CN1791656A - 粘度调节剂和发光化合物的共混物 - Google Patents
粘度调节剂和发光化合物的共混物 Download PDFInfo
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- CN1791656A CN1791656A CNA2004800137367A CN200480013736A CN1791656A CN 1791656 A CN1791656 A CN 1791656A CN A2004800137367 A CNA2004800137367 A CN A2004800137367A CN 200480013736 A CN200480013736 A CN 200480013736A CN 1791656 A CN1791656 A CN 1791656A
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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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
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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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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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
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Abstract
本发明涉及一种发光聚合物和低分子量(<5000amu)粘度调节剂的共混物的组合物,所述粘度调节剂的最大发射波长在350-480nm范围内,不含环外双键,并且在基本上不改变纯聚合物发射性质的情况下调节聚合物的粘度。当已经将聚合物调节到在所需波长处发光的情况下,在不伴随着发射性质改变的情况下改变粘度是适宜的。
Description
本发明涉及一种粘度调节剂和发光化合物的共混物。
发光聚合物使用于多种应用领域中,所述的应用包括卷装进出(roll-to-roll)、屏幕和喷墨印刷;旋转、浸渍和喷射涂布;以及“刮板(doctorblading)”。尽管所有这些应用可能要求材料在特定波长下发射,而对它们的粘度要求却经常差异很大。因而,对于可以同时用于卷装进出和喷墨应用的发光聚合物可能在前一应用中要求有高粘度(100cps),而在后者中要求具有相对低的粘度(10cps)。
发光聚合物的粘度调节剂是已知的。例如,在美国专利6,372,154中,Li描述了低分子量功能添加剂在调节包含粘性发光聚合物的发光油墨(L-油墨)的粘度中的应用。这些功能添加剂被描述为具有电子输送性或者空穴输送性,即除了粘度调节外,还可用于改变L-油墨的电荷输送性质。但是,能够在不改变电荷输送性质的情况下改变发光聚合物的粘度是适宜的,改变电荷输送性质可能对发光性质产生不利影响。因此,如果发光聚合物本来就在所需波长处发射,则使用降低粘度但伴随着使共混物的发光发射最大值位移到基本上不同其最佳波长的波长处的调节剂将是不利的。因此,在发光聚合物粘度调节技术领域中,发现能够在基本上不改变纯聚合物发射性质的情况下改变其粘度的调节剂是有利的。
本发明针对本领域现有技术的不足,提供一种包含a)重均分子量(Mw)至少为20,000的发光聚合物和b)粘度调节剂的共混物的组合物,所述粘度调节剂具有如下性质:1)在室温下是固体;2)Mw小于5000;3)发光发射最大值在350到480nm范围内;4)基本上不减小调节剂和聚合物的组合的电荷输送性质;和5)不含环外共轭双键;其中选择调节剂及其在共混物中的粘度,使共混物表现出在单独的聚合物的发光发射最大值20nm以内的发光发射最大值。
本发明所述的共混物提供了一条在基本上不改变纯聚合物发光发射最大值的情况下调节粘度的途径。当纯聚合物已经拥有最佳发光发射性质时,这个效果特别有利。
本发明是一种组合物,该组合物是发光聚合物和粘度调节剂的共混物。发光聚合物可以是任何在UV辐照下或者在合适的电场偏置下发光的聚合物。优选聚合物在电场偏置下发光,即具有场致发光性。发光聚合物的实例包括含有以下结构单元的那些发光聚合物:9,9-二取代芴,包括9,9-二烷基芴、9,9-二芳基芴和9,9-二芳烷基芴;9-取代芴,如螺芴;亚苯基,包括2,5-二烷氧基亚苯基和2,5-二烷基亚苯基;亚苯基亚乙烯基,包括2-甲氧基-5-(2’-乙基己基)亚苯基亚乙烯基、2,5-二辛氧基-1,4-亚苯基亚乙烯基、2-甲硅烷基-1,4-亚苯基亚乙烯基、2,5-二甲硅烷基-1,4-亚苯基亚乙烯基和2,5-二烷基-1,4-亚苯基亚乙烯基;噻吩;3-烷基噻吩;噻吩亚乙烯基;吡咯;乙炔;联乙炔;苯胺;N-乙烯基咔唑;以及它们的组合。此处使用的术语“结构单元”是指经历聚合后的化合物的残余。因此,反式-乙炔结构单元由下面结构表示:
优选的发光聚合物包含9,9-二取代芴结构单元,9,9-二取代芴是通过2和7碳原子聚合的,其结构单元由如下结构表示:
9,9-二取代芴结构单元
其中每个R独立地为烷基、烷氧基、芳基、芳氧基或芳烷基;优选为C1-C20烷基、C1-C20-烷氧基、取代的或未取代的苯基、联苯基、萘基、蒽基、菲基、噻吩基或呋喃基;更优选为C4-C12烷基、C4-C12-烷氧基,或者取代或未取代的苯基或联苯基。
发光聚合物更优选包含9,9-二取代芴的结构单元和至少一种其它共聚单体的结构单元。包含9,9-二取代芴和其它共聚单体结构单元的聚合物实例可以在美国专利5,708,130、5,777,070、6,169,163和6,363,083中找到。
合适的共聚单体的实例包括可聚合的取代和未取代的噻吩、二噻吩、苯并二噻唑、噁唑、噁二唑、苯并噁唑、二苯并呋喃、苯并噻吩、二苯并噻吩、dibenzosiloles、包括N,N,N’,N’-四芳基联苯胺的联苯胺、二芳基胺、三芳基胺、苯、亚联苯基、萘、蒽、菲、苯乙烯、喹啉和1,2-二苯乙烯。更优选的共聚单体包括联苯胺、二噻吩和苯并噻二唑。
用于形成共混物的粘度调节剂在室温下为固体。其重均分子量(Mw)小于5000,优选小于2000,并且多分散性小于1.2,更优选小于1.1,最优选为1.0。调节剂的发光发射最大值不大于480nm且不小于350nm,更优选不小于400nm。因此,调节剂在最高占据分子轨道(HOMO)和最低未占据分子轨道(LUMO)之间的带隙宽于场致发光聚合物的发射生色团的带隙。据信该相对较宽的调节剂带隙导致共混物的发光发射最大值与聚合物相比基本上没有位移。
选择调节剂,以基本上不减小调节剂和聚合物的组合的电荷输送性质,因为这样的调节剂趋向于对发光材料的效率有不利影响。具有这种不利趋势的调节剂是含有具有离域非共享电子对的杂原子的那些调节剂,所述具有离域非共享电子对的杂原子如具有离域非共享电子对的N、O和S原子。因此,含有两个具有离域非共享电子对的氮原子的二萘-1-基-二苯基-联苯基-4,4’-二胺(α-NPA)不是合适的用于发光聚合物的调节剂。
还选择调节剂使其不含环外共轭双键,即它不含非芳香族共轭双键,因为这样的混合物趋向于易于氧化。因此,1,1,4,4-四苯基-1,3-丁二烯(TPB)也不是合适的用于发光化合物的调节剂。
此外,如此选择共混物中调节剂及其浓度,使共混物表现出的发光发射最大值在单独的聚合物的发光发射最大值的20nm以内,优选10nm以内,更优选在5nm以内,最优选在1nm以内。优选,基于调节剂和发光聚合物的重量,调节剂的重量百分比浓度至少为1重量百分比,更优选至少5重量百分比,最优选至少10重量百分比;并且优选小于60重量百分比,更优选小于50重量百分比,最优选小于30重量百分比。
优选的调节剂的实例是取代的和未取代的芴及其共混物;芴低聚体,如一-、二-和三-9,9-二取代芴以及它们的共混物;亚芴基及其共混物,和三芴基苯及其共混物。三-9,9-二取代芴的一个实例由下面结构所图示:
其中R如先前所定义。
该三-9,9-二取代芴可以通过如下所示的Suzuki偶联反应来制备:
类似地,可以通过三溴苯和2-(1,3,2-二氧杂硼戊烷(dioxaborloan)-2-基)-9,9-二丁基芴反应来制备三芴基苯。优选的三芴基苯包括1,3,5-三(9,9-二取代芴基)苯,其中R如先前所定义。
二芴基-取代亚联芴基的一个实例由下面结构图示:
其中R如先前所定义。该亚联芴基可以通过如下面反应顺序所述地来制备:
其中R如先前所定义,优选每个R独立地为C4-C12-烷基,更优选为C4-C8-烷基。
将发光聚合物和粘度调节剂有利地和足量溶剂组合,制成油墨。溶剂的量根据溶剂本身及其应用而变化,但是其使用浓度基于发光聚合物、调节剂和溶剂的重量通常为至少80重量百分比,更优选为至少90重量百分比,最优选为至少95重量百分比。
用于聚合物和调节剂的合适溶剂的实例包括苯;一-、二-和三烷基苯,包括二甲苯、1,3,5-三甲基苯、甲苯、正丙基苯、正丁基苯、正戊基苯、正己基苯、环己基苯、二乙基苯、十二烷基苯和正戊基苯;呋喃,包括四氢呋喃和2,3-苯并呋喃;1,2,3,4-四氢化萘(四氢化萘);枯烯;顺式和反式-萘烷(十氢化萘);杜烯;氯仿;1,8-萜二烯;烷氧基苯,包括茴香醚和甲基茴香醚;苯甲酸烷基酯,包括苯甲酸甲酯;联苯,包括异丙基联苯;吡咯烷酮,包括环己基吡咯烷酮;咪唑,包括二甲基咪唑;以及它们的组合。更优选的溶剂包括甲苯、环己基苯、二甲苯、1,3,5-三甲基苯、1,2,3,4-四氢化萘、苯甲酸甲酯、异丙基联苯和茴香醚,以及它们的组合。
在一种典型的应用中,可以将油墨配方沉积在其上安置了空穴输送材料的衬底上如铟-锡-氧化物(ITO)玻璃上。然后蒸发溶剂,由此油墨形成粘度调节的发光聚合物的多孔薄膜。显然,粘度调节剂的存在提供了一条在不影响膜厚度的关键性质的情况下调节粘度的途径。所述膜被用作有机发光二极管(OLED)中的活性层,OLED可以用作制造自发射平板显示器。
如下实施例仅用于说明目的,而不限制本发明的范围。
实施例1-4:粘度调节的聚合物的配方的制备
A、1,3,5-三(9,9-二丁基芴基)苯的制备
将1,3,5-三溴苯(3.12g,9.92mmol)、2-(1,3,2-二氧杂硼戊烷-2-基)-9,9-二丁基芴(12.10g,34.72mmol)和季铵氯化物336(Aliquat 336)(1.5g)溶解在125mL甲苯中,并且加入到装备有悬挂(overhead)搅拌器和连接到氮气管线上的回流冷凝器的250-mL 3颈烧瓶中。向混合物中加入Na2CO3水溶液(2M,30mL),并将烧瓶用氮气吹扫10分钟。向混合物中加入Pd(PPh3)4(0.2g,0.5摩尔百分比),然后在搅拌下加热到95℃过夜。加入二乙基二硫代氨基甲酸钠盐三水合物的溶液(5%,200mL),将混合物在80℃加热16小时。除去水层,有机层用温热的稀乙酸溶液(2%,3×300mL)、随后用热水(1×300mL)洗涤,最后用MgSO4干燥。真空除去甲苯,得到粗产物。该粗产物经硅胶柱色谱纯化,用己烷/二氯甲烷洗脱,得到7g(78%)的1,3,5-三(9,9-二丁基芴基)苯,为白色固体。HPLC显示产物的纯度>99%。1,2,4-三(9,9-二丁基芴基)苯异构体的制备方法基本上如上所述,不同之处在于使用1,2,4-三溴苯代替1,3,5异构体作为原料。这些异构体每个都用作B部分中所述的粘度调节剂。
B、油墨配方的制备
在单个容器中将场致发光聚合物、粘度调节剂和溶剂合并在一起并混合,获得均匀溶液或者油墨。下表显示了溶剂中的聚合物和调节剂的浓度。在每一种情况下,溶剂都是二甲苯异构体和乙基苯的混合物(作为VLSI级混合的二甲苯获自J.T.Baker,并且分析为:间二甲苯,40-65%;邻二甲苯,15-20%;对二甲苯<20%;乙基苯,15-25%),其含量基于溶剂、聚合物和调节剂的总重量为98重量%。聚合物1304是指LUMATION* 1304绿光发射聚合物(Dow Chemical Company的商标),而聚合物1100是指LUMATION* 1100红光发射聚合物,均可获自Dow Chemical Company。VM1是指1,2,4-三(9,9-二丁基芴基苯),VM2是指1,3,5-三(9,9-二丁基芴基苯)。实施例1和4是比较例,因此不在本发明共混物的范围之内。包括这些比较例是为了证明,与纯的聚合物相比,粘度调节剂基本上没有改变共混物的最大发射波长。此外,数据表明调节剂的存在提高了器件的效率。
表
实施例# | 聚合物(重量/重量%) | 粘度调节剂(重量/重量%) | 溶液粘度(cPs) | EL最大发射波长(nm) | 器件效率@1000Cd/m2 |
1(比较例) | 1304(2%) | 无(0%) | 16.02 | 536 | 6.34 |
2 | 1304(1.5%) | VM1(0.5%) | 8.78 | 532 | 6.68 |
3 | 1304(1%) | VM1(1%) | 4.18 | 532 | 6.82 |
4(比较例) | 1100(2%) | 无(0%) | 644 | 0.738 | |
5 | 1100(1%) | VM2(1%) | 640 | 0.790 |
Claims (10)
1、一种组合物,其包含a)和b)的共混物,
a)重均分子量(Mw)至少为20,000的发光聚合物,和
b)粘度调节剂,所述粘度调节剂
1)在室温下是固体;
2)Mw小于5000;
3)发光发射最大值为350到480nm;
4)基本上不减小调节剂和聚合物的组合的电荷输送性质;和
5)不含环外共轭双键;其中选择调节剂及其在共混物中的粘度,使共混物表现出在单独的聚合物的发光发射最大值20nm以内的发光发射最大值。
2、权利要求1的组合物,其中粘度调节剂不含任何一种具有离域非共享电子对的O、N或S。
3、权利要求1或2的组合物,该组合物还包含用于发光聚合物和粘度调节剂的溶剂,该溶剂选自甲苯、环己基苯、二甲苯、1,3,5-三甲基苯、1,2,3,4-四氢化萘、苯甲酸甲酯、异丙基联苯和茴香醚,以及它们的组合。
4、权利要求1到3任何一项所述的组合物,其中共混物的发光发射最大值在聚合物的发光发射最大值的10nm以内。
5、权利要求1到4任何一项的组合物,其中粘度调节剂选自一-、二-和三-9,9-二取代芴;亚芴基和三芴基苯。
6、权利要求5的组合物,其中粘度调节剂选自1,2,4-三(9,9-二丁基芴)苯和1,3,5-三(9,9-二丁基芴)苯。
7、权利要求1到6任何一项的组合物,其中聚合物包含选自下列的单体的结构单元:9,9-二取代芴、2-甲氧基-5-(2’-乙基己基)亚苯基亚乙烯基;2,5-二辛氧基-1,4-亚苯基亚乙烯基;2-甲硅烷基-1,4-亚苯基亚乙烯基;2,5-二甲硅烷基-1,4-亚苯基亚乙烯基;3-烷基噻吩;2,5-二烷基-1,4-亚苯基亚乙烯基;2,5-二烷氧基亚苯基;2,5-二烷基亚苯基;和N-乙烯基咔唑。
8、权利要求1到7任何一项的组合物,其中聚合物包含第一单体和第二单体的结构单元,所述第一单体选自9,9-二烷基芴、9,9-二芳基芴和9,9-二芳烷基芴,所述第二单体选自取代和未取代的噻吩、二噻吩、苯并二噻唑、噁唑、噁二唑、苯并噁唑、二苯并呋喃、苯并噻吩、二苯并噻吩、dibenzosiloles、联苯胺、二芳基胺、三芳基胺、苯、亚联苯基、萘、蒽、菲、苯乙烯、喹啉和1,2-二苯乙烯。
9、一种组合物,其包含以下的共混物,
a)重均分子量(Mw)至少为20,000的发光聚合物,和
b)粘度调节剂,所述粘度调节剂
1)在室温下是固体;
2)Mw小于5000;
3)发光发射最大值为350到480nm;
4)基本上不减小调节剂和聚合物的组合的电荷输送性质;和
5)不含环外共轭双键;以及
c)用于发光聚合物和粘度调节剂的溶剂,该溶剂选自甲苯、环己基苯、二甲苯、1,3,5-三甲基苯、1,2,3,4-四氢化萘、苯甲酸甲酯、异丙基联苯和茴香醚,
其中共混物中调节剂和聚合化合物的相对量使得共混物表现出在单独的聚合物的发光发射最大值10nm以内的发光发射最大值。
10、权利要求9的组合物,其中发光聚合物包含9,9-二取代芴和选自联苯胺二噻吩和苯并噻二唑的单体的结构单元,其中9,9-二取代芴的结构单元包括在9,9-位上的取代基,所述取代基选自C4-C12烷基、C4-C12-烷氧基,取代的苯基、未取代的苯基、取代的联苯基和未取代的联苯基。
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- 2004-05-17 CN CNA2004800137367A patent/CN1791656A/zh active Pending
- 2004-05-17 DE DE112004000838T patent/DE112004000838T5/de not_active Ceased
- 2004-05-17 JP JP2006533171A patent/JP4465484B2/ja not_active Expired - Fee Related
- 2004-05-17 US US10/847,525 patent/US20040232385A1/en not_active Abandoned
- 2004-05-20 TW TW093114245A patent/TWI349695B/zh not_active IP Right Cessation
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Cited By (4)
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CN103080226A (zh) * | 2010-05-27 | 2013-05-01 | 康宁股份有限公司 | 聚合稠合噻吩半导体制剂 |
US8916066B2 (en) | 2010-05-27 | 2014-12-23 | Corning Incorporated | Polymeric fused thiophene semiconductor formulation |
CN103080226B (zh) * | 2010-05-27 | 2015-04-08 | 康宁股份有限公司 | 聚合稠合噻吩半导体制剂 |
CN102504804A (zh) * | 2011-09-29 | 2012-06-20 | 中国科学院长春应用化学研究所 | 一种利用抑制边缘流动改善喷墨打印薄膜均匀性的有机发光材料溶液及其制备方法 |
Also Published As
Publication number | Publication date |
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WO2004106458A1 (en) | 2004-12-09 |
JP4465484B2 (ja) | 2010-05-19 |
DE112004000838T5 (de) | 2006-03-30 |
TWI349695B (en) | 2011-10-01 |
KR20060013664A (ko) | 2006-02-13 |
KR101142648B1 (ko) | 2012-05-10 |
US20040232385A1 (en) | 2004-11-25 |
US7517472B2 (en) | 2009-04-14 |
TW200427819A (en) | 2004-12-16 |
JP2007505204A (ja) | 2007-03-08 |
US20060197059A1 (en) | 2006-09-07 |
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