CN117242157A - 一种混合物及其在光电领域的应用 - Google Patents
一种混合物及其在光电领域的应用 Download PDFInfo
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- CN117242157A CN117242157A CN202280026668.6A CN202280026668A CN117242157A CN 117242157 A CN117242157 A CN 117242157A CN 202280026668 A CN202280026668 A CN 202280026668A CN 117242157 A CN117242157 A CN 117242157A
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Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/115—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising active inorganic nanostructures, e.g. luminescent quantum dots
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09D11/107—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds from unsaturated acids or derivatives thereof
-
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Abstract
一种混合物及其在光电领域的应用,所述混合物包含一种作为主体材料的有机化合物H、一种无机纳米发光体E和一种有机树脂;所述有机树脂可以便于用印刷或涂布的方法形成薄膜,并且通过加热固化或紫外固化;所述有机化合物H吸收激发光源的光,并将能量转移给发光E体;所述发光体E的光致发光光谱具有较窄的半峰宽,其可以吸收有机化合物H的能量,然后发射出半峰宽较窄的出射光;而且该发光体优先选自量子点,其光致发光光谱的波峰位置可以通过组分及大小来调节,从而能够分别发射不同颜色的光谱。这些不同颜色的窄半峰宽发光器件可以制造具有高色域的显示器件。
Description
本发明涉及有机电子材料和器件技术领域,特别是涉及一种混合物和组合物,包含其或由其制备的有机薄膜及其在光电领域的应用。
根据色度学原理,射入人眼的光的半峰宽越窄,色纯度越高,颜色越鲜艳。用这种半峰宽窄的红绿蓝三原色光制作的显示装置,显示的色域大,画面真实,画质好。
当前主流的全彩显示实现的方法不外乎两种,第一种,显示器件主动发射红、绿、蓝三原色的光,典型的如RGB-OLED显示;目前成熟的技术是利用精细金属掩膜的真空蒸镀制作三种颜色的发光器件,工艺复杂,成本高,难以实现超过600ppi的高分辨率显示。第二种是采用色转换器将发光器件发射的单一色光转换成多种色光,从而实现全彩显示,如三星公司的蓝光OLED加红绿量子点(QD)薄膜作为颜色转换器。这种方法中的发光器件工艺简单,良率高,而且颜色转换器可以通过蒸镀、喷墨打印、转印、光刻等不同技术实现,可以应用在不同分辨率要求的显示产品上,低如大尺寸电视,只有50ppi,高如硅基微型显示,分辨率可达3000ppi以上。
目前颜色转换器中使用的最有希望的颜色转换材料是无机纳米晶,俗称量子点,这是一类直径介于2-8nm的无机半导体材料(InP,CdSe,CdS,ZnSe等)的纳米颗粒(特别是量子点)。限于当前的量子点合成和分离技术,目前含Cd的量子点发光峰的半峰宽在25-40nm,色纯度可以满足NTSC的显示要求,无Cd量子点的半峰宽在35-75nm之间。然而,由于量子点的消光系数普遍较低,需要较厚的膜,典型的10微米以上的膜才能实现蓝光的完全吸收,这对量产工艺,特别是三星公司的蓝光OLED加红绿量子点的技术方案是个很大的挑战。
因此从产业角度,迫切希望找到一种既能保持量子点窄的发光谱的特点,同时又能降低膜的厚度的颜色转换器的材料解决方案。
发明内容
基于此,本发明的目的是提供一种混合物和组合物,包含其或由其制备的有机薄膜及其在光电领域中的应用。
具体技术方案如下:
本发明提供一种混合物,包含一种有机化合物H、一种无机纳米发光体E和一种有机树脂,其特征在于,1)所述有机化合物H的发光谱在所述无机纳米发光体E的吸收谱的短波长的一侧,且至少部分相互重叠;2)所述无机纳米发光体E的发光谱的半峰宽(FWHM)小于或等于45nm。
在上述的混合物中,所述无机纳米发光体E选自具有单分布的胶体量子点或纳米棒。
在上述的混合物中,所述无机纳米发光体E包含有半导体材料,选自CdSe,CdS,CdTe,ZnO,ZnSe,ZnS,ZnTe,HgS,HgSe,HgTe,CdZnSe,InAs,InP,InN,GaN,InSb,InAsP,InGaAs,GaAs,GaP,GaSb,AlP,AlN,AlAs,AlSb,CdSeTe,ZnCdSe,PbSe,PbTe,PbS,PbSnTe,Tl
2SnTe
5及它们的任何组合。
本发明还提供一种组合物,包含一种如上所述的混合物和至少一种溶剂。
本发明还提供一种有机功能材料薄膜,包含一种如上所述的混合物。
本发明还提供一种光电器件,包含一种如上所述的混合物或有机功能材料薄膜。
有益效果:按照本发明的一种混合物,其中有机化合物H具有较大的消光系数,无机纳米发光体E具有较高的发光效率和较窄的发光半峰宽,而且有机化合物H和无机纳米发光体E之 间的能量转换效率较高,从而实现吸收和发光功能的分离优化,便于制备厚度较薄的高效率颜色转换器,用于实现具有高色域的显示器;另外,有机化合物H可以选择较易合成的化合物,且比重较高,可以较大的降低成本。
图1:一种红绿蓝三色的显示装置示意图。
为了便于理解本发明,下面将参照相关附图对本发明进行更全面的描述。附图中给出了本发明的较佳实施例。但是,本发明可以以许多不同的形式来实现,并不限于本文所描述的实施例。相反地,提供这些实施例的目的是使对本发明的公开内容的理解更加透彻全面。
除非另有定义,本文所使用的所有的技术和科学术语与属于本发明的技术领域的技术人员通常理解的含义相同。本文中在本发明的说明书中所使用的术语只是为了描述具体的实施例的目的,不是旨在于限制本发明。本文所使用的术语“和/或”包括一个或多个相关的所列项目的任意的和所有的组合。
在本发明中,主体材料、基质材料、Host材料和Matrix材料具有相同的含义,可以互换。
在本发明中,金属有机络合物,金属有机配合物,有机金属配合物具有相同的含义,可以互换。
在本发明中,组合物、印刷油墨、油墨、和墨水具有相同的含义,可以互换。
本发明提供一种混合物,包含一种有机化合物H、一种无机纳米发光体E和至少一种有机树脂,1)所述有机化合物H的发光谱在所述无机纳米发光体E的吸收谱的短波长的一侧,且至少部分相互重叠;2)所述无机纳米发光体E的发光谱的半峰宽(FWHM)小于或等于45nm。
在一个优先的实施例中,所述无机纳米发光体E的发光谱的半峰宽(FWHM)≤45nm,较好是≤40nm,更好是≤35nm,更更好是≤30nm,最好是≤25nm。
在另一个优先的实施例中,所述无机纳米发光体E,其荧光量子效率(PLQY)≥60%,较好是≥65%,更好是≥70%,最好是≥80%。
在某些实施例中,所述的无机纳米发光体E选自半导体纳米发光晶体,钙钛矿量子点,金属纳米团簇。
在一个优先的实施例中,所述的无机纳米发光体E是半导体纳米发光晶体。
在某些实施例中,半导体纳米发光晶体的平均粒径约在1到1000nm范围内。在某些实施例中,半导体纳米发光晶体的平均粒径约在1到100nm。在某些实施例中,半导体纳米发光晶体的平均粒径约在1到20nm,最好的是从1到10nm。
形成半导体纳米发光晶体的半导体可以包含一个第四族元素,一组II-VI族化合物,一组II-V族化合物,一组III-VI族化合物,一组III-V族化合物,一组IV-VI族化合物,一组I-III-VI族化合物,一组II-IV-VI族化合物,一组II-IV-V族化合物,一个包括上述任何一类的合金,和/或包括上述各化合物的混合物,包括三元、四元的混合物或合金。一个非限制性的例子清单包括氧化锌,硫化锌,硒化锌,碲化锌,氧化镉,硫化镉,硒化镉,碲化镉,硫化镁,硒化镁,砷化镓,氮化镓,磷化镓,硒化镓,锑化镓,氧化汞,硫化汞,硒化汞,碲化汞,砷化铟,氮化铟,磷化铟,锑化铟,砷化铝,氮化铝,磷化铝,锑化铝,氮化钛,磷化钛,砷化钛,锑化钛,氧化铅,硫化铅,硒化铅,碲化铅,锗,硅,一个包括上述任何化合物的合金,和/或一个包括上述任何化合物的混合物,包括三元、四元混合物或合金。
在一个很优先的实施例中,半导体纳米发光晶体包含有II-VI族半导体材料,优先选自CdSe,CdS,CdTe,ZnO,ZnSe,ZnS,ZnTe,HgS,HgSe,HgTe,CdZnSe及它们的任何组合。 在合适的实施例中,由于CdSe的合成相对成熟而将此材料用作用于可见光的无机纳米发光体。
在另一个优先的实施例中,半导体纳米发光晶体包含有III-V族半导体材料,优先选自InAs,InP,InN,GaN,InSb,InAsP,InGaAs,GaAs,GaP,GaSb,AlP,AlN,AlAs,AlSb,CdSeTe,ZnCdSe及它们的任何组合。
在另一个优先的实施例中,半导体纳米发光晶体包含有IV-VI族半导体材料,优先选自PbSe,PbTe,PbS,PbSnTe,Tl
2SnTe
5及它们的任何组合。
半导体纳米晶体的形状和其他纳米粒子的例子可以包括球形,棒状,盘状,十字形,T形,其他形状,或它们的混合物。制造半导体纳米晶体的方法有多种,一个优先的方法是控制生长的溶液相胶体法。有关此法的详细内容可参见Alivisatos,A.P,Science 1996,271,p933;X.Peng等,J.Am.Chem.Soc.1997,119,p7019;和C.B.Murray等J.Am.Chem.Soc.1993,115,p8706。特此上述列出的文件中的内容并入本文作为参考。在这些方法中,将在高温发生热解的有机金属前躯体(包含有一M施主和一X施主,如下述)迅速注射入含有表面活性剂(配位溶剂)的热溶液中。这些前体在高温分裂并且反应成为纳米晶核。在此初始离散成核阶段之后,通过向生长的晶体加入单体开始生长阶段。产物是溶液中自支撑(free-standing)的晶体纳米粒子,它们具有包覆其表面的有机表面活性剂分子。此合成方法包括在数秒间进行的初始离散成核,及之后在高温下数分钟的晶体生长。通过改变参数,比如温度、表面活性剂的种类、前躯体的量、和表面活性剂与单体的比率,可以改变反应的本性和过程。温度控制成核过程、前体分解速率和生长速率。有机表面活性剂分子调节溶解性并控制纳米晶体形状。表面活性剂与单体、表面活性剂彼此之间、单体彼此之间的比率以及各个单体的浓度强烈地影响晶粒生长动力学。通过适当的控制反应参数,得到的半导体纳米晶体有很窄的分布,即所谓的单分散分布的粒径。单分散分布的直径也可以作为晶粒大小的量度。在本发明中,单分散的晶粒集合中至少60%以上晶粒的颗粒大小在指定范围内。一个较好的单分散的晶体,其直径的偏差少于15%rms,更好是少于10%rms,最好是少于5%rms。术语"单分散分布的纳米晶体"、"纳米点"和"量子点"易于被本领域普通技术人员理解为表示同样的结构体,并且在本发明中可互换地使用。
在一个优先的实施例中,半导体发光纳米晶体或量子点包括由第一半导体材料组成的核心和第二个半导体材料组成的外壳,其中外壳至少沉积在核心表面的一部分。一种包含有核心和外壳的半导体纳米晶体也被称为“核/壳”半导体纳米晶体或量子点。
在半导体纳米晶体中,光发射由纳米晶体的带边状态产生。来自发光纳米晶体的带边发射与来源于表面电子态的辐射和非辐射衰变通道竞争。表面缺陷如悬挂键提供非辐射复合中心,从而降低发光效率。将表面缺陷状态钝化和移除的一个有效方法是在纳米晶体的表面上外延生长无机壳材料(参见X.Peng等,J.Am.Chem.Soc.Vol119,7019-7029(1997))。可以选择壳材料,使得壳/核构成I型半导体异质结结构,这样可以将电子和空穴,及它们复合而成的激子局限于核中,从而将非放射复合的概率降低。通过将含有壳材料的有机金属前体加入到含有核纳米晶体的反应混合物中得到核-壳结构体。在这种情况下,不是在成核事件之后生长,而是核起到晶核的作用,并且从它们的表面上生长壳。反应的温度应保持适当的低,以有利于向核表面加入壳材料单体,同时防止壳材料的纳米晶体独立成核。反应混合物中存在表面活性剂以引导壳材料的控制生长并且确保溶解性。当在两种材料之间存在低的晶格失配时,得到均一且外延生长的壳。此外,球形起到将来自大曲率半径的界面应变能最小化的作用,从而防止形成可以劣化纳米晶体的光学性质的错位。
例如,半导体发光纳米晶体可以包括一个核心,其一般化学式为MX,其中M可以是镉,锌,镁,汞,铝,镓,铟,铊或其混合物,X可以是氧,硫,硒,碲,氮,磷,砷,锑,或它们的混合物。适合作为半导体纳米晶体的核使用的材料的例子包括但不限于,ZnO,ZnS,ZnSe,ZnTe,CdO,CdS,CdSe,CdTe,MgS,MgSe,GaAs,GaN,GaP,GaSe,GaSb,HgO,HgS,HgSe, HgTe,InAs,InN,InP,InSb,AlAs,AlN,AlP,AlSb,TIN,TIP,TlAs,TlSb,PbO,PbS,PbSe,PbTe,Ge,Si,一个包括上述任何材料的合金或混合物,包括三元,四元混合物或合金。
组成外壳的半导体材料可以是跟核心成分相同或不同。半导体纳米晶体的外壳是包在核心表面上的外套,其材料可以包含一组第四族元素,一组II-VI族化合物,一组II-V族化合物,一组III-VI族化合物,一组III-V族化合物,一组IV-VI族化合物,一组I-III-VI族化合物,一组II-IV-VI族化合物,一组II-IV-V族化合物,一个包括上述任何一类的合金,和/或包括上述各化合物的混合物。例子包括但不限于,ZnO,ZnS,ZnSe,ZnTe,CdO,CdS,CdSe,CdTe,MgS,MgSe,GaAs,GaN,GaP,GaSe,GaSb,HgO,HgS,HgSe,HgTe,InAs,InN,InP,InSb,AlAs,AlN,AlP,AlSb,TIN,TIP,TlAs,TlSb,PbO,PbS,PbSe,PbTe,Ge,Si,一个包括上述任何化合物的合金和/或混合物。
例如,ZnS,ZnSe或CdS外壳可以生长在CdSe或CdTe半导体纳米晶体上。例如,在美国专利US6322901公开了一种外壳生长的方法。通过调整外壳生长过程中反应混合物的温度,及监测核心吸收光谱,具有高量子效率和窄粒度分布的“核/壳”半导体纳米晶体或量子点可以被制备。外壳可包括一个或更多的层。外壳包括至少一种半导体材料,它跟核心组成相同或不同。优选地,外壳的厚度约为1到10个单层膜。一个外壳也可以有一个大于10个单层膜的厚度。在某些实施例中,可以有超过一个外壳包在一个核心上。
在某些实施例中,外围的“外壳”材料可以有一个带隙比核心材料带隙大,较好的,核/壳具有I型的异质结结构。
在某些实施例中,外壳可以选择,以便有一个原子间距接近“核心”。在其他一些实施例中,外壳和核心材料可以具有相同的晶体结构。“核/壳“半导体纳米晶体或量子点包括,例如但不限于:红色(如“CdSe/ZnS”),绿色(如“CdZnSe/CdZnS“),蓝色(如“CdS/CdZnS“)。半导体纳米晶体或量子点的窄粒度分布使得具有窄宽度光谱的光发射成为可能。量子点的详细描述可参见以下文献:Murray等(J.Am.Chem.Soc,1993,115,p8706),Christopher Murray的论文"Synthesis and Characterization of II-VI Quantum Dots and Their Assembly into 3-D Quantum Dot Superlattices"麻省理工学院1995年9月,及美国专利US6322901,特此将其全部内容并入本文作为参考。
在某些实施例中,可以引入两个或两个以上的壳,如CdSe/CdS/ZnS和CdSe/ZnSe/ZnS核/壳/壳结构(J.Phys.Chem.B2004,108,p18826),通过中间壳(CdS或ZnSe)在硒化镉核心和硫化锌外壳之间,可以有效减少纳米晶体里面的应力,因为有CdS和ZnSe的晶格参数介于CdSe和ZnS中间,这样可得到近乎无缺陷的纳米晶体。
配位溶剂中,有控制生长的过程和成核后半导体纳米晶体的退火处理也能导致表面均匀衍生化和均匀的核心结构。随着粒度分布变窄,温度可提高以保持稳定生长。通过添加更多的M施主或X施主,生长周期可缩短。M施主可以是无机化合物,有机金属化合物,或者金属元素。M可以是镉,锌,镁,汞,铝,镓,铟,铊。X施主是一个能于M施主发生反应,并形成具有一般式MX的材料的化合物。X施主可以是硫族施主或磷属元素化合物施主,如磷化氢硫族化合物,双氧,铵盐或三硅烷磷化物。适用的X施主包括双氧(dioxygen),bis(trimethylsilyl)selenide((TMS)
2Se),trialkyl phosphine selenides如(tri-n-octylphosphine)selenide(TOPSe)或(tri-n-butylphosphine)selenide(TBPSe),trialkyl phosphine tellurides如(tri-n-octylphosphine)telluride(TOPTe)或hexapropylphosphorustriamide telluride(HPPTTe),bis(trimethylsilyl)telluride((TMS)
2Te),bis(trimethylsilyl)sulfide((TMS)
2S),一种trialkyl phosphine sulfide如(tri-n-octylphosphine)sulfide(TOPS),一种铵盐(ammonium salt)如铵卤化物(ammonium halide)(如NH
4Cl),tris(trimethylsilyl)phosphide((TMS)
3P), tris(trimethylsilyl)arsenide((TMS)
3As),或tris(trimethylsilyl)antimonide((TMS)
3Sb)。
在一个优先的实施中M施主和X施主可以包含在同一分子中。
一个配位溶剂可以帮助控制半导体纳米晶体的生长。配位溶剂是一种具有孤对施主的化合物,举例来说,有一个孤对电子可与一个不断增长的半导体纳米晶体的表面配位。溶剂的这种配位效应可稳定半导体纳米晶体的生长。配位溶剂的例子包括烷基膦(alkyl phosphines),烷基膦氧化物(alkyl phosphine oxides),烷基膦酸(alkyl phosphonic acids),或alkyl phosphinic acids。然而,其他配位溶剂,如吡啶(pyridines),呋喃(furans),和胺(amines)也可能适用于制备半导体纳米晶体。其他适当的配位溶剂的例子包括吡啶(pyridine),三正辛基膦(tri-n-octyl phosphine(TOP)),三正辛基氧膦(tri-n-octyl phosphine oxide(TOPO))和三(3-羟基丙基)膦(trishydroxylpropylphosphine(tHPP)),三丁基膦(tributylphosphine),tri(dodecyl)phosphine,亚磷酸二丁酯(dibutyl-phosphate),亚磷酸三丁酯(tributyl phosphate),亚磷酸三(十八烷基)脂(trioctadecyl phosphate),亚磷酸三(十二烷基)脂(trilauryl phosphate),亚磷酸十三烷酯(tris(tridecyl)phosphate),亚磷酸三异癸基脂(triisodecyl phosphate),磷酸二异辛酯(bis(2-ethylhexyl)phosphate),tris(tridecyl)phosphate,十六烷基胺(hexadecylamine),9-十八烯胺(oleylamine),十八烷基胺(octadecylamine),二异辛胺(bis(2-ethylhexyl)amine),辛胺(octylamine),二正辛胺(dioctylamine),三辛胺(trioctylamine),十二胺(dodecylamine),双十二烷胺(didodecylamine),三月桂胺(tridodecylamine),十六烷基胺(hexadecylamine),N-十八烷基-1-十八胺(dioctadecylamine),trioctadecylamine,苯基磷酸(phenylphosphonic acid),正己基磷酸(hexylphosphonic acid),正十四烷基磷酸(tetradecylphosphonic acid),正辛基磷酸(octylphosphonic acid),磷酸正十八酯(octadecylphosphonic acid),丙烯二磷酸酯(propylenediphosphonic acid),苯基膦酸(phenylphosphonic acid),aminohexylphosphonic acid,二辛醚(dioctyl ether),二苯醚(diphenyl ether),肉豆蔻酸甲酯(methyl myristate),辛酸辛酯(octyl octanoate),和辛酸己酯(hexyl octanoate)。在某些实施例中,可以使用工业用TOPO。
在成长阶段的反应过程中的大小分布可通过监测粒子吸收或发射谱线的宽度来估算。对因粒子吸收光谱变化作相应的反应温度的修正可允许在整个生长过程中都有一个尖锐的颗粒尺寸分布。在晶体生长过程中反应物可以被添加到成核溶液而生长较大的晶粒。例如,对于硒化镉和碲化镉,通过在特定的半导体纳米晶体的平均直径时终止生长,并选择适当的半导体材料组成,半导体纳米晶体的发射光谱可300nm到850m的范围内连续调节,特别优先的是从400nm到800nm。
半导体的纳米晶粒尺寸分布可以通过不良溶剂来进行选择性沉淀而得到进一步细化,如在美国专利US6322901B1描述的甲醇/丁醇。例如,半导体纳米晶体可以分散在含10%丁醇的正己烷溶液中。甲醇可滴加这个搅拌中的溶液,直到乳光仍然存在。通过离心分离上层清液与絮凝产生一个富含大晶粒的沉淀物。此过程可反复进行,直到没有进一步的光学吸收光谱锐化可观察到。尺寸选择性沉淀可以在各种各样的溶剂/非溶剂对中进行,包括吡啶/正己烷,氯仿/甲醇等。大小选定的半导体纳米晶体集合较好有不超过15%rms或更少,更好是10%rms或更少,最好是5%rms或更少。
在某些实施例中,较好的,半导体纳米晶体有附着在上面的配体。
在某些实施例中,配体可以从在生长过程中使用的配位溶剂衍生出来。表面修饰可通过反复接触一个含有过剩的竞争性的配位组团来形成一个覆盖层。例如,包裹的半导体纳米晶体的分散体可以用配位有机化合物来处理,如吡啶,产生的晶粒可容易地分散于吡啶,甲醇,芳烃溶剂,但不再分散于脂肪族溶剂。这种表面交换过程,可以通过任何化合物来进行,只要它能 配位或结合到半导体纳米晶体的外表面,此类化合物的例子包括膦,硫醇,胺和磷酸盐。半导体纳米晶体也可以暴露于一短链聚合物,此聚合物的一端和半导体纳米晶体有一种亲和力,另一端有一个基团,它与半导体纳米晶体所分散的液体介质亲和。这种亲和性提高了悬浮稳定性并阻碍了半导体纳米晶体絮凝。另外,在某些实施例中,半导体纳米晶体也可以使用非配位溶剂来制备。
更具体的说,配位配体有化学式:
(Y-)
k-n-(X)-(-L)
n
其中k是2,3,4或5,n为1,2,3,4或5,这样k-n使得不小于零;X选自O,O-S,O-Se,O-N,O-P,O-As,S,S=O,SO
2,Se,Se=O,N,N=O,P,P=O,C=O As,或As=O;每个Y和L,是相互独立的,可以是H,OH,芳基,杂芳基,或直链或支链的含有C2-C18碳链的烃,此烃可选择地至少含有一个双键,至少有一个三键,或至少一个双键和三键。其中的烃链可以任选被一个或更多的如下基团取代:C1-C4烷基和C2-C4烯基和C2-4炔,C1-C4烷氧基,羟基,卤基,氨基,硝基,氰基,C3-C5环烷基,3-5环杂烷基(3-5membered heterocycloalkyl),芳基,杂芳基,C1-C4 alkylcarbonyloxy,C1-C4 alkyloxycarbonyl,C1-C4 alkylcarbonyl,或甲酰。其中的烃链,也可以任选地被如下基团打断:-O-,-S-,-N(Ra)-,-N(Ra)-C(O)-O-,-O-C(O)-N(Ra)-,-N(Ra)-C(O)-N(Rb)-,-O-C(O)-O-,-P(Ra)-,或-P(O)(Ra)-,每个Ra和Rb,是相互独立的,可以是氢,烷基,烯基,炔基,烷氧基,羟烷基(hydroxylalkyl),羟基或卤烷基。一个芳基是取代或非取代的环芳香基团。例子包括苯,萘,甲苯,蒽基,硝基苯,或卤代苯基。杂芳基是一个有一个或多个杂原子的芳基,比如呋喃环,吡啶,吡咯,菲基。
一个合适的配位配体可以商业购买或通过普通有机合成技术制备,例如,J.March在Advanced Organic Chemistry所描述的,而其全部参考文献在此纳入作为参考。美国专利US7160613公开了其他的一些配体,特此将其全部内容并入本文作为参考。
半导体纳米晶体或量子点的发光光谱可以是窄高斯型的。通过调整纳米晶粒的大小,或纳米晶粒组成,或两者,半导体纳米晶体或量子点的发光光谱可连续从紫外线,可见光或红外线光谱的整个波长范围调节。例如,一个含有CdSe的量子点,可在可见光区域内调节,一个包括砷化铟的或量子点可以在红外线区域内调节。一个发光半导体纳米晶体或量子点其窄的粒度分布导致了一个窄的发光光谱。晶粒的集合可呈现单分散,较好是直径偏差小于15%rms,更好是少于10%rms,最好是小于5%rms。对于发可见光的半导体纳米晶粒或量子点,其发光光谱在一个窄的范围内,一般来说不大于75nm,较好是不大于60nm,更好是不大于40nm,最较好是不大于30nm半高宽(FWHM)。对于发红外光的或量子点,其发光光谱可以有不大于150nm的半高宽(FWHM),或不大于100nm的半高宽(FWHM)。发光光谱随着量子点粒度分布的宽度的变窄而变窄。
半导体纳米晶体或量子点可以有比如大于10%,20%,30%,40%,50%,60%的量子发光效率。在一个优先的实施例中,半导体纳米晶体或量子点的量子发光效率大于70%,更好是大于80%,最好是大于90%。
量子点窄的半高宽会导致有饱和色彩的发光。利用单一材料就可在整个可见光范围内实现具有广泛可调,饱和色彩的发光,这是任何有机生色团无法比拟的(参见例如Dabbousi等,J.Phys.Chem.1997,101,p9463)。量子点发光波长范围较窄。一个包括一个以上的量子点的图案可以在一个以上的窄的发光范围内发光。人们感知的光的颜色可以通过选择量子点的大小和材料的适当组合来控制。透射电子显微镜(TEM)可提供有关量子点的大小,形状和晶粒分布的信息。粉末X射线衍射(XRD)图谱可以提供最完整的有关晶粒类型和晶粒质量的信息。晶粒大小也可通过X射线相干长度,粒子的直径于峰宽成反比关系来估算。例如,量子点的直径可以直接从透射电子显微镜测量或利用例如Scherrer公式从X射线衍射数据估计。它也可从紫外/可见吸收光谱估计。
其他可能对本发明有用的材料,技术,方法,应用和信息,在以下专利文献中有所描述,WO2007/117698,WO2007/120877,WO2008/108798,WO2008/105792,WO2008/111947,WO2007/092606,WO2007/117672,WO2008/033388,WO2008/085210,WO2008/13366,WO2008/063652,WO2008/063653,WO2007/143197,WO2008/070028,WO2008/063653,US6207229,US6251303,US6319426,US6426513,US6576291,US6607829,US6861155,US6921496,US7060243,US7125605,US7138098,US7150910,US7470379,US7566476,WO2006134599A1,特此将上述列出的专利文件中的全部内容并入本文作为参考。
在另一个优先的实施例中,半导体发光纳米晶体是纳米棒。纳米棒的特性不同于球形纳米晶粒。例如,纳米棒的发光沿长棒轴偏振化,而球形晶粒的发光式非偏振的(参见Woggon等,Nano Lett.,2003,3,p509)。纳米棒具有优异的光学增益特性,使得它们可能用作激光增益材料(参见Banin等Adv.Mater.2002,14,p317)。此外,纳米棒的发光可以可逆地在外部电场的控制下打开和关闭(参见Banin等,Nano Lett.2005,5,p1581)。纳米棒的这些特性可以在某种情况下优先地结合到本发明的器件中。制备半导体纳米棒的例子有,WO03097904A1,US2008188063A1,US2009053522A1,KR20050121443A,特此将上述列出的专利文件中的全部内容并入本文作为参考。
在一个的实施例中,半导体发光体的发光波长范围从UV到近红外,较好的是从350nm到850nm,更好的是从380nm到800nm,最好的是从380nm到680nm。
在某些优先的实施例中,所述无机纳米发光体E选自发光纳米金属团簇。
一般的,金属纳米团簇包含有一个金属原子组成的核和一个在金属核周围的帽(Cap)。帽的作用是对核起保护,稳定作用,并能增加纳米团簇在各种溶剂中的溶解性。帽一般由有机材料材料组成。在某个优先的实施例中,帽可包含有巯基化合物(Thiols),如烷基硫醇,十八硫醇等,高聚物,树枝状聚合物,DNA寡核苷酸(DNA oligonucleotides),谷胱甘肽(Glutathione),肽(peptides)和蛋白质,及其衍生物。更优先的,帽可包含有树枝状聚合物,选自各种不同代的OH-封端的树枝状聚合物聚(酰氨基胺)PAMAM。此类树枝状聚合物有市售,如Aldrich公司。
按照本发明的电致发光器件中,金属纳米团簇的核小于4nm。在一个优先的实施例中,金属纳米团簇的核小于3nm,更好的是小于2nm,最好的是小于1nm。
在某些实施例中,金属纳米团簇的核的大小可以所包含的金属的原子数来衡量。一般地,金属原子数不大于200,较好的是不大于150,更好的是不大于100,最好的是不大于80。在一个优先的实施例中,金属纳米团簇的核所包含的金属的原子数是所谓的幻数(magic number),他们是2,8,20,28,50,82,126等。当金属纳米团簇的核所包含的金属的原子数是这些幻数时,它的稳定性较高。
金属纳米团簇的核可以包含任何金属元素。在一个优先的实施例中,金属纳米团簇的核的金属元素选自Au,Ag,Pt,Pd,Cu及它们的合金或任何组合。在一个更加优先的实施例中,金属纳米团簇的核的金属元素选自Au,Ag及它们的合金或任何组合。在一个最优先的实施例中,金属纳米团簇的核的金属元素选自Au或Ag。
各种金属纳米团簇的合成,表征方法,及性能在很多的综述中有详细的介绍,如Li Shang等,Nano Today(2011)6,401-418,Jie Zhang等,Annu.Rev.Phys.Chem.(2007)58,409-31,Marie-Christine Daniel & Didier Astruc,Chem.Rev.2004,104,293-346,Jun Yang等,Chem.Soc.Rev.2011,40,1672-1696。特此将上述列出的文献中的内容并入本文作为参考。
在某些实施例中,所述的金属纳米团簇的核是包含有两种不同的材料具有至少有一个外壳的核/壳(Core/Shell)结构的异质结构。具有核/壳结构的金属纳米团簇的例子和合成可参照Christopher J.Serpell等,Nat.Chem.3(2011),478,S.Mohan等,Appl.Phys.Lett. 91(2007),253107,Tetsu Yonezawa,Nanostructure Sci.Technol.(2006)251。
按照本发明的混合物,其中有机化合物H具有较高的消光系数。消光系数也称摩尔吸光系数(Molar Extinction Coefficient),是指浓度为1摩尔/升时的吸光系数,用符号ε表示,单位:Lmol
-1cm
-1,优选的消光系数:ε≥1*10
3;更优选的:ε≥1*10
4;特别优选的:ε≥5*10
4;最优选的:ε≥1*10
5。优选的,所述的消光系数是指在吸收峰对应的波长时的消光系数。
在某些实施例中,有机化合物H的吸收光谱在380nm-500nm之间。
在一些优选的实施例中,有机化合物H的发光光谱在440nm-500nm之间。
在一个优选的实施例中,有机化合物H的发光光谱的峰值对应的波长小于500nm。
在另一些优选的实施例中,有机化合物H的发光光谱在500nm-580nm之间。
在本发明中,对于有机材料的能级结构,三线态能级(T1)及单线态能级(S1)、HOMO、LUMO和谐振因子强度f对其光电性能及稳定性有着重要的影响。以下对这些参数的确定作一介绍。
HOMO和LUMO能级可以通过光电效应进行测量,例如XPS(X射线光电子光谱法)和UPS(紫外光电子能谱)或通过循环伏安法(以下简称CV)。最近,量子化学方法,例如密度泛函理论(以下简称DFT),也成为行之有效的计算分子轨道能级的方法。
有机材料的三线态能级T1可通过低温时间分辨发光光谱来测量,或通过量子模拟计算(如通过Time-dependent DFT)得到,如通过商业软件Gaussian 03W(Gaussian Inc.),具体的模拟方法如下面所述。
有机材料的单线态能级S1,可通过吸收光谱,或发射光谱来确定,也可通过量子模拟计算(如Time-dependent DFT)得到;谐振因子强度f也可通过量子模拟计算(如Time-dependent DFT)得到。
应该注意,HOMO、LUMO、T1及S1的绝对值取决于所用的测量方法或计算方法,甚至对于相同的方法,不同评价的方法,例如在CV曲线上起始点和峰点可给出不同的HOMO/LUMO值。因此,合理有意义的比较应该用相同的测量方法和相同的评价方法进行。本发明实施例的描述中,HOMO、LUMO、T1及S1的值是基于Time-dependent DFT的模拟,但不影响其他测量或计算方法的应用。
优先的,按照本发明的有机化合物H具有较大的(S1-T1),一般的(S1-T1)≥0.70eV,较好是≥0.80eV,更好是≥0.90eV,更更好是≥1.00eV,最好是≥1.10eV。
在一个优先的实施例中,有机化合物H具有较大的ΔHOMO和/或ΔLUMO,一般的≥0.50eV,较好是≥0.60eV,更好是≥0.70eV,更更好是≥0.80eV,最好是≥0.90eV;其中ΔHOMO=HOMO-(HOMO-1),ΔLUMO=(LUMO+1)-LUMO。
出于本发明的目的,(HOMO-1)定义为第二高的占有轨道能级,(HOMO-2)为第三高的占有轨道能级,以此类推。(LUMO+1)定义为第二低的未占有轨道能级,(LUMO+2)为第三低的占有轨道能级,以此类推;这些能级都可以通过下述的模拟方法确定。
在一个较为优先的实施例中,有机化合物H具有较大的谐振因子f(Sn)(n≥1);一般的f(S1)≥0.20eV,较好是≥0.30eV,更好是≥0.40eV,更更好是≥0.50eV,最好是≥0.60eV。
在某些实施例中,有机化合物H具有较低的HOMO,一般是≤-5.0eV,较好是≤-5.1eV,更好是≤-5.2eV,更更好是≤-5.3eV,最好是≤-5.4eV。
在另一些实施例中,有机化合物H具有较高的LUMO,一般是≥-3.0eV,较好是≥-2.9eV,更好是≥-2.8eV,更更好是≥-2.7eV,最好是-2.6eV。
合适的有机化合物H可以选自有机小分子,高分子,及金属配合物。
在某些优选的实施例中,所述的有机化合物H可选自含有环芳香烃化合物,如苯、联苯、三苯基、苯并、萘、蒽、萉、菲、芴、芘、屈、苝、薁;芳香杂环化合物,如二苯并噻吩、二苯并呋喃、二苯并硒吩、呋喃、噻吩、苯并呋喃、苯并噻吩、苯并硒吩、咔唑、吲哚咔唑、吡 啶吲哚、吡咯二吡啶、吡唑、咪唑、三氮唑、异恶唑、噻唑、恶二唑、恶三唑、二恶唑、噻二唑、吡啶、哒嗪、嘧啶、吡嗪、三嗪、恶嗪、恶噻嗪、恶二嗪、吲哚、苯并咪唑、吲唑、吲哚嗪、苯并恶唑、苯异恶唑、苯并噻唑、喹啉、异喹啉、噌啉、喹唑啉、喹喔啉、萘、酞、蝶啶、氧杂蒽、吖啶、吩嗪、吩噻嗪、吩恶嗪、苯并呋喃吡啶、呋喃二吡啶、苯并噻吩吡啶、噻吩二吡啶、苯并硒吩吡啶和硒吩二吡啶;包含有2至10环结构的基团,它们可以是相同或不同类型的环芳香烃基团或芳香杂环基团,并彼此直接或通过至少一个以下的基团连结在一起,如氧原子、氮原子、硫原子、硅原子、磷原子、硼原子、链结构单元和脂肪环基团。
在一个优先的实施例中,所述的有机化合物H可选于包含至少一个以下基团的化合物:
其中,Ar
1是芳基或杂芳基;X
1-X
8选于CR
1或N;X
9和X
10选于CR
1R
2或NR
1或O。
R
1和R
2分别独立选自H、D,或具有1至20个C原子的直链的烷基、卤代烷基、烷氧基、硫代烷氧基基团,或者具有3至20个C原子的支链或环状的烷基、卤代烷基、烷氧基、硫代烷氧基基团或者是甲硅烷基基团,或具有1至20个C原子的取代的酮基基团,或具有2至20个C原子的烷氧基羰基基团,或具有7至20个C原子的芳氧基羰基基团,氰基基团(-CN),氨基甲酰基基团(-C(=O)NH2),卤甲酰基基团(-C(=O)-X其中X代表卤素原子),甲酰基基团(-C(=O)-H),异氰基基团,异氰酸酯基团,硫氰酸酯基团或异硫氰酸酯基团,羟基基团,硝基基团,NO
2,CF
3基团,Cl,Br,F,I,可交联的基团或者具有5至40个环原子的取代或未取代的芳族或杂芳族环系,或具有5至40个环原子的芳氧基或杂芳氧基基团,或具有5至40个环原子的芳胺基或杂芳胺基基团,以上取代基任意位置的二取代单元或这些基团的组合,其中一个或多个取代基团可以彼此和/或与所述基团键合的环形成单环或多环的脂族或芳族环系。
在另一些实施例中,所述的有机化合物H选自具有较长的共轭π电子系统。迄今,已有许多例子,例如在JP2913116B和WO2001021729A1中公开的苯乙烯胺及其衍生物,和在WO2008/006449和WO2007/140847中公开的茚并芴及其衍生物。
在一个优先的实施例中,所述的有机化合物H可选自一元苯乙烯胺,二元苯乙烯胺,三元苯乙烯胺,四元苯乙烯胺,苯乙烯膦,苯乙烯醚和芳胺。
一个一元苯乙烯胺是指一化合物,它包含一个无取代或取代的苯乙烯基组和至少一个胺,最好是芳香胺。一个二元苯乙烯胺是指一化合物,它包含二个无取代或取代的苯乙烯基组和至少一个胺,最好是芳香胺。一个三元苯乙烯胺是指一化合物,它包含三个无取代或取代的苯乙烯基组和至少一个胺,最好是芳香胺。一个四元苯乙烯胺是指一化合物,它包含四个无取代或取代的苯乙烯基组和至少一个胺,最好是芳香胺。一个优选的苯乙烯是二苯乙烯,其可能会进一步被取代。相应的膦类和醚类的定义与胺类相似。芳基胺或芳香胺是指一种化合物,包含三个直接联接氮的无取代或取代的芳香环或杂环系统。这些芳香族或杂环的环系统中至少有一个优先选于稠环系统,并最好有至少14个芳香环原子。其中优选的例子有芳香蒽胺,芳香蒽二胺,芳香芘胺,芳香芘二胺,芳香屈胺和芳香屈二胺。一个芳香蒽胺是指一化合物,其中一个 二元芳基胺基团直接联到蒽上,最好是在9的位置上。一个芳香蒽二胺是指一化合物,其中二个二元芳基胺基团直接联到蒽上,最好是在9,10的位置上。芳香芘胺,芳香芘二胺,芳香屈胺和芳香屈二胺的定义类似,其中二元芳基胺基团最好联到芘的1或1,6位置上。
基于乙烯胺及芳胺的有机化合物H的例子,可在下述专利文件中找到:WO 2006/000388,WO 2006/058737,WO 2006/000389,WO 2007/065549,WO 2007/115610,US 7250532 B2,DE 102005058557 A1,CN 1583691 A,JP 08053397 A,US 6251531 B1,US 2006/210830 A,EP 1957606 A1和US 2008/0113101 A1。特此上述列出的专利文件中的全部内容并入本文作为参考。
基于均二苯乙烯极其衍生物的有机化合物H的例子有US 5121029。
进一步的优选的有机化合物H可选于茚并芴-胺和茚并芴-二胺,如WO 2006/122630所公开的,苯并茚并芴-胺和苯并茚并芴-二胺,如WO2008/006449所公开的,二苯并茚并芴-胺和二苯并茚并芴-二胺,如WO2007/140847所公开的。
其他可用作有机化合物H的材料有多环芳烃化合物,特别是如下化合物的衍生物:蒽如9,10-二(2-萘并蒽),萘,四苯,氧杂蒽,菲,芘(如2,5,8,11-四-t-丁基苝),茚并芘,苯撑如(4,4’-双(9-乙基-3-咔唑乙烯基)-1,1’-联苯),二茚并芘,十环烯,六苯并苯,芴,螺二芴,芳基芘(如US20060222886),亚芳香基乙烯(如US5121029,US5130603),环戊二烯如四苯基环戊二烯,红荧烯,香豆素,若丹明,喹吖啶酮,吡喃如4(二氰基亚甲基)-6-(4-对二甲氨基苯乙烯基-2-甲基)-4H-吡喃(DCM),噻喃,双(吖嗪基)亚胺硼化合物(US 2007/0092753 A1),双(吖嗪基)亚甲基化合物,carbostyryl化合物,噁嗪酮,苯并恶唑,苯并噻唑,苯并咪唑及吡咯并吡咯二酮。一些单重态发光体的材料可在下述专利文件中找到:US 20070252517 A1,US 4769292,US 6020078,US 2007/0252517 A1,US 2007/0252517 A1。特此将上述列出的专利文件中的全部内容并入本文作为参考。
以上出现的有机功能材料出版物为公开的目的以参考方式并入本申请。
在一个优先的实施例中,所述的有机化合物H包含至少一个醇溶性或水溶性基团;较好是包含至少两个醇溶性或水溶性基团,最好是包含至少三个醇溶性或水溶性基团。
在另一些实施例中,所述的有机化合物H包含至少一个可交联基团;较好是包含至少两个可交联基团;最好是包含至少三个可交联基团。
在下面列出一些合适的有机化合物H的例子(但不限于),其可进一步被任意取代:
在一个较为优先的实施例中,所述的有机化合物H的发光谱的半峰宽(FWHM)≤70nm,较好是≤60nm,更好是≤50nm,特别好是≤40nm,最好是≤35nm。
在另一个优先的实施例中,所述的有机化合物H是具有如下的结构式的化合物(氟硼吡咯(Bodipy)的衍生物):
其中:X为CR
47或N;R
41-R
49各自独立地选自氢、烷基、环烷基、杂环基、链烯基、环烯基、炔基、羟基、巯基、烷氧基、烷基硫基、芳基醚基、芳基硫醚基、芳基、杂芳基、卤素、氰基、醛基、羰基、羧基、氧基羧基、氨基甲酰基、氨基、硝基、甲硅烷基、硅氧烷基、硼烷基、氧化麟基,R
41-R
49可与相邻取代基之间形成稠环及脂肪族环。
在一个优选的实施例中,R
49和R
48独立选自吸电子基团。合适的吸电子基团包括但不限于:F,Cl,氰基,部分或全氟化的烷基链,或如下基团中的一种:
其中,m为1、2或3;X
1-X
8选于CR
4或N,并且至少有一个是N;M
1、M
2、M
3分别独立表示N(R
4)、C(R
4R
5)、Si(R
4R
5)、O、C=N(R
4)、C=C(R
4R
5)、P(R
4)、P(=O)R
4、S、S=O、SO
2或无;R
4、R
5的含义同上述R
1所示。
合适的Bodipy的衍生物的例子有,但不限于,
在另一个优先的实施例中,所述的有机化合物H包含有化学式(1)或(2)所示的结构单元,
其中使用的符号与标记具有以下含义:Ar
1-Ar
3相同或不同的选自具有5-24个环原子的芳香族或杂芳香族;Ar
4-Ar
5相同或不同的选自空或具有5-24个环原子的芳香族或杂芳香族;当Ar
4-Ar
5不为空时,X
a,X
b选自N、C(R
9)、Si(R
9);Y
a,Y
b选自B、P=O、C(R
9)、Si(R
9);当Ar
4-Ar
5为空时,Y
a选自B、P=O、C(R
9)、Si(R
9);X
b选自N、C(R
9)、Si(R
9);X
a或Y
b选自N(R
9)、C(R
9R
10)、Si(R
9R
10)、C=O、O、C=N(R
9)、C=C(R
9R
10)、P(R
9)、P(=O)R
9、S、S=O或SO
2;X
1、X
2是空或一个桥接基团;R
4-R
10含义同上述R
1。
在一个较为优先的实施例中,R
1-R
10分别独立选自H、D,具有1至10个C原子的直链烷基、烷氧基或硫代烷氧基基团,或者具有3至10个C原子的支链或环状的烷基、烷氧基或硫代烷氧基基团或者是甲硅烷基基团,或具有1至10个C原子的取代的酮基基团,或具有2至10个C原子的烷氧基羰基基团,或具有7至10个C原子的芳氧基羰基基团,氰基基团(-CN),氨基甲酰基基团(-C(=O)NH
2),卤甲酰基基团(-C(=O)-X其中X代表卤素原子),甲酰基基团(-C(=O)-H),异氰基基团,异氰酸酯基团,硫氰酸酯基团或异硫氰酸酯基团,羟基基团,硝基基团,CF
3基团,Cl,Br,F,可交联的基团或者具有5至20个环原子的取代或未取代的芳族或杂芳族环系,或具有5至20个环原子的芳氧基或杂芳氧基基团,或这些基团的组合,其中一个或多个基团可以彼此和/或与所述基团键合的环形成单环或多环的脂族或芳族环系。
按照化学式(1)或(2)的有机化合物H的优选方案可以参考与本发明同期申报的三个中国专利申请,其申请号分别为CN202110370910.9,CNCN202110370866.1,CN202110370884.X。特将以上专利文件中的全部内容并入本文作为参考。
按照本发明的混合物,所述无机纳米发光体E的吸收光谱光谱和有机化合物H的发射光谱都有较大的重叠,相互之间可以实现较为高效的能量转移(
resonance energy transfer(FRET))。
在某些优先的实施例中,所述的混合物,其发光光谱完全来自无机纳米发光体E,即无机纳米发光体E和有机化合物H之间实现完全的能量转移。
在某些实施例中,所述的混合物包含2种以上的有机化合物H。
在一个优选的实施例中,所述的混合物中,所述的有机化合物H和无机纳米发光体E重量比为从50:50到99:1,较好是从60:40到98:2,更好是从70:30到97:3,最好是从80:20到95:5。
在一种特别优先的实施例中,所述的混合物还包含一种有机树脂。出于本发明的目的,所述的有机树脂是指树脂预聚体或其交联或固化后形成的树脂。
在一个优先的实施例中,所述的混合物包含两种及以上的有机树脂。
适合本发明的有机树脂,包括但不限制于:聚苯乙烯、聚丙烯酸酯、聚甲基丙烯酸酯、聚碳酸酯、聚胺酯、聚乙烯吡咯烷酮、聚乙酸乙烯酯、聚氯乙烯、聚丁烯、聚乙二醇、聚硅氧烷、聚丙烯酸酯、环氧树脂、聚乙烯醇、聚丙烯腈、聚偏二氯乙烯(PVDC)、聚苯乙烯-丙烯腈(SAN)、聚对苯二甲酸丁二醇酯(PBT)、聚对苯二甲酸乙二醇酯(PET)、聚丁酸乙烯酯(PVB)、聚氯乙烯(PVC)、聚酰胺、聚甲醛、聚酰亚胺、聚醚酰亚胺或其混合物。
进一步,适合本发明的有机树脂,包含但不限制于由以下单体(树脂预聚体)均聚或共聚形成:苯乙烯衍生物、丙烯酸酯衍生物、丙烯腈衍生物、丙烯酰胺衍生物、乙烯酯衍生物、乙 烯醚衍生物、马来酰亚胺衍生物、共轭二烯烃衍生物。
苯乙烯衍生物的例子有:烷基苯乙烯,如α-甲基苯乙烯,邻-、间-、对-甲基苯乙烯,对丁基苯乙烯,尤其是对叔丁基苯乙烯,烷氧基苯乙烯如对甲氧基苯乙烯、对丁氧基苯乙烯、对叔丁氧基苯乙烯。
丙烯酸酯衍生物的例子有:丙烯酸甲酯、甲基丙烯酸甲酯、丙烯酸乙酯、甲基丙烯酸乙酯、丙烯酸正丙酯、甲基丙烯酸正丙酯、丙烯酸异丙酯、甲基丙烯酸异丙酯、丙烯酸正丁酯、甲基丙烯酸正丁酯、丙烯酸异丁酯、甲基丙烯酸异丁酯、丙烯酸仲丁酯、甲基丙烯酸仲丁酯、丙烯酸叔丁酯、甲基丙烯酸叔丁酯、丙烯酸2-羟基乙酯、甲基丙烯酸2-羟基乙酯、丙烯酸2-羟基丙酯、甲基丙烯酸2-羟基丙酯、丙烯酸3-羟基丙酯、甲基丙烯酸3-羟基丙酯、丙烯酸2-羟基丁酯、甲基丙烯酸2-羟基丁酯、丙烯酸3-羟基丁酯、甲基丙烯酸3-羟基丁酯、丙烯酸4-羟基丁酯、甲基丙烯酸4-羟基丁酯、丙烯酸烯丙酯、甲基丙烯酸烯丙酯、丙烯酸苄酯、甲基丙烯酸苄酯、丙烯酸环己酯、甲基丙烯酸环己酯、丙烯酸苯酯、甲基丙烯酸苯酯、丙烯酸2-甲氧基乙酯、甲基丙烯酸2-甲氧基乙酯、丙烯酸2-苯氧基乙酯、甲基丙烯酸2-苯氧基乙酯、甲氧基二甘醇丙烯酸酯、甲氧基二甘醇甲基丙烯酸酯、甲氧基三甘醇丙烯酸酯、甲氧基三甘醇甲基丙烯酸酯、甲氧基丙二醇丙烯酸酯、甲氧基丙二醇甲基丙烯酸酯、甲氧基二丙二醇丙烯酸酯、甲氧基二丙二醇甲基丙烯酸酯、丙烯酸异冰片酯、甲基丙烯酸异冰片酯、丙烯酸双环戊二烯酯、甲基丙烯酸双环戊二烯酯、(甲基)丙烯酸金刚烷酯、(甲基)丙烯酸降冰片酯、丙烯酸2-羟基-3-苯氧基丙酯、甲基丙烯酸2-羟基-3-苯氧基丙酯、单丙烯酸甘油酯和单甲基丙烯酸甘油酯;丙烯酸2-氨基乙酯、甲基丙烯酸2-氨基乙酯、丙烯酸2-二甲基氨基乙酯、甲基丙烯酸2-二甲基氨基乙酯、N,N-二甲基氨基乙基(甲基)丙烯酸、N,N-二乙基氨基乙基(甲基)丙烯酸酯、丙烯酸2-氨基丙酯、甲基丙烯酸2-氨基丙酯、丙烯酸2-二甲基氨基丙酯、甲基丙烯酸2-二甲基氨基丙酯、丙烯酸3-氨基丙酯、甲基丙烯酸3-氨基丙酯、N,N-二甲基-1,3-丙二胺(甲基)丙烯酸苄酯、丙烯酸3-二甲基氨基丙酯和甲基丙烯酸3-二甲基氨基丙酯;丙烯酸缩水甘油酯和甲基丙烯酸缩水甘油酯。
丙烯腈衍生物的例子有:丙烯腈、甲基丙烯腈、α-氯丙烯腈和偏二氰基乙烯。
丙烯酰胺衍生物的例子有:丙烯酰胺、甲基丙烯酰胺、α-氯丙烯酰胺、N-2-羟乙基丙烯酰胺和N-2-羟乙基甲基丙烯酰胺。
乙烯酯衍生物的例子有:乙酸乙烯酯、丙酸乙烯酯、丁酸乙烯酯和苯甲酸乙烯酯。
乙烯醚衍生物的例子有:乙烯基甲基醚、乙烯基乙基醚和烯丙基缩水甘油基醚。
马来酰亚胺衍生物的例子有:马来酰亚胺、苄基马来酰亚胺、N-苯基马来酰亚胺和N-环己基马来酰亚胺。
共轭二烯烃衍生物的例子有:1,3-丁二烯、异戊二烯和氯丁二烯。
所述的均聚物或共聚物可以通过例如自由基聚合、阳离子聚合、阴离子聚合或有机金属催化聚合(例如Ziegler-Natta催化)进行制备。聚合的工艺可以是悬浮聚合、乳液聚合、溶液聚合或本体聚合。
所述的有机树脂通常具有10 000-1 000 000g/mol,优选20 000-750 000g/mol,更优选30 000-500 000g/mol的平均摩尔质量Mn(由GPC测定)。
在一些优先的实施例中,有机树脂为热固性树脂或紫外(UV)可固化树脂。在一些实施例中,用将促进卷对卷加工的方法固化有机树脂。
热固性树脂需要固化,在固化中它们会经历不可逆的分子交联过程,这使得树脂不可熔化。在一些实施例中,热固性树脂为环氧树脂、酚醛树脂、乙烯基树脂、三聚氰胺树脂、脲醛树脂、不饱和聚酯树脂、聚氨酯树脂、烯丙基树脂、丙烯酸类树脂、聚酰胺树脂、聚酰胺-酰亚胺树脂、酚胺缩聚树脂、脲三聚氰胺缩聚树脂或其组合。
在一些实施例中,热固性树脂为环氧树脂。环氧树脂易于固化,不会放出挥发物或因广泛 的化学品而生成副产物。环氧树脂也可与大多数基板相容并往往易于润湿表面。参见Boyle,M.A.等人,“Epoxy Resins”,Composites,Vol.21,ASM Handbook,pages 78-89(2001)。
在一些实施例中,有机树脂为有机硅热固性树脂。在一些实施例中,有机硅热固性树脂为0E6630A或0E6630B(Dow Corning Corporation(密歇根州奥本市))。
在一些实施例中,使用热引发剂。在一些实施例中,热引发剂为AIBN[2,2’-偶氮双(2-甲基丙腈)]或过氧化苯甲酰。
UV可固化树脂是在暴露于特定波长的光时将固化并快速硬化的聚合物。在一些实施例中,UV可固化树脂为具有自由基聚合基团、阳离子可聚合基团作为官能团的树脂,所述自由基聚合基团为例如(甲基)丙烯酰氧基基团、乙烯基氧基基团、苯乙烯基基团或乙烯基基团;所述阳离子可聚合基团为例如环氧基基团、硫代环氧基基团、乙烯基氧基基团或氧杂环丁烷基基团。在一些实施例中,UV可固化树脂为聚酯树脂、聚醚树脂、(甲基)丙烯酸类树脂、环氧树脂、聚氨酯树脂、醇酸树脂、螺缩醛树脂、聚丁二烯树脂或硫代烯树脂。
在一些实施例中,UV可固化树脂选自聚氨酯丙烯酸酯、烯丙氧基化的二丙烯酸环己酯、双(丙烯酰氧基乙基)羟基异氰脲酸酯、双(丙烯酰氧基新戊基二醇)己二酸酯、双酚A二丙烯酸酯、双酚A二甲基丙烯酸酯、1,4-丁二醇二丙烯酸酯、1,4-丁二醇二甲基丙烯酸酯、1,3-丁二醇二丙烯酸酯、1,3-丁二醇二甲基丙烯酸酯、二环戊基二丙烯酸酯、二乙二醇二丙烯酸酯、二乙二醇二甲基丙烯酸酯、二季戊四醇六丙烯酸酯、二季戊四醇单羟基五丙烯酸酯、二(三羟甲基丙烷)四丙烯酸酯、三乙二醇二甲基丙烯酸酯、甲基丙烯酸甘油酯、1,6-己二醇二丙烯酸酯、新戊二醇二甲基丙烯酸酯、新戊二醇羟基新戊酸二丙烯酸酯、季戊四醇三丙烯酸酯、季戊四醇四丙烯酸酯、磷酸二甲基丙烯酸酯、聚乙二醇二丙烯酸酯、聚丙二醇二丙烯酸酯、四乙二醇二丙烯酸酯、四溴双酚A二丙烯酸酯、三乙二醇二乙烯基醚、二丙烯酸三甘油酯、三羟甲基丙烷三丙烯酸酯、三丙二醇二丙烯酸酯、三(丙烯酰氧基乙基)异氰脲酸酯、磷酸三丙烯酸酯、磷酸二丙烯酸酯、丙烯酸焕丙基酯、乙烯基封端聚二甲基硅氧烷、乙烯基封端二苯基硅氧烷-二甲基硅氧烷共聚物、乙烯基封端聚苯基甲基硅氧烷、乙烯基封端二氟甲基硅氧烷-二甲基硅氧烷共聚物、乙烯基封端二乙基硅氧烷-二甲基硅氧烷共聚物、乙烯基甲基硅氧烷、单甲基丙烯酰氧基丙基封端聚二甲基硅氧烷、单乙烯基封端聚二甲基硅氧烷、单烯丙基-单三甲基甲硅烷氧基封端聚环氧乙烷及其组合。
在一些实施例中,UV可固化树脂为巯基官能化合物,其可在UV固化条件下与异氰酸酯、环氧树脂或不饱和化合物交联。在一些实施例中,巯基官能化合物为多硫醇。在一些实施例中,多硫醇为季戊四醇四(3-巯基丙酸酯)(PETMP);三羟甲基丙烷三(3-巯基丙酸酯)(TMPMP);乙二醇二(3-巯基丙酸酯)(GDMP);三[25-(3-巯基-丙酰氧基)乙基]异氰尿酸酯(TEMPIC);二季戊四醇六(3-巯基丙酸酯)(Di-PETMP);乙氧基化三羟甲基丙烷三(3-巯基丙酸酯)(ETTMP 1300和ETTMP 700);聚己内酯四(3-巯基丙酸酯)(PCL4MP1350);季戊四醇四巯基乙酸酯(PETMA);三羟甲基丙烷三巯基乙酸酯(TMPMA);或乙二醇二巯基乙酸酯(GDMA)。这些化合物由Bruno Bock(德国马尔沙赫特)以商品名
出售。
在一些实施例中,UV可固化树脂还包含光引发剂。光引发剂将在暴露于光的过程中引发光敏材料的交联和/或固化反应。在一些实施例中,光引发剂是基于苯乙酮的、基于安息香的或基于噻吨酮的。
在一些实施例中,UV可固化树脂包含巯基官能化合物和甲基丙烯酸酯、丙烯酸酯、异氰酸酯或其组合。在一些实施例中,UV可固化树脂包括多硫醇和甲基丙烯酸酯、丙烯酸酯、异氰酸酯或其组合。
在一些实施例中,光引发剂为MINS-311RM(Minuta Technology Co.,Ltd(韩国))。
在一些实施例中,光引发剂为
127、
184、
184D、
2022、
2100、
250、
270、
2959、
369、
369EG、
379、
500、
651、
754、
784、
819、
819DW、
907、
907FF、
OxeOl、
TPO-L、
1173、
1173D、
4265,
BP或
MBF(BASF Corporation(密歇根州怀恩多特))。
在一些实施例中,光引发剂为TPO(2,4,6-三甲基苯甲酰-二苯基-氧化麟)或MBF(苯甲酰甲酸甲酯)。
在一些实施例中,有机树脂按组合物的重量百分数(重量/重量)计在约20%至约99%、约20%至约95%、约20%至约90%、约20%至约85%、约20%至约80%、约20%至约70%、约20%至约60%、约40%至约99%、约40%至约95%、约40%至约90%、约40%至约85%、约40%至约80%、约40%至约70%、约70%至约99%、约70%至约95%、约70%至约90%、约70%至约85%、约70%至约80%、约80%至约99%、约80%至约95%、约80%至约90%、约80%至约85%、约85%至约99%、约85%至约95%、约85%至约90%、约90%至约99%、约90%至约95%、或约95%至约99%之间。
本发明还涉及一种组合物,包含一种如上所述的混合物,和至少一种溶剂。
在一个优选的实施例中,按照本发明的组合物是一溶液。
在另一个优选的实施例中,按照本发明的组合物是一悬浮液。
本发明实施例中的组合物中可以包括0.01至20wt%的无机纳米发光体E,较好的是0.1至30wt%,更好的是0.2至20wt%,最好的是2至15wt%的无机纳米发光体E。
按照本发明的组合物,可以使用喷墨打印、转印、光刻等方法来形成颜色转换层,此时,需将所述的化合物(即颜色转换材料)单独或与其他材料一起溶解在树脂(预聚体)和/或有机溶剂中,形成油墨。本发明所述的化合物(即颜色转换材料)在油墨中的质量浓度不低于0.1%wt。可以通过调节油墨中颜色转换材料的浓度和颜色转换层的厚度来改善颜色转换层的颜色转换能力。一般而言,颜色转换材料的浓度越高或厚度越厚,颜色转换层的颜色转换率越高。
在一些优先的实施例中,所述的溶剂选自水,醇,酯、芳族酮或芳族醚、脂肪族酮或脂肪族醚、或硼酸酯或磷酸酯等无机酯类化合物,或两种及两种以上溶剂的混合物。
在另一些实施例中,适当的和优选的溶剂是脂肪族、脂环族或芳烃族,胺,硫醇,酰胺,腈,酯,醚,聚醚,醇,二醇或多元醇。
在另一些实施例中,醇代表适当类别的溶剂。优选的醇包括烷基环己醇,特别是甲基化的脂肪族醇,萘酚等。
另外适当的醇类溶剂的例子有:十二醇,苯基十三醇,苯甲醇,乙二醇,乙二醇甲醚,丙三醇,丙二醇,丙二醇乙醚等。
所述的溶剂可以是单独使用,也可以是作为两种或多种有机溶剂的混合物使用。
进一步,有机溶剂的例子,包括(但不限于):甲醇、乙醇、2-甲氧基乙醇、二氯甲烷、三氯甲烷、氯苯、邻二氯苯、四氢呋喃、苯甲醚、吗啉、甲苯、邻二甲苯、间二甲苯、对二甲苯、1,4二氧杂环己烷、丙酮、甲基乙基酮、1,2二氯乙烷、3-苯氧基甲苯、1,1,1-三氯乙烷、1,1,2,2-四氯乙烷、醋酸乙酯、醋酸丁酯、二甲基甲酰胺、二甲基乙酰胺、二甲基亚砜、四氢萘、萘烷、茚和/或它们的混合物。
在一些优先的实施例中,按照本发明的一种组合物,其中所述的有机溶剂选自芳族或杂芳族、酯、芳族酮或芳族醚、脂肪族酮或脂肪族醚、脂环族或烯烃类化合物,或硼酸酯或磷酸酯等无机酯类化合物,或两种及两种以上溶剂的混合物。
按照本发明的基于芳族或杂芳族溶剂的例子有,但不限于:1-四氢萘酮、3-苯氧基甲苯、苯乙酮、1-甲氧基萘、对二异丙基苯、戊苯、四氢萘、环己基苯、氯萘、1,4-二甲基萘、3-异丙基联苯、对甲基异丙苯、二戊苯、邻二乙苯、间二乙苯、对二乙苯、1,2,3,4-四甲苯、1,2,3,5- 四甲苯、1,2,4,5-四甲苯、丁苯、十二烷基苯、1-甲基萘、1,2,4-三氯苯、1,3-二丙氧基苯、4,4-二氟二苯甲烷、二苯醚、1,2-二甲氧基-4-(1-丙烯基)苯、二苯甲烷、2-苯基吡啶、3-苯基吡啶、2-苯氧基甲醚、2-苯氧基四氢呋喃、乙基-2-萘基醚、N-甲基二苯胺、4-异丙基联苯、α,α--二氯二苯甲烷、4-(3-苯基丙基)吡啶、苯甲酸苄酯、1,1-双(3,4-二甲基苯基)乙烷、2-异丙基萘、二苄醚等。
在另一些实施例中,适当的和优选的溶剂是脂肪族、脂环族或芳烃族,胺,硫醇,酰胺,腈,酯,醚,聚醚。
所述的溶剂可以是环烷烃,例如十氢化萘。
在另一些优先的实施例中,按照本发明的一种组合物,其中包含至少50wt%的醇类溶剂;优选至少80wt%的醇类溶剂;特别优选至少90wt%的醇类溶剂。
一些优选的实施例中,特别适合本发明的溶剂是汉森(Hansen)溶解度参数在以下范围内的溶剂:
δ
d(色散力)在17.0-23.2MPa
1/2的范围,尤其是在18.5-21.0MPa
1/2的范围。
δ
p(极性力)在0.2-12.5MPa
1/2的范围,尤其是在2.0-6.0MPa
1/2的范围。
δ
h(氢键力)在0.9-14.2MPa
1/2的范围,尤其是在2.0-6.0MPa
1/2的范围。
按照本发明的组合物,其中有机溶剂在选取时需考虑其沸点参数。本发明中,所述的有机溶剂的沸点≥150℃;优选为≥180℃;较优选为≥200℃;更优选为≥250℃;最优选为≥275℃或≥300℃。这些范围内的沸点对防止喷墨印刷头的喷嘴堵塞是有益的。所述的有机溶剂可从溶剂体系中蒸发,以形成包含功能材料薄膜。
在一些优先的实施例中,按照本发明的组合物,1)其粘度@25℃,在1cPs到100cPs范围,和/或2)其表面张力@25℃,在19dyne/cm到50dyne/cm范围。
按照本发明的组合物,其中树脂(预聚体)或有机溶剂在选取时需考虑其表面张力参数。合适的表面张力参数适合于特定的基板和特定的印刷方法。例如对喷墨印刷,在一个优选的实施例中,所述的树脂(预聚体)或有机溶剂在25℃下的表面张力约在19dyne/cm到50dyne/cm范围;更优为在22dyne/cm到35dyne/cm范围;最优为在25dyne/cm到33dyne/cm范围。
在一个优选的实施例中,按照本发明的组合物在25℃下的表面张力约在19dyne/cm到50dyne/cm范围;更好是在22dyne/cm到35dyne/cm范围;最好是在25dyne/cm到33dyne/cm范围。
按照本发明的组合物,其中树脂(预聚体)或有机溶剂在选取时需考虑其油墨的粘度参数。粘度可以通过不同的方法调节,如通过合适的树脂(预聚体)或有机溶剂的选取和油墨中功能材料的浓度。在一个优选的实施例中,所述的树脂(预聚体)或有机溶剂的粘度低于100cps;更优为低于50cps;最优为1.5到20cps。这里的粘度是指在印刷时的环境温度下的粘度,一般在15-30℃,较好的是18-28℃,更好的是20-25℃,最好的是23-25℃。如此配制的组合物将特别适合于喷墨印刷。
在一个优选的实施例中,按照本发明的组合物,在25℃下的粘度约在1cps到100cps范围;更好是在1cps到50cps范围;最好是在1.5cps到20cps范围。
满足上述沸点及表面张力参数及粘度参数的树脂(预聚体)或有机溶剂获得的油墨能够形成具有均匀厚度及组成性质的功能材料薄膜。
本发明进一步涉及一种有机功能材料薄膜,所述的有机功能材料薄膜利用一种如上所述的组合物制备而成。
本发明还提供一种所述的有机功能材料薄膜的制备方法,包含如下步骤:
1)制备一种按照本发明所述的混合物或组合物;
2)用印刷或涂布的方法将所述的组合物涂布于一基板上形成一薄膜,其中印刷或涂布的方法选于喷墨打印,喷印(Nozzle Printing),活版印刷,丝网印刷,浸涂,旋转涂布,刮刀 涂布,辊筒印花,扭转辊印刷,平版印刷,柔版印刷,轮转印刷,喷涂,刷涂或移印,狭缝型挤压式涂布;
3)将所得的薄膜在至少50℃加热或加上紫外光照,使之发生交联反应,固化薄膜。
所述的有机功能材料薄膜厚度一般为50nm-200mm,较好为100nm-150mm,更好为500nm-100mm,更更好为1mm-50mm,最好为1mm-20mm。
本发明还提供上述混合物及有机功能材料薄膜在光电器件中的应用。
在某些实施例中,所述光电器件可选于有机发光二极管(OLED)、有机光伏电池(OPV)、有机发光电池(OLEEC)、有机发光场效应管、有机激光器。
更进一步,本发明提供一种光电器件,包含一种上述的混合物或有机功能材料薄膜。
优先的,所述的光电器件是电致发光器件,如有机发光二极管(OLED)、有机发光电池(OLEEC)、有机发光场效应管、钙钛矿发光二极管(PeLED)、及量子点发光二极管(QD-LED),其中一功能层中包含一种上述的有机功能材料薄膜。所述的功能层可以选自空穴注入层,空穴传输层,电子注入层,电子传输层,发光层,及阴极钝化层(CPL)。
在一个优先的实施例中,所述的光电器件是电致发光器件,包含两个电极,其特征在于,所述的功能层位于所述的两个电极的同一侧。
在另一个优先的实施例中,所述的光电器件包含一发光单元和一颜色转换层(功能层),其中所述的颜色转换层包含一种上述的混合物或有机功能材料薄膜。
在一个优先的实施例中,所述的颜色转换层吸收掉95%及以上,较好是97%及以上,更好是99%及以上,最好是99.9%及以上发光单元的光。
在某些优先的实施例中,所述的发光单元选自固体发光器件。所述的固体发光器件优先选自LED、机发光二极管(OLED)、有机发光电池(OLEEC)、有机发光场效应管、钙钛矿发光二极管(PeLED)、量子点发光二极管(QD-LED)及纳米棒LED(nanorod LED,参见DOI:10.1038/srep28312)。
在一个优先的实施例中,所述的发光单元发射蓝光,通过颜色转换层转换成绿光或红光。
本发明进一步涉及一种显示器,包含至少红绿蓝三种像素,如附图1所示,蓝光像素包好一个蓝光发光单元,红绿光像素包含一蓝光发光单元和相应的红绿颜色转换层。
本发明进一步涉及一种有机电致发光器件,自下而上依次包含一基板、第一电极、一有机发光层、第二电极、一颜色转换层及一封装层,第二电极至少是部分透明,1)所述的颜色转换层包含一种有机化合物H和一种无机纳米发光体E;2)所述的颜色转换层至少部分吸收以上有机发光层所发的透过第二电极的光;3)所述有机化合物H的发光谱在所述无机纳米发光体E的吸收谱的短波长的一侧,且至少部分相互重叠;4)所述的无机纳米发光体E的发光谱的半峰宽(FWHM)小于或等于45nm。
所述的有机化合物H和无机纳米发光体E及其优选实施例如上所述。
在一个优选的实施例中,所述的颜色转换层进一步包含一树脂或树脂预聚体。合适及优选的树脂或树脂预聚体如上所述。
在一个优先的实施例中,目标是得到多色的光,所述的颜色转换层能吸收30%及以上,较好是40%及以上,最好是45%及以上有机发光层所发的透过第二电极的光。
在另一个优先的实施例中,目标是得到单色的光,所述的颜色转换层能吸收90%及以上,较好是95%及以上,更好是99%及以上,最好是99.9%及以上有机发光层所发的透过第二电极的光。
在某些实施例中,所述的颜色转换层的厚度在100nm-5μm之间,较好是在150nm-4μm之间,更好是在200nm-3μm之间,最好是在200nm-2μm之间。
在一个优先的实施例中,所述的有机电致发光器件是OLED。更优先的,第一电极时阳极,第二电极是阴极。特别优先的,所述的有机电致发光器件是顶发射(Top Emission)OLED。
基片可以是不透明或透明。一个透明的基板可以用来制造一个透明的发光元器件。例如可参见,Bulovic等Nature 1996,380,p29,和Gu等,Appl.Phys.Lett.1996,68,p2606。基片可以是刚性的或弹性的。基片可以是塑料,金属,半导体晶片或玻璃。最好是基片有一个平滑的表面。无表面缺陷的基板是特别理想的选择。在一个优选的实施例中,基片是柔性的,可选于聚合物薄膜或塑料,其玻璃化温度Tg为150℃以上,较好是超过200℃,更好是超过250℃,最好是超过300℃。合适的柔性基板的例子有聚(对苯二甲酸乙二醇酯)(PET)和聚乙二醇(2,6-萘)(PEN)。
阳极可包括一导电金属或金属氧化物,或导电聚合物。阳极可以容易地注入空穴到空穴注入层(HIL)或空穴传输层(HTL)或发光层中。在一个优先的实施例中,阳极的功函数和发光层中的发光体或作为HIL或HTL或电子阻挡层(EBL)的p型半导体材料的HOMO能级或价带能级的差的绝对值小于0.5eV,较好是小于0.3eV,最好是小于0.2eV。阳极材料的例子包括但不限于:Al、Cu、Au、Ag、Mg、Fe、Co、Ni、Mn、Pd、Pt、ITO、铝掺杂氧化锌(AZO)等。其他合适的阳极材料是已知的,本领域普通技术人员可容易地选择使用。阳极材料可以使用任何合适的技术沉积,如一合适的物理气相沉积法,包括射频磁控溅射,真空热蒸发,电子束(e-beam)等。在某些实施例中,阳极是图案结构化的。图案化的ITO导电基板可在市场上买到,并且可以用来制备根据本发明的器件。
阴极可包括一导电金属或金属氧化物。阴极可以容易地注入电子到EIL或ETL或直接到发光层中。在一个优先的实施例中,阴极的功函数和发光层中发光体或作为电子注入层(EIL)或电子传输层(ETL)或空穴阻挡层(HBL)的n型半导体材料的LUMO能级或导带能级的差的绝对值小于0.5eV,较好是小于0.3eV,最好是小于0.2eV。原则上,所有可用作OLED的阴极的材料都可能作为本发明器件的阴极材料。阴极材料的例子包括但不限于:Al、Au、Ag、Ca、Ba、Mg、LiF/Al、MgAg合金、BaF
2/Al、Cu、Fe、Co、Ni、Mn、Pd、Pt、ITO等。阴极材料可以使用任何合适的技术沉积,如一合适的物理气相沉积法,包括射频磁控溅射,真空热蒸发,电子束(e-beam)等。在一个优先的实施例中,所述的阴极在400nm-680nm范围的透光度≥40%,较好是≥45%,更好是≥50%,最好是≥60%。通常10-20nm的Mg:Ag合金可以用来做半透明阴极,Mg:Ag的比例可以从2:8到0.5:9.5。
所述有机电致发光器件中,发光层优选包含一蓝光荧光主体和一蓝光荧光客体;在另一个优选的实施例中,发光层包含一蓝光磷光主体和一蓝光磷光客体;OLED还可以包含其他功能层,如空穴注入层(HIL)、空穴传输层(HTL)、电子阻挡层(EBL)、电子注入层(EIL)、电子传输层(ETL)、空穴阻挡层(HBL)。适合用于这些功能层中的材料在上面及在WO2010135519A1、US20090134784A1和WO2011110277A1中有详细的描述,特此将此3篇专利文件中的全部内容并入本文作为参考。
进一步,所述有机电致发光器件还包括一个阴极覆盖层(Capping layer,简称CPL)。
在一个优先的实施例中,所述的CPL位于第二电极和所述的颜色转换层之间。
在另一个优先的实施例中,所述的CPL位于所述的颜色转换层之上。
用于CPL的材料一般需要有较高的折射率n,如n≥1.95@460nm,n≥1.90@520nm,n≥1.85@620nm。用于CPL材料的例子有:
更多的进一步的CPL材料的例子可以在如下的专利文献中找到:KR20140128653A,KR20140137231A,KR20140142021A,KR20140142923A,KR20140143618A,KR20140145370A,KR20150004099A,KR20150012835A,US9496520B2,US2015069350A1,CN103828485B,CN104380842B,CN105576143A,TW201506128A,CN103996794A,CN103996795A,CN104744450A,CN104752619A,CN101944570A,US2016308162A1,US9095033B2,US2014034942A1,WO2017014357A1;特将以上专利文献并入此文作为参考。
在一个较为优选的实施例中,颜色转换层中包含一种上述的CPL材料。
优先的,上述的有机电致发光器件,其中所述的封装层薄膜封装(TFE)。
本发明还涉及一显示面板,其中至少有一个像素包含上述的有机电致发光器件。
下面将结合优选实施例对本发明进行了说明,但本发明并不局限于下述实施例,应当理解,所附权利要求概括了本发明的范围在本发明构思的引导下本领域的技术人员应意识到,对本发明的各实施例所进行的一定的改变,都将被本发明的权利要求书的精神和范围所覆盖。
具体实施例:
作为主体材料的有机化合物H为H1-H14所示的结构:
主体材料H1-H14合成按照在申请号为CN202110370887.3的同期专利申请中所公开的。
一种绿色量子点QD1作为绿色发光体E,购自合肥福纳科技有限公司。
实施例1:包含聚合物的组合物及有机功能材料薄膜的制备
分别称取100mg聚甲基丙烯酸甲酯(PMMA)、50mg颜色转换主体材料(H1-H14)、5mg无机纳米发光体E,即绿色量子点QD1,然后将以上物质一起溶解在1ml乙酸正丁酯中,得到澄清溶液,即组合物或印刷油墨。使用KW-4a匀胶机,在石英玻璃表面旋涂以上溶液,形成厚度均匀的薄膜,得有机功能材料薄膜,即颜色转换薄膜。以上所得的颜色转换薄膜在大多的厚度小于6μm时,其光密度(Optical Density,即OD)可达到≥3。
实施例2:包含树脂预聚体的组合物及有机功能材料薄膜的制备
上述的颜色转换主体材料(H1-H14)和绿色量子点QD1也可以和树脂预聚体,如甲基丙烯酸甲酯,苯乙烯或甲基苯乙烯的组合物预混,在加1-5wt%的光引发剂,如TPO(二苯基(2,4,6-三甲基苯甲酰基)氧化膦,97%,CAS:75980-60-8),用旋涂或涂布等的方法成膜,然后在紫外光(如峰值365nm或390nm紫外LED灯)的照射下固化,形成颜色转换薄膜。
以上的绿色颜色转换薄膜可以放置在蓝色自发光器件,该蓝色自发光器件发射出发光峰在400-490nm之间的蓝光;蓝光经过绿色颜色转换器,发射出发光峰在490-550nm之间的绿光。
实施例3:基于顶发射(Top-Emission)OLED发光器件的制备
制备顶发射OLED所要用到的材料:
Ink1的制备:配取预聚物:称取乙酸正丁酯(42wt%):甲基丙烯酸甲酯(MMA)(50wt%)、丙烯酸羟丙酯(HPA)(3wt%),过氧化二苯甲酰(BPO)(5wt%),混合并在125℃搅拌50分钟,得到预聚物;以上预聚物(67wt%)+乙酸正丁酯(30wt%)+颜色转换主体材料(H13)(2.5wt%)+无机纳米发光体E,即绿色量子点QD1(0.5wt%),搅拌得到澄清溶液Ink1。
Ink2的制备:分别称取50mg颜色转换主体材料(H13)、10mg无机发光体,即绿色量子点QD1,然后将以上物质一起溶解在1ml乙酸正丁酯中,得到澄清溶液Ink2。
1.绿光发光器件1
a、含有Ag的发射层ITO(氧化铟锡)top基片的清洗:依次使用strip液,纯水,异丙醇超声清洗,然后烘干后进行Ar臭氧处理;
b、蒸镀:将基片移入真空气相沉积设备中,在高真空(1×10
-6毫巴)下,控制PD和HT-1的比例为3:100,形成10nm的空穴注入层(HIL),随后在空穴注入层上蒸镀化合物HT-1形成120nm的空穴传输层(HTL),紧接着在空穴传输层上蒸镀化合物HT-2形成10nm的空穴调整层。作为发光层,以BH:BD按照100:3的比例形成25nm的发光层薄膜。接下来作为电子传输层形成35nm的ET:LiQ(1:1)薄膜,置于不同的蒸发单元,使其分别以50重量%的比例进行共沉积,得到第二电子传输层,随后沉积1.5nm的Yb作为电子注入层,再在所述电子注入层上沉积厚度为16nm的Mg:Ag(1:9)合金作为阴极;
c、在阴极上,用海斯电子IJDAS310(喷头FUJIFILM Dimatix DMC-11610)打印Ink1,然后在峰值390nm紫外LED灯的照射下固化,得到厚度2-3μm的颜色转换层;
d、封装:器件在氮气手套箱中用紫外线硬化树脂封装。
2.绿光发光器件2:a、b、d步骤同上述的绿光发光器件1,c步骤如下:
c、在阴极上,用海斯电子IJDAS310(喷头FUJIFILM Dimatix DMC-11610)打印Ink2,得到厚度1-2μm的颜色转换层。
3.绿光发光器件3:a、b、c步骤同上述的绿光发光器件1,d、e步骤如下:
d、在颜色转换层上蒸镀厚度为70nm CPL作为光学覆盖层;
e、封装:器件在氮气手套箱中用紫外线硬化树脂封装。
4.绿光发光器件4:a、b、c步骤同上述的绿光发光器件2,d、e步骤如下:
d、在颜色转换层上蒸镀厚度为70nm CPL作为光学覆盖层;
e、封装:器件在氮气手套箱中用紫外线硬化树脂封装。
以上绿光发光器件1-4都具有较高的色纯度,其发光谱线的FWHM都在30nm以下。
以上所述实施例的各技术特征可以进行任意的组合,为使描述简洁,未对上述实施例中的各个技术特征所有可能的组合都进行描述,然而,只要这些技术特征的组合不存在矛盾,都应当认为是本说明书记载的范围。
以上所述实施例仅表达了本发明的几种实施方式,其描述较为具体和详细,但并不能因此而理解为对发明专利范围的限制。应当指出的是,对于本领域的普通技术人员来说,在不脱离本发明构思的前提下,还可以做出若干变形和改进,这些都属于本发明的保护范围。因此,本发明专利的保护范围应以所附权利要求为准。
Claims (12)
- 一种混合物,包含一种有机化合物H、一种无机纳米发光体E和至少一种有机树脂,其特征在于,1)所述有机化合物H的发光谱在所述无机纳米发光体E的吸收谱的短波长的一侧,且至少部分相互重叠;2)所述无机纳米发光体E的发光谱的半峰宽(FWHM)小于或等于45nm。
- 根据权利要求1所述的混合物,其特征在于,所述无机纳米发光体E选自具有单分布的胶体量子点或纳米棒。
- 根据权利要求2所述的混合物,其特征在于,所述无机纳米发光体E包含有半导体材料,选自CdSe,CdS,CdTe,ZnO,ZnSe,ZnS,ZnTe,HgS,HgSe,HgTe,CdZnSe,InAs,InP,InN,GaN,InSb,InAsP,InGaAs,GaAs,GaP,GaSb,AlP,AlN,AlAs,AlSb,CdSeTe,ZnCdSe,PbSe,PbTe,PbS,PbSnTe,Tl 2SnTe 5及它们的任何组合。
- 根据权利要求3所述的混合物,其特征在于,所述无机纳米发光体E是包含有两种不同的半导体的异质结构,所述异质结构是至少有一个外壳的核/壳(Core/Shell)结构。
- 根据权利要求1所述的混合物,其特征在于,所述有机化合物H选自包含至少一个以下基团的化合物:其中,Ar 1是芳基或杂芳基;X 1-X 8选于CR 1或N;X 9和X 10选于CR 1R 2或NR 1或O;R 1和R 2分别独立选自H、D,或具有1至20个C原子的直链的烷基、卤代烷基、烷氧基、硫代烷氧基基团,或具有3至20个C原子的支链或环状的烷基、卤代烷基、烷氧基、硫代烷氧基基团或甲硅烷基基团,或具有1至20个C原子的取代的酮基基团,或具有2至20个C原子的烷氧基羰基基团,或具有7至20个C原子的芳氧基羰基基团,氰基基团,氨基甲酰基基团,卤甲酰基基团,甲酰基基团,异氰基基团,异氰酸酯基团,硫氰酸酯基团或异硫氰酸酯基团,羟基基团,硝基基团,NO 2,CF 3,Cl,Br,F,I,可交联的基团,或具有5至40个环原子的取代或未取代的芳族或杂芳族环系,或具有5至40个环原子的芳氧基或杂芳氧基基团,或具有5至40个环原子的芳胺基或杂芳胺基基团,以上取代基任意位置的二取代单元或这些基团的组合,其中一个或多个取代基团可以彼此和/或与所述基团键合的环形成单环或多环的脂族或芳族环系。
- 根据权利要求1所述的混合物,其特征在于,至少一种所述有机树脂为热固性树脂或UV可固化树脂。
- 根据权利要求6所述的混合物,其特征在于,至少一种所述有机树脂的比重为20wt%至99wt%。
- 一种组合物,包含一种如权利要求1-7中任一项所述的混合物,和至少一种溶剂。
- 根据权利要求8所述的组合物,其特征在于,所述溶剂选自水,醇,酯、芳族酮或芳族醚、脂肪族酮或脂肪族醚、或硼酸酯或磷酸酯等无机酯类化合物,或两种及两种以上溶剂的混合物。
- 一种有机功能材料薄膜,包含一种如权利要求1-7中任一项所述的混合物。
- 一种光电器件,包含一种如权利要求1-7中任一项所述的混合物或一种如权利要求10所述的有机功能材料薄膜。
- 一种有机发光器件,自下而上依次包含一基板、第一电极、一有机发光层、第二电极、一颜色转换层及一封装层,第二电极至少是部分透明,其特征在于:1)所述颜色转换层包含一种有机化合物H和一种无机纳米发光体E;2)所述颜色转换层至少部分吸收50%及以上有机发光层所发的透过第二电极的光;3)所述有机化合物H的发光谱在所述无机纳米发光体E的吸收谱的短波长的一侧,且至少部分相互重叠;4)所述无机纳米发光体E的发光谱的半峰宽(FWHM)小于或等于45nm。
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