TWI496809B - 用於光電裝置之聚合物 - Google Patents
用於光電裝置之聚合物 Download PDFInfo
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- TWI496809B TWI496809B TW099138727A TW99138727A TWI496809B TW I496809 B TWI496809 B TW I496809B TW 099138727 A TW099138727 A TW 099138727A TW 99138727 A TW99138727 A TW 99138727A TW I496809 B TWI496809 B TW I496809B
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- 229920000642 polymer Polymers 0.000 title claims description 65
- 230000005693 optoelectronics Effects 0.000 title claims description 7
- -1 phenylimine Chemical compound 0.000 claims description 78
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 125000001931 aliphatic group Chemical group 0.000 claims description 17
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 9
- NRSBAUDUBWMTGL-UHFFFAOYSA-N 2-(1-benzothiophen-2-yl)pyridine Chemical compound S1C2=CC=CC=C2C=C1C1=CC=CC=N1 NRSBAUDUBWMTGL-UHFFFAOYSA-N 0.000 claims description 8
- QLPKTAFPRRIFQX-UHFFFAOYSA-N 2-thiophen-2-ylpyridine Chemical compound C1=CSC(C=2N=CC=CC=2)=C1 QLPKTAFPRRIFQX-UHFFFAOYSA-N 0.000 claims description 7
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 claims description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 claims description 4
- XBHOUXSGHYZCNH-UHFFFAOYSA-N 2-phenyl-1,3-benzothiazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2S1 XBHOUXSGHYZCNH-UHFFFAOYSA-N 0.000 claims description 4
- FIISKTXZUZBTRC-UHFFFAOYSA-N 2-phenyl-1,3-benzoxazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2O1 FIISKTXZUZBTRC-UHFFFAOYSA-N 0.000 claims description 4
- VJHVLELNDFVKMS-UHFFFAOYSA-N 3-methoxy-2-phenylpyridine Chemical compound COC1=CC=CN=C1C1=CC=CC=C1 VJHVLELNDFVKMS-UHFFFAOYSA-N 0.000 claims description 4
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 4
- 229940067157 phenylhydrazine Drugs 0.000 claims description 4
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 claims description 4
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- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 3
- 244000046052 Phaseolus vulgaris Species 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
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- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
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- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 3
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- VYPADSNDNHLCFA-UHFFFAOYSA-N 1,2-dibromo-9,9-dioctylfluorene Chemical compound C1=C(Br)C(Br)=C2C(CCCCCCCC)(CCCCCCCC)C3=CC=CC=C3C2=C1 VYPADSNDNHLCFA-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
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- 239000000243 solution Substances 0.000 description 29
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 125000002015 acyclic group Chemical group 0.000 description 5
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
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- 229910052711 selenium Inorganic materials 0.000 description 4
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- 229910052717 sulfur Inorganic materials 0.000 description 4
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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Description
本發明大體上係關於適用於(例如)光電裝置發光層之聚合物,及包括該等聚合物之光電裝置。
預期利用可在受到偏壓時發光之薄膜材料之光電裝置(例如有機發光裝置(OLED))將成為平面顯示器技術之日益流行的形式。此點係因為OLED具有包括行動電話、個人數位助理(PDA)、電腦顯示器、車輛資訊顯示器、電視監控器、以及一般照明用光源之多種潛在應用。由於其色彩明亮、視角寬、與全動式視訊之相容性、溫度範圍寬、薄且保形的形狀因子、功率需求低及潛在之低成本製程,OLED被視作係未來取代陰極射線管(CRT)及液晶顯示器(LCD)之技術。由於其發光效率高,OLED被視為具有取代白熾燈、及或許甚至螢光燈、用於特定類型應用之燈之潛力。
OLED具有一夾層結構,其係由介於兩相反電極之間之一或多層有機層所組成。例如,多層式裝置通常包括至少三層:電洞注入/傳遞層、發射層及電子傳遞層(ETL)。此外,亦較佳為該電洞注入/傳遞層提供作為電子阻擋層而該ETL提供作為電洞阻擋層。單層式OLED僅包括一層介於兩相反電極之間之材料。
在一態樣中,本發明係關於一種含有如下式I之結構單元之聚合物:
其中R1
在各次出現時獨立地為C1
-C20
脂族基團、C3
-C20
芳族基團、或C3
-C20
環脂族基團;a在各次出現時獨立地為0至4之整數;Ar1
為芳基或雜芳基;Ar2
為茀;R2
為伸烷基、經取代之伸烷基、氧雜伸烷基、CO、或CO2
;R3
、R4
及R5
獨立地為氫、烷基、烷氧基、烷基芳基、芳基、芳烷基、雜芳基、經取代之烷基;經取代之烷氧基、經取代之烷基芳基、經取代之芳基、經取代之芳烷基、或經取代之雜芳基;且L係衍生自苯基吡啶、甲苯基吡啶、苯并噻吩基吡啶、苯基異喹啉、二苯并喹喏啉、茀基吡啶、酮基吡咯、2-(1-萘基)苯并噁唑))、2-苯基苯并噁唑、2-苯基苯并噻唑、香豆素、噻吩基吡啶、苯基吡啶、苯并噻吩基吡啶、3-甲氧基-2-苯基吡啶、噻吩基吡啶、苯基亞胺、乙烯基吡啶、吡啶基萘、吡啶基吡咯、吡啶基咪唑、苯基吲哚、其衍生物或其組合。
在另一態樣中,本發明係關於一種包括以上聚合物之光電裝置。
在一態樣中,本發明係關於一種含有如下式I之結構單元之聚合物:
其中R1
在各次出現時獨立地為C1
-C20
脂族基團、C3
-C20
芳族基團、或C3
-C20
環脂族基團;a在各次出現時獨立地為0至4之整數;Ar1
為芳基或雜芳基;Ar2
為茀;R2
為伸烷基、經取代之伸烷基、氧雜伸烷基、CO、或CO2
;R3
、R4
及R5
獨立地為氫、烷基、烷氧基、烷基芳基、芳基、芳烷基、雜芳基、經取代之烷基;經取代之烷氧基、經取代之烷基芳基、經取代之芳基、經取代之芳烷基、或經取代之雜芳基;且L係衍生自苯基吡啶、甲苯基吡啶、苯并噻吩基吡啶、苯基異喹啉、二苯并喹喏啉、茀基吡啶、酮基吡咯、2-(1-萘基)苯并噁唑))、2-苯基苯并噁唑、2-苯基苯并噻唑、香豆素、噻吩基吡啶、苯基吡啶、苯并噻吩基吡啶、3-甲氧基-2-苯基吡啶、噻吩基吡啶、苯基亞胺、乙烯基吡啶、吡啶基萘、吡啶基吡咯、吡啶基咪唑、苯基吲哚、其衍生物或其組合。
在另一態樣中,本發明係關於一種包括以上聚合物之光電裝置。
在一些實施例中,Ar1
係選自
在一些實施例中,L係衍生自苯基異喹啉。
在一些實施例中,聚合物包含如下式II之結構單元:
II,其中R6
與R7
在各次出現時獨立地為C1
-C20
脂族基團、C3
-C20
芳族基團、或C3
-C20
環脂族基團;b在各次出現時獨立地為0至3之整數;且c在各次出現時獨立地為0至2之整數。
在一些實施例中,聚合物包含如下式III之結構單元:
在一些實施例中,聚合物包含如下式IV之結構單元:
其中x+y=100。
在一些實施例中,聚合物包含衍生自以下之結構單元:
在一些實施例中,聚合物包含衍生自以下之結構單元:
在一些實施例中,聚合物包含衍生自以下之結構單元:
在一些實施例中,聚合物包含衍生自以下之結構單元:
聚合物係藉由包括鈴木(Suzuki)交叉偶合反應之製程在鹼與Pd催化劑之存在下於合適溶劑中製得。在惰性氛圍下,使反應混合物加熱一段時間。合適之溶劑包括(但不限於)二噁烷、THF、EtOH、甲苯及其混合物。例示性鹼包括KOAc、Na2
CO3
、K2
CO3
、Cs2
CO3
、磷酸鉀及其水合物。該等鹼可以固體粉末或以水溶液添加至該反應。最常用之催化劑包括外加第二配位體之Pd(PPh3
)4
、Pd2
(dba)3
、或Pd(OAc)2
、Pd(dba)2
。例示性配位體包括二烷基膦基聯苯配位體,諸如以下所示之結構V至IX,其中Cy為環己基:
在若干實施例中,聚合反應係進行一段獲得具適當分子量之聚合物所需之時間。聚合物之分子量係藉由習此相關技術者所悉知且包括黏度測定、光散射、及滲透壓測定之技術中之任一者測得。聚合物之分子量一般表示為數量平均分子量Mn,或重量平均分子量Mw。測得分子量平均之一種尤其有用的技術為凝膠滲透層析法(GPC),由其可得到數量平均及重量平均分子量兩者。聚合物之分子量並不具關鍵,且在一些實施例中,期望Mw大於30,000克/莫耳(g/mol)之聚合物,在其他實施例中,期望Mw大於50,000 g/mol之聚合物,然又在其他實施例中,期望Mw大於80,000 g/mol之聚合物。
熟習此項相關技術者當瞭解短語「如相對於聚苯乙烯標準品藉由凝膠滲透層析法所測」包括使用具有已知分子量之聚苯乙烯分子量標準品進行GPC儀器之校準。該等分子量標準品可於市面購買且分子量校準技術係慣常由熟習此項相關技術者所採用。如本內容之實驗部分反映,文中提到之分子量參數涵蓋使用氯仿作為用於GPC分析之溶劑。
聚合物具有4.8 eV之最高佔用分子軌域(HOMO)。該聚合物同時包括電洞傳遞部分及發光部分且不溶於隨後採用濕式塗佈或印刷製程施加以形成多層光電裝置之溶劑中。例如,該聚合物可用於白色OLED,其係藉由濕式塗佈或印刷製程製造且其具有一層以上之發光層。該聚合物可用於白色OLED之一層以上發光層中之至少一者。
在最簡單之情況下,一種光電裝置(例如OLED)一般包括陽極層及對應之陰極層與一置於該陽極與該陰極之間之有機電致發光層。當施加偏壓於該等電極兩端時,電子藉由陰極注入電致發光層中,同時電子自陽極由該電致發光層移去(或「電洞」自陽極「注入」電致發光層中)。在電洞與電子於該電致發光層中結合而形成單重態或三重態激子之情況下產生發光,發光係在單重態及/或三重態激子經由輻射衰變而衰變至其基態之情況下發生。
除了陽極、陰極及發光材料之外,可存於OLED中之其他組分包括電洞注入層、電子注入層、及電子傳遞層。電子傳遞層無需直接接觸陰極,且該電子傳遞層亦經常充作電洞阻擋層以防止電洞遷移至陰極。可存於有機發光裝置中之其他組分包括電洞傳遞層、電洞傳遞發光(發射)層及電子傳遞發光(發射)層。
在一實施例中,包括本發明聚合物之OLED可為包括單重態發射極之螢光OLED。在另一實施例中,包括本發明聚合物之OLED可為包括至少一個三重態發射極之磷光OLED。在另一實施例中,包括本發明聚合物之OLED包括至少一個單重態發射極及至少一個三重態發射極。包括本發明聚合物之該等OLED可包含藍色、黃色、橙色、紅色磷光染料(包括過渡金屬(諸如Ir、Os及Pt)之錯合物)中之一者或多者、任一種或一組合。特定言之,可使用電致磷光及電致螢光金屬錯合物,諸如該等由American Dye Source,Inc.,Quebec,Canada所供應者。含有式I至IV中任一者之結構單元之聚合物可為OLED之發射層、或電洞傳遞層或電子傳遞層、或電子注入層之部分或其任意組合。
有機電致發光層(即發射層)為位於有機發光裝置中之層,在操作期間,其容納明顯發生濃集之電子與電洞兩者且為激子形成及發光提供部位。電洞注入層為與陽極接觸之層,其促使電洞自陽極注入OLED之內層;及電子注入層為與陰極接觸之層,其促使電子自陰極注入OLED;電子傳遞層為可促使電子自陰極及/或電子注入層傳導至電荷再結合部位之層。在含電子傳遞層之有機發光裝置之操作期間,該電子傳遞層中存在之大多數電荷載子(即電洞及電子)為電子且發光可通過發射層中存在之電洞與電子之再結合產生。電洞傳遞層為在OLED操作期間可幫助電洞自陽極及/或電洞注入層傳導至電荷再結合部位之層且其無需與陽極直接接觸。電洞傳遞發射層為在OLED操作期間可幫助電洞傳導至電荷再結合部位之層,且其中大多數電荷載子為電洞,且其中發射不但係通過與剩餘電子再結合產生,而且係通過裝置別處之電荷再結合區域發生之能量轉移產生。電子傳遞發射層為在OLED操作期間可幫助電子傳導至電荷再結合部位之層,且其中大多數電荷載子為電子,且其中發射不但係通過與剩餘電洞再結合產生,而且係通過裝置別處之電荷再結合區域發生之能量轉移產生。
如藉由四點探針技術所測,適於作為陽極使用之材料包括具有較佳約1000歐姆/平方之體電阻率之材料。通常使用氧化銦錫(ITO)作為陽極,因為其對光透射實質上透明且因此可幫助電活性有機層所發射光逸出。可採用作為陽極層之其他材料包括氧化錫、氧化銦、氧化鋅、氧化銦鋅、鋅銦錫氧化物、氧化銻、及其混合物。
適於作為陰極使用之材料包括一般的電導體(包括(但不限於)金屬及金屬氧化物(諸如ITO等等)),其可使負電荷載子(電子)注入OLED之一或多層內層中。適於作為陰極使用之多種金屬包括K、Li、Na、Cs、Mg、Ca、Sr、Ba、Al、Ag、Au、In、Sn、Zn、Zr、Sc、Y、鑭系元素、其合金、及其混合物。適於作為陰極層之合適之合金材料包括Ag-Mg、Al-Li、In-Mg、Al-Ca、及Al-Au合金。在陰極中,亦可採用層狀非合金結構,諸如藉由金屬(諸如鋁或銀)之較厚層包層之金屬(諸如鈣)或金屬氟化物(諸如LiF)之薄層。
適用於電子傳遞層之材料包括聚(9,9-二辛基茀)、叁(8-羥基喹啉基)鋁(Alq3
)、2,9-二甲基-4,7-二苯基-1,1-啡啉、4,7-二苯基-1,10-啡啉、2-(4-聯苯基)-5-(4-第三丁基苯基)-1,3,4-噁二唑、3-(4-聯苯基)-4-苯基-5-(4-第三丁基苯基)-1,2,4-三唑、含1,3,4-噁二唑之聚合物、含1,3,4-三唑之聚合物、含喹喏啉之聚合物、及氰基-PPV。
適用於電洞傳遞層之材料包括:諸如,1,1-雙((二-4-甲苯基胺基)苯基)環己烷、N,N'-雙(4-甲基苯基)-N,N'-雙(4-乙基苯基)-(1,1'-(3,3'-二甲基)聯苯基)-4,4'-二胺、肆-(3-甲基苯基)-N,N,N',N'-2,5-苯二胺、苯基-4-N,N-二苯基胺基苯乙烯、對(二乙基胺基)苯甲醛二苯基腙、三苯基胺、1-苯基-3-(對-(二乙基胺基)苯乙烯基)-5-(對(二乙基胺基)苯基)吡唑啉、1,2-反-雙(9H-咔唑-9-基)環丁烷、N,N,N',N'-肆(4-甲基苯基)-(1,1'-聯苯)-4,4'-二胺、銅酞菁、聚乙烯基咔唑、(苯基甲基)聚矽烷;聚(3,4-伸乙二氧基噻吩)(PEDOT)、聚苯胺、聚乙烯基咔唑、三芳基二胺、四苯基二胺、芳族三級胺、具有胺基之腙衍生物、咔唑衍生物、三唑衍生物、咪唑衍生物、噁二唑衍生物,及美國專利第6,023,371號所揭示之聚噻吩類。
可取代習知之電致發光聚合物(諸如,聚茀(較佳聚(9,9-二辛基茀))及其共聚物(諸如聚(9,9'-二辛基茀-共-雙-N,N'-(4-丁基苯基)二苯基胺)(F8-TFB));聚(乙烯基咔唑)及聚伸苯基伸乙烯基及其衍生物或在其之外,在發光層中使用包含式I至IV中任一式之結構單元之聚合物。此外,發光層可包含藍色、黃色、橙色、綠色或紅色磷光染料或金屬錯合物、或其組合。適於作為磷光染料使用之材料包括(但不限於)叁(1-苯基異喹啉)銥(III)(紅色染料)、叁(2-苯基吡啶)銥(綠色染料)及雙(2-(4,6-二氟苯基)吡啶根-N,C2)銥(III)(藍色染料)。亦可使用購自ADS(American Dyes Source,Inc.)之市售電致螢光及電致磷光金屬錯合物。ADS綠色染料包括ADS060GE、ADS061GE、ADS063GE、ADS066GE、ADS078GE、及ADS090GE。ADS藍色染料包括ADS064BE、ADS065BE、及ADS070BE。ADS紅色染料包括ADS067RE、ADS068RE、ADS069RE、ADS075RE、ADS076RE、ADS067RE、及ADS077RE。
包含式I至IV中任一式之結構單元之聚合物可形成光電裝置(例如OLED)之電洞傳遞層或電洞注入層或發光層之部分。該等OLED可為包含藍色、黃色、橙色、綠色、紅色磷光染料中之一或多者、任一種或一組合之磷光性。
如文中所用術語「芳族基團」係指包含至少一個芳基具有至少一價之原子陣列。包含至少一個芳基具有至少一價之原子陣列可包括雜原子(諸如氮、硫、硒、矽及氧),或可純粹由碳與氫組成。如文中所用術語「芳族基團」包括(但不限於)苯基、吡啶基、呋喃基、噻吩基、萘基、伸苯基、及聯苯基。如所指者,該芳族基團包含至少一個芳基。該芳基不變地為具有4n+2個「非定域」電子之環狀結構,其中「n」為等於1或更大之整數,舉以下為例:苯基(n=1)、噻吩基(n=1)、呋喃基(n=1)、萘基(n=2)、薁基(n=2)、及蒽基(n=3)。該芳族基團亦可包括非芳族組分。例如,苄基為包括苯環(芳基)及亞甲基(非芳族組分)之芳族基團。類似地,四氫萘基為包含稠合至非芳族組分-(CH2
)4
-之芳基(C6
H3
)之芳族基團。為方便起見,文中定義術語「芳族基團」包括多種官能基,諸如:烷基、烯基、炔基、鹵代烷基、鹵代芳基、共軛二烯基、醇基、醚基、醛基、酮基、羧酸基團、醯基(例如羧酸衍生物(諸如酯及醯胺))、胺基、硝基、及其類似物。例如,4-甲基苯基為包含甲基之C7
芳族基團,該甲基為烷基官能基。類似地,2-硝基苯基為包含硝基之C6
芳族基團,該硝基為官能基。芳族基團包括鹵化芳族基團,諸如4-三氟甲基苯基、六氟亞異丙基雙(4-苯-1-基氧基)(即-OPhC(CF3
)2
PhO-)、4-氯甲基苯-1-基、3-三氟乙烯基-2-噻吩基、3-三氯甲基苯-1-基(即3-CCl3
Ph-)、4-(3-溴丙-1-基)苯-1-基(即4-BrCH2
CH2
CH2
Ph-)、及其類似物。芳族基團之其他實例包括4-烯丙氧基苯-1-氧基、4-胺基苯-1-基(即4-H2
NPh-)、3-胺基羰基苯-1-基(即NH2
COPh-)、4-苯甲醯基苯-1-基、二氰基亞甲基雙(4-苯-1-基氧基)(即-OPhC(CN)2
PhO-)、3-甲基苯-1-基、亞甲基雙(4-苯-1-基氧基)(即-OPhCH2
PhO-)、2-乙基苯-1-基、苯基乙烯基、3-甲醯基-2-噻吩基、2-己基-5-呋喃基、六亞甲基-1,6-雙(4-苯-1-基氧基)(即-OPh(CH2
)6
PhO-)、4-羥甲基苯-1-基(即4-HOCH2
Ph-)、4-巰基甲基苯-1-基(即4-HSCH2
Ph-)、4-甲硫基苯-1-基(即4-CH3
SPh-)、3-甲氧基苯-1-基、2-甲氧基羰基苯-1-基氧基(例如甲基水楊基)、2-硝基甲基苯-1-基(即2-NO2
CH2
Ph)、3-三甲基矽烷基苯-1-基、4-第三丁基二甲基矽烷基苯-1-基、4-乙烯基苯-1-基、亞乙烯基雙(苯基)、及其類似物。術語「C3
-C20
芳族基團」包括包含至少3個然不超過20個碳原子之芳族基團。芳族基團1-咪唑基(C3
H2
N2
-)表示C3
芳族基團。苄基(C7
H7
-)表示C7
芳族基團。
如文中所用術語「環脂族基團」係指具有至少一價,且包含為環狀然非芳族之原子陣列。如文中定義之「環脂族基團」不包含芳基。「環脂族基團」可包含一或多個非環狀組分。例如,環己基甲基(C6
H11
CH2
-)為包含環己基環(環狀然非芳族之原子陣列)及亞甲基(非環狀組分)之環脂族基團。該環脂族基團可包含雜原子(諸如氮、硫、硒、矽及氧),或可純粹由碳與氫組成。為方便起見,文中定義術語「環脂族基團」包括多種官能基,諸如烷基、烯基、炔基、鹵代烷基、共軛二烯基、醇基、醚基、醛基、酮基、羧酸基團、醯基(例如羧酸衍生物(諸如酯及醯胺))、胺基、硝基、及其類似物。例如,4-甲基環戊-1-基為包含甲基之C6
環脂族基團,該甲基為烷基官能基。類似地,2-硝基環丁-1-基為包含硝基之C4
環脂族基團,該硝基為官能基。環脂族基團可包含可相同或可不同之一或多個鹵原子。鹵素原子包括:例如,氟、氯、溴、及碘。含有一或多個鹵素原子之環脂族基團包括2-三氟甲基環己-1-基、4-溴二氟甲基環辛-1-基、2-氯二氟甲基環己-1-基、六氟亞異丙基-2,2-雙(環己-4-基)(即-C6
H10
C(CF3
)2
C6
H10
-)、2-氯甲基環己-1-基、3-二氟亞甲基環己-1-基、4-三氯甲基環己-1-基氧基、4-溴二氯甲基環己-1-基硫基、2-溴乙基環戊-1-基、2-溴丙基環己-1-基氧基(例如CH3
CHBrCH2
C6
H10
O-)、及其類似物。環脂族基團之其他實例包括4-烯丙氧基環己-1-基、4-胺基環己-1-基(即H2
NC6
H10
-)、4-胺基羰基環戊-1-基(即NH2
COC5
H8
-)、4-乙醯氧基環己-1-基、2,2-二氰基亞異丙基雙(環己-4-基氧基)(即-OC6
H10
C(CN)2
C6
H10
O-)、3-甲基環己-1-基、亞甲基雙(環己-4-基氧基)(即-OC6
H10
CH2
C6
H10
O-)、1-乙基環丁-1-基、環丙基乙烯基、3-甲醯基-2-四氫呋喃基、2-己基-5-四氫呋喃基、六亞甲基-1,6-雙(環己-4-基氧基)(即-OC6
H10
(CH2
)6
C6
H10
O-)、4-羥甲基環己-1-基(即4-HOCH2
C6
H10
-)、4-巰基甲基環己-1-基(即4-HSCH2
C6
H10
-)、4-甲基硫基環己-1-基(即4-CH3
SC6
H10
-)、4-甲氧基環己-1-基、2-甲氧基羰基環己-1-基氧基(2-CH3
OCOC6
H10
O-)、4-硝基甲基環己-1-基(即NO2
CH2
C6
H10
-)、3-三甲基矽烷基環己-1-基、2-第三丁基二甲基矽烷基環戊-1-基、4-三甲氧基矽烷基乙基環己-1-基(例如(CH3
O)3
SiCH2
CH2
C6
H10
-)、4-乙烯基環己烯-1-基、亞乙烯基雙(環己基)、及其類似物。術語「C3
-C10
環脂族基團」包括包含至少3個然不超過10個碳原子之環脂族基團。該環脂族基團2-四氫呋喃基(C4
H7
O-)表示C4
環脂族基團。環己基甲基(C6
H11
CH2
-)表示C7
環脂族基團。
如文中所用術語「脂族基團」係指由非環狀之直鏈或分支鏈原子陣列組成之具有至少一價之有機基團。定義脂族基團包括至少一個碳原子。包含脂族基團之原子陣列可包括雜原子(諸如氮、硫、矽、硒及氧)或可純粹由碳與氫組成。為方便起見,文中定義術語「脂族基團」包括經多種諸如以下之官能基取代之有機基團作為「非環狀之直鏈或分支鏈原子陣列」之部分:烷基、烯基、炔基、鹵代烷基、共軛二烯基、醇基、醚基、醛基、酮基、羧酸基團、醯基(例如羧酸衍生物(諸如酯及醯胺))、胺基、硝基、及其類似物。例如,4-甲基戊-1-基為包含甲基之C6
脂族基團,該甲基為烷基官能基。類似地,4-硝基丁-1-基為包含硝基之C4
脂族基團,該硝基為官能基。脂族基團可為包含一或多個可相同或可不同之鹵素原子之鹵代烷基。鹵素原子包括例如氟、氯、溴、及碘。包含一或多個鹵素原子之脂族基團包括鹵烷基三氟甲基、溴二氟甲基、氯二氟甲基、六氟亞異丙基、氯甲基、二氟亞乙烯、三氯甲基、溴二氯甲基、溴乙基、2-溴三亞甲基(例如-CH2
CHBrCH2
-)、及其類似物。脂族基團之其他實例包括烯丙基、胺基羰基(即-CONH2
)、羰基、2,2-二氰基亞異丙基(即-CH2
C(CN)2
CH2
-)、甲基(即-CH3
)、亞甲基(即-CH2
-)、乙基、伸乙基、甲醯基(即-CHO)、己基、六亞甲基、羥甲基(即-CH2
OH)、巰基甲基(即-CH2
SH)、甲基硫基(即-SCH3
)、甲基硫基甲基(即-CH2
SCH3
)、甲氧基、甲氧基羰基(即CH3
OCO-)、硝基甲基(即-CH2
NO2
)、硫基羰基、三甲基矽烷基(即(CH3
)3
Si-)、第三丁基二甲基矽烷基、3-三甲氧基矽烷基丙基(即(CH3
O)3
SiCH2
CH2
CH2
-)、乙烯基、亞乙烯基、及其類似物。根據另一個實例,C1
-C20
脂族基團包含至少1個然不超過20個碳原子。甲基(即CH3
-)為C1
脂族基團之一實例。癸基(即CH3
(CH2
)9
-)為C10
脂族基團之一實例。
如文中所用術語「雜芳基」係指芳族或不飽和環,其中該(等)芳環中之一或多個碳原子係經雜原子(諸如氮、氧、硼、硒、磷、矽或硫)置換。雜芳基係指可為單芳環、多芳環、或結合至一或多個非芳環之一或多個芳環之結構。在具有多環之結構中,該等環可稠合在一起、共價鍵聯、或鍵聯至共同基團(諸如醚、亞甲基或伸乙基部分)。該共同鍵聯基團亦可為如苯基吡啶基酮中之羰基。雜芳基環之實例包括噻吩、吡啶、異噁唑、吡唑、吡咯、呋喃、咪唑、吲哚、噻唑、苯并咪唑、喹啉、異喹啉、喹喏啉、嘧啶、吡嗪、四唑、三唑、該等基團之苯并稠合類似物、苯并哌喃酮、苯基吡啶、甲苯基吡啶、苯并噻吩基吡啶、苯基異喹啉、二苯并喹喏啉、茀基吡啶、酮基吡咯、2-苯基苯并噁唑、2-苯基苯并噻唑、噻吩基吡啶、苯并噻吩基吡啶、3-甲氧基-2-苯基吡啶、苯基亞胺、吡啶基萘、吡啶基吡咯、吡啶基咪唑、及苯基吲哚。
文中所用術語「芳基」係指芳族取代基,其可為單芳環或經稠合在一起、共價鍵聯、或鍵聯至共同基團(諸如醚、亞甲基或伸乙基部分)之多芳環。該(等)芳環尤其可包括苯基、萘基、蒽基、及聯苯。在具體實施例中,芳基具有介於1與200個之間之碳原子,介於1與50個之間之碳原子或介於1與20個之間之碳原子。
文中所用術語「烷基」係指分支鏈或不分支鏈之飽和或不飽和無環烴基。合適之烷基包括:例如,甲基、乙基、正丙基、異丙基、2-丙烯基(或烯丙基)、乙烯基、正丁基、第三丁基、異丁基(或2-甲基丙基)等等。在具體實施例中,烷基具有介於1與200個之間之碳原子,介於1與50個之間之碳原子或介於1與20個之間之碳原子。
文中所用術語「環烷基」係指具有單環或多稠合環之飽和或不飽和環狀非芳族烴基。合適之環烷基包括:例如,環戊基、環己基、環辛烯基、二環辛基等等。在具體實施例中,環烷基具有介於3與200個之間之碳原子,介於3與50個之間之碳原子或介於3與20個之間之碳原子。
文中引用之任何數值包括從下限值至上限值以一個單位增量之全部值,但限制條件為在任一下限值與任一上限值之間存在至少2個單位之間距。作為一個實例,若陳述組分之量或製程變數(諸如,例如溫度、壓力、時間等等)之值為例如1至90,較佳20至80,更佳30至70,則其意指諸如15至85、22至68、43至51、30至32等等之值明確列舉於本說明書中。就小於1之值而言,一個單位可視情況視為0.0001、0.001、0.01或0.1。此等僅為經明確指明之實例且所列舉之下限值與上限值之間之數值之所有可能組合可視為係以類似方式明確陳述於本申請案中。
在冰冷卻條件下,使正丁基苯胺(50 g,0.34 mol)溶於90 mL AcOH。逐滴添加Ac2
O(40 mL)以確使溫度不會超過30℃。於此之後,接著使反應混合物於40℃下加熱1.5小時。使該混合物冷卻至室溫並注入H2
O(500 mL)中進行沉澱。所沉澱之固體係藉由過濾收集並於真空烘箱中乾燥。使該固體自甲苯(60 mL)/己烷(500 mL)結晶得到無色片狀物(60.1 g)。1
H NMR(400 MHz,CD2
Cl2
,25℃)δ0.92(t,3H),1.35(m,2H),1.56(m,2H),2.10(s,3H),2.57(t,2H),7.12(d,2H),7.32(bs,1H),7.38(d,2H)。
將4,4'-二碘聯苯(26.0 g,64.1 mmol)、正丁基乙醯苯胺(36.8 g,192 mmol)、K2
CO3
(35.4 g,256 mmol)、及二胺配位體(1.38 mL,12.8 mmol)添加至經氮淨化之甲苯溶液(150 mL)中。在使該溶液淨化10分鐘之後,添加碘化銅(1.22 g,6.41 mmol)且在氮氣氛圍下使該混合物回流加熱。在12小時之後,如薄層層析(TLC)(CH2
Cl2
)顯示,該反應完成50%,然後再繼續加熱15小時。使反應混合物冷卻且利用CH2
Cl2
稀釋並過濾。使濾餅經CH2
Cl2
洗滌且使濾液濃縮至乾而得到綠色油狀物。使粗產物固體溶於EtOAc/CH2
Cl2
繼而通過30 cm×10 cm之SiO2
管柱。將合併之溶離份濃縮至乾,接著使該固體自EtOAc結晶2次且在不進行進一步純化下進行下一步驟(29.6 g)。1
H NMR(400 MHz,CD2
Cl2
,25℃)δ0.93(t,6H),1.35(m,4H),1.60(m,4H),2.04(s,6H),2.62(t,4H),7.21(bs,8H),7.31(d,4H),7.55(bs,4H)。
使聯苯醯胺(29.6 g)懸浮於95% EtOH(300 mL)及40% KOH(50 mL)中並回流加熱5小時。冷卻至15℃,然後藉由過濾收集固體且用95% EtOH洗滌,接著在真空烘箱中乾燥得到24.4 g白色結晶固體狀二胺基聯苯。1
H NMR(400 MHz,CD2
Cl2
,25℃)δ0.94(t,6H),1.38(m,4H),1.58(m,4H),2.57(t,4H),5.78(s,2H),7.07(m,12H),7.46(d,4H)。
在添加二胺基聯苯(10 g,22.3 mmol)及1,4-二溴苯(52.6 g,223 mmol)期間,利用氮氣淨化包含二苯基膦基二茂鐵(dppf)(1.15 g,2.08 mmol)及Pd(OAc)2
(233 mg,1.04 mmol)之無水甲苯(PhMe)溶液(150 mL)。在淨化10分鐘之後,添加NaOBut
(6.4 g,66.9 mmol),此舉可使得反應混合物之顏色變綠。在加熱至回流時,該反應混合物之顏色即刻變為血紅色。反應進程係由TLC(10% CH2
Cl2
/己烷)監測,且在4小時之後,TLC顯示反應完全。然後使該反應混合物冷卻至室溫,繼而利用EtOAc稀釋並且藉由巰基官能化SiO2
(4.0 g)處理並攪拌45分鐘。然後使該混合物通過矽藻土床過濾且利用EtOAc洗滌。使濾液吸附於SiO2
上且通過SiO2
(10% CH2
Cl2
/己烷)層析得到白色泡沫狀物(二聚物-溴化物單體,12.6 g)。1
H NMR(400 MHz,CD2
Cl2
,25℃)δ0.94(t,6H),1.37(m,4H),1.59(m,4H),2.58(s,4H),6.95(d,4H),7.02(d,4H),7.08(d,4H),7.12(d,4H),7.33(d,4H),7.46(d,4H)。
將經火焰乾燥之燒瓶置於氮氣氛圍下且注入二聚物-溴化物單體(10.0 g,13.2 mmol)、雙-戊醯二硼烷(10.0 g,39.5 mmol)、無水KOAc(4.0 g,39.5 mmol)、Pd(OAc)2
(65.8 mg,0.29 mmol)、及環己基膦配位體(263 mg,0.64 mmol)。將無水THF(75 mL)添加至該燒瓶且利用氮氣淨化經攪拌之溶液10分鐘,繼而於回流下加熱直到TLC(CH2
Cl2
/己烷)顯示起始之二聚物-溴化物單體不再殘留為止。在此時間點,使反應混合物冷卻至室溫且利用等體積之CH2
Cl2
/己烷(1:1)稀釋,通過矽藻土床過濾,利用CH2
Cl2
/己烷洗滌,然後將濾液濃縮至乾。殘餘物通過利用CH2
Cl2
/己烷(1:1)溶離之SiO2
層析得到4.8 g灰白色泡沫狀物(二聚物-雙硼酸鹽單體)。1
H NMR(400 MHz,CD2
Cl2
,25℃)δ0.95(t,6H),1.31(s,24H),1.38(m,4H),1.61(m,4H),2.59(s,4H),7.03(m,8H),7.11(m,8H),7.48(d,4H),7.60(d,4H)。
溴-(4-己氧基)-苯係於回流下藉由使4-溴酚(91.2 g,527 mmol)與溴己烷(86.0 g,520 mmol)、K2
CO3
(80.0 g,580 mmol)在丙酮(200 mL)中烷化12小時而製得。在藉由過濾移除鹽之後,將反應混合物濃縮至乾而得到油狀物。使該油狀物溶於EtOAc(100 mL)且轉移至分液漏斗繼而利用5% NaOH(4×200 mL)洗滌。將另一份200 mL體積之EtOAc添加至該分液漏斗且容納物利用NaHCO3
(1×200 mL)洗滌且最後經過MgSO4
乾燥。移除該等EtOAc溶劑得到淡黃色油狀物且其可在不進行進一步純化下使用。產率:119 g,89%。1
H NMR(500 MHz,CD2
Cl2
,25℃)δ0.91(t,3H),1.34(m,4H),1.45(m,2H),1.76(m,2H),3.92(t,2H),6.79(d,2H),7.36(d,2H)。
將小片Mg切屑(2.80 g,118 mmol)及接著將無水THF(100 mL)加入乾燥250 mL三頸燒瓶。添加少量碘晶體並於回流下將非均勻混合物加熱15分鐘然後冷卻至室溫。停止攪拌且將1,2-二溴乙烷(0.25 mL)添加至該反應容器。5分鐘後放熱反應跟著發生繼而恢復攪拌20分鐘。然後使反應冷卻至20℃且在使溫度維持於14至18℃之間下於1小時之時間內添加溴-(4-己氧基)-苯(27.8 g,108 mmol)。移走冷卻浴且當該反應之溫度上升至28℃時使反應再多攪拌10分鐘。使該反應冷卻至室溫且藉由移液管將容納物轉移至利用冷卻浴維持於-10℃之經攪拌之2,7,-二溴茀酮(30.0 g,90.4 mmol)之甲苯(250 mL)懸浮液。移走該冷卻浴且使反應混合物於室溫下攪拌20分鐘,隨後利用20 mL EtOH及NH4
Cl飽和溶液(5 mL)處理。將該反應混合物過濾移除不溶性物質繼而轉移至含有EtOAc(100 mL)與H2
O(100 mL)之分液漏斗。使層分離且利用H2
O(2×100 mL)、鹽水(1×100 mL)洗滌有機層,然後經MgSO4
乾燥。移除溶劑至乾而得到粗黃色固狀物(50.8 g)。使該粗物質自己烷/CH2
Cl2
再結晶獲得灰白色微晶物質產物(9-(4-己氧基苯基)-9H-茀-9-醇)。產率:38.6 g,79%。1
H NMR(500 MHz,CD2
Cl2
,25℃)δ0.91(t,3H),1.32(m,4H),1.41(m,2H),1.74(m,2H),2.66(s,1H),3.92(t,2H),6.79(d,2H),7.23(d,2H),7.43(d,2H),7.52(m,4H)。
利用20滴甲磺酸處理苯酚(24 g,256 mmol)與9-(4-己氧基苯基)-9H-茀-9-醇(30.0 g,55.7 mmol)之CH2
Cl2
溶液(75 mL),此舉使得該溶液之顏色變為紫色。使反應於室溫下攪拌直到TLC分析顯示起始茀醇經消耗為止。將該反應混合物轉移至分液漏斗且利用NaHCO3
之飽和溶液(1×200 mL)、H2
O(3×150 mL)洗滌,然後使有機層經MgSO4
乾燥。移除溶劑至乾得到油狀物。使該油狀物自CH2
Cl2
溶液吸附於矽膠上並移除溶劑至乾。將經乾燥之矽膠移至含有裝配於真空燒瓶頂部之矽膠之經填充H2
O漿液(200 mL)之玻璃燒結漏斗(500 mL)頂部。藉由對燒瓶施加真空用H2
O沖洗該漏斗之容納物,此舉可使苯酚自矽膠溶離。在移除過剩的苯酚之後,利用CH3
CN使產物自矽膠溶離。使用旋轉蒸發器利用於45℃下之浴移除溶劑,此舉導致形成乳白色溶液,由該溶液形成白色固狀物。藉由過濾收集產物(9-(4-己氧基苯基)-9'-(4-羥基苯基)-茀),利用水洗滌並乾燥。經分離得到羥基酚加成物之對位與鄰位異構體之混合物(96:10)。產率:34.0 g,98%。1
H NMR(500 MHz,CD2
Cl2
,25℃)δ0.89(t,3H),1.32(m,4H),1.43(m,2H),1.74(m,2H),3.91(t,2H),4.90(s,1H),6.72(d,2H),6.77(d,2H),7.01(d,2H),7.04(d,2H),7.47(d,2H),7.50(d,2H),7.63(d,2H)。
使9-(4-己氧基苯基)-9'-(4-羥基苯基)-茀(33.0 g,53.7 mmol)溶於二甲苯(30 mL),經MgSO4
乾燥,然後過濾。使溶液於旋轉蒸發器上濃縮直到燒瓶容納物重70 g為止。然後將9-(4-己氧基苯基)-9'-(4-羥基苯基)-茀之二甲苯溶液置於氮氣惰性氛圍下並利用碳酸伸乙酯(3.9 mL,59.0 mmol)處理,然後使其回流加熱15小時。於此之後,使反應冷卻至室溫繼而移除溶劑得到黃色油狀物。使該油狀物通過2 L SiO2
層析且利用CH2
Cl2
溶離。在移除溶劑之後,產物(9-(4-己氧基苯基)-9'-(4-(2-羥基乙氧基)苯基)-茀)經分離為無色油狀物。產率29.1 g,82%。1
H NMR(500 MHz,CD2
Cl2
,25℃)δ0.94(t,3H),1.36(m,4H),1.47(m,2H),1.78(m,2H),2.03(t,1H),3.94(m,4H),4.07(t,2H),6.81(d,2H),6.85(d,2H),7.08(d,2H),7.11(d,2H),7.52(d,2H),7.54(d,2H),7.67(d,2H)。
將乙二醇(9-(4-己氧基苯基)-9'-(4-(2-羥基乙氧基)苯基)-茀)(29.1 g,44.2 mmol)之甲苯溶液(200 mL)利用對甲苯磺醯氯(13.3 g,69.8 mmol)及三乙胺(19.4 mL,140 mmol)處理,且在氮氣惰性氛圍下於室溫下攪拌60小時。然後將反應混合物過濾移除三乙胺鹽酸鹽且濃縮至乾。使殘餘物溶於EtOAc且利用5% HCl(1×100 mL)、飽和NaHCO3
(2×200 mL)洗滌,經MgSO4
乾燥,然後移除溶劑至乾燥。使粗油狀物通過1.4 L SiO2
(CH2
Cl2
:己烷,1:1)層析。在移除溶劑之後,產物(9-(4-己氧基苯基)-9'-(4-(2-對甲苯磺醯基乙氧基)苯基)-茀)經分離為白色非晶形固狀物。產率33.0 g,92%。1
H NMR(500 MHz,CD2
Cl2
,25℃)δ0.88(t,3H),1.33(m,4H),1.43(m,2H),1.74(m,2H),2.41(s,3H),3.91(t,2H),4.09(t,2H),4.31(t,2H),6.68(d,2H),6.77(d,2H),7.03(m,4H),7.34(d,2H),7.46(d,2H),7.50(d,2H),7.63(d,2H),7.78(d,2H)。
將固體K2
CO3
(1.00 g,7.24 mmol)添加至經攪拌之含甲苯磺酸化茀(9-(4-己氧基苯基)-9'-(4-(2-對甲苯磺醯基乙氧基)苯基)-茀)(3.00 g,4.00 mmol)與苯甲醯基吡咯銥錯合物([(piq)2
Ir(7)],3.00 g,3.8 mmol)之DMF溶液(25 mL)。使該溶液於80℃下攪拌1.5小時後,使反應冷卻,然後添加H2
O(75 mL)且使所產生之紅色沉澱物經超聲波處理並藉由過濾收集,利用水、MeOH洗滌,然後在空氣中乾燥。在移除溶劑之後,使產物([(piq)2
Ir(7)]-茀單體、或茀染料單體)通過SiO2
:甲苯層析且經分離為紅色固狀物。產率:5.00 g,92%。1
H NMR(500 MHz,CD2
Cl2
,25℃)δ0.89(t,3H),1.33(m,4H),1.42(m,2H),1.73(m,2H),3.90(t,2H),4.27(m,2H),4.34(m,2H),6.30(dd,1H),6.41(dd,1H),6.45(dd,1H),6.51(t,1H),6.77(m,6H),7.00(m,8H),7.19(dd,1H),7.32(d,1H),7.43(d,1H),7.47(d,2H),7.50(dd,2H),7.53(d,1H),7.62(d,2H),7.73(m,4H),7.87(m,1H),7.92(m,1H),7.96(d,2H),8.27(d,2H),8.34(d,1H),8.99(m,2H)。
將三氟乙酸酐(TFAA,10 mL,72.0 mmol)添加至經冷卻至0℃之4-羥基苯甲酸(5.50 g,40.0 mmol)於CH3
CN中之經攪拌懸浮液中。在15分鐘之後,該苯甲酸溶解。將1-(對甲苯磺醯基)吡咯(8.85 g,40.0 mmol)及接著將足量之CH2
Cl2
添加至於0℃下之該經冷卻之溶液中,以使吡咯於此溫度下溶解。將另一份體積之三氟乙酸酐(10 mL,72.0 mmol)添加至該反應混合物,接著在快速攪拌下添加H3
PO4
(2 mL,37.0 mmol)。在使該反應混合物於室溫下攪拌12小時後,添加另一份三氟乙酸酐(6 mL,43.2 mmol)及4-羥基苯甲酸(4.00 g,29.0 mmol)且繼續攪拌12小時。於此之後,移除溶劑至乾且使殘餘物懸浮於5% NaOH(250 mL)中並攪拌過夜。藉由過濾移除該懸浮液繼而利用5% NaOH(250 mL)洗滌濾餅。將NaHCO3
飽和溶液(200 mL)添加至濾液且藉由添加濃HCl使溶液之pH呈中性。生成粉紅色微晶物質且藉由過濾收集,用水洗滌並乾燥。產率(2-(4-羥基苯甲醯基)-吡咯)3.30 g,44%。1
H NMR(500 MHz,CD2
Cl2
,25℃)δ6.35(m,1H),6.90(m,1H),6.94(d,2H),7.14(m,1H),7.87(d,2H),9.70(bs,1H)。
將固態氫化鈉(288 mg,12.0 mmol)添加至經攪拌且經急冷(-10℃)之含酮基吡咯(2-(4-羥基苯甲醯基)-吡咯)(1.20 g,6.40 mmol)之EtOH溶液(100 mL)中,此舉使得溶液顏色從黃色變為橙色。在令該溶液攪拌5分鐘之後,添加[(piq)2
Ir(μ-Cl)]2
(3.33 g,2.56 mmol),然後使混合物回流加熱10小時。使反應混合物冷卻至室溫且藉由過濾收集紅色沉澱物。利用EtOH洗滌產物([(piq)2
Ir(7)])且在空氣中乾燥。產率(3.85 mg,96%)。1
H NMR(500 MHz,CD2
Cl2
,25℃)δ6.32(dd,1H),6.42(dd,2H),6.45(dd,1H),6.51(t,1H),6.73(m,1H),6.78(m,1H),6.83(d,2H),7.00(m,2H),7.18(dd,1H),7.31(d,1H),7.43(d,1H),7.53(d,1H),7.73(m,4H),7.89(m,4H),8.27(m,2H),8.34(d,1H),8.99(m,2H)。
聚合物係根據示意圖1製備且所用物質示於表1。
在使用之前,使配位體1自丙酮再結晶。在稱量之前,所有單體係在真空烘箱中於50℃下乾燥至少2小時。該配位體1為Aldrich編號638072之具有如下結構之2-二環己基膦基-2',6'-二甲氧基聯苯。
在三頸圓底燒瓶(25或50 mL)中,稱量Pd(OAc)2
及配位體1。將三種單體與10 mL甲苯一起添加至該燒瓶。於溫和攪拌下,在所有單體溶解之後,利用氬氣流使該溶液除氣15分鐘。同時在另外的小瓶中,稱量Et4
NOH水溶液(20%),並將其轉移至添加漏斗內且另外利用氬氣進行除氣。在除氣至少15分鐘之後,以逐滴方式將該水溶液添加至有機溶液。
然後將燒瓶浸於75℃油浴中。於正氬氣壓力下攪拌並加熱24至48小時。
在利用凝膠滲透層析法(GPC)分析聚合物之後,添加在2 mL甲苯(先前經除氣)中之0.5 mL苯基酸1,3-丙二醇酯。使反應溶液維持於75℃下又1小時。於此之後,將其自熱移除且轉移至氮氣箱。
所有溶劑係利用氬氣進行除氣。所有玻璃器皿及管係經乾燥且於分離之前晚置於氮氣淨化箱內。
在快速攪拌下將溫熱的聚合物溶液逐滴添加至3倍體積之丙酮溶液中。在傾倒除去上清液之前,使溶液保持靜止,然後將殘餘物轉移至離心管,且以鋁箔包裹。在離心之後,將該等管移至氮氣淨化箱中以傾倒除去溶劑。將經分離之粉末轉移至小瓶且再溶解於熱甲苯(~0.5 g聚合物利用約15-20 mL甲苯)。然後將4倍量之經胺官能化之矽膠添加至該溶液,且於加熱板上在70至90℃下攪拌以使該聚合物保持溶液形式1小時。使該溶液透過凹槽形濾紙進行過濾。使用約10至20 mL之熱甲苯來洗滌殘餘物且幫助轉移。將丙酮添加至該經過濾之聚合物溶液直到其變渾濁為止。然後在將渾濁上清液自膠體固狀物傾倒除去之前,使該溶液靜置。添加熱甲苯以使殘留於先前燒瓶之該膠體固狀物再溶解,然後將4倍體積之丙酮溶液逐滴添加至該溶液。藉由離心收集聚合物,用純丙酮洗滌,然後再次離心並傾倒除去丙酮。重複此洗滌步驟2次,此後使聚合物粒塊於手套箱中乾燥過夜。隔天分析重量(0.8 g)及Mw(50344 g/mol,PDI=2.61)。
分子量數據係採用具有UV/VIS檢測器之Perkin Elmer GPC系列200、Polymer Laboratories PLGel 5 mm管柱、具有3.75% IPA之氯仿作為溶離劑或THF作為溶離劑及聚苯乙烯標準品作為校準標準品而獲得。1
H NMR譜係於Bruker 400或Bruker Advance 500光譜儀上測得並相對殘餘溶劑位移進行參照。
雖然文中僅說明及描述本發明之若干特徵,然熟習此項相關技術者當明瞭多種修改及變化。因此,應瞭解隨附申請專利範圍旨在涵蓋所有屬於本發明真實精神範圍內之該等修改及變化。
Claims (20)
- 一種含有如下式I之結構單元之聚合物:
- 如請求項1之聚合物,其中Ar1 係選自
- 如請求項1之聚合物,其中Ar2 係衍生自二溴9,9-二辛基茀單體。
- 如請求項1之聚合物,其中L係衍生自苯基異喹啉。
- 如請求項1之聚合物,其包含如下式II之結構單元:
- 如請求項1之聚合物,其包含如下式III之結構單元:
- 如請求項1之聚合物,其包含如下式IV之結構單元:
- 如請求項1之聚合物,其包含衍生自以下之結構單元:
- 一種光電裝置,其包括如請求項1之聚合物。
- 如請求項9之光電裝置,其中該聚合物包含如下式II之結構單元:
- 如請求項9之光電裝置,其中該聚合物包含如下式III之結構單元:
- 如請求項9之光電裝置,其中該聚合物包含如下式IV之結構單元:
- 如請求項9之光電裝置,其中該聚合物包含衍生自以下之結構單元:
- 如請求項9之光電裝置,其中該聚合物包含衍生自以下之結構單元:
- 如請求項9之光電裝置,其中該聚合物包含衍生自以下之結構單元:
- 如請求項9之光電裝置,其中該聚合物包含衍生自以下之結構單元:
- 如請求項9之光電裝置,其中Ar1 係選自
- 如請求項9之光電裝置,其中Ar2 係衍生自二溴9,9-二辛基茀單體。
- 如請求項9之光電裝置,其中L係衍生自苯基異喹啉。
- 如請求項9之光電裝置,其包括多於一個發光層,且其中此等多於一個發光層中之至少一層包含聚合物。
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