TW201217356A - Novel compounds for organic electronic material and organic electroluminescent device using the same - Google Patents
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Abstract
Description
201217356 六、發明說明： 【發明所屬之技術領域】 本發明係關於用於有機電子材料之新穎化合物及使用 該等化合物之有機電激發光裝置。 【先前枝術】 於藏員示器裝置中，電激發光（electroluminescent, EL) &置的優越性在於作為自發光顯示器裝置，其視角廣、對 比度尚且反應速率快。1987年’伊斯門-柯達（Eastman Kodak)首先研發出使用低分子量之芳香二胺及|呂錯合物作 為形成電激發光層之物料的有機EL裝置[yippA L^tt. 51, 913, 1987] ° 於有機EL裝置中，將電荷施加至形成於電子注入電極 (陰極）與電洞注入電極（陽極）之間的有機層時，電子與電 洞係配對並產生激子（e x c i t 〇 n )。藉由使用在激子失活之狀 態的電激發光（磷光或螢光）而發光。有機EL裝置於約⑺ 伏特（v)之電壓及約100至10,000燭光（cd)/平方米之 高亮度發射偏極光。有機EL裝置具有下列特性：僅藉選擇 螢光材料便能發射自藍色至紅色光譜範圍之光。有機乩裳 置的優越性在於其可形成於可撓性透明基板（例如塑膠') 上，與電漿顯示面板或無機EL顯示器相比，其可以較低。 壓（10 V或更低）操作，消耗較少功率，並提供優異顏色^ 於有機EL裝置中，決定其包括發光效率及操作壽务 效能的最重要因素為電激發光材料。對電激發光^^ 些要求包括於固態之高電激發光量子產率、 ^ 阿包及電洞201217356 VI. Description of the Invention: TECHNICAL FIELD OF THE INVENTION The present invention relates to novel compounds for organic electronic materials and organic electroluminescent devices using the same. [Previous branching] In the Tibetan display device, the electroluminescent (EL) & setting is advantageous as a self-luminous display device, which has a wide viewing angle, a high contrast ratio, and a fast reaction rate. In 1987, Eastman Kodak first developed an organic EL device using a low molecular weight aromatic diamine and a lysine as a material for forming an electroluminescent layer [yippA L^tt. 51, 913, 1987] ° In an organic EL device, when an electric charge is applied to an organic layer formed between an electron injecting electrode (cathode) and a hole injecting electrode (anode), electrons are paired with a hole system and excitons are generated (excit 〇n ). Light is emitted by using electrical excitation light (phosphorescence or fluorescence) in the state of exciton inactivation. The organic EL device emits polarized light at a voltage of about (7) volts (v) and a high luminance of about 100 to 10,000 candelas (cd) per square meter. The organic EL device has the following characteristics: light can be emitted from the blue to red spectral range only by selecting a fluorescent material. The advantage of the organic enamel is that it can be formed on a flexible transparent substrate (e.g., plastic '), which can be lower than a plasma display panel or an inorganic EL display. Pressure (10 V or less) operation, consuming less power, and providing excellent color ^ In organic EL devices, the most important factor in determining its luminous efficiency and operational life performance is electroluminescent materials. Some requirements for electro-excitation light include high-energy excitation quantum yield in solid state, ^ A Bao and hole
3 S 95334 201217356 移動性、於真空沈積過程中之分解抗性、形成均勻薄膜的 能力及安定性。 有機電激發光材料大致可分為高分子量材料及低分子 量材料。就分子結構來看，低分子量材料包括金屬錯合物 及不含金屬之純有機電激發光材料。此等電激發光材料包 括螯合錯合物例如參（8-經基喧琳基）銘錯合物（tris(8_ quinolinolato)aluminum complex)、香豆素衍生物、四苯 基丁二烯衍生物、雙（苯乙烯基伸芳基）（bis (styrylarylene)衍生物及噚二唑衍生物。報告指出，由彼 等材料可獲得從藍色到紅色可見光區域的光發射。 為了實現全彩有機發光二極體（〇LED)顯示器，使用了 三種（紅色、綠色及藍色）電激發光材料。為了提升有機電 ，發光（EL)裝置之整體特性，重點為研發具有高效率及長 壽命之紅色、綠色及藍色電激發光材料。於功能而言，EL 材料分為主體材料及摻雜劑材料。—般咸知具有最優異 f質之裝置。構可利用藉由摻雜摻雜劑到主體材料而製得 目前’發_高效率及長壽命之有機 特別是考慮到從中型到大型尺寸的 1右EL性質時’亟需研發相較於傳·材料 具有更好的EL性質之材料。 一。===體材料之研發係待解決之最重要課題之 性質為1产及t(作為固態之溶劑及能量輸送者），所欲 卜ί:: 分子量以能在真空中氣相沉積。此 卜’應…夠㈣麵轉移溫度及熱分解溫度以確保轨安定 95334 4 201217356 性。再者’主體材料應具有高電化學安定性以提供長壽命。 谷易形成對其他相鄰材料具高黏著性而無層内遷移之非晶 質（amorphous)薄膜。 當藉由摻雜技術製造有機EL裝置時，於激發狀態中自 主體分子向摻雜劑之能量轉移比例無法達到100%，且主體 材料與摻雜劑都發光。尤其，於紅光發射裝置之實例中， 由於主體材料發光之波長範圍具有比摻雜劑更大的可見 性’因此主體材料黯淡的光發射造成色純度惡化。若實際 應用該技術’則需要增加發光壽命及改善耐久性。 目前’ CBP是最廣為所知之用於磷光材料的主體材料。 已提出使用包含BCP、BAlq等之電洞阻擋層的高效〇LED。 曰本先鋒公司（Pi〇neer)等已提出使用BAlq衍生物作為主 體之高效能0LED。3 S 95334 201217356 Mobility, decomposition resistance during vacuum deposition, ability to form a uniform film and stability. Organic electroluminescent materials can be broadly classified into high molecular weight materials and low molecular weight materials. In terms of molecular structure, low molecular weight materials include metal complexes and metal-free pure organic electroluminescent materials. Such electroluminescent materials include chelating complexes such as tris(8-quinolinolato)aluminum complex, coumarin derivatives, tetraphenylbutadiene derivatives. , bis (styrylarylene) derivatives and oxadiazole derivatives. Reports indicate that light emission from blue to red visible regions can be obtained from these materials. A diode (〇LED) display uses three (red, green, and blue) electroluminescent materials. To enhance organic power, the overall characteristics of the EL device are focused on developing red with high efficiency and long life. , green and blue electroluminescent materials. In terms of function, EL materials are divided into host materials and dopant materials. - The most excellent device with the best quality. The structure can be doped by doping dopants. The main material is made of the current 'hair-high efficiency and long-life organic, especially considering the right-right EL property from medium to large size'. It is urgent to develop materials with better EL properties than the materials. One. === body The nature of the most important subject to be solved is the production and t (as a solid solvent and energy transporter). The molecular weight is such that it can be vapor deposited in a vacuum. (4) Surface transfer temperature and thermal decomposition temperature to ensure rail stability 95334 4 201217356. In addition, 'the host material should have high electrochemical stability to provide long life. Valley easy to form high adhesion to other adjacent materials without layer Amorphous film that migrates. When an organic EL device is fabricated by a doping technique, the energy transfer ratio from the host molecule to the dopant in the excited state cannot reach 100%, and both the host material and the dopant are In particular, in the case of a red light emitting device, since the wavelength range in which the host material emits light has greater visibility than the dopant, the light emission of the fading light of the host material causes the color purity to deteriorate. If the technique is actually applied, It is necessary to increase the luminescence lifetime and improve the durability. At present, 'CBP is the most widely known host material for phosphorescent materials. It has been proposed to use a hole barrier layer containing BCP, BAlq, etc. Efficient 〇LED. Pioneer said this (Pi〇neer) or the like has been proposed to use high-performance BAlq derivative as the main body of 0LED.
儘管這些材料提供良好之電激發光特性，但因為玻璃 轉移溫度低、熱安定性差，其缺點為於真空之高溫沈積製 程期間可能出現降解。由於〇Led之功率效率係藉由（η/ 電壓）x電流效率而獲得，因此功率效率與電壓成反比。需 要高功率效率以降低0LED的功率消耗。實際上，使用填光 材料之0LED提供較彼等使用螢光材料者高得多的電流效 率（燭光/安培（cd/A))。然而，當使用現有材料如BAlq、 s 5 95334 201217356 CBP等作為磷光材料之主體時，因為其高驅動電壓，比起 使用螢光材料之0LED，其並未具顯著優越的功率效率（流 明（lm)/瓦（W))。再者，戎0LED裝置不具有令人滿意的操 作壽命。因此仍需要研發更安定、更高效能之主體材料。 【發明内容】 (技術問題）Although these materials provide good electrical excitation characteristics, they have the disadvantage of being degraded during vacuum high temperature deposition processes because of the low glass transition temperature and poor thermal stability. Since the power efficiency of 〇Led is obtained by (η/voltage) x current efficiency, the power efficiency is inversely proportional to the voltage. High power efficiency is required to reduce the power consumption of the OLED. In fact, OLEDs using a fill material provide much higher current efficiency (candle/ampere (cd/A)) than those using phosphors. However, when an existing material such as BAlq, s 5 95334 201217356 CBP or the like is used as the main body of the phosphorescent material, it has no remarkable superior power efficiency (lumens (lm) because of its high driving voltage compared to the OLED using the fluorescent material. ) / watt (W)). Furthermore, the 戎0 LED device does not have a satisfactory operational life. Therefore, there is still a need to develop more stable and more efficient host materials. SUMMARY OF INVENTION (Technical Problem)
座標之優異骨架的用於有機電子材料之化合物。本發明之 另目的係提供具有長才呆作壽命之高效有機電激發光裝 置’其係制用於有機電子材料的化合物作為電激發光材 料。 (技術解決方案） 本發明提供下述化學式1所示之用於有機電子材料的 化合物，及使用該化合物之有機電激發光裝置。因具良好 之發光效率及優異之壽命性f，根據本發明之用於有機電 子材料的化合物可用以製造具有極高操作壽命及因提升功 率效率而消耗較少功率的0LED裝置。 化學式1 \A compound for organic electronic materials with an excellent skeleton of coordinates. Another object of the present invention is to provide a high-efficiency organic electroluminescent device having a long-lasting lifetime, which is a compound for an organic electronic material as an electroluminescent material. (Technical Solution) The present invention provides a compound for an organic electronic material represented by the following Chemical Formula 1, and an organic electroluminescent device using the same. The compound for an organic electronic material according to the present invention can be used to manufacture an OLED device having an extremely high operational life and consuming less power due to improved power efficiency due to good luminous efficiency and excellent lifetime f. Chemical formula 1 \
6 95334 、 2012173566 95334, 201217356
Li及L2係獨立地表示單鍵、（C3-C30)伸環烷基、 (C6-C30)伸芳基或（C3-C30)伸雜芳基； Χι及X2係獨立地表示CRe或N，但排除其中Χι及X2均 為CRe的情況； 1至R6係獨立地表示氫、氘、（C1-C30)烷基、鹵（C1-C30) 烷基、齒素、氰基、（C3-C30)環烷基、5-至7-員雜環烷基、 (C2-C30)烯基、（C2-C30)炔基、（C6-C30)芳基、（C1-C30) 烷氧基、（C6-C30)芳氧基、（C3-C30)雜芳基、（C6-C30)芳 (H-C30)烷基、（C6-C30)芳基硫基、單或二（C1-C30)烷基 胺基、單或一（C6-C30)芳基胺基、三（C1-C30)烧基石夕烧基、 二（C1-C30)烧基（C6-C30)芳基矽烧基、三（C6-C30)芳基矽 烧基、蛾基或經基；以及 及之伸環烷基、伸芳基及伸雜芳基，以及匕至匕 之烧基、環烧基、雜環烧基、烯基、炔基、芳基及雜芳某， 可獨立地進一步經一或多個選自下列所組成之群組^取 代：氘、（C1-C30)烷基、鹵（C1-C30)烷基、_素、氰美 (C3-C30)環烷基、5-至7-員雜環烷基、（C2_C3〇)烯二、 (C2-C30)炔基、（C6-C30)芳基、（C卜C30)烷氧基、（C6 ^ 芳氧基、（C3-C30)雜芳基、（C6_C30)芳（C1—C3〇)俨 (C6-C30)芳基硫基、單或二（cl_C3〇)烷基胺基、2 = (C6-C30)芳基胺基、三（C1_C3〇)烷基矽烷基、或二 烷基（C6-C30)芳基矽烷基、三（C6_C3〇)芳基矽燒 C3〇) 及羥基； 疋土、硝基 該伸雜芳基、雜環烷基及雜芳基包含選自 曰 β、N、〇、s、Li and L2 independently represent a single bond, (C3-C30)cycloalkylene, (C6-C30) extended aryl or (C3-C30) heteroaryl; Χι and X2 independently represent CRe or N, However, the case where Χι and X2 are both CRe is excluded; 1 to R6 independently represent hydrogen, hydrazine, (C1-C30) alkyl, halo (C1-C30) alkyl, dentate, cyano, (C3-C30) a cycloalkyl group, a 5- to 7-membered heterocycloalkyl group, a (C2-C30) alkenyl group, a (C2-C30) alkynyl group, a (C6-C30) aryl group, a (C1-C30) alkoxy group, C6-C30) aryloxy, (C3-C30)heteroaryl, (C6-C30)aryl(H-C30)alkyl, (C6-C30)arylthio,mono or di(C1-C30)alkane Amino group, mono or mono(C6-C30) arylamine group, tri(C1-C30) alkyl ruthenium group, di(C1-C30) alkyl group (C6-C30) aryl fluorenyl group, three ( a C6-C30) aryl fluorenyl group, a moth group or a thiol group; and a cycloalkyl group, an aryl group and a heteroaryl group, and a pyridyl group, a cycloalkyl group, a heterocyclic group, Alkenyl, alkynyl, aryl and heteroaryl, which may be independently substituted further by one or more groups selected from the group consisting of hydrazine, (C1-C30) alkyl, halo (C1-C30) alkane Base, _ prime, cyanide (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2_C3 fluorene) alkene, (C2-C30) alkynyl, (C6-C30) aryl, (C-C30) alkoxy , (C6^ aryloxy, (C3-C30)heteroaryl, (C6_C30) aryl (C1-C3〇) fluorene (C6-C30) arylthio, mono or bis(cl_C3〇)alkylamino 2 = (C6-C30) arylamino group, tri(C1_C3〇)alkyl fluorenyl group, or dialkyl (C6-C30) aryl decyl group, tris(C6_C3 fluorene) aryl argon C3 〇) Hydroxyl; bauxite, nitro, heteroheteroaryl, heterocycloalkyl and heteroaryl are selected from the group consisting of 曰β, N, 〇, s,
7 S 95334 201217356 P(=〇)、Si及p所組成之群組的一或多個雜原子； 但排除其中*-LfR1為氫原子的情況。 【實施方式】 在本發明中，「烷基」、「烷氧基」及含有「烷基」部分 (moiety)之其他取代基係包含直鍵及分支鍵兩者。在本發 明中’「環院基」係包含多環烴環例如具有或不具有取代基 之金剛燒基、或具有或不具有取代基之（C7_C3〇)雙環烷 基；以及單環烴環。在本發明t，「芳基」意指自芳香烴去 除一個氫原子所得之有機基團，可包含4-至7-員（尤其是 5-或6-員）之單環或稠合環，包含複數個藉由單鍵鏈結之 芳基。其具體實例包含但不限於：苯基、萘基、聯苯基、 蒽基、茚基、第基、菲基、聯伸三笨基（tr i pheny 1 eny 1)、 玄匕基、茈基、蒯基（chrysenyl)、稠四苯基（naphthacenyl)、 丙一埽合第基（fluoranthenyl)等。萘基係包含1-萘基及 2-萘基’蒽基係包括1-蒽基、2-蒽基及9-蒽基，苐基係包 括卜第基、2-第基、3-第基、4-苐基及9-»基。在本發明 中，「雜芳基」意指含有作為芳香環骨架原子之選自B、N、 0、S、P(=〇)、^及p所組成之群組的1至4個雜原子， 以及作為剩餘芳香環骨架原子之碳的芳基。雜芳基可例示 如5-或6-員單環雜芳基，及與一或多個笨環縮合之多環雜 芳基’其可為部分飽和。再者’雜芳基亦包含藉由單鍵連 結之1個以上的雜芳基。雜芳基包含二價芳基，其中，該 環之雜原子可經氧化或四級化（quaternized)以形成諸如 N-氧化物或四級鹽。其具體實例包含但不限於：單環雜芳 8 95334、 201217356 基，諸如呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻 °坐基、"塞二唾基、異。塞。坐基、異嗜峻基、卩萼唾基、曙二唾 基、三畊基、四啡基、三唑基、四唑基、呋咕基（furazanyl)、 吡啶基、吡α井基、嘧啶基、嗒啡基等；多環雜芳基，諸如 笨并呋喃基、苯并嗟吩基、異苯并呋喃基、苯并咪唑基、 苯并噻唑基、苯并異噻唑基、笨并異噚唑基、苯并噚唑基、 異吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、異 喹啉基、噌啉基（cinnolinyl)、喹唑啉基、喹噚啉基、咔 坐基啡疋基、本并二嗜呃基（benZ〇di〇X〇lyl)等；其N 一 氧化物（例如吡啶基N-氧化物、喹啉基N-氧化物等）Γ盆四 級鹽等。 八 在本發明中’「（a_C3〇)烧基」包含（n_C2〇)烧基，更 ，體地為（C卜C10)燒基；以及「（C6_⑽芳基」包含（C6_⑽ 芳基更具體地為（C6-C12)芳基。並且，r (C3_C3〇)雜芳基」 $含(C3-C')雜芳基’更具體地為(C3—⑽雜芳基；以及 基」包含⑽環絲，更具體地為 )桃基。並且，「（G2调縣或絲」包含你C20) 婦基或炔基，更具體地為（C2-C10)烯基或炔基。 此外根據本發g狀用於有機電子材料的化 下列之化學式2或3所示。 化學式27 S 95334 201217356 P(=〇), one or more heteroatoms of the group consisting of Si and p; but excluding the case where *-LfR1 is a hydrogen atom. [Embodiment] In the present invention, "alkyl", "alkoxy" and other substituents containing an "alkyl" moiety include both a straight bond and a branched bond. In the present invention, the "ring-based group" includes a polycyclic hydrocarbon ring such as an adamantyl group having or not having a substituent, or a (C7_C3〇)bicycloalkyl group having or not having a substituent; and a monocyclic hydrocarbon ring. In the present invention t, "aryl" means an organic group obtained by removing one hydrogen atom from an aromatic hydrocarbon, and may contain a 4- to 7-membered (especially 5- or 6-membered) monocyclic or fused ring. Contains a plurality of aryl groups linked by a single bond. Specific examples thereof include, but are not limited to, phenyl, naphthyl, biphenyl, anthracenyl, fluorenyl, decyl, phenanthryl, teri pheny 1 eny 1 , 玄 匕, 茈, Chrysenyl, naphthacenyl, fluoranthenyl, and the like. The naphthyl group includes a 1-naphthyl group and a 2-naphthyl 'anthracene group including a 1-fluorenyl group, a 2-fluorenyl group and a 9-fluorenyl group, and the anthracenyl group includes a bhizo group, a 2-position group, and a 3-position group. , 4-mercapto and 9-» base. In the present invention, "heteroaryl" means 1 to 4 hetero atoms containing a group consisting of B, N, 0, S, P (= 〇), ^ and p as an aromatic ring skeleton atom. And an aryl group as a carbon of the remaining aromatic ring skeleton atom. The heteroaryl group can be exemplified by a 5- or 6-membered monocyclic heteroaryl group, and a polycyclic heteroaryl group condensed with one or more stupid rings, which can be partially saturated. Further, the 'heteroaryl group also includes one or more heteroaryl groups bonded by a single bond. The heteroaryl group contains a divalent aryl group in which the hetero atom of the ring may be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt. Specific examples thereof include, but are not limited to, monocyclic heteroaryl 8 95334, 201217356, such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiopyranyl, "thalylene, iso. Plug. Sitrate, heterophilic, sulfhydryl, hydrazinyl, tri-negative, tetramorphyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyr alpha well, pyrimidine a cyclyl group, a phenyl group, or the like; a polycyclic heteroaryl group such as a benzofuranyl group, a benzononenyl group, an isobenzofuranyl group, a benzimidazolyl group, a benzothiazolyl group, a benzisothiazolyl group, a stupid Carbazolyl, benzoxazolyl, isodecyl, fluorenyl, oxazolyl, benzothiadiazolyl, quinolyl, isoquinolinyl, cinnolinyl, quinazolinyl , quinoxalinyl, quinone quinone thiol, benzyl hydrazide (benZ〇di〇X〇lyl), etc.; N-oxide (eg pyridyl N-oxide, quinolinyl N-oxidation) Things, etc.) VIII In the present invention, '(a_C3〇) alkyl) includes (n_C2〇) alkyl, more physically (Cb C10) alkyl; and "(C6_(10)aryl" contains (C6_(10) aryl more specifically Is (C6-C12) aryl. And, r(C3_C3〇)heteroaryl"$(C3-C')heteroaryl" is more specifically (C3—(10)heteroaryl; and the group contains (10) Silk, more specifically) peach base. Also, "(G2 Tunxian or silk) contains your C20) gynecyl or alkynyl group, more specifically (C2-C10) alkenyl or alkynyl. For the formation of organic electronic materials, the following chemical formula 2 or 3 is shown.
S 95334 9 201217356S 95334 9 201217356
其中， 及係獨立地表示單鍵、（C3_C3〇)伸環烷基、 (C6-C30)伸芳基或（C3—⑽）伸雜芳基；Ri為似_⑽）芳基 或（C3-C30)雜芳基；匕至Re係如化學式丨中所定義； L2之伸裱烷基、伸芳基及伸雜芳基，以及Ri之芳基及雜芳 基，可獨立地進一步經一或多個選自下列所組成之群組者 取代··氘、（C1-C30)烷基、鹵（C1_C3〇)烷基、函素、氰基、 (C3-C30)環烷基、5-至7-員雜環烷基、（C2-C3〇)烯基、 (C2-C30)炔基、（C6-C30)芳基、（C1-C30)烷氧基、（C6-C30) 芳氧基、（C3-C30)雜芳基、（C6-C30)芳（C卜C30)烷基、 (C6-C30)芳基硫基、單或二（ci-C30)燒基胺基、單或二 (C6-C30)芳基胺基、三（C1-C30)烧基石夕燒基、二（C1-C30) 烧基（C6-C30)芳基矽烷基、三（C6-C30)芳基矽烧基、硝基 及經基。Wherein, the system independently represents a single bond, (C3_C3〇)cycloalkylene, (C6-C30) extended aryl or (C3—(10)) aryl; Ri is _(10)) aryl or (C3- C30) a heteroaryl group; a hydrazine to Re is as defined in the formula: an alkylene group, an aryl group and a heteroaryl group of L2, and an aryl group and a heteroaryl group of Ri, which may independently be further subjected to one or a plurality of groups selected from the group consisting of: 氘, (C1-C30) alkyl, halo (C1_C3〇) alkyl, cyclin, cyano, (C3-C30) cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2-C3 fluorenyl)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C30) aryloxy , (C3-C30)heteroaryl, (C6-C30)aryl(C-C30)alkyl, (C6-C30)arylthio,mono or di(ci-C30)alkylamino, single or two (C6-C30) arylamino group, tri(C1-C30) alkyl ruthenium group, di(C1-C30) alkyl (C6-C30) aryl decyl group, tris(C6-C30) aryl oxime Base, nitro and meridine.
Ri之雜芳基可選自下列結構： 95334 10 201217356The heteroaryl group of Ri may be selected from the following structures: 95334 10 201217356
Rl2 r12 Y 為 NR13、〇 或 S ; Z 為 NR13、CRi4R15、〇 或 s ; Rn 至 r15 係獨立地為氫、氘、（C1-C30)烷基、_(C1-C30)烷基、鹵 素、氰基、（C3-C30)環烷基、5-至7-員雜環烷基'(C2-C30) 稀基、（C2-C30)炔基、（C6-C30)芳基、（C1-C30)烷氧基、 (C6-C30)芳氧基、（C3-C30)雜芳基、（C6_C3〇)芳（cl_C3〇) 烷基、（C6-C30)芳基硫基、單或二（C1-C30)烷基胺基、單 或二（C6-C30)芳基胺基、三（C1-C30)烷基矽烷基、二 (C1-C30)烷基（C6-C30)芳基矽烷基、三（C6 C3〇)芳基矽烷 基、磺基紐基；A為單環或多環之芳香環或單環或多環 具體而言，匕係選自下列結構：Rl2 r12 Y is NR13, 〇 or S; Z is NR13, CRi4R15, 〇 or s; Rn to r15 are independently hydrogen, hydrazine, (C1-C30) alkyl, _(C1-C30) alkyl, halogen, Cyano, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl'(C2-C30), (C2-C30)alkynyl, (C6-C30)aryl, (C1- C30) alkoxy, (C6-C30) aryloxy, (C3-C30)heteroaryl, (C6_C3〇)aryl (cl_C3〇) alkyl, (C6-C30) arylthio, mono or di C1-C30)alkylamino, mono or di(C6-C30)arylamino, tri(C1-C30)alkyldecyl, di(C1-C30)alkyl(C6-C30)aryldecyl , tris(C6 C3〇)arylalkylalkyl, sulfoinyl; A is a monocyclic or polycyclic aromatic ring or a monocyclic or polycyclic ring. Specifically, the lanthanide is selected from the following structures:
£ 95334 11 201217356£ 95334 11 201217356
L!為單鍵或係選自下列結構：L! is a single bond or is selected from the following structures:
;以及 L2為單鍵、伸苯基或伸環己基。 更具體而言，根據本發明之用於有機電子材料的化合 物可藉由下列化合物例示，但並非用以限制本發明。And L2 is a single bond, a phenylene group or a cyclohexyl group. More specifically, the compound for an organic electronic material according to the present invention can be exemplified by the following compounds, but is not intended to limit the present invention.
12 95334 20121735612 95334 201217356
13 95334 20121735613 95334 201217356
根據本發明之用於有機電子材料的化合物可如下列反 應方案1 (不限於此）所示般製備，亦可使用習知類似有 機合成法製備。 [方案1]The compound for an organic electronic material according to the present invention can be produced as shown in the following Reaction Scheme 1 (not limited thereto), and can also be produced by a conventional organic synthesis method. [plan 1]
14 95334, 201217356 其中， 心及R!至私之定義係如化學 化學式1的L,、L2、1、 式1中所定義，而X為鹵素。 第^明提财機電轉光裝置，其係包括第-電極； ϊγΓ 置於該第—電極與該第二電極間之一層 有機層，其巾’該有機層包括-種或多種化學式i 不之用於有機電子材料的化合物。該有機層包括電激發 光層’其中係使用化學式丨之用於有機電子材料的化合物 作為主體材料。 當使用化學式1之用於有機電子材料的化合物作為電 激發光層中的主體時，係包含一種或多種磷光摻雜劑。用 於本發明之有機電激發光裝置的鱗光摻雜劑並無特別限 制’但可為選自化學式4所示之化合物： 化學式4 M1L101L102L103 其中， Μ係選自週期表第7族、第8族、第9族、第10族、 第11族、第13族、第14族、第15族及第16族之金屬所 級成之群組：以及配位子Lm、Lm及1；°3係獨立地選自下 列結構：14 95334, 201217356 wherein, the definition of the heart and R! to the private is as defined in L, L2, 1, Formula 1 of Chemical Formula 1, and X is a halogen. The first embodiment of the present invention includes a first electrode; ϊγΓ is disposed in an organic layer between the first electrode and the second electrode, and the organic layer includes one or more chemical formulas i A compound used in organic electronic materials. The organic layer includes an electroluminescent layer, wherein a compound for an organic electronic material using a chemical formula is used as a host material. When a compound for an organic electronic material of Chemical Formula 1 is used as a host in the electroluminescent layer, one or more phosphorescent dopants are contained. The luminescent dopant used in the organic electroluminescent device of the present invention is not particularly limited 'but may be a compound selected from Chemical Formula 4: Chemical Formula 4 M1L101L102L103 wherein lanthanide is selected from Groups 7 and 8 of the periodic table. Groups of metals of Groups 9, 9th, 10th, 11th, 13th, 14th, 15th, and 16th: and ligands Lm, Lm, and 1; °3 The lines are independently selected from the following structures:
s 15 95334 201217356s 15 95334 201217356
其中，R2。！至Rm係獨立地表示氫、氘、經鹵素取代或 未經取代之（C1-C30)烷基、經（C1-C30)烷基取代或未經取 代之（C6-C30)芳基、或函素；Among them, R2. ! The Rm series independently means hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30) alkyl, (C1-C30)alkyl substituted or unsubstituted (C6-C30) aryl, or Prime
Rm至Rm係獨立表示氫、氛、經取代或未經取代之 (C1-C30)烧基、經取代或未經取代之（C1-C30)院氧基、經 取代或未經取代之（C3-C30)環烷基、經取代或未經取代之 (C2-C30)婦基、經取代或未經取代之（C6-C30)芳基、經取 代或未經取代之單或二（C卜C30)烷基胺基、經取代或未經 取代之單或二（C6-C30)芳基胺基.、SFs、經取代或未經取代 之三（(n-C30)烷基^夕婕基、經取代或未經取代之二（C1-C30) 烷基（C6-C30)芳基矽烷基、經取代或未經取代之三（C6-C30) 芳基碎烧基、氰基或ii素； 16 9533忑 201217356 R22。至R223係獨立地表示氫、氘、經_素取代或未經取 代之（C1-C30)烷基、或經（C1-C30)烷基取代或未經取代之 (C6-C30)芳基； R224及Rm係獨立地表示氫、氣、經取代或未經取代之 (C1-C30)烷基、經取代或未經取代之（C6_C30)芳基、或齒 素’或者Rm及R225可經由具有或不具有稠合環之（C3-C12) 伸烧基或（C3-C12)伸烯基相鏈結以形成脂環族環、或單環 或多環之芳香環； R226表示經取代或未經取代之（C1-C30)炫基、經取代或 未經取代之（C6-C30)芳基、經取代或未經取代之（C5-C30；) 雜芳基、或鹵素；Rm to Rm independently represent hydrogen, aryl, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3 -C30) cycloalkyl, substituted or unsubstituted (C2-C30) aryl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted single or two (C C30) alkylamino group, substituted or unsubstituted mono- or di(C6-C30) arylamino group, SFs, substituted or unsubstituted tris((n-C30)alkyl group , substituted or unsubstituted bis(C1-C30)alkyl (C6-C30) arylalkyl, substituted or unsubstituted tris(C6-C30) aryl alkyl, cyano or ii ; 16 9533 忑 201217356 R22. To R223 independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, or substituted by (C1-C30) alkyl or unsubstituted ( C6-C30) aryl; R224 and Rm independently represent hydrogen, gas, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6_C30) aryl, or dentate' Or Rm and R225 may be via (C3-C12) with or without a fused ring a pendant or (C3-C12)-alkenyl phase chain to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; R226 represents a substituted or unsubstituted (C1-C30) leuko Substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C5-C30;) heteroaryl, or halogen;
Rm至Rm係獨立地表示氫、氘、經取代或未經取代之 (C1-C30)烷基、經取代或未經取代2(C6_C30)芳基、或_ 素；以及 Q為Rm to Rm independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted 2(C6_C30)aryl, or _;
R231 至R242係獨立地表示氫、氘、經_素取代或未經取代之 (C1-C30)烧基、（C1-C30)烧氧基、齒素、經取代或未經取 代之（C6-C30)芳基、氰基或經取代或未經取代之（C5-C30) 環炫基’或者R23,至R242可各自經由伸烧基或伸稀基鏈結至 相鄰取代基以形成螺環或稠合環，或者可各自經由伸烷基 或伸婦基鏈結至Rm或Rm以形成飽和或不飽和的稠合環。 化學式4之磷光摻雜劑化合物係藉由下列化合物例R231 to R242 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, (C1-C30) alkoxy, dentate, substituted or unsubstituted (C6- C30) an aryl group, a cyano group or a substituted or unsubstituted (C5-C30)cyclodecyl group or R23, to R242 may each be bonded to an adjacent substituent via a stretching group or a stretching group to form a spiro ring. Or a fused ring, or each may be linked to Rm or Rm via an alkyl or a thiol group to form a saturated or unsaturated fused ring. The phosphorescent dopant compound of Chemical Formula 4 is exemplified by the following compounds
S 17 95334 201217356S 17 95334 201217356
18 95334 20121735618 95334 201217356
在本發明之有機電子裝置中，有機層除了包括化學式 1所示之用於有機電子材料的化合物之外’可進一步同時 包括一種或多種選自芳基胺（ary lamine)化合物及苯乙烯 基芳基胺（styrylarylamine)化合物所組成之群組的化合 物。芳基胺化合物或苯乙烯基芳基胺化合物係如韓國專利 申請案第 10-2008-0123276 號、第 10-2008-0107606 號或 第10-2008-0118428號中所例示，但不限於此。 再者，於本發明之有機電激發光裝置中，有機層除了 包括化學式1所示之用於有機電子材料的化合物之外，可 進一步包括一種或多種選自下列所組成之群經的金屬：第 1族、第2族、第4周期與第5周期過渡金屬、鑭系金屬 及d-過渡元素之有機金屬’或錯合物化合物。有機層可包 括電激發光層及電荷產生層。 再者’有機層除了包括化學式1所示之用於有機電子 材料的化合物之外，可同時包括一層或多層發射藍光、綠 光或紅光之有機電激發光層，以提供發射白光之有機電激 發光裝置。發射藍光、綠光或紅光之化合物可例示如韓國 專利申請案第 10〜2〇〇8_〇123276 號、第 1〇 2〇〇8 — 〇1〇76〇6 95334 19 201217356 號及第10-2008-0118428號中記載之化合物，但不限於此。 在本發明之有機電激發光裝置中，可將選自硫屬化合 物（chalcogenide)層、金屬鹵化物層及金屬氧化物層之層 體（後文中稱為「表面層」）設置於電極對中之一個或兩個 電極的内表面。更具體而言，可將石夕或紹之金屬硫屬化合 物（包括氧化物）層設置於電激發光介質層之陽極表面，並 可將金屬_化物層或金屬氧化物層設置於電激發光介質層 之陰極表面。藉此可得到操作安定性。硫屬化合物可為例 如 Si〇x(Kxs2)、A10x(lsxsl· 5)、SiON、SiAlON 等。金屬 鹵化物可為，例如LiF、MgFz、CaFz、稀土金屬氟化物等。 金屬氧化物可為例如Cs20、Li20、Mg0、Sr0、Ba0、Ca0等。 在根據本發明之有機電激發光裝置中，較佳亦可將電 子傳輸化合物與還原性摻雜劑之混合區域、或電洞傳輸化 合物與氧化性摻雜劑之混合區域設置於如前所製造之電極 對的至少-個表面上。於該例子中，由於電子傳輸化合物 被還原成陰離子’因而使電子變得更容易自混合區域注入 及傳，至電激發光介質。此外，由於電洞傳輸化合物被氧 化成陽離子，因而使電洞變得更容易自混合區域注入及傳 輸至電激發光介質。較佳之氧化性摻雜劑係包含各種路易 士酸及文體（acxeptQr)化合物。較佳之還原性摻雜劑係包 含驗金屬、驗金屬化合物、驗土金屬、稀土金屬及其混合 物。再者，可藉錢用還原性摻雜·作為電荷產生層來 =具有兩層或更多層電激發光層之發射白光的電激ς光 95334 20 201217356 (有益效果） 由於根據本發明之用於有機電子材料的化合物展現良 好發光效率及優異壽命性質，其可用於製造具有極高操作 壽命之0LED裝置。 (最佳模式） 本發明將進一步說明關於根據本發明之用於有機電子 材料的化合物、其製備方法、以及使用其之裝置的發光性 質。然而，下列實施例僅提供用於例示性說明，而非用以 限制本發明之範疇。 [製備例1 ]化合物4之製備In the organic electronic device of the present invention, the organic layer may further include one or more compounds selected from the group consisting of aryl amines and styryl groups in addition to the compound for organic electronic materials represented by Chemical Formula 1. A compound of the group consisting of styrylarylamine compounds. The arylamine compound or the styrylarylamine compound is exemplified in, for example, Korean Patent Application No. 10-2008-0123276, No. 10-2008-0107606, or No. 10-2008-0118428, but is not limited thereto. Furthermore, in the organic electroluminescent device of the present invention, the organic layer may further comprise, in addition to the compound for the organic electronic material represented by Chemical Formula 1, one or more metals selected from the group consisting of: An organometallic' or complex compound of a transition metal, a lanthanide metal, and a d-transition element of Group 1, Group 2, Period 4, and Cycle 5. The organic layer may include an electroluminescent layer and a charge generating layer. Furthermore, the organic layer may include one or more layers of an organic electroluminescent layer emitting blue, green or red light in addition to the compound for organic electronic material shown in Chemical Formula 1 to provide an organic light emitting white light. Excitation light device. A compound that emits blue light, green light, or red light can be exemplified as Korean Patent Application No. 10~2〇〇8_〇123276, No. 1〇2〇〇8 — 〇1〇76〇6 95334 19 201217356 and 10th. The compound described in -2008-0118428, but is not limited thereto. In the organic electroluminescent device of the present invention, a layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as "surface layer") may be disposed in the electrode pair. The inner surface of one or both of the electrodes. More specifically, a metal chalcogenide (including oxide) layer of Shi Xi or Shao may be disposed on the anode surface of the electro-excitation optical medium layer, and a metal-based layer or a metal oxide layer may be disposed on the electro-excitation light. The cathode surface of the dielectric layer. Thereby, operational stability can be obtained. The chalcogen compound may be, for example, Si〇x (Kxs2), A10x (lsxsl·5), SiON, SiAlON or the like. The metal halide may be, for example, LiF, MgFz, CaFz, a rare earth metal fluoride or the like. The metal oxide may be, for example, Cs20, Li20, Mg0, Sr0, Ba0, Ca0 or the like. In the organic electroluminescent device according to the present invention, it is preferable that the mixed region of the electron transporting compound and the reducing dopant or the mixed region of the hole transporting compound and the oxidizing dopant be disposed as before. At least one surface of the pair of electrodes. In this example, since the electron transporting compound is reduced to an anion', electrons are more easily injected and transported from the mixed region to the electroluminescent medium. In addition, since the hole transporting compound is oxidized to a cation, it becomes easier to inject and transport the hole from the mixed region to the electroluminescent medium. Preferred oxidizing dopants include various Lewis acid and acxept Qr compounds. Preferred reducing dopants include metal, metal-detecting compounds, soil-measuring metals, rare earth metals, and mixtures thereof. Furthermore, it is possible to borrow reductive doping as a charge generating layer = electroluminescent light emitting white light having two or more layers of electroluminescent light layers 95334 20 201217356 (benefit effect) since it is used according to the invention Compounds of organic electronic materials exhibit good luminous efficiency and excellent lifetime properties, which can be used to manufacture OLED devices having extremely high operational lifetimes. (Best Mode) The present invention will further explain the luminescent properties of the compound for an organic electronic material according to the present invention, a process for producing the same, and a device using the same. However, the following examples are provided for illustrative purposes only and are not intended to limit the scope of the invention. [Preparation Example 1] Preparation of Compound 4
化合物1-1之製備 令10克（g)(49. 5毫莫耳（mmol)) 1-漠-2-硝基苯、1〇. 2 s 21 95334 201217356 g (59.3 mmol) 1-萘硼酸' 2〇〇此甲苯、5〇此乙醇及別 niL水混合’接著添加2· 9 g (2 5 mm〇1)pd(pph3)4及汕5 g (148. 3 mmol)碳酸鉀。此混合物於12〇〇c攪拌5小時，接 著冷卻至室溫’之後以4〇 mL氯化銨水溶液中止反應。所 獲混合物以500 mL的EA萃取，接著以1〇〇mL蒸餾水^洗。 所得有機層以無水MgS〇4乾燥，減壓處理以移除有機溶劑， 之後以矽膠管柱層析純化，藉此獲得化合物丨〜丨 81%)。 化合物1-2之製備 將l〇g (40. 1 mm〇i)化合物溶於1〇〇此的12_ 二氣苯，接著於其中添加1〇〇 mL三乙氧基膦。此反應混合 物於150°C攪拌20小時，接著冷卻至室溫，令溶劑，亦即 1，2-二氯笨與二乙氧基膦以真空蒸餾移除。餘留的有機材 料以300 mL的乙醇乙酯（EA)萃取，之後以40 mL蒸餾水清 洗。所得有機層以無水MgSCh乾燥，減壓處理以移除有機溶 劑’之後以矽膠管柱層析純化，藉此獲得化合物卜2 (7g， 80%)。 化合物1-3之製備 將 20g (92 mmol)化合物 1-2 及 43. 5g (184 mmol) 1-、/臭-4-碘化苯溶於500 mL甲苯，添加8. 8g (46 mmol)CuI、 6.2 毫升（mL)(92 mmol)二胺基乙烷及 58. 7g (276 mmol) K3P〇4，接著回流30小時。反應混合物冷卻至室溫，之後以 50 mL的2· 0Μ鹽酸水溶液中止反應，所獲混合物以1升（L) 的EA萃取，接著以200 mL蒸餾水清洗。所得有機層以無 22 95334 201217356 水MgS〇4乾燥，減壓處理以移除有機溶劑，之後以矽膠管柱 層析純化，藉此獲得化合物卜3 (19g，56%)。 化合物1-4之製備 將19g (51 mmol)化合物卜3溶於25〇乩的THF，接 著冷卻至—78°C，之後於添加24.5 mL的正丁基鋰 (n-BuLi ’ 2· 5M’於己烷中）。此混合物於_78ι攪拌丨小時， 添加8· 5 mL的B(OMe)3，攪拌2小時，以1〇〇虬氯化銨 水溶液中止反應。接下來，所得混合物以5〇〇 mL的EA萃 取，然後以100 mL蒸餾水清洗。所得有機層以無水MgS〇4 乾燥’減壓處理以移除有機溶劑，以及再結晶，藉此獲得 化合物 1-4 (14g，81%)。 化合物2-1之製備 將 50g (247 mmol)l，2-丙二烯合苐（fluoranthene)溶 於1 L·硝基苯，緩慢滴加以2〇〇 raL硝基苯稀釋之12 mL (234· 7 mmol)溴。將溶液完全滴加完後，反應溶液於室溫 授拌20小時。於反應溶液添加5〇〇 mL硫代硫酸鈉氣化物 飽和水溶液（aqUe0US saturated sodium thiosulfate chloride) ’以終止反應。所得混合物以3 l的EA萃取， 接著以1 L蒸餾水清洗。所得有機層以無水MgS〇4乾燥，減 壓處理以移除有機溶劑，使用矽膠過濾，接著再結晶，藉 此獲得化合物2-1 (65g，94%)。 化合物2-2之製備 將 24. 5g (87. 1 mmol)化合物 2-1 溶於 500 mL 之 THF， 冷卻至-78°C，添加45 mL的n-BuLi (2. 5M，於己烧中）， 23 95334 201217356 接著攪拌1小時。接下來，於此混合物添加15 mL的 B(OMe)3,攪拌2小時，以25〇mL氣化銨水溶液中止反應。 所得混合物以1 L的EA萃取，接著以200 mL蒸餾水清洗。 所得有機層以無水MgSCh乾燥，減壓處理以移除有機溶劑， 接著再結晶，藉此獲得化合物2-2 (14g，65%)。 化合物2-3之製備 令 8. lg (40· 6 mmol) 2, 4-二氯喹唑啉、l〇g (40. 6 mmol) 化合物2_2、200 mL曱苯、50 mL乙醇及50 mL水混合， 接著添加 1. 9g (1. 64 mmol)Pd(PPh3)4及 12. 9g (122 mmol) K2C〇3。此混合物於i2〇°c攪拌5小時，冷卻至室溫，之後 以200 mL氯化銨水溶液中止反應。所得混合物以500 mL 的EA萃取，接著以5〇 mL蒸餾水清洗。所得有機層以無水 MgS〇4乾燥，減壓處理以移除有機溶劑，使用矽膠過濾，接 著再結晶，藉此獲得化合物2-3 (10g，68%)。 化合物4之製備 令 5. 0g (13. 7 mmol)化合物 2-3 及 5. 54g (16. 4 mmol) 化合物1-4與100 mL曱苯、20 mL乙醇及20 mL水混合， 之後添加 1.6g (1.4inmol)Pd(PPh3)4 及 5.7g (41.1mmol) K2CO3。此混合物於i20°C攪拌5小時，冷卻至室溫，以20 mL 氣化銨水溶液中止反應。所得混合物以250 mL的EA萃取， 接著以30 raL蒸餾水清洗。所得有機層以無水MgS〇4乾燥， 減壓處理以移除有機溶劑，使用矽膠過濾，接著再結晶， 藉此獲得化合物4 (5. 9g，69%)。 MS/FAB : 621. 22(實測值），621. 73(計算值） 24 95334 201217356 [實施例1]使用根據本發明之用於有機電子材料的化 合物製造0led裝置 使用根據本發明之用於有機電子材料的化合物製造 OLED裝置。首先，由0LED(Samsung CorninS所製造）用玻 璃所獲得之透明電極ΙΤ0薄膜（15Ω/ΙΙ])，依序以三氯乙 烯、丙酮、乙醇及蒸顧水進行超音波清洗，並儲存於異丙 醇中備用。然後，將ΙΤ0基板裝配於真空沈積裝置之基板 夾中，ϋ將4, 4’，4’ ’ -參（N, N-(2-萘基）-苯基胺基）三苯胺 (2-TNATA)置於該真空沈積裝置之單元（cei1)+，然後抽氣 使該腔室内達到1(Γ1 2托（ton:)真空。接著，對該單元施加 電流以蒸發2-TMTA，從而於ΙΤ0基板上形成厚度為6〇奈 米（nm)之電洞注入層。接下來，將况肸雙（α_萘基）_况趴 二苯基-4, 4’ -二胺（ΝΡΒ)置於真空沈積襞置之另一單元 中，並對該單元施加電流以蒸發ΝΡΒ，從而於該電洞注^ f上形f厚度為20 nm之電洞傳輪層。此外，將於1〇_2仂汀 藉真空昇華而純化之根據本發明的化合物3置於直 ίΓιΓι「乙早：中作為主體材料，並將雙—(卜笨基異喹啉基) -《π )醯丙酮酯（（piq)2Ir(acac))置於另一單元 雜劑。接著，以不同速率蒸發該兩種材料， ^摻雜4至2ΰ重量％，於該電洞傳輸層上氣相沉積厚度 為30mn之電激發光層。接下來 J :…(8,基㈣ 層。然後，沈積厚声蛊1 5 9nm …讣馮电于得輸 quinolate，Liq):為 之 8_殘基喹啉鐘(lithium W作為電子U層後’使用另—真空氣相沈 25 1 2 95334 201217356 積裝置形成厚度為15〇nm之鋁（A1)陰極，以製造0LED。 用於該0LED之各化合物，係於1〇-6 t〇rr藉真空昇華 而純化。 結果’於6. 5 V電壓有電流μ. 〇毫安培（fflA)/平方公 分（cm)流動’且發出1〇52燭光（cd)/平方公分（cm2)之紅 光。 [實施例2] 除了改用化合物4作為電激發光層中的主體材料之 外，以實施例1中的相同方法來製造0LED裝置。 結果’於7. 5V電壓有電流14. 〇 mA/cm2流動，且發出 1060 cd/cm2 之紅光。 [實施例3] 除了改用化合物14作為電激發光層中的主體材料之 外，以實施例1中的相同方法來製造0LED裝置。 結果，於6. 8V電壓有電流14.丨^/⑽^流動，且發出 1030 cd/cm2 之紅光。 [實施例4] 除了改用化合物20作為電激發光層中的主體材料之 外，以實施例1中的相同方法來製造〇LED裝置。 結果，於6. 4V電壓有電流14. 2 mA/cm2流動，且發出 1048 cd/cm2 之紅光。 [比較例1 ] 除了改用4,4’-雙（咔唑〜9—基）聯苯（(：卯）代替本發明 之化合物作為電激發光層中的主體材料、以及將雙（2_曱基 95334 26 201217356 -8-經基喹啉基）（對笨基酚基） quinolinato)(p-phenyl-phenolato)alurainum(111)? BAlq) 作為電洞阻擋層之外，以實施例1中的相同方法來製造 0LED裝置。 結果，於7. 5V之電壓有電流15. 3 mA/cm2流動，且證 實發出1000 cd/cm2之紅光。 與習知材料相比，根據本發明之用於有機電子材料的 化合物係具有優異之性質。此外，使用根據本發明之用於 有機電子材料的化合物（具有丙二烯合苐取代基）作為主體 材料的有機電激發光裴置’係具有優異之電激發光性質及 下降0· 7至1. 2 V之驅動電壓，從而增加功率效率以及改 善功率耗損。 雖以說明為目的而揭示本發明之較佳具體實施例，本 發明所屬技術領域中具有通常知識者咸暸解，可在不偏離 所附申請專利範圍揭露之本發明的範疇及精神的情況下， 進行各種修飾、添附與置換。 【圖式簡單說明】 無。 【主要元件符號說明】 無。 s 95334Preparation of Compound 1-1 10 g (g) (49. 5 mmoles (mmol)) 1-di- 2-nitrobenzene, 1 〇. 2 s 21 95334 201217356 g (59.3 mmol) 1-naphthaleneboronic acid ' 2 〇〇 this toluene, 5 〇 this ethanol and other niL water mixed' then add 2· 9 g (2 5 mm 〇 1) pd (pph3) 4 and 汕 5 g (148. 3 mmol) potassium carbonate. The mixture was stirred at 12 ° C for 5 hours and then cooled to room temperature and then quenched with 4 mL of aqueous ammonium chloride. The resulting mixture was extracted with 500 mL of EA, followed by 1 mL of distilled water. The obtained organic layer was dried over anhydrous Mg.sub.4, and then worked under reduced pressure to remove organic solvent, and then purified by silica gel column chromatography, whereby compound 丨~丨 81%). Preparation of Compound 1-2 A compound of 1 〇g (40. 1 mm 〇i) was dissolved in 1 二 2 of 2 benzene, followed by 1 〇〇 mL of triethoxy phosphine. The reaction mixture was stirred at 150 ° C for 20 hours, then cooled to room temperature, and the solvent, i.e., 1,2-dichlorobenzene and diethoxyphosphine, was removed by vacuum distillation. The remaining organic material was extracted with 300 mL of ethyl ethoxide (EA) and then washed with 40 mL of distilled water. The obtained organic layer was dried over anhydrous MgSO.sub.sub.sub.sub.sub. The compound 1-3 was prepared by dissolving 20 g (92 mmol) of compound 1-2 and 43.5 g (184 mmol) of 1-, / odor 4-pyridinium benzene in 500 mL of toluene, and adding 8. 8 g (46 mmol) of CuI. 6.2 ml (mL) (92 mmol) of diaminoethane and 58.7 g (276 mmol) of K3P〇4, followed by reflux for 30 hours. The reaction mixture was cooled to room temperature, and then the reaction was quenched with 50 mL of aq. EtOAc. EtOAc. The obtained organic layer was dried over anhydrous water (MgSO.sub.2), </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> <RTIgt; Preparation of Compound 1-4 19 g (51 mmol) of Compound 3 was dissolved in 25 Torr of THF, followed by cooling to -78 ° C, followed by the addition of 24.5 mL of n-butyllithium (n-BuLi ' 2 5 M' In hexane). The mixture was stirred at _78 for 丨 hour, and 8·5 mL of B(OMe)3 was added and stirred for 2 hours, and the reaction was quenched with 1 〇〇虬 aqueous ammonium chloride. Next, the resulting mixture was extracted with 5 mL of EA and then washed with 100 mL of distilled water. The obtained organic layer was dried under reduced pressure of anhydrous MgSO 4 to remove organic solvent and recrystallized, whereby compound 1-4 (14 g, 81%) was obtained. Preparation of Compound 2-1 50 g (247 mmol) of 1,2-propadienene (fluoranthene) was dissolved in 1 L·nitrobenzene, and slowly diluted with 2 〇〇raL of nitrobenzene diluted 12 mL (234· 7 mmol) bromine. After the completion of the dropwise addition of the solution, the reaction solution was stirred at room temperature for 20 hours. To the reaction solution, 5 〇〇 mL of sodium thiosulfate chloride (aq) was added to terminate the reaction. The resulting mixture was extracted with 3 l of EA and then with 1 L of distilled water. The obtained organic layer was dried over anhydrous MgSO.sub.4, and reduced to remove organic solvent, filtered, and then recrystallized to give compound 2-1 (65 g, 94%). Preparation of compound 2-2 24. 5 g (87. 1 mmol) of compound 2-1 was dissolved in 500 mL of THF, cooled to -78 ° C, and added 45 mL of n-BuLi (2.5 M in hexane ), 23 95334 201217356 followed by stirring for 1 hour. Next, 15 mL of B(OMe)3 was added to the mixture, and the mixture was stirred for 2 hours, and the reaction was quenched with a 25 mL aqueous solution of ammonium sulfate. The resulting mixture was extracted with 1 L of EA and then with 200 mL of distilled water. The obtained organic layer was dried over anhydrous MgSO.sub.sub.sub.sub.sub.sub. Preparation of compound 2-3 8. lg (40·6 mmol) 2, 4-dichloroquinazoline, l〇g (40. 6 mmol) Compound 2_2, 200 mL of hydrazine, 50 mL of ethanol and 50 mL of water were mixed. Then, 1. 9 g (1. 64 mmol) of Pd(PPh3)4 and 12.9 g (122 mmol) of K2C〇3 were added. This mixture was stirred at i2 ° C for 5 hours, cooled to room temperature, and then quenched with 200 mL of aqueous ammonium chloride. The resulting mixture was extracted with 500 mL of EA, followed by 5 mL of distilled water. The obtained organic layer was dried over anhydrous MgSO.sub.4, and evaporated to remove organic solvent, filtered, and then recrystallized to give compound 2-3 (10 g, 68%). Preparation of compound 4 5. 0 g (13. 7 mmol) of compound 2-3 and 5.54 g (16. 4 mmol) of compound 1-4 was mixed with 100 mL of terpene, 20 mL of ethanol and 20 mL of water, followed by addition of 1.6. g (1.4 inmol) Pd(PPh3)4 and 5.7 g (41.1 mmol) K2CO3. The mixture was stirred at i20 ° C for 5 hours, cooled to room temperature, and quenched with 20 mL of aqueous ammonium sulfate. The resulting mixture was extracted with 250 mL of EA and then washed with 30 raL of distilled water. The obtained organic layer was dried over anhydrous MgSO4, and evaporated to dryness to remove organic solvent, and filtered, and then recrystallized to give Compound 4 (5.9 g, 69%). MS/FAB: 621. 22 (measured value), 621. 73 (calculated value) 24 95334 201217356 [Example 1] Using a compound for an organic electronic material according to the present invention to manufacture an OLED device using the organic device according to the present invention Compounds of electronic materials manufacture OLED devices. First, a transparent electrode ΙΤ0 film (15 Ω / ΙΙ) obtained by using OLED (manufactured by Samsung Cornin S) was ultrasonically washed with trichloroethylene, acetone, ethanol, and steamed water, and stored in isopropyl alcohol. Alternate in alcohol. Then, the ΙΤ0 substrate was assembled in a substrate holder of a vacuum deposition apparatus, and 4, 4', 4' '-parameter (N, N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) Placed in the unit (cei1)+ of the vacuum deposition apparatus, and then evacuated to bring the chamber to 1 (Γ1 2 Torr: vacuum. Then, a current is applied to the unit to evaporate 2-TMTA, thereby ΙΤ0 substrate A hole injection layer having a thickness of 6 nanometers (nm) is formed thereon. Next, a condition of bis(α_naphthyl)_diphenyl-4,4'-diamine (ΝΡΒ) is placed in a vacuum. Depositing another unit in the chamber and applying a current to the unit to evaporate the crucible, thereby forming a hole-transmitting layer with a thickness of 20 nm on the hole. In addition, it will be 1〇_2仂The compound 3 according to the present invention purified by vacuum sublimation is placed in a straight ΓιΓι "B early: as a host material, and bis-(Bus-iso-isoquinolyl)-"π"pyridinyl ester ((piq) 2Ir(acac)) is placed in another unit impurity. Then, the two materials are evaporated at different rates, ^4 to 2% by weight, and the vapor deposition thickness on the hole transport layer is 30mn. Excitation layer. Next J: ... (8, base (four) layer. Then, deposit thick sound 蛊 1 5 9nm ... 讣 电 于 得 quin quin quin quin Li Li quin quin quin quin quin quin quin quin quin quin quin quin lith lith lith lith lith lith lith lith lith lith lith lith lith After the electron U layer, an aluminum (A1) cathode having a thickness of 15 〇nm is formed by using a vacuum chamber 25 1 2 95334 201217356 to produce an OLED. The compound for the OLED is at 1 -6. T〇rr was purified by vacuum sublimation. The result 'current at 6.5 V has a current μ. 〇 milliamperes (fflA) / square centimeter (cm) flow 'and issued 1 〇 52 candelas (cd) / cm ^ 2 (cm 2 ) [Example 2] The OLED device was fabricated in the same manner as in Example 1 except that the compound 4 was used as the host material in the electroluminescent layer. The result was a current of 14.5 V. 〇 mA/cm 2 flows, and emits red light of 1060 cd/cm 2 . [Example 3] An OLED device was manufactured in the same manner as in Example 1 except that Compound 14 was used as a host material in the electroluminescent layer. As a result, a current of 14. V^/(10)^ flows at a voltage of 6.8 V, and a red light of 1030 cd/cm 2 is emitted. [Embodiment 4] The 〇LED device was fabricated in the same manner as in Example 1 except that the compound 20 was used as the host material in the electroluminescent layer. As a result, a current of 14.2 mA/cm2 was flowed at a voltage of 6.4 V, and 1048 cd was issued. Red light of /cm2 [Comparative Example 1] In addition to using 4,4'-bis(carbazole~9-yl)biphenyl ((:卯) instead of the compound of the present invention as a host material in the electroluminescent layer, And a double (2_mercapto 95334 26 201217356 -8-pyridyl quinolate) (p-phenyl-phenolato) alurainum (111)? BAlq) as a hole barrier An OLED device was manufactured in the same manner as in Example 1. As a result, a current of 5.3 mA/cm2 was flowed at a voltage of 7.5 V, and a red light of 1000 cd/cm2 was confirmed. The compound for an organic electronic material according to the present invention has excellent properties as compared with the conventional material. Further, the organic electroluminescence device using the compound for organic electronic materials (having a propadiene ruthenium substituent) as a host material according to the present invention has excellent electroluminescence properties and a decrease of 0.7 to 1 . 2 V drive voltage, which increases power efficiency and improves power consumption. While the invention has been described with respect to the preferred embodiments of the present invention, Various modifications, additions and substitutions are made. [Simple description of the diagram] None. [Main component symbol description] None. s 95334
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| TWI579285B (en) * | 2012-07-05 | 2017-04-21 | 東麗股份有限公司 | Light emitting element material and light emitting element |
| TWI631109B (en) * | 2013-03-15 | 2018-08-01 | 陶氏全球科技有限責任公司 | Quinazoline derived compounds for electronic films and devices |
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| TW201213502A (en) | 2010-08-05 | 2012-04-01 | Idemitsu Kosan Co | Organic electroluminescent element |
| KR20120038060A (en) * | 2010-10-13 | 2012-04-23 | 롬엔드하스전자재료코리아유한회사 | Novel compounds for organic electronic material and organic electroluminescent device using the same |
| KR101775188B1 (en) * | 2012-11-21 | 2017-09-05 | 주식회사 엘지화학 | Fluoranthene compound and organic electronic device comprising the same |
| KR20160002675A (en) | 2013-05-02 | 2016-01-08 | 이데미쓰 고산 가부시키가이샤 | Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device |
| EP3150579B1 (en) | 2014-05-28 | 2021-02-24 | Toray Industries, Inc. | Fluoranthene derivative, electronic device containing same, light-emitting element, and photoelectric conversion element |
| KR102360782B1 (en) * | 2017-07-20 | 2022-02-10 | 삼성디스플레이 주식회사 | Organic light emitting device |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003109765A (en) * | 2001-09-28 | 2003-04-11 | Canon Inc | Organic light emitting device |
| JP4646494B2 (en) * | 2002-04-11 | 2011-03-09 | 出光興産株式会社 | Novel nitrogen-containing heterocyclic derivative and organic electroluminescence device using the same |
| US7867629B2 (en) * | 2003-01-10 | 2011-01-11 | Idemitsu Kosan Co., Ltd. | Nitrogenous heterocyclic derivative and organic electroluminescent element employing the same |
| JP4970934B2 (en) * | 2004-03-19 | 2012-07-11 | 出光興産株式会社 | Organic electroluminescence device |
| JP4585786B2 (en) * | 2004-04-01 | 2010-11-24 | キヤノン株式会社 | Light emitting element and display device |
| JP4478555B2 (en) * | 2004-11-30 | 2010-06-09 | キヤノン株式会社 | Metal complex, light emitting element and image display device |
| JP2007261969A (en) * | 2006-03-28 | 2007-10-11 | Canon Inc | 2,6-Fluorenyl-substituted pyridine compound and organic light-emitting device using the same |
| JP2007308477A (en) * | 2006-04-20 | 2007-11-29 | Canon Inc | Compound and organic light emitting device |
| WO2010021524A2 (en) * | 2008-08-22 | 2010-02-25 | 주식회사 엘지화학 | Material for organic electronic device, and organic electronic device using the same |
-
2010
- 2010-08-31 KR KR1020100084679A patent/KR20120020818A/en not_active Ceased
-
2011
- 2011-08-30 JP JP2013525846A patent/JP5830097B2/en not_active Expired - Fee Related
- 2011-08-30 WO PCT/KR2011/006412 patent/WO2012030145A1/en not_active Ceased
- 2011-08-30 CN CN2011800499936A patent/CN103201273A/en active Pending
- 2011-08-31 TW TW100131227A patent/TW201217356A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI579285B (en) * | 2012-07-05 | 2017-04-21 | 東麗股份有限公司 | Light emitting element material and light emitting element |
| TWI631109B (en) * | 2013-03-15 | 2018-08-01 | 陶氏全球科技有限責任公司 | Quinazoline derived compounds for electronic films and devices |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2012030145A1 (en) | 2012-03-08 |
| CN103201273A (en) | 2013-07-10 |
| JP5830097B2 (en) | 2015-12-09 |
| KR20120020818A (en) | 2012-03-08 |
| JP2013542176A (en) | 2013-11-21 |
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