CN100418246C - 掺杂的有机半导体材料以及它们的制造方法 - Google Patents
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Abstract
本发明涉及一种通过添加一掺和物(1)制备具有加大载流子密度和有效载流子迁移率的掺杂的有机半导体材料的方法。在掺杂物(1)混入有机半导体材料之后***出氢、一氧化碳、氮或自由羟基和至少向半导体材料或从半导体材料传输一电子，该方法的突出特征是，应用一不带电荷的有机化合物作为掺杂物(1)。另外本发明涉及的掺杂的有机半导体材料是通过该方法之一获得的。该半导体材料显示出众的特点是在掺杂层中至少含有一种有机化合物的阳离子(2)，该有机化合物(1)不带电荷的形态在空气中是不稳定的。
Description
技术领域
本发明涉及具有加大载流子密度和有效载流子迁移率的掺杂的有机半导体材料以及通过添加一种掺杂物制造它们的方法，在有机半导体材料中混入掺杂物之后***出氢、一氧化碳、氮或自由羟基和至少传输给有机半导体材料一个电子或由有机半导体材料传输出来。
背景技术
自从1989年有机发光二极管和太阳能电池演示以来[C.W.Tang etal，Appl.phys.Lett.，1987，913]由有机薄层组成的元件成为热门研究的对象。这些薄层对所述用途具有卓越的性能，例如对有机发光二极管能有效电致发光，对有机太阳能电池可见光区域有高吸收系数，在材料制造和制成最简便的电路元件方面具有价格优势以及有机发光二极管应用在显示器领域已经具有商业意义。
光电子多层元件的性能特点除其他因素外是由薄层载流子的传输能力决定的。在发光二极管情况下，运行时电流传输层中的电阻损失与导电性联系在一起，而后者一方面对所需的操作电压直接有影响；另一方面它也决定着元件热负荷。另外还与有机薄层到金属接触点附近能带弯曲处的载流子浓度有关，在这里载流子的注入变得容易，从而能使接触电阻减小。相似的思路对有机太阳能电池同样可得出这样的结论，其效率也是由载流子的传输性能来决定的。
通过用一适宜的受主材料掺杂空穴传输层(p-掺杂)或用一施主材料掺杂电子传输层(n-掺杂)能使有机固体物质中的载流子密度(从而使导电性)明显提高。此外，根据无机半导体应用的经验可以得到类似的预期，正是在元件中应用了p-和n-掺杂层而不可能是其他因素导致这一结果。US5.093.698描述了在有机发光二极管中掺杂的载流子传输层的应用(通过混入受主类型的分子使空穴传输层得到p-掺杂，混入施主类型分子使电子传输层得到n-掺杂)。
无机材料掺杂，一方面因所用掺杂材料为相对小的分子或原子的形式，存在扩散方面的问题；而另一方面在基体和掺杂材料之间还同时存在不希望出现的而又难以预知的化学反应。与用无机材料掺杂方法不同的有机分子作为掺杂材料则显示出其优越性。一般而言，有机掺杂物在元件中具有较高的稳定性。扩散作用居次要地位，这就能使由p-掺杂区到n-掺杂区清晰过渡的制造规定得以简化。用有机分子掺杂时，唯一的可能是在基体和掺杂材料之间的电荷转移，在它们之间是不能形成化学键的。另外，在有机掺杂物情况下为保持在掺杂层中有较高的导电性，有利的掺杂浓度大约是无机掺杂物的3-4数量单位。
对应用有机掺杂物来说，所需的掺杂材料希望能够在p-掺杂上表现出极强的电子亲和性或还原位能，或者是在n-掺杂上表现出相应的离子位能或氧化位能，这时它们的化学稳定性则较弱，而且难于实现，这是其不利的方面。
A.G.Werner等人，Appl.Phys.Lett.，2003，4495-7，在有机半导体材料中应用焦宁B作为掺杂材料，为此将焦宁B氯化物升华，这时主要形成氯化氢和焦宁B的一种经还原的质子化的形式，即焦宁B的隐色体。该隐色体作为稳定的前体物应用，它在真空中，在具有微小受体强度的基体材料存在下，通过蒸发又被氧化成一阳离子。
该方法的一个缺点是在反应过程中生成了阳离子染料的隐色形式。在该反应中产生了焦宁B的聚合作用，从而只能使有限的焦宁B氯化物升华。
另外，从H.Yokoi等Chemistry Letters，1999，241-2文章中已知四氟化四氰基对醌二甲烷(TCNQ)通过光诱导的电子转移和自由基阳离子的C-C断链实现光化学掺杂，此时将TNCQ与掺杂物的二聚体，例如二(对-甲氧基苯胺)甲基在一研钵中研磨进行混合。通过光照使二聚体产生氧化和向TNCQ进行电子转移。在氧化时C-C键断裂并生成一单体阳离子和一单体自由基，通过向TNCQ进行电子转移单体自由基氧化成阳离子。
该方法不能在真空下应用，所以不能与通常的有机半导体材料，例如富勒烯C60进行混合，这是它的缺陷。原则上在二聚体和阳离子单体的稳定性之间存在一直接倒数关系，因而阳离子单体越稳定，则其不带电的二聚体的稳定性则受到限制。
基于此，本发明的任务是在制造有机掺杂半导体材料时改善其收率和纯度。
发明内容
按照本发明，通过运用中性有机化合物作为掺杂物，使此项任务获得解决。由于采用了有机化合物的氢化形态，使聚合问题和副产品例如氯化氢的作用都得以避免，这与直接应用有机化合物的盐是不同的。
该有机化合物的氢化形式可以采用经过纯化的状态和直接混入有机半导体材料中去，该有机化合物的氢化形态是中性、非离子化的分子，因而基本上能够完全升华。这样，通过生成的阳离子染料升华的作用与有机化合物蒸发氢化形态的掺杂作用是相同的。
有机化合物成氢化形态的掺杂物，实用的方法是通过该有机化合物一种盐的升华制备的。因而制备有机化合物的氢化形态是在没有有机半导体之前的一个单独的步骤。另外为了改善有机化合物氢化形态的产率和纯度，还可以采取其他的净化过程。
在掺杂时预定不带电荷的有机化合物通过***出氢、一氧化碳、氢或自由羟基转变成有机化合物的阳离子或自由基。这样由自由基通过向半导体材料进行一电子转移而实现n-掺杂或通过接收半导体材料一阳离子而实现p-掺杂。
在本发明的一实施模式中，氢、一氧化碳、氮或自由羟基是从环戊二烯、环庚三烯或一六节的杂环化合物***出的。电子释放(n-掺杂)或接收(p-掺杂)通过6π-芳香族体系的构成而得以促进。
环戊二烯、环庚三烯或一六节的杂环化合物可以作为一稠合环体系的组成部分替代或补充，因而在生成一8π-，10π-，12π-或一其它(2n)π-体系时，也有助于电子转移。
有利的不带电荷的有机化合物是一阳离子染料的隐性母体或甲醇基化物(carbinolbase)，应用这类分子有机发光二极管能有发光效率的高量子效应，例如像若丹明B阳离子染料往往有高荧光量子收率，这样它在以后的有机发光二极管中可作为荧光染料应用。
也可交替应用呫吨-、吖啶-、二苯胺-、三苯胺、吖嗪-、噁嗪-、噻嗪-或噻吨-染料衍生物作为染料。然而选择适于掺杂用途的物质不仅仅只局限于阳离子染料，例如那些***出不是氢化物的其它基团能够转换成阳离子的化合物也是适用的。
其它优选的实施方式在下述权利要求中。
此外，为解决此项任务可通过按本发明的方法经掺杂的具有加大载流子密度和有效载流子迁移率的有机半导体材料实现，此处在掺杂层中的阳离子至少含有一有机化合物，它的不带电荷的形态在空气中是不稳定的。
其它优选的实施方式在下述权利要求中。
附图说明
下面借助一在图中描述的实施例对本发明进行阐明。它表明：
图1：按本发明的反应由隐色结晶紫经过氧化转变成结晶紫一阳离子。
具体实施方式
在按本发明方法的实施例中为制备掺杂的有机半导体应用结晶紫作为阳离子染料。
作为氯化物盐存在因而是稳定的染料，第一步首先是进行升华。在该过程中释放出氯化氢，得到的是结晶紫的不带电荷的还原形态，作为它的隐色体1产率较低。
隐色体1是一前体物质，由其在第二步制得施主2，在没有紫外线照射的情况下，该隐色结晶紫1在空气中是稳定的，隐色结晶紫2对SCE的氧化电位是0.7V。一般情况下对SCE的氧化电位大于0.3V的材料动力学是稳定的，也就是说，在空气中呈惰性。隐色结晶紫1在空气中呈现惰性，这就使施主的前体物的操作处理简单化，是很有利的。这样可将隐色体直接加到掺杂过程中去。
为此可将纯净的隐色体1加到具有适宜受主强度的一种有机半导体材料即富勒烯C60中一起混合。所选择的掺杂浓度取决于所需的导电率。典型的掺杂浓度位于1∶5000到1∶10的范围内，它也可以超出1∶10。
而后在第二步中隐色体又被氧化成阳离子，从而产生了掺杂作用(图1)。隐色结晶紫1在第二步反应成为施主2。在此氧化过程中隐色体1反应成结晶紫-阳离子，同时将电子传输给半导体材料富勒烯并***出氢。
结晶紫-阳离子对NHE的还原电位是-0.1V，因此它肯定优于迄今已知的所有在空气中稳定的有机施主。一般而言，阳离子染料用于掺杂基体材料时，其对SCE，如富勒烯C60，的还原电位小于0V时特别适用。
有关标记说明
1.中性有机化合物(掺杂物)
2.有机化合物阳离子
Claims (18)
1. 通过添加一掺杂物制备具有加大载流子密度和有效载流子迁移率的掺杂的有机半导体材料的方法，在掺杂物混入有机半导体材料之后***出氢、一氧化碳、氮或自由羟基和至少向半导体材料或从半导体材料传输一电子，其特征在于，应用一不带电荷的有机化合物作为掺杂物。
2. 按权利要求1的方法，其特征在于，掺杂物是通过一有机化合物的盐升华制备的。
3. 按权利要求1或2之一的方法，其特征在于，不带电荷的有机化合物通过***出氢、一氧化碳、氮或自由羟基转变为阳离子或有机化合物自由基。
4. 按权利要求1的方法，其特征在于，氢、一氧化碳、氮或自由羟基是由一环戊二烯、环庚三烯或六节的杂环在生成一6π-芳香族体系时***出来的。
5. 按权利要求4的方法，其特征在于，环戊二烯、环庚三烯或六节的杂环是一稠合环体系的组成部分。
6. 按权利要求1的方法，其特征在于，不带电荷的有机化合物是一阳离子染料的甲醇基化合物或隐色体。
7. 按权利要求1的方法，其特征在于，是应用呫吨-、吖啶-、二苯胺-、三苯胺、吖嗪-、噁嗪-、噻嗪-或噻吨-染料衍生物作为染料。
8. 按权利要求1的方法，其特征在于，不带电荷的有机化合物在与有机半导体材料混合之前或之后进行光照或用一电子射线激发。
9. 按权利要求8的方法，其特征在于，用于光照的辐射光谱至少部分覆盖该中性化合物和/或拟掺杂的半导体材料的吸收范围。
10. 按权利要求1的方法，其特征在于，在掺杂物和有机半导体材料之间不形成化学键，至少有一电荷转移。
11. 按权利要求1的方法，其特征在于，有机半导体材料与一阳离子染料或其隐色体或其甲醇基化合物通过混合蒸发或相继前后蒸发进行掺杂，由阳离子染料生成的化合物经过电子射线辐照或在有机半导体材料和/或生成的化合物的吸收范围内进行光照又转变为阳离子。
12. 按权利要求1的方法，其特征在于，制成的非均质的薄层中有机半导体材料和掺杂物具有的氧化还原位能互相协调为使在黑暗时的基体中的化合物呈惰性。
13. 具有加大载流子密度和有效载流子迁移率的掺杂的有机半导体材料，其特征在于，在掺杂层中含有至少一有机化合物的阳离子，该化合物不带电荷的形态在空气中是不稳定的。
14. 按权利要求13的半导体材料，其特征在于，该有机化合物是一染料。
15. 按权利要求14的半导体材料，其特征在于，该染料是一呫吨-、吖啶-、二苯胺-、三苯胺、吖嗪-、噁嗪-、噻嗪-或噻吨-染料。
16. 按权利要求13至15之一的半导体材料，其特征在于，不带电荷的有机化合物是一阳离子染料的甲醇基化合物或隐色体。
17. 按权利要求13的半导体材料，其特征在于，氢、一氧化碳、氮或自由羟基是由一环戊二烯、环庚三烯或六节的杂环中***出来的。
18. 按权利要求17的半导体材料，其特征在于，环戊二烯、环庚三烯或六节的杂环是一稠合环体系的组成部分。
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- 2004-07-09 EP EP04016187A patent/EP1508903A3/de not_active Ceased
- 2004-07-12 IN IN746MU2004 patent/IN2004MU00746A/en unknown
- 2004-07-29 CA CA002476168A patent/CA2476168A1/en not_active Abandoned
- 2004-08-02 JP JP2004225183A patent/JP4108654B2/ja not_active Expired - Fee Related
- 2004-08-06 CN CNB2004100565198A patent/CN100418246C/zh not_active Expired - Fee Related
- 2004-08-17 US US10/920,062 patent/US7151007B2/en active Active
- 2004-08-18 KR KR1020040065104A patent/KR100746798B1/ko active IP Right Grant
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6566807B1 (en) * | 1998-12-28 | 2003-05-20 | Sharp Kabushiki Kaisha | Organic electroluminescent element and production method thereof |
| CN1370034A (zh) * | 2001-02-08 | 2002-09-18 | 株式会社半导体能源研究所 | 发光器件 |
| US20030072890A1 (en) * | 2001-09-14 | 2003-04-17 | Seiko Epson Corporation | Method for patterning, method for manufacturing film, patterning apparatus, method for manufacturing organic electroluminescent element, method for manufacturing color filter, electro-optic apparatus and method for manufacturing the same, electronic apparatus and method for manufacturing the same, and electronic equipment |
Also Published As
| Publication number | Publication date |
|---|---|
| IN2004MU00746A (zh) | 2006-06-16 |
| EP1508903A3 (de) | 2006-02-15 |
| JP2005063960A (ja) | 2005-03-10 |
| US7151007B2 (en) | 2006-12-19 |
| TW200509428A (en) | 2005-03-01 |
| US20050061232A1 (en) | 2005-03-24 |
| CA2476168A1 (en) | 2005-02-18 |
| KR20050020663A (ko) | 2005-03-04 |
| CN1591926A (zh) | 2005-03-09 |
| KR100746798B1 (ko) | 2007-08-06 |
| EP1508903A2 (de) | 2005-02-23 |
| JP4108654B2 (ja) | 2008-06-25 |
| DE10338406A1 (de) | 2005-03-24 |
| TWI265648B (en) | 2006-11-01 |
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