CN102167971B - Blue-fluorescence luminescent material and application thereof - Google Patents

Blue-fluorescence luminescent material and application thereof Download PDF

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CN102167971B
CN102167971B CN 201110049992 CN201110049992A CN102167971B CN 102167971 B CN102167971 B CN 102167971B CN 201110049992 CN201110049992 CN 201110049992 CN 201110049992 A CN201110049992 A CN 201110049992A CN 102167971 B CN102167971 B CN 102167971B
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blue
material
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organic electroluminescent
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肖立新
胡双元
邢星
陈志坚
曲波
龚旗煌
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北京大学
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Abstract

本发明公开了一种蓝色荧光发光材料及其应用。 The present invention discloses a blue fluorescent light-emitting material and its application. 该材料采用螺二芴为中心,连接两个菲基,形成扭曲非平面结构,有效避免了分子间的聚集,具有较高的荧光量子效率。 The materials used as the center spirobifluorene, connecting two phenanthryl, twist non-planar structure is formed, effectively prevent the aggregation between molecules with high fluorescence quantum efficiency. 该材料具有很好的热稳定性和电致发光特性,用作蓝色有机电致发光器件的发光层,能得到色纯度和效率非常高的蓝光发射。 Thermal and electrical stability of the material has good electroluminescent characteristics, used as a blue light-emitting layer of the organic electroluminescent device, color purity can be obtained very high efficiency and emitting blue light.

Description

一种蓝色荧光发光材料及其应用 One kind of a blue fluorescent light-emitting materials and their applications

技术领域 FIELD

[0001] 本发明涉及一种蓝色荧光发光材料,特别涉及一种用于有机电致发光器件(OLED)的蓝色荧光发光材料,以及该材料在蓝色荧光有机电致发光器件中的应用。 [0001] The present invention relates to a blue fluorescent light-emitting material, particularly to a fluorescent material for blue light emitting organic electroluminescent device (OLED), and the blue phosphor materials have application in organic electroluminescent devices .

背景技术 Background technique

[0002] 有机电致发光器件被认为是下一代超薄平面显示设备的新星。 [0002] The organic electroluminescent device is considered to be the next-generation flat thin display device star. 由于其具有材料选择范围宽、响应速度快、面发光、全彩显示、驱动电压低、可实现柔性显示等诸多优点,必定将成为液晶显示器、等离子体显示器等的强有力的竞争对手。 Because of its wide material selection range, fast response, surface emission, full-color display, low voltage driving can be realized flexible display and many other advantages, will become a strong competitor to a liquid crystal display, a plasma display or the like. 虽然现在全世界有许多研究机构和公司投入了大量的精力去研究和开发有机电致发光器件,但是和人们的预期相比,其产业化程度还相差甚远,其中,只有小型的手机显示屏对有机电致发光技术应用较好。 Although there are many research institutions around the world and the company has invested a lot of effort to research and development of organic electroluminescent devices, but people's expectations and compared to its level of industrialization is still far, of which only a small mobile phone display for organic electroluminescence technology better. 究其原因,在有机电致发光领域,尚有许多关键问题没有得到真正解决,如色纯度、发光稳定性、有缘驱动技术和封装技术等方面,还存在着一定的问题,使得有机电致发光器件的寿命短,效率较低。 The reason, in the organic electroluminescence art, there are many critical problem is not really solved, such as the aspect of color purity, luminance stability, affinity and packaging technology, drive technology, there are still some problems, such organic electroluminescent short lifetime of the device efficiency is low.

[0003] 为了提升有机电致发光器件的性能,对发光材料的研究十分重要。 [0003] In order to improve the performance of the organic electroluminescent device has, the study of the luminescent material is important. 选择发光材料必须满足以下几个要求:1、高量子效率的荧光特性;2、良好的半导体特性;3、良好的成膜性和热稳定性;4、良好的光稳定性。 Choosing the luminescent material must meet the following requirements: 1. high quantum efficiency of fluorescence properties; 2, good semiconductor characteristics; 3, good film-forming property and thermal stability; 4, good light stability. 目前在OLED材料研究中,绿光和红光材料的性能已经非常出色,可以达到商品化的要求,而蓝光材料的研究则相对比较薄弱,这也制约着基于红绿蓝三原色发光的OLED全彩显示的发展。 In the present study OLED materials, green and red material performance has been very good, can meet the requirements of commercial, research and blue material is relatively weak, which restricts the red, green and blue light-emitting based on the full-color OLED development displayed. 一般来说,由于蓝光材料具有较宽的带隙,很难同时满足蓝光材料对高效率和高色纯度的要求。 In general, since blue light has a wider bandgap material, the blue light is difficult to meet the material requirements for high efficiency and high color purity. 如何做好这两个方面的平衡,成为开发优秀蓝光材料的关键。 How to balance these two aspects, the key to the development of outstanding blue material.

[0004] 虽然目前已经有很多OLED蓝色发光材料,但是具有高效率和高色纯度的蓝光材料并不多见。 [0004] Although there are already many OLED blue light emitting material, but the material blue light having high efficiency and high color purity rare. 发明内容 SUMMARY

[0005] 本发明的一个目的在于提供一种可用作蓝色荧光发光材料的化合物,该化合物用于有机电致发光器件中,能得到色纯度和效率非常高的蓝光发射。 [0005] An object of the present invention is to provide a compound useful as a blue fluorescent light-emitting material, the compound for organic electroluminescent devices, color purity can be obtained very high efficiency and emitting blue light.

[0006] 本发明的第二个目的是提供上述蓝色荧光发光材料在有机电致发光器件中的应用。 [0006] A second object of the present invention is to provide the blue fluorescent light-emitting material in the light-emitting device applied organic electroluminescence.

[0007] 本发明的蓝色荧光发光材料,是结构式如式I或者式2所示的化合物,简称为DPSBF: [0007] The blue fluorescent light-emitting material of the present invention is a compound of formula I or formula in formula 2, referred to as DPSBF:

[0008] [0008]

Figure CN102167971BD00041

[0009] 式I 式2 [0009] Formula I Formula 2

[0010] 其中Rl〜R9和R/〜R9'为氢,以及四个碳以内的烷基,含氧烷基。 [0010] wherein Rl~R9 and R / ~R9 'is hydrogen, and less than four carbon alkyl group, an oxygen-containing group.

[0011] 上述蓝色荧光发光材料的制备方法,包括如下步骤: [0011] The method of preparing the blue fluorescent light-emitting material, comprising the steps of:

[0012] 通过2,7- 二溴螺二芴或者2,2'- 二溴螺二芴和取代菲基-9-硼酸的Suzuki反应制得式I或者式2所示的化合物。 [0012] by a 2,7-dibromo-dibromo-2,2'-spirobifluorene or spirobifluorene phenanthryl and substituted 9-boronic acid Suzuki reaction to obtain a compound represented by formula I or formula 2.

[0013] 其中,在上述步骤中,2,7- 二溴螺二芴或者2,2,- 二溴螺二芴和取代菲基-9-硼酸是在氮气或惰性气体的保护下,以Pd(PPh3)4或醋酸钯为催化剂,在80-100°C的条件下回流反应12-36小时。 [0013] wherein, in the above step, spirobifluorene or 2,7-dibromo 2,2 - dibromo spirobifluorene substituted phenanthryl and 9-boronic acid under a nitrogen blanket or inert gas, with Pd (PPh3) 4, or palladium acetate as catalyst, the reaction was refluxed for 12-36 hours at 80-100 ° C in.

[0014] 以Rl〜R9和R1 '〜R9'均为氢为例,2,7-二溴螺二芴和取代菲基-9-硼酸制备第一蓝色荧光发光材料DPSBFl的反应流程如下(a)所示,2,2'-二溴螺二芴和取代菲基-9-硼酸制备第二蓝色荧光发光材料DPSBF2的反应流程如下(b)所示: [0014] In Rl~R9 and R1 '~R9' are hydrogen, for example, 2,7-dibromo-substituted phenanthryl and spirobifluorene boronic acid reaction scheme -9- first blue fluorescent material DPSBFl follows ( a), and 2,2'-dibromo-substituted phenanthryl spirobifluorene boronic acid reaction scheme -9- second blue fluorescent material DPSBF2 follows (b) below:

Figure CN102167971BD00042

[0016] [0016]

Figure CN102167971BD00051

[0017] 反应流程 [0017] Reaction Scheme

[0018] 要提高发光材料的色纯度,必须抑制分子内π共轭体系,降低共轭度。 [0018] To improve color purity of the luminescent material, necessary to suppress the intramolecular π conjugation system, reducing the degree of conjugation. 本发明采用非共平面的螺芴结构和共轭度较小的菲基相连接,得到了具有扭曲结构的蓝色荧光发光材料DPSBF。 The present invention uses non-coplanar spiro fluorene structure and a smaller degree of conjugation phenanthryl connected, whereby a blue fluorescent material DPSBF has a twisted structure. 该蓝色荧光发光材料具有很高的荧光量子效率和色纯度。 The blue fluorescent light emitting material having high fluorescent quantum efficiency and color purity.

[0019] 本发明提供的上述蓝色突光发光材料可用于蓝色有机电致发光器件的发光层。 [0019] The blue light-emitting material of the present invention, projections may be provided for the blue light-emitting layer of the organic electroluminescent device. 所制备的蓝色有机电致发光器件一般包括依次叠加的ITO导电玻璃衬底(阳极)、空穴传输层(NPB),发光层(DPSBF单独或者掺杂使用)、电子传输层(PBD)、电子传输层(Alq3)、电子注入层(LiF)和阴极层(Al)。 The prepared blue organic electroluminescent devices typically include ITO glass substrate sequentially superimposed (anode), a hole transport layer (of NPB), a light emitting layer (DPSBF used alone or doped), an electron transport layer (the PBD), an electron transport layer (Alq3), an electron injection layer (LiF) and a cathode layer (Al). 所有功能层均可采用真空蒸镀或者溶液成膜工艺。 All the functional layer by vacuum deposition or solution can forming process. 该器件中所用到的一些有机化合物的分子结构式如下所示: Some of the molecular structure of organic compounds used in the device as follows:

[0020] [0020]

Figure CN102167971BD00052

[0021] 当然,本发明器件的功能层并不限于使用上述材料,这些材料可以用其他材料代替,比如空穴传输层可以用TH)等代替,电子传输层可以用BPhen,TPBI等代替。 [0021] Of course, functional layer in a device of the present invention is not limited to the above materials, these materials may be used in place of other materials, such as a hole transport layer may TH) and the like instead of the electron transport layer may be replaced BPhen, TPBI and the like. 这些材料 These materials

的分子结构式如下所示: The molecular structure is shown below:

[0022] [0022]

Figure CN102167971BD00061

[0023] 本发明的蓝色荧光材料应用于蓝色有机电致发光器件中,显示出很高的色纯度,该材料的主要优点在于: [0023] The blue phosphor material of the present invention is applied to a blue organic electroluminescent device exhibits high color purity, the main advantage of this material is that:

[0024] I)该材料采用以螺二芴为中心,连接两个菲基,形成扭曲非平面结构,有效避免了分子间的聚集,具有较高的荧光量子效率,以香豆素C102为基准,测得化合物(I)在氯仿溶剂中的荧光量子效率为0.94,化合物(2)在氯仿溶剂中的荧光量子效率为0.90。 [0024] I) The material employed to spirobifluorene center, connected to two phenanthryl, twist non-planar structure is formed, effectively prevent the aggregation between molecules with high fluorescence quantum efficiency, as a reference coumarin C102 measured compound (I) fluorescence quantum efficiency in a chloroform solvent was 0.94, the compound (2) fluorescence quantum efficiency in a chloroform solvent was 0.90.

[0025] 2)该材料具有很好的热稳定性,分解温度高达400°C。 [0025] 2) the material has good thermal stability, decomposition temperature up to 400 ° C.

[0026] 该材料具有很好的电致发光特性,以化合物⑴为发光材料制备的蓝色有机电致发光器件,器件的发光波长为436nm,CIE坐标为(0.15,0.08),非常接近NTSC的标准蓝色(0.14,0.08)。 [0026] The material has excellent electroluminescent properties, preparation of compound ⑴ blue light emitting material has an emission wavelength of the organic electroluminescent device, the device is 436nm, CIE coordinates (0.15, 0.08), very close to the NTSC standard blue (0.14, 0.08).

附图说明 BRIEF DESCRIPTION

[0027] 图1为根据实施例1制备的DPSBFl在氯仿溶液中的紫外_可见吸收光谱和荧光发射光谱; [0027] FIG. 1 is a UV DPSBFl in a chloroform solution prepared in Example 1 _ visible absorption spectrum and fluorescence emission spectrum;

[0028] 图2为实施例3中以DPSBFl作为蓝色荧光有机电致发光器件的发光层,器件的电压-电流密度-亮度曲线; [0028] FIG. 2 is a DPSBFl to Example 3 as a blue fluorescent light-emitting layer of the organic electroluminescent device, the device of the voltage - current density - luminance curve;

[0029] 图3为实施例3中以DPSBFl作为蓝色荧光有机电致发光器件的发光层,器件的电流密度-电流效率-流明效率曲线; [0029] FIG 33 to DPSBFl as blue fluorescent light-emitting layer of the organic electroluminescent device of Example, the current density of the device - current efficiency - luminous efficacy curve;

[0030] 图4为实施例3中以DPSBFl作为蓝色荧光有机电致发光器件的发光层,器件在达到lOOcd/m2时的电致发光光谱图; [0030] FIG. 4 of Example 3 to DPSBFl as blue fluorescent light-emitting layer of the organic electroluminescent device, the device reaching the electroluminescence spectrum when electrically lOOcd / m2;

[0031] 图5为实施例4中以DPSBFl作为蓝色荧光有机电致发光器件的发光层,器件的电压-电流密度-亮度曲线; [0031] FIG. 5 of Example 4 to DPSBFl as blue fluorescent light-emitting layer of the organic electroluminescent device, the device of the voltage - current density - luminance curve;

[0032] 图6为实施例4中以DPSBFl作为蓝色荧光有机电致发光器件的发光层,器件的电流密度-电流效率-流明效率曲线; [0032] FIG. 6 to DPSBFl as blue fluorescent light-emitting layer of the organic electroluminescent device of Example 4, the current density of the device - current efficiency - luminous efficacy curve;

[0033] 图7为实施例4中以DPSBFl作为蓝色荧光有机电致发光器件的发光层,器件在达到lOOcd/m2时的电致发光光谱图; [0033] FIG. 7 is a DPSBFl to Example 4 as a blue fluorescent light-emitting layer of the organic electroluminescent device, the device reaching the electroluminescence spectrum when electrically lOOcd / m2;

[0034] 图8为实施例5中以DPSBF2作为蓝色荧光有机电致发光器件的发光层,器件的电压-电流密度-亮度曲线; [0034] FIG. 8 is DPSBF2 to Example 5 as a blue fluorescent light-emitting layer of the organic electroluminescent device, the device of the voltage - current density - luminance curve;

[0035] 图9为实施例5中以DPSBF2作为蓝色荧光有机电致发光器件的发光层,器件的电流密度-电流效率-流明效率曲线; [0035] FIG. 9 to DPSBF2 as blue fluorescent light-emitting layer of the organic electroluminescent device of Example 5, the current density of the device - current efficiency - luminous efficacy curve;

[0036] 图10为实施例5中以DPSBF2作为蓝色荧光有机电致发光器件的发光层,器件在达到lOOcd/m2时的电致发光光谱图。 [0036] In FIG 10 is reached lOOcd / m2 electroluminescence spectrum of the electrical device to DPSBF2 Example 5 as a blue fluorescent light-emitting layer of the organic electroluminescent device.

具体实施方式 detailed description

[0037] 以下各实施例进一步说明本发明的内容,但不应理解为对本发明的限制。 [0037] The following examples further illustrate the present invention but should not be construed as limiting the present invention.

[0038] 实施例1蓝色荧光发光材料DPSBFl (式I)的制备及性质一 Example 1 blue fluorescent light emitting material DPSBFl (Formula I) Preparation and Properties of a [0038] Embodiment

[0039] I)合成第一蓝色荧光发光材料DPSBFl (式I) [0039] I) Synthesis of the first blue light emitting fluorescent material DPSBFl (Formula I)

[0040] 往三口烧瓶中加入1.314g 2,7-二溴螺芴(2.773mmol)和1.353g菲-9-硼酸(6.097mmol),用混合溶剂溶解(IOOmL甲苯,50mL乙醇),然后加入50mL Na2CO3水溶液(2M),通氮气搅拌Ih以除去反应瓶中的氧气。 [0040] To three-necked flask were added 1.314g 2,7- dibromo fluorene spiro (2.773mmol) phenanthrene-9-boronic acid and 1.353g (6.097mmol), was dissolved with a mixed solvent (IOOmL toluene, 50mL of ethanol), followed by addition of 50mL aqueous Na2CO3 (2M), stirred Ih nitrogen to remove oxygen in the reaction flask. 然后加入Pd(PPh3)40.710g(0.614mmol),强力搅拌下回流,反应过程通过TLC控制。 Was then added Pd (PPh3) 40.710g (0.614mmol), under vigorous stirring at reflux, the reaction control by TLC. 反应24h后,往反应液中加入50mL去离子水,过滤除去不溶物,将水相和有机相分离,水相用CH2Cl2萃取(20mL每次,3次),将有机相混合以后减压蒸懼浓缩到约5mL,柱层析进行分离,淋洗剂用CH2Cl2: hexane (I: 4)。 After 24h the reaction, the reaction mixture was added to 50mL of deionized water, insolubles were filtered off, the aqueous phase and the organic phase was separated, the aqueous phase was extracted with CH2Cl2 (20 mL each time, three times), the organic phase was evaporated under reduced pressure after mixing fear was concentrated to approximately 5mL, was separated by column chromatography eluted with CH2Cl2: hexane (I: 4). 得到1.362g白色固体。 To give a white solid 1.362g. 粗产品在CVD中280°C升华提纯,得到纯产品0.865g(产率为46.7% )。 The crude product in CVD 280 ° C sublimation purification, to give 0.865 g of pure product (yield 46.7%).

[0041] 1H 匪R(CDC13,TMS,δ ):8.70 (d, 2H), 8.65 (d, 2H), 8.05 (d, 2H) , 7.81 (d, 4H), [0041] 1H bandit R (CDC13, TMS, δ): 8.70 (d, 2H), 8.65 (d, 2H), 8.05 (d, 2H), 7.81 (d, 4H),

7.75 (d, 2H),7.54-7.63 (m, 10H),7.44 (t,2H),7.34 (t,2H),7.19 (t,2H),7.00 (d, 2H), 7.75 (d, 2H), 7.54-7.63 (m, 10H), 7.44 (t, 2H), 7.34 (t, 2H), 7.19 (t, 2H), 7.00 (d, 2H),

6.96(s,2H).[0042] 2) DPSBFl的紫外-可见吸收光谱以及荧光光谱 . 6.96 (s, 2H) [0042] 2) DPSBFl ultraviolet - visible absorption spectra and fluorescence spectra

[0043] 所制备的DPSBFl在溶液状态下紫外-可见吸收光谱如图1所示。 DPSBFl [0043] prepared in a solution state ultraviolet - visible absorption spectrum as shown in FIG. 该DPSBFl在氯仿溶液中的吸收谱有一个位于254nm的最大吸收峰,同时在310nm和327nm处还有两个小峰,对应分子中的菲基结构。 The chloroform solution DPSBFl absorption spectrum has a maximum absorption peak is located at 254nm, 310nm and at the same time there are two smaller peaks at 327nm, corresponding to the structure of the molecule phenanthryl. 该DPSBFl的荧光发射峰位于383nm,为蓝紫色发光。 The fluorescence emission peak located DPSBFl 383nm, blue-violet light.

[0044] 实施例2第二蓝色荧光发光材料DPSBF2 (式2)的制备 Preparing a second blue fluorescent light emitting material DPSBF2 (Formula 2) [0044] Example 2

[0045] I)合成第二蓝色荧光发光材料DPSBF2 (式2) [0045] I) Synthesis of the second blue fluorescent material DPSBF2 (Formula 2)

[0046] 往三口烧瓶中加入1.015g 2,2'- 二溴螺芴(2.142mmol)和L 045g菲-9-硼酸(4.707mmol),用混合溶剂溶解(IOOmL甲苯,50mL乙醇),然后加入50mL Na2CO3水溶液(2M),通氮气搅拌Ih以除去反应瓶中的氧气。 [0046] To three-necked flask were added 1.015g 2,2'- dibromo-spirofluorene (2.142mmol) and L 045g phenanthrene-9-boronic acid (4.707mmol), was dissolved with a mixed solvent (IOOmL toluene, 50 mL of ethanol) was added 50mL Na2CO3 solution (2M), stirred Ih nitrogen to remove oxygen in the reaction flask. 然后加入Pd (PPh3)40.550g(0.474mmol),强力搅拌下回流,反应过程通过TLC控制。 Was then added Pd (PPh3) 40.550g (0.474mmol), under vigorous stirring at reflux, the reaction control by TLC. 反应24h后,往反应液中加入50mL去离子水,过滤除去不溶物,将水相和有机相分离,水相用CH2Cl2萃取(20mL每次,3次),将有机相混合以后减压蒸馏浓缩到约5mL,柱层析进行分离,淋洗剂用CH2Cl2: hexane (I: 4)。 After 24h the reaction, the reaction mixture was added to 50mL of deionized water, insolubles were filtered off, the aqueous phase and the organic phase was separated, the aqueous phase was extracted with CH2Cl2 (20 mL each time, three times), the organic phase was concentrated by distillation under reduced pressure after mixing to about 5mL, was separated by column chromatography eluted with CH2Cl2: hexane (I: 4). 得到1151g白色固体。 1151g to give a white solid. 粗产品在CVD中280°C升华提纯,得到纯产品0.635g(产率为44.4% )。 The crude product in CVD 280 ° C sublimation purification, to give 0.635 g of pure product (yield 44.4%).

[0047] 1H 匪R(CDC13,TMS,δ ):8.73 (d, 2H), 8.67 (d, 2H), 7.92 (d, 4H) , 7.73 (s, 2H), [0047] 1H bandit R (CDC13, TMS, δ): 8.73 (d, 2H), 8.67 (d, 2H), 7.92 (d, 4H), 7.73 (s, 2H),

7.61-7.68 (m, 12H),7.47 (t, 2H),7.33 (d, 2H),7.25 (t, 2H),7.08 (t, 2H),7.02 (t, 2H).[0048] 实施例3第一蓝色突光发光材料DPSBFl在有机电致发光器件中的应用一 7.61-7.68 (m, 12H), 7.47 (t, 2H), 7.33 (d, 2H), 7.25 (t, 2H), 7.08 (t, 2H), 7.02 (t, 2H). [0048] Example 3 the first blue light emitting material DPSBFl projecting in the organic electroluminescent device has application in a

[0049] 本实施例按照下述方法制备蓝色荧光有机电致发光器件: [0049] The present Example was prepared by the following method blue fluorescent organic electroluminescent device:

[0050] a)清洗ITO (氧化铟锡)玻璃:分别用去离子水、丙酮、乙醇超声清洗ITO玻璃各15分钟,然后在等离子体清洗器中处理2分钟; [0050] a) Cleaning ITO (indium tin oxide) glass: deionized water, respectively, acetone, ethanol ITO glass ultrasonic cleaning for 15 minutes each, and then treated in a plasma cleaner for 2 minutes;

[0051] b)在阳极ITO玻璃上真空蒸镀或者溶液成膜空穴传输层NPB,厚度为50nm ; [0051] b) vacuum deposition on an ITO glass anode or the hole transport layer forming solution NPB, a thickness of 50 nm;

[0052] c)在空穴传输层NPB之上,真空蒸镀发光层DPSBFl,厚度为30nm ; [0052] c) on the hole transport layer NPB, vacuum deposition emitting layer DPSBFl, a thickness of 30 nm;

[0053] d)在发光层DPSBFl之上,真空蒸镀电子传输层PBD,厚度为IOnm ; [0053] d) on the light emitting layer DPSBFl, vacuum deposition electron transporting layer PBD, thickness IONM;

[0054] e)在空穴阻挡层PBD之上,真空蒸镀电子传输层Alq3,厚度20nm ;[0055] f)在电子传输层Alq3之上,真空蒸镀电子注入层LiF,厚度0.5nm; [0054] e) In the above hole blocking layer PBD, vacuum deposition electron transporting layer Alq3, a thickness of 20nm; [0055] f) over the electron transporting layer Alq3, an electron injection layer vacuum deposition LiF, 0.5nm thickness;

[0056] g)在电子注入层LiF之上,真空蒸镀阴极Al,厚度为lOOnm。 [0056] g) over the electron injection layer LiF, vacuum deposition cathode Al, having a thickness of lOOnm.

[0057]器件的结构为 IT0/NPB(50nm)/DPSBF (30nm)/PBD (IOnm)/Alq3 (20nm)/LiF (0.5nm)/Al (lOOnm)。 Structure [0057] The device of IT0 / NPB (50nm) / DPSBF (30nm) / PBD (IOnm) / Alq3 (20nm) / LiF (0.5nm) / Al (lOOnm). 以实施例1制备的DPSBFl作为该器件的发光层,该器件的电压-电流密度-亮度曲线如图2所示,电流密度-电流效率曲线如图3所示。 In DPSBFl prepared according to Example 1 as a light emitting layer of the device, the device voltage - current density - luminance curve shown in Figure 2, the current density - current efficiency curve shown in FIG. 器件的启亮电压为5.5V,最大亮度达1916cd/m2,最大电流效率1.24cd/A。 Qiliang voltage of the device is 5.5V, the maximum brightness of 1916cd / m2, the maximum current efficiency 1.24cd / A. 图4为该器件在lOOcd/m2时的电致发光光谱图,CIE坐标位于(0.15,0.08)。 FIG 4 for the electrical device when lOOcd / m2 electroluminescence spectrum, CIE coordinate is (0.15, 0.08).

[0058] 实施例4第一蓝色荧光发光材料DPSBFl在有机电致发光器件中的应用二 [0058] Example 4 DPSBFl first blue fluorescent material in the organic light-emitting device is applied two-induced

[0059] 本实施例按照下述方法制备蓝色荧光有机电致发光器件: [0059] This Example was prepared by the following method blue fluorescent organic electroluminescent device:

[0060] a)清洗ITO (氧化铟锡)玻璃:分别用去离子水、丙酮、乙醇超声清洗ITO玻璃各15分钟,然后在等离子体清洗器中处理2分钟; [0060] a) Cleaning ITO (indium tin oxide) glass: deionized water, respectively, acetone, ethanol ITO glass ultrasonic cleaning for 15 minutes each, and then treated in a plasma cleaner for 2 minutes;

[0061] b)在阳极ITO玻璃上真空蒸镀或者溶液成膜空穴传输层NPB,厚度为50nm ; [0061] b) vacuum deposition on an ITO glass anode or the hole transport layer forming solution NPB, a thickness of 50 nm;

[0062] c)在空穴传输层NPB之上,真空蒸镀发光层DPSBFl,厚度为30nm ; [0062] c) on the hole transport layer NPB, vacuum deposition emitting layer DPSBFl, a thickness of 30 nm;

[0063] d)在发光层DPSBFl之上,共同蒸镀电子传输层PBD和Alq3,控制PBD和Alq3的速率比为1: 2,厚度为30nm; [0063] d) on the light emitting layer DPSBFl, co-evaporation, and Alq3 electron transporting layer PBD, PBD and rate control Alq3 ratio of 1: 2, with a thickness of 30 nm;

[0064] e)在PBDMlq3之上,真空蒸镀电子注入层LiF,厚度为0.5nm ; [0064] e) above PBDMlq3, vacuum deposition electron injection layer LiF, having a thickness of 0.5nm;

[0065] f)在电子注入层LiF之上,真空蒸镀阴极Al,厚度为lOOnm。 [0065] f) over the electron injection layer LiF, vacuum deposition cathode Al, having a thickness of lOOnm.

[0066]器件的结构为 ITO/NPB(5Onm)/DPSBF(3Onm)/PBD: Alq3(l: 2,30nm)/LiF(0.5nm)/Al (IOOnm)。 [0066] The structure of the device is ITO / NPB (5Onm) / DPSBF (3Onm) / PBD: Alq3 (l: 2,30nm) / LiF (0.5nm) / Al (IOOnm). 以实施例1制备的DPSBFl作为该器件的发光层,该器件的电压-电流密度-亮度曲线如图5所示,电流密度-电流效率曲线如图6所示。 In DPSBFl prepared according to Example 1 as a light emitting layer of the device, the device voltage - current density - luminance curve shown in Figure 5, the current density - current efficiency curve shown in Figure 6. 器件的启亮电压为5V,最大亮度达到3794cd/m2,最大电流效率提高到1.38cd/A。 Qiliang voltage of the device is 5V, the maximum brightness of 3794cd / m2, the maximum current efficiency to improve 1.38cd / A. 图7为器件在IOOcd/m2时的电致发光光谱图,CIE坐标位于(0.16,0.12)。 7 is an electrical device at IOOcd / m2 electroluminescence spectrum, CIE coordinate is (0.16,0.12).

[0067] 实施例5第二蓝色荧光发光材料DPSBF2在有机电致发光器件中的应用三 [0067] The second blue fluorescent light emitting material 5 DPSBF2 embodiments have application in organic electroluminescent devices Three

[0068] 本实施例按照下述方法制备蓝色荧光有机电致发光器件: [0068] This Example was prepared by the following method blue fluorescent organic electroluminescent device:

[0069] a)清洗ITO (氧化铟锡)玻璃:分别用去离子水、丙酮、乙醇超声清洗ITO玻璃各15分钟,然后在等离子体清洗器中处理2分钟; [0069] a) Cleaning ITO (indium tin oxide) glass: deionized water, respectively, acetone, ethanol ITO glass ultrasonic cleaning for 15 minutes each, and then treated in a plasma cleaner for 2 minutes;

[0070] b)在阳极ITO玻璃上真空蒸镀或者溶液成膜空穴传输层NPB,厚度为50nm ; [0070] b) vacuum deposition on an ITO glass anode or the hole transport layer forming solution NPB, a thickness of 50 nm;

[0071] c)在空穴传输层NPB之上,共同蒸镀发光层DPSBF2和MADN,厚度为10nm,MADN的掺杂比例为1% ; [0071] c) on the hole transport layer NPB, and co-evaporation DPSBF2 MADN emitting layer, a thickness of 10nm, MADN doping ratio is 1%;

[0072] d)在掺杂发光层DPSBF2和MADN之上,真空蒸镀电子传输层PBD,厚度为50nm ; [0072] d) on the light emitting layer doped DPSBF2 and MADN, vacuum deposition electron transporting layer PBD, having a thickness of 50 nm;

[0073] e)在电子传输层PBD之上,真空蒸镀电子注入层LiF,厚度为0.5nm ; [0073] e) over the electron transporting layer PBD, vacuum deposition electron injection layer LiF, having a thickness of 0.5nm;

[0074] f)在电子注入层LiF之上,真空蒸镀阴极Al,厚度为lOOnm。 [0074] f) over the electron injection layer LiF, vacuum deposition cathode Al, having a thickness of lOOnm.

[0075]器件的结构为 IT0/NPB(50nm)/DPSBF: I % wtMADN(IOnm)/PBD(50nm)/LiF (0.5nm) /Al (IOOnm)。 Structure [0075] The device of IT0 / NPB (50nm) / DPSBF: I% wtMADN (IOnm) / PBD (50nm) / LiF (0.5nm) / Al (IOOnm). 以实施例2制备的DPSBF2为发光层,该器件的电压-电流密度-亮度曲线如图5所示,电流密度-电流效率曲线如图6所示。 Prepared in Example 2 to DPSBF2 embodiment is a light emitting layer, the device voltage - current density - luminance curve shown in Figure 5, the current density - current efficiency curve shown in Figure 6. 器件的启亮电压为3V,最大亮度达到800cd/m2,最大电流效率提高到1.97cd/A。 Qiliang voltage of the device is 3V, a maximum brightness of 800cd / m2, current efficiency to increase the maximum 1.97cd / A. 图7为器件在lOOcd/m2时的电致发光光谱图,CIE 坐标位于(0.15,0.08)。 7 is an electrical device at lOOcd / m2 electroluminescence spectrum, CIE coordinate is (0.15, 0.08).

[0076] 最后需要注意的是,公布实施例的目的在于帮助进一步理解本发明,但是本领域的技术人员可以理解:在不脱离本发明及所附的权利要求的精神和范围内,各种替换和修改都是可能的。 [0076] Finally, it should be noted that the published object of embodiments is to assist in a further understanding of the invention, those skilled in the art will appreciate: within the spirit and scope of the claims without departing from the present invention and the appended claims, various alternatives and modifications are possible. 因此,本发明不应局限于实施例所公开的内容,本发明要求保护的范围以权利要求书界定的范围为准。 Accordingly, the content of the present invention should not be limited to the disclosed embodiment embodiment, the scope of the present invention is required to scope of the claims and their equivalents.

Claims (4)

  1. 1.一种蓝色突光发光材料,如式I或式2所不: A blue light emitting material projections, such as Formula I or Formula 2 is not:
    Figure CN102167971BC00021
    式I和式2中,Rl〜R9和R/〜R9'为氢。 In Formula I and Formula 2, Rl~R9 and R / ~R9 'is hydrogen.
  2. 2.权利要求1所述蓝色荧光发光材料作为有机电致发光材料的用途。 The blue fluorescent light emitting material 1 as claimed in claim 2. The use as having an organic electroluminescent material.
  3. 3.一种蓝色有机电致发光器件,其特征在于,其发光层的材料为权利要求1所述的蓝色突光发光材料。 A blue organic electroluminescent device, characterized in that the material of which the blue light emitting layer is projecting said light-emitting material as claimed in claim 1.
  4. 4.一种蓝色有机电致发光器件,其特征在于,其发光层掺杂使用如权利要求1所述的蓝色荧光发光材料。 A blue organic electroluminescent device, characterized in that it is used as the light emitting layer is doped according to claim 1 blue fluorescent light emitting material.
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