TW202035416A - 化合物、有機光電二極體以及顯示裝置 - Google Patents
化合物、有機光電二極體以及顯示裝置 Download PDFInfo
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- TW202035416A TW202035416A TW109102768A TW109102768A TW202035416A TW 202035416 A TW202035416 A TW 202035416A TW 109102768 A TW109102768 A TW 109102768A TW 109102768 A TW109102768 A TW 109102768A TW 202035416 A TW202035416 A TW 202035416A
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- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
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- 125000002950 monocyclic group Chemical group 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000005882 oxadiazolinyl group Chemical group 0.000 description 1
- 125000005968 oxazolinyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical group CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphenyl group Chemical group C1=CC=CC2=CC3=CC=C4C=C5C=CC=CC5=CC4=C3C=C12 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
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- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 150000003549 thiazolines Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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Abstract
本申請案是關於一種由化學式1表示的化合物、一種有機光電二極體以及一種顯示裝置。
Description
本申請案主張2019年1月25日在韓國智慧財產局申請的韓國專利申請案第10-2019-0009760號的優先權及權益,所述申請案的全部內容以引用的方式併入本文中。
本申請案是關於一種化合物、一種有機光電二極體以及一種顯示裝置。
有機光電二極體是能夠進行電能與光能互轉換的裝置。
有機光電二極體可取決於操作原理分為兩類。一類為光電二極體,其中藉由光能形成的激子分離成電子及電洞且在電子及電洞各自轉移至不同電極時產生電能,且另一類為發光二極體,其藉由供應電壓或電流至電極來自電能產生光能。
有機光電二極體的實例可包括有機光電二極體、有機發光二極體、有機太陽能電池、有機光導鼓以及類似物。
其中,有機發光二極體(organic light emitting diode;OLED)近年來已隨著平板顯示裝置的需求增大而受到廣泛關注。有機發光二極體是將電能轉換為光的裝置,且有機發光二極體的性能極大地受安置於電極之間的有機材料影響。
有機發光二極體具有在兩個電極之間安置有機薄膜的結構。當將電壓施加至具有此類結構的有機發光二極體時,自兩個電極注入的電子及電洞在有機薄膜中結合及配對,且在所述電子及所述電洞湮滅時發光。視需要,可形成單層或多層有機薄膜。
有機薄膜的材料可視需要具有發光功能。舉例而言,可單獨使用能夠形成發光層本身的化合物作為有機薄膜的材料,或亦可使用能夠起主體-摻雜劑類(host-dopant-based)發光層的主體或摻雜劑作用的化合物作為有機薄膜的材料。
另外,亦可使用能夠起電洞注入、電洞轉移、電子阻擋、電洞阻擋、電子轉移、電子注入以及類似物作用的化合物作為有機薄膜的材料。
為提高有機發光二極體的性能、使用壽命或效率,需要持續地研發有機薄膜材料。
[技術問題]
本說明書的一個實施例是關於提供一種能夠獲得具有高效率及長使用壽命的有機光電二極體的化合物。
本說明書的另一實施例是關於提供一種包括所述化合物的有機光電二極體。
本說明書的又一實施例是關於提供一種包括所述有機光電二極體的顯示裝置。
[技術解決方案]
在化學式1中,
X1
及X2
中的至少一者為-N-,另一者為-CA-,Y為-S-或-O-,A以及R1
至R8
各自獨立地為氫、氘、氰基、經取代或未經取代的C1至C60烷基或經取代或未經取代的C6至C60芳基,且A以及R1
至R4
中的任一者由以下化學式2表示,
[化學式2]
在化學式2中,
Ar1
及Ar2
各自獨立地為經取代或未經取代的C6至C60芳基或經取代或未經取代的C2至C60雜芳基,X3
至X7
中的至少一者為-N-,X3
至X7
中的一者為-(L1
)n1
-Ar1
,X3
至X7
中的一者為-Ar2
-且其餘為-N-、-CH-或-CR-中的一者,L1
及L2
各自獨立地為單鍵、經取代或未經取代的C6至C60伸芳基或經取代或未經取代的C2至C60伸雜芳基,n1及n2各自獨立地為0至2的整數中的一者,R為氘、-CN、經取代或未經取代的C1至C60直鏈或分支鏈烷基、經取代或未經取代的C6至C60單環或多環芳基或經取代或未經取代的C2至C60單環或多環雜芳基,且當化學式1的A由化學式2表示時,化學式2的Ar1
及Ar2
中的至少任一者為經取代或未經取代的C2至C60雜芳基或經取代或未經取代的C6至C60稠環芳基,且*為鍵結位置。
本說明書的另一實施例提供一種有機光電二極體,所述有機光電二極體包括彼此面對的陽極及陰極以及安置於陽極與陰極之間的至少一個有機層,其中有機層包括所述化合物。
本說明書的又一實施例提供一種顯示裝置,所述顯示裝置包括有機光電二極體。
[有利效應]
可獲得具有高效率及長使用壽命的有機光電二極體。
下文中,將詳細描述本揭露內容的實施例。然而,此等實施例僅出於說明性目的,且本揭露內容不限於此且僅由稍後描述的申請專利範圍的類別定義。
在本說明書中,「經取代或未經取代」意謂:經由下述者所組成之群組中選出的一或多個取代基取代:氘、鹵基、-CN、C1至C60直鏈或分支鏈烷基、C2至C60直鏈或分支鏈烯基、C2至C60直鏈或分支鏈炔基、C3至C60單環或多環環烷基、C2至C60單環或多環雜環烷基、C6至C60單環或多環芳基、C2至C60單環或多環雜芳基、-SiRR'R"、-P(=O)RR'、C1至C20烷基胺基、C6至C60單環或多環芳基胺基、C2至C60單環或多環雜芳基胺基、經取代或未經取代的烷氧基、經取代或未經取代的芳氧基、經取代或未經取代的雜芳氧基、經取代或未經取代的芳基硫醇基、經取代或未經取代的烷基硫氧基、經取代或未經取代的芳基硫氧基、經取代或未經取代的烯基、經取代或未經取代的硼基、經取代或未經取代的矽烷基、經取代或未經取代的芳基膦基、經取代或未經取代的氧化膦基、經取代或未經取代的芴基以及包括N、O以及S原子中的一或多者的經取代或未經取代的芳族或脂族雜環基,或未經取代;或經使所述取代基中的兩者或大於兩者鍵結的取代基取代,或未經取代;或經使由上述取代基中選出的兩個或大於兩個取代基鍵聯的取代基取代,或未經取代。另外,此等基團可進一步與相鄰取代基形成環。
舉例而言,「使兩個或大於兩個取代基鍵聯的取代基」可包括聯苯基。換言之,聯苯基可為芳基,或解釋為使兩個苯基鍵聯的取代基。額外取代基可進一步經取代。R、R'以及R"彼此相同或不同,且各自獨立地為氫、氘、-CN、經取代或未經取代的C1至C60直鏈或分支鏈烷基、經取代或未經取代的C3至C60單環或多環環烷基、經取代或未經取代的C6至C60單環或多環芳基或經取代或未經取代的C2至C60單環或多環雜芳基。
根據本申請案的一個實施例,「經取代或未經取代」意謂經由下述者所組成之群組中選出的一或多個取代基取代或未經取代:氘、鹵基、-CN、-SiRR'R"、-P(=O)RR'、C1至C20直鏈或分支鏈烷基、C6至C60單環或多環芳基以及C2至C60單環或多環雜芳基,且R、R'以及R"彼此相同或不同且各自獨立地為:氫;氘;-CN;未經取代或經氘、鹵基、-CN、C1至C20烷基、C6至C60芳基以及C2至C60雜芳基取代的C1至C60烷基;未經取代或經氘、鹵素、-CN、C1至C20烷基、C6至C60芳基以及C2至C60雜芳基取代的C3至C60環烷基;未經取代或經氘、鹵素、-CN、C1至C20烷基、C6至C60芳基以及C2至C60雜芳基取代的C6至C60芳基;或未經取代或經氘、鹵素、-CN、C1至C20烷基、C6至C60芳基以及C2至C60雜芳基取代的C2至C60雜芳基。
術語「取代」意謂鍵結至化合物的碳原子的氫原子變成另一取代基,且只要取代位置為氫原子經取代的位置,亦即取代基可取代的位置,則取代的位置不受限制,且在兩個或大於兩個取代基取代時,所述兩個或大於兩個取代基可彼此相同或不同。
在本說明書中,鹵素可包括氟、氯、溴或碘。
在本說明書中,烷基包括C1至C60直鏈或分支鏈,且可進一步經其他取代基取代。烷基的碳原子數可為1至60,特定言之1至40,特定言之1至20且更特定言之1至10。其特定實例可包括(但不限於)甲基、乙基、丙基、正丙基、異丙基、丁基、正丁基、異丁基、第三丁基、第二丁基、1-甲基-丁基、1-乙基-丁基、戊基、正戊基、異戊基、新戊基、第三戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、庚基、正庚基、1-甲基己基、環戊基甲基、環己基甲基、辛基、正辛基、第三辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、1-乙基-丙基、1,1-二甲基-丙基、異己基、2-甲基戊基、4-甲基己基、5-甲基己基以及類似基團。
在本說明書中,烯基包括C2至C60直鏈或分支鏈,且可進一步經其他取代基取代。烯基的碳原子數可為2至60,特定言之2至40且更特定言之2至20。其特定實例可包括(但不限於)乙烯基、1-丙烯基、異丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-戊烯基、2-戊烯基、3-戊烯基、3-甲基-1-丁烯基、1,3-丁二烯基、烯丙基、1-苯基乙烯基-1-基、2-苯基乙烯基-1-基、2,2-二苯基乙烯基-1-基、2-苯基-2-(萘基-1-基)乙烯基-1-基、2,2-雙(二苯基-1-基)乙烯基-1-基、芪基、苯乙烯基以及類似基團。
在本說明書中,炔基包括C2至C60直鏈或分支鏈,且可進一步經其他取代基取代。炔基的碳原子數可為2至60,特定言之2至40且更特定言之2至20。
在本說明書中,環烷基包括C3至C60單環或多環,且可進一步經其他取代基取代。本文中,多環意謂其中環烷基直接鍵聯至另一環狀基團或與另一環狀基團稠合的基團。本文中,另一環狀基團可為環烷基,但亦可包括其他類型的環狀基團,例如雜環烷基、芳基以及雜芳基。環烷基的碳原子數可為3至60,特定言之3至40且更特定言之5至20。其特定實例可包括(但不限於)環丙基、環丁基、環戊基、3-甲基環戊基、2,3-二甲基環戊基、環己基、3-甲基環己基、4-甲基環己基、2,3-二甲基環己基、3,4,5-三甲基環己基、4-第三丁基環己基、環庚基、環辛基以及類似基團。
在本說明書中,烷氧基可包括C1至C10烷氧基,且更特定言之甲氧基、乙氧基、丙氧基、丁氧基、戊氧基以及類似基團。
在本說明書中,矽烷基可由-SiRR'R"表示,且R、R'以及R"具有與上述相同的定義。更特定言之,可包含二甲基矽烷基、二乙基矽烷基、甲基乙基矽烷基以及類似基團。
在本說明書中,氧化膦基可由-P(=O)RR'表示,且R及R'具有與上述相同的定義。更特定言之,可包含二甲基膦基、二乙基膦基、甲基乙基膦基以及類似基團。
在本說明書中,芴基意謂在數目9位置處包括各種取代基的取代基。特定言之,可使用包括其中數目9位置經兩個氫、兩個烷基、兩個芳基或兩個雜芳基取代的芴基的概念。更特定言之,可使用9-二-H-芴基、9-二-甲基-芴基、9-二-苯基-芴基或類似基團。
在本說明書中,雜環烷基包括O、S、Se、N或Si作為雜原子,包括C2至C60單環或多環,且可進一步經其他取代基取代。本文中,多環意謂其中雜環烷基直接鍵聯至另一環狀基團或與另一環狀基團稠合的基團。本文中,另一環狀基團可為雜環烷基,但亦可包括其他類型的環狀基團,例如環烷基、芳基以及雜芳基。雜環烷基的碳原子數可為2至60,特定言之2至40,且更特定言之3至20。
在本說明書中,芳基包括C6至C60單環或多環,且可進一步經其他取代基取代。本文中,多環意謂其中芳基直接鍵聯至另一環狀基團或與另一環狀基團稠合的基團。本文中,另一環狀基團可為芳基,但亦可包括其他類型的環狀基團,例如環烷基、雜環烷基以及雜芳基。芳基包括螺環基團。芳基的碳原子數可為6至60,特定言之6至40,特定言之6至30且更特定言之6至25。芳基的特定實例可包括(但不限於)苯基、聯苯基、聯三苯基、萘基、蒽基、屈基、菲基、苝基、芴蒽基、聯伸三苯基、丙烯合萘基、芘基、稠四苯基、稠五苯基、芴基、茚基、苊基、苯并芴基、螺聯芴基、2,3-二氫-1H-茚基、其稠環基團以及類似基團。
在本說明書中,螺環基團是包括螺環結構的基團,且可為C15至C60。舉例而言,螺環基團可包括一種結構,所述結構中2,3-二氫-1H-茚基或環己烷基螺鍵結至芴基。特定言之,螺環基團可包括以下結構式的群組中的任一者。
在本說明書中,雜芳基包括S、O、Se、N或Si作為雜原子,包括C2至C60單環或多環,且可進一步經其他取代基取代。本文中,多環意謂其中雜芳基直接鍵聯至另一環狀基團或與另一環狀基團稠合的基團。本文中,另一環狀基團可為雜芳基,但亦可包括其他類型的環狀基團,例如環烷基、雜環烷基以及芳基。雜芳基的碳原子數可為2至60,特定言之2至40,特定言之2至30且更特定言之3至25。雜芳基的特定實例可包括(但不限於)吡啶基、吡咯基、嘧啶基、噠嗪基、呋喃基、噻吩基、咪唑基、吡唑基、噁唑基、異噁唑基、噻唑基、異噻唑基、三唑基、呋呫基、噁二唑基、噻二唑基、二噻唑基、四唑基、哌喃基、硫代哌喃基、二嗪基、噁嗪基、噻嗪基、二氧基(dioxynyl group)、三嗪基、四嗪基、喹啉基、異喹啉基、喹唑啉基、異喹唑啉基(isoquinazolinyl group)、喹啉唑啉基(quinozolinyl group)、萘啶基、吖啶基、啡啶基、咪唑并吡啶基、二氮雜萘基、三吖茚基、吲哚基、吲哚嗪基、苯并噻唑基、苯并噁唑基、苯并咪唑基、苯并噻吩基、苯并呋喃基、二苯并噻吩基、二苯并呋喃基、咔唑基、苯并咔唑基、二苯并咔唑基、啡嗪基、二苯并矽羅基、螺二(二苯并矽羅)、二氫啡嗪基(dihydrophenazinyl group)、啡噁嗪基、啡基(phenanthridyl group)、咪唑并吡啶基、噻吩基、吲哚并[2,3-a]咔唑基、吲哚并[2,3-b]咔唑基、吲哚啉基、10,11-二氫-二苯并[b,f]氮呯基、9,10-二氫吖啶基、菲嗪基(phenanthrazinyl group)、吩噻噻嗪基(phenothiathiazinyl group)、酞嗪基、萘啶基(naphthyridinyl group)、啡啉基、苯并[c][1,2,5]噻二唑基、5,10-二氫二苯并[b,e][1,4]氮雜啉基(5,10-dihydrodibenzo[b,e][1,4]azasilinyl)、吡唑并[1,5-c]喹唑啉基、吡啶并[1,2-b]吲唑基、吡啶并[1,2-a]咪唑并[1,2-e]吲哚啉基、5,11-二氫茚并[1,2-b]咔唑基以及類似基團。
在本說明書中,胺基可由下述者所組成之群組中選出:單烷基胺基、單芳基胺基、單雜芳基胺基、-NH2
、二烷基胺基、二芳基胺基、二雜芳基胺基、烷基芳基胺基、烷基雜芳基胺基以及芳基雜芳基胺基,且儘管碳原子數不受其特定限制,但較佳為1至30。胺基的特定實例可包括(但不限於)甲胺基、二甲胺基、乙胺基、二乙胺基、苯胺基、萘胺基、聯苯胺基、二聯苯胺基、蒽胺基(anthracenylamine group)、9-甲基-蒽胺基、二苯胺基、苯基萘胺基、二甲苯胺基(ditolylamine group)、苯基甲苯胺基、三苯胺基、聯苯萘胺基、苯基聯苯胺基、聯苯芴胺基、苯基聯伸三苯基胺基(phenyltriphenylenylamine group)、聯苯基聯伸三苯基胺基(biphenyltriphenylenylamine group)以及類似基團。
在本說明書中,伸芳基意謂具有兩個鍵結位點的芳基,亦即二價基團。除各自為二價基團以外,以上所提供的關於芳基的描述可應用於此。另外,伸雜芳基意謂具有兩個鍵結位點的雜芳基,亦即二價基團。除各自為二價基團以外,以上所提供的關於雜芳基的描述可應用於此。
在本說明書中,電洞特性指代能夠藉由在施加電場時供給電子來形成電洞的特性,且意謂(藉由具有沿HOMO能級的傳導特性)有助於將陽極中形成的電洞注入至發光層、發光層中形成的電洞遷移至陽極以及在發光層中的遷移的特性。
具有電洞特性的取代基包括具有電洞特性的經取代或未經取代的C6至C60芳基、具有電洞特性的經取代或未經取代的C2至C60雜芳基、經取代或未經取代的芳基胺基、經取代或未經取代的雜芳基胺基或類似基團。
更特定言之,具有電洞特性的經取代或未經取代的C6至C60芳基可為經取代或未經取代的苯基、經取代或未經取代的萘基、經取代或未經取代的菲基、經取代或未經取代的蒽基、經取代或未經取代的芴基、經取代或未經取代的聯伸三苯基、經取代或未經取代的螺-芴基、經取代或未經取代的聯三苯基、經取代或未經取代的芘基、經取代或未經取代的苝基或其組合。
更特定言之,具有電洞特性的經取代或未經取代的C2至C60雜芳基為經取代或未經取代的咔唑基、經取代或未經取代的二苯并呋喃基、經取代或未經取代的二苯并噻吩基、經取代或未經取代的吲哚咔唑基或類似基團。
更特定言之,芳基或雜芳基、鍵結至經取代或未經取代的芳基胺基及經取代或未經取代的雜芳基胺基的氮的取代基可為經取代或未經取代的苯基、經取代或未經取代的萘基、經取代或未經取代的蒽基、經取代或未經取代的菲基、經取代或未經取代的稠四苯基、經取代或未經取代的芘基、經取代或未經取代的聯苯基、經取代或未經取代的對聯三苯基、經取代或未經取代的間聯三苯基、經取代或未經取代的屈基、經取代或未經取代的聯伸三苯基、經取代或未經取代的苝基、經取代或未經取代的茚基、經取代或未經取代的呋喃基、經取代或未經取代的噻吩基、經取代或未經取代的吡咯基、經取代或未經取代的吡唑基、經取代或未經取代的咪唑基、經取代或未經取代的三唑基、經取代或未經取代的噁唑基、經取代或未經取代的噻唑基、經取代或未經取代的噁二唑基、經取代或未經取代的噻二唑基、經取代或未經取代的吡啶基、經取代或未經取代的嘧啶基、經取代或未經取代的吡嗪基、經取代或未經取代的三嗪基、經取代或未經取代的苯并呋喃基、經取代或未經取代的苯并噻吩基、經取代或未經取代的苯并咪唑基、經取代或未經取代的吲哚基、經取代或未經取代的喹啉基、經取代或未經取代的異喹啉基、經取代或未經取代的喹唑啉基、經取代或未經取代的喹喏啉基、經取代或未經取代的萘啶基、經取代或未經取代的苯并噁嗪基、經取代或未經取代的苯并噻嗪基、經取代或未經取代的吖啶基、經取代或未經取代的啡嗪基、經取代或未經取代的啡噻嗪基、經取代或未經取代的啡噁嗪基或其組合。
另外,電子特性指代能夠在施加電場時接收電子的特性,且意謂(藉由具有沿LUMO能級的傳導特性)有助於將陰極中形成的電子注入至發光層、發光層中形成的電子遷移至陰極以及在發光層中的遷移的特性。
具有電子特性的經取代或未經取代的C2至C60雜芳基可為經取代或未經取代的咪唑基、經取代或未經取代的四唑基、經取代或未經取代的伸喹啉基、經取代或未經取代的伸異喹啉基、經取代或未經取代的伸吡啶基、經取代或未經取代的伸嘧啶基、經取代或未經取代的伸三嗪基、經取代或未經取代的呋喃基、經取代或未經取代的苯并呋喃基、經取代或未經取代的異呋喃基、經取代或未經取代的苯并異呋喃基、經取代或未經取代的噁唑啉基、經取代或未經取代的苯并噁唑啉基、經取代或未經取代的噁二唑啉基、經取代或未經取代的苯并噁二唑啉基、經取代或未經取代的噁三唑基、經取代或未經取代的噻吩基、經取代或未經取代的苯并噻吩基、經取代或未經取代的異噻唑啉、經取代或未經取代的苯并異噻唑啉基、經取代或未經取代的噻唑啉、經取代或未經取代的苯并噻唑啉基、經取代或未經取代的噠嗪基、經取代或未經取代的苯并噠嗪基、經取代或未經取代的吡嗪基、經取代或未經取代的苯并吡嗪基、經取代或未經取代的酞嗪基、經取代或未經取代的苯并喹啉基、經取代或未經取代的喹喏啉基、經取代或未經取代的喹唑啉基、經取代或未經取代的吖啶基、經取代或未經取代的啡啉基、經取代或未經取代的啡嗪基或其組合。
更特定言之,具有電子特性的經取代或未經取代的C2至C60雜芳基可為以下化學式X-1至X-5中的任一者。
[化學式X-1]
[化學式X-2]
[化學式X-3] [化學式X-4]
[化學式X-4]
[化學式X-5]
在本申請案的一個實施例中,Ln
可為直接鍵(或單鍵)、經取代或未經取代的伸芳基或經取代或未經取代的伸雜芳基。
在另一實施例中,Ln
可為直接鍵、經取代或未經取代的C6至C60伸芳基或經取代或未經取代的C2至C60伸雜芳基。
在另一實施例中,Ln
可為直接鍵、經取代或未經取代的C6至C40伸芳基或經取代或未經取代的C2至C40伸雜芳基。
在Ln
中,n意謂用於區分取代基的數目。
下文中,將描述根據一個實施例的化合物。
在化學式1中,
X1
及X2
中的至少一者為-N-,另一者為-CA-,Y為-S-或-O-,A以及R1
至R8
各自獨立地為氫、氘、氰基、經取代或未經取代的C1至C60烷基或經取代或未經取代的C6至C60芳基,且A以及R1
至R4
中的任一者由以下化學式2表示,
[化學式2]
在化學式2中,
Ar1
及Ar2
各自獨立地為經取代或未經取代的C6至C60芳基或經取代或未經取代的C2至C60雜芳基,X3
至X7
中的至少一者為-N-,X3
至X7
中的一者為-(L1
)n1
-Ar1
,X3
至X7
中的一者為-Ar2
-且其餘為-N-、-CH-或-CR-中的一者,L1
及L2
各自獨立地為單鍵、經取代或未經取代的C6至C60伸芳基或經取代或未經取代的C2至C60伸雜芳基,n1及n2各自獨立地為0至2的整數中的一者,R為氘、-CN、經取代或未經取代的C1至C60直鏈或分支鏈烷基、經取代或未經取代的C6至C60單環或多環芳基或經取代或未經取代的C2至C60單環或多環雜芳基,且當化學式1的A由化學式2表示時,化學式2的Ar1
及Ar2
中的至少任一者為經取代或未經取代的C2至C60雜芳基或經取代或未經取代的C6至C60稠環芳基,且*為鍵結位置。
在化學式1-1中,
X1
及X2
中的至少一者為-N-,且另一者為-CA-,
Y為-S-或-O-,
A以及R1
至R8
各自獨立地為氫、氘、氰基、經取代或未經取代的C1至C60烷基或經取代或未經取代的C6至C60芳基,且
A以及R1
至R4
中的任一者由以下化學式2表示,
[化學式2]
在化學式2中,
Ar1
及Ar2
各自獨立地為經取代或未經取代的C6至C60芳基或經取代或未經取代的C2至C60雜芳基,
Ar1
及Ar2
中的至少任一者為經取代或未經取代的C2至C60雜芳基或經取代或未經取代的C6至C60稠環芳基,
X3
至X7
中的至少一者為-N-,X3
至X7
中的一者為-(L1
)n1
-Ar1
,X3
至X7
中的一者為-Ar2
-,且其餘為-N-、-CH-或-CR-中的一者,
L1
及L2
各自獨立地為單鍵、經取代或未經取代的C6至C60伸芳基或經取代或未經取代的C2至C60伸雜芳基,
n1及n2各自獨立地為0至2的整數中的一者,
R為氘、-CN、經取代或未經取代的C1至C60直鏈或分支鏈烷基、經取代或未經取代的C6至C60單環或多環芳基或經取代或未經取代的C2至C60單環或多環雜芳基,且
*為鍵結位置。
本文中,稠環芳基意謂其中碳原子共用相鄰對的環狀基團。
特定言之,C6至C60稠環芳基可為經取代或未經取代的萘基、經取代或未經取代的聯伸三苯基、經取代或未經取代的芴基、經取代或未經取代的芘基或經取代或未經取代的菲基。
本申請案是關於化學式1或化學式1-1的化合物。
另外,藉由將各種取代基引入至化學式1的結構,可合成具有所引入取代基的獨特特性的化合物。舉例而言,藉由將通常用作用於製造有機發光二極體的電洞注入層材料、電洞轉移層材料、發光層材料、電子轉移層材料以及電荷產生層材料的取代基引入至芯結構,可合成滿足每一有機材料層所需條件的材料。
另外,藉由將各種取代基引入至化學式1的結構,可精細控制能帶隙,且同時,強化有機材料之間的界面處的特性,且材料應用可變得多樣化。
同時,化合物具有高玻璃轉化溫度(Tg),且藉此具有極佳熱穩定性。熱穩定性的此類提高成為向裝置提供驅動穩定性的重要因素。
在化學式3中,
Ar1
及Ar2
各自獨立地為經取代或未經取代的C6至C60芳基或經取代或未經取代的C2至C60雜芳基,X3
至X5
各自獨立地為-N-、-CH-或-CR-,X3
至X5
中的至少一者為-N-,L1
及L2
各自獨立地為單鍵、經取代或未經取代的C6至C60伸芳基或經取代或未經取代的C2至C60伸雜芳基,n1及n2各自獨立地為0至2的整數中的一者,且R為氘、-CN、經取代或未經取代的C1至C60直鏈或分支鏈烷基、經取代或未經取代的C6至C60單環或多環芳基或經取代或未經取代的C2至C60單環或多環雜芳基,
當化學式1的A由化學式3表示時,化學式3的Ar1
及Ar2
中的至少任一者為經取代或未經取代的C2至C60雜芳基或經取代或未經取代的C6至C60稠環芳基,且*為鍵結位置。
在化學式3中,
Ar1
及Ar2
各自獨立地為經取代或未經取代的C6至C60芳基或經取代或未經取代的C2至C60雜芳基,Ar1
及Ar2
中的至少任一者為經取代或未經取代的C2至C60雜芳基或經取代或未經取代的C6至C60稠環芳基,X3
至X5
各自獨立地為-N-、-CH-或-CR-,X3
至X5
中的至少一者為-N-,L1
及L2
各自獨立地為單鍵、經取代或未經取代的C6至C60伸芳基或經取代或未經取代的C2至C60伸雜芳基,n1及n2各自獨立地為0至2的整數中的一者,且R為氘、-CN、經取代或未經取代的C1至C60直鏈或分支鏈烷基、經取代或未經取代的C6至C60單環或多環芳基或經取代或未經取代的C2至C60單環或多環雜芳基,且
*為鍵結位置。
在具有由化學式3表示的取代基的化合物中,Ar1
及Ar2
各自為獨立的,且具有經取代或未經取代的C2至C60雜芳基或經取代或未經取代的C6至C60稠環芳基的取代基相較於其他取代基具有相對更強的電洞轉移特性。具有強電洞轉移特性影響整體電子遷移,且可獲得更優良的效率及使用壽命。
在化學式4中,
各取代基具有與化學式1中相同的定義。
在化學式5中,
各取代基具有與化學式1中相同的定義。
更特定言之,在化學式4的化合物中,X1
為-N-,X2
為-CA-,且A可由化學式3表示。
更特定言之,在化學式4的化合物中,X1
為-CA-,X2
為-N-,且A可由化學式3表示。
更特定言之,在化學式4的化合物中,X1
為-N-,X2
為-CA-,且R1
至R4
中的任一者可由化學式3表示。
更特定言之,在化學式4的化合物中,X1
為-CA-,X2
為-N-,且R1
至R4
中的任一者可由化學式3表示。
另外,更特定言之,在化學式4的化合物中,X1
為-N-,X2
為-CA-,R1
至R4
中的任一者由化學式3表示,且A可為苯基或萘基。
另外,更特定言之,在化學式4的化合物中,X1
為-CA-,X2
為-N-,R1
至R4
中的任一者由化學式3表示,且A可為苯基或萘基。
更特定言之,在化學式5的化合物中,X1
為-N-,X2
為-CA-,且A可由化學式3表示。
更特定言之,在化學式5的化合物中,X1
為-CA-,X2
為-N-,且A可由化學式3表示。
更特定言之,在化學式5的化合物中,X1
為-N-,X2
為-CA-,且R1
至R4
中的任一者可由化學式3表示。
更特定言之,在化學式5的化合物中,X1
為-CA-,X2
為-N-,且R1
至R4
中的任一者可由化學式3表示。
另外,更特定言之,在化學式5的化合物中,X1
為-N-,X2
為-CA-,R1
至R4
中的任一者由化學式3表示,且A可為苯基或萘基。
另外,更特定言之,在化學式5的化合物中,X1
為-CA-,X2
為-N-,R1
至R4
中的任一者由化學式3表示,且A可為苯基或萘基。
另外,Ar1
可為具有電洞特性的取代基。
在本申請案的一個實施例中,L1
及L2
可各自獨立地為單鍵、經取代或未經取代的C6至C60伸芳基或經取代或未經取代的C2至C60伸雜芳基。
在另一實施例中,L1
及L2
可各自獨立地為單鍵、經取代或未經取代的C6至C40伸芳基或經取代或未經取代的C2至C40伸雜芳基。
在另一實施例中,L1
及L2
可各自獨立地為單鍵、C6至C40伸芳基或C2至C40伸雜芳基。
在另一實施例中,L1
及L2
可各自獨立地為單鍵或單環或多環C6至C40伸芳基。
在另一實施例中,L1
及L2
可各自獨立地為單鍵、伸苯基、伸聯苯基或萘基。
在本申請案的一個實施例中,Ar1
及Ar2
可各自獨立地為經取代或未經取代的C6至C60芳基或經取代或未經取代的C2至C60雜芳基。
在另一實施例中,Ar1
及Ar2
可各自獨立地為經取代或未經取代的C6至C40芳基或經取代或未經取代的C2至C40雜芳基。
在另一實施例中,Ar1
及Ar2
可各自獨立地為未經取代或經C1至C10烷基取代的C6至C40芳基,或未經取代或經C6至C10芳基取代的C2至C40雜芳基。
在另一實施例中,Ar1
及Ar2
可各自獨立地為經取代或未經取代的苯基、經取代或未經取代的萘基、經取代或未經取代的聯苯基、經取代或未經取代的聯伸三苯基、經取代或未經取代的芴基、經取代或未經取代的芘基、經取代或未經取代的菲基、經取代或未經取代的咔唑基、經取代或未經取代的二苯并噻吩基或經取代或未經取代的二苯并呋喃基。
在另一實施例中,Ar1
及Ar2
可各自獨立地為苯基、萘基、聯苯基、聯伸三苯基、未經取代或經甲基取代的芴基、苯環稠合的9,9-二甲基芴基、芘基、菲基、未經取代或經苯基取代的咔唑基、未經取代或經苯基取代的二苯并噻吩基或未經取代或經苯基取代的二苯并呋喃基。
在本申請案的一個實施例中,A以及R1
至R8
各自獨立地為氫、氘、氰基、經取代或未經取代的C1至C60烷基或經取代或未經取代的C6至C60芳基,且A以及R1
至R4
中的任一者可由化學式2表示。
在另一實施例中,A以及R1
至R8
各自獨立地為氫或經取代或未經取代的C6至C60芳基,且A以及R1
至R4
中的任一者可由化學式2表示。
在另一實施例中,A以及R1
至R8
各自獨立地為氫或經取代或未經取代的C6至C40芳基,且A以及R1
至R4
中的任一者可由化學式2表示。
在另一實施例中,A以及R1
至R8
各自獨立地為氫或C6至C40芳基,且A以及R1
至R4
中的任一者可由化學式2表示。
在另一實施例中,A以及R1
至R8
各自獨立地為氫、苯基或萘基,且A以及R1
至R4
中的任一者可由化學式2表示。
在本申請案的一個實施例中,當A由化學式2表示時,化學式2的Ar1
及Ar2
中的至少任一者可為經取代或未經取代的C2至C60雜芳基或經取代或未經取代的C6至C60稠環芳基。
在另一實施例中,當A由化學式2表示時,化學式2的Ar1
及Ar2
中的至少任一者可為經取代或未經取代的C2至C40雜芳基或經取代或未經取代的C6至C40稠環芳基。
在另一實施例中,當A由化學式2表示時,化學式2的Ar1
及Ar2
中的至少任一者可為未經取代或經C6至C20芳基取代的C2至C40雜芳基,或C6至C40稠環芳基。
在另一實施例中,當A由化學式2表示時,化學式2的Ar1
及Ar2
中的至少任一者可為未經取代或經苯基取代的咔唑基、未經取代或經苯基取代的二苯并噻吩基、未經取代或經苯基取代的二苯并呋喃基、聯伸三苯基、9,9-二甲基芴基、苯環稠合的9,9-二甲基芴基、菲基或芘基。
更特定言之,Ar1
為經取代或未經取代的咔唑基、經取代或未經取代的二苯并呋喃基、經取代或未經取代的二苯并噻吩基、經取代或未經取代的9,9-二烷基芴基或9,9-二芳基芴基,且二烷基的烷基可為經取代或未經取代的C1至C60烷基,且二芳基的芳基可為經取代或未經取代的C6至C60芳基或經取代,或未經取代的9,9-二甲基芴基。
在由此等取代基表示時,相較於其他情況,有機發光二極體的發光效率及使用壽命可更優良。
更特定言之,Ar1
可為經取代或未經取代的蒽基(anthracenyl group)、經取代或未經取代的菲基(phenanthryl group)、經取代或未經取代的芘基(pyrenyl group)、經取代或未經取代的聯伸三苯基(triphenylenyl group)、經取代或未經取代的聯三苯基(terphenyl group)或經取代或未經取代的對聯四苯基(quaterphenyl group)。
在由此等取代基表示時,相較於其他情況,有機發光二極體的發光效率及使用壽命可更優良。
上文所描述的化合物或組合物可用於有機光電二極體,且可使用諸如化學氣相沈積的乾膜形成方法來形成用於有機光電二極體的化合物或用於有機光電二極體的組合物。
下文中,將描述使用上文所描述的用於有機光電二極體的化合物或用於有機光電二極體的組合物的有機光電二極體。
有機光電二極體不受特定限制,只要其為能夠進行電能與光能互轉換的裝置即可,且其實例可包括有機光電二極體、有機發光二極體、有機太陽能電池、有機光導鼓以及類似物。
本申請案的另一實施例提供一種有機發光二極體,所述有機發光二極體包括:第一電極;第二電極,與第一電極相對設置;以及一或多個有機材料層,設置於第一電極與第二電極之間,其中有機材料層的一或多個層包括由化學式1表示的雜環化合物。
在本申請案的一個實施例中,第一電極可為陽極,且第二電極可為陰極。
在另一實施例中,第一電極可為陰極,且第二電極可為陽極。
由化學式1表示的雜環化合物的特定細節與上文所提供的描述相同。
在本申請案的一個實施例中,有機發光二極體可為藍色有機發光二極體,且根據化學式1的雜環化合物可用作藍色有機發光二極體的材料。
在本申請案的一個實施例中,有機發光二極體可為綠色有機發光二極體,且根據化學式1的雜環化合物可用作綠色有機發光二極體的材料。
在本申請案的一個實施例中,有機發光二極體可為紅色有機發光二極體,且根據化學式1的雜環化合物可用作紅色有機發光二極體的材料。
本揭露內容的有機發光二極體可使用通用有機發光二極體製造方法及材料製造,不同之處在於使用上文所描述的雜環化合物來形成一或多個有機材料層。
在製造有機發光二極體時,可使用溶液塗佈法以及真空沈積法來使雜環化合物形成為有機材料層。本文中,溶液塗佈法意謂(但不限於)旋塗、浸塗、噴墨印刷、網版印刷、噴霧法、滾塗法以及類似方法。
本文中,將參考附圖描述有機發光二極體的另一實例,有機光電二極體的一個實例。
圖1至圖3示出根據本申請案的一個實施例的有機發光二極體的電極與有機材料層的層壓次序。然而,本申請案的範疇不限於此等圖式,且本申請案中亦可使用所屬領域中已知的有機光電二極體的結構。
圖1示出其中陽極200、有機材料層300以及陰極400連續地層壓在基板100上的有機發光二極體。然而,結構不限於此類結構,且如圖2中所示出,亦可獲得陰極、有機材料層以及陽極連續地層壓在基板上的有機發光二極體。
圖3示出有機材料層為多層的情況。根據圖3的有機發光二極體包括電洞注入層301、電洞轉移層302、發光層303、電洞阻擋層304、電子轉移層305以及電子注入層306。然而,本申請案的範疇不限於此類層壓結構,且視需要,可不包含除發光層以外的層,且可進一步包含其他必要的功能層。
在有機發光二極體中,由化學式1表示的化合物可用作電子轉移層、電洞轉移層、電洞阻擋層、發光層或類似物的材料。更特定言之,由化學式1表示的化合物可用作有機發光二極體中的電子轉移層或電洞阻擋層的材料。
可使用具有相對較大功函數的材料作為陽極材料,且可使用透明的導電氧化物、金屬、導電聚合物或類似材料作為陽極材料。陽極材料的特定實例包括(但不限於):金屬,諸如釩、鉻、銅、鋅以及金,或其合金;金屬氧化物,諸如氧化鋅、氧化銦、氧化銦錫(indium tin oxide;ITO)以及氧化銦鋅(indium zinc oxide;IZO);金屬與氧化物的組合,諸如ZnO:Al或SnO2
:Sb;導電聚合物,諸如聚(3-甲基噻吩)、聚[3,4-(乙烯-1,2-二氧基)噻吩](poly[3,4-(ethylene-1,2-dioxy)thiophene];PEDOT)、聚吡咯以及聚苯胺,以及類似物。
可使用具有相對小功函數的材料作為陰極材料,且可使用金屬、金屬氧化物、導電聚合物或類似材料作為陰極材料。陰極材料的特定實例包括(但不限於):金屬,諸如鎂、鈣、鈉、鉀、鈦、銦、釔、鋰、釓、鋁、銀、錫以及鉛,或其合金;多層結構材料,諸如LiF/Al或LiO2
/Al,以及類似物。
可使用已知的電洞注入材料作為電洞注入材料,且例如可使用:酞菁化合物,諸如美國專利第4,356,429號中所揭露的銅酞菁;或星爆型(starburst-type)胺衍生物,諸如於文獻[高級材料(Advanced Material), 6, 第677頁(1994)]中描述的三(4-肼甲醯基-9-基苯基)胺(tris(4-carbazoyl-9-ylphenyl)amine;TCTA)、4,4',4"-三[苯基(間甲苯基)胺基]三苯胺(4,4',4"-tri[phenyl(m-tolyl)amino]triphenylamine;間MTDATA)或1,3,5-三[4-(3-甲基苯基苯基胺基)苯基]苯(1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene;間MTDAPB);具有溶解性的導電聚合物,聚苯胺/十二烷基苯磺酸、聚(3,4-伸乙二氧基噻吩)/聚(4-苯乙烯磺酸脂)、聚苯胺/樟腦磺酸或聚苯胺/聚(4-苯乙烯-磺酸酯);以及類似材料。
可使用吡唑啉衍生物、芳基胺類衍生物、二苯乙烯衍生物、三苯基二胺衍生物以及類似材料作為電洞轉移材料,且亦可使用低分子或高分子材料。
可使用發紅光、綠光或藍光的材料作為發光材料,且視需要可將兩種或大於兩種發光材料混合並用作發光材料。本文中,兩種或大於兩種發光材料可藉由沈積為個別供應源或藉由預混合及沈積為一個供應源而使用。另外,亦可使用螢光材料作為發光材料,然而,亦可使用磷光材料。可單獨使用藉由鍵結分別自陽極及陰極注入的電子及電洞來發光的材料作為發光材料,然而,亦可使用具有一起參與發光的主體材料及摻雜材料的材料作為發光材料。
當混合發光材料主體時,可混合相同系列主體,或可混合不同系列主體。舉例而言,N型主體材料或P型主體材料中的任何兩種或更大於兩種類型的材料可經選擇且用作發光層的主體材料。
電洞阻擋材料的實例可包括三唑衍生物、浴銅靈(bathocuproine)或鋁的混合配位子錯合物(BAlq),然而,本申請案不限於此,且亦可使用本揭露內容的一個實施例的化合物。
電子轉移材料可為本揭露內容的一個實施例的化合物。
作為電子注入材料的實例,所屬領域中通常使用LiF,然而,本申請案不限於此。
根據本申請案的一個實施例的有機發光二極體可取決於所使用的材料而為頂部發射型、底部發射型或雙發射型。
下文中,將藉由實例更詳細地描述上文所描述的實施例。然而,以下實例僅出於說明性目的且並不限制權利範疇。
(製備用於有機光電二極體的化合物)
在使苯并[b]噻吩-2-基硼酸(100公克,0.561莫耳)及2-溴苯胺(86.7公克,0.504莫耳)溶解於甲苯中之後,向其中引入EtOH及H2
O(1000毫升:200毫升:200毫升)、Pd(PPh3
)4
(32.4公克,0.028莫耳)以及NaHCO3
(141.3公克,1.68莫耳),且在100℃下攪拌所得物3小時。在反應完成之後,藉由向其中引入MC及蒸餾水來萃取反應溶液。此後,所得物經無水MgSO4
脫水,且使用旋轉式汽化器移除溶劑以獲得液態型化合物1-1(93公克,74%)。
2)製備化合物1-2
將化合物1-1(93公克,0.412莫耳)及三乙胺(86毫升,0.618莫耳)引入至MC(1200毫升)中且使其溶解於MC中。在0℃下將溶解於MC(300毫升)中的4-溴苯甲醯氯(135.6公克,0.618莫耳)緩慢地逐滴添加至混合物中。在反應完成之後,反應溶液中存在的白色固體經過濾且用己烷洗滌。乾燥所得物以獲得固體型化合物1-2(134公克,83%)。
3)製備化合物1-3
在使化合物1-2(134公克,0.329莫耳)溶解於硝基苯(1500毫升)中之後,向其中緩慢地逐滴添加POCl3
(46毫升,0.495莫耳)。使所得物在140℃下反應15小時。在反應完成之後,將藉由使NaHCO3
溶解於蒸餾水中而獲得的溶液緩慢地引入至反應溶液中,且攪拌所得物。過濾並收集此後產生的固體。所收集的固體經由MC及MeOH再結晶以獲得固體型化合物1-3(65公克,51%)。
4)製備化合物1-4
在使化合物1-3(10公克,0.025莫耳)、雙(頻哪醇根基)二硼(9.7公克,0.038莫耳)、KOAc(7.3公克,0.075莫耳)以及PdCl2
(dppf)(0.9公克,0.0012莫耳)溶解於1,4-二氧陸圜(200毫升)中之後,使所得物在90℃下反應5小時。在反應完成之後,藉由向其中引入MC及蒸餾水來萃取反應溶液。此後,所得物經無水MgSO4
脫水,且使用MC及己烷作為展開溶劑進行管柱層析以獲得化合物1-4(7.6公克,70%)。
5)製備化合物1
在使化合物1-4(7.6公克,0.017莫耳)及9-(4-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-9H-咔唑(7.3公克,0.017莫耳)溶解於1,4-二氧陸圜:H2
O(100毫升:20毫升)中之後,向其中引入Pd2
(dba)3
(1.5公克,0.0017莫耳)、XPhos(1.6公克,0.0034莫耳)以及K2
CO3
(7.0公克,0.051莫耳),且在100℃下攪拌所得物5小時。在反應完成之後,用1,4-二氧陸圜及H2
O洗滌反應溶液中產生的固體。此後,在DCB中使用再結晶方法僅純化固體以獲得化合物1(7.2公克,60%)。
[製備實例1-2]
使用中間物A替代9-(4-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例1-1中相同的方式合成目標化合物。
[表1]
[製備實例1-3]
化合物編號 | 中間物A | 目標化合物 | 產率 |
17 | 61% | ||
21 | 63% | ||
29 | 60% | ||
40 | 61% | ||
42 | 54% | ||
50 | 61% | ||
52 | 60% | ||
55 | 62% | ||
60 | 63% | ||
62 | 64% | ||
250 | 61% | ||
264 | 60% | ||
266 | 60% | ||
270 | 61% | ||
283 | 62% | ||
285 | 61% | ||
290 | 60% | ||
296 | 60% | ||
299 | 61% | ||
462 | 60% | ||
465 | 61% |
使用3-溴苯甲醯氯替代4-溴苯甲醯氯且使用中間物B替代9-(4-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例1-1中相同的方式合成目標化合物。
[表2]
[製備1-4]
化合物編號 | 中間物B | 目標化合物 | 產率 |
11 | 62% | ||
16 | 65% | ||
20 | 65% | ||
65 | 62% | ||
254 | 51% | ||
259 | 60% | ||
275 | 61% | ||
297 | 60% |
使用4-溴-1-萘甲醯氯替代4-溴苯甲醯氯且使用中間物C替代9-(4-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例1-1中相同的方式合成目標化合物。
[表3]
[製備實例2-1]製備化合物71
1)製備化合物2-1
化合物編號 | 中間物C | 目標化合物 | 產率 |
13 | 53% | ||
24 | 55% | ||
38 | 53% | ||
44 | 53% | ||
265 | 55% | ||
282 | 52% | ||
288 | 52% |
在使苯并[b]噻吩-3-基硼酸(100公克,0.561莫耳)及2-溴苯胺(86.7公克,0.504莫耳)溶解於甲苯中之後,向其中引入EtOH及H2
O(1000毫升:200毫升:200毫升)、Pd(PPh3
)4
(32.4公克,0.028莫耳)以及NaHCO3
(141.3公克,1.68莫耳),且在100℃下攪拌所得物3小時。在反應完成之後,藉由向其中引入MC及蒸餾水來萃取反應溶液。此後,所得物經無水MgSO4
脫水,且使用旋轉式汽化器移除溶劑以獲得液態型化合物2-1(93公克,74%)。
2)製備化合物2-2
將化合物2-1(93公克,0.412莫耳)及三乙胺(86毫升,0.618莫耳)引入至MC(1200毫升)中且使其溶解於MC中。在0℃下將溶解於MC(300毫升)中的4-溴苯甲醯氯(135.6公克,0.618莫耳)緩慢地逐滴添加至混合物中。在反應完成之後,反應溶液中存在的白色固體經過濾且用己烷洗滌。乾燥所得物以獲得固體型化合物2-2(134公克,83%)。
3)製備化合物2-3
在使化合物2-2(134公克,0.329莫耳)溶解於硝基苯(1500毫升)中之後,向其中緩慢地逐滴添加POCl3
(46毫升,0.495莫耳)。使所得物在140℃下反應15小時。在反應完成之後,將藉由使NaHCO3
溶解於蒸餾水中而獲得的溶液緩慢地引入至反應溶液中,且攪拌所得物。過濾並收集此後產生的固體。所收集的固體經由MC及MeOH再結晶以獲得固體型化合物2-3(65公克,51%)。
4)製備化合物2-4
在使化合物2-3(10公克,0.025莫耳)、雙(頻哪醇根基)二硼(9.7公克,0.038莫耳)、KOAc(7.3公克,0.075莫耳)以及PdCl2
(dppf)(0.9公克,0.0012莫耳)溶解於1,4-二氧陸圜(200毫升)中之後,使所得物在90℃下反應5小時。在反應完成之後,藉由向其中引入MC及蒸餾水來萃取反應溶液。此後,所得物經無水MgSO4
脫水,且使用MC及己烷作為展開溶劑進行管柱層析以獲得化合物2-4(7.6公克,70%)。
5)製備化合物71
在使化合物2-4(7.6公克,0.017莫耳)及9-(3-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-9H-咔唑(7.3公克,0.017莫耳)溶解於1,4-二氧陸圜:H2
O(100毫升:20毫升)中之後,向其中引入Pd2
(dba)3
(1.5公克,0.0017莫耳)、XPhos(1.6公克,0.0034莫耳)以及K2
CO3
(7.0公克,0.051莫耳),且在100℃下攪拌所得物5小時。在反應完成之後,用1,4-二氧陸圜及H2
O洗滌反應溶液中產生的固體。此後,在DCB中使用再結晶方法僅純化固體以獲得化合物71(7.2公克,60%)。
[製備實例2-2]
使用中間物D替代9-(3-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例2-1中相同的方式合成目標化合物。
[表4]
[製備實例2-3]
化合物編號 | 中間物D | 目標化合物 | 產率 |
72 | 60% | ||
78 | 61% | ||
80 | 62% | ||
87 | 63% | ||
98 | 62% | ||
106 | 61% | ||
116 | 61% | ||
122 | 61% | ||
125 | 60% | ||
303 | 61% | ||
310 | 62% | ||
316 | 61% | ||
318 | 60% | ||
324 | 61% | ||
326 | 60% | ||
332 | 60% | ||
341 | 60% | ||
348 | 60% | ||
350 | 61% | ||
359 | 62% | ||
467 | 60% |
使用3-溴苯甲醯氯替代4-溴苯甲醯氯且使用中間物E替代9-(3-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例2-1中相同的方式合成目標化合物。
[表5]
[製備實例2-4]
化合物編號 | 中間物E | 目標化合物 | 產率 |
82 | 62% | ||
93 | 61% | ||
100 | 62% | ||
315 | 59% | ||
331 | 61% | ||
336 | 61% |
使用4-溴-1-萘甲醯氯替代4-溴苯甲醯氯且使用中間物F替代9-(3-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例2-2中相同的方式合成目標化合物。
[表6]
[製備實例3-1]製備化合物130
1)製備化合物3-1
化合物編號 | 中間物F | 目標化合物 | 產率 |
75 | 53% | ||
84 | 60% | ||
114 | 54% | ||
305 | 53% | ||
307 | 53% | ||
330 | 51% | ||
471 | 59% |
引入3-溴苯并[b]噻吩(100公克,0.469莫耳)及乙酸(1500毫升)且在室溫下攪拌10分鐘,且向其中緩慢地逐滴添加乙酸(1500毫升)及HNO3
(200毫升)的混合物。在反應在1小時內完成之後,使所得物冷卻至室溫且用蒸餾水及MC萃取。在用MgSO4
使有機層脫水之後,使用旋轉式汽化器移除溶劑,且使用MC及己烷作為展開溶劑藉由管柱層析法純化所得物以獲得化合物3-1(90公克,77%)。
2)製備化合物3-2
引入化合物3-1(90公克,0.087莫耳)、乙醇(3000毫升)以及Fe粉末(60公克,0.108莫耳),且在室溫下攪拌10分鐘。向其中緩慢地逐滴添加乙酸(300毫升),且所得物在60℃下回流持續1小時。在反應完成之後,所得物冷卻至室溫,向其中添加H2
O,且所產生固體經過濾且接著用H2
O及己烷洗滌以獲得化合物3-2(70公克,99%)。
3)製備化合物3-3
化合物3-2(70公克,0.306莫耳)、苯硼酸(40公克,0.336莫耳)、Pd(PPh3
)4
(17公克,0.0153莫耳)以及Na2
CO3
(65公克,0.609莫耳)在120℃下與甲苯(700毫升)、乙醇(140毫升)以及H2
O(140毫升)一起回流持續1小時。在反應完成之後,所得物冷卻至室溫且用蒸餾水及EA萃取。在用MgSO4 使
有機層脫水之後,使用旋轉式汽化器移除溶劑,且所得物經用EA及己烷洗滌以獲得化合物3-3(63公克,90%)。
4)製備化合物3-4
使化合物3-3(90公克,0.399莫耳)溶解於MC中,且在室溫下與TEA(56毫升,0.399莫耳)一起攪拌15分鐘。此後,使溫度維持在0℃,且向其中緩慢地添加4-溴苯甲醯氯(87公克,0.399莫耳)。過濾且用EA及己烷洗滌1小時後產生的白色固體,以獲得化合物3-4(150公克,90%)。
5)製備化合物3-5
引入化合物3-4(150公克,0.3674莫耳)、POCl3
(51毫升,0.551莫耳)以及硝基苯(1500毫升),且攪拌1小時。使所得物在140℃下反應15小時。在反應完成之後,將藉由使NaHCO3
溶解於蒸餾水中而獲得的溶液緩慢地引入至反應溶液中,且攪拌所得物。過濾並收集此後產生的固體。用甲醇及己烷洗滌所收集的固體,以獲得化合物3-5(110公克,77%)。
6)製備化合物3-6
在使化合物3-6(50公克,0.128莫耳)、雙(頻哪醇根基)二硼(48.7公克,0.192莫耳)、KOAc(37公克,0.384莫耳)以及PdCl2
(dppf)(4.6公克,0.0064莫耳)溶解於1,4-二氧陸圜(1000毫升)中之後,使所得物在90℃下反應5小時。在反應完成之後,藉由向其中引入MC及蒸餾水來萃取反應溶液。此後,所得物經無水MgSO4
脫水,且使用MC及己烷作為展開溶劑進行管柱層析以獲得化合物3-6(39公克,70%)。
7)製備化合物130
在使化合物3-6(7公克,0.016莫耳)及9-(3-(4-氯-6-(萘-2-基)-1,3,5-三嗪-2-基)苯基)-9H-咔唑(7.7公克,0.016莫耳)溶解於1,4-二氧陸圜:H2
O(100毫升:20毫升)中之後,向其中引入Pd2
(dba)3
(1.4公克,0.0016莫耳)、XPhos(1.5公克,0.0032莫耳)以及K2
CO3
(6.6公克,0.048莫耳),且在100℃下攪拌所得物5小時。在反應完成之後,用1,4-二氧陸圜及H2
O洗滌反應溶液中產生的固體。此後,在DCB中使用再結晶方法僅純化固體以獲得化合物130(7.2公克,60%)。
[製備實例3-2]
使用中間物G替代9-(3-(4-氯-6-(萘-2-基)-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例3-1中相同的方式合成目標化合物。
[表7]
[製備實例3-3]
化合物編號 | 中間物G | 目標化合物 | 產率 |
127 | 61% | ||
140 | 61% | ||
150 | 62% | ||
152 | 60% | ||
166 | 61% | ||
362 | 60% | ||
364 | 60% | ||
373 | 60% | ||
382 | 63% | ||
385 | 63% | ||
391 | 59% | ||
396 | 61% |
使用3-溴苯甲醯氯替代4-溴苯甲醯氯且使用中間物H替代9-(3-(4-氯-6-(萘-2-基)-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例3-1中相同的方式合成目標化合物。
[表8]
[製備實例3-4]
化合物編號 | 中間物H | 目標化合物 | 產率 |
137 | 62% | ||
141 | 59% | ||
146 | 58% | ||
165 | 59% | ||
169 | 54% | ||
179 | 54% | ||
363 | 60% | ||
370 | 62% | ||
375 | 62% | ||
393 | 61% |
使用4-溴-1-萘甲醯氯替代4-溴苯甲醯氯且使用中間物I替代9-(3-(4-氯-6-(萘-2-基)-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例3-1中相同的方式合成目標化合物。
[表9]
[製備實例4-1]製備化合物190
1)製備化合物4-1
化合物編號 | 中間物I | 目標化合物 | 產率 |
135 | 53% | ||
144 | 60% | ||
155 | 61% | ||
366 | 61% | ||
371 | 61% | ||
386 | 62% | ||
408 | 59% |
苯并[b]噻吩-2-基硼酸(50公克,0.280莫耳)、碘苯(57公克,0.280莫耳)、Pd(PPh3
)4
(16.2公克,0.014莫耳)以及Na2
CO3
(89.6公克,0.84莫耳)在120℃下與甲苯(1000毫升)、乙醇(200毫升)以及H2
O(200毫升)一起回流持續1小時。在反應完成之後,所得物冷卻至室溫且用蒸餾水及EA萃取。在用MgSO4
使有機層脫水之後,使用旋轉式汽化器移除溶劑以獲得化合物4-1(53公克,90%)。
2)製備化合物4-2
引入化合物4-1(50公克,0.237莫耳)及乙酸(700毫升)且在室溫下攪拌10分鐘,且向其中緩慢地逐滴添加乙酸(700毫升)及HNO3
(100毫升)的混合物。在反應在1小時內完成之後,使所得物冷卻至室溫且用蒸餾水及MC萃取。在用MgSO4
使有機層脫水之後,使用旋轉式汽化器移除溶劑,且使用MC及己烷作為展開溶劑藉由管柱層析法純化所得物以獲得化合物4-2(46公克,77%)。
3)製備化合物4-3
引入化合物4-2(46公克,0.182莫耳)、乙醇(1000毫升)以及Fe粉末(30公克,0.546莫耳),且在室溫下攪拌10分鐘。向其中緩慢地逐滴添加乙酸(130毫升),且使所得物在60℃下回流持續1小時。在反應完成之後,所得物冷卻至室溫,向其中添加H2
O,且所產生固體經過濾且接著用H2
O及己烷洗滌以獲得化合物4-3(40公克,99%)。
4)製備化合物4-4
使溶解化合物4-3(40公克,0.177莫耳)於中MC,且在室溫下與TEA(25毫升,0.177莫耳)一起攪拌15分鐘。此後,使溫度維持在0℃,且向其中緩慢地添加4-溴苯甲醯氯(77公克,0.354莫耳)。過濾且用EA及己烷洗滌1小時後產生的白色固體,以獲得化合物4-4(57公克,80%)。
5)製備化合物4-5
引入化合物4-4(57公克,0.139莫耳)、POCl3
(19.5毫升,0.208莫耳)以及硝基苯(500毫升),且在140℃下反應15小時。在反應完成之後,將藉由使NaHCO3
溶解於蒸餾水中而獲得的溶液緩慢地引入至反應溶液中,且攪拌所得物。過濾並收集此後產生的固體。用甲醇及己烷洗滌所收集的固體,以獲得化合物4-5(40公克,74%)。
6)製備化合物4-6
在使化合物4-5(40公克,0.102莫耳)、雙(頻哪醇根基)二硼(39公克,0.153莫耳)、KOAc(30公克,0.306莫耳)以及PdCl2
(dppf)(3.7公克,0.0051莫耳)溶解於1,4-二氧陸圜(1000毫升)中之後,使所得物在90℃下反應5小時。在反應完成之後,藉由向其中引入MC及蒸餾水來萃取反應溶液。此後,所得物經無水MgSO4
脫水,且使用MC及己烷作為展開溶劑進行管柱層析以獲得化合物4-6(31公克,70%)。
7)製備化合物190
在使化合物4-6(7公克,0.016莫耳)及9-(4-(4-氯-6-(萘-2-基)-1,3,5-三嗪-2-基)苯基)-9H-咔唑(7.7公克,0.016莫耳)溶解於1,4-二氧陸圜:H2
O(100毫升:20毫升)中之後,向其中引入Pd2
(dba)3
(1.4公克,0.0016莫耳)、XPhos(1.5公克,0.0032莫耳)以及K2
CO3
(6.6公克,0.048莫耳),且在100℃下攪拌所得物5小時。在反應完成之後,用1,4-二氧陸圜及H2
O洗滌反應溶液中產生的固體。此後,在DCB中使用再結晶方法僅純化固體以獲得化合物190(7.2公克,60%)。
[製備實例4-2]
使用中間物J替代9-(4-(4-氯-6-(萘-2-基)-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例4-1中相同的方式合成目標化合物。
[表10]
[製備實例4-3]
化合物編號 | 中間物J | 目標化合物 | 產率 |
199 | 64% | ||
220 | 63% | ||
231 | 60% | ||
234 | 60% | ||
242 | 61% | ||
419 | 63% | ||
431 | 60% | ||
432 | 60% | ||
441 | 61% | ||
445 | 64% | ||
450 | 63% | ||
452 | 60% | ||
460 | 61% | ||
476 | 61% |
使用3-溴苯甲醯氯替代4-溴苯甲醯氯且使用中間物K替代9-(4-(4-氯-6-(萘-2-基)-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例4-1中相同的方式合成目標化合物。
[表11]
[製備實例4-4]
化合物編號 | 中間物K | 目標化合物 | 產率 |
198 | 64% | ||
203 | 63% | ||
209 | 60% | ||
226 | 60% | ||
247 | 63% | ||
422 | 60% | ||
424 | 60% |
使用2-溴苯甲醯氯替代4-溴苯甲醯氯且使用中間物L替代9-(4-(4-氯-6-(萘-2-基)-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例4-1中相同的方式合成目標化合物。
[表12]
[製備實例4-5]
化合物編號 | 中間物L | 目標化合物 | 產率 |
196 | 57% |
使用4-溴-1-萘甲醯氯替代4-溴苯甲醯氯且使用中間物M替代9-(4-(4-氯-6-(萘-2-基)-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例4-1中相同的方式合成目標化合物。
[表13]
[製備實例5-1]製備化合物480
1)製備化合物5-1
化合物編號 | 中間物M | 目標化合物 | 產率 |
219 | 53% | ||
416 | 64% | ||
443 | 60% | ||
456 | 60% |
使用苯并呋喃-2-基硼酸替代苯并[b]噻吩-2-基硼酸以與製備實例1-1的化合物1-1的製備相同的方式獲得化合物5-1(95公克,74%)。
2)製備化合物5-2
使用化合物5-1替代化合物1-1以與製備實例1-1的化合物1-2的製備相同的方式獲得化合物5-2(126公克,80%)。
3)製備化合物5-3
使用化合物5-2替代化合物1-2以與製備實例1-1的化合物1-3的製備相同的方式獲得化合物5-3(60公克,50%)。
4)製備化合物5-4
使用化合物5-3替代化合物1-3以與製備實例1-1的化合物1-4的製備相同的方式獲得化合物5-4(7.8公克,70%)。
5)製備化合物480
使用化合物5-3替代化合物1-4且使用9-(4-(4-([1,1'-聯苯]-2-基)-6-氯-1,3,5-三嗪-2-基)苯基)-9H-咔唑替代9-(4-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例1-1的化合物1的製備相同的方式獲得化合物480(5.8公克,60%)。
[製備實例5-2]
使用中間物N替代9-(4-(4-([1,1'-聯苯]-2-基)-6-氯-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例5-1中相同的方式合成目標化合物。
[表14]
[製備實例5-3]
化合物編號 | 中間物N | 目標化合物 | 產率 |
479 | 64% | ||
486 | 60% | ||
493 | 61% | ||
498 | 64% | ||
502 | 63% | ||
508 | 60% | ||
511 | 60% | ||
540 | 63% | ||
725 | 60% | ||
727 | 60% | ||
736 | 63% | ||
740 | 60% | ||
742 | 60% | ||
748 | 61% | ||
750 | 64% | ||
754 | 63% | ||
763 | 60% | ||
768 | 64% | ||
774 | 63% | ||
936 | 60% | ||
938 | 61% |
使用3-溴苯甲醯氯替代4-溴苯甲醯氯且使用中間物O替代9-(4-(4-([1,1'-聯苯]-2-基)-6-氯-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例5-1中相同的方式合成目標化合物。
[表15]
[製備實例5-4]
化合物編號 | 中間物O | 目標化合物 | 產率 |
488 | 64% | ||
517 | 60% | ||
519 | 60% | ||
524 | 61% | ||
537 | 64% | ||
737 | 60% | ||
751 | 61% | ||
753 | 64% | ||
757 | 63% |
使用4-溴-1-萘甲醯氯替代4-溴苯甲醯氯且使用中間物P替代9-(4-(4-([1,1'-聯苯]-2-基)-6-氯-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例5-1中相同的方式合成目標化合物。
[表16]
[製備實例6-1]製備化合物546
1)製備化合物6-1
化合物編號 | 中間物P | 目標化合物 | 產率 |
499 | 51% | ||
506 | 50% | ||
527 | 53% | ||
731 | 51% | ||
641 | 50% | ||
736 | 54% | ||
765 | 51% |
使用苯并呋喃-3-基硼酸替代苯并[b]噻吩-3-基硼酸以與製備實例2-1的化合物2-1的製備相同的方式獲得化合物6-1(90公克,70%)。
2)製備化合物6-2
使用化合物6-1替代化合物2-1以與製備實例2-1的化合物2-2的製備相同的方式獲得化合物6-2(134公克,80%)。
3)製備化合物6-3
使用化合物6-2替代化合物2-2以與製備實例2-1的化合物2-3的製備相同的方式獲得化合物6-3(63公克,50%)。
4)製備化合物6-4
使用化合物6-3替代化合物2-3以與製備實例2-1的化合物2-4的製備相同的方式獲得化合物6-4(49公克,70%)。
5)製備化合物546
使用化合物6-4替代化合物2-4且使用9-(4-(4-氯-6-苯基-1,3,5-三嗪-2-基)萘-1-基)-9H-咔唑替代9-(3-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例2-1的化合物71的製備相同的方式獲得化合物546(7.3公克,60%)。
[製備實例6-2]
使用中間物Q替代9-(4-(4-氯-6-苯基-1,3,5-三嗪-2-基)萘-1-基)-9H-咔唑以與製備實例6-1中相同的方式合成目標化合物。
[表17]
[製備實例6-3]
化合物編號 | 中間物Q | 目標化合物 | 產率 |
557 | 60% | ||
559 | 60% | ||
563 | 61% | ||
567 | 64% | ||
578 | 60% | ||
585 | 60% | ||
591 | 61% | ||
593 | 64% | ||
597 | 60% | ||
598 | 60% | ||
777 | 64% | ||
778 | 63% | ||
780 | 60% | ||
786 | 64% | ||
789 | 63% | ||
798 | 60% | ||
803 | 60% | ||
816 | 60% | ||
824 | 60% | ||
830 | 61% | ||
943 | 60% |
使用3-溴苯甲醯氯替代4-溴苯甲醯氯且使用中間物R替代9-(4-(4-氯-6-苯基-1,3,5-三嗪-2-基)萘-1-基)-9H-咔唑以與製備實例6-1中相同的方式合成目標化合物。
[表18]
[製備實例6-4]
化合物編號 | 中間物R | 目標化合物 | 產率 |
553 | 64% | ||
562 | 63% | ||
576 | 60% | ||
579 | 64% | ||
588 | 60% | ||
784 | 60% | ||
788 | 64% | ||
796 | 60% | ||
818 | 61% |
使用4-溴-1-萘甲醯氯替代4-溴苯甲醯氯且使用中間物S替代9-(4-(4-氯-6-苯基-1,3,5-三嗪-2-基)萘-1-基)-9H-咔唑以與製備實例6-1中相同的方式合成目標化合物。
[表19]
[製備實例7-1]製備化合物609
1)製備化合物7-1
化合物編號 | 中間物S | 目標化合物 | 產率 |
550 | 63% | ||
573 | 64% | ||
587 | 63% | ||
782 | 60% | ||
811 | 64% | ||
820 | 63% | ||
829 | 60% | ||
833 | 60% |
使用3-溴苯并呋喃替代3-溴苯并[b]噻吩以與製備實例3-1的化合物3-1的製備相同的方式獲得化合物7-1(92公克,75%)。
2)製備化合物7-2
使用化合物7-1替代化合物3-1以與製備實例3-1的化合物3-2的製備相同的方式獲得化合物7-2(89公克,97%)。
3)製備化合物7-3
使用化合物7-2替代化合物3-2以與製備實例3-1的化合物3-3的製備相同的方式獲得化合物7-3(79,90%)。
4)製備化合物7-4
使用化合物7-3替代化合物3-3以與製備實例3-1的化合物3-4的製備相同的方式獲得化合物7-4(133公克,90%)。
5)製備化合物7-5
使用化合物7-4替代化合物3-4以與製備實例3-1的化合物3-5的製備相同的方式獲得化合物7-5(121公克,70%)。
6)製備化合物7-6
使用化合物7-5替代化合物3-5以與製備實例3-1的化合物3-6的製備相同的方式獲得化合物7-6(41公克,68%)。
7)製備化合物609
使用化合物7-6替代化合物3-6且使用9-(4-(4-([1,1'-聯苯]-4-基)-6-氯-1,3,5-三嗪-2-基)苯基)-9H-咔唑替代9-(3-(4-氯-6-(萘-2-基)-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例3-1的化合物130的製備相同的方式獲得化合物609(7.4公克,0.58%)。
[製備實例7-2]
使用中間物T替代9-(4-(4-([1,1'-聯苯]-4-基)-6-氯-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例7-1中相同的方式合成目標化合物。
[表20]
[製備實例7-3]
化合物編號 | 中間物T | 目標化合物 | 產率 |
605 | 64% | ||
616 | 60% | ||
618 | 60% | ||
626 | 61% | ||
638 | 63% | ||
650 | 60% | ||
661 | 60% | ||
836 | 64% | ||
837 | 63% | ||
844 | 64% | ||
854 | 60% | ||
856 | 64% | ||
864 | 60% | ||
867 | 60% | ||
882 | 61% | ||
948 | 60% |
使用3-溴苯甲醯氯替代4-溴苯甲醯氯且使用中間物U替代9-(4-(4-([1,1'-聯苯]-4-基)-6-氯-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例7-1中相同的方式合成目標化合物。
[表21]
[製備實例7-4]
化合物編號 | 中間物U | 目標化合物 | 產率 |
604 | 64% | ||
613 | 63% | ||
617 | 60% | ||
641 | 64% | ||
645 | 63% | ||
663 | 60% | ||
839 | 64% | ||
846 | 63% | ||
848 | 60% | ||
866 | 60% | ||
874 | 61% | ||
876 | 64% | ||
880 | 63% | ||
885 | 60% | ||
886 | 60% |
使用4-溴-1-萘甲醯氯替代4-溴苯甲醯氯且使用中間物V替代9-(4-(4-([1,1'-聯苯]-4-基)-6-氯-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例7-1中相同的方式合成目標化合物。
[表22]
[製備實例8-1]製備化合物664
1)製備化合物8-1
化合物編號 | 中間物V | 目標化合物 | 產率 |
608 | 64% | ||
621 | 63% | ||
632 | 60% | ||
653 | 61% | ||
852 | 60% | ||
865 | 60% | ||
879 | 61% |
使用苯并呋喃-2-基硼酸替代苯并[b]噻吩-2-基硼酸以與製備實例4-1的化合物4-1的製備相同的方式獲得化合物8-1(54公克,91%)。
2)製備化合物8-2
使用化合物8-1替代化合物4-1以與製備實例4-1的化合物4-2的製備相同的方式獲得化合物8-2(50公克,72%)。
3)製備化合物8-3
使用化合物8-2替代化合物4-2以與製備實例4-1的化合物4-3的製備相同的方式獲得化合物8-3(42公克,97%)。
4)製備化合物8-4
使用化合物8-3替代化合物4-3以與製備實例4-1的化合物4-4的製備相同的方式獲得化合物8-4(63公克,80%)。
5)製備化合物8-5
使用化合物8-4替代化合物4-4以與製備實例4-1的化合物4-5的製備相同的方式獲得化合物8-5(46公克,76%)。
6)製備化合物8-6
使用化合物8-5替代化合物4-5以與製備實例4-1的化合物4-6的製備相同的方式獲得化合物8-6(36公克,70%)。
7)製備化合物664
使用化合物8-6替代化合物4-6且使用9-(4-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-3-苯基-9H-咔唑替代9-(4-(4-氯-6-(萘-2-基)-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例4-1的化合物210的製備相同的方式獲得化合物664(9公克,62%)。
[製備實例8-2]
使用中間物W替代9-(4-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-3-苯基-9H-咔唑以與製備實例8-1中相同的方式合成目標化合物。
[表23]
[製備實例8-3]
化合物編號 | 中間物W | 目標化合物 | 產率 |
666 | 64% | ||
668 | 63% | ||
681 | 60% | ||
696 | 63% | ||
703 | 60% | ||
712 | 61% | ||
722 | 64% | ||
888 | 63% | ||
889 | 60% | ||
897 | 61% | ||
902 | 64% | ||
906 | 63% | ||
907 | 60% | ||
917 | 61% | ||
930 | 60% | ||
931 | 60% |
使用3-溴苯甲醯氯替代4-溴苯甲醯氯且使用中間物X替代9-(4-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-3-苯基-9H-咔唑以與製備實例8-1中相同的方式合成目標化合物。
[表24]
[製備實例8-4]
化合物編號 | 中間物X | 目標化合物 | 產率 |
667 | 64% | ||
674 | 63% | ||
680 | 60% | ||
687 | 64% | ||
691 | 63% | ||
700 | 60% | ||
724 | 61% | ||
898 | 63% | ||
905 | 60% | ||
916 | 60% | ||
920 | 60% | ||
935 | 60% | ||
949 | 60% |
使用4-溴-1-萘甲醯氯替代4-溴苯甲醯氯且使用中間物Y替代9-(4-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-3-苯基-9H-咔唑以與製備實例8-1中相同的方式合成目標化合物。
[表25]
[製備實例9-1]製備化合物935
1)製備化合物9-1
化合物編號 | 中間物Y | 目標化合物 | 產率 |
671 | 63% | ||
682 | 60% | ||
699 | 64% | ||
721 | 63% | ||
894 | 60% | ||
903 | 61% | ||
913 | 60% |
在使苯并[b]噻吩-2-基硼酸(100公克,0.561莫耳)及2-溴苯胺(86.7公克,0.504莫耳)溶解於甲苯中之後,向其中引入EtOH及H2
O(1000毫升:200毫升:200毫升)、Pd(PPh3
)4
(32.4公克,0.028莫耳)以及NaHCO3
(141.3公克,1.68莫耳),且在100℃下攪拌所得物3小時。在反應完成之後,藉由向其中引入MC及蒸餾水來萃取反應溶液。此後,所得物經無水MgSO4
脫水,且使用旋轉式汽化器移除溶劑以獲得液態型化合物9-1(93公克,74%)。
2)製備化合物9-2
將化合物9-1(93公克,0.412莫耳)及三乙胺(86毫升,0.618莫耳)引入至MC(1200毫升)中且使其溶解於MC中。在0℃下將溶解於MC(300毫升)中的苯甲醯氯(135.6公克,0.618莫耳)緩慢地逐滴添加至混合物中。在反應完成之後,反應溶液中存在的白色固體經過濾且用己烷洗滌。乾燥所得物以獲得固體型化合物9-2(134公克,83%)。
3)製備化合物9-3
在使化合物9-2(134公克,0.329莫耳)溶解於硝基苯(1500毫升)中之後,向其中緩慢地逐滴添加POCl3
(46毫升,0.495莫耳)。使所得物在140℃下反應15小時。在反應完成之後,將藉由使NaHCO3
溶解於蒸餾水中而獲得的溶液緩慢地引入至反應溶液中,且攪拌所得物。過濾並收集此後產生的固體。所收集的固體經由MC及MeOH再結晶以獲得固體型化合物9-3(65公克,51%)。
4)製備化合物9-4
引入化合物9-3(10公克,0.0352莫耳,1當量)、NBS(7.5公克,0.0423莫耳,1.2當量)以及乙酸(AcOH)(200毫升,20 T),且攪拌20分鐘。向其中緩慢地引入H2
SO4
(100毫升,10T)。在室溫下攪拌所得物1小時,且向其中引入水(150毫升)以使反應終止。所得物經用MC萃取,經矽石過濾以移除雜質,且接著用MeOH攪拌。過濾所產生固體以獲得化合物9-4(10.6公克,81%)。
5)製備化合物9-5
在使化合物9-4(38公克,0.102莫耳)、雙(頻哪醇根基)二硼(39公克,0.153莫耳)、KOAc(30公克,0.306莫耳)以及PdCl2
(dppf)(3.7公克,0.0051莫耳)溶解於1,4-二氧陸圜(1000毫升)中之後,使所得物在90℃下反應5小時。在反應完成之後,藉由向其中引入MC及蒸餾水來萃取反應溶液。此後,所得物經無水MgSO4
脫水,且過濾固體以獲得化合物9-5(28公克,67%)。
6)製備化合物935
在使化合物9-5(6.7公克,0.016莫耳)及9-(3-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-9H-咔唑(6.8公克,0.016莫耳)溶解於1,4-二氧陸圜:H2
O(100毫升:20毫升)中之後,向其中引入Pd2
(dba)3
(1.4公克,0.0016莫耳)、XPhos(1.5公克,0.0032莫耳)以及K2
CO3
(6.6公克,0.048莫耳),且在100℃下攪拌所得物5小時。在反應完成之後,用1,4-二氧陸圜及H2
O洗滌反應溶液中產生的固體。此後,在DCB中使用再結晶方法僅純化固體以獲得化合物935(7.2公克,64%)。
[製備實例9-2]
使用中間物Z替代9-(3-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例9-1中相同的方式合成目標化合物。
[表26]
[製備實例10-1]製備化合物1046
1)製備化合物10-1
化合物編號 | 中間物Z | 目標化合物 | 產率 |
956 | 63% | ||
960 | 61% | ||
962 | 68% | ||
966 | 62% | ||
969 | 61% | ||
973 | 61% | ||
975 | 68% | ||
981 | 68% | ||
984 | 68% | ||
986 | 62% | ||
989 | 62% | ||
991 | 67% | ||
996 | 60% | ||
1003 | 63% | ||
1007 | 60% | ||
1013 | 62% | ||
1014 | 62% | ||
1030 | 61% | ||
1031 | 61% | ||
1033 | 61% |
使用苯并呋喃-2-基硼酸替代苯并[b]噻吩-2-基硼酸以與製備實例9-1的化合物9-1的製備相同的方式獲得化合物10-1(54公克,91%)。
2)製備化合物10-2
使用化合物10-1替代化合物9-1以與製備實例9-1的化合物9-2的製備相同的方式獲得化合物10-2(50公克,72%)。
3)製備化合物10-3
使用化合物10-2替代化合物9-2以與製備實例9-1的化合物9-3的製備相同的方式獲得化合物10-3(42公克,97%)。
4)製備化合物10-4
使用化合物10-3替代化合物9-3以與製備實例9-1的化合物9-4的製備相同的方式獲得化合物10-4(63公克,80%)。
5)製備化合物10-5
使用化合物10-4替代化合物9-4以與製備實例9-1的化合物9-5的製備相同的方式獲得化合物10-5(46公克,76%)。
6)製備化合物1046
使用化合物10-5替代化合物9-5且使用2-氯-4-(二苯并[b,d]呋喃-1-基)-6-苯基-1,3,5-三嗪替代9-(3-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例9-1的化合物935的製備相同的方式獲得化合物1046(7公克,65%)。
[製備實例10-2]
使用中間物a替代2-氯-4-(二苯并[b,d]呋喃-1-基)-6-苯基-1,3,5-三嗪以與製備實例10-1中相同的方式合成目標化合物。
[表27]
[製備實例11-1]製備化合物1084
1)製備化合物11-1
化合物編號 | 中間物a | 目標化合物 | 產率 |
1020 | 63% | ||
1021 | 62% | ||
1034 | 61% | ||
1035 | 67% | ||
1036 | 61% | ||
1039 | 62% | ||
1041 | 61% | ||
1042 | 62% | ||
1044 | 60% | ||
1049 | 62% | ||
1052 | 60% | ||
1053 | 65% | ||
1057 | 65% | ||
1058 | 60% | ||
1061 | 60% | ||
1065 | 63% | ||
1072 | 65% | ||
1073 | 65% | ||
1078 | 61% | ||
1082 | 64% |
在使苯并[b]噻吩-3-基硼酸(100公克,0.561莫耳)及2-溴苯胺(86.7公克,0.504莫耳)溶解於甲苯中之後,向其中引入EtOH及H2
O(1000毫升:200毫升:200毫升)、Pd(PPh3
)4
(32.4公克,0.028莫耳)以及NaHCO3
(141.3公克,1.68莫耳),且在100℃下攪拌所得物3小時。在反應完成之後,藉由向其中引入MC及蒸餾水來萃取反應溶液。此後,所得物經無水MgSO4
脫水,且使用旋轉式汽化器移除溶劑以獲得液態型化合物11-1(93公克,74%)。
2)製備化合物11-2
將化合物11-1(93公克,0.412莫耳)及三乙胺(86毫升,0.618莫耳)引入至MC(1200毫升)中且使其溶解於MC中。在0℃下將溶解於MC(300毫升)中的苯甲醯氯(135.6公克,0.618莫耳)緩慢地逐滴添加至混合物中。在反應完成之後,反應溶液中存在的白色固體經過濾且用己烷洗滌。乾燥所得物以獲得固體型化合物11-2(134公克,83%)。
3)製備化合物11-3
在使化合物11-2(134公克,0.329莫耳)溶解於硝基苯(1500毫升)中之後,向其中緩慢地逐滴添加POCl3
(46毫升,0.495莫耳)。使所得物在140℃下反應15小時。在反應完成之後,將藉由使NaHCO3
溶解於蒸餾水中而獲得的溶液緩慢地引入至反應溶液中,且攪拌所得物。過濾並收集此後產生的固體。所收集的固體經由MC及MeOH再結晶以獲得固體型化合物11-3(65公克,51%)。
4)製備化合物11-4
引入化合物11-3(10公克,0.0352莫耳,1當量)、NBS(7.5公克,0.0423莫耳,1.2當量)以及AcOH(200毫升,20 T),且攪拌20分鐘。向其中緩慢地引入H2
SO4
(100毫升,10 T)。在室溫下攪拌所得物1小時,且向其中引入水(150毫升)以使反應終止。所得物經用MC萃取,經矽石過濾以移除雜質,且接著用MeOH攪拌。過濾所產生固體以獲得化合物11-4(10.6公克,81%)。
5)製備化合物11-5
在使化合物11-4(38公克,0.102莫耳)、雙(頻哪醇根基)二硼(39公克,0.153莫耳)、KOAc(30公克,0.306莫耳)以及PdCl2
(dppf)(3.7公克,0.0051莫耳)溶解於1,4-二氧陸圜(1000毫升)中之後,使所得物在90℃下反應5小時。在反應完成之後,藉由向其中引入MC及蒸餾水來萃取反應溶液。此後,所得物經無水MgSO4
脫水,且過濾固體以獲得化合物11-5(28公克,67%)。
6)製備化合物1084
在使化合物11-5(6.7公克,0.016莫耳)及9-(4-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-9H-咔唑(6.8公克,0.016莫耳)溶解於1,4-二氧陸圜:H2
O(100毫升:20毫升)中之後,向其中引入Pd2
(dba)3
(1.4公克,0.0016莫耳)、XPhos(1.5公克,0.0032莫耳)以及K2
CO3
(6.6公克,0.048莫耳),且在100℃下攪拌所得物5小時。在反應完成之後,用1,4-二氧陸圜及H2
O洗滌反應溶液中產生的固體。此後,在DCB中使用再結晶方法僅純化固體以獲得化合物1084(7.2公克,64%)。
[製備實例11-2]
使用中間物b替代9-(4-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例11-1中相同的方式合成目標化合物。
[表28]
[製備實例12-1]製備化合物1129
1)製備化合物12-1
化合物編號 | 中間物b | 目標化合物 | 產率 |
1026 | 60% | ||
1090 | 63% | ||
1091 | 61% | ||
1093 | 66% | ||
1098 | 63% | ||
1102 | 64% | ||
1103 | 66% | ||
1105 | 65% | ||
1109 | 63% | ||
1111 | 61% | ||
1114 | 66% | ||
1119 | 63% | ||
1121 | 60% | ||
1124 | 61% |
使用苯并呋喃-3-基硼酸替代苯并呋喃-2-基硼酸以與製備實例10-1的化合物10-1的製備相同的方式獲得化合物12-1(54公克,91%)。
2)製備化合物12-2
使用化合物12-1替代化合物10-1以與製備實例10-1的化合物10-2的製備相同的方式獲得化合物12-2(50公克,72%)。
3)製備化合物12-3
使用化合物12-2替代化合物10-2以與製備實例10-1的化合物10-3的製備相同的方式獲得化合物12-3(42公克,97%)。
4)製備化合物12-4
使用化合物12-3替代化合物10-3以與製備實例10-1的化合物10-4的製備相同的方式獲得化合物12-4(63公克,80%)。
5)製備化合物12-5
使用化合物12-4替代化合物10-4以與製備實例10-1的化合物10-5的製備相同的方式獲得化合物12-5(46公克,76%)。
6)製備化合物1129
使用化合物12-5替代化合物10-4且使用9-(3-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-9H-咔唑替代2-氯-4-(二苯并[b,d]呋喃-1-基)-6-苯基-1,3,5-三嗪以與製備實例10-1的化合物1046的製備相同的方式獲得化合物1129(7公克,65%)。
[製備實例12-2]
使用中間物c替代9-(3-(4-氯-6-苯基-1,3,5-三嗪-2-基)苯基)-9H-咔唑以與製備實例10-1中相同的方式合成目標化合物。
[表29]
化合物編號 | 中間物c | 目標化合物 | 產率 |
1027 | 66% | ||
1135 | 65% | ||
1138 | 63% | ||
1142 | 61% | ||
1143 | 66% | ||
1146 | 65% | ||
1147 | 63% | ||
1150 | 61% | ||
1151 | 66% | ||
1157 | 65% | ||
1162 | 63% | ||
1165 | 60% | ||
1166 | 64% | ||
1169 | 64% |
由質量及NMR結果鑑定所製備化合物。
[表30]
[表31]
[實驗實例1](製造有機發光二極體-電子轉移層)
[比較例1]
化合物 | 1 H NMR (CDCl3 , 300 Mz) | |
1 | δ=8.69(2H, 2d), 8.55(1H, d), 8.45(1H, d), 8.36(2H, d), 8.20(1H, d), 7.96~85(10H, m), 7.70(1H, t), 7.58~7.49 (7H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
11 | δ=8.55(1H, d), 8.45(1H, d), 8.36~8.33(4H, m), 8.24~8.19(4H, m), 7.96~7.84(6H, m), 7.73~7.49(12H, m), 7.35(1H, t), 7.25~7.16(4H, m) | |
13 | δ=8.97(2H, d), 8.68(1H, d), 8.55(1H, d), 8.45(1H, d), 8.36(2H, d), 8.29(1H, d), 8.20(1H, d), 7.94~7.85(8H, m), 7.70(1H, t), 7.59~7.49(9H, m), 7.35(1H, t), 7.20(1H, t), 7.16(1H, t) | |
16 | δ=8.55(1H, d), 8.45~8.33(6H, m), 8.20(1H, d), 7.94~7.85(5H, m), 7.73~7.70(3H, m), 7.56~7.49(7H, m) | |
17 | δ=8.69(2H, d), 8.55(1H, d), 8.45(2H, d), 8.36(2H, d), 8.20(1H, d), 7.96~7.85(9H, m), 7.70(2H, m), 7.56~7.49(7H, m), 7.25(2H, d) | |
20 | δ=8.55(1H, d), 8.45~8.33(6H, m), 8.20(1H, d), 7.96~7.85(7H, m), 7.73~7.70(3H, m), 7.61~7.49(8H, m), 7.25(2H, d) | |
21 | δ=8.69(2H, d), 8.45~8.36(5H, m), 8.20(1H, d), 8.03~7.85(9H, m), 7.70~7.49(11H, m) | |
24 | δ=9.02(1H, d), 8.95(1H, d), 8.55(1H, d), 8.45~8.36(5H, m), 8.20(1H, d), 7.96~7.85(8H, m), 7.70(2H, t), 7.56~7.46(9H, m), 7.25(2H, d) | |
29 | δ=8.69(2H, d), 8.45(1H, d), 8.36(2H, d), 8.20(1H, d), 7.96~7.79(9H, m), 7.70(1H, t), 7.56~7.31(8H, m) | |
38 | δ=9.02(1H, d), 8.95(1H, d), 8.45(2H, d), 8.36(2H, d), 8.20(1H, d), 8.08(1H, d), 7.96~7.85(8H, m), 7.70(1H, t), 7.54~7.25(13H, m) | |
40 | δ=8.69(2H, d), 8.45~8.36(4H, m), 8.20(1H, d), 8.08(1H, d), 7.94~7.85(8H, m), 7.73~7.70(2H, m), 7.56~7.49(8H, m, 7.39~7.31(2H, m) | |
42 | δ=9.60(1H, d), 9.27(1H, s), 8.69(2H, d), 8.45(1H, d), 8.36~8.30(4H, m), 8.20~8.15(2H, m), 7.96~7.85(5H, m), 7.70~7.49(12H, m) | |
44 | δ=9.60(1H, d), 9.27(1H, s), 8.97(2H, d), 8.68(1H, d), 8.45(1H, d), 8.36~8.29(5H, m), 8.20~8.15(2H, m), 7.94~7.85(3H, m), 7.70~7.49(14H, m) | |
50 | δ=9.09(1H, s), 8.69(2H, d), 8.49~8.45(2H, m), 8.20~8.16(2H, m), 8.08~7.85(9H, m), 7.70~7.49(8H, m), 7.38(1H, t), 7.28(1H, t), 1.69(6H, s) | |
52 | δ=8.69(2H, d), 8.45(1H, d), 8.36(2H, d), 8.20(1H, d), 8.09(1H, d), 7.96~7.70(11H, m), 7.56~7.49(6H, m), 7.38(1H, t), 7.28~7.25(3H, m), 1.69(6H, s) | |
55 | δ=8.69(2H, d), 8.52~8.45(2H, d), 8.36~8.31(3H, m), 8.20~7.85(12H, m), 7.70(2H, m), 7.56~7.49(5H, m) | |
60 | δ=9.08(1H, d), 8.84(1H, d), 8.69(2H, d), 8.45(1H, d), 8.36(2H, d), 8.20(1H, d), 8.17(1H, d), 8.05(1H, s), 7.96~7.85(6H, m), 7.70~7.49(10H, m) | |
62 | δ=9.08(1H, d), 8.84(1H, d), 8.69(2H, d), 8.45(1H, d), 8.36(2H, d), 8.27(1H, d), 8.20(1H, d), 8.05(1H, s), 7.96~7.85(8H, m), 7.70~7.49(10H, m), 7.25(2H, d) | |
65 | δ=9.11(1H, d), 8.70(1H, d), 8.45~8.36(9H, m), 8.20(1H, d), 7.94~7.85(6H, m), 7.70~7.49(12H, m) | |
71 | δ=8.69(2H, d), 8.55(1H, d), 8.45(1H, d), 8.36(2H, d), 8.24~8.19(4H, m), 7.96~7.85(6H, m), 7.70~7.49(10H, m), 7.35(1H, t), 7.16(1H, t) | |
72 | δ=9.09(1H, s), 8.69(2H, d), 8.55~8.45(3H, m), 8.24~7.85(13H, m), 7.70~7.49(9H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
75 | δ=9.02(1H, d), 8.95(1H, d), 8.55(1H, d), 8.45(2H, d), 8.36(2H, m), 8.24~8.19(4H, m), 7.96~7.84(7H, m), 7.70~7.46(12H, m), 7.35(1H, t), 7.25~7.16(4H, m) | |
78 | δ=8.69(2H, d), 8.55(1H, d), 8.45~8.38(3H, m), 8.20(1H, d), 7.96~7.85(8H, m), 7.75~7.70(5H, m), 7.61~7.41(8H, m) | |
80 | δ=8.97(1H, d), 8.69(2H, d), 8.45(2H, d), 8.25~8.10(5H, m), 8.00~7.85(9H, m), 7.77(1H, t), 7.59~7.49(6H, m) | |
82 | δ=8.55(1H, d), 8.45~8.33(6H, m), 8.20(1H, d), 7.96~7.85(7H, m), 7.73~7.70(3H, m), 7.61~7.49(8H, m), 7.25(2H, d) | |
84 | δ=8.97(2H, d), 8.68(1H, d), 8.55(1H, d), 8.45~8.29(5H, m), 8.20(1H, d), 7.94~7.85(5H, m), 7.70(2H, m), 7.59~7.49(9H, m) | |
87 | δ=8.69(2H, d), 8.45(1H, d), 8.36(2H, d), 8.20(1H, d), 8.03~7.76(10H, m), 7.56~7.31(8H, m) | |
93 | δ=8.45~8.33(6H, m), 8.20(1H, d), 8.08~7.85(8H, m), 7.73~7.70(2H, m), 7.54~7.46(7H, m), 7.39~7.25(4H, m) | |
98 | δ=9.02(1H, d), 8.95(1H, d), 8.69(2H, d), 8.45(1H, d), 8.36(2H, d), 8.20(1H, d), 8.08~8.06(2H, d), 7.98~7.84(6H, m), 7.70(1H, t), 7.51~7.25(13H, m) | |
100 | δ=8.45~8.33(6H, m), 8.20(1H, d), 8.08(1H, d), 7.98~7.85(6H, m), 7.73~7.49(12H, m), 7.39~7.31(2H, m) | |
106 | δ=9.60(1H, d), 9.27(1H, s), 9.09(1H, s), 8.69(2H, d), 8.49(1H, d), 8.45(1H, d), 8.33~8.30(2H, m), 8.20~7.85(10H, m), 7.70~7.49(11H, m) | |
114 | δ=9.02(1H, d), 8.95(1H, d), 8.45(2H, d), 8.36(2H, d), 8.20(1H, d), 8.09(1H, d), 7.94~7.89(10H, m), 7.56~7.38(9H, m), 7.28~7.25(3H, m), 1.69(6H, s) | |
116 | δ=8.69(2H, d), 8.45~8.36(4H, m), 8.20(1H, d), 8.00~7.85(8H, m), 7.73~7.49(11H, m), 7.38(1H, t), 7.28(1H, t), 1.69(6H, s) | |
122 | δ=9.11(1H, d), 8.70~8.69(3H, m), 8.46~8.36(6H, m), 8.20(1H, d), 7.96~7.85(8H, m), 7.75~7.49(11H, m) | |
125 | δ=9.09(1H, s), 9.09(1H, d), 8.84(1H, d), 8.69(2H, d), 8.49~8.45(2H, m), 8.27~7.85(14H, m), 7.70~7.49(9H, m), 7.25(2H, d) | |
127 | δ=8.69(2H, d), 8.55(1H, d), 8.45(1H, d), 8.36(2H, d), 8.19(1H, d), 7.96~7.88(10H, m), 7.58~7.49(9H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
130 | δ=9.09(1H, s), 8.69(2H, d), 8.55~8.45(3H, m), 8.24~7.88(12H, m), 7.68~7.49(10H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
135 | δ=9.02(1H, d), 8.95(1H, d), 8.55(1H, d), 8.45(2H, d), 8.36(2H, d), 8.19(1H, d), 7.97~7.88(11H, m), 7.58~7.49(11H, m), 7.35(1H, t), 7.25~7.16(4H, m) | |
137 | δ=8.45~8.33(7H, m), 8.12(1H, s), 7.99~7.88(6H, m), 7.73(1H, t), 7.56~7.49(9H, m) | |
140 | δ=8.69(2H, d), 8.55(1H, d), 8.45(2H, d), 8.36(2H, d), 7.96~7.85(9H, m), 7.70(1H, t), 7.46~7.49(9H, m), 7.25(2H, d) | |
141 | δ=8.55(1H, d), 8.45(2H, d), 8.36~8.33(4H, m), 7.96~7.88(7H, m), 7.73~7.70(2H, m), 7.56~7.49(10H, m), 7.25(2H, d) | |
144 | δ=8.97(2H, d), 8.68(1H, d), 8.55(1H, d), 8.45~8.29(5H, m), 7.97~7.88(5H, m), 7.70(1H, t), 7.59~7.49(11H, m) | |
146 | δ=9.02(1H, d), 8.95(1H, d), 8.55(1H, d), 8.45~8.32(8H, m), 8.06(1H, d), 7.93~7.84(5H, m), 7.73~7.70(2H, m), 7.56~7.46(11H, m) | |
150 | δ=8.97(1H, d), 8.69(2H, d), 8.45(1H, d), 8.25(1H, t), 8.15~8.10(2H, m), 8.00~7.82(8H, m), 7.69(1H, d), 7.57~7.31(10H, m) | |
152 | δ=8.69(2H, d), 8.45(1H, d), 8.36(2H, d), 7.98~7.82(9H, m), 7.69(1H, t), 7.57~7.49(9H, m), 7.39~7.25(4H, m) | |
155 | δ=8.97(2H, d), 8.68(1H, d), 8.45(1H, d), 8.36~8.29(3H, 22), 8.08(1H, d), 7.97~7.88(5H, m), 7.59~7.31(13H, m) | |
165 | δ=9.60(1H, d), 9.27(1H, s), 8.45(1H, d), 8.36~8.30(6H, m), 8.15(1H, d), 7.96~7.88(5H, m), 7.73~7.49(15H, m), 7.25(2H, d) | |
166 | δ=8.69(2H, d), 8.45(1H, d), 8.36(2H, d), 8.09(1H, d), 7.96~7.89(7H, m), 7.78(1H, d), 7.55~7.49(8H, m), 7.38(1H, t), 7.28(1H, t), 1.69(6H, s) | |
169 | δ=8.85(1H, d), 8.45~8.33(8H, m), 8.08(1H, d), 7.97~7.88(5H, m), 7.78~7.73(4H, m), 7.61~7.40(9H, m), 7.29(1H, t), 7.09(1H, d), 1.75(6H, s) | |
179 | δ=8.52~8.31(8H, m), 8.15~7.88(10H, m), 7.73~7.70(3H, m), 7.61~7.49(9H, m) | |
190 | δ=9.09(1H, s), 8.69(2H, d), 8.55~8.49(2H, d), 8.19~8.16(2H, m), 8.08~7.91(13H, m), 7.61~7.35(9H, m), 7.20~7.16(2H, m) | |
196 | δ=8.55(1H, d), 8.36~8.35(3H, m), 8.19(1H, d), 8.05(1H, d), 7.96~7.88(11H, m), 7.60~7.35(12H, m), 7.25~7.16(4H, m) | |
198 | δ=8.55(1H, d), 8.45~8.33(6H, m), 8.05(1H, d), 7.97~7.88(5H, m), 7.73~7.70(2H, m), 7.56~7.42(9H, m) | |
199 | δ=9.09(1H, s), 8.69(2H, d), 8.55~8.45(3H, m), 8.16~7.88(11H, m), 7.70~7.42(9H, m) | |
203 | δ=8.45(1H, d), 8.36~8.33(4H, m), 8.24~8.20(2H, d), 8.05~7.88(8H, m), 7.73(1H, t), 7.61~7.42(10H, m), 7.25(2H, d) | |
209 | δ=9.02(1H, d), 8.95(1H, d), 8.55(1H, d), 8.45~8.32(7H, m), 8.05(2H, d), 7.97~7.84(5H, m), 7.73~7.70(2H, m), 7.56~7.42(11H, m) | |
219 | δ=8.97(2H, d), 8.68(1H, d), 8.36~8.29(3H, m), 8.08~7.88(7H, m), 7.59~7.31(13H, m) | |
220 | δ=8.69(2H, d), 8.36(2H, d), 8.05~7.88(11H, m), 7.55~7.25(13H, m) | |
226 | δ=9.07(1H, s), 8.50(1H, d), 8.36~8.33(5H, m), 8.14(1H, d), 8.05~7.82(7H, m), 7.73~7.69(2H, m), 7.57~7.31(13H, m) | |
231 | δ=8.69(2H, d), 8.36(2H, d), 8.05(1H, d), 7.96~7.88(6H, m), 7.78(1H, d), 7.65(1H, d), 7.55~7.38(10H, m), 7.28(1H, t), 1.69(6H, s) | |
234 | δ=8.69(2H, d), 8.38(1H, d), 8.09~8.05(2H, d), 7.97~7.88(8H, m), 7.78~7.73(4H, m), 7.61~7.38(10H, m), 7.28(1H, t), 1.69(6H, s) | |
242 | δ=8.69(2H, d), 8.52(1H, d), 8.36~8.31(3H, m), 8.15~7.88(14H, m), 7.70(1H, d), 7.55~7.42(7H, m), 7.25(2H, d) | |
247 | δ=8.98(1H, d), 8.41~8.23(8H, m), 8.08~7.88(8H, m), 7.75~7.42(11H, m), 7.25(2H, d) | |
254 | δ=8.55(1H, d), 8.45(1H, d), 8.35~8.19(10H, m), 7.93~7.49(19H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
259 | δ=8.55(1H, d), 8.45(2H, d), 8.35~8.33(4H, m), 8.23(1H, s), 8.20(1H, d), 7.94~7.85(6H, m), 7.73~7.70(3H, m), 7.56~7.49(7H, m) | |
264 | δ=8.69(2H, d), 8.55(1H, d), 8.45(2H, d), 8.32~8.30(3H, m), 8.23~8.20(2H, d), 7.96~7.85(8H, m), 7.70(2H, t), 7.56~7.49(7H, m), 7.25(2H, d) | |
265 | δ=8.97(2H, d), 8.68(1H, d), 8.55(1H, d), 8.45(2H, d), 8.29~8.20(3H, m), 7.94~7.85(7H, m), 7.70(2H, t), 7.59~7.49(9H, m) | |
266 | δ=9.02(1H, d), 8.95(1H, d), 8.69(2H, d), 8.55(1H, d), 8.45(2H, d), 8.35~8.30(5H, m), 8.23~8.20(2H, m), 8.06(1H, d), 7.94~7.85(5H, m), 7.70(2H, t), 7.56~7.46(9H, m) | |
270 | δ=8.69(2H, d), 8.45(2H, d), 8.23(1H, s), 8.20(1H, d), 8.08~7.85(11H, m), 7.70~7.49(8H, m), 7.39~7.31(2H, m) | |
275 | δ=8.45(1H, d), 8.33(2H, d), 8.23(1H, s), 8.20(1H, d), 8.08~7.85(11H, m), 7.73~7.70(2H, m), 7.56~7.49(7H, m), 7.39~7.25(4H, m) | |
282 | δ=9.60(1H, d), 9.27(1H, s), 8.97(2H, d), 8.68(1H, d), 8.45(1H, d), 8.35~8.20(8H, m), 7.94~7.85(3H, m), 7.70~7.49(14H, m) | |
283 | δ=8.69(2H, d), 8.45(1H, d), 8.35~8.30(4H, m), 8.23~8.18(3H, m), 7.94~7.85(4H, m), 7.74~7.68(3H, m), 7.56~7.49(6H, m), 7.38(1H, t), 7.28(1H, t), 1.69(6H, s) | |
285 | δ=8.69(2H, d), 8.45(1H, d), 8.23(1H, s), 8.20(1H, d), 8.09(1H, d), 7.96~7.70(11H, m), 7.56~7.49(6H, m), 7.38(1H, t), 7.28(1H, t), 1.69(6H, s) | |
288 | δ=8.97(2H, d), 8.68(1H, d), 8.45(1H, d), 8.29(1H, d), 8.23(1H, s), 8.20(1H, d), 8.09(1H, d), 7.94~7.70(9H, m), 7.59~7.49(8H, m), 8.38(1H, t), 8.28(1H, t), 1.69(6H, s) | |
290 | δ=8.69(2H, d), 8.45(1H, d), 8.35~8.30(4H, m), 8.23(1H, s), 8.20(1H, d), 8.09(1H, d), 7.94~7.70(10H, m), 7.61~7.49(7H, m), 7.38(1H, t), 7.28(1H, t), 1.69(6H, s) | |
296 | δ=9.08(1H, d), 8.84(1H, d), 8.69(2H, d), 8.45(1H, d), 8.23(1H, s), 8.20~8.17(2H, m), 8.05(1H, s), 7.96~7.85(8H, m), 7.70~7.49(10H, m) | |
297 | δ=9.11(1H, d), 8.70(1H, d), 8.46~8.33(4H, m), 8.23~8.20(3H, m), 7.94~7.85(7H, m), 7.75~7.49(10H, m) | |
299 | δ=9.08(1H, d), 8.84(1H, d), 8.69(2H, d), 8.45(1H, d), 8.30~8.20(5H, m), 8.05(1H, s), 7.96~7.85(8H, m), 7.75~7.41(14H, m), 7.25(2H, d) | |
303 | δ=8.69(2H, d), 8.55(1H, d), 8.46(2H, d), 8.30~8.19(7H, m), 8.06~7.85(8H, m), 7.70~7.49(9H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
305 | δ=9.02(1H, d), 8.95(1H, d), 8.55(1H, d), 8.45(2H, d), 8.35~8.19(8H, m), 7.94~7.80(6H, m), 7.70~7.46(12H, m), 7.35(1H, t), 7.25~7.16(4H, m) | |
307 | δ=8.97(2H, d), 8.68(1H, d), 8.55(1H, d), 8.45(1H, d), 8.29~8.19(6H, m), 7.95~7.85(6H, m), 7.70~7.49(12H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
310 | δ=8.69(2H, d), 8.55(1H, d), 8.45(2H, d), 8.30(2H, d), 8.23(1H, s), 8.20(1H, d), 7.94~7.85(7H, m), 7.70(2H, m), 7.56~7.49(7H, m) | |
315 | δ=8.55(1H, d), 8.45(2H, d), 8.33~8.30(4H, m), 8.23(1H, s), 8.20(1H, d), 7.94~7.85(9H, m), 7.73~7.70(3H, m), 7.61~7.49(8H, m) | |
316 | δ=8.69(2H, d), 8.45(2H, d), 8.35~8.30(4H, m), 8.23(1H, s), 8.20(1H, d), 8.12(2H, d), 7.99~7.85(7H, m), 7.73~7.70(2H, m), 7.61~7.49(8H, m) | |
318 | δ=8.69(2H, d), 8.55(1H, d), 8.45(2H, d), 8.32~8.30(3H, m), 8.23(1H, s), 8.20(1H, d), 7.96~7.70(12H, m), 7.60~7.41(9H, m), 7.25(2H, d) | |
324 | δ=8.69(2H, d), 8.45(1H, d), 8.30(2H, d), 8.23(1H, s), 8,20(1H, d), 8.08(1H, d), 7.98~7.85(11H, m), 7.70(1H, t), 7.54~7.31(9H, m) | |
326 | δ=8.69(2H, d), 8.45(1H, d), 8.30(2H, d), 8.23(1H, s), 8.20(1H, d), 7.98~7.85(9H, m), 7.70~7.69(2H, m), 7.57~7.25(11H, m) | |
330 | δ=9.02(1H, d), 8.95(1H, d), 8.45(2H, m), 8.35(2H, d), 8.23(1H, s), 8.20(1H, d), 8.08(1H, d), 7.98~7.84(7H, m), 7.74~7.70(3H, m), 7.61~7.31(12H, m) | |
331 | δ=8.45(1H, d), 8.35~8.33(4H, m), 8.23(1H, s), 8.20(1H, d), 8.08(1H, d), 7.98~7.85(6H, m), 7.74~7.49(13H, m), 7.39~7.31(2H, m) | |
332 | δ=9.60(1H, d), 9.27(1H, s), 8.69(2H, d), 8.45(1H, d), 8.35~8.15(9H, m), 7.94~7.85(3H, m), 7.70~7.49(12H, m) | |
336 | δ=9.60(1H, d), 8.27(1H, s), 8.45(1H, d), 8.33~8.30(4H, m), 8.23(1H, s), 8.20~8.15(2H, m), 7.94~7.85(6H, m), 7.73~7.49(13H, m) | |
341 | δ=8.69(2H, d), 8.45(1H, d), 8.35~8.30(5H, m), 8.23(1H, s), 8.22~8.20(2H, m), 8.10~8.06(2H, m), 7.94~7.46(12H, m), 7.34(1H, d) | |
348 | δ=8.69(2H, d), 8.45(1H, d), 8.23(1H, s), 8.20(1H, d), 8.09(1H, d), 7.96~7.70(14H, m), 7.61~7.49(7H, m), 7.38(1H, t), 7.28(1H, t), 1.69 (6H, s) | |
350 | δ=8.69(2H, d), 8.52~8.45(2H, m), 8.35~8.08(12H, m), 7.94~7.85(4H, m), 7.70(2H, m), 7.56~7.49(5H, m) | |
359 | δ=9.11(1H, d), 8.70~8.69(3H, m), 8.46~8.43(3H, m), 8.23(1H, s), 8.20(1H, d), 7.96~7.41(26H, m) | |
362 | δ=8.69(2H, d), 8.55(1H, d), 8.45(1H, d), 8.23(1H, s), 8.19(1H, d), 7.97~7.88(12H, m), 7.58~7.49(9H, m), 7.35(1H, t), 7.20~7.16(1H, m) | |
363 | δ=8.55(1H, d), 8.45(1H, d), 8.35~8.33(4H, m), 8.23(1H, s), 8.19(1H, d), 7.94~7.88(9H, m), 7.73(1H, t), 7.58~7.49(9H, m), 7.35(1H, t), 8.20~7.16(2H, m) | |
364 | δ=8.69(2H, d), 8.55(1H, d), 8.46(2H, d), 8.30~8.19(6H, m), 8.06~7.88(8H, m), 7.68~7.49(10H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
366 | δ=8.97(2H, d), 8.68(1H, d), 8.55(1H, d), 8.45(1H, d), 8.29~8.19(5H, m), 7.94~7.88(6H, m), 7.68~7.49(13H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
370 | δ=8.55(1H, d), 8.45(2H, d), 8.35~8.33(4H, m), 8.23(1H, s), 7.94~7.88(6H, m), 7.73~7.70(2H, m), 7.56~7.49(9H, m) | |
371 | δ=8.97(2H, d), 8.68(1H, d), 8.55(1H, d), 8.45(1H, d), 8.29(1H, d), 8.23(1H, s), 7.97~7.88(7H, m), 7.70(1H, t), 7.59~7.49(11H, m) | |
373 | δ=8.69(2H, d), 8.55(1H, d), 8.45(2H, d), 8.35~8.23(8H, m), 7.97~7.88(4H, m), 7.70(1H, t), 7.58~7.49(9H, m), 7.25(2H, d) | |
375 | δ=9.02(1H, d), 8.95(1H, d), 8.45~8.33(5H, m), 8.24~8.17(4H, m), 8.06(1H, d), 7.94~7.84(7H, m), 7.73(1H, t), 7.56~7.46(11H, m) | |
382 | δ=8.69(2H, d), 8.45(1H, d), 8.30(2H, d), 8.23(1H, s), 8.08~7.88(10H, m), 7.56~7.25(13H, m) | |
385 | δ=9.02(1H, d), 8.95(1H, d), 8.69(2H, d), 8.45(1H, d), 8.23(1H, s), 8.08~7.88(12H, m), 7.55~7.31(13H, m) | |
386 | δ=8.97(2H, d), 8.68(1H, d), 8.45(1H, d), 8.29(1H, d), 8.23(1H, s), 8.03~7.76(9H, m), 7.59~7.31(12H, m) | |
391 | δ=9.60(1H, d), 9.27(1H, s), 8.69(2H, d), 8.45(1H, d), 8.33~8.23(5H, m), 8.15(1H, d), 7.97~7.88(5H, m), 7.70~7.49(13H, m) | |
393 | δ=9.60(1H, d), 9.27(1H, s), 8.45(1H, d), 8.35~8.33(6H, m), 8.23(1H, s), 8.15(1H, d), 7.94~7.88(4H, m), 7.73~7.49(14H, m) | |
396 | δ=8.69(2H, d), 8.45(1H, d), 8.30(2H, d), 8.23(1H, s), 8.09(1H, d), 7.97~7.88(7H, m), 7.78(1H, t), 7.56~7.49(8H, m), 7.38(1H, t), 7.28(1H, t), 1.69(6H, s) | |
408 | δ=8.97(2H, d), 8.68(1H, d), 8.52(1H, d), 8.45(1H, d), 8.31~8.23(3H, m), 8.15~7.88(11H, m), 7.70(1H, d), 7.59~7.49(9H, m) | |
416 | δ=8.97(2H, d), 8.68(1H, d), 8.55(1H, d), 8.29~8.19(5H, m), 8.05~7.88(7H, m), 7.68~7.35(14H, m), 7.20~7.16(2H, m) | |
419 | δ=8.69(2H, d), 8.55(1H, d), 8.45(1H, d), 8.35~8.30(4H, m), 8.05(1H, d), 7.97~7.88(5H, m), 7.70(1H, t), 7.56~7.42(9H, m) | |
422 | δ=8.45(1H, d), 8.33(2H, s), 8.23(1H, s), 8.05~7.88(10H, m), 7.73~7.68(2H, m), 7.56~7.42(9H, m) | |
424 | δ=8.55(1H, d), 8.45(1H, d), 8.33~8.30(4H, m), 8.23(1H, s), 8.05~7.85(10H, m), 7.73~7.70(2H, m), 7.61~7.42(10H, m) | |
431 | δ=8.69(2H, d), 8.30(2H, d), 8.23(1H, s), 8.08~7.88(9H, m), 7.55~7.31(11H, m) | |
432 | δ=8.69(2H, d), 8.35~8.23(5H, m), 8.05~7.82(6H, m), 7.69(1H, d), 7.57~7.42(11H, m) | |
441 | δ=8.95(1H, d), 8.69(2H, d), 8.23(1H, s), 8.20(1H, d), 8.12(1H, s), 8.05~7.71(13H, m), 7.55~7.31(12H, m) | |
443 | δ=8.97(2H, d), 8.68(1H, d), 8.35~8.23(4H, m), 8.05~7.82(6H, m), 7.69(1H, d), 7.59~7.31(13H, m) | |
445 | δ=9.60(1H, d), 9.27(1H, s), 8.69(2H, d), 8.33~8.23(5H, m), 8.15(1H, d), 8.05~7.88(6H, m), 7.70~7.42(13H, m) | |
450 | δ=8.93(1H, d), 8.69(2H, d), 8.35~8.23(6H, m), 8.05~7.88(6H, m), 7.74(1H, d), 7.57~7.38(11H, m), 1.75(6H, s) | |
452 | δ=8.69(2H, d), 8.30(2H, d), 8.23(1H, s), 8.09~8.05(2H, m), 7.97~7.88(7H, m), 7.78~7.73(4H, m), 7.61~7.38(10H, m), 7.28(1H, t), 1.69(6H, s) | |
456 | δ=8.97(2H, d), 8.68(1H, d), 8.52(1H, d), 8.31~8.23(3H, m), 8.08~7.88(12H, m), 7.70(1H, d), 7.59~7.42(9H, m) | |
460 | δ=9.08(1H, d), 9.02(1H, d), 8.95(1H, d), 8.84~8.79(2H, m), 8.69(2H, d), 8.23(1H, s), 8.06~7.88(12H, m), 7.70~7.42(13H, m) | |
462 | δ=8.69(6H, m), 8.55(1H, d), 8.45(2H, d), 8.32(1H, d), 8.20(3H, m), 7.94~7.85(4H, m), 7.75~7.70(4H, m), 7.56~7.41(7H, m), 7.25(2H, d) | |
465 | δ=8.69(2H, d), 8.45(1H, d), 8.29~8.28(3H, m), 8.20~8.17(4H, m), 8.09(1H, d), 7.94~7.85(6H, m), 7.70(1H, t), 7.56~7.49(6H, m), 7.38(1H, t), 7.28(1H, t), 1.69(6H, s) | |
467 | δ=8.69(2H, d), 8.55(1H, d), 8.45(1H, d), 8.30~8.19(8H, m), 7.94~7.85(8H, m), 7.70(1H, t), 7.58~7.49(7H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
471 | δ=9.11(1H, d), 8.97(2H, d), 8.70~8.68(3H, m), 8.46~8.43(3H< m), 8.29~8.20(5H, m), 7.94~7.85(6H, m), 7.73~7.49(14H, m) | |
476 | δ=8.69(4H, d), 8.29(2H, d), 8.20(2H, s), 8.08~7.88(7H, m), 7.55~7.31(11H, m) | |
479 | δ=8.97(1H, d), 8.69(2H, d), 8.55(1H, d), 8.25~8.10(5H, m), 8.00~7.85(10H, m), 7.70(1H, t), 7.59~7.50(5H, m), 7.39~7.31(3H, m), 7.20~7.16(2H, m) | |
480 | δ=8.69(2H, d), 8.55(1H, d), 8.19(1H, d), 7.96~7.85(14H, m), 7.70(1H, t), 7.60~7.31(11H, m), 7.20~7.16(2H, m) | |
486 | δ=8.69(2H, d), 8.55(1H, d), 8.38~8.36(3H, m), 8.24~8.19(4H, m), 7.98~7.85(7H, m), 7.73~7.50(11H, m), 7.39~7.31(3H, m), 7.20~7.16(2H, m) | |
488 | δ=8.55(1H, d), 8.38~8.33(5H, m), 8.20(1H, d), 7.94~7.85(9H, m), 7.73~7.70(3H, m), 7.61~7.50(8H, m), 7.39~7.31(3H, m), 7.20~7.16(2H, m) | |
493 | δ=9.02(1H, d), 8.95(1H, d), 8.69(2H, d), 8.55(1H, d), 8.45(1H, d), 8.36(2H, d), 8.20(1H, d), 8.06(1H, d), 7.98~7.84(6H, m), 7.70(2H, m), 7.56~7.25(12H, m) | |
498 | δ=8.69(2H, d), 8.55(1H, d), 8.45(1H, d), 8.36~8.32(3H, m), 8.20(1H, d), 7.96~7.85(8H, m), 7.70(2H, t), 7.56~7.49(6H, m), 7.39~7.25(4H, m) | |
499 | δ=8.97(2H, d), 8.68(1H, d), 8.55(1H, d), 8.45(1H, d), 8.36~8.29(3H, m), 8.20(1H, d), 7.98~7.85(5H, m), 7.70(2H, t), 7.56~7.31(10H, m) | |
502 | δ=8.69(2H, d), 8.36(2H, d), 8.20(1H, d), 8.08(1H, d), 7.98~7.85(7H, m), 7.70(1H, t), 7.54~7.50(6H, m), 7.39~7.31(4H, m) | |
506 | δ=8.97(2H, d), 8.68(1H, d), 8.36~8.29(3H, m), 8.20(1H, d), 7.98~7.82(5H, m), 7.70~7.69(2H, m), 7.59~7.50(8H, m), 7.39~7.31(4H, m) | |
508 | δ=8.69(2H, d), 8.36(2H, d), 8.20(1H, d), 8.08~7.94(9H, m), 7.85(1H, t), 7.70(1H, t), 7.54~7.70(6H, m), 7.39~7.25(6H, m) | |
511 | δ=9.02(1H, d), 8.95(1H, d), 8.69(2H, d), 8.36(2H, d), 8.20(1H, d), 8.08~7.94(8H, m), 7.84(2H, m), 7.70(1H, t), 7.54~7.31(12H, m) | |
517 | δ=8.36~8.33(4H, m), 8.20(1H, d), 8.08(1H, d), 7.98~7.85(7H, m), 7.73~7.70(2H, m), 7.61~7.50(7H, m), 7.39~7.25(6H, m) | |
519 | δ=9.60(1H, d), 9.27(1H, s), 8.36~8.30(7H, m), 8.20~8.15(2H, d), 7.98~7.94(2H, m), 7.85(1H, t), 7.73~7.64(6H, m), 7.54~7.50(6H, m), 7.39~7.31(2H, m) | |
524 | δ=8.36~8.33(5H, m), 8.20(1H, d), 8.09(1H, d), 7.98~7.70(8H, m), 7.55~7.50(5H, m), 7.39~7.28(4H, m), 1.69 (6H, s) | |
527 | δ=9.02(1H, d), 8.95(1H, d), 8.45(1H, d), 8.36(2H, d), 8.20(1H, d), 8.09(1H, d), 7.98~7.78(10H, m), 7.55~7.25(13H, m), 1.69(6H, s) | |
537 | δ=9.11(1H, d), 8.70(1H, d), 8.46(1H, s), 8.38~8.33(4H, m), 8.21~8.20(2H, m), 7.98~7.85(6H, m), 7.73~7.31(15H, m) | |
540 | δ=9.08(1H, d), 8.84(1H, d), 8.69(2H, d), 8.36~8.20(5H, m), 8.05~7.85(8H, m), 7.73~7.50(11H, m), 7.39~7.31(2H, m) | |
546 | δ=8.97(1H, d), 8.69(2H, d), 8.55(1H, d), 8.36(2H, d), 8.24~8.12(4H, m), 7.96~7.79(7H, m), 7.70(1H, t), 7.59~7.50(8H, m), 7.39~7.31(3H, m), 7.20~7.16(2H, m) | |
550 | δ=8.97(2H, d), 8.68(1H, d), 8.55(1H, d), 8.36~8.19(7H, m), 7.98~7.85(4H, m), 7.70~7.50(11H, m), 7.39~7.31(3H, m), 7.20~7.16(2H, m) | |
553 | δ=8.55(1H, d), 8.45~8.33(6H, m), 8.20(1H, d), 7.98~7.85(5H, m), 7.73~7.70(3H, m), 7.56~7.31(8H, m) | |
557 | δ=8.69(2H, d), 8.55(1H, d), 8.45(1H, d), 8.36(2H, d), 8.20(1H, d), 7.96~7.85(9H, m), 7.70(2H, t), 7.56~7.25(10H, m) | |
559 | δ=8.69(2H, d), 8.55(1H, d), 8.45(1H, d), 8.36~8.32(3H, m), 8.20(1H, d), 7.98~7.85(8H, m), 7.70(2H, m), 7.56~7.49(6H, m), 7.39~7.25(4H, m) | |
562 | δ=9.02(1H, d), 8.95(1H, d), 8.55(1H, d), 8.45~8.31(7H, m), 8.20(1H, d), 8.06(1H, d), 7.98~7.84(5H, m), 7.73~7.70(3H, m), 7.56~7.31(10H, m) | |
563 | δ=8.69(2H, d), 8.36(2H, d), 8.20(1H, d), 8.08(1H, d), .7.98~7.85(7H, m), 7.70(1H, t), 7.54~7.50(6H, m), 7.39~7.31(4H, m) | |
567 | δ=8.69(2H, d), 8.36(2H, d), 8.20(1H, d), 7.98~7.94(7H, m), 7.82(1H, d), 7.70~7.69(2H, m), 7.57~7.50(6H, m), 7.39~7.25(6H, m) | |
573 | δ=9.02(1H, d), 8.95(1H, d), 8.45(1H, d), 8.36(2H, d), 8.20(1H, d), 8.03~7.76(11H, m), 7.54~7.25(13H, m) | |
576 | δ=8.36~8.33(4H, m), 8.20(1H, d), 8.08(1H, d), 7.98~7.85(7H, m), 7.70~7.50(11H, m), 7.39~7.31(4H, m) | |
578 | δ=9.60(1H, d), 8.27(1H, s), 8.69(2H, d), 8.36~8.33(5H, m), 8.20(1H, d), 7.98~7.85(7H, m), 7.70~7.50(13H, m), 7.39~7.31(2H, m) | |
579 | δ=9.60(1H, d), 9.27(1H, s), 8.36~8.30(6H, m), 8.20~8.15(2H, m), 7.98~7.85(5H, m), 7.73~7.50(13H, m), 7.39~7.25(4H, m) | |
585 | δ=8.69(2H, d), 8.36(2H, d), 8.20(1H, d), 8.09(1H, d), 7.98~7.78(9H, m), 7.55~7.50(5H, m), 7.39~7.28(4H, m), 1.69(6H, s) | |
587 | δ=8.97(2H, d), 8.69(1H, d), 8.36~8.29(3H, m), 8.20(1H, d), 8.00~7.85(5H, m), 7.70~7.68(2H, m), 7.59~7.50(8H, m), 7.39~7.28(4H, m), 1.69(6H, s) | |
588 | δ=9.03(1H, d), 8.36~8.33(4H, m), 8.20~8.09(4H, m), 7.98~7.50(17H, m), 7.39~7.21(4H, m), 1.69(6H, s) | |
591 | δ=8.69(2H, d), 8.50(1H, d), 8.36~8.20(5H, m), 8.09~7.78(13H, m), 7.55~7.50(5H, m), 7.39~7.28(4H, m), 1.69(6H, s) | |
593 | δ=8.95(1H, d), 8.69(2H, d), 8.52~8.50(2H, m), 8.38~8.31(2H, m), 8.20~7.52(22H, m), 7.39~7.31(3H, m) | |
597 | δ=9.08(1H, d), 9.02(1H, d), 8.95(1H, d), 8.84(1H, d), 8.79(1H, d), 8.69(2H, d), 8.36(2H, d), 8.20(1H, d), 8.06~7.84(9H, m), 7.70~7.31(13H, m) | |
598 | δ=9.11(1H, d), 9.03(1H, d), 8.70~8.69(3H, m), 8.46~8.36(4H, m), 8.20~8.13(3H, m), 7.96~7.54(18H, m), 7.39~7.31(2H, m) | |
604 | δ=8.55(1H, d), 8.38~8.33(5H, m), 8.19(1H, d), 7.98~7.88(7H, m), 773(1H, t), 7.59~7.50(8H, m), 7.39~7.31(3H, m), 7.20~7.16(2H, m) | |
605 | δ=8.69(2H, d), 8.55(1H, d), 8.36(2H, d), 8.24~8.21(2H, m), 7.98~7.88(8H, m), 7.75~7.31(17H, m), 7.16(1H, t) | |
608 | δ=8.97(2H, d), 8.68(1H, d), 8.55(1H, d), 8.36~8.19(6H, m), 7.98~7.88(4H, m), 7.69~7.50(19H, m), 7.39~7.31(3H, m), 7.20~7.16(2H, m) | |
609 | δ=8.69(2H, d), 8.55(1H, d), 8.19(1H, d), 7.98~7.88(12H, m), 7.75(2H, d), 7.59~7.16(15H, m) | |
613 | δ=8.55(1H, d), 8.45~8.33(6H, m), 7.98~7.88(5H, m), 7.73~7.70(2H, m), 7.59~7.31(10H, m) | |
616 | δ=9.05(1H, d), 8.91(1H, d), 8.69(2H, d), 8.55~8.45(3H, m), 8.36(2H, d), 7.98~7.88(7H, m), 7.77~7.70(2H, m), 7.59~7.25(12H, m) | |
617 | δ=8.55(1H, d), 8.45(1H, d), 8.36~8.33(4H, m), 7.98~7.88(7H, m), 7.70~7.31(15H, m) | |
618 | δ=8.69(2H, d), 8.45(1H, d), 8.36(2H, d), 8.36~8.17(3H, m), 7.98~7.88(8H, m), 7.60~7.49(10H, m), 7.39~7.31(2H, m) | |
621 | δ=9.02(1H, d), 8.95(1H, d), 8.45~8.36(4H, m), 8.12(1H, s), 7.99~7.84(9H, m), 7.59~7.25(14H, m) | |
626 | δ=8.69(2H, d), 8.38(1H, d), 8.09~7.82(11H, m), 7.73~7.54(11H, m), 7.39~7.31(5H, m) | |
632 | δ=8.97(2H, d), 8.68(1H, d), 8.36~8.29(3H, dd), 7.98~7.82(5H, m), 7.69(1H, d), 7.59~7.50(10H, m), 7.39~7.31(4H, m) | |
638 | δ=9.60(1H, d), 9.27(1H, s), 8.69(2H, d), 8.36~8.30(4H, m), 8.15(1H, d), 7.98~7.88(5H, m), 7.70~7.50(12H, m), 7.35~7.31(2H, m) | |
641 | δ=9.60(1H, d), 9.27(1H, s), 8.36~8.30(6H, m), 8.15(1H, d), 7.98~7.96(5H, m), 7.70~7.50(16H, m), 7.39~7.31(2H, m) | |
645 | δ=8.38~8.33(5H, m), 7.98~7.88(6H, m), 7.73~7.28(17H, m), 1.69(6H, s) | |
650 | δ=9.03(1H, d), 8.69(2H, d), 8.36(2H, d), 8.14~8.13(2H, m), 7.98~7.78(8H, m), 7.65~7.28(15H, m), 1.69(6H, s) | |
653 | δ=8.97(2H, d), 8.68(1H, d), 8.38~8.29(6H, m), 8.19(2H, d), 8.08~7.88(9H, m), 7.73(1H, t), 7.61~7.50(9H, m), 7.39~7.31(2H, m) | |
661 | δ=9.02~8.95(3H, m), 8.69(2H, d), 8.41~8.23(5H, m), 8.08~7.90(9H, m), 7.68~7.31(13H, m) | |
663 | δ=9.27(1H, s), 9.08(1H, d), 8.52(1H, d), 8.38~8.27(6H, m), 8.15(1H, d), 8.05~31(20H, m) | |
664 | δ=8.69(2H, d), 8.55(1H, d), 8.36(2H, d), 7.99~7.88(11H, m), 7.77~7.65(5H, m), 7.55~7.35(10H, m), 7.22~7.16(2H, m) | |
666 | δ=9.09(1H, s), 8.69(2H, d), 8.55(1H, d), 8.49(1H, d), 8.19~8.16(2H, m), 8.08~7.88(11H, m), 7.70~7.50(8H, m), 7.36~7.35(2H, m), 7.22~7.16(3H, m) | |
667 | δ=8.55(1H, d), 8.38~8.33(3H, m), 8.19(1H, d), 7.96~7.88(9H, m), 7.79~7.35(16H, m), 7.22~7.16(3H, m) | |
668 | δ=8.69(2H, d), 8.55~8.54(2H, m), 8.36(2H, d), 8.24~8.21(2H, d), 7.99~7.88(6H, m), 7.70~7.54(13H, m), 7.36~7.35(2H, m), 7.20~7.16(2H, m) | |
671 | δ=9.02(1H, t), 8.95(1H, d), 8.55~8.45(3H, m), 8.36(2H, d), 8.12~8.11(2H, d), 7.97~7.84(10H, m), 7.72~7.65(4H, m), 7.57~7.46(8H, m), 7.36~7.35(2H, m), 7.25~7.16(4H, m) | |
674 | δ=8.45~8.33(6H, m), 8.03~7.88(5H, m), 7.73~7.49(11H, m), 7.36(1H, t), 7.22(1H, t) | |
680 | δ=8.55(1H, d), 8.45~8.33(6H, m), 7.97~7.88(5H, m), 7.73~7.49(14H, m), 7.36(1H, t), 7.22(1H, t) | |
681 | δ=8.69(2H, d), 8.55(1H, d), 8.45(1H, d), 8.36~8.32(3H, m), 7.96~7.88(7H, m), 7.70~7.65(3H, m), 7.56~7.49(7H, m), 7.36(1H, t), 7.25~7.22(3H, m) | |
682 | δ=8.97(2H, d), 8.68(1H, d), 8.55~8.54(2H, d), 8.36~8.29(3H, m), 7.99~7.50(18H, m), 7.36(1H, t), 7.22(1H, t) | |
687 | δ=8.38~8.33(5H, m), 8.16~8.08(3H, m), 7.97(1H, d), 7.88~7.84(3H, m), 7.73~7.65(5H, m), 7.55~7.48(7H, m), 7.36(1H, t), 7.22(1H, t) | |
691 | δ=8.97(1H, d), 8.38~8.25(4H, m), 8.15~8.10(2H, m), 8.00~7.82(5H, m), 7.73~7.52(10H, m), 7.39~7.22(4H, m) | |
696 | δ=8.69(2H, d), 8.36(2H, d), 8.08(1H, d), 7.98~7.88(6H, m), 7.70~7.50(11H, m), 7.39~7.22(6H, m) | |
699 | δ=8.95(2H, d), 8.45~8.36(4H, m), 8.08(1H, d), 7.98~7.84(6H, m), 7.73~7.22(1-7H, m) | |
700 | δ=8.36~8.33(4H, m), 8.08(1H, d), 7.98~7.88(6H, m), 7.70~7.50(13H, m), 7.39~7.22(4H, m) | |
703 | δ=9.60(1H, d), 9.27(1H, s), 8.69(2H, d), 8.36~8.30(4H, m), 8.15(1H, d), 7.96~7.88(4H, m), 7.70~7.50(13H, m), 7.36(1H, t), 7.22(1H, t) | |
712 | δ=8.69(2H, d), 8.38~8.36(3H, m), 8.09(1H, d), 7.96~7.88(7H, m), 7.73~7.50(11H, m), 7.38~7.22(4H, m) | |
721 | δ=9.02(2H, d), 8.95(2H, d), 8.52~8.45(2H, m), 8.36~8.31(3H, m), 8.15~7.88(11H, m), 7.70~7.65(3H, m), 7.55~7.36(10H, m), 7.22(1H, t) | |
722 | δ=9.08(1H, d), 8.84(1H, d), 8.69(2H, d), 8.36(2H, d), 8.27(1H, d), 8.05(1H, s), 7.97~7.88(7H, m), 7.70~7.50(11H, m), 7.36(1H, t), 7.25~7.22(3H, m) | |
724 | δ=9.08(1H, d), 8.84~8.79(2H, m), 8.50(1H, d), 8.36~8.23(7H, m), 8.09~7.88(6H, m), 7.77~7.50(13H, m), 7.36(1H, t), 7.22(1H, t) | |
725 | δ=8.69(2H, d), 8.55(1H, d), 8.35~8.30(4H, m), 8.23(1H, s), 8.20(1H, d), 7.98~7.85(8H, m), 7.70(1H, t), 7.58~7.50(6H, m), 7.39~7.31(3H, m), 7.20~7.16(2H, m) | |
727 | δ=8.69(2H, d), 8.55(1H, d), 8.30(2H, d), 8.23(1H, s), 8.19(1H, d), 7.98~7.80(9H, m), 7.70(1H, t), 7.58~7.31(10H, m), 7.20~7.16(2H, m) | |
731 | δ=8.97(2H, d), 8.68(1H, d), 8.55(1H, d), 8.29(1H, d), 8.23(1H, s), 8.20~2.19(2H, m), 7.98~7.85(10H, m), 7.70(1H, t), 7.59~7.49(8H, m), 7.39~7.31(2H, m), 7.20~7.16(2H, m) | |
736 | δ=8.69(2H, d), 8.55(1H, d), 8.45(1H, d), 8.35~8.30(4H, m), 8.23(1H, s), 8.20(1H, d), 7.98~7.85(9H, m), 7.70(2H, m), 7.56~7.50(6H, m), 7.39~7.31(2H, m) | |
737 | δ=8.55(1H, d), 8.45(1H, d), 8.35~8.33(4H, m), 8.23(1H, s), 8.20(1H, d), 7.96~7.85(7H, m), 7.73~7.31(14H, m) | |
740 | δ=8.69(2H, d), 8.55(1H, d), 8.45(1H, d), 8.32~8.30(3H, m), 8.23(1H, s), 8.20(1H, d), 7.98~7.85(8H, m), 7.70(2H, m), 7.56~7.25(10H, m) | |
742 | δ=8.71~8.69(3H, m), 8.55~8.45(3H, m), 8.35~8.09(9H, m), 7.98~7.85(4H, m), 7.70~7.31(12H, m) | |
748 | δ=8.69(2H, d), 8.35~7.20(6H, m), 7.98~7.94(3H, m), 7.85~7.82(2H, m), 7.70~7.69(2H, m), 7.57~7.50(6H, m), 7.39~7.31(4H, m) | |
750 | δ=8.97(1H, d), 8.69(2H, d), 8.30~8.10(7H, m), 8.00~7.82(6H, m), 7.70~7,69(2H, m), 7.59~7.52(5H, m), 7.39~7.31(4H, m) | |
751 | δ=8.38~8.20(7H, m), 8.08~7.85(8H, m), 7.73~7.70(2H, m), 7.55~7.31(12H, m) | |
753 | δ=8.33(2H, d), 8.23(1H, s), 8.20(1H, d), 8.02~7.85(11H, m), 7.75~7.70(5H, m), 7.61~7.25(13H, m) | |
754 | δ=9.60(1H, d), 9.27(1H, s), 8.69(2H, d), 8.33~8.30(2H, m), 8.23(1H, s), 820~8.15(2H, d), 7.98~7.85(7H, m), 7.70~7.31(13H, m) | |
757 | δ=9.60(1H, d), 9.27(1H, s), 8.35~8.30(6H, m), 8.23(1H, s), 8.20~8.15(2H, d), 7.98~7.85(4H, m), 7.73~7.64(6H, m), 7.54~7.50(6H, m), 7.39~7.31(2H, m) | |
763 | δ=9.02(1H, d), 8.95(1H, d), 8.69(2H, d), 8.35(2H, d) 8.30(2H, d), 8.23(1H, s), 8.20(1H, d), 8.09~8.06(2H, m), 7.98~7.70(8H, m), 7.54~7.28(11H, m), 1.69(6H, s) | |
764 | δ=8.97(2H, d), 8.68(1H, d), 8.29(1H, d), 8.23(1H, s), 8.20(1H, d), 8.09(1H, d), 7.98~7.70(9H, m), 7.59~7.49(7H, m), 7.39~7.28(4H, m), 1.69(6H, s) | |
765 | δ=9.03(1H, d), 8.97(2H, d), 8.68(1H, d), 8.35~8.09(8H, m), 7.98~7.70(8H, m), 7.60~7.50(9H, m), 7.39~7.28(4H, m), 1.69(6H, s) | |
768 | δ=8.69(2H, d), 8.52(1H, d), 8.31(1H, d), 8.23~7.85(15H, m), 7.70(2H, m), 7.55~7.49(4H, m), 7.39~7.31(2H, m) | |
774 | δ=9.08(1H, d), 9.02(1H, d), 8.95(1H, d), 8.84~8.79(2H, m), 8.69(2H, d), 8.30~8.20(4H, m), 8.06~7.84(9H, m), 7.70~7.31(13H, m) | |
777 | δ=8.69(2H, d), 8.55(1H, d), 8.35~8.11(11H, m), 7.98~7.70(6H, m), 7.60~7.50(7H, m), 7.39~7.31(3H, m), 7.20~7.16(2H, m) | |
778 | δ=8.69(2H, d), 8.55(1H, d), 8.23(1H, s), 8.20~8.19(2H, m), 7.98~7.85(11H, m), 7.70(1H, t), 7.58~7.49(6H, m), 7.39~7.31(3H, m), 7.20~7.16(2H, m) | |
780 | δ=8.69(2H, d), 8.55(1H, d), 8.30~8.20(6H, m), 7.98~7.31(24H, m), 7.16(1H, t) | |
782 | δ=8.97(2H, d), 8.68(1H, d), 8.55(1H, d), 8.29~8.19(4H, m), 7.98~7.85(10H, m), 7.70(1H, t), 7.59~7.49(8H, m), 7.39~7.31(3H, m), 7.20~7.16(2H, m) | |
784 | δ=8.60(1H, s), 8.55(1H, d), 8.33(2H, d), 8.23(1H, s), 8.20~8.19(2H, d), 8.11(1H, d), 8.03~7.85(9H, m), 7.73~7.49(10H, m), 7.39~7.31(3H, m), 7.20~7.16(2H, m) | |
786 | δ=8.69(2H, d), 8.45(1H, d), 8.30(2H, d), 8.23(1H, s), 8.20(1H, d), 8.12(1H, s), 7.99~7.85(8H, m), 7.70(1H, t), 7.56~7.31(8H, m) | |
788 | δ=8.55(1H, d), 8.45(1H, d), 8.35~8.33(4H, m), 8.23(1H, s), 8.20(1H, d), 7.98~7.85(6H, m), 7.73~7.70(3H, m), 7.56~7.31(8H, m) | |
789 | δ=9.09(1H, s), 8.69(2H, d), 8.55~8.45(3H, m), 8.30~7.85(12H, m), 7.70~7.31(9H, m) | |
796 | δ=9.02(1H, d), 8.95(1H, d), 8.55(1H, d), 8.45~8.32(5H, m), 8.23(1H, s), 8.20(1H, d), 8.06~7.85(8H, m), 7.73~7.70(3H, m), 7.56~7.31(10H, m) | |
798 | δ=8.69(2H, d), 8.23(1H, s), 8.20(1H, d), 8.08(1H, d), 7.98~7.85(8H, m), 7.74~7.70(2H, m), 7.55~7.31(10H, m) | |
803 | δ=8.69(2H, d), 8.23(1H, s), 8.20(1H, d), 8.08~7.85(12H, m), 7.73~7.70(2H, m), 7.61~7.49(7H, m), 7.39~7.31(4H, m) | |
811 | δ=9.27(1H, s), 8.97(2H, d), 8.68(1H, d), 8.33~8.15(6H, m), 7.98~7.85(5H, m), 7.70~7.31(15H, m) | |
816 | δ=8.69(2H, d), 8.30(2H, d), 8.23(1H, s), 8.20(1H, d), 8.09(1H, d), 7.98~7.70(9H, m), 7.55~7.49(5H, m), 7.39~7.29(4H, m), 1.69(6H, s) | |
818 | δ=8.38~8.33(3H, m), 8.23(1H, s), 8.20(1H, d), 8.09(1H, d), 7.98~7.70(10H, m), 7.55~7.49(5H, m), 7.39~7.28(4H, m), 1.69(6H, s) | |
820 | δ=8.97(2H, d), 8.68(1H, d), 8.29(1H, d), 8.23(1H, s), 8.20(1H, d), 8.09(1H, d), 7.98~7.70(9H, m), 7.59~7.49(7H, m), 7.39~7.28(4H< m), 1.69(6H, s) | |
824 | δ=8.95(1H, d), 8.69(2H, d), 8.23(1H, s), 8.20(2H, d), 8.12(1H, s), 8.09(1H, d), 7.98~7.71(12H, m), 7.55~7.28(11H, m), 1.69(6H, s) | |
829 | δ=9.02(1H, d), 8.96(1H, d), 8.52~8.45(2H, m), 8.31~7.84(17H, m), 7.70(2H, m), 7.55~7.25(10H, m) | |
830 | δ=9.08(1H, d), 8.84(1H, d), 8.69(2H, d), 8.30~8.20(5H, m), 8.05~7.85(9H, m), 7.70~7.25(13H, m) | |
833 | δ=9.11(1H, d), 8.97(2H, d), 8.70~8.68(2H, m), 8.46~8.20(7H, m), 7.98~7.85(7H, m), 7.75~7.50(12H, m), 7.39~7.31(2H, m) | |
836 | δ=8.69(2H, d), 8.55(1H, d), 8.30(2H, d), 8.23(1H, s), 8.19(1H, d), 7.98~7.88(10H, m), 7.59~7.49(8H, m), 7.39~7.31(3H, m), 7.20~7.16(2H, m) | |
837 | δ=8.69(2H, d), 8.55(1H, d), 8.35~8.30(4H, m), 8.23(1H, s), 8.19(1H, d), 7.98~7.88(8H, m), 7.59~7.50(8H, m), 7.39~7.31(3H< m), 7.20~7.16(2H, m) | |
839 | δ=8.97(1H, d), 8.55(1H, d), 8.33(2H, m), 8.25~8.10(5H, m), 8.00~7.88(10H, m), 7.73(1H, t), 7.59~7.50(7H, m), 7.39~7.31(3H, m), 7.20~7.16(2H, m) | |
844 | δ=8.69(2H, d), 8.55(1H, d), 8.45(1H, d), 8.30(2H, d), 8.23(1H, s), 7.98~7.88(7H, m), 7.70(1H, t), 7.59~7.31(10H, m) | |
846 | δ=8.55(2H, d), 8.35~8.32(5H, m), 8.23(1H, s), 7.98~7.88(5H, m), 7.73~7.70(2H, m), 7.59~7.31(13H, m) | |
848 | δ=8.55(1H, d), 8.45(1H, d), 8.33~8,30(4H, m), 8.23(1H, s), 7.98~7.85(9H, m), 7.73~7.70(2H, m), 7.59~7.31(11H, m) | |
852 | δ=9.11(1H, s), 9.02(1H, d), 8.95(1H, d), 8.55(1H, d), 8.45(2H, d), 7.98~7.80(10H, m), 7.70~7.31(15H, m) | |
854 | δ=8.69(2H, d), 8.30(2H, d), 8.23(1H, s), 8.08(1H, d), 7.98~7.88(7H, m), 7.59~7.31(12H, m) | |
856 | δ=8.69(2H, d), 8.30(2H, d), 8.23(1H, s), 7.98~7.82(7H, m), 7.69(1H, d), 7.59~7.31(12H, m) | |
864 | δ=9.02(1H, d), 8.95(1H, d), 8.69(2H, d), 8.35(2H, d), 8.23(1H, s), 8.08~7.97(5H, m), 7.888~7.84(2H, m), 7.74(1H, d), 7.59~7.25(16H, m) | |
865 | δ=9.02(1H, d), 8.95(1H, d), 8.45(1H, d), 8.35(2H, d), 8.23(1H, s), 8.08(1H, d), 7.98~7.84(7H, m), 7.74~7.73(2H, m), 7.61~7.31(15H, m) | |
866 | δ=8.95(1H, d), 8.35~8.33(4H, m), 8.23(1H, s), 8.20(1H, d), 8.12~8.08(2H, m), 7.98~7.97(3H, m), 7.88(1H, d), 7.74~7.71(3H, m), 7.61~7.50(10H, m), 7.39~7.31(5H, m) | |
867 | δ=9.60(1H, d), 9.27(1H, s), 8.69(2H, d), 8.33~8.23(5H, m), 8.15(1H, d), 7.98~7.88(5H, m), 7.70~7.31(14H, m) | |
874 | δ=8.46(1H, s), 8.33(2H, d), 8.23(1H, s), 8.09~7.88(11H, m), 7.78~7.73(2H, m), 7.61~7.54(6H, m), 7.39~7.28(4H, m), 1.69(6H, s) | |
876 | δ=8.35(2H, d), 8.33(2H, m), 8.23(1H, s), 8.09(1H, d), 7.98~7.88(8H, m), 7.78~7.73(3H, m), 7.61~7.50(8H, m), 7.39~7.28(4H, m), 1.69(6H, s) | |
879 | δ=8.97(2H, d), 8.68(1H, d), 8.29(1H, d), 8.23(1H, s), 8.09(1H, d), 7.98~7.88(9H, m), 7.18(1H, d), 7.60~7.49(11H, m), 7.39~7.28(4H, m), 1.69(6H, s) | |
880 | δ=8.52(1H, d), 8.35~8.31(5H, m), 8.23(1H, s), 8.15~7.88(10H, m), 7.73~7.70(2H, m), 7.59~7.50(6H, m), 7.39~7.31(2H, m) | |
882 | δ=8.69(2H, d), 8.52(1H, d), 8.35~8.23(8H, m), 8.15~7.88(9H, m), 7.70(1H, d), 7.59~7.50(6H, m), 7.39~7.25(4H, m) | |
885 | δ=9.08(1H, d), 8.84~8.79(2H, d), 8.35~8.33(4H, m), 8.23(1H, s), 8.05~7.88(8H, m), 7.73~7.50(13H, m), 7.39~7.31(2H, m) | |
886 | δ=9.11(1H, d), 8.70(1H, d), 8.46~8.23(8H, m), 7.98~7.88(9H, m), 7.75~7.31(12H, m) | |
888 | 8.69(2H, d), 8.55(1H, d), 8.23(1H, s), 8.19(1H, d), 7.97~7.88(11H, m), 7.70~7.49(9H, m), 7.35(2H, m), 7.22~7.16(3H, m) | |
889 | δ=8.69(2H, d), 8.55(1H, d), 8.30~8.19(6H, m), 7.97~7.88(5H, m), 7.70~7.49(11H, m), 7.36~7.35(2H, m), 7.22~7.16(3H, m) | |
894 | δ=9.02(1H, d), 8.95(1H, d), 8.55(1H, d), 8.45(1H, d), 8.35~8.30(4H, m), 8.23(1H, s), 8.19(1H, d), 7.97~7.80(7H, m), 7.65~7.35(14H, m), 7.25~7.16(5H, m) | |
897 | δ=8.69(2H, d), 8.55(2H, d), 8.46(1H, s), 8.32~8.23(5H, m), 8.06~7.88(6H, m), 7.70~7.36(14H, m), 7.22(1H, t) | |
898 | δ=8.55(1H, d), 8.45(1H, d), 8.33(2H, d), 8.23(1H, s), 7.97~7.88(7H, m), 7.73~7.49(11H, m), 7.36(1H, t), 7.22(1H, t) | |
902 | δ=8.69(2H, d), 8.55(1H, d), 8.45(1H, d), 8.35~8.23(6H, m), 7.97~7.88(5H, m), 7.70~7.49(12H, m), 7.36(1H, t), 7.22(1H, t) | |
903 | δ=8.97(2H, d), 8.68(1H, d), 8.55(1H, d), 8.45(1H, d), 8.29(1H, d), 8.23(1H, s), 7.97~7.88(6H, m), 7.70~7.49(12H, m), 7.36(1H, t), 7.22(1H, t) | |
905 | δ=8.55(1H, d), 8.45(1H, d), 8.33~8.32(3H, m), 8.23(1H, s), 7.97~7.88(8H, m), 7.73~7.65(4H, m), 7.56~7.49(7H, m), 7.36(1H, t), 7.25~7.22(3H, m) | |
906 | δ=8.69(2H, d), 8.35~8.30(4H, m), 7.98~7.87(5H, m), 7.75~7.65(4H, m), 7.55~7.22(13H, m) | |
907 | δ=8.69(2H, d), 8.30(2H, d), 8.23(1H, s), 8.08~7.88(8H, m), 7.70~7.65(2H, m), 7.56~7.36(13H, m), 7.22(1H, t) | |
913 | δ=8.97(2H, d), 8.68(1H, d), 8.29(1H, d), 8.23(1H, s), 8.08(1H, d), 7.98~7.88(6H, m), 7.70~7.22(15H, m) | |
916 | δ=8.38~8.30(5H, m), 8.23(1H, s), 8.08~7.88(7H, m), 7.73~7.65(3H, m), 7.55~7.49(7H, m), 7.36~7.22(6H, m) | |
917 | δ=9.02(1H, d), 8.95(1H, d), 8.69(2H, d), 8.23(1H, s), 8.08~7.88(11H, m), 7.70~7.65(2H, m), 7.55~7.22(13H, m) | |
920 | δ=8.52(1H, s), 8.35~8.33(4H, m), 8.23(1H, s), 8.00~7.82(8H, m), 7.73~7.50(12H, m), 7.39~7.22(5H, m) | |
930 | δ=8.69(2H, d), 8.35~8.30(4H, m), 8.23(1H, s), 8.09(1H, d), 7.97~7.88(5H, m), 7.78~7.50(11H, m), 7.38~7.21(4H, m), 1.69(6H, s) | |
931 | δ=8.69(2H, d), 8.52(1H, d), 8.31(1H, d), 8.23(1H, s), 8.15~7.88(12H, m), 7.70~7.65(3H, m), 7.55~7.49(5H, m), 7.36(1H, t), 7.22(1H, t) | |
935 | δ=9.11(1H, d), 9.02(1H, d), 8.95(1H, d), 8.70(1H, d), 8.46~7.33(6H, m), 8.23(1H, s), 8.06(1H, d), 7.94~7.84(6H, m), 7.75~7.36(14H, m), 7.22(1H, t) | |
936 | δ=8.69(4H, m), 8.55(1H, d), 8.30(2H, d), 8.20~8.19(4H, m), 7.98~7.85(6H, m), 7.75~7.70(3H, m), 7.58~7.31(9H, m), 7.20~7.16(2H, m) | |
938 | δ=8.69(4H, m), 8.29(2H, d), 8.20(3H, m), 8.08~7.85(8H, m), 7.70(1H, t), 7.55~7.25(12H, m) | |
943 | δ=8.69(4H, m), 8.55(1H, d), 8.45(1H, d), 8.32~8.20(6H, m), 7.98~7.85(6H, m), 7.70(2H, t), 7.55~7.25(10H, m) | |
948 | δ=8.69(2H, d), 8.29~8.28(3H, m), 8.20~8.17(3H, m), 8.09(1H, d), 7.98~7.85(6H, m), 7.59~7.49(7H, m), 7.39~7.28(4H, m), 1.69(6H, s) | |
949 | δ=8.69(4H, m), 8.55(1H, d), 8.30(2H, d), 8.20~8.19(3H, m), 7.97~7.88(5H, m), 7.75~7.35(13H, m), 7.22~7.16(3H, m) | |
953 | δ=8.55(1H, d), 8.36(2H, d), 8.24~8.12(7H, m), 7.99~7.85(5H, m), 7.70~7.49(11H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
956 | δ=8.88(1H, s), 8.55(1H, d), 8.45~8.36(3H, m), 8.20(1H, d), 8.06~7.85(10H, m), 7.70~7.49(9H, m) | |
960 | δ=9.02(2H, d), 8.95(2H, d), 8.55(1H, d), 8.45(1H, d), 8.36(2H, m), 8.20~7.85(12H, m), 7.70~7.49(12H, m) | |
962 | δ=8.36(2H, d), 8.20(3H, m), 8.12(1H, s), 7.99~7.82(6H, m), 7.70~7.39(12H, m) | |
966 | δ=8.36(2H, d), 8.20~8.12(5H, m), 7.99~7.94(5H, m), 7.85~7.82(2H, m), 7.70~7.39(14H, m) | |
969 | δ=8.36(2H, d), 8.19(3H, m), 8.12(1H, s), 8.09(1H, s), 7.99~7.65(10H, m), 7.55~7.49(5H, m), 7.38(1H, t), 7.28(1H, t), 1.69(6H, s) | |
973 | 9.08(1H, d), 8.84(1H, d), 8.36~8.12(7H, m), 8.05~7.85(8H, m), 7.70~7,63(7H, m), 7.50~7.49(3H, m), 7.25(2H, d) | |
975 | 8.55(1H, d), 8.35(2H, m), 8.23~8.12(7H, m), 7.99~7.80(6H, m), 7.70~7.50(11H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
981 | 8.85(1H, s), 8.55(1H, d), 8.45~8.35(4H, m), 8.23(1H, s), 8.20(1H, d), 8.12~7.85(10H, m), 7.70~7.49(9H, m) | |
984 | 8.55(1H, d), 8.45(1H, d), 8.23~8.12(5H, m), 7.99~7.85(8H, m), 7.70~7.49(10H, m) | |
986 | 8.55(1H, d), 8.45(1H, d), 8.32~8.12(8H, m), 7.99~7.85(7H, m), 7.70~7.49(10H, m), 7.25(2H, d) | |
989 | 8.55(1H, d), 8.45(1H, d), 8.35~8.12(10H, m), 7.99~7.85(7H, m), 7.70~7.49(10H, m) | |
991 | 8.23~8.08(6H, m), 7.99~7.85(8H, m), 7.70~7.31(11H, m) | |
996 | 8.35(2H, d), 8.23~8.08(6H, m), 7.99~7.85(5H, m), 7.74~7.65(4H, m), 7.54~7.49(6H, m), 7.39~7.31(2H, m) | |
1003 | 8.23~8.19(4H, m), 8.12~8.09(2H, m), 7.99~7.65(12H, m), 7.55~7.49(5H, m), 7.38(1H, t), 7.28(1H, t) | |
1007 | 8.35~8.30(4H, m), 8.23(1H, s), 8.20~8.09(6H, m), 7.99~7.65(11H, m), 7.55~7.49(5H, m), 7.38(1H, t), 7.28(1H, t), 1.69(6H, s) | |
1013 | 9.11(1H, d), 8.70(1H, d), 8.46(1H, s), 8.23~8.12(6H, m), 7.99~7.85(8H, m), 7.75~7.49(10H, m) | |
1014 | 9.08(1H, d), 8.84(1H, d), 8.35~8.12(10H, m), 8.05~7.85(6H, m), 7.70~7.63(7H, m), 7.50~7.49(4H, m), 7.25(2H, d) | |
1020 | 8.36(4H, m), 8.20~8.19(3H, m), 7.96~7.79(7H, m), 7.70~7.65(3H, m), 7.50~7.49(7H, m), 7.25(2H, d) | |
1021 | 8.35~8.30(4H, m), 8.23(1H, s), 8.20~8.19(3H, m), 7.94~7.79(9H, m), 7.70~7.49(10H, m) | |
1026 | 8.38~8.36(3H, m), 8.23~8.20(3H, m), 8.12(2H, m), 7.99~7.94(5H, m), 7.85(1H, t), 7.75~7.70(4H, m), 7.61~7.41(10H, m), 7.24(2H, m) | |
1027 | 8.38(1H, d), 8.23~8.20(4H, m), 7.94~7.70(15H, m), 7.61~7.41(11H, m) | |
1030 | 8.36(2H, d), 8.20~8.12(5H, m), 7.99~7.94(6H, m), 7.85(1H, t), 7.75~7.65(5H, m), 7.50~7.41(7H, m), 7.25(4H, m) | |
1031 | 8.35~8.12(10H, m), 7.99~7.41(21H, m) | |
1033 | 8.38~8.12(9H, m), 7.99~7.85(8H, m), 7.75~7.49(14H, m) | |
1034 | 8.38~8.36(5H, m), 8.23~8.20(3H, m), 8.12(2H, m), 7.99~7.94(3H, m), 7.85(1H, t), 7.73~7.70(2H, m), 7.61~7.49(10H, m) | |
1035 | 8.35(2H, d), 8.23~8.20(4H, m), 7.94~7.73(11H, m), 7.61~7.4910H, m) | |
1036 | 8.55(1H, d), 8.36(2H, d), 8.20~8.19(4H, m), 7.94~7.83(10H, m), 7.70~7.50(9H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
1039 | 8.55(1H, d), 8.45(1H, d), 8.36(2H, d), 8.20~8.19(3H, m), 7.94~7.79(7H, m), 7.70~7.49(10H, m) | |
1041 | 8.97(1H, d), 8.55~8.45(3H, m), 8.36(2H, m), 8.25~8.15(3H, m), 8.00~7.79(8H, m), 7.70(2H, t), 7.59~7.49(7H, m) | |
1042 | 8.55(1H, d), 8.45(1H, d), 8.36~8.32(3H, m), 8.20~8.19(3H, m), 7.96~7.79(8H, m), 7.70~7.49(10H, m), 7.25(2H, d) | |
1044 | 9.02(1H, d), 8.95(1H, d), 8.55(1H, d), 8.45(1H, d), 8.36(2H, d), 8.20(3H, m), 8.06(1H, d), 7.94~7.79(8H, m), 7.70~7.49(12H, m) | |
1046 | 8.36(2H, d), 8.20~8.19(3H, m), 7.98~7.79(7H, m), 7.70~7.39(12H, m) | |
1049 | 8.36(2H, d), 8.20~8.19(3H, m), 7.98~7.82(9H, m), 7.70~7.39(14H, m) | |
1052 | 8.36(2H, d), 8.20~8.19(3H, m), 8.09(1H, d), 7.90~7.65(11H, m), 7.55~7.49(5H, m), 7.38(1H, t), 7.28(1H, t), 1.69(6H, s) | |
1053 | 9.08(1H, d), 8.84(1H, d), 8.36(2H, d), 8.20~8.17(4H, m), 8.05(1H, s), 7.90~7.62(13H, m), 7.50~7.49(4H, m) | |
1057 | 8.55(1H, d), 8.35(2H, d), 8.23(1H, s), 8.23(1H, s), 8.20~8.19(4H, m), 7.94~7.79(7H, m), 7.70~7.49(11H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
1058 | 8.55(1H, d), 8.24~8.19(7H, m), 7.94~7.79(8H, m), 7.70~7.49(11H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
1061 | 8.55(1H, d), 8.45(1H, d), 8.35~8.30(4H, m), 8.23(1H, s), 8.20~8.19(3H, m), 7.94~7.79(9H, m), 7.70~7.49(10H, m) | |
1065 | 8.85(1H, s), 8.37~8.35(3H, m), 8.23(1H, s), 8.20(1H, d), 8.06~7.50(20H, m), 7.39~7.31(2H, m) | |
1072 | 8.23(1H, s), 8.20~8.19(3H, m), 7.98~7.82(11H, m), 7.70~7.31(14H, m) | |
1073 | 8.35~8.19(10H, m), 8.08~7.79(10H, m), 7.70~7.65(3H, m), 7.54~7.49(6H, m), 7.39~7.25(4H, m) | |
1078 | 9.08(1H, d), 8.84(1H, d), 8.23~8.17(5H, m), 8.05(1H, s), 7.94~7.49(19H, m) | |
1082 | 9.08(1H, d), 8.84(1H, d), 8.35~8.19(9H, m), 8.05(1H, s), 7.90~7.63(13H, m), 7.50~7.49(4H, m), 7.25(2H, d) | |
1084 | 8.55(1H, d), 8.36(2H, d), 8.23~8.19(4H, m), 8.12(1H, s), 7.99~7.85(9H, m), 7.70(1H, t), 7.58~7.49(8H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
1090 | 8.55(1H, d), 8.45(1H, d), 8.36~8.32(3H, m), 8.23~8.20(3H, m), 8.12(1H, s), 7.99~7.85(7H, m), 7.70(2H, m), 7.56~7.49(8H, m), 7.25(2H, m) | |
1091 | 8.55(1H, d), 8.45(1H, d), 8.36(2H, m), 8.23~8.20(3H, m), 8.12(2H, m), 7.99~7.85(7H, m), 7.70(2H, m), 7.56~7.49(8H, m), 7.25(2H, m) | |
1093 | 8.36(2H, d), 8.23~8.20(3H, m), 8.12(1H, s), 8.08(1H, d), 7.99~7.85(6H, m), 7.70(1H, t), 7.54~7.39(8H, m), 7.39~7.31(2H, m) | |
1098 | 8.36(2H, m), 8.23~8.20(3H, m), 8.12(2H, m), 7.99~7.94(5H, m), 7.85~7.82(2H, m), 7.70~7.69(2H, m), 7.57~7.49(8H, m), 7.39~7.25(4H, m) | |
1102 | 8.85(1H, s), 8.37~8.36(3H, m), 8.20(1H, d), 8.12~7.50(19H, m), 7.38(1H, t), 7.28(1H, t), 1.69(6H, s) | |
1103 | 9.08(1H, d), 8.84(1H, d), 8.36(2H, d), 8.23~8.12(5H, m), 8.05~7.85(6H, m), 7.70~7.49(11H, m) | |
1105 | 9.08(1H, d), 8.84(1H, d), 8.36(2H, d), 8.27~8.20(4H, m), 8.12(1H, s), 8.05~7.85(8H, m), 7.70~7.49(11H, m), 7.25(2H, m) | |
1109 | 8.55(1H, d), 8.23~8.19(5H, m), 8.12(1H, s), 7.99~7.85(11H, m), 7.70(1H, t), 7.58~7.49(8H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
1111 | 8.55(1H, d), 8.35(2H, m), 8.23~8.19(5H, m), 8.12(1H, s), 7.99~7.85(9H, m), 7.70(1H, t), 7.58~7.49(8H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
1114 | 8.55(1H, d), 8.45(1H, d), 8.32(1H, d), 8.23(3H, m), 8.20(1H, d), 8.12(1H, s), 7.99~7.85(9H, m), 7.70(2H, m), 7.55~7.49(6H, m), 7.25(2H, m) | |
1119 | 8.55(1H, d), 8.45(1H, d), 8.35~8.20(9H, m), 8.12(1H, s), 7.99~7.85(5H, m), 7.70(2H, m), 7.56~7.49(8H, m), 7.25(2H, m) | |
1121 | 8.35(2H, d), 8.23~8.20(4H, m), 8.12~8.09(2H, m), 7.99~7.70(8H, m), 7.55~7.49(7H, m), 7.38(1H, t), 7.28(1H, t), 1.69(6H, s) | |
1124 | 9.08(1H, d), 8.84(1H, d), 8.30~8.20(7H, m), 8.12(1H, s), 8.05~7.85(8H, m), 7.70~7.49(11H, m), 7.25(2H, d) | |
1129 | 8.55(1H, d), 8.36(2H, d), 8.23~8.19(6H, m), 7.94~7.83(6H, m), 7.70~7.49(11H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
1135 | 8.55(1H, d), 8.45(1H, d), 8.36(2H, m), 8.23~8.20(3H, m), 7.96~7.79(9H, m), 7.70(2H, m), 7.56~7.49(8H, m), 7.25(2H, d) | |
1138 | 8.36(2H, d), 8.23~8.20(3H, m), 7.98~7.79(7H, m), 7.70~7.69(2H, m), 7.57~7.49(8H, m), 7.39~7.31(2H, m) | |
1142 | 8.36(2H, d), 8.23~8.20(3H, m), 7.98~7.79(9H, m), 7.70~7.69(2H, m), 7.57~7.49(8H, m), 7.39~7.25(4H, m) | |
1143 | 8.36(2H, d), 8.23~8.20(3H, m), 8.08~7.79(12H, m), 7.70(1H, t), 7.54~7.49(8H, m), 7.39~7.25(6H, m) | |
1146 | 8.85(1H, s), 8.36(3H, m), 8.20(1H, d), 8.09~7.50(19H, m), 7.38(1H, t), 7.28(1H, t), 1.69(6H, s) | |
1147 | 9.08(1H, d), 8.84(1H, d), 8.36(2H, d), 8.23~8.17(4H, m), 8.05(1H, s), 7.94~7.49(17H, m) | |
1150 | 8.55(1H, d), 8.23~8.19(5H, m), 7.94~7.83(12H, m), 7.70(1H, t), 7.58~7.49(8H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
1151 | 8.55(1H, d), 8.35(2H, d), 8.23~8.19(6H, m), 7.94~7.79(7H, m), 7.70~7.49(11H, m), 7.35(1H, t), 7.20~7.16(2H, m) | |
1157 | 8.85(1H, s), 8.55(1H, d), 8.45~8.35(4H, m), 8.23~8.20(2H, m), 8.06~7.49(19H, m) | |
1162 | 8.55(1H, d), 8.45(1H, d), 8.32~8.20(7H, m), 7.94~7.79(8H, m), 7.70(2H, m), 7.56~7.49(8H, m), 7.25(2H, d) | |
1165 | 8.35(2H, d), 8.23~8.20(4H, m), 8.09(1H, d), 7.90~7.70(9H, m), 7.55~7.49(7H, m), 7.38(1H, t), 7.28(1H, t) 1.69(6H, s) | |
1166 | 8.23~8.20(4H, m), 8.09(1H, d), 7.94~7.70(11H, m), 7.55~7.49(7H, m), 7.38(1H, t), 7.28(1H, t), 1.69(6H, s) | |
1169 | 9.11(1H, d), 8.70(1H, d), 8.46~8.20(10H, m), 7.92~7.49(19H, m) |
化合物 | FD-MS | 化合物 | FD-MS |
1 | m/z=629.71 (C43H27N5O=629.22) | 519 | m/z=676.76 (C48H28N4O=676.23) |
11 | m/z=707.84 (C48H29N5S=707.21) | 524 | m/z=642.75 (C45H30N4O=642.24) |
13 | m/z=783.94 (C54H33N5S=783.25) | 527 | m/z=768.90 (C55H36N4O=768.29) |
16 | m/z=757.90 (C52H31N5S=757.23) | 537 | m/z=702.80 (C50H30N4O=702.24) |
17 | m/z=648.80 (C42H24N4S2=648.14) | 540 | m/z=702.80 (C50H30N4O=702.24) |
20 | m/z=724.89 (C48H28N4S2=724.18) | 546 | m/z=741.84 (C52H31N5O=741.25) |
21 | m/z=724.89 (C48H28N4S2=724.18) | 550 | m/z=741.84 (C52H31N5O=741.25) |
24 | m/z=774.95 (C52H30N4S2=774.19) | 553 | m/z=632.73 (C42H24N4OS=632.17) |
29 | m/z=632.73 (C42H24N4OS=632.17) | 557 | m/z=696.82 (C47H28N4OS=696.20) |
38 | m/z=758.89 (C52H30N4OS=758.21) | 559 | m/z=708.83 (C48H28N4OS=708.20) |
40 | m/z=708.83 (C48H28N4OS=708.20) | 562 | m/z=758.89 (C52H30N4OS=758.21) |
42 | m/z=692.83 (C48H28N4S=692.20) | 563 | m/z=616.67 (C42H24N4O2=616.19) |
44 | m/z=742.89 (C52H30N4S=742.22) | 567 | m/z=692.76 (C48H28N4O2=692.22) |
50 | m/z=708.87 (C49H32N4S=708.23) | 573 | m/z=741.84 (C52H31N5O=741.25) |
52 | m/z=734.91 (C51H34N4S=734.25) | 576 | m/z=692.76 (C48H28N4O2=692.22) |
55 | m/z=666.79 (C46H26N4S=666.19) | 579 | m/z=752.86 (C54H32N4O=752.26) |
60 | m/z=642.77 (C44H26N4S=642.19) | 578 | m/z=752.86 (C54H32N4O=752.26) |
62 | m/z=718.87 (C50H30N4S=718.22) | 585 | m/z=642.75 (C45H30N4O=642.24) |
65 | m/z=718.87 (C50H30N4S=718.22) | 589 | m/z=692.80 (C49H32N4O=692.26) |
71 | m/z=707.84 (C48H29N5S=707.21) | 588 | m/z=768.90 (C55H36N4O=768.29) |
72 | m/z=757.90 (C52H31N5S=757.23) | 591 | m/z=768.90 (C55H36N4O=768.29) |
75 | m/z=834.00 (C58H35N5S=833.26) | 593 | m/z=776.88 (C56H32N4O=776.26) |
78 | m/z=724.89 (C48H28N4S2=724.18) | 597 | m/z=752.86 (C54H32N4O=752.26) |
80 | m/z=698.86 (C46H26N4S2=698.16) | 598 | m/z=752.86 (C54H32N4O=752.26) |
82 | m/z=724.89 (C48H28N4S2=724.18) | 604 | m/z=691.78 (C48H29N5O=691.24) |
84 | m/z=698.86 (C46H26N4S2=698.16) | 605 | m/z=767.87 (C54H33N5O=767.27) |
87 | m/z=632.73 (C42H24N4OS=632.17) | 608 | m/z=741.84 (C52H31N5O=741.25) |
93 | m/z=708.83 (C48H28N4OS=708.20) | 609 | m/z=767.87 (C54H33N5O=767.27) |
98 | m/z=758.89 (C52H30N4OS=758.21) | 613 | m/z=632.73 (C42H24N4OS=632.17) |
100 | m/z=708.83 (C48H28N4OS=708.20) | 616 | m/z=758.89 (C52H30N4OS=758.21) |
106 | m/z=742.89 (C52H30N4S=742.22) | 617 | m/z=708.83 (C48H28N4OS=708.20) |
116 | m/z=734.91 (C51H34N4S=734.25) | 618 | m/z=708.83 (C48H28N4OS=708.20) |
122 | m/z=718.87 (C50H30N4S=718.22) | 621 | m/z=758.89 (C52H30N4OS=758.21) |
125 | m/z=768.92 (C54H32N4S=768.23) | 626 | m/z=742.82 (C52H30N4O2=742.24) |
127 | m/z=707.84 (C48H29N5S=707.21) | 632 | m/z=666.72 (C46H26N4O2=666.21) |
130 | m/z=757.90 (C52H31N5S=757.23) | 638 | m/z=676.76 (C48H28N4O=676.23) |
135 | m/z=834.00 (C58H35N5S=833.26) | 641 | m/z=752.86 (C54H32N4O=752.26) |
137 | m/z=648.80 (C42H24N4S2=648.14) | 645 | m/z=718.84 (C51H34N4O=718.27) |
140 | m/z=724.89 (C48H28N4S2=724.18) | 650 | m/z=768.90 (C55H36N4O=768.29) |
141 | m/z=724.89 (C48H28N4S2=724.18) | 653 | m/z=776.88 (C56H32N4O=776.26) |
144 | m/z=698.86 (C46H26N4S2=698.16) | 661 | m/z=752.86 (C54H32N4O=752.26) |
146 | m/z=774.95 (C52H30N4S2=774.19) | 663 | m/z=702.80 (C50H30N4O=702.24) |
155 | m/z=682.79 (C46H26N4OS=682.18) | 664 | m/z=767.87 (C54H33N5O=767.27) |
150 | m/z=682.79 (C46H26N4OS=682.18) | 666 | m/z=741.84 (C52H31N5O=741.25) |
152 | m/z=708.83 (C48H28N4OS=708.20) | 667 | m/z=767.87 (C54H33N5O=767.27) |
165 | m/z=768.92 (C54H32N4S=768.23) | 668 | m/z=741.84 (C52H31N5O=741.25) |
166 | m/z=658.81 (C45H30N4S=658.22) | 671 | m/z=867.99 (C62H37N5O=867.30) |
169 | m/z=784.97 (C55H36N4S=784.27) | 674 | m/z=632.73 (C42H24N4OS=632.17) |
190 | m/z=757.23 (C52H31N5S=757.90) | 680 | m/z=708.83 (C48H28N4OS=708.20) |
196 | m/z=783.94 (C54H33N5S=783.25) | 681 | m/z=708.83 (C48H28N4OS=708.20) |
198 | m/z=648.80 (C42H24N4S2=648.14) | 682 | m/z=732.85 (C50H28N4OS=732.20) |
199 | m/z=698.86 (C46H26N4S2=698.16) | 687 | m/z=666.72 (C46H26N4O2=666.21) |
203 | m/z=724.89 (C48H28N4S2=724.18) | 691 | m/z=666.72 (C46H26N4O2=666.21) |
209 | m/z=774.95 (C52H30N4S2=774.19) | 696 | m/z=692.76 (C48H28N4O2=692.22) |
219 | m/z=682.79 (C46H26N4OS=682.18) | 699 | m/z=742.82 (C52H30N4O2=742.24) |
220 | m/z=708.83 (C48H28N4OS=708.20) | 700 | m/z=692.76 (C48H28N4O2=692.22) |
226 | m/z=758.89 (C52H30N4OS=758.21) | 703 | m/z=676.76 (C48H28N4O=676.23) |
231 | m/z=658.81 (C45H30N4S=658.22) | 712 | m/z=718.84 (C51H34N4O=718.27) |
234 | m/z=734.91 (C51H34N4S=734.25) | 721 | m/z=826.95 (C60H34N4O=826.27) |
242 | m/z=742.90 (C52H30N4S=742.21) | 722 | m/z=702.80 (C50H30N4O=702.24) |
247 | m/z=744.23 (C50H30N4S=744.23) | 724 | m/z=752.86 (C54H32N4O=752.26) |
250 | m/z=706.85 (C49H30N4S=706.22) | 725 | m/z=690.79 (C49H30N4O=690.24) |
254 | m/z=782.95 (C55H34N4S=782.25) | 727 | m/z=690.79 (C49H30N4O=690.24) |
259 | m/z=647.81 (C43H25N3S2=647.15) | 731 | m/z=707.84 (C49H29N3OS=707.20) |
264 | m/z=723.90 (C49H29N3S2=723.18) | 736 | m/z=740.85 (C53H32N4O=740.26) |
265 | m/z=697.87 (C47H27N3S2=697.16) | 737 | m/z=707.84 (C49H29N3OS=707.20) |
266 | m/z=773.96 (C53H31N3S2=773.20) | 740 | m/z=707.84 (C49H29N3OS=707.20) |
270 | m/z=681.80 (C47H27N3OS=681.19) | 742 | m/z=757.90 (C53H31N3OS=757.22) |
275 | m/z=707.84 (C49H29N3OS=707.20) | 748 | m/z=615.68 (C43H25N3O2=615.19) |
282 | m/z=741.90 (C53H31N3S=741.22) | 750 | m/z=665.74 (C47H27N3O2=665.21) |
283 | m/z=657.82 (C46H31N3S=657.22) | 751 | m/z=691.77 (C49H29N3O2=691.23) |
285 | m/z=657.82 (C46H31N3S=657.22) | 753 | m/z=767.87 (C55H33N3O2=767.26) |
288 | m/z=707.88 (C50H33N3S=707.24) | 754 | m/z=675.77 (C49H29N3O=675.23) |
290 | m/z=733.92 (C52H35N3S=733.26) | 757 | m/z=675.77 (C49H29N3O=675.23) |
296 | m/z=641.78 (C45H27N3S=641.19) | 763 | m/z=767.91 (C56H37N3O=767.29) |
297 | m/z=641.78 (C45H27N3S=641.19) | 764 | m/z=691.82 (C50H33N3O=691.26) |
299 | m/z=793.97 (C57H35N3S=793.26) | 765 | m/z=817.97 (C60H39N3O=817.31) |
303 | m/z=756.91 (C53H32N4S=756.23) | 768 | m/z=649.75 (C47H27N3O=649.21) |
305 | m/z=833.01 (C59H36N4S=832.27) | 774 | m/z=751.87 (C55H33N3O=751.26) |
307 | m/z=756.91 (C53H32N4S=756.23) | 777 | m/z=740.85 (C53H32N4O=740.26) |
310 | m/z=647.81 (C43H25N3S2=647.15) | 778 | m/z=690.79 (C49H30N4O=690.24) |
315 | m/z=723.90 (C49H29N3S2=723.18) | 780 | m/z=766.88 (C55H34N4O=766.27) |
316 | m/z=723.90 (C49H29N3S2=723.18) | 782 | m/z=725.85 (C53H31N3O=725.24) |
318 | m/z=800.00 (C55H33N3S2=799.21) | 784 | m/z=740.85 (C53H32N4O=740.26) |
324 | m/z=707.84 (C49H29N3OS=707.20) | 786 | m/z=631.74 (C43H25N3OS=631.17) |
326 | m/z=707.84 (C49H29N3OS=707.20) | 788 | m/z=631.74 (C43H25N3OS=631.17) |
330 | m/z=757.90 (C53H31N3OS=757.22) | 789 | m/z=681.80 (C47H27N3OS=681.19) |
331 | m/z=707.84 (C49H29N3OS=707.20) | 796 | m/z=757.90 (C53H31N3OS=757.22) |
332 | m/z=691.84 (C49H29N3S=691.21) | 798 | m/z=615.68 (C43H25N3O2=615.19) |
336 | m/z=691.84 (C49H29N3S=691.21) | 803 | m/z=691.77 (C49H29N3O2=691.23) |
341 | m/z=707.88 (C50H33N3S=707.24) | 811 | m/z=725.83 (C53H31N3O=725.25) |
348 | m/z=733.92 (C52H35N3S=733.26) | 816 | m/z=641.76 (C46H31N3O=641.25) |
350 | m/z=665.80 (C47H27N3S=665.19) | 818 | m/z=641.76 (C46H31N3O=641.25) |
359 | m/z=793.97 (C57H35N3S=793.26) | 820 | m/z=691.82 (C50H33N3O=691.26) |
362 | m/z=706.85 (C49H30N4S=706.22) | 824 | m/z=767.91 (C56H37N3O=767.29) |
363 | m/z=706.85 (C49H30N4S=706.22) | 829 | m/z=775.89 (C57H33N3O=775.26) |
364 | m/z=756.91 (C53H32N4S=756.23) | 830 | m/z=701.81 (C51H31N3O=701.25) |
366 | m/z=756.91 (C53H32N4S=756.23) | 833 | m/z=751.87 (C55H33N3O=751.26) |
370 | m/z=647.81 (C43H25N3S2=647.15) | 836 | m/z=690.79 (C49H30N4O=690.24) |
371 | m/z=697.87 (C47H27N3S2=697.16) | 837 | m/z=690.79 (C49H30N4O=690.24) |
373 | m/z=723.90 (C49H29N3S2=723.18) | 839 | m/z=740.85 (C53H32N4O=740.26) |
375 | m/z=773.96 (C53H31N3S2=773.20) | 844 | m/z=631.74 (C43H25N3OS=631.17) |
382 | m/z=707.84 (C49H29N3OS=707.20) | 846 | m/z=707.84 (C49H29N3OS=707.20) |
385 | m/z=757.90 (C53H31N3OS=757.22) | 848 | m/z=707.84 (C49H29N3OS=707.20) |
386 | m/z=681.80 (C47H27N3OS=681.19) | 852 | m/z=757.90 (C53H31N3OS=757.22) |
391 | m/z=691.84 (C49H29N3S=691.21) | 854 | m/z=615.68 (C43H25N3O2=615.19) |
393 | m/z=691.84 (C49H29N3S=691.21) | 856 | m/z=615.68 (C43H25N3O2=615.19) |
396 | m/z=657.82 (C46H31N3S=657.22) | 864 | m/z=741.83 (C53H31N3O2=741.24) |
408 | m/z=715.86 (C51H29N3S=715.21) | 865 | m/z=741.83 (C53H31N3O2=741.24) |
416 | m/z=756.91 (C53H32N4S=756.23) | 867 | m/z=675.77 (C49H29N3O=675.23) |
419 | m/z=647.81 (C43H25N3S2=647.15) | 874 | m/z=691.82 (C50H33N3O=691.26) |
422 | m/z=647.81 (C43H25N3S2=647.15) | 876 | m/z=717.85 (C52H35N3O=717.28) |
424 | m/z=723.90 (C49H29N3S2=723.18) | 879 | m/z=767.91 (C56H37N3O=767.29) |
431 | m/z=631.74 (C43H25N3OS=631.17) | 880 | m/z=649.74 (C47H27N3O=649.22) |
432 | m/z=631.74 (C43H25N3OS=631.17) | 882 | m/z=727.85 (C53H33N3O=727.26) |
441 | m/z=757.90 (C53H31N3OS=757.22) | 885 | m/z=701.81 (C51H31N3O=701.25) |
443 | m/z=681.80 (C47H27N3OS=681.19) | 886 | m/z=701.81 (C51H31N3O=701.25) |
445 | m/z=691.84 (C49H29N3S=691.21) | 888 | m/z=690.79 (C49H30N4O=690.24) |
450 | m/z=707.88 (C50H33N3S=707.24) | 889 | m/z=690.79 (C49H30N4O=690.24) |
452 | m/z=733.92 (C52H35N3S=733.26) | 894 | m/z=816.94 (C59H36N4O=816.29) |
456 | m/z=715.86 (C51H29N3S=715.21) | 897 | m/z=757.90 (C53H31N3OS=757.22) |
460 | m/z=767.94 (C55H33N3S=767.24) | 898 | m/z=631.74 (C43H25N3OS=631.17) |
462 | m/z=722.92 (C50H30N2S2=722.19) | 902 | m/z=707.84 (C49H29N3OS=707.20) |
465 | m/z=656.84 (C47H32N2S=656.23) | 903 | m/z=681.80 (C47H27N3OS=681.19) |
467 | m/z=705.87 (C50H31N3S=705.22) | 905 | m/z=707.84 (C49H29N3OS=707.20) |
471 | m/z=766.95 (C56H34N2S=766.24) | 906 | m/z=691.77 (C49H29N3O2=691.23) |
476 | m/z=630.76 (C44H26N2OS=630.18) | 907 | m/z=691.77 (C49H29N3O2=691.23) |
479 | m/z=741.84 (C52H31N5O=741.25) | 913 | m/z=665.74 (C47H27N3O2=665.21) |
480 | m/z=767.87 (C54H33N5O=767.27) | 916 | m/z=691.77 (C49H29N3O2=691.23) |
486 | m/z=767.87 (C54H33N5O=767.27) | 917 | m/z=741.83 (C53H31N3O2=741.24) |
488 | m/z=767.87 (C54H33N5O=767.27) | 920 | m/z=741.83 (C53H31N3O2=741.24) |
493 | m/z=758.89 (C52H30N4OS=758.21) | 930 | m/z=717.85 (C52H35N3O=717.28) |
498 | m/z=708.83 (C48H28N4OS=708.20) | 931 | m/z=649.74 (C47H27N3O=649.22) |
499 | m/z=682.79 (C46H26N4OS=682.18) | 935 | m/z=751.87 (C55H33N3O=751.26) |
502 | m/z=616.67 (C42H24N4O2=616.19) | 936 | m/z=689.80 (C50H31N3O=689.25) |
506 | m/z=692.76 (C48H28N4O2=692.22) | 938 | m/z=690.79 (C50H30N2O2=690.23) |
508 | m/z=742.82 (C52H30N4O2=742.24) | 943 | m/z=706.85 (C50H30N2OS=706.21) |
511 | m/z=742.82 (C52H30N4O2=742.24) | 948 | m/z=640.77 (C47H32N2O=640.25) |
517 | m/z=692.76 (C48H28N4O2=692.22) | 949 | m/z=689.80 (C50H31N3O=689.25) |
953 | m/z=707.85 (C48H29N5S=707.21) | 956 | m/z=698.16 (C46H26N4S2=698.16) |
960 | m/z=774.96 (C52H30N4S2=774.19) | 962 | m/z=632.74 (C42H24N4OS=632.16) |
966 | m/z=708.83 (C48H28N4OS=708.19) | 969 | m/z=658.82 (C45H30N4S=658.21) |
973 | m/z=718.87 (C50H30N4S=718.21) | 975 | m/z=706.86 (C49H30N4S=706.21) |
981 | m/z=697.87 (C47H27N3S2=697.16) | 984 | m/z=647.81 (C43H25N3S2=647.14) |
986 | m/z=723.91 (C49H29N3S2=723.18) | 989 | m/z=723.91 (C49H29N3S2=723.18) |
991 | m/z=631.75 (C43H25N3OS=631.17) | 996 | m/z=631.75 (C43H25N3OS=631.17) |
1003 | m/z=657.83 (C46H31N3S=657.22) | 1007 | m/z=733.93 (C52H35N3S=733.25) |
1013 | m/z=641.79 (C45H27N3S=641.19) | 1014 | m/z=717.89 (C51H31N3S=717.22) |
1020 | m/z=602.69 (C42H26N4O=602.21) | 1021 | m/z=601.70 (C43H27N3O=601.21) |
1026 | m/z=694.85 (C48H30N4S=694.21) | 1027 | m/z=677.80 (C49H31N3O=677.24) |
1030 | m/z=694.85 (C48H30N4S=694.21) | 1031 | m/z=693.86 (C49H31N3S=693.22) |
1033 | m/z=693.86 (C49H31N3S=693.22) | 1034 | m/z=618.75 (C42H26N4S=618.18) |
1035 | m/z=601.70 (C43H27N3O=601.21) | 1036 | m/z=691.79 (C48H29N5O=691.23) |
1039 | m/z=632.74 (C42H24N4OS=632.16) | 1041 | m/z=682.80 (C46H26N4OS=682.18) |
1042 | m/z=708.83 (C48H28N4OS=708.19) | 1044 | m/z=758.89 (C52H30N4OS=758.21) |
1046 | m/z=616.68 (C42H24N4O2=616.19) | 1049 | m/z=692.77 (C48H28N4O2=692.22) |
1052 | m/z=642.76 (C45H30N4O=642.24) | 1053 | m/z=626.71 (C44H26N4O=626.21) |
1057 | m/z=690.80 (C49H30N4O=690.24) | 1058 | m/z=690.80 (C49H30N4O=690.24) |
1061 | m/z=707.85 (C49H29N3OS=707.20) | 1065 | m/z=665.75 (C47H27N3O2=665.21) |
1072 | m/z=691.79 (C49H29N3O2=691.22) | 1073 | m/z=767.88 (C55H33N3O2=767.25) |
1078 | m/z=625.73 (C45H27N3O=625.21) | 1082 | m/z=701.82 (C51H31N3O=701.24) |
1084 | m/z=707.85 (C48H29N5S=707.21) | 1090 | m/z=724.90 (C48H28N4S2=724.17) |
1091 | m/z7=24.90 (C48H28N4S2=724.17) | 1093 | m/z=632.74 (C42H24N4OS=632.16) |
1098 | m/z=708.83 (C48H28N4OS=708.19) | 1102 | m/z=708.88 (C49H32N4S=708.23) |
1103 | m/z=642.78 (C44H26N4S=642.18) | 1105 | m/z=718.87 (C50H30N4S=718.21) |
1109 | m/z=706.86 (C49H30N4S=706.21) | 1111 | m/z=706.86 (C49H30N4S=706.21) |
1119 | m/z=723.91 (C49H29N3S2=723.18) | 1121 | m/z=657.83 (C46H31N3S=657.22) |
1124 | m/z=717.89 (C51H31N3S=717.22) | 1129 | m/z=691.79 (C48H29N5O=691.23) |
1135 | m/z=708.83 (C48H28N4OS=708.19) | 1138 | m/z=616.68 (C42H24N4O2=616.19) |
1142 | m/z=692.77 (C48H28N4O2=692.22) | 1143 | m/z=768.87 (C54H32N4O2=768.25) |
1146 | m/z=692.82 (C49H32N4O=692.25) | 1147 | m/z=626.71 (C44H26N4O=626.21) |
1150 | m/z=690.80 (C49H30N4O=690.24) | 1151 | m/z=690.80 (C49H30N4O=690.24) |
1157 | m/z=681.81 (C47H27N3OS=681.18) | 1162 | m/z=707.85 (C49H29N3OS=707.20) |
1165 | m/z=641.77 (C46H31N3O=641.24) | 1166 | m/z=641.77 (C46H31N3O=641.24) |
1169 | m/z=701.82 (C51H31N3O=701.24) |
連續地使用三氯乙烯、丙酮、乙醇以及蒸餾水各自5分鐘來超音波清洗自用於OLED的玻璃(由三星康寧有限公司(Samsung-Corning Co., Ltd.)製造)獲得的透明ITO電極薄膜,將其儲存於異丙醇中,且使用。
隨後,抽空腔室直至其中的真空度達至10-6
托,且接著2-TNATA藉由施加電流至所述區室而蒸發,以在ITO基板上沈積具有600埃厚度的電洞注入層。
在如上形成電洞注入層及電洞轉移層之後,具有如下結構的發藍光材料沈積於其上作為發光層。特定言之,在真空沈積設備中的一側區室中,真空沈積200埃厚度的發藍光主體材料H1,且於其上真空沈積相對於主體材料的5%的發藍光摻雜劑材料D1。
將氟化鋰(LiF)沈積至厚度為10埃作為電子注入層,且將Al陰極沈積至厚度為1,000埃,且因此製造OLED。
同時,在10-6
托至10-8
托下藉由OLED製造中使用的每種材料真空昇華純化所有製造OLED所需的有機化合物。
[比較例2及比較例3]
以與比較例1中相同的方式製造有機電致發光二極體,不同之處在於在形成電子轉移層時使用表32中呈現的化合物替代E1。
評估:有機電致發光二極體的驅動電壓、發光效率、色彩座標(CIE)以及使用壽命
量測根據本揭露內容製造的藍色有機發光二極體的驅動電壓、發光效率、色彩座標(color coordinate;CIE)以及使用壽命的結果如表32中所示。
使用由Mc科學公司(McScience Inc.)製造的M7000來量測電致發光(Electroluminescent;EL)特性,且藉由量測結果,當標準亮度為3,500坎德拉/平方米時使用由Mc科學公司製造的使用壽命量測系統(M6000)量測T95
。量測根據本揭露內容製造的藍色有機電致發光二極體的驅動電壓、發光效率、色彩座標(CIE)以及使用壽命的結果如表32中所示。
[表32]
化合物 | 驅動電壓(V) | 發光效率(cd/A) | CIE (x, y) | 使用壽命(T95) | |
比較例1 | E1 | 5.70 | 6.00 | (0.134, 0.102) | 20 |
比較例2 | A | 6.10 | 4.57 | (0.134, 0.098) | 18 |
比較例3 | B | 6.06 | 4.68 | (0.134, 0.098) | 19 |
實例1 | 1 | 5.42 | 6.22 | (0.134, 0.101) | 42 |
實例2 | 11 | 5.44 | 6.22 | (0.134, 0.102) | 34 |
實例3 | 13 | 5.62 | 5.95 | (0.134, 0.103) | 37 |
實例4 | 16 | 5.01 | 6.10 | (0.134, 0.100) | 32 |
實例5 | 17 | 5.62 | 6.38 | (0.134, 0.100) | 35 |
實例6 | 20 | 5.32 | 6.20 | (0.134, 0.102) | 39 |
實例7 | 24 | 5.45 | 6.11 | (0.134, 0.103) | 30 |
實例8 | 29 | 5.44 | 6.34 | (0.134, 0.102) | 36 |
實例9 | 38 | 5.62 | 6.20 | (0.134, 0.101) | 39 |
實例10 | 40 | 5.40 | 6.12 | (0.134, 0.103) | 40 |
實例11 | 42 | 5.61 | 6.01 | (0.134, 0.102) | 35 |
實例12 | 52 | 5.45 | 6.22 | (0.134, 0.101) | 37 |
實例13 | 55 | 4.98 | 5.99 | (0.134, 0.101) | 38 |
實例14 | 60 | 5.21 | 6.23 | (0.134, 0.100) | 45 |
實例15 | 62 | 5.05 | 6.12 | (0.134, 0.100) | 38 |
實例16 | 65 | 5.21 | 6.01 | (0.134, 0.101) | 35 |
實例17 | 71 | 5.31 | 5.78 | (0.134, 0.100) | 37 |
實例18 | 78 | 5.62 | 5.41 | (0.134, 0.100) | 30 |
實例19 | 80 | 5.44 | 6.13 | (0.134, 0.102) | 32 |
實例20 | 82 | 5.38 | 6.38 | (0.134, 0.101) | 39 |
實例21 | 84 | 5.38 | 6.20 | (0.134, 0.103) | 31 |
實例22 | 87 | 5.39 | 6.02 | (0.134, 0.102) | 39 |
實例23 | 93 | 5.31 | 5.87 | (0.134, 0.100) | 35 |
實例24 | 100 | 5.15 | 5.87 | (0.134, 0.102) | 33 |
實例25 | 114 | 5.21 | 5.90 | (0.134, 0.101) | 32 |
實例26 | 116 | 5.01 | 6.21 | (0.134, 0.101) | 39 |
實例27 | 125 | 5.62 | 5.90 | (0.134, 0.100) | 34 |
實例28 | 127 | 5.39 | 5.95 | (0.134, 0.101) | 34 |
實例29 | 130 | 5.40 | 5.85 | (0.134, 0.101) | 34 |
實例30 | 137 | 5.38 | 6.38 | (0.134, 0.101) | 39 |
實例31 | 140 | 5.38 | 6.04 | (0.134, 0.103) | 35 |
實例32 | 141 | 5.21 | 6.42 | (0.134, 0.102) | 40 |
實例33 | 144 | 5.01 | 6.01 | (0.134, 0.101) | 35 |
實例34 | 152 | 4.91 | 6.00 | (0.134, 0.102) | 35 |
實例35 | 155 | 5.21 | 6.12 | (0.134, 0.101) | 37 |
實例36 | 165 | 5.38 | 6.03 | (0.134, 0.101) | 35 |
實例37 | 166 | 5.00 | 6.10 | (0.134, 0.102) | 36 |
實例38 | 190 | 5.39 | 6.04 | (0.134, 0.102) | 32 |
實例39 | 198 | 5.33 | 6.21 | (0.134, 0.101) | 35 |
實例40 | 199 | 5.41 | 6.04 | (0.134, 0.102) | 34 |
實例41 | 203 | 5.01 | 5.99 | (0.134, 0.101) | 37 |
實例42 | 219 | 4.98 | 6.03 | (0.134, 0.101) | 34 |
實例43 | 220 | 5.21 | 6.07 | (0.134, 0.102) | 38 |
實例44 | 234 | 5.39 | 5.95 | (0.134, 0.101) | 34 |
實例45 | 254 | 5.12 | 6.41 | (0.134, 0.102) | 44 |
實例46 | 259 | 4.98 | 6.34 | (0.134, 0.100) | 41 |
實例47 | 264 | 5.12 | 6.51 | (0.134, 0.100) | 44 |
實例48 | 265 | 5.21 | 6.22 | (0.134, 0.102) | 37 |
實例49 | 266 | 5.23 | 6.22 | (0.134, 0.100) | 38 |
實例50 | 270 | 5.11 | 6.21 | (0.134, 0.100) | 35 |
實例51 | 275 | 5.62 | 5.98 | (0.134, 0.100) | 39 |
實例52 | 285 | 4.75 | 5.78 | (0.134, 0.102) | 38 |
實例53 | 288 | 4.72 | 5.88 | (0.134, 0.102) | 38 |
實例54 | 290 | 4.91 | 5.98 | (0.134, 0.100) | 47 |
實例55 | 296 | 5.01 | 6.02 | (0.134, 0.100) | 45 |
實例56 | 297 | 5.00 | 6.61 | (0.134, 0.101) | 44 |
實例57 | 305 | 5.62 | 5.98 | (0.134, 0.100) | 34 |
實例58 | 307 | 5.31 | 6.53 | (0.134, 0.102) | 35 |
實例59 | 310 | 5.31 | 6.55 | (0.134, 0.102) | 38 |
實例60 | 315 | 5.21 | 6.40 | (0.134, 0.101) | 41 |
實例61 | 316 | 5.44 | 6.04 | (0.134, 0.100) | 32 |
實例62 | 326 | 5.21 | 6.11 | (0.134, 0.100) | 47 |
實例63 | 330 | 4.96 | 6.88 | (0.134, 0.100) | 30 |
實例64 | 331 | 4.95 | 6.95 | (0.134, 0.100) | 31 |
實例65 | 332 | 5.24 | 6.01 | (0.134, 0.100) | 35 |
實例66 | 336 | 5.62 | 5.98 | (0.134, 0.100) | 30 |
實例67 | 348 | 4.98 | 6.21 | (0.134, 0.102) | 46 |
實例68 | 350 | 5.40 | 6.12 | (0.134, 0.101) | 29 |
實例69 | 362 | 5.27 | 6.33 | (0.134, 0.101) | 43 |
實例70 | 363 | 5.01 | 6.20 | (0.134, 0.102) | 44 |
實例71 | 366 | 5.39 | 6.88 | (0.134, 0.100) | 30 |
實例72 | 370 | 5.21 | 6.21 | (0.134, 0.100) | 30 |
實例73 | 371 | 5.02 | 6.11 | (0.134, 0.101) | 38 |
實例74 | 373 | 5.15 | 6.11 | (0.134, 0.100) | 40 |
實例75 | 382 | 4.82 | 6.00 | (0.134, 0.102) | 40 |
實例76 | 391 | 5.21 | 6.53 | (0.134, 0.102) | 33 |
實例77 | 393 | 5.40 | 6.12 | (0.134, 0.101) | 31 |
實例78 | 396 | 4.98 | 6.22 | (0.134, 0.102) | 43 |
實例79 | 408 | 5.51 | 6.21 | (0.134, 0.102) | 39 |
實例80 | 416 | 5.01 | 6.11 | (0.134, 0.100) | 46 |
實例81 | 419 | 5.44 | 6.13 | (0.134, 0.100) | 32 |
實例82 | 422 | 5.42 | 6.02 | (0.134, 0.100) | 33 |
實例83 | 431 | 5.28 | 6.11 | (0.134, 0.102) | 38 |
實例84 | 432 | 5.30 | 6.01 | (0.134, 0.102) | 31 |
實例85 | 443 | 5.31 | 6.04 | (0.134, 0.102) | 32 |
實例86 | 445 | 4.63 | 6.11 | (0.134, 0.102) | 34 |
實例87 | 460 | 4.91 | 6.12 | (0.134, 0.100) | 33 |
實例88 | 462 | 4.99 | 6.01 | (0.134, 0.100) | 31 |
實例89 | 467 | 4.98 | 6.01 | (0.134, 0.100) | 33 |
實例90 | 480 | 5.62 | 5.98 | (0.134, 0.100) | 33 |
實例91 | 486 | 5.43 | 6.03 | (0.134, 0.102) | 35 |
實例92 | 498 | 4.88 | 6.01 | (0.134, 0.102) | 42 |
實例93 | 499 | 5.40 | 6.12 | (0.134, 0.101) | 39 |
實例94 | 502 | 5.01 | 6.04 | (0.134, 0.100) | 37 |
實例95 | 506 | 5.39 | 6.01 | (0.134, 0.101) | 32 |
實例96 | 508 | 4.89 | 6.24 | (0.134, 0.102) | 38 |
實例97 | 517 | 4.91 | 6.82 | (0.134, 0.100) | 30 |
實例98 | 519 | 5.19 | 5.71 | (0.134, 0.102) | 32 |
實例99 | 524 | 5.33 | 6.78 | (0.134, 0.100) | 31 |
實例100 | 546 | 4.90 | 5.71 | (0.134, 0.100) | 31 |
實例101 | 550 | 4.98 | 6.03 | (0.134, 0.100) | 37 |
實例102 | 553 | 5.32 | 5.98 | (0.134, 0.100) | 33 |
實例103 | 557 | 5.02 | 6.11 | (0.134, 0.100) | 37 |
實例104 | 559 | 5.05 | 6.09 | (0.134, 0.100) | 40 |
實例105 | 562 | 5.42 | 6.11 | (0.134, 0.101) | 33 |
實例106 | 563 | 4.85 | 6.01 | (0.134, 0.102) | 38 |
實例107 | 567 | 4.80 | 6.14 | (0.134, 0.100) | 39 |
實例108 | 573 | 4.98 | 6.22 | (0.134, 0.100) | 32 |
實例109 | 576 | 5.03 | 5.98 | (0.134, 0.100) | 33 |
實例110 | 585 | 5.25 | 6.02 | (0.134, 0.101) | 35 |
實例111 | 588 | 5.25 | 5.70 | (0.134, 0.101) | 32 |
實例112 | 604 | 4.74 | 5.83 | (0.134, 0.102) | 35 |
實例113 | 605 | 5.42 | 6.13 | (0.134, 0.101) | 35 |
實例114 | 608 | 4.74 | 5.83 | (0.134, 0.102) | 35 |
實例115 | 609 | 5.31 | 6.10 | (0.134, 0.101) | 36 |
實例116 | 613 | 5.44 | 5.89 | (0.134, 0.100) | 41 |
實例117 | 617 | 5.36 | 6.01 | (0.134, 0.101) | 37 |
實例118 | 618 | 5.21 | 6.11 | (0.134, 0.100) | 37 |
實例119 | 621 | 5.11 | 6.21 | (0.134, 0.100) | 36 |
實例120 | 626 | 5.26 | 6.07 | (0.134, 0.100) | 34 |
實例121 | 632 | 5.34 | 6.11 | (0.134, 0.101) | 38 |
實例122 | 641 | 4.86 | 5.93 | (0.134, 0.100) | 32 |
實例123 | 653 | 5.21 | 6.11 | (0.134, 0.102) | 34 |
實例124 | 661 | 5.31 | 5.88 | (0.134, 0.100) | 32 |
實例125 | 664 | 5.31 | 6.01 | (0.134, 0.100) | 35 |
實例126 | 671 | 5.22 | 6.04 | (0.134, 0.100) | 35 |
實例127 | 674 | 5.13 | 6.24 | (0.134, 0.102) | 41 |
實例128 | 680 | 5.31 | 6.21 | (0.134, 0.102) | 37 |
實例129 | 681 | 4.72 | 5.91 | (0.134, 0.102) | 38 |
實例130 | 682 | 4.79 | 6.55 | (0.134, 0.102) | 31 |
實例131 | 699 | 4.88 | 6.13 | (0.134, 0.101) | 31 |
實例132 | 700 | 5.12 | 5.89 | (0.134, 0.100) | 34 |
實例133 | 703 | 5.31 | 6.01 | (0.134, 0.101) | 35 |
實例134 | 712 | 5.11 | 6.21 | (0.134, 0.100) | 39 |
實例135 | 721 | 5.45 | 6.21 | (0.134, 0.101) | 37 |
實例136 | 722 | 5.44 | 6.22 | (0.134, 0.102) | 34 |
實例137 | 725 | 4.99 | 6.21 | (0.134, 0.103) | 46 |
實例138 | 731 | 4.98 | 6.44 | (0.134, 0.100) | 32 |
實例139 | 736 | 5.62 | 6.38 | (0.134, 0.100) | 35 |
實例140 | 737 | 5.45 | 5.87 | (0.134, 0.102) | 32 |
實例141 | 740 | 5.45 | 6.06 | (0.134, 0.103) | 41 |
實例142 | 748 | 5.01 | 6.43 | (0.134, 0.100) | 42 |
實例143 | 751 | 5.21 | 6.20 | (0.134, 0.101) | 48 |
實例144 | 754 | 5.40 | 5.88 | (0.134, 0.103) | 35 |
實例145 | 757 | 5.60 | 5.92 | (0.134, 0.102) | 35 |
實例146 | 764 | 5.45 | 6.22 | (0.134, 0.101) | 37 |
實例147 | 768 | 5.40 | 5.88 | (0.134, 0.103) | 34 |
實例148 | 774 | 5.21 | 6.21 | (0.134, 0.100) | 45 |
實例149 | 778 | 4.81 | 6.01 | (0.134, 0.100) | 46 |
實例150 | 780 | 5.33 | 6.21 | (0.134, 0.101) | 35 |
實例151 | 782 | 5.05 | 6.31 | (0.134, 0.100) | 44 |
實例152 | 786 | 5.03 | 6.11 | (0.134, 0.100) | 44 |
實例153 | 788 | 5.01 | 6.08 | (0.134, 0.100) | 40 |
實例154 | 789 | 5.38 | 6.38 | (0.134, 0.101) | 35 |
實例155 | 796 | 5.38 | 6.20 | (0.134, 0.103) | 34 |
實例156 | 798 | 4.80 | 6.01 | (0.134, 0.102) | 39 |
實例157 | 803 | 4.81 | 6.14 | (0.134, 0.100) | 42 |
實例158 | 811 | 5.62 | 5.98 | (0.134, 0.100) | 33 |
實例159 | 816 | 5.21 | 6.21 | (0.134, 0.101) | 44 |
實例160 | 818 | 5.39 | 6.01 | (0.134, 0.101) | 32 |
實例161 | 820 | 5.21 | 6.51 | (0.134, 0.100) | 40 |
實例162 | 829 | 5.39 | 6.01 | (0.134, 0.101) | 36 |
實例163 | 830 | 5.01 | 6.21 | (0.134, 0.100) | 47 |
實例164 | 836 | 4.98 | 6.22 | (0.134, 0.100) | 42 |
實例165 | 837 | 5.02 | 6.21 | (0.134, 0.101) | 43 |
實例166 | 839 | 4.71 | 5.45 | (0.134, 0.102) | 35 |
實例167 | 844 | 4.72 | 5.98 | (0.134, 0.102) | 40 |
實例168 | 848 | 4.74 | 6.50 | (0.134, 0.102) | 45 |
實例169 | 854 | 4.82 | 6.31 | (0.134, 0.102) | 44 |
實例170 | 856 | 4.83 | 6.29 | (0.134, 0.102) | 45 |
實例171 | 864 | 5.21 | 5.99 | (0.134, 0.100) | 33 |
實例172 | 865 | 5.44 | 5.89 | (0.134, 0.100) | 34 |
實例173 | 867 | 5.50 | 6.12 | (0.134, 0.103) | 37 |
實例174 | 874 | 5.60 | 6.21 | (0.134, 0.102) | 40 |
實例175 | 876 | 4.82 | 6.33 | (0.134, 0.102) | 45 |
實例176 | 880 | 5.21 | 6.13 | (0.134, 0.101) | 33 |
實例177 | 882 | 5.62 | 6.20 | (0.134, 0.100) | 34 |
實例178 | 886 | 5.11 | 6.12 | (0.134, 0.100) | 33 |
實例179 | 888 | 4.91 | 6.21 | (0.134, 0.101) | 46 |
實例180 | 889 | 4.93 | 6.21 | (0.134, 0.101) | 45 |
實例181 | 894 | 5.62 | 5.95 | (0.134, 0.100) | 33 |
實例182 | 898 | 5.13 | 6.21 | (0.134, 0.102) | 41 |
實例183 | 902 | 5.32 | 6.38 | (0.134, 0.101) | 43 |
實例184 | 903 | 5.25 | 6.20 | (0.134, 0.103) | 37 |
實例185 | 905 | 5.07 | 6.33 | (0.134, 0.102) | 44 |
實例186 | 906 | 4.77 | 6.21 | (0.134, 0.101) | 33 |
實例187 | 907 | 4.91 | 6.22 | (0.134, 0.102) | 33 |
實例188 | 913 | 4.91 | 6.12 | (0.134, 0.101) | 31 |
實例189 | 916 | 4.88 | 6.04 | (0.134, 0.101) | 33 |
實例190 | 917 | 4.68 | 5.88 | (0.134, 0.100) | 32 |
實例191 | 930 | 4.77 | 5.91 | (0.134, 0.100) | 39 |
實例192 | 931 | 4.98 | 5.93 | (0.134, 0.100) | 35 |
實例193 | 953 | 4.91 | 6.21 | (0.134, 0.100) | 46 |
實例194 | 960 | 5.12 | 6.21 | (0.134, 0.101) | 38 |
實例195 | 966 | 4.93 | 6.21 | (0.134, 0.101) | 45 |
實例196 | 969 | 5.62 | 5.95 | (0.134, 0.100) | 33 |
實例197 | 975 | 4.92 | 6.21 | (0.134, 0.102) | 41 |
實例198 | 984 | 5.32 | 6.38 | (0.134, 0.101) | 32 |
實例199 | 989 | 5.11 | 6.20 | (0.134, 0.103) | 37 |
實例200 | 996 | 5.07 | 6.33 | (0.134, 0.102) | 32 |
實例201 | 1003 | 5.32 | 6.21 | (0.134, 0.101) | 33 |
實例202 | 1007 | 5.11 | 6.31 | (0.134, 0.102) | 35 |
實例203 | 1013 | 4.91 | 6.12 | (0.134, 0.101) | 45 |
實例204 | 1020 | 4.88 | 6.04 | (0.134, 0.101) | 39 |
實例205 | 1021 | 4.68 | 5.88 | (0.134, 0.100) | 41 |
實例206 | 1026 | 4.77 | 5.91 | (0.134, 0.100) | 39 |
實例207 | 1030 | 5.20 | 5.93 | (0.134, 0.100) | 40 |
實例208 | 1031 | 5.21 | 5.91 | (0.134, 0.101) | 39 |
實例209 | 1033 | 5.20 | 5.91 | (0.134, 0.101) | 40 |
實例210 | 1034 | 4.66 | 6.21 | (0.134, 0.100) | 33 |
實例211 | 1035 | 4.71 | 6.01 | (0.134, 0.101) | 36 |
實例212 | 1036 | 5.01 | 6.21 | (0.134, 0.100) | 42 |
實例213 | 1042 | 4.98 | 6.22 | (0.134, 0.100) | 42 |
實例214 | 1058 | 5.02 | 6.21 | (0.134, 0.101) | 47 |
實例215 | 1061 | 4.81 | 6.11 | (0.134, 0.101) | 40 |
實例216 | 1084 | 5.11 | 5.98 | (0.134, 0.102) | 43 |
實例217 | 1093 | 4.74 | 5.21 | (0.134, 0.102) | 35 |
實例218 | 1098 | 5.21 | 6.31 | (0.134, 0.102) | 44 |
實例219 | 1111 | 5.15 | 6.01 | (0.134, 0.102) | 46 |
實例220 | 1135 | 4.71 | 5.45 | (0.134, 0.102) | 38 |
實例221 | 1143 | 4.72 | 5.98 | (0.134, 0.102) | 40 |
實例222 | 1147 | 4.71 | 5.45 | (0.134, 0.102) | 35 |
實例223 | 1150 | 4.72 | 6.01 | (0.134, 0.102) | 43 |
實例224 | 1151 | 4.84 | 6.21 | (0.134, 0.102) | 43 |
實例225 | 1162 | 4.82 | 6.31 | (0.134, 0.102) | 44 |
實例226 | 1165 | 5.11 | 5.89 | (0.134, 0.102) | 39 |
如自表32的結果所見,使用本揭露內容的藍色有機發光二極體的電子轉移層材料的有機發光二極體相較於比較例1具有較低驅動電壓以及改良的發光效率及使用壽命。
另外,相較於比較例2及比較例3,當使用化合物254、化合物259、化合物264、化合物290、化合物296、化合物297、化合物326、化合物348、化合物315、化合物362、化合物363、化合物416、化合物725、化合物748、化合物740、化合物751、化合物778、化合物803、化合物836、化合物837、化合物888、化合物889以及化合物905時,發光效率及使用壽命顯著地改良。
[實驗實例2](製造有機發光二極體-電洞阻擋層)
[比較例4]
連續地使用三氯乙烯、丙酮、乙醇以及蒸餾水各自5分鐘來超音波清洗自用於OLED的玻璃(由三星康寧有限公司製造)獲得的透明ITO電極薄膜,將其儲存於異丙醇中,且使用。
隨後,抽空腔室直至其中的真空度達至10-6
托,且接著2-TNATA藉由施加電流至所述區室而蒸發,以在ITO基板上沈積具有600埃厚度的電洞注入層。
在如上形成電洞注入層及電洞轉移層之後,具有如下結構的發藍光材料沈積於其上作為發光層。特定言之,在真空沈積設備中的一側區室中,真空沈積200埃厚度的發藍光主體材料H1,且於其上真空沈積相對於主體材料的5%的發藍光摻雜劑材料D1。
將氟化鋰(LiF)沈積至厚度為10埃作為電子注入層,且將Al陰極沈積至厚度為1,000埃,且因此製造OLED。
同時,在10-6
托至10-8
托下藉由OLED製造中使用的每種材料真空昇華純化所有製造OLED所需的有機化合物。
[比較例5及比較例6]
在比較例5中,以與比較例4中相同的方式製造有機電致發光二極體,不同之處在於E1形成為厚度為250埃作為電子轉移層,且在電子轉移層上,使用化合物C形成具有50埃厚度的電洞阻擋層。
另外,在比較例6中,以與比較例4中相同的方式製造有機電致發光二極體,不同之處在於E1形成為厚度為250埃作為電子轉移層,且在電子轉移層上,使用化合物D形成具有50埃厚度的電洞阻擋層。
[實例227至實例271]
以與比較例4中相同的方式製造有機電致發光二極體,不同之處在於E1形成為厚度為250埃作為電子轉移層,且在電子轉移層上,使用下表33中呈現的化合物形成具有50埃厚度的電洞阻擋層。
量測根據本揭露內容製造的藍色有機發光二極體的驅動電壓、發光效率、色彩座標(CIE)以及使用壽命的結果如表33中所示。
[表33]
化合物 | 驅動電壓(V) | 發光效率(cd/A) | CIE (x, y) | 使用壽命(T95) | |
比較例4 | - | 5.51 | 5.94 | (0.134, 0.100) | 31 |
比較例5 | C | 6.25 | 4.62 | (0.134, 0.101) | 18 |
比較例6 | D | 6.27 | 4.80 | (0.134, 0.101) | 20 |
實例227 | 1 | 5.14 | 6.32 | (0.134, 0.102) | 35 |
實例228 | 11 | 5.34 | 6.22 | (0.134, 0.101) | 36 |
實例229 | 16 | 5.24 | 6.30 | (0.134, 0.102) | 35 |
實例230 | 17 | 5.42 | 6.21 | (0.134, 0.101) | 36 |
實例231 | 60 | 5.33 | 6.01 | (0.134, 0.102) | 39 |
實例232 | 71 | 5.36 | 6.04 | (0.134, 0.102) | 37 |
實例233 | 93 | 5.35 | 6.11 | (0.134, 0.102) | 36 |
實例234 | 127 | 5.33 | 6.12 | (0.134, 0.102) | 36 |
實例235 | 166 | 5.36 | 6.05 | (0.134, 0.102) | 37 |
實例236 | 203 | 5.32 | 5.88 | (0.134, 0.102) | 34 |
實例237 | 234 | 5.22 | 5.91 | (0.134, 0.102) | 33 |
實例238 | 254 | 4.90 | 6.04 | (0.134, 0.102) | 45 |
實例239 | 264 | 4.98 | 6.11 | (0.134, 0.101) | 41 |
實例240 | 297 | 5.21 | 6.35 | (0.134, 0.102) | 44 |
實例241 | 326 | 5.32 | 6.55 | (0.134, 0.102) | 40 |
實例242 | 362 | 5.21 | 6.41 | (0.134, 0.101) | 43 |
實例243 | 396 | 5.21 | 6.44 | (0.134, 0.102) | 44 |
實例244 | 550 | 5.14 | 6.01 | (0.134, 0.101) | 34 |
實例245 | 585 | 5.18 | 6.11 | (0.134, 0.102) | 36 |
實例246 | 681 | 5.21 | 6.51 | (0.134, 0.101) | 45 |
實例247 | 725 | 5.11 | 6.44 | (0.134, 0.101) | 40 |
實例248 | 782 | 5.01 | 6.03 | (0.134, 0.102) | 42 |
實例249 | 816 | 5.05 | 6.01 | (0.134, 0.102) | 41 |
實例250 | 867 | 4.89 | 5.99 | (0.134, 0.102) | 41 |
實例251 | 902 | 4.90 | 5.91 | (0.134, 0.102) | 42 |
實例252 | 1027 | 4.99 | 5.81 | (0.134, 0.102) | 39 |
實例253 | 1039 | 4.88 | 5.71 | (0.134, 0.101) | 36 |
實例254 | 1041 | 4.91 | 5.61 | (0.134, 0.102) | 32 |
實例255 | 1044 | 5.42 | 6.21 | (0.134, 0.101) | 36 |
實例256 | 1053 | 4.98 | 5.81 | (0.134, 0.101) | 33 |
實例257 | 1057 | 5.36 | 6.21 | (0.134, 0.102) | 41 |
實例258 | 1063 | 4.88 | 5.70 | (0.134, 0.102) | 33 |
實例259 | 1078 | 4.91 | 5.81 | (0.134, 0.101) | 36 |
實例260 | 1082 | 5.36 | 6.05 | (0.134, 0.102) | 37 |
實例261 | 1090 | 5.32 | 5.88 | (0.134, 0.102) | 38 |
實例262 | 1093 | 4.81 | 5.51 | (0.134, 0.102) | 33 |
實例263 | 1102 | 5.21 | 6.04 | (0.134, 0.102) | 38 |
實例264 | 1103 | 4.78 | 5.41 | (0.134, 0.101) | 33 |
實例265 | 1111 | 5.24 | 6.30 | (0.134, 0.102) | 35 |
實例266 | 1119 | 5.42 | 6.21 | (0.134, 0.101) | 36 |
實例267 | 1124 | 5.33 | 6.01 | (0.134, 0.102) | 39 |
實例268 | 1151 | 5.36 | 6.04 | (0.134, 0.102) | 37 |
實例269 | 1157 | 4.98 | 5.71 | (0.134, 0.102) | 33 |
實例270 | 1166 | 4.71 | 5.88 | (0.134, 0.102) | 34 |
實例271 | 1169 | 5.36 | 6.05 | (0.134, 0.102) | 37 |
如自表33的結果所見,使用本揭露內容的藍色有機發光二極體的電洞阻擋層材料的有機發光二極體相較於比較例4具有較低驅動電壓以及顯著改良的發光效率及使用壽命。另外,相較於比較例5及比較例6,發光效率及使用壽命顯著地改良。此類結果是由於使用藍色有機發光二極體的電洞阻擋層材料的有機發光二極體為具有p型及n型兩者的雙極類型,且可防止電洞洩漏,且可將激子有效地鎖定於發光層中。
在上文中,已詳細描述本揭露內容的較佳實例,然而,本揭露內容的權利範疇不限於此,且所屬領域的技術人員使用所附申請專利範圍中定義的本揭露內容的基本概念作出的各種修改及改良亦屬於本揭露內容的權利範疇內。
100:基板
200:陽極
300:有機材料層
301:電洞注入層
302:電洞轉移層
303:發光層
304:電洞阻擋層
305:電子轉移層
306:電子注入層
400:陰極
圖1至圖3為各自示出根據本說明書之一個實施例的有機發光二極體的截面圖。
100:基板
200:陽極
300:有機材料層
400:陰極
Claims (22)
- 一種化合物,由以下化學式1表示: [化學式1] 其中,在化學式1中, X1 及X2 中的至少一者為-N-,且另一者為-CA-; Y為-S-或-O-; A以及R1 至R8 各自獨立地為氫、氘、氰基、經取代或未經取代的C1至C60烷基或經取代或未經取代的C6至C60芳基;且 A以及R1 至R4 中的任一者由以下化學式2表示, [化學式2] 在化學式2中, Ar1 及Ar2 各自獨立地為經取代或未經取代的C6至C60芳基或經取代或未經取代的C2至C60雜芳基; X3 至X7 中的至少一者為-N-,X3 至X7 中的一者為-(L1 )n1 -Ar1 ,X3 至X7 中的一者為-Ar2 -,且其餘為-N-、-CH-或-CR-中的一者; L1 及L2 各自獨立地為單鍵、經取代或未經取代的C6至C60伸芳基或經取代或未經取代的C2至C60伸雜芳基; n1及n2各自獨立地為0至2的整數中的一者; R為氘、-CN、經取代或未經取代的C1至C60直鏈或分支鏈烷基、經取代或未經取代的C6至C60單環或多環芳基或經取代或未經取代的C2至C60單環或多環雜芳基; 當化學式1的A由化學式2表示時,化學式2的Ar1 及Ar2 中的至少任一者為經取代或未經取代的C2至C60雜芳基或經取代或未經取代的C6至C60稠環芳基;且 *為鍵結位置。
- 如請求項1所述之化合物,其中化學式2為以下化學式3: [化學式3] 在化學式3中, Ar1 及Ar2 各自獨立地為經取代或未經取代的C6至C60芳基或經取代或未經取代的C2至C60雜芳基; X3 至X5 各自獨立地為-N-、-CH-或-CR-,且X3 至X5 中的至少一者為-N-; L1 及L2 各自獨立地為單鍵、經取代或未經取代的C6至C60伸芳基或經取代或未經取代的C2至C60伸雜芳基; 當化學式1的A由化學式3表示時,化學式3的Ar1 及Ar2 中的至少任一者為經取代或未經取代的C2至C60雜芳基或經取代或未經取代的C6至C60稠環芳基; n1及n2各自獨立地為0至2的整數中的一者;且 *為鍵結位置。
- 如請求項3所述之化合物,其中在化學式4中, X1 為-N-,且X2 為-CA-;且 A由化學式3表示。
- 如請求項3所述之化合物,其中在化學式4中, X1 為-CA-,且X2 為-N-;且 A由化學式3表示。
- 如請求項3所述之化合物,其中在化學式4中, X1 為-N-,且X2 為-CA-;且 R1 至R4 中的任一者由化學式3表示。
- 如請求項3所述之化合物,其中在化學式4中, X1 為-CA-,且X2 為-N-;且 R1 至R4 中的任一者由化學式3表示。
- 如請求項4所述之化合物,其中在化學式5中, X1 為-N-,且X2 為-CA-;且 A由化學式3表示。
- 如請求項4所述之化合物,其中在化學式5中, X1 為-CA-,且X2 為-N-;且 A由化學式3表示。
- 如請求項4所述之化合物,其中在化學式5中, X1 為-N-,且X2 為-CA-;且 R1 至R4 中的任一者由化學式3表示。
- 如請求項4所述之化合物,其中在化學式5中, X1 為-CA-,且X2 為-N-;且 R1 至R4 中的任一者由化學式3表示。
- 如請求項1所述之化合物,其中Ar1 為具有電洞特性的取代基。
- 如請求項1所述之化合物,其中Ar1 為: (1)經取代或未經取代的咔唑基; (2)經取代或未經取代的二苯并呋喃基; (3)經取代或未經取代的二苯并噻吩基; (4)經取代或未經取代的9,9-二烷基芴基或9,9-二芳基芴基,二烷基的烷基為經取代或未經取代的C1至C60烷基,且二芳基的芳基為經取代或未經取代的C6至C60芳基;或 (5)經取代或未經取代的9,9-二甲基芴基。
- 如請求項1所述之化合物,其中Ar1 為: (1)經取代或未經取代的蒽基; (2)經取代或未經取代的菲基; (3)經取代或未經取代的芘基; (4)經取代或未經取代的聯伸三苯基; (5)經取代或未經取代的聯三苯基;或 (6)經取代或未經取代的對聯四苯基。
- 一種有機光電二極體,包括: 彼此面對的陽極及陰極;以及 至少一個有機層,安置於所述陽極與所述陰極之間, 其中所述有機層包括如請求項1至請求項18中任一項所述之化合物。
- 如請求項19所述之有機光電二極體,其中所述有機層包括電子轉移層,且所述電子轉移層包括所述化合物。
- 如請求項19所述之有機光電二極體,其中所述有機層包括電洞阻擋層,且所述電洞阻擋層包括所述化合物。
- 一種顯示裝置,包括如請求項19所述之有機光電二極體。
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