TW555831B - Electroluminance device - Google Patents

Electroluminance device Download PDF

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TW555831B
TW555831B TW90103502A TW90103502A TW555831B TW 555831 B TW555831 B TW 555831B TW 90103502 A TW90103502 A TW 90103502A TW 90103502 A TW90103502 A TW 90103502A TW 555831 B TW555831 B TW 555831B
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butyl
organic electroluminescence
light
layer
organic
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TW90103502A
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Yi-Fan Wang
Weng-Kou Wen
Po-Yen Lu
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Ind Tech Res Inst
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Abstract

An blue organic EL device includes an anode, a cathode and an EL element arranged between the two. The EL element includes a substance represented by the following chemical formula: in which m, n=1-3; the substitute R is selected from a group consisting of t-butyl, phenyl, methylphenyl, naphehyl and heterocyclic compound. The EL element is highly efficient, lower-voltage operative and easy to be synthesized.

Description

555831 五、發明說明ο) 【發明的應用領域】 本發明係有關一種應用於有機電致發光裝置,具有 高螢光效率,低驅動電壓且容易合成的有機藍色螢光材 料。 【發明的背景及相關技術】 自1 9 8 7年柯達開發第一個高效率綠光有機電致發光 裝置(Organic electroluminescence device)後,便弓| 起各界的注意。有機電致發光裝置的動作原理如「第1 圖」所示,係將有機薄膜或稱有機電致發光元件 (Electroluminescence Element,以下簡稱為EL 元件)包 夾於陰極3及陽極1之間,通過電流,使電子、電洞兩載 子(carrier)在有機層相遇再結合而放光。 一般簡單的有機電致發光裝置的兩層元件結構為: 在陽極1(為一種位於透明玻璃2之表面的IT0透明導電膜) 上蒸鑛電洞傳遞層(hole transport layer),電洞傳遞 層6上再蒸鑛發光層(light emitting layer)5,此發光 層具備傳輸電子及發光的能力;最後於電子傳遞層4上再 蒸鑛金屬電極3(大致上含有Mg、Li、A1等金屬元素)當作 陰極。除此之外還有一種多層結構元件(如「第2圖」 所示),主要是將其它的有機材料蒸鍍於電極與電洞傳 遞材料與電子傳遞材料間,包含電洞注入層(Η ο 1 e Injection Layer, HIL)7 、電洞傳遞層(Hole Transport Layer, HTL)6 、有機發光層(light emitting layer, EML)5 以及電子傳遞層4(Electron Transport Layer,555831 V. Description of the invention [Application field of the invention] The present invention relates to an organic blue fluorescent material applied to an organic electroluminescence device, which has high fluorescence efficiency, low driving voltage, and is easy to synthesize. [Background of the Invention and Related Technology] Since Kodak developed the first high-efficiency green light organic electroluminescence device (Organic electroluminescence device) in 1987, the bow has taken the attention of all walks of life. The operating principle of the organic electroluminescence device is as shown in "Figure 1". An organic thin film or an organic electroluminescence element (hereinafter referred to as an EL element) is sandwiched between a cathode 3 and an anode 1. The current causes the two carriers of electrons and holes to meet and recombine in the organic layer to emit light. A two-layer element structure of a generally simple organic electroluminescence device is: on the anode 1 (an IT0 transparent conductive film on the surface of transparent glass 2), a hole transport layer is deposited on the anode, and the hole transport layer is 6 light-emitting layer (light emitting layer) 5 on top, this light-emitting layer has the ability to transport electrons and emit light; finally on the electron transfer layer 4 is re-steamed on the metal electrode 3 (roughly containing Mg, Li, A1 and other metal elements ) As the cathode. In addition, there is also a multilayer structure element (as shown in "Figure 2"). Other organic materials are mainly deposited between the electrode and the hole transfer material and the electron transfer material. ο 1 e Injection Layer (HIL) 7, Hole Transport Layer (HTL) 6, organic light emitting layer (EML) 5, and Electron Transport Layer 4 (Electron Transport Layer,

555831 五、發明說明(2) ETL)或是電子注入層(Electron Injection Layer, EIL) 等,藉以提高載子注入效率,進而達到降低驅動電壓及 增加載子再結合機率(carrier recombination probability) 〇 由於EL元件具有:(1)高亮度(2)自發光(3)低驅動電 壓(4 )無視角(5 )簡易製程的特性,所以能夠應用於平面 顯示器上。但是EL元件發展至今,仍有許多技術上的 題有待突破’例如發光效率不佳,亮度不理想, 作壽命較短等問題。而影響上述問題的因素^致上勺 有: 仿 1 子雙注 入夾於 料層遷 來,因 之發光 專利申 洞注入 件的發 2 發放能 能量變 累積的 象,甚 L 7L· 入型的發光器,電V與’電γ二是陪-種载 其間,有機材料層,注入的電極注 移,取後相遇所激發的能量再二有機材 此,電極注入栽子的能力或=而釋放出 亮度與發光效率的重要因素之一柝疋決定EL元件 請第8 6 1 0 1 5 5 1銳乙案,其中便揭,例如中華民國 層材料,以期藉由提昇載子的注各J 一種新的電 光效率與亮度。 八效率增加E L元 、EL元件内含的雜質;在^元件的 的過程中,内含的雜質除了會使栽子因相遇而激 成熱能而釋放,導致其發光的效$子激發的部分 熱能亦會影響有機材料發生結晶牟與亮度降低, 至發生熱分解而影響元件的壽命。再結晶)的現555831 V. Description of the invention (2) ETL) or Electron Injection Layer (EIL), etc., in order to improve the efficiency of carrier injection, thereby reducing the driving voltage and increasing the carrier recombination probability. EL elements have the characteristics of (1) high brightness, (2) self-luminous, (3) low driving voltage, (4) no viewing angle, and (5) a simple process, so they can be applied to flat-panel displays. However, until the development of EL elements, there are still many technical problems to be broken through, such as poor luminous efficiency, unsatisfactory brightness, and short life. The factors that affect the above problems are as follows: Imitation of a double-injector is moved between the layers, so the light emitting patent application hole injection part 2 releases the energy that can accumulate, which is very L 7L · type. In the light emitter, the electric V and the electric γ are accompanied by the seed, the organic material layer, and the injected electrode are implanted, and the energy excited by the encounter is then again the organic material. The ability of the electrode to implant into the plant or = is released. One of the important factors of brightness and luminous efficiency. Decide the EL element in the 8th 6 1 0 1 5 5 1 case, which will be disclosed, for example, the Republic of China layer material, in order to improve the carrier's injection. New electro-optic efficiency and brightness. Eight efficiency increase the impurities contained in the EL element, EL element; in the process of the element, in addition to the impurities contained in the plant will be released due to the thermal energy caused by the encounter and release, resulting in its luminous effect. It will also affect the crystallization of organic materials and decrease in brightness, until thermal decomposition occurs and affect the life of the device. Recrystallization)

第9頁 555831 五、發明說明(3) 一'"一"" " --- 膝a Γ f目前應用有機發光二極體(0LED)的顯示器,已 ^m單色、多衫以及全彩等多種型式,關於全彩OLED 的π構如「第3A〜3C圖」所示,包括有: !三色發光材料獨立發光型;主要是將三種發光材料 * 0EL2,0EL3)分別精密的塗佈於晝素(pixel )中, 透過產生R、G、B三色光而合成所需之色光。Page 9 555831 V. Description of the invention (3) A '" 一 " " --- Knee a Γ f Currently applied organic light emitting diode (0LED) display, has been ^ m monochrome, multi-shirt And full-color, and other types, the π structure of full-color OLED is as shown in "Figure 3A ~ 3C", including:! Three-color light-emitting materials independent light-emitting type; mainly three light-emitting materials * 0EL2, 0EL3) precision It is coated in day pixels (pixels), and generates the required color light by generating three colors of R, G, and B.

誌a ί色轉換型;主要是使用藍色發光材料(B-0EL)發出 j色光源,經由預先做好的光色轉換薄膜(F丨),而將藍 二轉交為紅(R )綠(G )兩種色光,與前者不同的是藍光發 光材料疋全面的薄膜,不需製作對應p i χ e 1的圖形;以及 *形色濾光膜型;主要是利用白色發光材料(W_〇EL)為 为光,配合如同L C D的彩色濾光膜(f 2 ),來達到全彩的方 法0 其中又以前二者的發展較為快速且已有產品公開展 示’但是,利用色轉換的方法需要有高效率的藍光材 料’而一般藍光材料效率低且需高驅動電壓,甚至需要 繁靖的有機合成步驟,使產率降低,提高生產成本。而 已知的藍光材料有例如在已公開的美國專利第5 9 3 5 7 2 1號 中所揭露的9, 10-di-(2-naphthyl)anthracene derivatives,以及美國專利第5972247號之中所揭露的 9, 10-bis(3’ , 5’ -diaryl)phenylanthracene志 a ί color conversion type; mainly use blue light-emitting material (B-0EL) to emit j-color light source, through the pre-made light color conversion film (F 丨), and transfer the blue two to red (R) green ( G) Two kinds of color light. The difference from the former is the blue light-emitting material 疋 comprehensive film, which does not need to make a pattern corresponding to pi χ e 1; and the * shape color filter film type; mainly uses white light-emitting material (W_〇EL ) Is a method of light that is matched with a color filter film (f 2) like LCD to achieve full color. Among them, the former two have developed rapidly and existing products have been publicly displayed. However, the method of using color conversion requires High-efficiency blue light materials', while general blue light materials have low efficiency and require high driving voltages, and even require tedious organic synthesis steps to reduce yields and increase production costs. Known blue light materials include, for example, 9, 10-di- (2-naphthyl) anthracene derivatives disclosed in published U.S. Patent No. 5 9 3 5 7 2 1 and U.S. Patent No. 5,972,247. 9, 10-bis (3 ', 5' -diaryl) phenylanthracene

d e r i v a t i v e s,但是這兩件已公開之技術的藍光材料,其 發光效率均不理想。 【發明之目的與概述】d e r i v a t i v e s, but the luminous efficiency of these two disclosed blue light materials is not ideal. [Objective and Summary of the Invention]

第10頁 555831 五、發明說明(4) 本專利主要目的是提供高效率、低驅動電壓且簡易 5成之藍光材料。 r H日月主要是將一種高螢光效率之藍色螢光材料 9’ 1〇 —求基蒽(9, 10 — (diphenyl)anthracene)」的 結構修正’合成不對稱結構,並於其上添加立體障礙大 之取代基(steric-hindrance substitute group),降低 其再結晶(r e c r y s t a 1 1 i z a t i ο η )狀況,而得到一高效率、 低驅動電壓之藍色螢光材料。 本發明所揭露的EL元件,係包括由下式所代表的一 種物質:Page 10 555831 V. Description of the invention (4) The main purpose of this patent is to provide a high-efficiency, low driving voltage and simple 50% blue light material. r H Sun and Moon is mainly to synthesize an asymmetric structure by adding the structure modification of 9 ′ 10—Qi anthracene (9, 10 — (diphenyl) anthracene) ”, a high fluorescent efficiency blue fluorescent material, and adding a three-dimensional structure to it. A steric-hindrance substitute group with a large barrier reduces its recrysta (recrysta 1 1 izati ο η) condition to obtain a blue fluorescent material with high efficiency and low driving voltage. The EL element disclosed in the present invention includes a substance represented by the following formula:

其中m, ,取代基R係為相同或不同且選自於包 含有第三丁基(t-butyl)、苯基(phenyl)、甲基苯基 (methy lpheny 1 )、萘基(naphenyl)、以及雜環族化合物 (heterocyclic bompound)的群族。 【較佳實施例說明】 請參閱「弟4圖」’本發明所揭露的有機電致發光Where m, and the substituents R are the same or different and are selected from the group consisting of t-butyl, phenyl, methylphenyl (methy lpheny 1), naphthyl (naphenyl), And groups of heterocyclic bompounds. [Description of the preferred embodiment] Please refer to "Picture 4" of the organic electroluminescence disclosed in the present invention

第11頁 555831 五、發明說明(5) 裝置(EL device),愛包括有一陽極1〇、一陰極20以及一 包夾於其間的有機電致元件(EL element) 30 ;其中的陽 極10係為ITO透明導電膜,係以濺鍍或是蒸鍍的方式附著 於玻璃或是透明的塑膠基板40 ;陰極20則是含有鎂 (Mg)、鋰(Li )、鋁(A1 )等的金屬電極;EL元件30則是一 種包含有:電洞注入層(11〇16-:[114|6(:1;丨〇1118丫6]:)301,電 洞傳遞層(hole-transport layer)302,發光層(light emitting layer) 303,以及電子傳遞層 (electron-transport layer)304等多層結構的有機電致 元件(EL element),其構成了有機電致發光裝置結構中 的發光層(light emitting layer, EML)。 「9, 1 0 -二苯基蒽(9, 10 -(diphenyl)anthracene)」係為一種具有高螢光效率 的藍色螢光材料(blue fluorescence materials),但是 在製作元件時會有再結晶(recrystallization)現象。本 發明將此一藍色螢光材料的分子結構修正,合成不對稱 的分子結構,並於其上添加立體障礙大之取代基 (steric-hindrance substitute group),以降低其再結 晶狀況,而獲得一種高效率、低驅動電壓、以合成容易 的新的藍色螢光材料,再利用此種新的藍色螢光材料製 成發光效率佳的藍色EL元件。 而本發明所揭露的E L元件,係用以構成有機電致發 光裝置中的發光層(light emitting layer, EML),其係 包括由下式(1 )所代表的一種物質:Page 11 555831 V. Description of the invention (5) Device (EL device), including an anode 10, a cathode 20, and an organic element 30 (EL element) sandwiched between them; the anode 10 is ITO transparent conductive film is attached to glass or transparent plastic substrate 40 by sputtering or evaporation; cathode 20 is a metal electrode containing magnesium (Mg), lithium (Li), aluminum (A1), etc .; The EL element 30 includes a hole injection layer (11016-: [114 | 6 (: 1; 丨 〇1181)]: 301, a hole-transport layer 302, and light emission. Layers (light emitting layer) 303, and electron-transport layer 304 and other multilayer structures of organic electroluminescent elements (EL elements), which constitute a light emitting layer in an organic electroluminescence device structure (light emitting layer, EML). "9, 10- (diphenyl) anthracene)" is a kind of blue fluorescence materials with high fluorescence efficiency, but there will be more Crystallization (recrystallization) phenomenon. Correct the molecular structure of optical materials, synthesize an asymmetric molecular structure, and add a steric-hindrance substitute group to it to reduce its recrystallization condition, and obtain a high efficiency, low driving voltage, A new blue fluorescent material that is easy to synthesize, and then uses this new blue fluorescent material to make a blue EL element with good luminous efficiency. The EL element disclosed in the present invention is used to constitute an organic electroluminescence. A light emitting layer (EML) in a light emitting device includes a substance represented by the following formula (1):

第12頁 555831 五、發明說明(6)Page 12 555831 V. Description of the invention (6)

ηn

式⑴ 其中m, η二1-3,取代基R係為相同或不同且選自於包 含有第三丁基(t-butyl)、苯基(phenyl)、甲基苯基 (methylphenyl)、萘基(naphenyl)、以及雜環族化合物 (heterocyclic bompound)的群族 〇 在本發明另一較佳實施例的E L元件,更包括由下式 (2 )所代表的一種物質:Formula ⑴ wherein m, η di 1-3, and the substituent R are the same or different and are selected from the group consisting of t-butyl, phenyl, methylphenyl, and naphthalene The naphenyl group and the heterocyclic bompound group. In another preferred embodiment of the present invention, the EL element further includes a substance represented by the following formula (2):

第13頁 555831Page 13 555831

式(2 ) 其中m, n=l-3,取代基R係為相同或不同且、琴 含有甲基(methyl)、異丙基(isopropyl)、第:r 丁自於包 (t-butyl)、苯基(phenyl)、萘基(naphenyl)、以基 族化合物(heterocyclic bompound)的群族。 及雜環 以下則是合成本發明所揭露之藍色螢光材料化人 的操作實施例: ΰ物 <合成例一 > 化合物(A ) 9-(4-第三丁基-4’ -聯苯)蒽 (9-(4’ -t-butylbiphenyl)anthracene)之合成 (a)合成4-弟二丁基-4’ -苯漠化鎮 (4-tert-4’ -biphenylmagnesiumbromide) 8 · 4克4 -第三丁基-4 -臭-聯苯 (4-bromo-4’ - tert-butyl-biphenyl)及1 克鎭 (magnesium)置於150毫升反應瓶中,加入20毫升四氫呋 喃(tetraphdrofurane),加熱80度攪拌並反應四小時。Formula (2) wherein m, n = 1 to 3, the substituents R are the same or different, and the methyl group contains methyl, isopropyl, and th: t-butyl , Phenyl (naphthyl), naphthyl (naphenyl), and a group of heterocyclic bompounds. The following are examples of the operation of synthesizing the blue fluorescent material disclosed in the present invention with the following heterocycles: ΰ 物 < Synthesis Example 1 > Compound (A) 9- (4-third butyl-4 '- Synthesis of biphenyl) anthracene (9- (4'-t-butylbiphenyl) anthracene) (a) Synthesis of 4-tert-4'-biphenylmagnesiumbromide 8 · 4 Grams of 4-bromo-4'-tert-butyl-biphenyl and 1 g of magnesium are placed in a 150 ml reaction bottle, and 20 ml of tetraphdrofurane are added. , Heated at 80 degrees, stirred and reacted for four hours.

^55831^ 55831

(b)5 〜、白 3〜-2 〉昊化爹(9-bromo anthracene)、〇.13 克 1, 瓶,加入5〇,燒〜二氣鎳(NiC12(dppp))置於250毫升反應 將(a )溶、、毫升四氫呋喃,加熱6 〇度反應一小時,慢慢 抽乾,液滴入,攪拌並反應8小時。將溶液以減壓蒸餾 及甲醇ϋ1曰〇〇毫升甲醇洗三次,過濾溶液,固體用甲苯 式表結晶’得5· 0克淡黃色固體,產率68%。其結構 如下式(3 )。(b) 5 ~, white 3 ~ -2> 9-bromo anthracene, 0.13 g 1, bottle, add 50, burn ~ digas nickel (NiC12 (dppp)) and put in 250 ml reaction Dissolve (a), tetrahydrofuran in milliliters, and heat at 60 ° C for one hour, and then slowly dry it out, drip the solution, stir and react for 8 hours. The solution was distilled under reduced pressure and washed three times with 100 ml of methanol, and the solution was filtered. The solid was crystallized from toluene to obtain 5.0 g of a pale yellow solid with a yield of 68%. Its structure is as follows (3).

式(3 ) <合成例二> 化合物(Β)9,-(4-(2,4,6 -三曱基笨基)一卜苯基)蒽 (9-4-(2, 4, 6-Trimethylphenyi) —卜phenyl)anthracene 之合成Formula (3) < Synthesis Example 2 > Compound (B) 9,-(4- (2,4,6-trimethylphenylbenzyl) phenylphenyl) anthracene (9-4- (2, 4, 6-Trimethylphenyi) — Synthesis of phenyl) anthracene

第15頁 555831 五、發明說明(9) (a) 合成4-1,3,5 -三甲基苯基-1-苯漠化鎂 (4-1,3,5-trimethylphenyl-1-benzenemagnesiumbromid e ) 7· 8克4-1,3, 5 -三甲基苯基-1-溴化苯 (4-1, 3, 5-trimethylphenyl-l-benzylbromide)及1 克鎂 (magnesium)置於150毫升反應瓶中,加入20毫升四氫口夫 喃(tetrahydrofurane),加熱80度攪拌並反應四小時。 (b) 5 克9一溴化蒽(9-bromo anthracene) 、 0.13 克 j 3-二苯基磷丙烷-二氣鎳(NiC12(dppp))置於250毫升反應 瓶,加入5 0宅升四氫吱喃’加熱6 0度反應一小時’慢慢 將(a )溶液滴入,攪拌並反應8小時。將溶液以減壓蒸餚 抽乾,加入1 〇 〇毫升曱醇洗三次,過濾溶液,固體用甲笨 及曱醇再結晶,得4 · 2克淡黃色固體,產率6 0 %。其結構 式表示如下式(4)。Page 15 555831 V. Description of the invention (9) (a) Synthesis of 4-1,3,5-trimethylphenyl-1-benzenemagnesium bromid e 7.8 g of 4-1,3,5-trimethylphenyl-1-bromobenzene (4-1,3,5-trimethylphenyl-l-benzylbromide) and 1 g of magnesium in 150 ml To the reaction flask, 20 ml of tetrahydrofurane was added, and the mixture was heated and stirred at 80 ° C for 4 hours. (b) 5 grams of 9-bromo anthracene and 0.13 grams of j 3-diphenylphosphine-nickel (NiC12 (dppp)) are placed in a 250 ml reaction bottle, and 50 liters of quart Hydrogen squeaking 'heated at 60 degrees for one hour' and slowly dropped (a) the solution, stirred and reacted for 8 hours. The solution was evaporated to dryness under reduced pressure, and 100 ml of methanol was added and washed three times. The solution was filtered, and the solid was recrystallized from methylbenzyl and methanol to obtain 4.2 g of a pale yellow solid with a yield of 60%. Its structural formula is expressed by the following formula (4).

化合物(B) 式(4)Compound (B) Formula (4)

第16頁 55583lPage 16 55583l

合成例三> 化合物(C ) 9,- ( 3,5 -二苯基苯基)蒽 (3, 5-diphenyl)phenyl)anthracene)之合成 (a) 合成(3, 5_二苯基)苯溴化鎂 (3,5~~diphenylbenzylmagnesium bromide) 8· 8克(3, 5-二苯基)溴化苯 (3, 5-diphenylbenzylbromide)及 1· 1 克鎂(magnesium)置 於150毫升反應瓶中,加入20毫升四氫口夫喃 (tetrahydrofurane),擾拌並反應四小時〇 (b) 5 克9 -溴化蒽(9-Dirromo anthracene)、0.13 克 1,3 -二苯基填丙烧-二氯鎳(NiC12(dppp))置於250毫升反 應瓶,加入5 0毫升四氫呋喃,加熱6 0度反應一小時,慢 慢將(a)溶液滴入,攪拌並反應8小時,將溶液以減壓蒸 餾抽乾,加入1 0 0毫升甲醇洗三次,過濾溶液,固體用甲 苯及甲醇再結晶,得4· 8克淡黃色固體,產率63%。其結 構式表示如下式(5)。Synthesis Example III> Synthesis of Compound (C) 9,-(3,5-diphenylphenyl) anthracene (3,5-diphenyl) phenyl) anthracene) (a) Synthesis of (3, 5-diphenyl) 3.8g of diphenylbenzylmagnesium bromide 8.8g of (3, 5-diphenyl) benzene bromide (3, 5-diphenylbenzylbromide) and 1.1g of magnesium (magnesium) were placed in 150ml reaction Add 20 ml of tetrahydrofurane to the bottle, stir and react for 4 hours. (B) 5 g of 9-Dirromo anthracene, 0.13 g of 1,3-diphenylpropane Burned-nickel dichloride (NiC12 (dppp)) was placed in a 250 ml reaction flask, 50 ml of tetrahydrofuran was added, and the reaction was heated at 60 degrees for one hour. The solution (a) was slowly dropped in, stirred and reacted for 8 hours. It was evaporated to dryness under reduced pressure, washed with 100 ml of methanol three times, and the solution was filtered. The solid was recrystallized from toluene and methanol to obtain 4.8 g of a pale yellow solid with a yield of 63%. Its structure is represented by the following formula (5).

第17頁 555831 五、發明說明(π)Page 17 555831 V. Description of the invention (π)

化合物(C) 式(5) <合成例四> 化合物(D)合成9-(4-第三丁基苯基)-蒽 〜(4-t-butylphenyl)anthracene) (a) 合成4-第三丁基苯基溴化鎂 t〜butylbenzylmagnesium bromide) 1 克4-第三 丁基漠化苯(4-t-butylbenzylbromide)及 1· ^克鎂(magnesium)置於150毫升反應瓶中,力入20毫升四 氣咳喃(tetrahydrofurane),授拌並反應四小時。 (b) 5 克9-溴化口夫(9-Dibromo anthracene) 、 0.13 克 ^3、二苯基磷丙烷—二氯鎳(NiC12(dppp))置於250毫升反 應瓶,加入5 0毫升四氫咬喃,加熱6 0度反應一小時,慢 &將(a)溶液滴入,攪拌並反應8小時。將溶液以減壓蒸Compound (C) Formula (5) < Synthesis Example 4 > Compound (D) Synthesis of 9- (4-third-butylphenyl) -anthracene ~ (4-t-butylphenyl) anthracene) (a) Synthesis of 4- T ~ butylbenzylmagnesium bromide) 1 g 4-t-butylbenzyzylbromide and 1 · ^ g magnesium in a 150 ml reaction bottle, force 20 ml of tetrahydrofurane was added, mixed and reacted for four hours. (b) 5 grams of 9-Dibromo anthracene, 0.13 grams ^ 3, diphenylphosphine-nickel dichloride (NiC12 (dppp)) are placed in a 250 ml reaction bottle, 50 ml of four Hydrogen bite, heated at 60 ° C for one hour, and slowly (a) the solution was added dropwise, stirred and reacted for 8 hours. The solution was evaporated under reduced pressure

第18頁 555831Page 18 555831

五、發明說明(12) 餾抽乾,加入1 0 0毫升曱醇洗三次,過濾溶液,固 苯及甲醇再結晶,得4 · 1克淡黃色固體,產率7 5 %。 構式表示如下式(6 )。 ° ° #V. Description of the invention (12) Distilled and dried, 100 ml of methanol was added and washed three times, the solution was filtered, benzene and methanol were recrystallized to obtain 4.1 g of a pale yellow solid with a yield of 75%. The structural formula is expressed by the following formula (6). ° ° #

化合物(D) 式(6) <比較合成例一 > 係為已知化合物(E ) 9 -(聯苯)蒽 (9-(biphenyl)anthracene)之合成 (a )合成4 -聯苯溴化鎂(4 -biphenylmagnesiumbromide) 6· 6 克 4-溴-聯苯(4 - bromo-biphenyl)及 1 克鎂 (magnesium)置於150毫升反應瓶中,加入2〇毫升四氫吱 喃(tetrahydrofurane),加熱80度授拌並反應四小時。 (b)5 克9 -溴化蒽(9-Dibromo anthracene)、0.13 克 1,3-二苯基磷丙烷-二氯鎳(NiC12(dppp))置於250毫升反 應瓶,加入5 0毫升四氫呋喃,加熱6 0度反應一小時,慢Compound (D) Formula (6) < Comparative Synthesis Example 1 > is a synthesis of a known compound (E) 9- (biphenyl) anthracene (9- (biphenyl) anthracene) (a) Synthesis of 4-biphenyl bromide 4-biphenylmagnesiumbromide 6.6 g 4-bromo-biphenyl and 1 g magnesium were placed in a 150 ml reaction flask, and 20 ml tetrahydrofurane was added. , Heated at 80 degrees to stir and react for four hours. (b) 5 grams of 9-Dibromo anthracene, 0.13 grams of 1,3-diphenylphosphopropane-dichloronickel (NiC12 (dppp)) were placed in a 250 ml reaction flask, and 50 ml of tetrahydrofuran was added. , Heating at 60 degrees for one hour, slow

第19頁 555831 五、發明說明(13) 慢將(a )溶液滴入,攪拌並反應8小時。將溶液以減壓蒸 餾抽乾,加入1 0 0毫升甲醇洗三次,過濾溶液,固體用甲 苯及甲醇再結晶,得4 . 3克淡黃色固體,產率6 8 %。其結 構式表示如下式(7 )。Page 19 555831 V. Description of the invention (13) Slowly drip (a) the solution, stir and react for 8 hours. The solution was evaporated to dryness under reduced pressure, 100 ml of methanol was added and washed three times, and the solution was filtered. The solid was recrystallized from toluene and methanol to obtain 4.3 g of a pale yellow solid with a yield of 68%. Its structure is represented by the following formula (7).

化合物(E ) 式⑺ <比較合成例二> 係為已知化合物(F ) 9,1 0 -二(3 -甲基苯基)蒽 (9, 10-di-(3-methylphenyl)anthracene)之合成 (a )合成3 -甲基苯基溴化鎂 (3-methylphenylmagnesiumbromide) 6. 4 克 3— 甲基溴 4匕苯(3 — methylphenylbromide)及 1 克鎮 (magnesium)置於150毫升反應瓶中,加入20毫升四氫口夫 喃(tetrahydrofurane),加熱80度撲:拌並反應四小時。 (1})5克9,10二溴化蒽(9,10-(111)1'〇111〇 anthracene)、0.13克1,3 -二苯基填丙烧-二氣鎳Compound (E) Formula ⑺ < Comparative Synthesis Example 2 > is a known compound (F) 9,10-di (3-methylphenyl) anthracene (9, 10-di- (3-methylphenyl) anthracene ) Synthesis (a) Synthesis of 3-methylphenylmagnesium bromide 6. 4 g of 3-methylphenylbromide and 1 g of magnesium were placed in 150 ml reaction Add 20 ml of tetrahydrofurane to the bottle and heat it at 80 ° C: mix and react for four hours. (1)) 5 grams of 9,10 dibromoanthracene (9,10- (111) 1′〇111〇 anthracene), 0.13 grams of 1,3-diphenylpropane-digas nickel

第20頁 555831 五 '發明說明(14) (NlCl2(dppp))置於250毫升反應瓶,加入50毫升四氫萘 "南,加熱6 0度反應一小時,慢慢將(a )溶液滴入,攪拌並 反應8小時。將溶液以減壓蒸餾抽乾,加入1 〇 〇毫升甲醇 洗三次,過濾溶液,固體用甲苯及甲醇再結晶,得3 · 8克 淡黃色固體,產率7 1 %。其結構式表示如下式(8 )。Page 20 555831 Description of the Five 'Invention (14) (NlCl2 (dppp)) was placed in a 250 ml reaction flask, 50 ml of tetrahydronaphthalene was added, and the reaction was heated at 60 degrees for one hour, and the (a) solution was slowly dropped. Into, stir and react for 8 hours. The solution was distilled to dryness under reduced pressure, and 100 ml of methanol was added and washed three times. The solution was filtered, and the solid was recrystallized from toluene and methanol to obtain 3.8 g of a pale yellow solid with a yield of 71%. Its structural formula is expressed by the following formula (8).

化合物(F ) 式(8) 以下係為將本發明所合成之化合物應用於製備有機 電致發光裝置的操作實施例,以下所舉之有機電致發光 裝置均以包含有:電洞注入層(hole-injection layer),電洞傳遞層(hole-transport layer),發光層 (light emitting layer),以及電子傳遞層 (electron-transport layer)等多層結構的有機電致元 件(E L e 1 e m e n t)為例。 <製備例一 > 包含下列步驟:Compound (F) Formula (8) The following is an operation example of applying the compound synthesized by the present invention to the preparation of an organic electroluminescence device. The organic electroluminescence devices listed below all include: a hole injection layer ( hole-injection layer), hole-transport layer, light emitting layer, and electron-transport layer example. < Preparation example 1 > includes the following steps:

第21頁 555831 五、發明說明(15) (a) 選用氧化銦錫(indium-tin-oxide)玻璃(ITO玻璃)為 陽 極基板,先以市售玻璃清洗劑清洗,再用去離子水清 洗,烘乾。 (b) 選用c〇PPer Phthalcoyanine 當作電洞注入層材料 (150angstroms),蒸鐘在 IT0 玻璃上。 (c) 在電洞注入層上蒸鑛電洞傳遞層(hole-transport layer)材料-氮,氮-二-(1-萘基)-氮,氮二聯苯(N, Ν’ -bis-(Ι-naphthyl)-Ν,Ν’ - diphenylbenzidine ) ( 6 0 0 angstroms) o (d) 於電洞傳遞層上再蒸鍍發光層(light-emitting layer) 選用前述的化合物-A(150 angstroms)。 (e) 於發光層上蒸鑛電子傳遞層(electron-transport layer),三-8-氫氧基奎林鋁錯化合物(350 angstroms)(alumium-tris-8-hydroxy-quinoline) · (f )在電子傳遞層上蒸鍍鎂銀合金當作陰極。 (g)元件在充滿氮氣之乾燥手套箱中封裝。 在遥用本發明所提出的第一種化合物A,並依上述步 驟製備而成的有機電致發光裝置,經測定其E L光譜之波 長禮ax-440nm ,CIE coordinate x=y =0.17 (EL,I-V, B-V見「第5圖」),可知其波長與藍光之波長45〇nm極為 接近’而此一 E L元件的亮度/電壓曲線圖則如「第6圖」 所示,電流/電壓曲線圖則如「第7圖」所示。 <製備例二>Page 21 555831 V. Description of the invention (15) (a) Indium-tin-oxide glass (ITO glass) is used as the anode substrate, and it is cleaned with a commercially available glass cleaning agent and then with deionized water. drying. (b) Copper Phthalcoyanine was selected as the hole injection layer material (150angstroms), and the steaming bell was on IT0 glass. (c) Distilling the hole-transport layer material on the hole injection layer-nitrogen, nitrogen-di- (1-naphthyl) -nitrogen, nitrogen biphenyl (N, Ν '-bis- (Ι-naphthyl) -Ν, Ν '-diphenylbenzidine) (600 angstroms) o (d) A light-emitting layer is further vapor-deposited on the hole-transporting layer. . (e) Electron-transport layer on the light-emitting layer, 350-8 angstroms (alumium-tris-8-hydroxy-quinoline) · (f) As a cathode, a magnesium-silver alloy was vapor-deposited on the electron transport layer. (g) The device is packaged in a dry glove box filled with nitrogen. The organic electroluminescence device prepared by using the first compound A proposed by the present invention and prepared according to the above steps has been measured for an EL spectrum with a wavelength of ax-440nm and CIE coordinate x = y = 0.17 (EL, IV, BV (see "Figure 5"), it can be seen that its wavelength is very close to the wavelength of blue light of 45nm 'and the brightness / voltage curve of this EL element is shown in "Figure 6", the current / voltage curve As shown in "Figure 7". < Preparation example two >

第22頁 555831 五、發明說明(16) 包含下列步驟: (a) 選用氧化銦錫(indium-tin-oxide)玻璃(ITO玻璃)為 陽 極基板,先以市售玻璃清洗劑清洗,再用去離子水清 洗,烘乾。 (b) 選用copper phthalcoyanine當作電洞注入層材料 (150angstroms),蒸鍍在 IT0 玻璃上。 (c) 在電洞注入層上蒸鐘電洞傳遞層(hole-transport layer)材料-氮,氮—二—(1—萘基)-氮,氮二聯苯(N, N’-bis-(l-naphthyl)-N,N’-diphenylbenzidine ) (4 0 0 angstroms ) 〇 (d) 於電洞傳遞層上再蒸艘發光層(light-emitting layer) 選用前述之化合物-B(150 angstroms)。 (e) 於發光層上蒸鍵電子傳遞層(eiectron-transport layer),三-8-氫氧基奎林鋁錯化合物(300 angstroms)(alumium-tris-8-hydroxy-quinoline) 〇 (f )在電子傳遞層上蒸鍍鎂銀合金當作陰極。 (g)元件在充滿氮氣之乾燥手套箱中封裝。 <製備例三> 包含下列步驟: (a)選用氧化銦錫(indium-tin-oxide)玻璃(IT0玻璃)為 陽 極基板,先以市售玻璃清洗劑清洗,再用去離子水清 洗,烘乾。Page 22 555831 V. Description of the invention (16) Includes the following steps: (a) Select indium-tin-oxide glass (ITO glass) as the anode substrate, first clean it with a commercially available glass cleaning agent, and then use it. Wash with ion water and dry. (b) Copper phthalcoyanine was selected as the hole injection layer material (150angstroms) and evaporated on IT0 glass. (c) Steam hole-transport layer material-nitrogen, nitrogen-di- (1-naphthyl)-nitrogen, nitrogen biphenyl (N, N'-bis- (l-naphthyl) -N, N'-diphenylbenzidine) (4 0 0 angstroms) 〇 (d) Re-evaporate the light-emitting layer on the hole-transport layer. . (e) vapor-bond an electron-transport layer (eiectron-transport layer) on the light-emitting layer, and tri-8-hydroxyquinolinium aluminum compound (300 angstroms) (alumium-tris-8-hydroxy-quinoline) 〇 (f) As a cathode, a magnesium-silver alloy was vapor-deposited on the electron transport layer. (g) The device is packaged in a dry glove box filled with nitrogen. < Preparation example 3 > includes the following steps: (a) using indium-tin-oxide glass (IT0 glass) as the anode substrate, cleaning with a commercially available glass cleaning agent, and then using deionized water, drying.

第23頁 555831 五、發明說明(17) (b) copper phthalcoyanine 當作電洞注入層材料 (150angstroms),蒸鍍在 IT0 破璃上。 (c) 在電洞庄入層上条鍍電洞傳遞層(h〇ie-tranSp〇rt layer)材料-氮,氮-二—(1-萘基)—氮,氮二聯苯(N, N’-bis-(l-naphthyl)-N,N’-diphenylbenzidine) (600 angstroms) 〇 (d) 於電洞傳遞層上再蒸鑛發光層(light-emitting \ layer)選用前述化合物-C(150 angstroms)。 (e) 於發光層上蒸鍍電子傳遞層(electron-transport layer),三-8-氫氧基奎林鋁錯化合物(350 angstroms)(alumium-tris-8-hydroxy-quinoline) ° (f )在電子傳遞層上蒸鍍鎂銀合金當作陰極。 (g)元件在充滿氮氣之乾燥手套箱中封裝。 <製備例四> 包含下列步驟: (a) 選用氧化銦錫(indium-tin-oxide)玻璃(IT0玻璃)為 陽 極基板,先以市售玻璃清洗劑清洗,再用去離子水清 洗,烘乾。 (b) copper phthalcoyanine 當作電洞注入層材料 (120angstroms),蒸鍍在 IT0 玻璃上。 (c) 在電洞注入層上蒸鍍電洞傳遞層(hole —transP〇rt layer)材料-氮,氮-二-(1-萘基氮,氮二聯苯(N, N,-bis-(1-naphthyl)-N,N,_diphenylbenzidine )Page 23 555831 V. Description of the invention (17) (b) Copper phthalcoyanine is used as a hole injection layer material (150angstroms) and is vapor-deposited on IT0 glass. (c) A hole-transmission layer (h0ie-tranSprt layer) material-nitrogen, nitrogen-di- (1-naphthyl) -nitrogen, nitrogen biphenyl (N, N'-bis- (l-naphthyl) -N, N'-diphenylbenzidine) (600 angstroms) 〇 (d) Re-evaporate the light-emitting layer on the hole transfer layer (light-emitting \ layer) using the aforementioned compound -C ( 150 angstroms). (e) Electron-transport layer, 350-8 angstroms (alumium-tris-8-hydroxy-quinoline) ° (f) is deposited on the light-emitting layer. As a cathode, a magnesium-silver alloy was vapor-deposited on the electron transport layer. (g) The device is packaged in a dry glove box filled with nitrogen. < Preparation Example 4 > includes the following steps: (a) selecting indium-tin-oxide glass (IT0 glass) as the anode substrate, cleaning it with a commercially available glass cleaning agent, and then using deionized water, drying. (b) Copper phthalcoyanine is used as a hole injection layer material (120angstroms) and is deposited on IT0 glass. (c) A hole-transport layer material-nitrogen, nitrogen-di- (1-naphthyl nitrogen, nitrogen biphenyl (N, N, -bis-)- (1-naphthyl) -N, N, _diphenylbenzidine)

第24頁 555831 五、發明說明(18) ( 4 0 0 angstroms) ° (d) 於電洞傳遞層上再蒸鑛發光層(light-emitting layer) 選用前述化合物 -D(150 angstroms)。 (e) 於發光層上蒸鐘電子傳遞層(electron-transport layer),三-8-氫氧基奎林銘錯化合物(350 angstroms)(alumium-tris-8-hydroxy-quinoline) ° (f )在電子傳遞層上蒸鍍鎂銀合金當作陰極。 (g )元件在充滿氮氣之乾燥手套箱中封裝。 <製備比較例一 > 包含下列步驟:Page 24 555831 V. Description of the invention (18) (400 angstroms) ° (d) Re-steaming the light-emitting layer on the hole transfer layer Select the aforementioned compound -D (150 angstroms). (e) Electron-transport layer, 350-angstroms (alumium-tris-8-hydroxy-quinoline) ° (f) on the light-emitting layer As a cathode, a magnesium-silver alloy was vapor-deposited on the electron transport layer. (g) The device is packaged in a dry glove box filled with nitrogen. < Preparation of Comparative Example 1 > includes the following steps:

(a) 氧化銦錫(indium-tin-oxide)玻璃(IT0玻璃)為陽極 基 板,先以市售玻璃清洗劑清洗,再用去離子水清洗, 烘乾。 (b) copper phthalcoyanine 當作電洞注入層材料 (150angstroms),蒸鑛在 IT0 玻璃上。 (c) 在電洞注入層上蒸鍵電洞傳遞層(hole-transport layer)材料-氮,氮-二-(卜萘基)-氮,氮二聯苯(N, N,- bis-(l-naphthyl)-N,Ν’ -diphenylbenzidine ) ( 4 0 0 angstroms) 〇(a) Indium-tin-oxide glass (IT0 glass) is used as the anode substrate, and it is washed with a commercially available glass cleaning agent, and then washed with deionized water, and dried. (b) Copper phthalcoyanine is used as the hole injection layer material (150angstroms), and steam is mined on IT0 glass. (c) A hole-transport layer material-nitrogen, nitrogen-di- (bnaphthyl) -nitrogen, nitrogen biphenyl (N, N,-bis- (l- naphthyl) -N, N'-diphenylbenzidine) (4 0 0 angstroms) 〇

(d) 於電洞傳遞層上再蒸鑛發光層(light-emittint layer) 選用前述化合物-E(150 angstroms)。 (e) 於發光層上蒸鍵電子傳遞層(electron-transport layer),三-8-氫氧基奎林銘錯化合物(300(d) Re-steaming the light-emittint layer on the hole-transporting layer selects the aforementioned compound-E (150 angstroms). (e) An electron-transport layer was vapor-bonded on the light-emitting layer, and tri-8-hydroxyquinolin-Ming compound (300

第25頁 555831 五、發明說明(19) angstroms)(alumium-tris-8-hydroxy-quinoline) 〇 (f) 在電子傳遞層上蒸鑛鎮銀合金當作陰極。 (g) 元件在充滿氮氣之乾燥手套箱中封裝。 <製備比較例二> 包含下列步驟: (a) 氧化銦錫(indium-tin-oxide)玻璃(IT0玻璃)為陽極 基 板,先以市售玻璃清洗劑清洗,再用去離子水清洗, 烘乾。 (b) copper ph t ha 1 coy an i ne 當作電洞注入層材料 (150angstroms),蒸鍵在 ITO 玻璃上。 (c) 在電洞注入層上蒸鑛電洞傳遞層(hole-transport layer)材料-氮,氮-二-(1-萘基)-氮,氮二聯苯(N, Ν’ - bis-(l-naphthyl)-N,Ν’ - diphenylbenzidine ) (400 angstroms)。 (d) 於電洞傳遞層上再蒸鑛發光層(light-emitting layer ) 選用前述化合物-F(150 angstroms)。 (e) 於發光層上蒸鍵電子傳遞層(electron-transport layer),三-8-氫氧基奎林鋁錯化合物(300 angstroms)(alumium-tris-8-hydroxy-quinoline) 〇 (f )在電子傳遞層上蒸鍍鎂銀合金當作陰極。 (g)元件在充滿氮氣之乾燥手套箱中封裝。 最後依據上述各個製備例的結果,可以計算出選用 本發明所合成之藍色螢光材料所製成有機電致發光裝Page 25 555831 V. Description of the invention (19) angstroms) (alumium-tris-8-hydroxy-quinoline) ○ (f) Steam-mineralized silver alloy is used as the cathode on the electron transport layer. (g) The components are packaged in a dry glove box filled with nitrogen. < Preparation of Comparative Example 2 > Including the following steps: (a) Indium-tin-oxide glass (IT0 glass) as the anode substrate, first washed with a commercially available glass cleaning agent, and then washed with deionized water, drying. (b) Copper ph t ha 1 coy an i ne is used as the hole injection layer material (150angstroms), and the bond is vapor-deposited on the ITO glass. (c) Distilling the hole-transport layer material on the hole injection layer-nitrogen, nitrogen-di- (1-naphthyl) -nitrogen, nitrogen biphenyl (N, Ν '-bis- (l-naphthyl) -N, N'-diphenylbenzidine) (400 angstroms). (d) Re-evaporate the light-emitting layer on the hole transfer layer using the aforementioned compound-F (150 angstroms). (e) An electron-transport layer is vapor-bonded on the light-emitting layer. The tri-8-hydroxyquinolinium aluminum compound (300 angstroms) (alumium-tris-8-hydroxy-quinoline) is 〇 (f) As a cathode, a magnesium-silver alloy was vapor-deposited on the electron transport layer. (g) The device is packaged in a dry glove box filled with nitrogen. Finally, based on the results of the above preparation examples, an organic electroluminescent device made of the blue fluorescent material synthesized by the present invention can be calculated.

第26頁 555831 五、發明說明(20) 置,與採用已知藍色螢光材料(化合物E,F )製成的有機 電致發光裝置,其發光效率及波長之比較數據如下附表 —戶斤示0 電壓(V) 效率(lm/W)* 發光極大波長(nm) 本發明 化合物A 1 7 1. 3 440 化合物B 7 1. 2 460 化合物C 8 1. 3 450 化合物D 10 1. 1 [ 460 已知ϋ材1 化合物E 12 0. 9 」 460 化合物F 15 0.4 | 480 *測點面積:0 · 2 5 c m 2 P付表一Page 26 555831 V. Description of the invention (20) The comparison of luminous efficiency and wavelength of organic electroluminescence devices made of known blue fluorescent materials (compounds E, F) is as follows: Indication 0 Voltage (V) Efficiency (lm / W) * Maximum emission wavelength (nm) Compound A 1 7 1. 3 440 Compound B 7 1. 2 460 Compound C 8 1. 3 450 Compound D 10 1.1 [460 Known sapwood 1 Compound E 12 0. 9 ″ 460 Compound F 15 0.4 | 480 * Measuring area: 0 · 2 5 cm 2 P

第27頁 555831 圖式簡單說明 第1圖,係為有機電致發光裝置的基本構造斷面圖。 第2圖,係為有機電致發光裝置的另一種構造斷面 圖。 第3 A〜3 C圖,係為習知三種有機發光二極體的構造斷 面圖。 第4圖,係為本發明之有機電致發光裝置的構造斷面 圖。 第5圖,係為本發明之製備例一所製成之有機電致發 光裝置的波長分佈曲線圖。 第6圖,係為本發明之製備例一所製成之有機電致發 光裝置的亮度/電壓曲線圖。 第7圖,係為本發明之製備例一所製成之有機電致發 光裝置的電流/電Μ曲線圖。 【圖式符號說明】 1 · · · ·陽極 2 · · · •透明玻璃 3 · · · ·陰極 4 · · · •電子傳遞層 5 · · · ·發光層(light emitting layer) 6 · · · ·電洞傳遞層(hole transport layer) 7 ····電洞注入層(Hole Injection Layer, HIL) 0EL1, 0EL2, 0EL3 · . · ·三種發光材料 B_0EL · · · ·藍色發光材料 F1 · · · ·光色轉換薄膜Page 27 555831 Brief description of the drawings Figure 1 is a cross-sectional view of the basic structure of an organic electroluminescence device. Fig. 2 is a sectional view showing another structure of an organic electroluminescence device. Figures 3A to 3C are sectional views of the structure of three conventional organic light emitting diodes. Fig. 4 is a structural sectional view of an organic electroluminescence device of the present invention. Fig. 5 is a graph showing the wavelength distribution of an organic electroluminescent device manufactured in Preparation Example 1 of the present invention. Fig. 6 is a brightness / voltage curve of an organic electroluminescence device manufactured in Preparation Example 1 of the present invention. Fig. 7 is a current / electricity M curve of an organic electroluminescent device manufactured in Preparation Example 1 of the present invention. [Illustration of Symbols] 1 · · · · Anode 2 · · · · · Transparent glass 3 · · · · Cathode 4 · · · · · Electron transfer layer 5 · · · · Light emitting layer 6 · · · · Hole transport layer 7 ··· Hole Injection Layer (HIL) 0EL1, 0EL2, 0EL3 · · · · Three light emitting materials B_0EL · · · · Blue light emitting material F1 · · · · Light color conversion film

第28頁 555831 圖式簡單說明 W_OEL · · · ·白色發光材料 F2 • • · •彩色 濾、 光 膜 1 0 • · • •陽 極 2 0 • · • •陰 極 3 0 • · • •有 機 電 致 元 件(EL el ement) 4 0 • · • •玻 璃 或 是 透 明的塑膠 基板 3 0 1 · • · · 電 洞 注 入 層(h 〇 1 e - injection layer) 3 0 2 · • · · 電 洞 傳 遞 層(h 〇 1 e - transport layer) 3 0 3 · • · · 發 光 層(1 i gh t em i 11 i ng layer) 3 0 4 · • · · 電 子 傳 遞 層(e 1 e c t ron-transport layer)Page 28 555831 Brief description of drawings W_OEL · · · · White luminescent material F2 (EL el ement) 4 0 • • • • Glass or transparent plastic substrate 3 0 1 • • • • Hole injection layer (h 〇1 e-injection layer) 3 0 2 • • • Hole transfer layer ( h 〇1 e-transport layer) 3 0 3

第29頁Page 29

Claims (1)

555831 六、申請專利範圍 公告本 1 一種有機電致發光裝置(EL device),其包括有一陽 極、一陰極以及一包夾於其間用以發光的有機電致 元件(EL element),該有機電致元件係包括由下式 所代表的一種物質:555831 VI. Announcement of the scope of patent application 1 An organic electroluminescence device (EL device) comprising an anode, a cathode, and an organic element (EL element) sandwiched therebetween for emitting light, the organic electroluminescence The element system includes a substance represented by: 其中m, n=l-3,取代基R係為相同或不同且選自於包 含有第三丁基(t-butyl)、苯基(phenyl)、甲基苯基 (methylphenyl )、以及萘基(naphenyl)的群族。 如申請專利範圍第1項所述的有機電致發光裝置, 其中該取代基R係為第三丁基(t-butyl)。 3 一種有機電致發光裝置(EL device),其包括有一陽 極、一陰極以及一包夾於其間用以發光的有機電致 元件(E L e 1 e m e n t),該有機電致元件係包括由下式 所代表的一種物質:Where m, n = 1 to 3, and the substituents R are the same or different and are selected from the group consisting of t-butyl, phenyl, methylphenyl, and naphthyl (Naphenyl) group. The organic electroluminescence device according to item 1 of the scope of patent application, wherein the substituent R is a third butyl (t-butyl). 3 An organic electroluminescence device (EL device) comprising an anode, a cathode, and an organic electroluminescent element (EL e 1 ement) sandwiched therebetween for emitting light. The organic electroluminescent element includes the following formula A substance represented: 第30頁 555831 六、申請專利範圍Page 30 555831 6. Scope of patent application 其中m, n=l-3,取代基R係為相同或不同且選自於包 含有甲基(methyl)、異丙基(isopropyl)、第三丁基 (t-butyl)、苯基(phenyl)以及萘基(η8ρ1ΐ6η7ΐ)的群 族0 4 如申請專利範圍第3項所述的有機電致發光裝置, 其中該取代基R係為第三丁基(t-butyl )。 & 於 如申請專利範圍第3項所述的有機電致發光裝置 其中m=l, n=l-3,取代基R係為相同或不同且琴 包含有第三丁基(t-butyl)、苯基(Phenyl)、、自 基(methylphenyl)、萘基(naphenyl)、以 甲基笨 化合物(heterocyclic bompound)的群族 0 如申請專利範圍第5項所述的有機電致發光 其中該取代基R係為第三丁基(t-buty 1 )。 &置Where m, n = 1 to 3, the substituents R are the same or different and are selected from the group consisting of methyl, isopropyl, t-butyl, and phenyl ) And naphthyl (η8ρ1ΐ6η7ΐ) group 0 4 The organic electroluminescence device as described in item 3 of the patent application scope, wherein the substituent R is a third butyl (t-butyl). & In the organic electroluminescence device as described in item 3 of the scope of patent application, wherein m = 1, n = l-3, the substituents R are the same or different and the t-butyl group contains t-butyl , Phenyl, methylphenyl, naphenyl, heterocyclic bompound group 0 Organic electroluminescence as described in item 5 of the scope of patent application wherein the substitution The radical R is a third butyl (t-buty 1). & 第31頁Page 31
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI575795B (en) * 2014-02-18 2017-03-21 財團法人工業技術研究院 Blue light emitting element and light emitting element

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI575795B (en) * 2014-02-18 2017-03-21 財團法人工業技術研究院 Blue light emitting element and light emitting element

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