CN101093874A - 由基质和掺杂材料组成的混合物,及由其构成层的方法 - Google Patents
由基质和掺杂材料组成的混合物,及由其构成层的方法 Download PDFInfo
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- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 3
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- 230000002378 acidificating effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- 238000002484 cyclic voltammetry Methods 0.000 description 1
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- 230000001419 dependent effect Effects 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000000840 electrochemical analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
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- 125000005842 heteroatom Chemical group 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/165—Electron transporting layers comprising dopants
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/30—Doping active layers, e.g. electron transporting layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/611—Charge transfer complexes
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
本发明涉及由至少一种基质材料和至少一种掺杂材料组成的混合物,用于制备由掺杂的有机材料构成的层,其中,所述掺杂材料是一种非活性的掺杂剂前体,并选自掺杂剂的二聚体、低聚物、聚合物、二螺化合物或多环,其中,所述掺杂材料通过施加活化能量而被分解。
Description
根据权利要求1和4的前述部分,本发明涉及由至少一种基质材料和至少一种掺杂材料组成的混合物,以及通过沉积制备在基底上由掺杂的有机材料构成的层的方法。
发明背景
掺杂的半导体材料例如考虑用于有机发光二极管(OLED)中。在此区分为不同类型的掺杂的层。载流子传输层掺杂有强给体化合物或强受体化合物。通过基质材料和掺杂材料之间的电荷迁移使得该层对电子或空穴有相当高的导电率。这如下改善了有机发光二极管的电学性质,使得对于确定的亮度需要较小的驱动电压。此外还带来众多其它优点,例如载流子更好地从电极注入,因此对其制备而言可考虑选择其它材料。另外,这样掺杂的层的厚度可以在宽范围内变化,传输层中的欧姆损失不会影响器件的效率。因此例如可以这样选择层厚度,使得器件中产生的光通过构造性干涉而最佳地从器件中耦合输出。
对于这种掺杂的层,常常选择摩尔浓度为1∶1(掺杂剂∶基质)到1∶100。掺杂的有机半导体层也用于其它有机器件中,例如有机太阳能电池或有机TFTs。这种掺杂的层例如可以由4,4′,4″-三(3-甲基苯基苯基氨基)三-苯胺(m-MTDATA)和四氟四氰基华二甲烷(F4-TCNQ)以摩尔比1∶50组成的混合物构成。这种掺杂层的其它形式是可以由红菲绕啉(BPhen)和铯以例如1∶8的摩尔比构成。
在制备有机半导体层时,有机物质转化为气相,然后沉积。原则上,有机物质可以由液相或由固相转入气相中。第一种情况称为蒸发,第二种情况称为升华。为了便于阅读,以下同意思使用这两种叫法,每种情况都应该包括既从固相也从液相进行蒸发。
目前,掺杂的有机层通过混合蒸发而制备。在此情况下,将基质材料和掺杂材料装入各自的蒸发源(蒸发器)中,并在高真空条件同时进行升华。来自两个蒸发源的蒸汽在基底上沉积下来。取决于所选择的蒸发速率、蒸发源的辐射特性以及排列的形状,得到所形成层的确定混合比。
这些方法具有一系列缺点。在整个蒸发过程中,必须很准确地控制蒸发源的蒸发速率,以便实现均匀掺杂。此外必须这样提供辐射特性和蒸发源的排列,使得在基底的整个面上,基质材料和掺杂剂的流动比例是恒定的。尤其是对于具有大基面的基底而言,保证实现这点是非常耗费的。另外,在设计蒸发装置时,对于每种掺杂的层,必须额外设置用于掺杂剂的蒸发器。尤其是显著增加了这种装置的维护成本。最后,为了运行蒸发器,产生明显增加的控制技术成本。
本发明的目的是提供一种制备由掺杂的有机材料构成的层的方法,其克服了现有技术的缺陷。尤其是提供一种方法,其中,基质材料和掺杂材料在共同的蒸发源中进行蒸发,并可以沉积在基底上。同时提供一种由基质材料和掺杂材料组成的混合物,该混合物可以用于这种方法中。最后还指出本发明方法的应用可能性。
这些目的是通过独立权利要求4的方法以及通过权利要求1的混合物而实现的。其它优选的实施方式由从属权利要求给出。
根据本发明是一种通过沉积制备在基底上由掺杂的有机材料构成的层的方法,其中,掺杂的半导体材料含有至少一种半导体-基质材料和至少一种掺杂材料,并且其中,至少一种半导体-基质材料和至少一种掺杂材料的混合物借助蒸发源而转化为蒸汽相,并且接下来沉积在基底上。可以使用两种或更多种材料的混合物。可以考虑权利要求中记载的材料作为基质材料和掺杂材料。
在本发明中,术语“二聚体”是指通过两个单基或双基相互反应而形成的化合物。
术语“低聚物”是指由多个双基形成的化合物,其中,一个双基的第一个基端部与另一双基的第一个基端部进行反应,因而新形成第二个端部,更大的双基再与另一双基的第二个端部进行反应。
术语“聚合物”是指相对低聚物而言由更多双基形成的化合物。
根据本发明,“二螺化合物”是双基的分子内加成产物,其基团中心这样间隔结构要素,使得所述结构要素结合形式上带有基团的(亦即相互反应的)碳原子。
根据本发明,“多环”是双基的分子内加成产物,其基团中心这样间隔结构要素,使得所述结构要素结合形式上带有基团的(亦即相互反应的)碳原子以外的原子(即,为此结合至少一个至少是α-位的原子)。
制备掺杂层的优选的本发明方法包括以下这些步骤:
(i)通过混合半导体材料和掺杂材料而制备预掺杂的材料,
(ii)加热蒸发在真空室的蒸发源中的预掺杂材料,并且蒸汽沉积在基底上,和
(iii)通过输入能量而使沉积的层活化。
预掺杂材料的制备例如可以通过混合成分的固相或者通过在溶液中混合以及随后除去溶剂而实现。在有利的方案中,预掺杂的材料在特别的压制件中使用。例如有利的是,由预掺杂的材料制备压制品,然后在随后的步骤(ii)中使用该压制品。出于其它目的,有利地可以使用作为粉末的预掺杂材料。
在本发明方法一种有利的方案中,在步骤(i)和(ii)中尽可能或者完全避免加入活化能量。
用于步骤(iii)的合适的活化能量例如可以是光能、微波、超声、热能或电能。
采用上述方法能够简化掺杂层的制备。同样可以这样设计基质材料和掺杂剂的分子流动性质,因为两者都可以由同一蒸发源进行升华/蒸发。蒸发速率的比值尽可能与时间无关,因为仅仅控制温度。还可以简化设计蒸发器设备来实施该方法。在计划和运行蒸发器设备以制备带有掺杂的半导体层的器件时,尤其是在制备带有有机层的器件如有机发光二极管时,省却了用于至少一个蒸发源的成本。
通常,在通过蒸发预掺杂材料来制备掺杂的层时存在两个困难。首先,基质材料和掺杂材料的蒸发温度会非常不同。这会导致预掺杂材料的组成与掺杂层的组成不相应。对于该困难已提出了技术解决方案(A.Werner等人,EP1643568;M.Long等人,“New capabilities invacuum thermal evaporation sources for small molecule OLEDManufacturing”,SID 06 Digest,第1474页)。但同样还存在着困难,传统的基质材料和掺杂材料相互自发地进行化学反应。而在层沉积后希望产生掺杂效果,这就不利地影响到对由预掺杂材料构成的掺杂层的加工。原因在于,基质和掺杂剂的反应产物具有盐的特征,因此很难蒸发或者不再能蒸发。
这种情况的例子是,为了制备掺杂的电子传输层,使给体类客体材料与受体类主体材料进行混合。例如当混合红菲绕啉与铯时形成盐,其不再能无残留且无分解产物地进行蒸发(同样适用于空穴传输层,例如当F4TCNQ与m-MTDATA混合时)。
所形成的化合物例如可以称为电荷-迁移剂-络合物,或者称为自由基离子盐或者一般称为盐。其可以具有很高的晶格能,例如由于盐的负离子和正离子的静电吸引。这会导致这样的化合物直到分解温度也不会蒸发。如果通过涂抹而向强受体类的黄色分子F4TCNQ中混入给体类的白色分子m-MTDATA,则形成深色的粉末。该粉末直到400℃也不会蒸发,虽然两种成分单独地分别在250℃以下就可以沉积下来。上述方法可以防止蒸发源中发生这种不希望的效果。
如果两种成分(直接起作用的掺杂剂和属于其的基质)在蒸发源中已经混合,如上所述,则立即发生反应:电子密度从一种分子迁移到另一种分子上。在本发明方法中,可以使用较少的反应性掺杂剂前体,其不能自发地与基质材料反应。两者可以任意地同时存在,而且完全和干净地从源中升华,没有留下反应产物。一旦所含有的掺杂剂前体被合适地激发,优选用短波长的光(蓝光或近紫外光),则沉积的层就得到掺杂。该掺杂剂前体(例如二聚体)此时通常不可逆地分解为两个相同的、但现在是高反应性的独特的掺杂剂,它们在n-掺杂情况下易于向周围的基质释放电子(或者可认为直接在激发和然后的分解之后也释放电子)。该掺杂过程纯粹基于氧化还原-化学而不是基于(路易斯)酸/碱化学。后者尤其是由于在分解前体物质时不释放氢原子或酸而受到阻止。这会导致半导体材料不希望的p-掺杂,从而部分或完全抵消所希望的n-掺杂效果。
该过程的产物是掺杂的基质以及掺杂剂的正离子、准惰性的最后阶段。因此现在得到均匀掺杂的、半导体性导电的层。
根据本发明,此时放弃了从两个不同的源进行混合蒸发,而是由基质(例如受体类的材料)和掺杂剂前体(例如给体类的材料,通过上述激发就会使其发挥出掺杂作用)组成的合适的混合物一起从一个源中蒸发出来。
前体化合物或前体不可逆的分解可能首先通过激发基质或掺杂剂前体而发生,然后电子从前体化合物迁移到基质材料上。前体化合物相应被氧化。认为,前体物质在氧化状态下不稳定,前体物质中的键发生不可逆的断裂。键断裂缺乏可逆性抑制了电子再传递回来,因而使掺杂状态稳定化。前体物质氧化状态的不稳定性例如表明,在电化学试验中可以不可逆地进行氧化。
以上描述并不是限制以下情形,由于该原因,在根据本发明将所述杂环化合物用于掺杂层中时,形成了属于各杂环基和双基的正离子,尤其是通过至少一个电子从各杂环基和双基、其二聚体、低聚物、二螺化合物或多环迁移到周围的基质材料上而形成。此时同样形成了基质材料的负离子,其在基质材料上移动。基质材料以此方式获得了相对于未掺杂基质材料的导电率有所提高的导电率。未掺杂的基质材料的导电率通常<10-8S/cm,尤其是常常<10-10S/cm。此时需注意,基质材料要具有足够高的纯度。这样的纯度是用传统方法,例如梯度升华而达到的。通过掺杂,这样的基质材料的导电率升高到大于10-8S/cm,常常>10-6S/cm。这尤其适合于以下基质材料,其相对于Fc/Fc+的还原电势小于-1V,优选相对于Fc/Fc+小于-1.7V,尤其是相对于Fc/Fc+小于-2.1V。符号Fc/Fc+是指氧化还原电对二茂铁/二茂铁鎓,在电化学电势测定例如循环伏安法中将其用作参比。
除了以上描述的抑制同时蒸发的成分之间不希望的副反应外,用本发明方法同样可以减小环境气氛对混合物可能的破坏性影响。即使当事先存在已经掺杂的和此外尚可升华的混合物时,尤其是当电子从强给体类的客体化合物迁移到弱受体类的主体(n-掺杂)时,还是需要特殊的预防措施:空气水分和氧气与混合物迅速反应,从而失去了掺杂作用,并且最后有未掺杂的主体。尤其是权利要求中X-Y所表示的掺杂剂和掺杂剂前体对大气物质的高耐受性能够使客体/主体混合物合适地用于空气。
掺杂
作为可n-掺杂的基质材料,尤其可以使用喹啉络合物,例如铝或其它主族金属的络合物,其中喹啉配体也可以被取代。基质材料尤其可以是三(8-羟基-喹啉)-铝。也可以任选使用其它具有O-和/或N-给体原子的铝络合物。
三(8-羟基-喹啉)-铝 Bphen=红菲绕啉(4,7-二苯基-1,10-菲咯啉)
C24H16N2
双-(2-甲基-8-喹啉)-4-(苯基-苯酚)-铝-(III)
喹啉络合物例如可以含有一个、两个或三个喹啉配体,其中,其它配体优选与中心原子上的O-和/或N-给体原子络合,例如上述Al-络合物。
作为基质材料,还可以使用菲咯啉,其可以被取代或未取代,尤其是芳基取代,例如苯基取代或萘基取代。尤其可以使用Bphen作为基质材料。
作为基质材料,还可以使用杂芳香族化合物,尤其是诸如噁二唑或三唑,任选还有吡咯、咪唑、三唑、吡啶、嘧啶、哒嗪等。杂芳香族化合物优选被取代,尤其是芳基取代,例如苯基取代或萘基取代。尤其可以使用以下的三唑作为基质材料。
3-(4-联苯基)-4-苯基-5-叔丁基苯基-1,2,4-三唑C.30H27N3
优选所用的基质材料完全由金属酞菁络合物尤其是ZnPc、卟啉络合物、Buckminster-富勒烯尤其是富勒烯C60,或者多并苯尤其是并四苯及其衍生物所组成。
应当理解,在本发明中,所述基质材料可相互间或与其它材料混合地进行使用。应当理解,也可以使用具有半导体性质的合适的其它有机基质材料。
用于OLED的典型电子传输材料相对于Fc/Fc+的还原电势约为-2.3V。对于有机太阳能电池中的典型电子传输材料而言,相对于Fc/Fc+的还原电势约为-1V。
通过活化所形成的给体应该具有氧化电势,其相对于Fc/Fc+(二茂铁/二茂铁鎓氧化还原电对)小于或等于约-1.5V,优选小于或等于约-2.0V,更优选小于或等于约-2.2V。
在预掺杂材料优选的压制件中,选择各成分,使得它们不自发地相互反应,而是在相应活化后即发生反应。认为,当前体化合物的氧化电势Vox_DP接近基质材料的还原电势Vred_Mat时,则可以自发地发生电子从前体化合物向基质材料迁移。例如,在室温下,甚至在没有光的情况下,10c,10c’-二(8,9-二甲基-2,3,5,6-四氢-1H,4H-3a,6a,10b-三氮杂-荧蒽基)也自发地与NTCDA发生反应。10c,10c’-二(8,9-二甲基-2,3,5,6-四氢-1H,4H-3a,6a,10b-三氮杂-荧蒽基)相对于Fc/Fc+(在四氢呋喃中)的氧化电势为-0.74V,而NTCDA相对于Fc/Fc+(在二氯甲烷中)的还原电势约-0.79V。与此相应地,有利的是Vox_DP-Vred_Mat大于0.05V,优选大于0.2V,更优选大于1V。由于势垒增大,因而较大的差别降低了热电子迁移的速度。
在一些应用中有利地选择该差别这么大,使得必须要确定的最小能量的光(例如蓝光)用于活化,而更小能量的光(例如黄光)不足以进行活化。在此情形下,本发明方法可以在黄光条件下操作的常见生产空间中进行。生产者可以通过视觉来监控该方法,因为通过黄光不能发生掺杂的活化。层沉积后,则可以通过用蓝光照射而进行活化。
在本发明的预掺杂材料有利的压制件中,前体物质具有确定的最小尺寸。根据本发明人的经验,特别是对于较小尺寸的掺杂剂,要考虑层沉积后掺杂剂的扩散。这使得形成良好限定的掺杂的空间结构变得困难。以基础性的基团计,该结构应该至少由2个分子环构成,优选由至少3个环或更多环构成。这些环可以彼此缩合或者简单结合,任选含有杂原子,并且分别是饱和或不饱和的。掺杂剂应该由至少15个原子,优选至少35个原子形成。摩尔质量超过100g/mol,优选200g/mol。以上要求导致掺杂剂需要空间,使得掺杂剂牢固地固定在基质中。相应较高的值适用相应的前体化合物,这视其含有多少个基团单元而定。对于二聚体作为前体化合物的情况,例如分别规定加倍的值。
掺杂浓度
优选掺杂剂与基质分子或聚合物基质分子的单体单元的掺杂浓度≤1∶1,优选掺杂浓度为1∶2或更小,特别优选1∶5或更小或者1∶10或更小。掺杂浓度可以在1∶1到1∶100000范围内,尤其是在1∶5到10000或1∶10到1000范围内,例如在1∶10到1∶100或1∶25到1∶50范围内,但并不限于此。
实施例
如上所述,在使用预掺杂的材料时存在两个困难。以下实施例优选用基质材料和掺杂材料进行,它们尽可能具有相近的蒸发温度。由此可以表明,本发明的预掺杂材料和本发明方法事实上解决了第二个困难,即,掺杂剂和基质的化学反应性。不过本领域技术人员立即会发现,通过与所述其它解决方案结合使得该限制变得有可能,从而多种其它传输材料可以与本发明的掺杂材料一起作为预掺杂的材料使用。
实施例1:
Me-NTCDI(R=甲基)
为了制备预掺杂的材料Me-NTCDI:D1,将1g N,N’-二(甲基)-1,4,5,8-萘四羧酸二酰亚胺(Me-NTCDI)和0.1g掺杂材料1,2,3,1’,2’,3’-六甲基-2,3,2’,3’-四氢-2,2’-二-1H-苯并咪唑(“D1”)在研钵中彼此混合。此时需注意,要减小光对混合物的影响。例如通过用颜色RAL1028的彩色薄膜遮住工作区域来保证这点。该彩色薄膜过滤掉绿色和蓝色颜色范围的光,仅透过桔黄色的光。从而减小或抑制了Me-NTCDI和D1的光诱导反应。
将四分之一的预掺杂材料装入真空室传统的蒸发源中。通过在约10-6Pa压力下的加热蒸发而使一层沉积在基底上。该基底设置有两个平行的铟-锡-氧化物条,用它们来确定导电率。接触达14mm长,间距为1.25mm。
在基底上由混合物沉积总层厚为1.5m的层(蒸发温度约180℃)。在蒸发过程中真空室需隔光。起初观察到所形成的膜没有导电性。打开视窗并用卤素灯照射该层之后,该层变成导电性的。导电率平均为2·10-6S/cm。
打开真空室后,证实蒸发源中的源残留量约为1重量%。
Me-NTCDI相对于Fc/Fc+的还原电势约为-1.1V。因此较难掺杂,尤其是明显难于经常使用的1,4,5,8-萘四羧酸二酐(NTCDA),其相对于Fc/Fc+的还原电势约为-0.75V。D1相对于Fc/Fc+的氧化电势约为-0.75V。基于D1的基团相对于Fc/Fc+的氧化电势为-1.99V。这为用该材料实现的良好掺杂结果奠定了基础。
实施例2:
NTCDA
如实施例1所述制备预掺杂的材料NTCDA:D1。不过此时不用Me-NTCDI而使用化合物1,4,5,8-萘四羧酸二酐(NTCDA)。观察到颜色变成绿色。
在可比较地进行实验情况下,在照射层之前就已发现平均导电率为2·10-6S/cm。打开真空室后,源残留量约为20重量%。
该结果可以归因于D1的氧化电势和NTCDA的还原电势的差别较小。
实施例3
并四苯
相应于实施例1,制备由1g并四苯和0.1g的1,2,3,1’,2’,3’-六甲基-4,5,4’,5’-四苯基-2,3,2’,3’-四氢-2,2’-二-1H-咪唑(D2)组成的预掺杂材料。
通过在约150℃下加热蒸发该混合物,照射后形成100nm厚的掺杂层,导电率为10-7S/cm。没有观察到源残留。
并四苯相对于Fc/Fc+的还原电势约为-2.1V。D2的氧化电势非常接近D1的氧化电势。基于D2的基团相对于Fc/Fc+的氧化电势为-2.79V。这对于在并四苯中为n-掺杂达到的良好掺杂结果奠定了基础。
实施例4:
由1g红荧烯Zn(ZnTPP)和0.1g D2制备预掺杂的材料红荧烯:D2。
在压机中由该材料制备1mm高和直径为10mm的压制品(使用动力学真空,压力为5吨)。
将压制品的四分之一加入蒸发源中,其它如实施例1所述加以使用。此时形成1.2m厚的层,活化后该层的平均导电率为5-10-7S/cm。没有观察到源残留。
压制品的蒸发温度约为210℃,大致相应于红荧烯本身的蒸发温度。颇有意思的是,D2明显足够固定地包埋在压制品中,尽管其有较高的挥发性(蒸发温度约130℃),但D2仍与红荧烯一起嵌入层中(并且在加热预掺杂的材料过程中也不转入气相中)。
可以在通常的挤压装置中进行压制,例如在红外光谱中用以制备KBr-压片的挤压装置。在此情况下,更易挥发的成分的分子份额有利地为50%或更小,较有利地为10%和更小。更易挥发的成分有利地是掺杂剂。
借助压制来压缩混合物中的所有孔,因此材料只可以从压制品的表面升华。这均匀地适用于更挥发性的成分,该成分一旦露出来,就以预定的比例与不太挥发的成分一起转入气相中。以此方式,在获得预先调节的量比例情况下,较难挥发的成分的升华行为决定了总混合物的升华行为。
红荧烯相对于Fc/Fc+的还原电势为2.06V。
实施例5:
CF-Ox
2,2′-(1,3-亚苯基)双[5-[4-(三氟甲基)苯基]-1,3,4-噁二唑]
如实施例1那样,混合1g CF-Ox和0.1g D2来制备预掺杂的材料。没有观察到颜色转变。通过在约160℃下对混合物进行加热蒸发来制备层。该层在活化前表现出低于测量界限的导电率。用汞蒸汽灯的光进行活化后,该层表现出10-7S/cm的导电率。
基质材料CF-Ox相对于Fc/Fc+的还原电势约为-2.2V。
根本上来说,在上述说明书和权利要求中公开的本发明的特征既可以单独地也可以以任意组合形式用于以不同的实施方式实现本发明。
Claims (8)
1.由至少一种基质材料和至少一种掺杂材料组成的混合物,用于制备由掺杂的有机材料构成的层,其特征在于,所述掺杂材料是一种非活性的掺杂剂前体,并选自掺杂剂的二聚体、低聚物、聚合物、二螺化合物或多环,其中,所述掺杂材料通过施加活化能量而被分解。
2.根据权利要求1的混合物1,其特征在于,所述掺杂剂选自:
其中,结构3具有一个或多个环状连接A和/或A1和/或A2,其中A、A1和A2可以是碳环、杂环和/或多环状的环体系,它们可以被取代或未取代;
其中,在结构5中,A1和A2如上定义,T=CR22、CR22R23、N、NR21、O或S;
其中,结构7具有一个或多个桥连接Z和/或Z1和/或Z2,其中,Z、Z1和Z2独立地选自烷基、烯基、炔基、环烷基、甲硅烷基、烷基甲硅烷基、偶氮、二硫化物、杂环烷基、杂环基、哌嗪基、二烷基醚、聚醚、伯烷基胺、芳基胺和聚胺、芳基和杂芳基;
其中,在结构8a-8c中,每个杂环中环的大小可以为5到7个原子;
其中,X、Y=O、S、N、NR21、P或PR21;R0-18、R21、R22和R23独立地选自,取代或未取代的芳基、杂芳基、杂环基、二芳基胺、二杂芳基胺、二烷基胺、杂芳基烷基胺、芳基烷基胺、H、F、环烷基、卤代环烷基、杂环烷基、烷基、烯基、炔基、三烷基甲硅烷基、三芳基甲硅烷基、卤素、苯乙烯基、烷氧基,芳氧基、硫代烷氧基、硫代芳氧基、甲硅烷基和三烷基甲硅烷基炔基,或者,其中,R0-18、R21、R22、R23单独地或组合为(杂)脂族或(杂)芳族的环体系部分。
3.根据权利要求1或2的混合物,其特征在于,选择电子传输材料作为基质材料。
4.根据权利要求3的混合物,其特征在于,所述基质材料选自喹啉络合物、菲咯啉、杂芳香族化合物、金属酞菁络合物和/或Buckminster-富勒烯。
5.通过沉积制备在基底上由掺杂的有机材料构成的层的方法,其中,掺杂的有机材料含有至少一种基质材料和至少一种掺杂材料,其特征在于,根据权利要求1到4之一的混合物在一个共同的蒸发源中转化为蒸汽相,接下来沉积在基底上,其中,所述掺杂材料作为非活性的掺杂材料使用,并且所述掺杂材料在该方法过程中被活化。
6.根据权利要求5的方法,其特征在于,通过光能、微波、超声、热能和/或电能进行活化。
7.根据权利要求5或6之一的方法用于形成有机发光二极管的掺杂的传输层的用途。
8.根据权利要求5或6之一的方法用于形成有机太阳能电池的掺杂的传输层的用途。
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CN101965653B (zh) * | 2008-02-27 | 2017-04-05 | 欧司朗Oled股份有限公司 | 用于制备掺杂的有机半导体层的方法 |
CN103038224A (zh) * | 2010-07-30 | 2013-04-10 | 日本瑞翁株式会社 | 醚化合物、非水系电池用电解液组合物、非水系电池电极用粘合剂组合物、非水系电池电极用浆料组合物、非水系电池用电极及非水系电池 |
CN110343073A (zh) * | 2015-07-02 | 2019-10-18 | 昆山国显光电有限公司 | 苯并咪唑类n-型掺杂剂及其在有机电致发光器件中的应用 |
CN106898701A (zh) * | 2015-12-18 | 2017-06-27 | 昆山国显光电有限公司 | 一种有机电致发光器件 |
CN106898701B (zh) * | 2015-12-18 | 2018-11-13 | 昆山国显光电有限公司 | 一种有机电致发光器件 |
CN109651370A (zh) * | 2018-12-17 | 2019-04-19 | 桂林理工大学 | 一种嘌呤类衍生物自由基前体分子及其制备方法 |
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CN101405884B (zh) | 2014-02-19 |
ATE394800T1 (de) | 2008-05-15 |
CN101405884A (zh) | 2009-04-08 |
KR20070095818A (ko) | 2007-10-01 |
US20070252140A1 (en) | 2007-11-01 |
CN101093874B (zh) | 2013-02-13 |
US8134146B2 (en) | 2012-03-13 |
EP1837926A1 (de) | 2007-09-26 |
KR100885582B1 (ko) | 2009-02-24 |
TW200745050A (en) | 2007-12-16 |
CN101134744A (zh) | 2008-03-05 |
US9118019B2 (en) | 2015-08-25 |
CN101134744B (zh) | 2012-07-04 |
JP2007314513A (ja) | 2007-12-06 |
JP4939988B2 (ja) | 2012-05-30 |
TWI436985B (zh) | 2014-05-11 |
US20120146012A1 (en) | 2012-06-14 |
EP1837926B1 (de) | 2008-05-07 |
HK1104677A1 (en) | 2008-01-18 |
ES2310380T3 (es) | 2009-01-01 |
DE502006000749D1 (de) | 2008-06-19 |
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