TWI354693B - Organic light emitting devices - Google Patents
Organic light emitting devices Download PDFInfo
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- TWI354693B TWI354693B TW093108931A TW93108931A TWI354693B TW I354693 B TWI354693 B TW I354693B TW 093108931 A TW093108931 A TW 093108931A TW 93108931 A TW93108931 A TW 93108931A TW I354693 B TWI354693 B TW I354693B
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- 239000000725 suspension Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 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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Description
1354693 玖、發明說明： 【發明所屬之技術領域】 本發明有關有機發光裝置（0LEDs)，尤其有關使用於該等 裝置中之-光有機-金屬材料。詳言之，本發明有關 〇LEDs，其中該發光層係包含具有複數個金屬中心之磷光 發光材料。 【先前技術】 利用有機材料之光電子裝置因數項因素而需求漸高。許 多用以製造該等裝置之材料相對平價，故有機光電子裝置 相對於無機裝置具有成本優勢之潛力。此外，有機材料之 固有性質（諸如其可撓性），使其極適於特定心（諸如製造 於可撓性基材上）。有機光電子裝置之實例包括有機發光裝 置（〇LEDs)'有機光電晶冑、有機光電伏打電池、及有機光 檢波器。就QLEDs而言，該有機材料可具有優於習用材料 之性能。例如，有機發光層發射光之波長通常以適當之換 雜劑即可調整。 本發明所使用之"有機物"一辭係包含聚合物材料及可用 ，有機光電子裝置之小分子有機材料。，，小分子，，表示 非聚合物之任何有機材料，而"小分子"實際上可相當的 大。小分子於某些情況下可包含重現單元。例如，使用長 鏈院基作為取代基並不會使分子被剔除於,,小分子"之群 2小分子亦可捧入聚合物内’例如作為聚合物主鏈上之 作為_之—料”!'分子料料㈣狀體之核 。刀，該樹枝狀體係由建構於該核心部分上之一系列化 92427.doc 1354693 學外殼所組成。樹枝狀體之核心部分可為螢光或磷光小分 子發光劑。樹枝狀體可為"小分子"’且相信目前使用於 OLEDs領域中之所有樹枝狀體皆為小分子。 OLEDs係利用在該裝置兩端施加電壓時發光之有機薄 膜。OLEDs變成使用於諸如平板顯示器、照明及後照光之 應用中愈來愈受重視之技術。有數種〇LED材料及結構係描 述於於美國專利第5,844,363號、第6,303,238號及第 5,707,745號t，以引用方式將全文内容併入本文。 OLED裝置.通常（但非始終）係經由至少一電極發射光 線，有機光電子裝置中可使用一或多個透明電極。例如， 透明電極材料，諸如氧化銦錫（IT〇)，可作為底電極。亦可 使用透明頂電極，諸^& 名如美國專利第5,703,436號及第 5,707,745號所揭示，以引用方七 5丨用方式將全文内容併入。對於預 定僅經由底電極發光之梦罢二a ^ 、 f尤之裝置而έ，該頂電極不需透明，且 可包含具有高度電導係怒夕s 电净係数之反射性厚金屬層。相同地， 經僅由頂電極發光之裝置而^ — — & 浐置而吕，该底電極可為不透明且/ 反射性。當電極不需透明技 一 時，使用反射性電極可藉由將 線反射回該透明電極而谗Α 九 而増加經由另-電極發射之光量。亦 可製造完全透明裝置，复中 方 蘇㈣OLED B 〃中兩電極白透明。亦可製造侧面 發先型OLEDs，且該等裝置 囬 甲之或兩電極可為不透明七 為反射性。 η个适明或 本發明所使用之”項”伤矣_ 貝係表不離該基材最遠，而，，底 最接近該基材。例如，i 低係表不 洗具有兩電極之裝置而言， 係為最接近基材之電極， 底電極 通吊係為所製造之第—電極。低 92427.doc 1354693 •極具有兩表面，底表面最接近該基材，頂表面最遠離該 基材。當第-層被描述為m第二層上，，時，該第一層 係配置成最遠離基材1第—及第：層之間可有其他層: 除非表明該第一層係與該第二層”物理性接觸"。例如，一 陰極可描述成"配置於-陽極上，•，即使其时各種有機層。 【發明内容】 提供具有一陽極、一陰極及一配置於該陽極及陰極之間 且電連於該陽極及陰極之發光層的裝置。該發光層係包含 具有多於一金屬中心之發光材料。於一具體實例中，第一 及第一金屬中心係個別選自由d7、d8及d9金屬所組成之 群。橋連配位體係配位於該第一金屬中心及該第二金屬中 ^於具體貫例中，該第一及第二金屬中心各具有至少3 之配位數，更佳情況係各具有4之配位數。於一具體實例 中，感光性配位體係配位於該第一及第二金屬中心。於一 具體實例中，無感光性配位體。於一具體實例中，提供電 中性雙核發光材料。於一具體實例中，該第一及金屬中心 係具有共面構型，最好是正方平面共面構型。於一具體實 例中，該金屬中心係選自具有大於或等於40之原子序的金 屬。 【實施方式】 通常，OLED係包含至少一層配置於一陽極與一陰極之間 且電連於該陽極及該陰極之有機層。本發明所使用之”配置 於…之間且電連於…"並非表示所示薄層必須相鄰並直接 接觸。而可於所示薄層之間配置附加薄層。施加電流於該 92427.doc 1354693 裝置時’陽極注射電洞且陰極注射電子至該有機層（等）内 所注射之電洞及電子各向著具有相反電荷之電極移動。當 電子及電洞定域於相同分子時，形成了 "激子"，即具有： 發能態之定域電子-電洞對。當激子經由光電放射機制他張 牯發出光線。在某些情況下，該激子可定域於一激態二聚 物—Γ)或激態錯合物（exciplex)上。亦可能發生 機制，諸如熱弛張，但通常視為非期望狀況。 原始OLEDs使用自其單重態發光（”螢光"）之發光分子，如 例如美國專利.第4,769,292號所揭示，以引用方式全文併作 參考。螢光發射通常在短於10毫微秒之時段内發生。 最近，已出示具有自三重態發光（”磷光”）之發光材料的 OLEDs。Bald0 等人，"Highly Efficient Ph〇sph〇rescent Emission from Organic Electroluminescent Devices," Nature v〇l. 395, 15 1-154, 1998; ("Baldo-I") and Baldo等人，"Very high- efficiency green organic light-emitting devices based on electrophosphorescence," Appl. Phys. Lett., vol. 75, No. 3, 4-6 (1999)(”Baldo-II")，以引用方式全文併入本中。磷光 可稱為"禁帶”躍遷，因為該躍遷需要改變自旋狀態，而量 子力學顯示不利於該躍遷。結果，填光通常在超過至少1〇 毫微秒之時段内發生，通常大於1〇〇毫微秒。若磷光之天然 轄射期太長，則三重態可能藉由非輻射機制衰變，故不發 光。有機磷光亦經常在處於極低溫下之含有具未共用電子 對的雜原子之分子中見到。2,2'-聯吡啶係為該種分子。非 輻射衰變機制一般係溫度相依性，故在液態氮溫度下具有 92427.doc 1354693 磷光之材料無法於室溫下具有磷光。然而，如Baldo所示， 此項問題可藉著選擇在室溫下發磷光之磷光化合物而得到 解決。 通常’相信OLED中之激子係於約3:1比例下產生，即， 約75%三重態及25%單重態。參照，Adachi等人，”Nearly 100% Internal Phosphorescent Efficiency In An Organic
Light Emitting Device，" J. Appl. Phys.，90, 5048 (2001)，以 引用方式將全文併入。在許多情況下，單重態激子經由"系 統間跨越（intersystem crossing)”即可將其能量躍遷成三重 激態’而三重態激子則無法立即將其能量躍遷成單重激 態。結果，使用磷光OLEDs理論上可有1 〇〇%内部量子效率。 在螢光裝置中，三重態激子之能量通常損失於非輻射衰變 過知’將該裝置加熱’導致遠較為低之内部量子效率。採 用自三重激態發射之磷光材料的〇LEDs係揭示於例如美國 專利第6,303,238號中，以引用方式全文併入。 磷光可能發生在產生發射衰變之自三重激態到達中間非 二重態的躍遷之前。例如，配位於鑭系元素之有機分子經 常自定域於該鑭系金屬上的激態發射磷光。然而，該等材 料並非直接自二重激態發射磷光，而是自位在鑭系金屬離 子中。之原子激態發射。二酮銪（eur〇pium d丨錯合 物係例示此等類型中之一種。 來自三重態之磷光可藉著將有機分子侷限（以經由鍵結 為佳）於冋原子序之原子附近而強於瑩光。此種稱為重原子 效應之現象係因為稱為自旋軌道耦合之機制而產生。該種 92427.doc 1354693 磷光躍遷可在.自有機金屬分子諸如三（2_苯基吡啶）銥（m) 之激態金屬-對-配位體電荷轉移（MLCT)的狀態中發現。 圖1出示有機發光裝置1〇〇。圖中並未完全按照比例繪 製。裝置100可包括一基材110、一陽極115、一電洞注射層 120、一電洞傳遞層125、一電子阻隔層13〇、一發光層135、 一電洞阻隔層140 ' —電子傳遞層145、一電子注射層15〇、 一保護層155、及一陰極160。陰極16〇係為具有一第一導電 層162及一第二導電層164之複合陰極。裝置1〇〇可藉著依序 沉積所述薄層.而製得。 基材110可為提供所需之結構性質的任何適當之基材。基 材110可為可撓性或剛性。基材11〇可為透明、半透明或不 透明β塑料及玻璃係為較佳剛性基材的實例。塑料及金屬 箔係為較佳可撓性基材的實例。基材110可為半導體材料， 利於電路之製造。例如，基材110可為矽晶圓，其表層製有 電路，可控制後續沉積於該基材上的OLEDS ◊可使用其他 基材。基材110之材料及厚度可經選擇，以得到所需之結構 及光學性質。 陽極115可為任何充分導電以將電洞傳遞至該有機層的 適當陽極。陽極115之材料最好具有高於約4電子伏特之功 函數（"高功函數材料·}較佳陽極材料係包括導電性金屬氧 化物，諸如氧化銦錫（IT0)及氧化銦鋅（IZ〇)、氧化物鋁鋅 (AIZnO)及金屬。陽極115(及基材u〇)可充分透明以產生 底部發光型裝置。較佳透明基材及陽極組合物係沉積於玻 璃或塑料（基材）上之市售IT0(陽極）。可撓性且透明之基材_ 92427.doc 1354693 陽極組合物係揭示於美國專利第 $，844’363唬中’以引用方 式王文併入。％極115可為不透明且/或反射性。反射性陽 極115可能有利於某些頂部發光型增加自裝置頂部發射之 光量。陽極m之材料及厚度可經選擇， 性及光學性質1陽極115係透料，特定材料可有一厚度 範圍，厚至足以提供所需之電導係數，但薄至足以提供； 需之透明纟。可使用其他陽極材料及結構。 電洞傳遞層125可包含可傳遞電洞之材料。電洞傳遞層 130可為本質(.未經摻雜）或經摻雜1雜可心增進電導係 數。a_NPD及™係為本質電洞傳遞層之實例。P型摻雜之 電洞傳遞層的-實例係為摻雜有莫耳比為5〇:1之^丁卿 的膽鳩，如Forrest等人之美國專利申請案序號 1 0/1 73,862所揭不’以引用方式全文併入。可使用其他電洞 傳遞層。 發光層135包含至少一種在陽極i 15與陰極⑽之間通以 電流時可發光之發光材料。發光層135較佳含㈣光發射材 料唯亦可使用螢光發射材料。鱗光材料係因為該等材料 之較高發光效率而較佳。發光層135亦可包含—宿主材料， ’播雜有可捕捉電子電洞、及/或激 子之發光材料’使激子經由光電放射機制而自發光材料弛 張。發光層135可包含單—種综合有傳遞及發光性質之材 料。不論該發光材料係摻雜劑或主要組份，發光層135皆可 包含其他材料，諸如調整該發光材料之發射的摻雜劑。發 光層135可包含多種發光材料，其可結合而發射所需光譜之 92427.doc -12- 1354693 光。因此，在本發明之一具體實例中，該發光層係包含雙 核發光材料及第二發光材料，使得結合之發射 足以跨越可 見光譜，而生成白光。螢光發射材料之實例包括DCM& DMQA。宿主材料之實例係包括Alq3、BNp&mCp。發光及 佰主材料之實例係指述於Th〇mpSon等人之美國專利第 6,303,238號中，以引用方式全文併人。發光材料可依數種 方式c 3於發光層135中。例如，發光性小分子可摻入聚合 物中。可使用其他發光層材料及結構。 電子傳遞層140可包括可傳遞電子之材料。電子傳遞層 140可為本質（未摻雜）或經摻雜。摻雜可用以增進電導係 數。蝴3係為本f電子傳遞層之實例。η型摻雜之電子傳遞 層的實例係為摻雜有莫耳比為丨：丨之u的Bphen，如 等人之美國專利申請案序號1〇/173,682中，以引用方式全文 併入。可使用其他電子傳遞層》 該電子傳遞層之電荷載流成份可加以選擇，使得電子可 自該陰極充分注射至該電子傳遞層之圖〇(最低未佔用分 子軌道)能階内。"電荷載流成份”係為具有實際傳遞電子之 LUMO的材料。此種成份可為基f材料，或可為摻雜劑。有 機材料之LUM0能階通常可由該材料之電子親和力定性，而 ，極之相對電子注射效率通常可㈣陰極材料之功函數來 疋性。此意、為電子傳遞層及相鄰陰極之較佳十生質可就★亥 饥之電荷載流成份的電子親和力及該陰極材料之功函： ^其，為達到高度電子注射效率，陰極材料之功函 數最好未較電子傳遞層之電荷載流成份的電子親和力高出 92427.doc 1354693 約0.75電子伏特以上，未高出約〇5電子伏特以上更佳。該 電子傳遞層之電荷載流成份的電子親和力最好大於陰極材 料之功函數。相同考慮亦適用於欲注射電子之任何層。 陰極160可為任何技術界已知之材料或材料組合物，使得 陰極160可傳遞電子’並將其注射至裝置！⑽之有機層内。 陰極160可為透明或不透明，且可為反射性。金屬及金屬氧 化物係為適當之陰極材料的實例。陰極16〇可為單一層，或 可具有複合結構。ΒΠ出示具有薄金屬層162及較厚導電性 金屬氧化物層164的複合陰極16〇。在複合陰極中，較厚層 164之較佳材料係包括ΙΤ〇、ΙΖ〇及其他技術#已知之材料曰。 以引用方式全文併入之美國專利第5 7〇3 436號及第 5,707,745號揭示包括複合陰極之陰極實例，該複合陰極具 有金屬薄層諸如Mg:Ag，且覆有透明、導電性、濺鍍沉積 之1T〇層。陰極160與底層有機層接觸之部分，不論是單層 陰極160、複合陰極之金屬薄層162、或某些其他部分皆 以具有低於約4電子伏特之材料（"低功函數材料，，）製得為 佳。可使用其他陰極材料及結構。 阻隔層可用以減少脫離該發光層之電荷載體（電子或電 洞）及/或激子的數目。電子阻隔層13〇可配置於發光層135 與電洞傳遞層125之間，以阻隔電子在電洞傳遞層125方向 上脫離發光層135。相同地，電洞阻隔層14〇可配置於發光 層135與電子傳遞層145之間，以阻隔電洞於電子傳遞層丨4〇 方向上脫離發光層135。阻隔層亦可用以阻隔激子擴散離開 該發光層。阻隔層之理論及用途係詳述於F〇rrest等人之美 92427.doc -14- 1354693 國專利第6,097，147號及美 中’以引用方式全文併入。 國專利申請案序號1〇/173,682 通承’’主射層包含可改善自—層（諸如一電極或—有機層） 將電荷載體注射至相鄰有機層内之材料 電荷傳遞功能。裝置10。中，電洞注射層m可為改= 極出至電洞傳遞層125内之電洞注射的任何層。We係為 可作為自汀〇陽極115及其他陽極之電洞注射層。裝置ι〇〇 令’電子注射層15〇可為改善進入電子傳遞層145内之電子 注射的任㈣。LiF/竭為可作為自相鄰層進人電子傳遞 層内之電子注射層的材料。其他材料或材料組合物可使用 於注射層。視特定裝置之結構而定，注射層可配置於異於 圖100所不之位置上。注射層之其他實例係提供於等人之 美國專利申請案序號09/93 i，948中，以引用方式全文併入。 電洞注射層可包含溶液沉積材料，諸如旋塗之聚合物，例 如PEDOT.PSS ’或其可為氣相沉積小分子材料，例如〔up。 或 MTDATA。 電洞注射層（mL)可用以平面化或潤濕陽極表面，及提供 自陽極進入電洞注射材料内之有效電洞注射。電洞注射層 亦可含有具homo(最高佔用分子軌道）能階之電荷載流成 份，該能階有利地配合（如其中所述之相對電離勢（IP)能所 定義）位於HIL之一側上的相鄰陽極層及位於HIL相反側上 之電洞傳遞層。該"電荷載流成份"係為產生實際傳遞電洞 之homo的材料。此成份可為HIL之基質材料’或其可為摻 雜劑。使用經摻雜之HIL容許針對電性質來選擇該摻雜劑， 92427.doc •15- 1354693 而針對形態性質諸如㈣、可繞性、勤性等來選擇宿主材 料。飢材料之較佳性質係使得電洞可有效地自陽極注射Γ p材㈣。尤其，亂之電荷載流成份較好係 :=不超過約。·7電子伏特之-該電荷载流成份 厂、有較_極材料大不超過狀5電子伏特之ιρ更佳。相 同考慮適詩欲注射電洞之任何層。肌材料與—般使用於 ▲OLED之電洞傳遞層的習用電洞傳遞材料的進—步區別是 細L材料可具有實質上低於習用電洞傳遞材料之電洞傳 導性的電洞傳導性。本發明肌之厚度可厚至足以幫助平面 化或濁濕陽極層表面。例如，對極光滑之陽極表面而言， 可接受低達iG奈米之肌厚度。然而，因為陽極表面傾向極 為粗經，故某些情況可能期望有高達5G奈米之HIL厚度。 保護層可用以在後續製造過程中保護底下薄層。例如， 用以製造金屬或金屬氧化物頂電極之方法可能損傷有機 層’保護基層可用以降低或消除該種損傷。在裝置ι〇〇中， 保護層155可減少底層有機層在陰極16〇製造期間的損傷。 杈佳情況是保護層對於其傳遞之載體類型（裝置丨〇〇為電子） 具有高載體移動性，故不會大幅增加裝置1〇〇之操作電壓。 CuPc、BCP、及各種金屬乃花青係為可使用於保護層之材 料的實例。可使用其他材料或材料組合物。保護層155之厚 度最好係厚至足以使底下薄層幾乎或完全不會因為在沉積 有機保護層160之後所進行之製造過程而損傷，但卻不致厚 至大幅增加裝置1〇〇之操作電壓。保護層155可經摻雜，以 增加其電導係數。例如’ CuPc或BCP保護層ι6〇可摻雜Li。 92427.doc • 16 - 1354693 保護層之更詳細描述可參考Lu等人之美國專利申請案序號 09/931，948中，以引用方式全文併入。 圖2出示倒置之〇lED2〇〇。該裝置包括一基材21〇,—陰 極215 ’ 一發光層220，一電洞傳遞層225 ’及一陽極23〇。 裝置200可藉著依序沉積所述薄層而製得。因為最常用之 OLED構型係具有一配置於該陽極上之陰極，而裝置2〇〇具 有配置於陽極230下方之陰極215，故裝置200可稱為"倒 置"OLED。與裝置100所述相同之材料可使用於裝置2〇〇之 對應薄層中。.圖2提供某些層如何可自裝置ι〇〇之結構略去 某些層的一實例。 圖1及2所說明之簡易層狀結構係以非限制實例提供，應 明瞭本發明具體實例可與各種其他結構結合使用。所述之 材料及結構係例示性質，可使用其他材料及結構。功能性 OLEDs可藉著以不同方式結合所述各種薄層而達成，或可 基於設計、性能及成本因素而完全略去薄層。亦可包括其 他未詳述之薄層。可使用除詳述者外之材料。雖然此處提 供之實例中許多皆將各種薄層描述為包含單一材料，但應 明瞭可使用材料之組合物，諸如宿主成份與掺雜劑之混合 物，或更平常之混合物。而且，該薄層可具有各種子層： 此處賦予各種薄層之名稱並非意圖嚴格限制。例如，在裝 置200中，電洞傳遞層225傳遞電洞’且將電洞注射至發二 層220内，且可描述為電洞傳遞層或電洞注射層。— 例中’ OLEDT描述為具有夾置於_陰極與 ”有機層”。此有機層可包含單—層，或 之曰之 步包含多個 92427.doc -17· 1354693 不同有機材料層’如例如圖1及2所述。 未詳述之結構及材料亦可使用’諸如包含聚合物材料之 OLEDs (PLEDs)，諸如Friend等人所揭示之美國專利第 5,247，190號中，該案以引用方式全文併入》進_步實例， 可使用具有單一有機層之OLEDs ^ OLEDs可為疊層，例如 Forrest等人之美國專利第5,7〇7,745號所描述，以引用方式 全文併入。該OLED結構可脫離圖1及2所說明之單純層狀結 構。例如，該基材可包括一傾斜之反射性表面，以改盖外 搞合（out-coupling) ’諸如Forrest等人之美國專利第 6,091,195號所述之台面結構（mesa structure)，及/或Bul〇vic 等人之美國專利第5,834,893號所述之坑槽結構（沖 structure)，以引用方式全文併入。 除非另有陳述’否則各個具體實例之任何層皆可藉任何 適當之方法沉積。就有機層而言，較佳方法包括熱蒸發； 喷墨’諸如美國專利第6,013,982號及第6,087，196號所述， 以引用方式全文併入；有機氣相沉積（0VPD)，諸如F〇rrest 等人之美國專利第6,337，102號所描述，以引用方式全文併 入，及有機蒸汽贺射印刷（OVJP) ’諸如美國專利申請案編 號10/233,470所描述，以引用方式全文併入。其他適當之沉 積方法包括旋塗法及其他以溶液為主之方法。以溶液為主 之方法以於氮或惰性氛圍中進行為佳。就其他層而言，較 佳方法係包括熱蒸發。較佳圖案化方法包括經由光罩來沉 積；冷焊’諸如美國專利第6,294,398號及第6,468,819號所 描述，以引用方式全文併入；及綜合某些沉積方法諸如噴 92427.doc •18- 1354693 •及cmD之㈣化。其他方法亦可使用。欲沉積之材料可 ，修飾，以使其與特定沉積方法相容。例如，取代基諸如 /刀支鏈或未分支鏈、城佳含有至少3個碳之貌基及芳基， 可使用於小分子中’以增進其進行溶液加工之能力。可使 用具有20個碳或以上之取代基，而3至2〇個碳係為較佳範 圍。具有不對稱結構之材料可具有優於具有對稱結構者之 溶液加工性，因為不對稱材料可具有較低之再結晶傾向。 樹枝狀體取代基可用以增進小分子進行溶液加工之能力。 本發明具體實例所製造之裝置可收納於各種商品中，包 括平板顯示器、電腦螢幕、電視、廣告板、内部或外部照 明及/或信號用之燈具、平視型顯示器、全透明顯示器、可 撓性顯示器、雷射印表機、電話、行動電話、個人數位助 (PDAs)膝上型電腦、數位照相機、照相攝影機、觀景 窗、微型顯示器、交通工具、大型牆、劇院或體育館螢幕： 或標諸。各種控制機制皆可用以控制本發明所製造之裝 置’包括被動陣列及主動陣列。許多裝置意圖使用於對人 類舒適之溫度範圍’諸如肌至贼，室溫至坑）更佳。 此處所描述之材料及結構可於除〇LEDs以外之裝置中具 有應用。例如，其他光電子裝置諸如有機太陽能電池及有 機光檢波器可採用該等材料及結構。更廣泛言之，有機裝 置諸如有機電晶體可採用該等材料及結構。 本發明所使用之"溶液可加工”係表示可於液體介質中溶 解、分散、或傳遞且/或自該液體介質沉積，或為溶液或為 懸浮液形式。 92427.doc -19· 1354693 本發明所使用之”雙核 中心之錯合物。本發明>1 一辭係表示實際上具有兩個金屬
性"配位體。鍵 位體之外，各金屬中心亦鍵結於至少一 ”感光 鍵結於各金屬中心之配位體可使該金屬中心具 有約略正方平面構型。本發明部分具體實例中，可有多於 兩個金屬中心，但該等具體實例非以"雙核"描述。 本發明具體實例之發光材料可包含至少一"橋連配位體"。 此配位體係稱為橋連，因其鍵結於兩個不同之金屬中心。 該橋連配位體（等）可鍵結於兩金屬中心，使得該兩金屬中心 接近，一般在約4 A内。介於金屬中心之間4 A或更小之距 離使彳寸個別金屬原子之d-軌道大幅重疊。雙核錯合物之兩 金屬中心以相隔約2.5至約2.8 A為佳。橋連配位體之選擇使 得介於兩金屬中心之間的距離可容許調整。藉著改變橋連 配位體，可調節該雙核錯合物之發射能量。 部分具體實例中，兩金屬中心可藉一或多個橋連配位體 鍵合成為共面構型。共面構型較佳，因為介於金屬中心之 間的距離及因而所導致之分子發射光譜於共面構型中更可 立即調節。例如’視橋連配位體之選擇而定，共面構型可 導致2 Α或更小之金屬-金屬距離。如此小的距離在使用非 共面之構型時可能難以達成。”共面”係表示各金屬中心有 至少三個鍵結’界定一垂直於介於該兩金屬中心之間之車由 的平面。較佳共面構型係為正方平面兩面構型，其可例如 92427.doc • 20· 1354693 以d8金屬達成。在該正方平面構型中，各金屬中心係具有 四個鍵結，皆約略位於相同平面，且彼此分開約9〇度。圖 10及11所出示之（F2Ppy)2Pt2(SPy)2係為正方平面兩面雙核 金屬化合物的實例。 該等金屬中心以非第一列過渡金屬為佳，而是選自元素 週期表之第二列金屬或更高列，即原子序大於或等於4〇之 金屬。選自第二列或更高列之金屬具有較高之自旋執道輕 合’產生具有較尚鱗光產率的發光材料。 部分具體實例係具有與兩金屬中心配位之感光性配位 體。該等具體實例之發光可藉著使用該橋連配位體來達到 且控制介於兩個配位於不同金屬巾心之感光性配位體的π 軌道之間的相互作用’而進行調整。相信若兩感光性配位 體保持在3·5 Α或更小距離下，則其間會產生有效之η相 互作用。 亦佳情況是該橋連配位體無法作為雙配位基配位體。因 此，較佳«擇該橋連配位體，使得該鍵結部位優先鍵結 於兩個不同之金屬中心’而非鍵結同-個金屬中心。 該橋連配位體可稱為"㈣"，目相信其可修飾分子之感 光性，與直接產生感光性不同。然而，該橋連配位體可為 該發光系統之-部分。感光性及輔助之定義係預定為非限 制理論。 該橋連配位體於雙核發光性化合物之兩金屬中心之間提 供安定之鍵合。該橋連配位體可為對稱（即，對於該等金屬 中心之鍵結部位㈣）或不對稱（即，對於料金屬中心之鍵 92427.doc -21 . 1354693 結部位不相等卜因此，該橋連配位體係為具有至少兩個用 於配位之部位。適當之橋連配位體可選自技術界已知可提 供安定之雙核物種者。本文中，安定一辭係表示該雙核錯 合物在摻入發光裝置内時的安定性，尤其是該裝置進行操 作期間。部分適當之配位體係揭示於：Matsumoto等人， "Organometallic chemistry of platinum-blue derived plationumlll dinuclear complexes, "Coordination Chemistry Reviews 231 (2002)，第 229 至 238 頁及 Tejel 等人，"From Platinum Blues to Rhodium and Iridium Blues, " Chem. Eur. J· (1999) 5, No. 4,第 1131 至 1135 頁；Belitto等人，"Metal-Metal Interactions in one Dimension. 3. Segregated Canted Stacks of Tetrakis (dithioacetato) diplatinum (11)," Inorg. Chem. (1980) 19,第 3632 至 3636 頁；Oskui 等人，"Di-and Tripalladium(II) and -platinum(II) Complexes Containing 7-Ami no -1,8-naphthyridin-2-one as a Bridging Ligand-Oxidation of a [Pt3]6+ Core to [Pt3]8 + , " Eur. J. Inorg. Chem. (1999) 1325-1333 ; Navarro等人 ’ "Binuclear Platinum (II) Triazolopyrimidine Bridged Complexes. Preparation, Crytal Structure, NMR Spectroscopy, and ab Initio MO Investigation on the Bonding Nature of the Pt(II)....Pt(II) Interaction in the Model Compound {Pt2[NHCHN(C(CH2) (CH3))]4}，" Inorg. Chem. (1996) 35，7829-7835 ; Lewis等 人，"Oligomerization and Two-Center Oxidative Addition Reactions of a Dimeric Rhodium(l) Complex," J. Am. Chem. 92427.doc -22- 1354693
Soc_ (1976) 98, 746卜7463 ’各以引用方式併入。 本發明較佳具體實例中，橋連配位體（等）係為通式ΠΙ之 化合物 (m) 其中X及Y係選自可對金屬中心形成供給性鍵結之原子或 β为’且B係為五-或六-員壤。虛線係表示選擇性雙鍵。較 佳橋連配位體係包括·：
及其衍生物。其他較佳橋連配位體係為羧酸根（RC〇〇-)、硫 代羧酸（RCSS')、焦磷酸根（〇3Ρ-0·Ρ〇3·)、或下式之化入物 〇 ° 及其衍生物。 其他較佳橋連配位體係包括：
BL-1
χ/γ\ζ BL-6 X及Z係選自由C、CR、Ο、N、NR、S及P所組成之群. Y係選自由C、N、S及P所組成之群； 92427.doc -23- 1354693 R係為Η或任何有機取代基；且 Ν及Ν係為具有4至8員之烴，可包含雜原子。 該橋連配位體（等）確定該雙核發光材料之兩金屬中心係 保持彼此接近。此情況使得該雙核發光材料可自集合激態 發射，而非自單·金屬（單體）物種發射。該兩金屬中心可於 基態下強或弱偶聯。該等情況可導致極為不同之光物理學 程序。 於基態下弱相互作用之雙核物種（Μ_Μ距離^ 3 Α)易具有 類似激態二聚體之激態。通常，激態二聚體係在個別生光 團於激態下鍵結時所形成，但非於激態下鍵結。激態二聚 體係為具有擴張跨越兩分子或組成物種之激態波動函數的 二聚體。就本發明目的而言，"組成物種"係表示個別金屬 錯合物，即一金屬中心及其所連接之配位體等。就本發明 雙核發光材料而言，該兩包含該激態二聚體之金屬錯合物 係藉由該橋連配位體保持於相對接近。此系統中之激態波 動函數擴張跨越兩金屬錯合物，且通常導致核間之間隔大 幅縮小。當該激態弛張時’該分子之兩部分彼此排斥，而 該系統回復至基態所見到的較大核間間隔。此種弱相互作 用系統並不代表真實之激態二聚冑，因^兩組成物種由 ㈣橋連配㈣的限制而無法完全解離。而光物理學作用 係為類似激態二聚體過程，即該金屬錯合物中之一激發， "亥激態波動函數擴張至兩金屬錯合物、收縮、弛張（發光） 且最後膨脹。 八有強相互作用之金屬錯合物的雙核物種可具有不同之 92427.doc -24- 1354693 光物理學作用。此情況下，激態構型可包括形成M-M鍵結 執道。就d8金屬錯合物而言，此鍵結執道係包括來自各金 屬中心之兩電子的分配、形成填滿之σ鍵結及σ反鍵結（σ*) 軌道，導致此相互作用之淨鍵級係為0。此鍵結圖形先前已 有描述，且係熟習此技術者所熟知。參照，Siu-Wai Lai等 A » "Probing d 8 -d 8 Interactions in Luminescent Mono- and Binuclear Cyclometalated Platinum(II) Complexes of 6-Phenyl-2,2'-bipyridines," Inorg. Chem. (1999) 38, 4046-4055 ; Mann等人，"Characterization of Oligomers of Tetrakis (phenyl isocyanide)rhodium(I) in Acetonitrile Solution," J. Am. Chem. Soc. (1975) 97, 3553-3555，各以引用方式併入。 於基態下，最高填滿軌道通常係為σ *軌道。此情況下之 光物理學係包括將電子自Μ-Μ σ*軌道促進至配位體之π* 軌道或更高層之M-M鍵結軌道。 當接受軌道係為π*軌道時，躍遷係稱為MMLCT(金屬-金 屬-至-配位體-電荷-轉移。該π*軌道係該雙核錯合物之單體 形式的MLCT躍遷中所包括之相同狀態，通常結合有”感光 性配位體”。預測在MMLCT激態下因為σ*軌道減少而有部 分之Μ-Μ距離收縮，但躍遷之性質迥異於在弱相互作用系 統所描述的類激態二聚體躍遷。參照Novozhilova等人， "Theoretical Analysis of the Triple Excited State of the [Pt2(H2P205)4]4- Ion and Comparison with Time-Resolved X-ray and Spectroscopic Results," J. Am. Chem. Soc. (2003) 125, 1079-1087 ; Rice 等人，"Electronic Absorption and 92427.doc -25- 1354693
Emission Spectra of Binuclear Platinum(Il) Complexes. Characterization of the Lowest Singlet and Triplet Excited States of Pt2(H2P205)44-," J. Am. Chem. Soc. (1983) 105, 4571-45 75，各以引用方式併入。 雖然弱相互作用系統之激發係與單體形式相同，但 MMLCT產生σ*至π*躍遷之新吸收，其不存在於單體錯合物 之吸收光譜中。例如，此新譜帶係於雙核Pt錯合物 (F2ppy)2Pt2(SPy)2於500奈米見到之激發光譜（參照圖4)。 雙核材料可具有某些程度之發生於基態的金屬-金屬鍵 結。實際上，唯以決定當摻雜至分子薄膜内時，包含該雙 核發光劑之組成物種是否直接於用以製造OLEDs之類型的 基態下鍵結。某些發光劑之實際情況可能是介於極端情況 之間。例如，包含雙核發光劑之組成物種可具有基態之弱 金屬-金屬鍵結，但於激態下，該鍵結縮短，且該物種變成 強鍵結。此情況下，發光劑並非”真實”激態二聚體，因為 該組成物種係於基態下鍵結。該組成物種可能同時完全參 與於經摻雜薄膜中之7Γ-7Γ堆集及金屬-金屬相互作用兩作 用，導致激態二聚體或MMLCT激態。因此，本發明所使用 之”激態二聚體"在某些情況下可能表示具有強鍵結激態及 弱鍵結基態之組成物種。 該激態二聚物能量低於定域於兩種構成該激子之組成物 種中的任一種上的激子，而其發射一般係相對寬頻。因為 激態二聚體缺乏鍵結基態，其對於達到自電荷載流宿主基 質至發光中心之有效能量轉移提供了獨特之解答。實際 92427.doc -26- 1354693 上，在兩發光材料之情況下，使用激態二聚體防止介於兩 發光劑之間的能量轉移，去除複雜之分子間相互作用，該 分子間相互作用使得使用多重摻雜劑之色彩平衡問題重 重。激態二聚體及激子之性質的評論參照Andrew Gelbert and Jim Baggott, Essentials of Molecular Photochemistry, 1991，CRC Press, Boston, pp. 145-167 〇 e亥感光性配位體係稱為感光性，因相信其藉由對電子提 供7Γ *軌道而導致發光材料之感光性質。不論電子係自以配 位體為主之7Γ*軌道電離，或自以金屬為主之軌道移至以配 位體為主之軌道，該配位體皆視為感光性。該感光性配位 體可為雙配位基或三配位基’其中雙配位基及三配位基用 辭係表示配位體對於單一金屬中心所具有的鍵結數目。就 感光性配位體而言，較佳係對於該金屬中心之至少一鍵結 係為碳-金屬鍵結。本發明較佳具體實例中，該感光性配位 體係包含一或多個芳族環。部分本發明具體實例中，配位 於第一金屬中心之第一感光性配位體及配位於第二金屬中 心之第二感光性配位體係藉橋連配位體來保持接近，而該 第一及第二金屬中心使該第一與第二感光性配位體之間有 π-π相互作用。任何適當之感光性配位體皆可使用。在部分 具體實例中’該第一及第二感光性配位體可具有相同結構。 本發明之一具體實例中，該雙核發光化合物包含兩金屬 中心’其中各金屬中心係鍵結於三配位基感光性配位體， 且鍵結於橋連配位體之鍵結部分中之一，產生式〗之化合物 92427.doc -27- (I) (I)1354693
其中A係為三配位基感光性配位體，匕係為橋連配位體，且 各Μ係為金屬中心。此具體實例中，該等金屬中心各具有 正方平面構型。該感光性三配位基配位體Α係經由三個鍵結 而鍵結於該金屬中心，其中至少一個係為碳_金屬鍵結，且 對該金屬之其餘鍵結係為供給性（雜原子_金屬）鍵結❶較佳 —配位基配位體係為二環芳族化合物。於本發明之一具體 實例中，A係為通式Ila之三配位基感光性配位體 η (Ila) 其中Ar!係為五或六員氮雜環，其中該環具有位於2_位置之 氮原子，可對該金屬中心形成供給性鍵結。該2_位置於此 處係定義為環中與至該中心吡啶環之鍵結相鄰的位置。較 佳具體實例中，Ari係為吡啶或經取代之吡啶，且Ar2係為 笨基或經取代之笨基。 本發明另一具體實例中，Α係為具有通式„b之三配位基 感光性配位體 Ατα m 其中A1*3及A1·4係為個別選擇之五或六員氮雜環，其中各環 係具有位於2-位置之氮原子，可對該金屬中心形成供給性 鍵結。較佳具體㈣中，環ΑΓ3及Ar4中之—係為响啶或經 92427.doc 28· 1354693 取代之3比咬。特佳具體實例中，Ar3及Αγ4兩者皆為吡啶或 經取代之吡啶。 本發明之一具體實例中，該雙核發生化合物係包含兩金 屬中心’其中各金屬中心係鍵結於雙配位基感光性配位體 且鍵結於兩橋連配位體，以產生通式III之化合物：
其中Α'係為雙配位基感光性配位體，l係為橋連配位體，且 Μ係為金屬中心。該雙配位基感光性配位體Α,具有一金屬_ 碳鍵結及一供給性（雜原子-金屬）鍵結，且可選自技術已知 之各式各樣者。特佳具體實例中，Α1係選自2-苯基吡啶及 其衍生物。許多較佳雙配位基感光性配位體係包括下列部 分結構，與金屬配位，以形成一環金屬之有機金屬化合物， 諸如US-2003-0017361所揭示，以引用方式全文併入，表示 為：
Μ可為任何適當之金屬，例如d7、d8或d9金屬，而虛線表 示對感光性配位體之其餘部分的鍵結。 本發明之一具體實例中，該雙核發光性化合物係包含兩 個藉橋連配位體鍵結之金屬中心。此具體實例可不具有任 何感光性配位體。例如，該兩金屬中心可藉四橋連配位體 92427.doc -29· 1354693 鍵結，產生通式ιν之化合物：
其中Μ係為金屬中心且l係為橋連配位體。 因為具有兩金屬中心之化合物（包括雙核化合物）不具有 任何感光性配位體，故光發射可藉由不涉及與感光性配位 體有關之π *軌道的機制發生。詳言之，不具有任何感光性 配位體之雙核化合物的HOMO亦可為σ*執道，主要包含金 屬dn軌道。未激發狀態下之lum〇可為σρ轨道（由高層金屬 ρζ軌道之重疊所形成之(^鍵結軌道），故當電子自σ*軌道移 至σρ軌道時，可發生激態。該種躍遷因以下兩因素而可縮 小介於兩金屬中心之間的距離，第一因為該反鍵結σ*軌道 灰少，第一因為鍵結之σρ軌道變多。發射可藉由電子自A 軌道弛張至σ*軌道而發生。此種發射預測係為磷光。 通常，具有感光性配位體之分子會具有與π*軌道有關之 LUMO，而非σρ執道。先前許多用以得到磷光性發藍光材料 的努力係包括調節介於與感光性配位體有關之π*軌道與σρ 軌道之間的差異。本發明具體實例容許藉由設計雙核或多 核分子來得到藍色材料，而不使用感光性配位體，故ίυΜ〇 不再是π*執道。該LUMO卻為σρ軌道，發射光譜係由介於該 σ*與σρ軌道之間的能量差決定。此能量差可依數種方式調 整。首先’介於金屬中心間之距離可經由橋連配位體之選 擇而加以控制。此距離對於介於該σ*與％轨道之間的能量 92427.doc •30- 1354693 差有極大影響·’因此對發射光譜有極大影響。在其他條件 相同下’較小距離通常導致較低能量及偏紅之發射，而較 大距離則導致較高能量及偏藍之發射。其次，該橋連配位 體可選擇以調整該金屬中心之電子結構。例如，雙核分子 中之σ與σρ轨道係為個別金屬中心之dz執道之間相互作用 的結果。某些橋連配位體可經由配位體場域相互作用而大 幅影響金屬d及p執道的能量。該種執道能量之配位體場 域”調節”可降低或提高個別金屬d及p軌道之能量，視該橋 連配位體之性質及該鍵結排列而定。因此，該配位體場效 可增加介於兩金屬中心之原子軌道之間的能量差，並増加 介該σ*與σρ軌道之間的能量差，以使分子之發射光譜偏移 向藍光。 較佳具體實例中，雙核發光材料具有兩個彼此藉由四個 橋連配位體來鍵結之金屬中心，無感光性配位體。該金屬 中心較佳係具有四個配位部位。Pt係為金屬中心使用之較 佳金屬，因其具有四個共平面配位部位。 雙核發光材料之金屬中心以具有至少3個配位部位為 佳而至少4個配位部位更佳。相信具有含3或4個配位部位 之金屬中心的材料較具有較少配位部位之材料安定。相信 具有至少4個配位部位之金屬中心可能傾向特別安定。實際 上具有4個共平面排列之配位部位的金屬，諸如pt，可導致 特別安定之雙核分子。 本發明具體實例之化合物包含兩個金屬中心。該金屬可 選自原子量大於40之重金屬。該金屬中心之較佳電子構型 92427.doc -31- 1354693 具有八個d電子(例如pt(n)、Pd(II)、Ni(n)、Ir⑴、Rh⑴、
Ag(III)、Au(III)等）’但本發明不限於此等金屬或氧化態。 此等金屬中心係稱為"d8"金屬中心。d8金屬中心因為通常 兩個d8金屬中心之間存有強相互作用而較佳，即使無基態 鍵結亦然。Pt係為特佳d8金屬中心。其他可使用之電子構 型包括具有7d電子之金屬中心（”d7 "金屬中心），及具有％ 電子之金屬中心（”d9”金屬中心）e dl〇金屬中心因為通常具 有長距相互作用且無基態鍵結而較不佳。在部分具體實例 t，雙核錯合物可自兩種具有不同數量之4電子的金屬形 成，即d7金屬可與仳金屬配對。該兩金屬以具有相同數目 之d電子為佳。為易於製造’最佳情況係雙核錯合物之兩金 屬中心係相同金屬。 部分具體實例中，發光材料係為雙核電中性化合物。電 中性化合物因為易於昇華及真空沉積，有助於藉特定方法 製造裝置，而較有利於某些應用。非電中性之化合物可使 用於其他具體實例’但該等化合物之昇華可能困難，故溶 液加工較有利於該等化合物。 應明瞭本文所述之各種具體實例 只1 J白僅供例不，而不限制 發明範圍。例如’本文所述之材料 柯料及結構中許多皆可使用 其他材料及結構來取代，而不偏 ^ ^ ^ ^ 發明之精神。應明瞭本 毛明發揮作用之各種理論不受 ^ 制例如，有關電荷傳遞 之理响不構成限制。 材料定義： 本發明所使用之縮寫係表示下列材料 92427.doc -32· 1354693 CBP ： 4,4'-N，N'-二咔唑-聯苯 m-MTDATA ： 4,4、4”-三（3-甲基苯基苯基胺基）三苯胺 Alq3 : 8 -三-經基p奎琳銘 Bphen : 4，7 -二苯基-1，10 -非繞p林 n-HPeen : η型摻雜之BPhen(摻雜鋰） F4-TCNQ ： 四氟-四氰基-對苯釀二曱苯 p-MTDATA ： P型摻雜之m-MTDATA(摻雜F4-TCNQ) Ir(ppy)3 : 三（2-苯基吡啶）銥 Ir(ppz)3 ·* 三（1-苯基吡唑根基，N，C(2')銥（III) BCP ： 2,9-二曱基-4,7-二苯基-1，10-菲繞啉 TAZ ： 3 -本基-4 - (11 -奈基）-5 -苯基-1，2，4 -二。坐 CuPc ： 銅乃花青 ITO ： 氧化銦錫 NPD ： 萘基-苯基-二胺 TPD ： N，N’-雙（3-甲基笨基）-Ν,Ν'-雙-(苯基）- 聯苯胺 BAlq ： 雙（2-曱基-8-喹啉根基）4-苯基酚鋁（III) mCP · 1，3-Ν,Ν-二咔唑-苯 DCM ： 4-(二亂基伸乙基）-6-(4-二甲胺基苯乙 烯基-2-甲基）-4H-吡喃 DMQA ： N，N’-二曱基喳吖啶 PEDOT:PSS ： 聚（3,4-伸乙基二氧基嘧吩）與聚苯乙烯 基磺酸鹽（PSS)之含水分散液 FPt ： (2-(4-,6-二氟苯基）吡啶根基-队(：2)(2,4- 92427.doc -33- 1354693 戊烷二酮根基-0,0)鉑（II) FPtdpm ： (2-(4-，6-二氟苯基）吡啶根基-N，C2)(2,2, 6,6-四甲基-3,5-庚烷二酮根基-0,0)鉑（II) (F2ppy)2Pt2(SPy)2 :二-始（II)，雙（2-(4,6-二氟苯基）吡啶根基- N，C2)雙[μ-(2-吡啶硫酮根基-N1:S2)]
Pt2Spy4 二鉑（II)，四[μ-(2-吡啶硫酮根基-N1:S2)] 2-硫代p比咬
Spy : 實驗： 現在描述本發明明確之代表性具體實例，包括如何製得 該等具體實例。應明瞭該特定方法、材料、條件、程序參 數、裝置及其類者，並非必然限制本發明範圍。 實施例1 氫硫基p比咬（0.53克，4.8〇毫莫耳）添加於4,6-(1£09}^1;二聚 體（2·00克，2.38毫莫耳）之甲醇溶液中，如Brooks等人， "Synthesis and Characterization of Phosphorescent Cyclometalated Platinum Complexes," Inorganic Chemistry, 2002, 41(12)，3055-3066，以引用方式全文併入。將碳酸鉀 (0.50克）添加至該溶液，加熱至60°C歷經18小時。隨之冷卻 該溶液，於減壓下移除溶劑。粗產物溶於丙酮中，以丙酮 為溶離物而通經矽膠管柱。再次於減壓下移除溶劑，產物 自甲醇再結晶，產生82%產率之（F2ppy)2Pt2(SPy)2的紅色晶 狀化合物。 實施例2 玻璃基材係藉著以清潔劑洗滌，且以去離子水及後續丙 92427.doc -34- 1354693 酮淋洗而製備-該玻璃隨之於氮流下乾燥，置入臭氧爐中 歷經10分鐘。藉著在100毫升量瓶中將5.00毫克 (F2ppy)2Pt2(SPy)2及100毫克CBP溶解於甲苯中，製備100毫 升（F2ppy)2Pt2(SPy)2/CBP溶液（溶液A)。藉著在100毫升量瓶 中將5.00毫克FPt及100毫克CBP溶解於曱苯中，製備100毫 升FPt/CBP溶液（溶液B)。自此等溶液製備兩薄膜。溶液A係 於40,000 rpm下旋塗於玻璃基材上歷經40秒，產生 (F2ppy)2Pt2(SPy)2薄媒。溶液B於40,000 rpm下旋塗於玻璃基 材上歷經40秒，產生FPt薄膜。 在CBP中摻雜有（F2ppy)2Pt2(SPy)2之薄膜以兩光譜激發， 其一波峰在370奈米，而另一者波峰在500奈米。此兩光譜 係選擇約略個別與CBP及（F2ppy)2Pt2(SPy)2之吸收光譜相 符。形成之PL光譜係出示於圖3中。曲線310表示在370奈米 激發之PL光譜。曲線320表示在500奈米激發之PL光譜。在 3 70奈米激發之曲線表示由CBP吸收之能量可轉移至 (F2ppy)2Pt2(SPy)2，且以光形式發射。 圖4出示在CBP中摻雜5%之（F2ppy)2Pt2(SPy)2的薄膜在設 定於605奈米下發射的激發光譜。曲線420係基於與曲線41 0 相同之數據，但數值乘以20，以更仔細地觀看。約略350奈 米之波峰（在曲線410中最明顯可見）係因CBP吸光所致。約 略500奈米之波峰（曲線420中最明顯可見）係因 (F2ppy)2Pt2(SPy)2之吸光所致，且證明在基態下介於兩Pt金 屬中心之間的相互作用。 圖5出示FPt、FPtdpm及（？2卩卩}〇2?1；2(8?}〇2之發射光譜的對 92427.doc -35- 1354693 照。FPt、FPtdpm及在 CBP 中摻雜 5% (F2ppy)2Pt2(SPy)2之磷 光薄膜係藉前述旋塗法製備，且係於3 70奈米下激發。FPt、 FPtdpm及（F2ppy)2Pt2(SPy)2之 PL 光譜個別以曲線 5 10、520 及530出示。 實施例3 有機發光裝置係構建於預先塗覆有~1〇〇奈米厚之氧化銦 錫（ITO)層（薄膜電阻〜20 Ω/口）之玻璃基材上。基材以溶劑去 脂，隨之藉著曝露於UV-臭氧環境下歷經10分鐘而加以清 洗。清洗之後，該基材立即置入在〜lxl〇_6托耳基本壓力下 操作之熱蒸發系統内。製造數種不同之裝置結構，如圖6及 8所示。首先，沉積400 A厚之4-4'-雙[N-(l-莕基）-N-苯基-胺基]聯苯（α-NPD)電洞傳遞層（HTL)。在某些裝置中，沉積 200人厚之111€?層，以作為電子阻隔層（丑61^)。其次，與111€? 或CBP共同沉積9% (F2pp)2Pt2(SPy)2(以重量計），以形成300 A厚之發光層。在某些裝置中，沉積120 A厚之BCP層，以 作為電子阻隔層（EBL)。最後，沉積350 A厚之電子傳遞層 (ETL)，其係由四（8-羥基峻#)錯（IV)(Zrq4)組成。經由障板 (shadow mask)沉積由10 A厚之LiF層構成之裝置陰極，隨之 為1000 A厚之鋁層。該裝置活性面積為2x2毫米2。製得以 下四種結構： 結構 1 : ITO/NPD/(F2pp)2Pt2(SPy)2:CBP/ZrQ4/LiF:Al 結構2 : ITO/NPD/(F2pp)2Pt2(SPy)2:CBP/BCP/ZrQ4/LiF:Al 結構3 : ITO/NPD/(F2pp)2Pt2(SPy)2:mCP/ZrQ4/LiF:Al 結構4 : ITO/NPD/mCP/(F2pp)2Pt2(SPy)2:mCP/ZrQ4/LiF:Al 92427.doc -36- 1354693 圖6出示具有結構1及2之裝置的示意代表圖。結構1具有 —陽極615, 一電洞傳遞層625，一發光層635, 一電子傳遞 層645 ’及一陰極660。結構2係如同結構1，但具有配置於 發光層635與電子傳遞層645之間的附加電洞阻隔層640。各 層之材料及厚度係出示於前文各段中。 圖7出示具有結構1及2之裝置的量子效率相對於電流密 度的曲線圖。曲線710係表示結構1之數據，曲線720係表示 結構2之數據。兩裝置皆顯示約6.0%之最大量子效率。 圖8出示具有結構1及2之裝置的電流密度相對於電壓之 曲線圖。曲線81〇表示結構1之數據，曲線820表示結構2之 數據。 圖9出示具有結構1及2之裝置的電致發光光譜。曲線910 出示結構1之數據，而曲線920出示結構2之數據。 圖10出示具有結構1及2之裝置之亮度對電壓的曲線圖。 曲線1010係出示結構1之數據，曲線1020係出示結構2之曲 線。結構1顯示在6伏特下具有約1〇〇 Cd/m2之較高亮度。 圖11出示具有結構3及4之裝置的示意圖。結構3具有一陽 極1115，一電洞傳遞層1125 ’ 一發光層1135，一電洞傳遞 層114 5 ’及一陰極116 〇。結構4係如同結構3，但具有配置 於電洞傳遞層1125與發光層1135之間的附加電子阻隔層 1130。各層之材料及厚度係如前文各段所示。 圖 12 係出示具有結構 NPD/mCP/EL/Zrq4 及 NPD/EL/Zrq4 (結構4及3)之裝置的量子效率對電流密度的曲線圖。曲線 12 10表示結構3之數據，曲線1220表示結構4之數據。兩裝 92427.doc -37- 1354693 置皆顯示約3.1 %之最大量子效率。 圖 13出示具有結構NPD/mCP/EL/Zrq4 及 NPD/EL/Zrq4 (結 構4及3)之裝置的電流密度對電壓的曲線圖。曲線13 10表示 結構3之數據，曲線1320表示結構4之數據。 圖 14出示具有結構NPD/mCP/EL/Zrq4 及 NPD/EL/Zrq4 (結 構4及3)之裝置的電致發光光譜曲線圖。曲線14 10表示結構 3之數據，曲線1420表示結構4之數據。
圖 15出示具有結構NPD/mCP/EL/Zrq4及NPD/EL/Zrq4 (結 構4及3)之裝置的亮度對電壓的曲線圖。曲線15 10表示結構 3之數據，曲線1520表示結構4之數據。 圖 16 出示 FPt、FPtdpm、及（F2pp)2Pt2(SPy)2之化學結構。 圖17出示（F2pp)2Pt2(SPy)2藉X-射線結晶學測得之結構。
Pt2Spy4(n)及Spy(n)係如以下所述般製備：Umakoshi等 人，"Binuclear Platinum(II) and -(III) Complexes of Pyridine-2-thiol and Its 4-Methyl Analogue, Synthesis, Structure, and Electrochemistry," Inorg. Chem. 1987, 26, 3 55 1-3556，以引用方式全文併入。 圖18出示在2-甲基四氫囷喃（2-曱基-THF)中濃度低於1 11河之？128卩丫4的？]^發射光譜。曲線1810出示2-曱基-1[1^之吸 收波峰，而曲線1220出示Pt2Spy4之吸收波峰。曲線1820之 波峰約於400奈米，尾部於470奈米大幅減弱，證明使用不 含感光性配位體之雙核材料可得到深藍色發射。 圖19出示Pt2Spy4及Spy於溶液下之吸收光譜。曲線1910 出示Spy之吸收光譜。曲線1920出示Pt2Spy4之吸收光譜。 92427.doc -38- 1354693 雖係針對特定實施例及較佳具體實例描述了本發明，但 應明瞭本發明不受限於此等實施例及具體實例。本發明所 申請包括來自本文所述之特定實施例及較佳具體實例為熟 習此技術者所熟知的變化形式。 【圖式簡單說明】 圖1出示具有分隔之電子傳遞、電洞傳遞及發光層、及其 他層之有機發光裝置。 ' 圖2出示不具有分隔電子傳遞層之倒置有機發光裝置。 圖3出示在CBP中摻雜5% (F2ppy)2pt2(spy)2的薄膜之光致 發光光1#。 圖4出示在CBP中摻雜5% (F2Ppy)2Pt2(spy)2的薄膜在設定 於605奈米下之發光的激發光譜。 圖5出不FPt、FPtdpm及（FzppyLPtKSPy)2之發光光譜的比 較。在 CBP 中各摻雜 5%之州、Fptdpm及（F2ppy)2pt2(spy)2 之光致發光薄膜係藉旋塗法製備，且係於37〇奈米下激發。 圖6出示裝置之示意圖IT〇/NpD (4〇〇 A)雙核錯合物， 9% : (300 A)/BPC (120 A，選擇性）/Zrq4 (350 A)/Li:A1 (1〇〇〇 A) 〇 圖7出示具有圖6所說明之結構的裝置之量子效率對電流 密度的曲線圖。 圖8出不具有圖6所說明之結構的裝置之電流密度相對於 電壓之曲線圖。 圖9出不具有圖6所說明之結構的裝置之電致發光光譜的 曲線圖。 92427.doc -39- 1354693 圖10出示具有圖6所說明之結構的裝置之亮度相對於電 壓之曲線圖。 圖11出示裝置之示意圖ITO/NPD (400 A)/mCP (200 A，選 擇性）/雙核錯合物，9% : mCP (300 A)/Zrq4 (350 A)/Li:Al (1000 A) 〇 圖12出示具有圖11所說明之結構的裝置之量子效率相對 於電流密度之曲線圖。 圖13出示具有圖11所說明之結構的裝置之電流密度相對 於電壓之曲線圖。 圖14出示具有圖11所說明之結構的裝置之電致發光光譜 的曲線圖。 圖15出示具有圖π所說明之結構的裝置之亮度相對於電 壓之曲線圖。 圖 16 出示 FPt、FPtdpm 及（FzppyhPtdSPy)2之化學結構。 圖17出示（FepyhPtXSPy)2藉X射線結晶學測定之結構。 圖18出示PtzSpy4於溶液中之PL發光光譜。 圖19出示Ptjpy4及Spy於溶液中之吸收光譜。 【圖式代表符號說明】 100 有機發光裝置 110 基材 115 陽極 120 電洞注射層 125 電洞傳遞層 130 電子阻隔層 92427.doc . 40 - 1354693 135 發光層 140 電洞阻隔層 145 電子傳遞層 150 電子注射層 155 保護層 160 陰極 162 第一導電層 164 第二導電層 200 倒置之OLED 210 基材 215 陰極 220 發光層 225 電洞傳遞層 230 陽極 615 陽極 625 電洞傳遞層 635 發光層 640 附加電洞阻隔層 645 電子傳遞層 660 陰極 1115 陽極 1125 電洞傳遞層 1130 附加電子阻隔層 1135 發光層 92427.doc -41 11451354693 1160 電洞傳遞層 陰極 92427.doc •42
Claims (1)
1354693 第093108931號專利申請案 厂中0請專利範圍替換本(1〇〇年7幻
、K申請專利範圍：
一種有機發光裝置，包含 一陽極； 一陰極；及 之間且與該陽極與 含有下列部分之雙 一發光層，配置於該陽極與該陰極 陰極電連，該發光層係進一步包含— 核發光材料： 第一金屬中心，其選自⑽金屬； 第二金屬中心，其選自“金屬；及 橋連配位體，配位於該第一金屬中心及且配位該第二 金屬中心； 其中介於該第一金屬中心與該第二金屬中心之間的距 離係小於4A，及其中該兩個金屬中心、係藉由橋連配位體 而具有共面構型。 2. 如申印專利範圍第1項之裝置，其中該第一金屬中心及該 第二金屬中心兩者皆選自由d8金屬所組成之群。 3. 如申請專利範圍第2項之裝置，其中介於該第一金屬中心 與第二金屬中心之間的距離係使得第一金屬中心之⑽軌 道與第二金屬中心之48軌道之間重疊。 4. 如申請專利範圍第2項之裝置，其中該第一金屬中心及該 第二金屬中心兩者皆為相同金屬。 5. 如申請專利範圍第4項之裝置，其中該第一金屬中心及該 第二金屬中心兩者皆為pt。 6. 如申請專利範圍第1項之裝置，其中該發光材料係包含下 92427-1000708.doc 歹1J邹分之雙核材料： 四個橋連配位體’其中各橋連配位體係各配位於該第 7 金屬中心且配位於該第二金屬中心。 如申4專利範圍第1項之裝置，其中該發光材料係為包含 下列部分之雙核材料： 一個橋連配位體，其中各橋連配位體係各配位於該第 —金屬中心且配位於該第二金屬中心； 第一雙配位基感光性配位體，鍵結於該第一金屬中 心，及 第二雙配位基感光性配位體，鍵結於該第二金屬中心。 8. 如申請專利範圍第7項之裝置，其中該第―感光性配㈣ 及該第二感光性配位體係藉橋連配位體保持接近，而該 第一及第二金屬中心容許該第一及第二感光性配位體間 之π-π交互作用。 9. 如申請專利範圍第8項之裝置，其中該第一及第二感光性 配位體係具有相同結構。 10. 如申請專利範圍第1項之裝置，其中該發光材料係為包含 下列部分之雙核材料： 一個橋連配位體’其中各橋連配位體係各配位於該第 一金屬中心且配位於該第二金屬中心； 第一雙配位基感光性配位體，鍵結於該第一金屬中 心，及 第二雙配位基感光性配位體，鍵結於該第二金屬中心。 11. 如申請專利範園第10項之裝置，其中該第一感光性配位 92427-1000708.doc -2- 1354693 體及4第—感光性位體係藉橋連配位體保持接近，而 第及第一金屬中心容許該第一及第二感光性配位體 間之π·π交互作用。 12. 如申請專利範圍第叫之裝置，其中該第—及第二感光 性配位體係具有相同結構。 13. 如申。月專利圍第i項之裝f，其中該發光層係進一步包 材料且該發光材料係以摻雜劑形式存在於該宿 主材料中。 14. 如申請專利範圍第㈣之裝置，其中該裝置係包含 一陽極； 一電洞傳遞層； 一電子傳遞層； 一陰極； 及一發光層，其中該發光層係配置於該電洞傳遞層與 該電子傳遞層之間。 如申》月專利範圍第巧之裝置，其中自該裝置發射之光係 來自激二聚體發射。 16·”請專利範圍^項之裝置’其中該發光分子係為碟光 發光材料。 17.如申清專利範圍第7項之裝置，其中該第一及第二感光性 配位體係具有以下部分結構： 92427-1000708.doc
Μ
19. 其中Μ係為金屬中心β
18.如申請專利範圍第i項之裝 如申請專利範圍第1項 置，其中各橋連配位體係選自
之裝置，其中該橋連配位體係選自 下列組成之群：
BL*4 BL-5 BL-6 其中： X及z係選自由c、CR、〇、N、NR、s及p所組成之群； γ係選自由C、N、s及P所組成之群； R係為Η烧基或芳基取代基；且 Ν及Ν，係為具有4至8員碳原子或氮原子之烴鏈。 2〇·如申請專利範圍第〗9項之裝置，其中Ν&Ν|係包含雜原 92427-1000708.doc 1354693 21.如申請專利範圍第1項之裝置，其中該發光分子係具有以 下結構：
22·如申請專利範圍第丨項之裝置，其中介於該第一金屬中心 與該第二金屬_心之間的距離係2·5埃至2·8埃。 23·如申請專利範圍第1項之裝置，其中該發光材料不包含感 光性配位體。 %如申請專利範圍第w之裝置，其中該第一及第二金屬 中心係各具有正方平面構型。 仏如申請專利範圍第1之裝置，其中該雙核發光材料是電 中性的。 26.如中請專利範圍第1項之裝置，其中該橋連配位體具有下 式，其中Β係為五.或六.員環，其中χΑγ係可對該第—金 ^中心或該第二金屬中心形成供給性鍵結之原子或部 其中該兩個金屬中心係具 27·如申請專利範圍第1項之裝置 92427-1000708.doc 1354693 有正方平面共面構型，且其中該橋連配位體為
W/ 0 或 92427-1000708.doc
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| Publication number | Priority date | Publication date | Assignee | Title |
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| TWI694628B (zh) * | 2018-02-06 | 2020-05-21 | 星宸光電股份有限公司 | 電子元件 |
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|---|---|
| WO2004093210A1 (en) | 2004-10-28 |
| JP5384789B2 (ja) | 2014-01-08 |
| JP2011109140A (ja) | 2011-06-02 |
| CN1795569A (zh) | 2006-06-28 |
| US20060269785A1 (en) | 2006-11-30 |
| JP5730613B2 (ja) | 2015-06-10 |
| EP1609197B1 (en) | 2007-02-28 |
| DE602004005014T2 (de) | 2007-07-12 |
| DE602004005014D1 (de) | 2007-04-12 |
| US7090928B2 (en) | 2006-08-15 |
| TW200427813A (en) | 2004-12-16 |
| CN1795569B (zh) | 2010-09-22 |
| US7824778B2 (en) | 2010-11-02 |
| KR101056477B1 (ko) | 2011-08-12 |
| ATE355618T1 (de) | 2006-03-15 |
| EP1609197A1 (en) | 2005-12-28 |
| KR20050109618A (ko) | 2005-11-21 |
| US20040197600A1 (en) | 2004-10-07 |
| JP2006522487A (ja) | 2006-09-28 |
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