TWI379884B - - Google Patents

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TWI379884B
TWI379884B TW096145860A TW96145860A TWI379884B TW I379884 B TWI379884 B TW I379884B TW 096145860 A TW096145860 A TW 096145860A TW 96145860 A TW96145860 A TW 96145860A TW I379884 B TWI379884 B TW I379884B
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layer
light
fluorescent
dopant
organic
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TW096145860A
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TW200925239A (en
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Tetrahedron Technology Corp
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • C07C15/56Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed
    • C07C15/58Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed containing two rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • C07C15/56Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed
    • C07C15/60Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed containing three rings
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • H10K50/10OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14Carrier transporting layers
    • H10K50/15Hole transporting layers
    • H10K50/156Hole transporting layers comprising a multilayered structure
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • H10K50/10OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17Carrier injection layers
    • H10K50/171Electron injection layers
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60Organic compounds having low molecular weight
    • H10K85/615Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10Non-macromolecular compounds
    • C09K2211/1003Carbocyclic compounds
    • C09K2211/1011Condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

九、發明說明: 【發明所屬之技術領域】 本發明係關於—種螢光主發光體材料,更進一步地, X關於一種使用前述螢光主發光體材料之高發光效 ,長壽命之有機電激發光裝置。 【先前技術】 1 β近來有機半導體與有機導電材料的被熱烈地研究,尤 ^ =使用有機半導體之發光元件之有機電冷光裝置已具有 頁者地進步。有機電激發光(organic electroluminescence, 0EL)是指在一定電場下,有機物質被相應的電能激發所發 生的發光現象。1963年p0pei等人在研究 10〜20"111厚的 ® (anthracene)單晶片時首先發現在晶體兩端施以4〇〇伏特 電壓後’可觀察到蔥發出藍色螢光,使得有機電激發光的 研究跨出了第一步,但由於單晶成長、大面積化困難,且 所需的驅動電壓太大,發光效率又較無機材料差,因此不 具實用價值。隨後Helfrich和Williams等人繼續努力研究, 將電壓降至100伏特左右,獲得了約5 %光子/電子的外部 里子效率’但由於卓晶厚度還是過大’因而使得驅動電壓 也較高,造成電能轉化成光能的效率太低。1982年Vincett 等人利用真空蒸渡法製成了僅50 nm厚的蔥薄膜,進一步 將驅動電屋降至30伏特即能觀察到藍色螢光,不過由於電 子注入效率太低及蔥的成膜性不好,所以其外部量子效率 只有0.03 %左右。之後雖經過二十多年的零星發展,卻仍 一直未有重大突破。 直到1987年美國柯達公司(Eastman Kodak company)IX. Description of the Invention: [Technical Field of the Invention] The present invention relates to a fluorescent main illuminant material, and further, X relates to a high luminous efficiency, long-life organic electric power using the aforementioned fluorescent main illuminant material. Excitation light device. [Prior Art] 1 Recently, organic semiconductors and organic conductive materials have been studied enthusiastically, and in particular, organic light-cooling devices using light-emitting elements of organic semiconductors have progressed. Organic electroluminescence (0EL) is a phenomenon in which an organic substance is excited by a corresponding electric energy under a certain electric field. In 1963, p0pei et al. first studied the 10~20"111 thick® (anthracene) single wafer and first found that after applying 4 volts of voltage across the crystal, 'onion can be observed to emit blue fluorescence, so that the organic electricity is excited. The research of light has taken the first step. However, due to the difficulty in growing single crystals and large area, and the required driving voltage is too large, the luminous efficiency is inferior to that of inorganic materials, so it has no practical value. Subsequently, Helfrich and Williams and others continued their efforts to reduce the voltage to about 100 volts, and obtained an external neutron efficiency of about 5% photon/electron 'but because the thickness of the crystal is too large', the driving voltage is also high, resulting in electrical energy conversion. The efficiency of light energy is too low. In 1982, Vincett et al. used a vacuum evaporation method to make a 50 nm thick onion film. Further, when the drive house was lowered to 30 volts, blue fluorescence was observed, but the electron injection efficiency was too low and the onion was formed. The film properties are not good, so its external quantum efficiency is only about 0.03%. After more than 20 years of sporadic development, there have been no major breakthroughs. Until 1987, the Eastman Kodak company

Tang及VanSlyke等人首先發表有機發光二極體(organie 1379884 light-emitting diodes,OLEDs),才有突破性的發展。他們將 芳香二胺(HTM-2)作為電洞傳輸層材料,和成膜性好的8_ 羥基喹琳鋁 A1q3 (tris(8-hydr〇xyquinolinato)alumimim(III)) ,作為電子傳輸層和發光材料利用真空蒸鍍製成60〜70 nm的 薄膜,並以低功函數的鎂銀合金為陰極,提高電子和電洞 的注入效率。在兩片電極間置入其所開發的有機小分子發 光材料,通電即可發出光來,其產生波長為53〇nm的綠光, 可展現出低驅動電壓、高量子效率(> 1 %)及元件穩定性等 φ 效果,大幅提升有機小分子電激發光元件的特性與實用性。 其後1990年’英國劍橋大學(cambridge University) Friend等人接著發表高分子發光二極體(p〇lymer light-emitting diodes,PLEDs) ’以旋轉塗佈的方式,將共軛 南分子 PPV (poly(p-phenylene vinylene))當作發光層,製作 出早層結構的聚合物電激發光元件,由於其具有製程簡 單、高分子良好的機械性質及似半導體的特性,使得共輛 高分子發光材料方面的研究快速發展。 值得注意的是’比起目前以LCD為主流的FPD,〇LED 鲁 不但能自發光,不需要背光模組,且具有低驅動電壓、高 亮度、高對比、廣視角、響應速度快、結構簡單、超薄膜、 重量輕等優點’可有效應用於照明或製成顯示器、光電偶 • 合器等地方,若製作在如塑膠基板的柔軟襯底上,器件便 可彎曲、折疊便於攜帶’而且由於製程簡單,預計可大幅 • 降低成本。目前已吸引全球超過八十家公司競相投入巨資 研發有機電激發光顯示器技術,也因而成為另一顯示技術 的主流。 乂1997年,日本Pioneer公司首先發表一款低分子系的單 色(綠色)被動式顯示器’成功地將有機電激發光顯示技 1379884 術,實用地應用在汽車儀器面板上。此後有機電激發光顯 示器開始產品化,陸續被應用在小尺寸的面板上,像1998 . 年日本TDK公司,2002年鍊寶科技,三星,NTT Do Co Mo . 的彩色手機,2003年柯達數位相機等。曰本Pioneer公司與 柯達Kodak也合作小量量產〇LED單色及多色(monochrome 时d multicolor)的顯示器,目前已正式應用在Motorola手機 上’頗獲好評;而Sanyo亦與柯達合作,製作出小尺寸的 全彩(full color) OLED樣品,宣稱於2〇〇1年後量產;奇美 • 公司更發表了主動式的10吋以上的彩色顯示器,使得有機 電激發光技術更跨進一步。不過,至目前為止,OLED仍有 其須進一步改善之處,包括其色飽和度、穩定度、發光效 率和壽命等等,此與材料本身的性質和製程息息相關,若 能突破應能期許成為未來顯示器的趨勢》 發光材料在有機電激發光元件中是最重要的材料,好 的發光材料必需滿足四個條件:(1)高量子效率的螢光特 性’且螢光光譜主要分佈在400〜700 nm可見光區域内;(2) 良好的半導體特性,具有高的導電率,能傳導電子或電洞, # 或者兩者皆有;P)良好的成膜性,在幾十奈米的薄膜中不 會產生針孔;(4)良好的熱穩定性。 、 大部份的電子傳輸層和電洞傳輸層都可作為可見光區 的發光材料,由於大多數的有機材料在超過一定濃度,尤 其是固態時,會存在自我驟媳、(selfquenching)或稱濃度驟熄、 (concentration quenching)的問零’導致發射峰變寬或是產生 紅位移,所以一般會以低濃度的方式將螢光摻雜物掺雜 (doping)在具某種載流子性質的螢光主發光體材料(h〇st)中 作為客發光體(dopant emitter)。應用在有機電激發光元件的 螢光主發光體材料與螢光摻雜物之幾個設計考慮為:(丨)榮 7 1379884 光摻雜物具有高的螢光效率;(2)螢光摻雜物的吸收光譜和 螢光主發光體材料的發射光譜要有很好的重疊,使能量可 以有效地從主體傳遞到客體;(3)有紅、藍、綠或黃色的發 射峰,且發射峰盡可能的窄以維持光色的純度;(4)穩定性 好,能蒸鍍。 近幾年業界致力於有機電激發光材料的研究,已經有 了不錯的成果。紅、藍、綠是光的三原色,好的三原色效 率及純色是達到全彩顯示器的基本重要需求。在日本出光 興產之特開2001-335516之專利公開案中,揭示了一種有機 電激發光元件,其發光層之螢光主發光體材料結構係如下 式:Tang and VanSlyke et al. first published organic light-emitting diodes (organie 1379884 light-emitting diodes, OLEDs), which was a breakthrough development. They used aromatic diamine (HTM-2) as a hole transport layer material, and a good film-forming property of 8_hydroxyquinoline A1q3 (tris(8-hydr〇xyquinolinato)alumimim(III)) as an electron transport layer and luminescence. The material is vacuum-deposited to form a film of 60 to 70 nm, and a low work function magnesium-silver alloy is used as a cathode to improve the injection efficiency of electrons and holes. The organic small molecule luminescent material developed by the two electrodes is placed, and the light is emitted when it is energized, which generates green light with a wavelength of 53 〇nm, which can exhibit low driving voltage and high quantum efficiency (> 1%) ) and the φ effect of component stability, which greatly enhances the characteristics and practicability of organic small molecule electroluminescent devices. Then in 1990, 'Cambridge University' Friend et al. subsequently published p〇lymer light-emitting diodes (PLEDs)' to spin-coat the conjugated southern molecule PPV (poly (p-phenylene vinylene)) as a light-emitting layer, a polymer electroluminescent device having an early layer structure, which has a simple process, good polymer properties and semiconductor-like properties, so that a total of polymer light-emitting materials Research in the field has developed rapidly. It is worth noting that compared to the current FPD with LCD as the mainstream, 〇LED Lu not only self-illuminates, does not require a backlight module, and has low driving voltage, high brightness, high contrast, wide viewing angle, fast response, and simple structure. , ultra-thin film, light weight and other advantages can be effectively applied to lighting or made into displays, photocouples, connectors, etc. If fabricated on a flexible substrate such as a plastic substrate, the device can be bent and folded for easy carrying. The process is simple and is expected to significantly reduce costs. At present, more than 80 companies around the world have been attracted to invest heavily in the development of organic electroluminescent display technology, which has become the mainstream of another display technology.乂In 1997, Pioneer of Japan first published a low-molecular monochromatic (green) passive display, which successfully applied organic electroluminescence display technology 1379884, and applied it practically on automotive instrument panels. Since then, organic electroluminescent display has begun to be commercialized and has been applied to small-sized panels, such as the 1998 TDK Corporation, 2002 Sparks Technology, Samsung, NTT Do Co Mo. Color Phone, 2003 Kodak Digital Camera Wait. Sakamoto Pioneer and Kodak Kodak also cooperated with a small amount of LED monochromatic and multi-color (monochrome d multicolor) display, which has been officially applied to Motorola mobile phones, 'very well received; and Sanyo also cooperated with Kodak to make A small-size full-color OLED sample is claimed to be mass-produced in 2001. CMI has also released an active color display of more than 10 inches, making organic electro-optic technology even more advanced. However, until now, OLEDs still have further improvements, including their color saturation, stability, luminous efficiency and longevity. This is closely related to the nature and process of the material itself. If it can break through, it should be expected to become the future. Trends in displays>> Luminescent materials are the most important materials in organic electroluminescent devices. Good luminescent materials must meet four conditions: (1) high quantum efficiency fluorescence characteristics' and the fluorescence spectrum is mainly distributed between 400 and 700. In the visible region of nm; (2) good semiconductor properties, high conductivity, ability to conduct electrons or holes, # or both; P) good film formation, not in tens of nanometers of film Pinholes will be produced; (4) Good thermal stability. Most of the electron transport layer and the hole transport layer can be used as luminescent materials in the visible light region. Since most organic materials exceed a certain concentration, especially in the solid state, there will be self-quenching or concentration. The zero quenching of the concentration quenching results in a broadening of the emission peak or a red shift, so the fluorescent dopant is generally doped in a low concentration manner with certain carrier properties. In the fluorescent main illuminant material (h〇st), it is used as a dopant emitter. Several design considerations for fluorescent primary illuminant materials and fluorescent dopants for organic electroluminescent devices are: (丨) Rong 7 1379884 Light dopants have high fluorescence efficiency; (2) Fluorescence blending The absorption spectrum of the impurity and the emission spectrum of the fluorescent main emitter material should be well overlapped so that the energy can be efficiently transmitted from the host to the guest; (3) there are red, blue, green or yellow emission peaks, and the emission The peak is as narrow as possible to maintain the purity of the light color; (4) the stability is good and can be evaporated. In recent years, the industry has devoted itself to the research of organic electroluminescent materials, and has already achieved good results. Red, blue and green are the three primary colors of light. Good three primary color efficiencies and solid colors are the basic important requirements for achieving full color displays. In the patent publication of Japanese Laid-Open Patent Publication No. 2001-335516, an organic electroluminescent device is disclosed. The structure of the fluorescent main emitter material of the light-emitting layer is as follows:

柯達公司之美國專利編號US-2005089717揭示了一種 有機電激發光元件,其發光層之螢光主發光體材料結構係 如下: 8 1379884An organic electroluminescent device is disclosed in U.S. Patent No. US-A-0,050, 897, 017 to Kodak Corporation, the luminescent element of which has a fluorescent luminescent material structure as follows: 8 1379884

不同 然此專利之發明物與本案 之結構式不同,光電特性亦 此夕卜’ LovionDifferent from the invention of this patent, the photoelectric characteristics are also different. Lovion

螢光波長較短之深。=專利EP1655359揭示了-種 雜物搭配使用時,可有%& θ發光體材料,當其與螢光摻 命。然而,此專利所請以;光摻雜物之發光效率與壽 其異構物的分離純化誠以有-,缺點,亦即該材料與 有較短之螢光光譜性質。 u其巾—個異構物才具The wavelength of the fluorescent wavelength is shorter. = Patent EP 1 655 359 discloses that when used in combination with a hybrid, there may be a % & θ illuminant material when it is blended with fluorescent light. However, this patent requires that the light-emitting efficiency of the photo-dopant and the separation and purification of its isomers have a drawback, that is, the material has a shorter spectral property. u its towel - an isomer

針對先前技術的缺點, 主發光體材料,並具高效率、 並具產業應用價值。 本發明嘗試開發一種新型榮光 長壽命,製備容易、易於商業化, 【發明内容】 土七於先刚技術之缺失’本發明之目的在提供一種螢 光主^體材料。相較於習知之螢光主發光體材料,本發 2恋型?光主發光體材料具有提升螢光發光摻雜物之發 光效率、尚壽命以及容易合成與純化等優點。 本發明之另一目的係提供一種高發光效率、長壽命之 9 1379884 有機電激發光裝置,該發光裝置的發光層係包含本發明之 螢光主發光體材料。 為達上述目的,本發明之螢光主發光體材料係具有下 列化學式(I)所示之結構In view of the shortcomings of the prior art, the main illuminant material has high efficiency and industrial application value. The present invention attempts to develop a novel glory long life, which is easy to prepare and easy to commercialize. [Summary of the Invention] The present invention aims to provide a fluorescent host material. Compared with the conventional fluorescent main illuminant material, the present 2 love type? The photo-luminescence material has the advantages of improving the luminous efficiency, lifetime, and ease of synthesis and purification of the fluorescent luminescent dopant. Another object of the present invention is to provide a high luminous efficiency, long life 9 1379884 organic electroluminescent device, the luminescent layer of which comprises the fluorescent main illuminant material of the present invention. In order to achieve the above object, the fluorescent main light-emitting material of the present invention has the structure represented by the following chemical formula (I).

其中,Aq代表苯基(phenyl)或1-萘基(l-naphthyl), 1^及 L2 係各自獨立為 2,6-萘基(2,6-naphthalenyl),1,4-萘 基(l,4-naphthalenyl),1,4-苯烯基(l,4-phenylene),1,3-亞苯基(1,3-phenylene),1-萘基(1-naphthyl)或 2-萘基 (2-naphthyl ),Αγ2代表氫或C6-C20芳香環官能基。 在較佳實施態樣中,本發明之螢光主發光體材料係為 下列化學式所示之化合物:Wherein, Aq represents phenyl (phenyl) or 1-naphthyl (l-naphthyl), and 1 and L2 are each independently 2,6-naphthalenyl, 1,4-naphthyl (l , 4-naphthalenyl), 1,4-phenylene, 1,3-phenylene, 1-naphthyl or 2-naphthyl (2-naphthyl), Αγ2 represents hydrogen or a C6-C20 aromatic ring functional group. In a preferred embodiment, the fluorescent host material of the present invention is a compound of the formula:

10 1379884 (Inv-2) '10 1379884 (Inv-2) '

11 137988411 1379884

(Inv-7)。 ' 本發明另提供一種有機電激發光裝置,其係包含依以 下順序排列之層狀結構:透明基板、陽極層、電洞傳輸層、 發光層、電子傳輸層及陰極層;其中,陽極層及陰極層係 φ 分別與外部電源接觸形成電通路,該有機電機發光裝置之 特徵在於發光層中包含前述榮光主發光體材料。 在較佳實施態樣中,本發明之有機電激發光裝置之發 光層中進一步包含一螢光摻雜物,較佳地,該營光摻雜物 係為深藍色螢光摻雜物,特別是具有在Commission Internationale d’ Exclairage (CIEx,y)座標中具有 CIEx‘ 0.15,CIEyS0.18 之特性。 在更佳之具體實施態樣中,本發明之有機電激發光裝 置之發光層所包含之深藍色螢光摻雜物係具有下列化學式 φ 所示之結構:(Inv-7). The present invention further provides an organic electroluminescent device comprising a layered structure arranged in the following order: a transparent substrate, an anode layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode layer; wherein the anode layer and The cathode layer system φ is in contact with an external power source to form an electrical path, and the organic motor light-emitting device is characterized in that the light-emitting layer contains the aforementioned glory main light-emitting material. In a preferred embodiment, the luminescent layer of the organic electroluminescent device of the present invention further comprises a fluorescent dopant, and preferably, the camping dopant is a deep blue fluorescent dopant, in particular It has the characteristics of CIEx' 0.15, CIEyS0.18 in the coordinates of Commission Internationale d' Exclairage (CIEx, y). In a more preferred embodiment, the dark blue fluorescent dopant contained in the light-emitting layer of the organic electroluminescent device of the present invention has the structure shown by the following chemical formula:

f (BD-1)。 【實施方式】 本發明之螢光主發光體材料係具有下列化學式⑴所示 之結樽: 12 1379884 本發明之螢光主發光體材料係具有下列化學式⑴所示 之結構f (BD-1). [Embodiment] The fluorescent main illuminant material of the present invention has the following formula (1): 12 1379884 The fluorescent main illuminant material of the present invention has the structure represented by the following chemical formula (1)

其中’ Ari代表本基(phenyl)或1-萘基(1 _naphthyl), Li 及 L2 係各自獨立為 2,6-萘基(2,6_naphthalenyl),1,4-萘 基^1,4-11叩她也1^1),1,4-苯烯基(1,4_1)11如作狀),1,3_ ^ 笨基(U-phenylene)’ 1-萘基(1_naphthyl)或 2_萘基 (2-naphthyl ),An代表氫或C6-C20芳香環官能基。 列化2佳實施態樣巾’本發明之縣主發光體材料係為下 列化學式所示之化合物:Wherein 'Ari stands for phenyl or 1-naphthyl, Li and L2 are each independently 2,6-naphthalenyl, 1,4-naphthyl^1,4-11叩She also 1^1), 1,4-phenylenyl (1,4_1)11 as a form, 1,3_^ U-phenylene '1-naphthyl or 2-naphthyl (2-naphthyl), An represents hydrogen or a C6-C20 aromatic ring functional group. The present invention is a compound of the following formula:

13 137988413 1379884

14 i述、结構之本發明之化合物具有提升螢光發光摻雜物 之發光效率、高壽命以及容易合成與純化等優點。 • 在本發明之有機電激發光裝置,其係包含依以下順序 卜歹〗之層狀結構:透明基板、陽極層、電洞傳輸層、發光 層、電子傳輪層及陰極層;其中,陽極層及陰極層係分別 與外部電源接觸形成電通路,且除發光層以外之各層,其 ,各層材料之選用係屬本技術領域之通常知識而無須限 定’例如透明基板係可為具光穿透特性之不可撓玻璃基板 • 或者具可撓性之透明有機高分子材料;又如陽極層係可蛊 氡化銦錫(ITO)等。 _本發明之有機電激發光裝置其特徵在於發光層中包含 前述螢光主發光體材料。 在較佳實施態樣中,陽極層和電洞傳輸層之間係可進 一步包含一電洞注入層;電子傳輸層和陰極層之間係進一 步包含一電子注入層,其中,電洞注入層與電子注入層之 材料亦屬本技術領域之通常知識而無須限定。The compound of the present invention having the structure described above has the advantages of improving the luminous efficiency, high lifetime, and ease of synthesis and purification of the fluorescent dopant. The organic electroluminescent device of the present invention comprises a layered structure in the following order: a transparent substrate, an anode layer, a hole transport layer, a light-emitting layer, an electron transport layer and a cathode layer; wherein the anode The layers and the cathode layers are respectively in contact with an external power source to form an electrical path, and the layers other than the light-emitting layer are selected from the ordinary knowledge of the art without limitation. For example, the transparent substrate may be light-transmitting. Inflexible glass substrate with characteristics • Transparent organic polymer material with flexibility; and indium tin oxide (ITO) such as anode layer. The organic electroluminescent device of the present invention is characterized in that the luminescent main layer material is contained in the luminescent layer. In a preferred embodiment, the anode layer and the hole transport layer may further comprise a hole injection layer; the electron transport layer and the cathode layer further comprise an electron injection layer, wherein the hole injection layer and The material of the electron injecting layer is also a common knowledge in the art without limitation.

在目前有機電激發光裝置的發光層材料選用上,通常 會使用一螢光主發光體材料搭配一螢光摻雜物之設計來達 到南效率電激發光之效果。因此本發明之有機電激發光穿 置之發光層中係可進一步具有一螢光摻雜物,本發4之^ 光主發光體㈣衫限於提升紅色、綠色或£色^光換雜 物之效能,但較佳地,本發明之螢光主發光體材料係與藍 色螢光摻雜物共同構成發光層。藍色螢光摻雜物係可 技術領域已知之各種藍色螢光摻雜物之材料,样 含,但不,下列化學式解之毅色料軸物:-樣L 15 1379884In the current selection of the luminescent layer material of the organic electroluminescent device, a fluorescent main illuminant material and a fluorescent dopant are usually used to achieve the effect of the south efficiencies. Therefore, in the light-emitting layer of the organic electroluminescent light of the present invention, the fluorescent light-emitting layer can further have a fluorescent dopant, and the light-emitting main light-emitting body of the present invention is limited to lifting red, green or light-colored light-changing materials. Efficacy, but preferably, the fluorescent primary illuminant material of the present invention, together with the blue fluorescent dopant, constitutes a luminescent layer. The blue fluorescent dopant system can be a material of various blue fluorescent dopants known in the art, including, but not, the following chemical formula: A sample L 15 1379884

以下實施態樣係用於進一步了解本發明之優點,並非 用於限制本發明之申請專利範圍。 • 實施例1·本發明之螢光主發光«材料之合成 6二本棊砸酸(6-phenvl-nai?hthalene-2-Boronic acid)之合The following embodiments are intended to further understand the advantages of the present invention and are not intended to limit the scope of the invention. • Example 1 · Fluorescent main luminescence of the invention «Synthesis of material 6 bismuth acid (6-phenvl-nai?hthalene-2-Boronic acid)

AA

(2-Bromo-6-phenyl- naphthalene)、溶於 100ml 四氫吱喃, 反應溫度降至-78°C,逐滴加入20ml正丁基鐘(n-butyl lithium) ’反應1小時加入1 〇ml三乙基棚酸鹽(triethyl borate),反應1小時後回至〇。〇加入25ml稀鹽酸,攪拌 30分鐘,靜置分層取有機層,濃縮固體析出,過濾得固體, 固體以正己烷(n-hexane)洗,烘乾得成品5.9克,收率64.0%。 9-蕃-1-基-10-(6-笨某-蕃-2-基)-葱 (9-Naphthalen-1 -vl-10-("6-t)henvl-nat)hthalen-2-vjJ-anthrace ne)之合成(Inv-1 ) 1379884(2-Bromo-6-phenyl-naphthalene), dissolved in 100 ml of tetrahydrofuran, the reaction temperature was lowered to -78 ° C, and 20 ml of n-butyl lithium was added dropwise. 1 reaction was added for 1 hour. Methyl triethyl borate, reacted back to hydrazine after 1 hour. 25 ml of dilute hydrochloric acid was added to the mixture, and the mixture was stirred for 30 minutes. The organic layer was separated and separated, and the solid was concentrated. The solid was collected by filtration. The solid was washed with n-hexane and dried to yield 5.9 g of the product, yield 64.0%. 9-fan-1-yl-10-(6- phenyl-fan-2-yl)-onion (9-Naphthalen-1 -vl-10-("6-t)henvl-nat)hthalen-2- Synthesis of vjJ-anthrace ne) (Inv-1) 1379884

在氮氣下置入19.15克9-溴-10-萘-1-基-蒽 (9-Bromo-lO-naphthalen-l-yl- anthracene)、14.80 克 6-苯基 -萘-2-棚酸(6-phenyl-naphthalene-2_Boronic acid)、27.6 碳 酸鉀、35 ml水’ 200 ml四氫吱味和1.5克四(三苯基膦)他, 迴流反應隔夜(20小時),冷卻,加水逼出固體,過濾取固 體、烘乾,甲笨再結晶,過濾取固體,烘乾得成品16.4克, 純度99.1% ’收率65.0%。昇華純化後純度99.5%。 [HPLC 條件]管柱:rp_8,流速:1.0 ml/分鐘,CH3CN : H20= 90:10 4 NMR (400MHz)光譜數據:δ 8.05-8.09 (d,1H),7.96-8.10 (m, 5H), 7.76-7.91 (m, 3H), 7.60-7.70 (m, 5H), 7.40-7.59 (m,4H), 7.25-7.35 (m,6H) 6 -棚酸-[1,2’]_雙萘基(6*-Boronic acid-『1.2’lbinaphthalenvn 之合成19.15 g of 9-Bromo-lO-naphthalen-l-yl- anthracene and 14.80 g of 6-phenyl-naphthalene-2-butyric acid were placed under nitrogen ( 6-phenyl-naphthalene-2_Boronic acid), 27.6 potassium carbonate, 35 ml water '200 ml tetrahydroanthracene and 1.5 g of tetrakis(triphenylphosphine), refluxing overnight (20 hours), cooling, adding water to force solids The solid was taken by filtration, dried, and then crystallized and recrystallized. The solid was collected by filtration and dried to obtain 16.4 g of the finished product, and the purity was 99.1% 'yield 65.0%. The purity after sublimation purification was 99.5%. [HPLC conditions] column: rp_8, flow rate: 1.0 ml/min, CH3CN: H20 = 90:10 4 NMR (400 MHz) spectral data: δ 8.05-8.09 (d, 1H), 7.96-8.10 (m, 5H), 7.76-7.91 (m, 3H), 7.60-7.70 (m, 5H), 7.40-7.59 (m, 4H), 7.25-7.35 (m, 6H) 6 - shed acid-[1,2']_bisnaphthyl (6*-Boronic acid-"1.2'lbinaphthalenvn synthesis

在氮氣下置入16.0克6’ -溴-[1,2,]雙萘基 (6’-Bromo-[l,2’]binaphthalenyl)溶於 120ml 四氫咬喃,反 應溫度降至-78°C,逐滴加入22ml正丁基鐘(n-butyl 17 1379884 lithium)’反應1小時加入12ml三乙基硼酸鹽(triethyi borate),反應1小時後回至〇°C加入30ml稀鹽酸,攪拌 30分鐘,靜置分層取有機層,濃縮固體析出,過遽得固體, 固體以正己烷(n-hexane)洗’烘乾得成品8.3克,收率 56.0%。 6’-Π0-笨基-某-9基)-Γ1.2Ί镂茬某 (―Phenvl-anthracen-tvlMUlbinaphthalenvl)之合成 (Ιην·2)Under nitrogen, 16.0 g of 6'-bromo-[1,2,]bisnaphthyl (6'-Bromo-[l,2']binaphthalenyl) was dissolved in 120 ml of tetrahydroanthracene, and the reaction temperature was lowered to -78. C, 22 ml of n-butyl clock (n-butyl 17 1379884 lithium) was added dropwise to the reaction for 1 hour. Add 12 ml of triethyi borate. After 1 hour, return to 〇 ° C, add 30 ml of dilute hydrochloric acid, and stir 30 After a minute, the organic layer was separated and allowed to stand. The concentrated solid was precipitated, and the solid was solidified. The solid was washed with n-hexane to dryness to obtain 8.3 g of the finished product, yield 56.0%. Synthesis of 6'-Π0-stupyl-a-9-based)-Γ1.2Ί镂茬(-Phenvl-anthracen-tvlMUlbinaphthalenvl) (Ιην·2)

在氮氣下置入 16.6 克 9-溴-10-苯基-蒽 (9,Bromo_l〇-phenyl-anthracene)、17.80 克 6’-棚酸-[1,2’] 雙萘基(6’-B〇ronic acid-[l,2']binaphthalenyl)、27.6 石炭酸鉀、 35 ml水,200 ml四氫呋喃和1.6克四(三苯基膦)鈀,迴流 反應隔夜(20小時),冷卻,加水逼出固體,過濾取固體、 烘乾’甲苯再結晶,過濾取固體,烘乾得成品15.7克,純 度99.1%,收率62.0%。昇華純化後純度99.7%。 [HPLC 條件]管柱:RP-8,流速:1.〇 ml/分鐘,CH3CN : 100% 4 NMR (400MHz)光譜數據:δ 8.26 (d,1H),7.86-8.04 (m, 10H), 7.37-7.78 (m, 11H), 7.23-7.27 (m, 4H) 1379884 4-棚酸-6’-苯基-Π,2Ί譬萘某Γ 4-Boronic acid-Si-pheiryl-rU’lbinaDhthalenvn 之合成Under nitrogen, 16.6 g of 9-bromo-10-phenyl-anthracene (9,Bromo_l〇-phenyl-anthracene) and 17.80 g of 6'- linonic acid-[1,2']bisnaphthyl (6'-B) were placed under nitrogen. 〇ronic acid-[l,2']binaphthalenyl), 27.6 potassium carbonate, 35 ml water, 200 ml tetrahydrofuran and 1.6 g of tetrakis(triphenylphosphine)palladium, refluxed overnight (20 hours), cooled, and added with water to solidify The solid was filtered and dried, and the toluene was recrystallized, and the solid was collected by filtration, and dried to obtain 15.7 g of the finished product, the purity was 99.1%, and the yield was 62.0%. The purity after sublimation purification was 99.7%. [HPLC conditions] Column: RP-8, flow rate: 1. 〇ml/min, CH3CN: 100% 4 NMR (400 MHz) Spectral data: δ 8.26 (d, 1H), 7.86-8.04 (m, 10H), 7.37 -7.78 (m, 11H), 7.23-7.27 (m, 4H) 1379884 4-Sornic acid-6'-phenyl-anthracene, 2Ί譬naphthalene Γ 4-Boronic acid-Si-pheiryl-rU'lbinaDhthalenvn

在氮氣下置入10.2克4-溴-6,-苯基-[ι,2’ ]雙萘基 (4-Bromo-6’-phenyl-[l,2’]binaphthalenyl)、溶於 120ml 四 風》α夫味’反應溫度降至-78 C ’逐滴加入22ml正丁基鐘 (n-butyl lithium),反應1小時加入12ml三乙基硼酸鹽 (triethyl borate),反應1小時後回至〇。〇加入3〇ml稀鹽 酸,攪拌30分鐘,靜置分層取有機層,濃縮固體析出,過 渡得固體,固體以正己跪(n-hexane)洗,烘乾得成品8.3 克,收率56.0%。 6’茉基-4-Π0-茉某·茛-9-基罅蕙篡 (6,-Phenyl-4-n〇-phenyl-anthracen-9-vl)-rK2,lbmaphthalenv 1)之合成(Inv-3)10.2 g of 4-bromo-6,-phenyl-[1,2']binaphthalenyl) was dissolved under nitrogen, dissolved in 120 ml of four winds. 》α夫味'Reaction temperature dropped to -78 C' 22ml of n-butyl lithium was added dropwise, 12ml of triethyl borate was added for 1 hour, and the reaction was returned to 〇 after 1 hour. . 〇 Add 3 〇ml of dilute hydrochloric acid, stir for 30 minutes, let stand to separate the organic layer, concentrate the solid, and transfer to a solid. The solid is washed with n-hexane and dried to obtain 8.3 g of finished product, the yield is 56.0%. . Synthesis of 6'Mumyl-4-Π0-Momo 茛-9-ylindole (6,-Phenyl-4-n〇-phenyl-anthracen-9-vl)-rK2, lbmaphthalenv 1) (Inv- 3)

在氮氣下置入 16.6 克 9-溴-10-苯基-蒽 (9-Bromo-10_phenyl-anthracene)、21.6 克 4-硼酸-6,-苯基 -[1,2’] 雙萘基 ( 4-B〇ronic acidW-phenyiqiJ’Jbinaphthalenyl)、]?/ 碳酸钟、40 ml 水, 250 ml四氫呋喃和1.5克四(三苯基膦)鈀,迴流反應隔夜(20 19 1379884 小時)’冷卻’加水逼出固體,過濾取固體、烘乾,曱苯再 結晶,過濾取固體,烘乾得成品16.3克,純度99.2%,收 率56.0%。昇華純化後純度99.5%。 [HPLC 條件]管柱:RP-8,流速:1.0 ml/分鐘,CH3CN : 100% 4 NMR (400MHz)光譜數據:δ 8.33-8.42 (m,2H),8.06-8.11 (m, 2H), 7.94 (s, 1H), 7.55-7.79 (m, 7H), 7.43-7.52(m,4H), 7.12-7.41(m,14H) 4-棚酸-ΓΙ,Ι’1警萘基(4-Boronic acid-ri.ribinaDhthalenvl) 之合成Under nitrogen, 16.6 g of 9-bromo-10-phenyl-anthracene and 21.6 g of 4-boronic acid-6,-phenyl-[1,2']bisnaphthyl (4) were placed under nitrogen. -B〇ronic acidW-phenyiqiJ'Jbinaphthalenyl),]?/ Carbonic acid clock, 40 ml water, 250 ml tetrahydrofuran and 1.5 g of tetrakis(triphenylphosphine)palladium, refluxing overnight (20 19 1379884 hours) 'cooling' with water The solid was taken out, the solid was filtered, dried, and the benzene was recrystallized, and the solid was collected by filtration, and dried to obtain 16.3 g of the finished product, the purity was 99.2%, and the yield was 56.0%. The purity after sublimation purification was 99.5%. [HPLC conditions] column: RP-8, flow rate: 1.0 ml/min, CH3CN: 100% 4 NMR (400 MHz) Spectral data: δ 8.33-8.42 (m, 2H), 8.06-8.11 (m, 2H), 7.94 (s, 1H), 7.55-7.79 (m, 7H), 7.43-7.52 (m, 4H), 7.12-7.41 (m, 14H) 4- shed acid-ΓΙ, Ι '1 police naphthyl (4-Boronic acid -ri.ribinaDhthalenvl)

在氮氣下置入16.5克4_溴_[〗 〗,]雙萘基 (4-Bromo-[l,r]binaphthalenyl)、溶於 i〇〇ml 四氫呋喃, 反應溫度降至-78°C,逐滴加入2〇ml正丁基鋰(n_butyl lithium),反應1小時加入11m丨三乙基硼酸鹽(triethyl borate) ’反應1小時後回至0°C加入25mi稀鹽酸,擾拌 30分鐘’靜置分層取有機層’農縮固體析出,過遽得固體, 固體以正己烷(n-hexane)洗’共乾得成品8 〇5克,收率 54.0%。 20 1379884 4-(10-苯基-蒽-9-某νπ,ΐΊ蝥萘某 (4-n〇-Phenvl-anthracen,9-vn-ri.ribinaphthalenvl)之合成 (Inv-4)Under nitrogen, 16.5 g of 4_bromo_[〗 〖,]4-bromo-[l,r]binaphthalenyl) was dissolved in i〇〇ml tetrahydrofuran, and the reaction temperature was lowered to -78 ° C. 2 〇ml of n-butyl lithium was added dropwise, and 11 m of triethyl borate was added for 1 hour. After 1 hour of reaction, return to 0 ° C, add 25 mi of dilute hydrochloric acid, and stir for 30 minutes. The organic layer was precipitated in layers and precipitated as a solid, and the solid was solidified. The solid was washed with n-hexane to obtain a finished product of 8 〇 5 g, yield 54.0%. 20 1379884 4-(10-Phenyl-fluorene-9-a certain νπ, ΐΊ蝥naphthalene (4-n〇-Phenvl-anthracen, 9-vn-ri.ribinaphthalenvl) synthesis (Inv-4)

在氮氣下置入 16.6 克 9-溴-10-苯-蒽 (9-Bromo-10-phenyl-anthracene)、17.9 克 4-硼酸_6’_苯基 ® -[1,2’]雙萘基 (4-Boronic 汪。1(1-6’-卩11611>4-[1,2’]1^11&卩111:11&1611丫1)、27.6碳酸钟、4〇1111水, 270 ml四氫呋喃和1.6克四(三苯基膦)鈀,迴流反應隔夜(20 小時),冷卻,加水逼出固體,過濾取固體、烘乾,甲苯再 結晶,過濾取固體,烘乾得成品14.7克,純度99.1%,收 率58.0%。昇華純化後純度99.7%。 [HPLC 條件]管柱:RP-8,流速:1.0 ml/分鐘,CH3CN : H20= 90:10 φ 4 NMR (400MHz)光譜數據:δ 8.30-8.39 (m,2H),8.28-8.30 (d, 1H), 8.10-8.12 (d, 1H), 7.75-7.78 (d, 1H), 7.60-7.71(m,7H), 7.19-7.55(m,14H) 4-硼酸-『1,2’1 雙萘某(4-Boronic acid_「1.2’lbinat)hthalenvn 之合成Under nitrogen, 16.6 g of 9-Bromo-10-phenyl-anthracene and 17.9 g of 4-boronic acid _6'-phenyl®-[1,2'] bisnaphthyl group were placed under nitrogen. (4-Boronic Wang. 1 (1-6'-卩11611>4-[1,2']1^11&卩111:11&1611丫1), 27.6 carbonic acid clock, 4〇1111 water, 270 ml tetrahydrofuran And 1.6 g of tetrakis(triphenylphosphine)palladium, refluxing reaction overnight (20 hours), cooling, adding water to extract solids, filtering to take solids, drying, recrystallization of toluene, filtering to obtain solids, drying to obtain 14.7 g of finished product, purity 99.1%, yield 58.0%. Purity after purification by sublimation was 99.7% [HPLC conditions] column: RP-8, flow rate: 1.0 ml/min, CH3CN: H20 = 90:10 φ 4 NMR (400 MHz) Spectral data: δ 8.30-8.39 (m, 2H), 8.28-8.30 (d, 1H), 8.10-8.12 (d, 1H), 7.75-7.78 (d, 1H), 7.60-7.71 (m, 7H), 7.19-7.55 (m ,14H) 4-boronic acid-"1,2'1 double naphthalene (4-Boronic acid_"1.2'lbinat) hthalenvn synthesis

21 1379884 (4-Bromo-[l,2']binaphthalenyl)、溶於 i〇〇mi 四氫呋喃, 反應溫度降至-78°C,逐滴加入20ml正丁基鐘(n_butyl lithium),反應1小時加入11ml三乙基硼酸鹽(triethyi borate),反應1小時後回至0°C加入25ml稀鹽酸,授拌 30分鐘,靜置分層取有機層,濃縮固體析出,過濾得固體, 固體以正己烷(n-hexane)洗,烘乾得成品7.6克,收率 51.0% 〇 4-(10-苯基-蒽-9-基)-[1,2’]雙萘基 (4-Π〇-Ρ1^ηγ1-αιη1ΐΓ&〇6η-9-ν1)-Γ1,2ΊΜϊΊ&ρ1^1ιαΐ6ην1)之合成 (Ιην-5)21 1379884 (4-Bromo-[l,2']binaphthalenyl), dissolved in i〇〇mi tetrahydrofuran, the reaction temperature was lowered to -78 ° C, 20 ml of n-butyl lithium was added dropwise, and the reaction was added for 1 hour. 11ml of triethyi borate, after reacting for 1 hour, returning to 0 ° C, adding 25 ml of dilute hydrochloric acid, mixing for 30 minutes, standing to separate the organic layer, separating the solid to precipitate, filtering to obtain a solid, solid with n-hexane (n-hexane) washing, drying to obtain 7.6 g of finished product, yield 51.0% 〇4-(10-phenyl-fluoren-9-yl)-[1,2']bisnaphthyl (4-Π〇-Ρ1 Synthesis of ηγγ1-αιη1ΐΓ&〇6η-9-ν1)-Γ1,2ΊΜϊΊ&ρ1^1ιαΐ6ην1)(Ιην-5)

在氮氣下置入 16.6克 9-溴-10-苯基-蒽 (9-Bromo-10-phenyl-anthracene)、17.9 克 4-爛酸-[1,2’]雙 萘基(4-Boronic acid-[l,2’]binaphthalenyl)、27.6 碳酸鉀、 # 40 ml水’ 270 ml四氫咬喃和1.6克四(三苯基膦)纪,迴流 反應隔夜(20小時),冷卻,加水逼出固體,過濾取固體、 烘乾,甲苯再結晶,過濾取固體,烘乾得成品17.2克,純 度99.1%,收率68.0%。昇華純化後純度99.5%。 [HPLC 條件]管柱:RP-8,流速:1.0 ml/分鐘,CH3CN : H20= 90:10 NMR (400MHz)光譜數據:δ 8·33_8·39 (m,2H), 7.89-7.92 (d, 2H), 7.79-7.81 (d, 1H), 7.57-7.74 (m, 8H), 7.13-7.50(m,13H) 22 1379884 元件 壽命 (hr) 00 315 302 OO CN 298 VO ON 1—^ 203 Os OO 功率 效率" 3.03 4.20 4.29 3.51 4.264 3.32 3.52 3.39 發光 效率* 6.55 8.62 8.66 8.50 8.98 7.03 8.56 8.43 1 CIE· (0.15, 0.18) (0.15,0.18) (0.15, 0.17) (0.15, 0.18) (0.15, 0.17) (0.15, 0.16) (0.15,0.19) (0.15,0.19) 電子傳輸 層 (20 nm) Alq3 Alq3 Alq3 Alq3 Alq3 Alq3 Alq3 Alq3 發光層(25nm) 螢光 摻雜物 BD-1 BD-1 BD-1 BD-1 BD-1 BD-1 BD-1 BD-1 主發光體 材料 ADN Inv-1 Inv-2 Inv-3 Inv-4 Inv-5 Inv-6 Inv-7 電洞傳輸 層 (20 nm) NPB NPB NPB NPB NPB NPB NPB NPB 電洞注入 層 (60 nm) CuPC CuPC CuPC CuPC CuPC CuPC CuPC CuPC 比較例1 實施例1 實施例2 1 實施例3 實施例4 實施例5 I 實施例6 實施例7 ^痗铖奴回 w 3 日/p 3 Ο Ο 0^^^¾-驾«KtK賴 ^ί ^#¥^H-ao/v 日 OCN·^, 1379884 综上表可知’本發明之螢光主發光體材料其係且 提升螢光摻雜物之發光效率及壽命、以及易於合成料 等優點,並具商業化應用之潛力。 基他實施態樣 露ΐ所有特徵都可能與其他方法結 二in露的每一個特徵都可能選擇性的以相 =相等或::目的特徵所取代,因此,除了特別顯著的 拄ίίί外’ r有的本說明書所揭露的特徵僅是相等或相似 特徵中的一個例子。 ft發明已以較佳實施例揭露如上,然其並非用以 ==當=此技藝者’在不脱離本發明之精神 田J作各種之更動與潤飾。Under nitrogen, 16.6 g of 9-Bromo-10-phenyl-anthracene and 17.9 g of 4-rotonic acid-[1,2']bisnaphthyl (4-Boronic acid) were placed under nitrogen. -[l,2']binaphthalenyl), 27.6 potassium carbonate, #40 ml water' 270 ml tetrahydroanthracene and 1.6 g of tetrakis(triphenylphosphine), reflux reaction overnight (20 hours), cooling, adding water The solid was collected by filtration, dried, and then recrystallized from toluene. The solid was collected by filtration and dried to yield 17.1 g of the product, purity 99.1%, yield 68.0%. The purity after sublimation purification was 99.5%. [HPLC conditions] column: RP-8, flow rate: 1.0 ml/min, CH3CN: H20 = 90:10 NMR (400 MHz) Spectral data: δ 8·33_8·39 (m, 2H), 7.89-7.92 (d, 2H), 7.79-7.81 (d, 1H), 7.57-7.74 (m, 8H), 7.13-7.50 (m, 13H) 22 1379884 Component life (hr) 00 315 302 OO CN 298 VO ON 1—^ 203 Os OO Power efficiency " 3.03 4.20 4.29 3.51 4.264 3.32 3.52 3.39 Luminous efficiency* 6.55 8.62 8.66 8.50 8.98 7.03 8.56 8.43 1 CIE· (0.15, 0.18) (0.15, 0.18) (0.15, 0.17) (0.15, 0.18) (0.15, 0.17 (0.15, 0.16) (0.15, 0.19) (0.15, 0.19) Electron transport layer (20 nm) Alq3 Alq3 Alq3 Alq3 Alq3 Alq3 Alq3 Alq3 Luminescent layer (25 nm) Fluorescent dopant BD-1 BD-1 BD-1 BD-1 BD-1 BD-1 BD-1 BD-1 Main Luminescent Material ADN Inv-1 Inv-2 Inv-3 Inv-4 Inv-5 Inv-6 Inv-7 Hole Transport Layer (20 nm) NPB NPB NPB NPB NPB NPB NPB NPB hole injection layer (60 nm) CuPC CuPC CuPC CuPC CuPC CuPC CuPC CuPC Comparative Example 1 Example 1 Example 2 1 Example 3 Example 4 Example 5 I Example 6 Example 7 ^痗铖奴回w 3 3 /p 3 Ο Ο 0^^^3⁄4-Drive «KtK Lai ^ί ^#¥^H-ao/v Day OCN·^, 1379884 It can be seen from the above table that the fluorescent main illuminant material of the present invention has the advantages of improving the luminous efficiency and lifetime of the fluorescent dopant, and the ease of synthesizing materials, and has the potential for commercial application. All the features that may be associated with other methods may be selectively replaced by phase=equal or :: purpose features, so, except for the particularly significant 拄ίίί'r Some of the features disclosed in this specification are only one example of equal or similar features. The ft invention has been disclosed above in the preferred embodiment, but it is not intended to be used in the context of the present invention without departing from the spirit of the invention.

2828

Claims (1)

/V年’曰修(楚)正替揭d 十、申請專利範園^-101年10月η曰 之結構:種§7^發光體材料,係具有下聽學式⑴所示/V年'曰曰修(楚) is replacing the tenth, the application for patent gardens ^-101 October η曰 structure: species §7^ illuminant material, the system has the following listening formula (1) L 广 I<r-Ar2 其中,具有化學式⑴所示之該結構,I下列化合物:L broad I < r-Ar2 wherein, the structure represented by the chemical formula (1), I the following compounds: 之展t 有機電激發光裝置,其係包含依以下順序排列 、、’。冓.透明基板、陽極層、電洞傳輸層、發光層、 電子傳輸層及陰極層; ,^ 則述^極層及陰極層係分別與一外部電源接觸 形成電通路,該有機電機發光裝置之特徵在於發光層中包 1379884 ________________ ... 年("月’/q修(更)正替換頁 101年10月Π曰 含申請專利範圍第1項之螢光主發光體材料。 3. 如申請專利範圍第2項所述之裝置,其中前述陽極 ’ 層和電洞傳輸層之間係進一步包含一電洞注入層。 # 4. 如申請專利範圍第2項所述之裝置,其中前述電子 傳輸層和陰極層之間係進一步包含一電子注入層。 * 5. 如申請專利範圍第3項所述之裝置,其中前述發光 . 層係進一步包含一榮光摻雜物。 6. 如申請專利範圍第5項所述之裝置,其中前述螢光 摻雜物係為具有在 Commission Internationale d’ Exclairage (CIEx,y)座標中具有 CIEx^O.15,CIEy^O.18 之特性之· 深藍色螢光摻雜物。 7. 如申請專利範圍第6項所述之裝置,其中前述深藍 色螢光摻雜物係為下列化學式所示之化合物:The organic electroluminescent device is arranged in the following order. a transparent substrate, an anode layer, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode layer; wherein the gate layer and the cathode layer are respectively in contact with an external power source to form an electrical path, and the organic motor light-emitting device It is characterized by the inclusion of 1379884 ________________ ... in the luminescent layer ("month'/q repair (more) is replacing the page of October 101, containing the fluorescent main illuminant material of the patent application scope item 1. 3. The device of claim 2, wherein the anode layer and the hole transport layer further comprise a hole injection layer. [4] The device of claim 2, wherein the electron The device further comprises an electron injecting layer between the transport layer and the cathode layer. The apparatus of claim 3, wherein the illuminating layer further comprises a glory dopant. The device according to item 5, wherein the fluorescent dopant is characterized by having a characteristic of CIEx^O.15, CIEy^O.18 in the coordinates of the Commission Internationale d'Exclairage (CIEx, y). Light dopant 7. Application of the device according to item 6 patentable scope, wherein the compound represented by the following formula dark blue fluorescent dopant lines: (BD-1 )。(BD-1). 3131
TW096145860A 2007-12-03 2007-12-03 Organic electroluminescence apparatus and material thereof TW200925239A (en)

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