳原子之芳基。該雜芳基可為5員或6員單 環雜芳基或與一個或多個苯環稠合之多環雜芳基,且可為 部分飽和。此外,此處所述術語、、雜芳基"包含經由化學 鍵鍵聯一個或多個雜芳基之結構。 該雜芳基可包含二價芳基,該二價芳基雜原子經氧化 或四級化(quaternized)以形成N-氧化物(N_〇xide)及四 級鹽等。該雜芳基之具體實例包括,但不限於單環雜芳基 例如呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、 噻二唑基、異噻唑基、異噚唑基、噚唑基、噚二唑基、三 畊基、四I]井基、三唑基、四唑基、呋咕基(furazanyl)、吡 咬基、D比哄基、嘧啶基、嗒畊基;多環雜芳基例如苯并呋 喃基、苯并噻吩基、異苯并呋喃基、苯并咪唑基、苯并噻 唑基、苯并異嘆唑基、苯并異曙唾基、苯并嘻嗤基、異吲 σ朵基、吲哚基、吲唑基、笨并噻二唑基、喹琳基、異喹啉 基、噌啉基(cinn〇linyl)、喹唑啉基、喹哄基、喹噚啉基、 叶吐基、啡啶基及苯并二卩f呃基(benzodioxolyl);以及其 相應之氧化物(例如吡啶基N-氧化物、喹啉基N_氧化物) 7 94945 201111475 及其四級鹽。 此處所述、、(C1-C30)烷基〃可包含(C1-C20)烷基或 (C1-C10)烷基’且、、(C6-C30)芳基〃包含(C6-C20)芳基或 (C6-C12)芳基。'、(C3_C30)雜芳基〃包含(C3_C2〇)雜芳基或 (C3-C12)雜芳基’且、'(C3-C30)環烷基〃包含(C3-C20)環 烧基或(C3-C7)環烷基。、(C2-C30)烯基或炔基〃包含 (C2-C20)烯基或炔基、(C2-cl〇)烯基或炔基。 在 R"至 R2。、Li、L2、An、Ar2、及 R21 至 R28 之、、含有 或不含有取代基〃中,該取代基進一步可經獨立選自下列 之一個或多個取代基取代:氘、鹵素、含有或不含有鹵素 取代基之(C1-C30)烷基、(C6-C30)芳基、含有或不含有 (C6-C30)芳基取代基之(C3-C30)雜芳基、5至7員雜環燒 基、與一個或多個芳香環稠合之5至7員雜環烷基、(C3~C3〇> 環烧基、與一個或多個芳香環稠合之(C3_C3〇)環烷基、三 (C1-C30)烷基矽烷基、二(C1-C30)烷基(C6-C30)芳基矽烷 基、三(C6-C30)芳基矽烷基、(C2-C30)烯基、(C2-C30)炔 基、氰基、咔唑基、_NR3lR32、-SiR33R34R35、_〇R36、_张7、 (C6-C30)芳基(C1-C30)烷基、(C1-C30)烷基(C6-C30)芳 基、(C1-C30)烷氧基、(C1_C30)烷硫基、(C6-C30)芳氧基、 (C6-C30)芳硫基、羧基、硝基及羥基;或該取代基係鍵聯 至相鄰取代基以形成環。 R31至R37獨立地藉由含有或不含有稠合環之(C3-C30) 伸烧基或(C3-C30)伸稀基鍵聯至(C1-C30)烧基、(C6-C30) 芳基、(C3-C30)雜芳基或相鄰取代基,以形成脂環、或單 94945 201111475 工哀或多環之芳香環。
Rn至R28係選自,但不限於氫;鹵素;烷基例如甲美、 乙基、丙基、丁基、戊基、己基、乙基己基、庚基土 等;芳基例如苯基、萘基、第基、聯苯基、菲基、聯三: 基(terphenyl)、芘基、茈基、螺雙第基 — (spirobifluorenyl)、丙二烯合第基、蒯基、聯伸三笨美 等;與一個或多個環烷基掮合之芳基例如1>2_二氫苊基土 (l,2-dihydroacenaphthyl);雜芳基例如二笨并噻吩 二苯并呋喃基、咔唑基、吡啶基、呋喃基、噻吩基、喹啉 基、三畊基、嘧啶基、嗒哄基、喹噚啉基、啡啉基等;與 一個或多個芳香環稠合之雜環烷基例如^苯并吡咯啶基、 (benzopyrrolidino)、N-苯并六氫吡啶基 (benzopiperidino)、N-二笨基嗎啉基 (dibenzomorpholino)、N-二苯并氮呼(dibenzoazepino) 等;經芳基(例如苯基、萘基、荞基、聯苯基、菲基、聯三 苯基、芘基、茈基、螺雙第基、丙二烯合蕹基、蒯基、聯 伸二苯基等)或雜芳基(例如二苯并嗓吩基、二苯并Π夫喃 基、咔唑基、吡啶基、呋喃基、噻吩基、喹啉基、三畊基、 嘧啶基、嗒畊基、喹噚啉基、啡啉基等)取代之胺基;芳氧 基例如聯苯基氧基(biphenyloxy)等;芳硫基例如聯苯基硫 基(biphenylthio)等;芳烷基例如聯苯基甲基 (biphenylphenyl)、三苯基甲基等;缓基;硝基或羥基, 且可進一步如化學式1所示般經取代。 此外,本發明之有機電場發光化合物町由具有下列化 9 94945 201111475 學式2至5表示之結構之化合物例示,但不限於此。 化學式2
化學式4
其中,環A、環B、An、An、p、q、r及s係與化學 式1之定義相同,其中,各取代基可彼此不同。 本發明之有機電場發光化合物可由具有下列結構之 化合物例示,但不限於此。 10 94945 201111475 (*-2'Ar2) (L2Ar2) (L2-Ar2) {L2.Ar2> <L2-Ar2) jrNV^iM Ν^γΛ| {L2-Ar2> (L2.Ar2) fL2-Ar2) (L2Ar2)
Ji-2 ΑΓ2> m <La.Ar2> (L2_Ar2)
GO py2 Ar2> pc> pec::: (L1-Ar1)q(|_2.Ar2) fL^ArlJ«i(LzAr2) (Ll'Ar,)q iL^Ari)e,(L2Ar2) 其中’ Li、L2、An、An及q與如化學式1之定義相同 其中,各取代基可彼此不同。 本發明之An及An可如下列結構例示,但不限於此 11 94945 201111475
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本發明之有機電場發光化合物可由下列化合物具體 例示,但不限於此。 13 94945 201111475
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本發明提供一種有機電場發光裝置,其包含第一電 極;電二電極;以及插置於該第一電極與該第二電極間之 一層或多層有機層;其中,該有機層包含一種或多種以化 學式1表示之有機電場發光化合物。該有機電場發光化合 物係使用作為電場發光層之主體材料。 在有機電場發光裝置中,有機層包括含有一種或多種 以化學式1表示之有機電場發光化合物以及一種或多種磷 光摻雜劑之電場發光層。應用於有機電場發光裝置之電場 發光摻雜劑並未特別限制,但可如下列化學式6之化合物 例示。 化學式6 M1L101L102L103 Μ1係選自第7族、第8族、第9族、第10族、第11 17 94945 201111475 族、第13族、第14族、第15族及第16族組成群組之金 屬,而配位子(ligand) Lm、Li()2及Lm係獨立地選自下列 結構。
其中,R2G1至R2Q3獨立地表示氫、氘、含有或不含有鹵 18 94945 201111475 素取代基之(C1-C30)烷基、含有或不含有((^_C3〇)烷基取 代基之(C6-C30)芳基、或齒素;
Rm至R”9獨立地表示氫、氣、含有或不含有取代基之 (C卜C30)烷基、含有或不含有取代基之(C1_C30)烷氧基、 含有或不含有取代基之(C3-C30)環烷基、含有或不含有取 代基之(C2-C30)烯基、含有或不含有取代基之(C6_C30)芳 基、含有或不含有取代基之單或二(C1_C30)烷基胺基、含 有或不含有取代基之單或二(C6-C30)芳基胺基、SF5、含有 或不3有取代基之二(C1~C30)院基石夕烧基、含有或不含有 取代基之二(C1-C30)烷基(C6-C30)芳基矽烷基、含有或不 含有取代基之三(C6-C30)芳基矽烷基、氰基或齒素;
Rm至Km獨立地表示氫、氘、含有或不含有鹵素取代 基之(C1-C30)烷基、或含有或不含有(C1-C30)烷基取代基 之(C6-C30)芳基;
Rm及R225獨立地表示氫、氘、含有或不含有取代基之 (C1-C30)烷基、含有或不含有取代基之(C6-C30)芳基或鹵 素,或R224及Rm可藉由含有或不含有稠合環之(C3-C12) 伸烷基或(C3-C12)伸烯基相鍵聯,以形成脂環、或單環或 多環之芳香環;
Rm表示含有或不含有取代基之(Cl_C3〇)烷基、含有或 不含有取代基之(C6-C30)芳基、含有或不含有取代基之 (C5-C30)雜芳基或鹵素;
Rm至Rug獨立地表示氫、氖、含有或不含有取代基之 (C1-C30)烧基、(C6-C30)芳基或含有或不含有取代基之鹵 19 94945 201111475 素;
Rm及R23l獨立地表示氫、含有或不含有_素取代基之 (C1-C20)院基、(C6-C20)芳基、_ 素、氰基、三(ci-C2〇) 烷基矽烷基、二(C1-C20)烷基(C6-C20)芳基;ε夕烧基、三 (C6-C20)芳基矽烷基、(C卜C20)烷氧基、(C1-C20)烷基羰 基、(C6-C20)芳基羰基、二(C1-C20)烷基胺基或二(C6-C20) 芳基胺基,或R23。及R23丨可藉由含有或不含有稠合環之 (C3-C12)伸院基或(C3-C12)伸烯基相鍵聯,以形成脂環、 或單環或多環之芳香環; 藉由R23。及Rni之烧基、芳基或含有或不含有稠合環之 (C3-C12)伸炫基或(C3-C12)伸烯基鍵聯所形成之該脂環、 或該單環或多環之芳香環,可進一步經一個或多個選自下 述組成群組之取代基取代:含有或不含有函素取代基之 (C1-C20)烧基、_素、氰基、三(C1-C20)院基石夕烧基、二 (C1-C20)烷基(C6-C20)芳基矽烷基、三(C6-C20)芳基矽燒 基、(C1-C20)烷氧基、(C1-C20)烷基羰基、(C6-C20)芳基 羰基、二(C1-C20)烷基胺基、二(C6-C20)芳基胺基、笨基、 萘基、蒽基、第基或螺雙苐基;或可進一步經苯基或第基 取代,該苯基或第基係經一個或多個選自下述組成群紐之 取代基取代者:含有或不含有鹵素取代基之(C1-C20)烷 基、鹵素、氰基、三(C1-C20)烷基矽烷基、二(C1-C20)燒 基(C6-C20)芳基矽烷基、三(C6-C20)芳基砍烷基、(C1-C20) 烧氧基、(C1-C20)烷基羰基、(C6-C20)芳基羰基、二(C1〜C20) 烧基胺基、二(C6-C20)芳基胺基、苯基、萘基、蒽基、g 20 94945 201111475 基及螺雙第基; R232至R239獨立地表示氫、含有或不含有齒素取代基之 (U-C20)烷基、(C1-C20)烷氧基、(C3-C12)環烷基、齒素、 氰基、(C6-C20)芳基、(C4-C20)雜芳基、三(C1—C20)貌基 矽烷基、二(C1-C20)烷基(C6-C20)芳基矽烷基或三(cm:2〇) 芳基矽烷基; R2^LR242
Q 7Fλ R24«R2« λ D 一 246、或 R24eR棚,R241 至 R252 獨立 地表不氫、含有或不含有_素取代基之(c卜⑽)烧基、 (C1-C30)燒氧基、鹵素、 (C6-C60)方基、氰基、或(C5-C60) 裱烷基,或者r241至^ 2可稭由伸烷基或伸烯基鍵聯至相鄰 取代基,以形成(dr*?、, η )螺環或(C5-C9)稠合環;或r241至 (C5-C7)稠合環。埽基與相鍵聯以形成 M1係選自lr、pt、h ς d、Rh、Re、Os、ΤΙ、Pb、Bi、ιη、 ^ 厅紐成之群組,以及化學式6之化 合物包含韓國專利申譜 <化 ,. > 案第10-2009-0037519號中之實 例’但不限於此。 u 丁 <只 有機電場發光裴置 物,且同時包含-種或化學f1之有機電場發光化合 芳基胺化合物之化^夕種選自方基胺化合物及苯乙稀基 胺化合物包含,但^ °料基胺化合物及苯乙烯基芳基 1 η 限於韓國專利申請案第 10-2008〜0123276 號、坌, 八 ln 9nnQ Λ 第 10-2008-0107606 號及第 10-2008-01 18428 號中之每 〈貫例,但不限於此。 21 94945 201111475 有機層可復包含一種或多種選自下列所組成群組之 金屬:元素週期表第1族之有機金屬、第2族、第4週期 及第5週期之過渡金屬、鑭系金屬及d-過渡元素;或錯合 物化合物,以及化學式1之有機機電場發光化合物。該有 機層可同時包含電場發光層及電荷產生層。 本發明提供發出白光之有機電場發光裝置,其中,該 有機層包含一層或多層同時發出藍光、紅光或綠光之有機 電場發光層,以及有機電場發光化合物。 優勢效果 由於本發明之有機電場發光化合物係使用作為0LED 中之有機電場發光材料之主體材料5其與現存主體材料相 比具有好的發光效率及優異的壽命特性。據此,其可用於 製造具有極好操作壽命之0LED。 發明模式 為了易於了解,本發明係基於代表化合物而詳細說明 本發明之有機電場發光化合物、該化合物之製備方法以及 使用該化合物之裝置的發光性質。然而,下列實施例僅提 供作為例示說明用,而非意欲限制本發明之範疇。 [製備例1]化合物24之製備
化合物A之製備 22 94945 201111475 將2, 4-二氣喹唑啉(2公克(g),10. 0毫莫耳(mmol)) 溶解於DMF(2毫升(mL))後,於其内加入咔唑(3. 69g,22. 1 ramol)並於室溫攪拌混合物2小時。將水加入反應混合物而 完成反應。在以乙酸乙酯萃取及5%檸檬酸洗滌後,使用硫 酸納移除剩餘水分乾燥,且在經由管柱分離後,產生化合 物 A(2. 6g,7. 88mmol,79%)。 化合物24之製備 將咔唑(1. 97g,11. 8mmol)溶解於DMF及加入溶液(其 係將氫化鈉(605毫克(mg) ’ 15. 8mmol)溶解於DMF所獲得) 後,攪拌混合物1小時。於其内加入溶液(其係將化合物 A(2. 6g,7.88腿〇1)溶解於DMF所獲得),並於室溫下攪拌 24小時。當反應完成時,過濾所得固體。以乙酸乙酯萃取, 接著管柱分離產生化合物24(2g,4. 3訓1〇1,71%)。 [製備例2]化合物76之製锖
94945 23 201111475 化合物Β-l之製備 將2,4-二氣吡啶并[3,4-(1]嘧啶(5§,24.9111111〇1)、苯 基硼酸(3· 6g,29. 9mmol)、Pd(PPh3)4(l/15g,〇. 996mmol)、 碳酸納水溶液(87mL)、及乙醇(87mL)溶解於曱笨(i8〇mL) 後,混合物在120°C回流攪拌3小時。當反應完成時,有 機層以乙酸乙酯萃取,並使用硫酸鎮移除剩餘水分。乾燥, 接者官柱分離產生化合物B-l(4g,16. 5ιηιιια1,。 化合物B-2之製備 將咔唑(4g ’ 23. 9mmol)、1,4-二溴苯(14. ig , 59. 8mmol)、Pd2(dba)3(438mg,0. 478mmol)、三鄰曱苯基 膦(436mg,1.43mmol)及第三丁醇鈉(4.59g,47.8mmol)溶 解於曱苯(120mL)後’混合物在120 °C回流攪拌6小時。當 反應完成時’有機層以乙酸乙酯萃取,並使用硫酸鎂移除 剩餘水分。乾燥,接著管柱分離產生化合物B_2(4g, 12.4mmol , 65%)。 化合物B-3之製備 將化合物 B-2(4g,12. 4mmol)溶解於 THF(40mL)後, 冷卻混合物至-78t。10分鐘之後’將第三丁基鋰(2. 5]^於 己烧)(5. 95mL ’ 14. 88mmol)缓慢加入燒瓶内並擾拌混合物 1小時。將硼酸三甲酯(2. 35mL,18. 6mmol)緩慢加入燒瓶 内並攪拌混合物24小時。當反應完成時,於其内加入iM HC1。在以乙酸乙酯萃取及使用硫酸鎂移除剩餘水分後,在 乾燥’接著管柱分離產生化合物B-3(2g,6. 96 mmol,57%)。 化合物76之製備 94945 24 201111475 將化合物 β-2(1. 4g,5. 8mmol)、化合物 B-3(2g,6· 96 mmol)、Pd(PPh〇4(268mg,〇.232mmol)、碳酸鈉水溶液 (8mL)、及乙醇(8mL)溶解於甲苯(2〇mL)後,混合物在12〇 °C回流攪拌24小時。當反應完成時,有機層以乙酸乙酯萃 取,並使用硫酸鎂移除剩餘水分。乾燥,接著管柱分離產 生化合物 76(lg,2. 23mrool,40%)。 [製備例4]化合物89之製備
化合物C之製備 將2,3-二氫吡啶并[4,3-幻嘧啶-4(11〇(5.(^,33.5 mmol)溶解於氧氣化峨(5〇mL)後,混合物在1 〇〇°C回流授拌 5小時。當反應完成時,將反應物緩慢加入冰水内。以5M NaOH中和及過濾落下固體後,藉由管柱分離獲得化合物 C(2. 5g,15. Ommol,45%)。 化合物89之製備 將 4-氯吡啶并[4, 3-d]嘧啶(2. 5g,15. 0mmol)、3-(9H-咔唑-9-酮)聯苯基硼酸(8. lg,22. 5mmol)、Pd(PPh3)4(693 mg ’ 0. 60mmol)、碳酸納水溶液(52mL)、及乙醇(52mL)溶解 於甲笨(lOOmL)後,混合物在12(TC回流攪拌3小時。當反 應完成以乙酸乙酯萃取後,使用硫酸鎂移除剩餘水分。乾 燥’接著管柱分離產生化合物89(3g,6. 69 mmol,50%)。 94945 25 201111475 [製備例4]化合物108之製備
化合物D之製備 將嘧啶并[4, 5-d]嘧啶-4(8H)-酮(5. Og,33. 7mmol)溶 解於氧氣化磷(50mL)並在10(TC回流攪拌5小時。當反應 完成時’將反應物緩慢加入冰水内。以5M NaOH中和及過 濾落下固體後,藉由管柱分離獲得化合物D(2.2g, 13.2mmol , 40%)。 化合物108之製備 將 4-氯吡啶并[4, 3-d]嘧咬(2. 2g,13. 2mmol)、3-(9H-°卡。坐-9-酮)聯苯基棚酸(5. 6g ’ 19. 8mmol) ' pd(pph3)4(610 mg ’ 0. 52mmol)、碳酸鈉水溶液(46mL)、及乙醇(46mL)溶解 於曱苯(100mL)後,混合物在1201:回流攪拌3小時。當反 應完成以乙酸乙酯萃取後,使用硫酸鎂移除剩餘水分。乾 燥’接著管柱分離產生化合物l〇8(3.4g,9. 2mmol,70%)。 [製備例5]化合物128之製備
化合物E之製備 26 94945 201111475 將全氯吡啶并[5, 4-d]嘧啶(5g,18· 5mniol)、苯基硼 酸(4. 96g,40.7mmol)、Pd(PPh3)4(856mg,〇· 74mm〇i)、碳 酸鈉水溶液(65mL)'及乙醇(65mL)溶解於甲笨(2〇〇mL)後, 混合物在120°C回流授拌3小時。當反應完成以乙酸乙酯 萃取後,使用硫酸鎂移除剩餘水分。乾燥,接著管柱分離 產生化合物 E(5g,14. lmmol,77%)。 化合物128之製備 將化合物 E(5g,14. lmmol)及咔唑(5. 2g,31. lmmol) 溶解於二卩f烷(50mL)後,混合物在l〇〇°c回流攪拌1小時。 當反應完成以乙酸乙酯萃取後,使用硫酸鎂移除剩餘水 分。乾燥,接著管柱分離產生化合物128(7 g,16. 2mmol, 80%)。 [製備例6]化合物150之製備
_ _ -—-► Br-^^-TPS 一► 一^
化合物F-1之製備 將2,4-二氣喧。坐琳(15忌’75.36111111〇1)、4-聯笨基蝴酸 27 94945 201111475 (16. 4g,82. 89mmol)、Pci(PPh3)4(3. 76mmol)、2M-Na2C〇3(11〇 mL)及乙醇(50mL)溶解於甲苯(300mL)後,混合物在i〇〇t 回流攪拌3小時。當反應完成,混合物在室溫冷卻。以乙 酸乙酯萃取及以蒸餾水洗滌後,使用硫酸鎂移除剩餘水 分。乾燥,接著管柱分離產生化合物F-l(12g,37. 8δπιπκ3ΐ , 50. 26%)。 化合物F-2之製備 將1,4-一〉臭本(15g ’ 63. 58mmol)溶解於四氫。夫喃(3〇〇 mL) ’並在-78°C於其内緩慢加入正丁基鋰(26. 7mL,2. 5Μ 於己烷,66· 76mmol)。攪拌混合物1小時後,於其内加入 將三苯基氣矽烷(也1〇1»〇1;1^?1^1^15丨131^)(20.61111〇溶解 於四氫呋喃(70raL)之溶液,並在室溫攪拌12小時。反應完 成時,過濾移除所產生的白色固體,並以乙酸乙醋萃取遽 液。以蒸顧水洗務後,使用硫酸鎂移除剩餘水分,並在減 壓下進行蒸餾。以乙酸乙酯及曱醇再結晶而獲得化合物 F-2(17. 5g,42. 12mmo卜 66.25%)。 化合物F-3之製備
將化合物F-2(20g ’ 48. Ummol)溶解於四氫吱味(5〇〇 mL) ’並在-78 C於其内緩慢加入正丁基鐘(23 ,2 5M 於己烷’ 57. 5ιηιη〇1)。攪拌混合物1小時後,於其内加入硼 酸三曱酯(8. 5mL ’ 77. 03mmol) ’並在室温授拌12小時。以 乙酸乙醋卒取及以洛德水洗條後’以乙酸乙自旨及正己烧再 結晶而獲得化合物 F-3(14g,36. 81mmol,76 46%)。 化合物F-4之製備 94945 28 201111475 將 2-溴硝基苯(5g ’ 24. 75mm〇l)、化合物 ρ-3(1〇. 35 g ’ 27. 22mmol)、Pd(PPh3)4(l. 4g,1. 23mmol)、2M-K2C〇3(35 mL)、及乙醇(50mL)溶解於曱笨(lOOmL)後,混合物在i〇0 C回流授掉12小時。當反應完成時,使混合物在室溫冷 卻。以蒸鶴水洗綠及以乙酸乙i旨萃取有機層後,使用硫酸 鎂移除剩餘水分。乾燥,接著以乙酸乙酯及曱醇再結晶產 生化合物 F-4(llg,24. 03mmol,97. 12%)。 化合物F-5之製備 將化合物F-4(llg ’ 24. 03mmol)溶解於1,2-二氯苯 (10OmL)及於其内加入亞墻酸二乙酉旨(triethyl phosphite) (200mL)後’混合物在150°C授拌15小時。在減壓下蒸顧 後,將所產生的固體溶解於氯仿,經由矽石過濾而獲得化 合物 F-5(8g,18. 81 mmol,78. 40%)。 化合物150之製備 將化合物F-5(4. 8g ’ 11. 36 mmol)溶解於二曱基曱酿 胺(100mL)後’將混合物加入溶解有NaOH(0. 56g, 14. 20mmol)之DMF(25mL)溶液内。所得混合物在室溫攪拌} 小時。接著,於其内加入將化合物F-l(3g,9.47romol)溶 解於一曱基曱酿胺(5 0 inL)之溶液内’且混合物在室溫授拌 12小時。以蒸餾水洗滌及以乙酸乙酯萃取後,在減壓下進 行蒸餾。將產物溶解於氯仿並進行矽石過濾後,以曱醇、 乙酸乙酯及二曱基甲醯胺再結晶而獲得化合物 150(2. 8g,5· 46mmol,57. 68%)。 [製備例7 ]化合物154之製備 29 94945 201111475
化合物G-1之製備 將1,4-二溴笨(2〇g ’ 84. 78mmol)溶解於四氫呋喃(55〇 mL),並在-78t於其内緩慢加入正丁基鋰(37 3πα,2.5m 於己烷,93. 25mmol),攪拌混合物1小時。於其内加入將 曱基一笨基氣石夕院(diphenylmethylsi lylchloride) (21· 3mL)溶解於四氫呋喃(5〇mL)之溶液,並在室溫攪拌混 合物12小時。反應^成時以乙酸乙§旨萃取及以蒸館水洗務 後,使用硫酸鎂移除剩餘水分。乾燥,接著在減壓下進行 蒸餾。將產物溶解於氣仿後,經由矽石過濾而獲得化合$ G-l(16g , 45.28mmol , 53·9%)。 化合物G-2之製備 將化合物G-l(16g,45. 28mmol)溶解於四氫呋喃(2〇〇 mL)並在-78°C於其内緩慢加入正丁基鋰(21.7mL,2.⑽於 己烷,54. 34mmol)後,攪拌混合物1小時。於其内加入、 酸二甲酯(7. 57mL,67. 92mmol),並在室溫授拌u小日$ 以乙酸乙酯萃取及以蒸餾水洗滌後,以乙酸乙酯及正己浐 再結晶而獲得化合物G-2(12g,37. 70mmol,83.27%)。疋 94945 30 201111475 化合物G-3之製備 將 2 /臭硝基苯(7g,34. 65mmol)、化合物 G-2(12. 13g, 38. llmraol) > Pd(PPh3)4(2. 〇g » 1. 73mmol) ' 2M-K2CO3 (4〇mL)、及乙醇(5〇mL)溶解於甲苯(i2〇mL)後,混合物在 100 C回抓授拌12小時。當反應完成時,使混合物在室溫 冷卻。以瘵餾水洗滌及以乙酸乙酯萃取有機層後,使用硫 酸鎮移除剩餘水分。乾燥及在減壓下進行蒸德I,將所獲 得的化合物溶解於二氯甲烷並進行矽石過濾。在減壓下蒸 餾而獲待化合物 G-3(13g,32. 86mmol,94. 85%)。 化合物G-4之製備 將化合物G~3(13S,32. 86顏〇1)溶解於1,2-二氣苯 (150mL)及於其内加入亞磷酸三乙酯(2〇〇mL)後,混合物在 150 C授摔15小時。在減壓下蒸餾後,將所產生的固體溶 解於氯仿,並經由矽石過濾而獲得化合物G_4(1〇 5g, 28.88mmol , 87.80%)。 化合物154之製備 將化合物G-4(5. 〇4g,13. 88mmol)溶解於二甲基甲醯 胺(30mL)後,將混合物加入溶解有NaH(〇. % g,l8. 95随〇1) 之DMF(30mL)溶液内。所得混合物在室溫攪拌丨小時。於 其内加入將化合物F-l(4g,12. 62mmol)溶解於二甲基甲醯 胺(140mL)之溶液内後,混合物在室溫攪拌12小時。以蒸 餾水洗滌及以乙酸乙酯萃取後,在減壓下進行蒸餾。將產 物溶解於氣仿並進行矽石過濾後,以甲醇、乙酸乙酯及二 曱基甲酿胺再結晶而獲得化合物154(3. 6g,5 59mmol, 94945 31 201111475 44. 37%)= [製備例8 ]化合物15 6之製備
化合物H-1之製備 將 2-溴硝基苯(4〇g ’ 〇. i98mol)、1-萘硼酸(37. 46g, 0. 2Πιηο1)、Pd(PPh3)4 (6. 86g,〇. 005 mol)、2M-K2C〇3(200 mL)及乙醇(l〇〇mL)溶解於曱笨(3〇〇mL)後,混合物在1〇(rc 回流攪拌4小時。當反應完成時,使混合物在室溫冷卻。 以崧餾水洗滌及以乙酸乙酯萃取有機層後,使用硫酸鎂移 除剩餘水为。在乾燥及在減壓下進行蒸餾後,將所獲得的 化合物溶解於二氣甲燒並精料過it。在顧下蒸館而 獲得化合物 H-l(45g,〇. 180mol,91. 17%)。 化合物H-2之製備 將化合物H-l(45g,0. 180mol)溶解於ι,2-二氯苯(2〇〇 mL)並加入亞磷酸三乙酯(4〇〇mL)後,混合物在15〇c>c攪拌 12小時。混合物在室溫冷卻及在減壓下進行蒸餾後,經由 管柱分離而獲得化合物H—2(32g,〇. 147mol,81· 82%)。 94945 32 201111475 化合物H_3之製備 將 2, 4-二氯喹啉(15g,75. 7mmol)、Cul (28. 8g,151.4 mmol)、Cs2C〇3(73g,227· 2mmol)、反-1,2-二胺基環己燒 (2. 713mL,22. 72mmol)及 1’ 2-二氯苯(500mL)加入化合物 H-2(24. 6g ’ 113. 6mmol)後’混合物在 18(TC 回流攪拌 i2 小時。當反應完成時,使混合物在室溫冷卻。以蒸鑛水洗 滌及以乙酸乙酯萃取有機層後,使用硫酸鎂移除剩餘水 分。乾燥及在減壓下進行蒸餾後’經由管柱分離而獲得化 合物 H-3(20g,52. 79mmol,70. 38%)。 化合物H-4之製備 將化合物H-3(20g’ 52. 79mmol)、4-聯苯基爛酸(31 g, 158. 3mmol)、Pd(0Ac)2(l. 18g,5. 27mmol)、p(第三丁夷)3 (5. 2mL’ 50%於甲笨,l〇. 5mmol)及 K3P〇4(33. 6g,158. 3 mmol:) 加入1,4-二噚烷(6〇〇mL)中,且混合物在l〇(TC回流攪拌5 小時。當反應完成時,混合物在室溫冷卻。以蒸餾水洗滌 及以乙酸乙酯萃取有機層後,使用硫酸鎂移除剩餘水分。 乾燥及在減壓下進行蒸餾後,經由管柱分離而獲得化合物 H-4(15g , 30,20mmol , 57.21%)。 化合物H-5之製備 將化合物H-4(l〇g,20. 13mmol)溶解於四氫呋喃(3〇〇 mL)及在室溫於其内加入NBS(3· 94g,22. 15咖〇1)後,混合 物在室溫攪拌12小時。當反應完成時,混合物在室溫冷 卻。以蒸餾水洗滌及以乙酸乙酯萃取有機層後,使用硫7酸 鎂移除剩餘水分。乾燥及在減壓下進行蒸餾後,經由管柱 94945 33 201111475 層析分離而獲得化合物Η_5(9· 5g,16.50mro〇丨,82.53%)。 化合物156之製備 將化合物H-5(10g,17. 36mmol)溶解於四氫π夫喃(goo mL)並在-78°C於其内緩慢加入正丁基鋰(丨3. 89mL,2. 5Μ於 己烷,34· 73mmol)後,攪拌混合物1小時。將三笨基氣矽 烷(10. 2g)溶解於四氫呋喃(2〇〇mL)後,混合物在室溫攪拌 12小時。當反應完成時,於其内加入蒸顧水。以乙酸乙酯 萃取及以蒸餾水洗滌後,以硫酸鎂乾燥及在減壓下進行蒸 飽。經由管柱分離而獲得化合物156(5g,6. 62mmol, 38.丨4%)。 另外,以化合物2至5表示之不同的化合物可依據習 知組合方法藉由導入不同的取代基而以一種或多種選自下 列所組成群組者作為起始材料而化合:2, 4-二氣比咬并 [2, 3-d]°密咬(Ochem Incorporation)、2-氣比咬并[3, 2-d] 嘧啶(Anichem LLC)、吡啶并[4,3-d>g々-4(3H)-_(AceS Pharma,Inc. )、2_亂-6, 7-二曱基-〇棠口定(International Laboratory Limited)、2~氯喋啶(Princenton BioMolecular Research,lnc. )、3-氣喹啉(Texas Biochemical Inc. )、2, 4~二氣喹啉(Shanghai PI Chemicals Ltd)、2, 3-二氣喹啉(Aces Pharma, Inc. )、1-氣異喹啉(Alfa Aesar,China Ltd. )、1,3-二氯異喹啉 (Aalen Chemical Co. Ltd)、1,4-二氣異喹啉(Bepharm Ltd)。 根據製備例1至8製備有機電場發光化合物i至159, 34 94945 201111475 且所製得之有機電場發光化合物之NMR與MS/FAB數據 係顯示於表1 〇 35 94945 201111475 表1 化合物 αΗ NMR(CDC13/ 200 MHz) MS/FAB 實測值 計算值 1 δ = 7.25~7.33(3H, m) , 7.41(1H, m), 7.5~7.51(3H, m), 7.63(1H, m) , 7.79~7.8 (3H, m) , 7.94 (1H, m), 8.05~8.16(4H, m) , 8.55(1H, m) 371.43 371.14 2 δ = 7.25-7.33(3H, m) , 7.41(2H, m), 7.5~7.52(7H, m), 7.63(1H, m), 7.79(2H, m) , 7.94(1H, m), 8.02(1H, m), 8.12(2H, m), 8.45(1H, m), 8.55{1H, m) 447.53 447.17 3 δ = 7·25 〜7·33(3Η, m), 7.41(1H, π〇, 7.51(2H, m), 7.61C1H, m), 7.79〜7.8(3H, m) r 7.94(1H, m), 8·05~8.06(3Η, m), 8.16(1H, m), 8·55(1Η, m) 389.42 389.13 4 δ - 7.25{lHf m), 7.33-7.55(21H, m) , 7.69(lHf m), 7.77-7.8(4H, m) , 7.87-7.94(4H, m) , 8.05-8.06(2H, n〇 , 8·16(1Η, m> , 8.55(1H, m> 705.92 705.2^ 5 δ « 7.25(1H, m), 7.33-7.55(20H, m), 7.73-7.83(5H, m), 7.94(1H, m), 8.05-8.06(2Hr m) r 8·16(1Η, m), 8.55(1H, m) 629.82 629.23 6 δ = 1.35(9H, s), 7.25(lHr m) , 7.33(lfi, m) , 7.4K1H, m), 7.51 〜7·55(3Η, 7·62(1Η, 7.79〜7.8(3H, m), 7·94(1Η, m), 8.05~8,06(2H, m), 8.16(1H, m), 8·36(1Η, m), 8.55(1H, m) 427.54 427.20 7 δ = 7.4K3H, m) , 7.51~7.52 (10H, m), 7.69(1H, m), 7.77~7.8(5H, m), 7.87 (1H, m), 8~8.06(3H, m), 8.16~B.18(2H, m) 523.63 523.20 8 δ ® 1.92(4H, m), 3.44(4H, m)r 6.88-6.9(2¾^ m), 7.25(1H, m)f 7.33(1H, m), 7.41-7.51(4H, m), 7.79-7.8(3Hf m) , 7.94(1Ή, m), 8·05〜8·06(2H, m), 8.16(1H, m> , 8.55(1H, in) ' 440.54 440.20 9 δ « 7.4K1H, in), 7.51(2H, m) , 7.57(2H, m), 7.69(1H, m>, 7.77〜7.8(5H, m), 7·87(1Η, m), 8〜8.06(3H, m>, 8.16-8.18(2H, m), 8.42{2H, m)/ 8.7(2H/ m), 9.24(2H, m) 525.60 525.20 36 94945 201111475 10 δ «= 5.93UH, m), β.63(8Η, m) , 6.75-6.81 t6H, m), 7.2(8H, m), 7.38-7.41(2H, m), 7.51(2Hr m), 7.63(1H, m), 7.69(1H, m), 7.79-7.8(3H, m), 8.05-Θ.06(2H, m), 8.16(1H, m) 705.B5 705.29 11 δ = 7_25〜7·33(3Η, m), m), 7·5~7·51(3Η, m), 7_58〜7.68(4H, m), 7.79-7.84 (6H, m), 7.94(1H, m), 8.12-8.16(2H, m), 8.55(1Η, m) 447.53 447.17 12 δ - 7.25-7.33(3H, m), 7.41(1H, m) , 7.5-7.51(3Hr m), 7.58-7.63(2H/ m) f 7.79-7.88 (5H, in), 7.94-7.96 (2H, m), 8.12-8.16(2H, m) , 8.55-8.58(2H, m) 448.52 448.17 13 δ = 7.25-7.33(3Hf m) r 7.41(1H, m) r 7.5-7.51(3Hf m), 7.58-7.63(2H, m), 7.72<1H, m), 7.79-7.86(5H, m), 7.94(1H, m), 8·12~8.16(2Η, m), 8·38(1Η, m), 8·55<1Η, m) 448.52 448.17 14 δ = 7.25-7.33(3H, m), 7.4K1H, m) , 7.5-7.51{3H, m) f 7.58-7.63(2H, m), 7·79~7,84(4H, m), 7.94(1H, m), 8.12-Θ.16(2Η, m}, Θ.55(1Η, m) f 8.79(^, s), 8.82(^, s) 449.51 449.16 15 δ = 7.25-7.33(5H, m), 7.4K1H, m) 7 7.5-7.51(3H, m), 7.58-7.68{4H, m), 7.79-7.B5{8H, m), 7.94 (1H, m), 8·12〜8.16(2H, m), 8.55(1H, n〇 523.63 523.20 16 δ - 7.25-7.33(3H, τα), 7.41(1H, m), 7.48-7.51 {4H, m), 7.57-7.7(6H, m)# 7·79,7·84(6H, m), 7.94(1H, m), 8.12〜8·16(2Η, m), 8·24(1Η, m), 8·55(1Η, m) 523.63 523.20 17 δ = 1·96(6Η, s>, 5·83(2Η, irO, 7.25 〜·7.33(3Η, m), 7·5(1Η, m>, 7.63CLH, m), 7·8(1Η, m), 7·94(1Η, m), 8.05-8.16(4H, m), 8.55(1H, m) 388.46 388.17 18 δ = 2.69(12H, s)f 7.25-7.33(5Hr m) , 7.41(1H, m), 7.5-7.5K3H, m), 7.58-7.68 (4H, m) , 7.79-7.85 (8Hf m), 7.94(^, m), 8.12-8.16(2H, m), 8.55(lHf m) 655.83 655.30 19 δ « 2.5K3H, m), 7.22-7.33 (5H, m) , 7.5(1H, m) t 7·59〜7·63(2Η, m), 7.8(lfl, m), 7.94(1H, m), 8.05-8.16{4H, m), 8.55-8-56(2Hf m) 425.48 425.16 20 δ = 1.35(9H, s), 6.85(1H, m), 7.13(1H, s), 7.25-7.33(3H, m), 7.43(1H, m), 7.5(1H, m) , 7.63(1H, m), 7.72 (1H, m), 7.8(1H, ni), 7.93~7.94 (2H, m), 8.05~8.16(4H, m), 8.55(1H, m) 466.58 466.22 21 δ - 7.25-7.33(3H/ m) f 7.5-7.63(5H, m) , 7.7-7.8(3H, ra), 7.94-8.05(8H, m), 8.55{1H, m) . 504.60 504.14 22 δ = 6.95-7.01(3H, m), 7.25-7.33 (5H, m), 7.5(1H, m) f 7.63{1H/ m), 7.8(1H, m), 7.94(lfl, m) f 8.05-8.16(4H, cn) / 8.55 (1H, m) 387.43 387.14 23 . δ 7.25-.7.33 (3H, mj , 7.41~7.51 (12H, m), 7.58~7.63(3H, m), 7.79~7.8(3H, m), 7.94(1H, m), B.05~8.16(4H, m), 8.55{1H, m) 569.69 589.23 37 94945 201111475 24 δ « 7.25-7.33(6Η/ π〇, 7·5(2Η, m), 7.63{2Η, m), 7.8(1Η, m), 7.94(2Hf m), 8.05-8.16(5Η, m) t 8.55(2H, m) 460.53 460.17 25 δ = 3.83 (3H, m) , 7.25-7.33 (7H, m) , 7.5(2H, m), 7.63(2H, m), 7.74(1H, m) , 7.94~7.95(3H, m), 8.12(2H, tn) , 8.55 (2H, n) 490.55 490.IB 26 δ = 7.23〜7·39(8ΗΓ m)# 7.5(1H, m), 7.63(1H, m), 7.8{1H, m), 7.94UH, m), 8.05-8.16 (4H, m) f 9.55(1«, n〇 403.50 403.11 27 δ « 7.25(1H, m) , 7.33(1H, m), 7·41(1Η, m), 7.51-7.52(4H, m)t 7.63~7.67 (4H, m) , 7.8-7.85(3H/ m), 7.94(1H, m), 8.05-8.06(2H, m) , 8.16(2Hf m), 8.3(2H, m), 8.54-8.55(2H, m) 497.59 497,19 28 δ « 7.25(lHf m) , 7.33(1H, m) , 7.4-7.4K2H, ra), 7.51-7.55{3H, m), 7.67(2Hf m), 7.79-7.8(3H, mi, 7.94Ϊ1Η, m), 8.05-Θ.06(2H, m) , 8.16(3H, m), 8.55(1H, m) 421.49 421.16 29 δ = 7.25(1Η, m)f 7.33-7.41(3H, m) , 7.51(2H, m), 7.79-7.8(3H, m), 7.94(1H, m), 8.05-8.06(2H, m), θ.1β{1Η, m), 8.43(1H, m), 8.51-8.55 (2H, in) 372.42 372/14 . 30 δ = 7.25-7.37 (20H, m) , 7.61〜7.63(2H, ra), 7.76-7.8(2H, m)t 7.89-7.94 {2H, m) , 8.05-8.16(4H, m), 6.55(1H, m) 629.82 629.23 31 δ « 6.51(2H, m), 6.69(2H, m), 6.98~7.01(4H, m), 7.1K4H, m), 7.26(2H, m) , 7.33(4H, m) , 7.4K1H, m), 7.5K2H, m), 7.58(1H, m), 7.79^7.84 (4H, m) , 8.16(1H, m) 537.65 537.22 32 δ = 6.73(2H, m), 6.91(2H, m), 7.39-7.41(3H, m), 7.51-7.58(5H, m), 7.79-7.84 (4H, m), 8.16(1H, m) 399.44 399.14 33 δ « 6.59<2H, m), 6.77(2H, m), 6.89-6.92(4H, m), 7.41(1H, m), 7.51(2H, m) , 7.58(1H, m) , 7.79'7.84(4H, m) / 8.16(1H, m) 387.43 387.14 34 δ = 6.97(2H, m), 7.16-7.21 (6H, m) f 7.41(lHr m), 7.5K2H, m), 7.58C1H, m) , 7.79-7.84 (4H, m), 8.16(1H, m) 403.50 403.11 35 δ ® 6.38(4H, m) , 6.56(4H, m), 6.63(2H, m), 6.8K1H, m), 7.2(2H, m), 7.41(1H, m)-f 7.5K2H, m), 7.58(1H, m), 7.79-7.84(4H, m), Β.ΙβίΙΗ, m) 462.54 462.18 36 δ = 6·63(2Η, m), 6.81(2Hf m)f 6.99-7.05(4H, m), 7.25(2H, m), 7.41(1H, m), 7.51(2H, m), 7.58(1H, m>, 7.79-7.84(4H, m) , 8.16(lHr m) 397.47 397.16 37 δ » 7.25-7.33(3Hf m) , 7.41(lHf m), 7.5-7.52{5H, m), 7.G3(1H, m), 7.8-7.85{3H, m) r 7.94(1H, m), 8.05~8.16(4H, m), 8·3(2Η, m), 8.55(1H, m) 447.53 447.17 38 94945 201111475 38 δ = 7.14(1Η, m), 7.25-7.33(3Η, m), 7.5{1Η, m), 7.63(1Η, m), 7·7(1Η, m), 7.8UH, m), 7.88(1Η, ία), 7.94 (1Η, m), 8.05^8.16(4Η, m), 8.53-θ.55(2Η, m), 6.8K1H, πιϊΛ 8.99(lHf m), 9.3(1Η, m) 449.51 449.16 39 δ = 7.25-7.33(3Η, ία), 7.5-7.55(3Η, m), 7.61-7.63(2Η, m), ·7.8(1Η, π〇, 7·94 〜7·95(2Η, m), 8.0卜8.16<6Η, m), Θ.55(2Η, m) 421.49 421.16 40 δ = 7.25〜7·33(3Η, m), 7·42(1Η, m), 7.衫〜7.5(2Η, m), 7.63(1Η, m), 7.76〜7.8(2Η, m), 7.92-7.94(2Η, m), 8.05-8.16(4Η, m), 8.43(1Η, m) f 8.55(1Η, m), 8.87C1H, m) 422.48 422-15 41 δ = 7.25〜7.33(3Η,πι), 7·5(1Η, m), 7·63(1Η, m), 7.8〜7.94(7Η, m), 8.05-8.16(6Η, m), 8.55(1Η, m), 8.93(2Η, m) 471.55 471.17 42 δ = 7.25-7.33(3Η, m), 7.5(1Η, m), 7.58-7.65(4Η, m), 7.8(lHr m), 7.94(lHf m) , 8.05-8.16(4Η, m) , 8.38(2Hf m), 8.55(1H, m)f 8.83(2Hf m) 473.53 473.16 43 δ = 7.25~7.33(3H, m>, 7.5(1H, m), 7,63(1H, m), 7.8~7.88(5H, m), 7.94 (1H, m) , 8.04-8. IB(8H, m), 8·55(1Η, m), 8.93(2H, m), 9.15《1H, m) 521.61 521.19 44 δ * 2.34(3H, m), 7.25〜7.33(5H, m), 7.5(1H, m), 7.63-7.67{3H, ία), 7·8(1Η, m) , 7.94 (1H, m), 8.05〜8.16(4H,m),8.55(lH,m} 385.46 385.16 45 δ « 7.25-7.36{4H, m) , 7.5(1H, m), 7.63 (:LH, m), 7.8-7.85(2Hf m) , 7.94{1Η, m) f 8.05-6.16(4H, m)r 8.4(1H, m) r 8.55-8.59 [2H, in) 372.42 372.14 46 δ = 7.25-7.33(3H, m), 7.41(2Hf m), 7.5-7.51(5H, m), 7.57-7.63Ϊ2Η, m), 7.7〜7·8(7Η, m) , 7.94(1H, m), 8.05-8.16(4H, n〇, 8·23(1Η, s), 8·24(1Η, m), 8.55UH, m) 601.70 601.23 47 δ = 2.44(6H/ s), 7.25-7.33(3H, m), 7.5E1H, m), 7.63(lHf m), 7.8(lHf m), 7.94(lHf m) r 8.05-8.16(4Hf m), 8.55(1H/ m) 402.45 402.16 48 δ = 7.25~7.33(3H, m), 7.41(2H, m), 7,5~7.51(5H, m〉, 7·63(1Η, m), 7.8(1H, m), *7.94(1H, ir〇, 8·05〜8.16(4H, m), 8·2Θ(4Η, m>, 8.55(1H, m) 526.59 526.19 49 δ = 7.25-7.33(3H, m), 7.42-7.43(3H, m), 7.5~7.55(3H, m), 7.63(1H, m), 7.8(1H, m), 7.94(1H, m), 8.05~8.16(4H, m), 8.55(1H, m) 395.45 395.14 50 δ = 6.99(2H, ,m), 7.25-7.33{3Hf m) , 7.41(2H, m), 7.5〜7.51(5Hr m), 7·63(1Η, m>f 7.8(1H, m), 7·94(1Η, n) r S.05-8.16{4H/ m), 8.28(4H/ mjf 8.55(1H, m) 552.63 552.21 51 δ = 3.57(4H, m), 3.65K4H, m), 7.25-7.33 (3H, m), 7.5(1H, m), 7.63(1H, m), 7.8{1H, m), 7.94(1H, m), B.05~8.16(4H, m), 8.55(1H, m) 380.44 380.16 39 94945 201111475 52 δ - 7.25-7.37(9Η, m) , 7.46-7.55(12Η, m) , 7.63(1Η, m), 7.8-7.94(6Η, m) , 8.05-8.16 (4Η, m) , 8.3(2Η, ιη), Β.55(1Η, m) 705.92 705.26 53 δ « 7.25-7.37(10Η, m) , 7.46-7.55(10Η, m) , 7.63(1Η, πν) , 7.73 (1Η, m) , 7.Β~7.85(3Η/ πν) , 7.94 (1Η, τα) r 8·05〜Β.16(4Η, ία), 3·3(2Η, m), 8.55(1Η, ra) 711.95 711.22 54 δ - 6.63(4Η, m) , 6.81(2Η, m), 7.2-7.33{7Η, ία), 7.5(1Η, m), 7.63(1Η, m) , 7.8(1Η, ία), 7.94(1Η, m), 8.05-8.16(4Η/ m), 8.55(1Η, m) 462.54 462.18 55 δ = 7.25-7.33(6Η, m)> 7.41(2Η, m) , 7.5-7.51(6Η, m), 7.63(2Η, m), 7·79(4Η, m), 7.94(2Η, ml, 8.12(2Η, m), Β.34(1Η, s), 8.5Κ1Η, s) , 8.55(2Η# ιη) 612.72 612.23 56 δ = 3.83(2Hf s), 7.25~7.33(6Η, m), 7.46(1Η, s), 7.5(2Η, m), 7.63(3Η, m) , 7.63(0Η, s), 7.94(2Η, m), β.12(2Η, ra), 8.55(2Η, m) 520.58 520.19 57 δ « 6.95-7.0K3H, m), 7.25-7.33 (5Η, m) , 7.5(1Η, m), 7.58〜7.6Β【4Η, m), 7.79-7.84 (4Η, m), 7.94(1Η, m), 8.12-8.16(2Η, m), 8.55(1Η, m) 463.53 463.17 58 δ * 4.28(4Η/ m), 7.2-7.33(7Η, m)f 7.5-7.51(3Η, m), 7.63(2Η, m), 7.94(2Hf m) , 8.12(2Η, m) , 8.55(2Η, m) 518.56 5^18.17 59 δ 3,83ί3Η, m), 7.25-7.33 (7Η, m) / 7·5{2Η, m), 7,63(2Η, m), 7,74(ΙΗ, m), 7·94〜7·95(3Η, π〇 , 8.12(2Η, m) , 8.55 (2Η, ιη) 490.55 490.18 60 δ « 7.14-7.17 (3Η/ m), 7.25-7.33 (6Η, ιη) , 7.41-7.5(5Η, m) , 7·63(2Η, π〇, 7.89-7.94 (3Η, ία) , 8.02 (ΙΗ, m), 8.12{2Η, m), 8.55(2Η, m) 552.62 552.20 61 δ = 2.44 {3Η, m), 7.25-7.33 (3Η, τη), 7·5(1Η, m), 7·63(1Η, m), 7.8(1Η, 20, 7.94(1Η, 8,05〜8.16ί4Η, m) , 8.55(ΙΗ/ m) 309.36 309.13 62 δ = 3.Β3(3Η, s), 5.35(1Η, s), 7.25-7.33(3Η, m), 7.42(1Η, S), 7.5(1Η, m) , 7.57(1Η, s) , 7.63(1Η, m), 7.94(1Η, m), Θ.12(1Η, m) , 8.55(1Η, m), 9.36(1Η, s) 341.36 341.12 63 δ ® 5.35(1Η, s), 7·25 〜7.33(4Η, 7·5(1Η, π〇, 7.63(lHf m), 7.7{1Η, m) , 7.89-7.94(2R, m) , 8.12(1Η, m), 8·55(1Η, m>, 9·36(1Η, S) 311.34 311.11 64 δ 7·25~7·33(6Η, m), 7.S(2Η, m), 7.63(2Η, m), 7.94{2Η, m)r 8.12(2Η, m) , 8.32(1H/ m) , 8.55(2Hf m), 8·73(1Η, m), 9.16(1Η, m) · 505.53 505.15 65 δ 7.25-7.33(3Η/ m), 7·41〜7.51(6Η, m), 7.58-7.63(2Η, m), 7.79-7.84 (4Η, m)f 7.94(ΙΗ, m), 8.09-8.16(3H, m), 8.28(1H, m), 8.55(lHf m} 447.53 447.17 66 δ = 1.72(6H, s), 7.25-7.38(5Hr m) , 7.5-7.55(2H, m), 7.63(2H, m), 7.77-7.8(2H, m) , 7.87-7.94(3H, m), B.05~8.16MH, n〇, 8.55(1H, 487.59 487.20 40 94945 201111475 67 δ = 7.37-7.58(23Η, m), 7.72(2Η, ιη), 7.79-7.84 (9Η, m)f 8.16(2Hr m) 744.95 744.27 68 δ » 7.41<3Η, m), 7·51(6Η, m), 7·58(3Η, m), 7·66(3Η, m), 7.79-7.84(12Η, m), 8.160Η, ία) 690.79 690.25 69 δ = 7·25〜7·41(5Η, m), 7·5~7·51(3Η, m), 7·63{1Η, m), 7.79(2Η, m), 7.94{1Η, m), 8.12(1Η/ mj , 8.43(1Η, m), 8.51'8.55(2Η, m) 372.42 372.14 72 δ 7·25~7·36(7Η, m), 7·5(2Η, m), 7.63-7.68(6β, m), 7.79(4Η, m), 7.94(2Η, m), 8·12(2Η, m), 8.43(1Η, m), 8.51〜8·55(3Η, 613.71 613.23 75 δ *« 7.25-7.38 (7Hr m), 7.5(2Η, m) f 7.63[2Η, m), 7.94(2Η, m), 8.12(2Η, m) , 8.43(1H, m), 8.55(2fi, m) Γ 8.87{1Η, ία〉 461.52 461.16 76 δ = 7.25-7.41(5Η, m), 7.5-7.5K3H, m), 7.63-7.68 (3Hf m) , 7.79(4Η, m) , 7.94(1Η, m) , 8.12UH, ία) , 8.43(1Η, m), 8·55(1Η, m), 8.8*7(1Η, π〇 44B.52 448.17 79 δ » 1.35(9Η, s), 7.25-7.33(3Η, m)r 7.41C1H, m), 7.5~7·52(5Η, m), 7·63(1Η, m), 7.94UH, m), 8.12(1Η, m>, 8·55(1Η, m), 8·98(1Η, m), 9·24ί1Η, m) 428.53 428.20 85 δ = 2.34(12Η, s), 7.25-7.33(5Η, m), 7.5(1Η, m), '6〜7·67(5Η, m), 7·94(1Η, m), 8·12(1Η, m), 8.55(1Η, m), 8.79(1Η, m) , 8.95(1Η, m) 528.65 528.23 89 δ » 7,25〜7·33(3Η, m), 7.5〜7·51(2Η, m>, 7·63〜7·68(3Η, m) , 7.79-7.85{4Η7 m), 7.94(lHf m), 8·12(1Η, m), 8.312Η, m)r 8.43(1Η, m), Θ.55(ΧΗ, m) r 9.27(1Η, s), 9.51(1Η, m) 448.52 448.17 93 δ *= 3.83(6Hf β), 6.97(^, m) , 7.25-7.33 (3Hf m), 7.41〜7.51(6H,m), 7.62-7.63(2Η, m) , 7.76(1H, m) f 7.9~7.97(3H,m),8.12(lHrm),8.55(lH,m) 508.57 508.19 98 δ = 7.22-7.33Ϊ4Η, m), 7.5(1H, m) , 7.63(1H, m), 7.94-7.97(2Hr, m)# 8.12(1H, m) , 8.43(lHf m), 8.55{1H, mj, 8.87(1H, s〉 296.33 296.11 104 δ = 7.25{4H/ m), 7.29(5H, s), 7,29-7.33 {4H, m), 7.5(4H, in), 7.63(4Hf m), 7.94(4H, m), 8.12(4H/ m), 8.55{4H, m) 791.90 791.28 108 δ = 7.25~7.33(3H, m), 7.46-7.51(3H, m), 7.63(1H, m), 7.79(1H, m), 7.94{1H, m), 8.09~8.1¾(2H, m), 8.55(1B, m), 8.78(1H, m), 9.26(1H, m), 9.27{1H, s) 373.41 373.13 112 δ = 7.25~7.33(3H, m) , 7.41~7.51(6H, m) , 7.63(1H, m), 7.94(1H, m), 8.12(1H, m), 8.55(1H, m), 8.57(lfl, s) 441,41 441.12 115 5 = 7.25~7.33(3H, m), 7.5(1H, m), 7.63~7.68(3H, m), 7.79(2H, m), 7.94(1H, m), 8.12(1H, m), 8.5(1H, s), B.55(1H, m), 8.63(2H, m) 373·41 373.13 41 94945 201111475 121 δ = 1.53{4Η, m) , 1.59(2Η, m), 4.03 (4Η, m), 7.25-7.33(6Η, m), 7.41 (1Η, m) , 7 · .51 (4Η, πι), 7.63(2Η, in), 7.79(2Η, m) , 7.94(2Η, m) , 8.12ί2Η, πι), 8.55(2Η, m) 621.73 621.26 124 δ - 7.25(1Η, m), 7.33-7.37 (8Η, m) ,· 7.46(6Η, m), 7.55(3Η, m), 7.73(1Η, m) , 7.83(1Η, m) , 7.94(1Η, ία), 8·55(1Η, m), ‘8.63(2H, n〇, 8.87(1Η, s) 555.70 555.19 125 δ « 7.25-7·37(20Η, m), 7.61〜7·63(2Η, π〇, 7·76(1Η, ra), 7.89 〜7·94(2Η, m), 8.12(1Η, in), 8.55(1Η, m), 8.63(2Η, m) 631.80 631.22 126 δ - 7.25〜7.33(3H, m)Γ 7.41-7.51(6H, m) f 7.63-7.68(3H, m), 7.79(2H, m) , 7.94(1H, m) , 0.12(1H, m) , 8.55(1H, m), 8.63(2H, m) 449.51 449.16 130 δ « 7.25(2H, m), 7.33(2H, m)f 7.41-7.51(10H, m), 7.63-7.67(8H, m), 7.94(2H, m) , 8·16(2Η, m), 8.54-8.55(4H, m) 714.81 714.25 132 δ = 7.25C2H,. m), 7.33(2H, m) r 7.41-7.51 (12H, m), 7.94 (2fl, m), 8.43(2H, in), 8.55(2H, m) f 9.34 (2Hf m) 616.67 616.21 139 δ « 7.25-7.3.3 (3H, m) , 7.41 〜7 · 51 (17H, m), 7.58-7.63{5H, m) , 7.69(lHf m) r 7.77(2H, m), 7.87(1H, m) , 7.94~8(2H, m), 8.12(1H, m), 8.18 (1H, m), 8.55(1H, m) 766.89 7-66.28 141 δ - 7.37(3Hf m)r 7.57(3H, m), 7.69-7.75(6H, ra) # 7.94(3Hf m), 8.22(3H, m) 398,46 398.15 142 δ = 7.25-7.33(.7H, ra) , 7.41{1H, m), 7.5-7.52 (5H, m), 7.6〜7.63(2H, m), 7.68(1H, s), 7.78(1H, m), 7.94-7.98(2H, m), 8.06-8.12(2H, m) , 8.55(1«, m) 446.54 446.IB 144 δ = 1.35(3Hf s), 7.25-7.38 (7H, ra), 7.5(1H, m), 7.6'7.63(2H, m), 7.78(lH, n〇 , 7·9卜7·98(2H, m), 8.06〜8.12(2H, m), 8.42(1H, m), 8·55(1Η, m> 426.55 426.21 146 δ = 7.25~7.33{6H, m), 7.42(2H, m) , 7.49-7.5(3H, m), 7.63(3H, m), 7.92-7.94(3H, m) f 8.12(2H, m), B.55(2Hf m) 459.54 459.17 147 δ = 7.25-7.33(3H, m), 7.42(1H, m) , 7.49-7.5(2H, mj f 7.58~7.65(4H, m), 7.76(1H, m), 7‘92〜7·94(2H, m), 8.12(1H, m), 8.38(2H, m) , B.43HH, s), 8.55(1H, m), 8.83(2H, m) 472.54 472.17 148 δ » 7·25-7·37(20Η, m) , 7.61-7.63(2H, m), 7.76-7.8(2«, m)f 7.69-7.94(2H, m), 8V05-8.16(4Hf m), 8.55(1H, m) . 629.82 629.23 149 δ = 7.25(^, m)f 7.33-7.46(14H/ m), 7.55(3H, m), 7.61-7.67(5H, m), 7.76-7.8(2Hf m), 7.89-7.94{2H, m), 8.05-8.06(2H, m), Θ.16(2Η, m)f 8.54-8.55(2H, m) 679.88 679.24 150 δ = 7.25C1H, m), 7.28-7.41 (22H, m) , 7.68(1H, m), 7.8-7.85(3Hr m), 7.94(1H, m), 8.05*8.06(2H, m), 8.16(lHf m), 8.22(lHr m), 8.3(2H/ m), 8.55(1H, m) 705.92 705.26 151 δ = 7.25(1H, m) , 7.33(1H, m), 7·41(1Η, m), 573.68 573.22 42 94945 201111475
156 7*25 {4H, πι)~ *7 ·?c /1 ΰ :------— 754.99 754.28 π〇, *7·46〜7·55(18Η, \/^%^7.37<61 A 7·41(1Η' m), 7.98·>8.06(3Η, ml ο J;.6®(1H, s) r ^-^8-7.83(28, +:-r-—--^J^8〇6(1H, m), 8.54 (1H, m) 157 δ = 0.66(3H, m) 7 _ _Λ —___ L41(1H, m), 7.46«h ^ 7 m) ; 7·37(4Η, iu), s), 7.78(1H, m), 7 98Π,Η 7\51~Jtl3H, m) r 7.68(0H, m), 8.53-8.54(2H. m) (1H, m> * 8.06(1H, m), 8.16(1H, 692.92 ¢92.26 158 159 δ = 〇.66(3H, m), 7 287ΤίΓ 、 ----- 7.63~7.68(5H, m) , 7 β'Λ },7'37'7·55 (15H, m) (2H, m), m); e.(53:Bm.!;(?eH-〇5J'e-〇6(2H> ^ , 693.91 693.26 m), ra)]'3^ Λ)' 7·63-7.67(4Η, 8.3(2H, m), 8.54QH. J'° 8 6(3H, 8.16(2H, m), 693.91 693.26 [貝施例1至8]使用本發明之有機電場發光化合物之 0LED裝置之製造。 使用本發明之有機電場發光材料製造0LED裝置。首 先’使用超音波依序以三氯乙婦、丙酮、乙醇及蒸鶴水清 洗由0LED用之玻璃(samsung c〇rning製造)所得的透明電 極ΙΤ0薄膜(15Ω/〇) ’並儲存在異丙酮中備用。接著,將 ΙΤ0基板裝配於真空氣相沉積裝置之基板夾中,並將 4, 4 ,4 -參(Ν,Ν-(2-萘基)-苯基胺基)三苯胺(2_Τ·ΤΑ) 置於該真空氣相沉積裝置之一小室中,然後在腔室中通氣 以達10 6托(torr)真空。然後,對該小室施加電流以蒸發 2-TNATA,從而在ΙΤ0基板上形成厚度為6〇奈米(nm)的電 洞注入層。 94945 43 201111475 然後’將N,N,-雙(〇:-萘基)-N,N,-二笨基~4,4,〜 二胺(MPB)充填至該真空氣相沉積裝置之另一小室中,對該 小室施加電流以蒸發NPB,從而在該電洞注入層上形成厚 度為20奈米的電洞傳輸層。 如下述在該電洞傳輸層上形成電場發光層。將於1〇-6 托真空昇華之本發明之化合物(例如化合物52)作為主體 材料充填至真空氣相沉積裝置之一小室中,及將電場發光 摻雜劑(例如雙-(1-苯基異喹啉基)銥(m)乙醯丙酮酸酉旨 (piq)Jr(acac))充填至另一小室中。以不同速度蒸發這兩 個材料,從而以4至10莫耳%於該電洞傳輸層上形成厚度 為3〇nm之電場發光層。 然後’氣相沉積參(8-羥基喹啉)鋁(III)(Alq)作為厚 度為20nm之電子傳輸層,及氣相沉積8-羥基喹啉鋰 (lithium quinolate,Liq)作為厚度為1至2nm之電子注 入層。隨後’使用另一真空氣相沉積裝置,氣相沉積厚度 為I50nm之鋁(A1)陰極,從而製造0LED。 表2顯示根據實施例之驅動電壓(V)及發光效率(Cd/A) 之結果。 [比較例1]使用傳統電場發光材料之〇LED之製造 使用與實施例1相同方法製造0LED,除了將4, 4’ -二(9H-咔唑-9-酮)聯苯(CBP)取代本發明之有機電場發光 化合物於真空氣相沉積裝置之另一小室中作為電場發光材 料以及將雙(2-曱基-8-羥基喹啉基)(對苯基酚基)-鋁 CBis(2-raethyl-8-quinolinato)(p-phenylphenolato)- 44 94945 201111475 aluminum(III)BAlq)使用作為電子傳輸層。
在1,000燭光/平方米(cd/m2)下分別測量從包括本發 明之有機電場發光化合物(實施例1至5)或傳統EL化合物 (比較例1)所製得之OLED的驅動電壓及發光效率,且結果 顯示於表2。 表2 @l,000cd/m2 主體材料 發光材料 驅動 電壓 (V) 發光效率 (cd/A) 顏色 實施例 1 化合物 27 (piq)2lr(acac) 6.8 7.2 紅 實施例 2 化合物 37 (piq)2Ir(acac) 6.7 ΊΛ 紅 實施例 3 化合物 52 (Piq)2lr (acac) 7.0 7.7 紅 實施例 4 化合物 ΊΊ (piq) 2ΙΓ(acac)' 6.6 7.1 紅 實施例 5 化合物 143 (piq) 2lr (acac) 6.6 7.2 紅 實施例 6 化合物 153 (piq) zIt (acac) 6.8 7.6 紅 實施例 7 化合物 154 (piq) 2Ir (acac) 6.9 7.5 紅 實施例8 化合物 155 (piq) 2工r(acac) 6.6 7.4 紅 實施例 9 化合物 156 (piq)2Ir(acac) 6.9 7.8 紅 比較例 1 CBP (piq) 2lr (acac) 7.5 6.5 紅 如表2所示,與傳統材料相較,本發明之有機電場發 光化合物具有優異的發光效率。此外,使用本發明之有機 電場發光化合物作為用於發出紅光之有機電場發光裝置之 45 94945 201111475 主體材料具有優異的發光效率及下降的驅動電壓,因而降 低功率消耗。 【圖式簡單說明】 益 * "、 【主要元件符號說明】 益 φ 46 94945
Claims (1)
- 201111475 七、申請專利範圍: x 1表不之有機電場發光化合物: 1. 一種以化聲彳τ ± _ 丄,其中, 衣A及表示6員芳香環或6員雜芳香環; P及『表示〇12之整數,及表示2至’ 正,限制條件為 p+rgl,p+q=4& r+s=4 ; Ll及L2獨立地表示化學鍵、含有或不含有取 之(C6 C3Q)伸芳基、含有或不含有取代基之(C3~C30^ 伸雜芳基、含有或不含有取代基之5員至7貢伸雜環姨 基、與一個或多個含有或不含有取代基之芳香環稠合之 5員至7員伸雜環烷基、含有或不含有取代基之(C3^m 伸環烷基、與一個或多個含有或不含有取代基之芳香環 稠合之(C3-C30)伸環烧基、含有或不含有取代基之 (C2-C30)伸烯基、含有或不含有取代基之(C2_C3〇)伸炔 基、含有或不含有取代基之伸(C6-C30)芳基(C1-C30) 貌基、·~0_或-s_; An及An獨立地表示氫、鹵素、含有或不含有取 代基之(C1-C30)烧基、含有或不含有取代基之(C6-C30) 芳基、與一個或多個含有或不含有取代基之(C3-C3CO 環烷基稠合之經取代或未經取代之(C6-C30)芳基、含有 或不含有取代基之(C3_C30)雜芳基'含有或不含有取代 94945 47 201111475 基之5員至7員雜環烧基、與一個或多個含有或不含有 取代基之芳香環稠合之5員至7員雜環烷基、含有或不 含有取代基之(C3-C30)環烷基、與一個或多個含有或不 含有取代基之芳香環稠合之(C3-C30)環烷基、氰基、 -NR11R12、-SiRl3Rl4Rl5、-〇Rl6、-SRn、含有或不含有取代 基之(C6-C30)芳基(C1-C30)烷基、含有或不含有取代基 之(C1-C30)烧基胺基、含有或不含有取代基 之(C3-C30)雜芳基、含有或不含有取代基之(C6-C30) 芳基胺基、含有或不含有取代基之(C2-C30)烯基、含有 或不含有取代基之(C2-C30)炔基、羧基、硝基或羥基, 或An及An可藉由含有或不含有稍合環之(C3-C60)伸 烷基或(C3-C30)伸烯基與相鄰取代基鍵聯,以形成脂 環、或單環或多環之芳香環; Rn至R2。獨立地表示含有或不含有取代基之 (C1-C30)烷基、含有或不含有取代基之(C6-C30)芳基、 或含有或不含有取代基之(C3-C30)雜芳基,或Ru至R20 可藉由含有或不含有稠合環之(C3-C30)伸烧基或 (C3-C30)伸烯基與相鄰取代基鍵聯,以形成脂環、或單 環或多環之芳香環; 該雜環烷基及雜芳基可包括一個或多個選自N、 0、S及Si之雜原子。 2.如申請專利範圍第1項所述之有機電場發光化合物,其 中,在Ru至R2G、Li、L2、Αιί及An之 ''含有或不含有 取代基〃中,該取代基進一步經獨立選自下列之一個或 48 94945 201111475 多個取代基取代:氘、鹵素、含有或不人 之(C1-C3G)絲、(G6-G3G)芳基、含有δ有®素取代基 芳基取代基之⑽-C3G)雜芳基、5含有(C6-C3〇) 貝雜環烧基、與 =個或多個芳香環稠合之5至7員雜環烷基、(c3_c3〇) 環烷基、與一個或多個芳香環稠合之(C3_c3〇)環烷基、 二(C1-C30)烷基矽烷基、二(C1-C30)烷基(C6-C30)芳基 矽烷基、三(C6-C30)芳基矽烷基、(C2-C30)烯基、 (C2-C30)炔基、氰基、咔唑基一仰3必2、_siR33R34R35、 -〇Rh、-SR37、(C6-C30)芳基(C1-C30)烷基、(C1-C30) 烷基(C6-C30)芳基、(C1-C30)烷氧基、(C1-C30)烷硫 基、(C6-C30)芳氧基、(C6-C30)芳硫基、羧基、硝基及 羥基;或該取代基係鍵聯至相鄰取代基以形成環; 心至R37係藉由含有或不含有稠合環之(C3_C3〇)伸 燒基或(C3-C30)伸烯基鍵聯至(cl_C3〇)烷基、(C6_C3〇) 芳基、(C3-C30)雜芳基或相鄰取代基,以形成脂環、或 單環或多環之芳香環。 3. 如申请專利範圍第1項所述之有機電場發光化合物,其 係以化學式2至5表示: [化學式2]49 94945 201111475 [化學式3][化學式4][化學式5] ί B T^C-2*Ar2)g C|V (Li-Ar^q 其中, 環A、環B、Αιί、An、p、q、r及s係與申請專利 範圍第1項所述之定義相同,其中,各取代基彼此不同。 4.如申請專利範圍第1項所述之有機電場發光化合物,其 係選自下列化合物者: 50 94945 201111475 (L2Ar2) (1»2·Αγ2) 、(L2-Ar2) (L2Ar2) (L2-Ar2) (L2-Ar2) 5^>1人(1_2為> 、(L2Ar2) (Lz'Ara) (L-VAr,), (L2Ar2) (L2Ar2) (L2Ai '{Lz Ar2WS;);N^iL2-Ar^^);r (L2,Ar2) (La-Ar2) 0-2-Ars>‘豕'珍_ b、L2、An、Ar2& q係與申請專利範圍第1項所 述之定義相同,其中,各取代基彼此為不同。 5·如申凊專利範圍第4項所述之有機電場發光化合物,其 中,An及An係選自下列結構者:94945 51 2011114756. —種有機電場發光裝置’包括如申請專利範圍第1至5 項中任一項所述之有機電場發光化合物。 7. 如申請專利範圍第6項所述之有機電場發光裝置,其係 52 94945 201111475 包含第—電極;第二電極;以及插置於該第一電極與該 第二電極間之一層或多層有機層;其中,該有機層包括 一種或多種如申請專利範圍第丨至5項任一項所述之有 機電場發光化合物以及一種或多種磷光摻雜劑。 8. 如申凊專利範圍第7項所述之有機電場發光裝置,其 中’該有機層復包括一種或多種選自芳基胺化合物及苯 乙烯基芳基胺化合物所組成群組之胺化合物,或一種或 多種選自下列所組成群組之金屬:第丨族之有機金屬、 第2族、第4週期及第5週期之過渡金屬、鑭系金屬及 過渡元素;或錯合物化合物。 9. 如申請專利範圍第7項所述之有機電場發光裝置,其 中,該有機層包括電場發光層及電荷產生層。 1〇.如申請專利範圍第7項所述之有機電場發光裝置,其係 發出白光之有機電場發光裝置’其中,該有機層包括一 層或多層同時發出藍光、紅光或綠光之有機電場發光 層。 53 94945 201111475 四、指定代表圖:本案無圖式 (一) 本案指定代表圖為:第()圖。 (二) 本代表圖之元件符號簡單說明: 五、本案若有化學式時,請揭示最能顯示發明特徵的化學式: [化學式1]2 94945
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WO2008047589A1 (en) * | 2006-10-06 | 2008-04-24 | Semiconductor Energy Laboratory Co., Ltd. | Quinoxaline derivative, and light-emitting element and light-emitting device using quinoxaline derivative |
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JP4819181B2 (ja) * | 2008-05-08 | 2011-11-24 | 新日鐵化学株式会社 | 有機電界発光素子用化合物及び有機電界発光素子 |
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- 2010-07-21 TW TW099123922A patent/TW201111475A/zh unknown
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KR20110013220A (ko) | 2011-02-09 |
KR101530583B1 (ko) | 2015-06-23 |
KR20140092795A (ko) | 2014-07-24 |
CN102625806A (zh) | 2012-08-01 |
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