公开(公告)号：US08859718B2

公开(公告)日：2014-10-14

申请号：US13656561

申请日：2012-10-19

Applicant: Plextronics, Inc.

Inventor： Elena E. Sheina ,  Chad Landis ,  Venkataramanan Seshadri ,  Christopher T. Brown ,  Samuel M. Mazza

IPC: C08G75/06

CPC classification number: A61B8/4427 ,  A61B8/0841 ,  A61B8/0891 ,  A61B8/4455 ,  A61B8/465 ,  A61B34/25 ,  A61B2017/3413 ,  C08G61/124 ,  C08G61/125 ,  C08G61/126 ,  C08G75/06 ,  C08G2261/1424 ,  C08G2261/3222 ,  C08G2261/3223 ,  C08G2261/3241 ,  C08G2261/3243 ,  C08G2261/43

Abstract: An improved polymerization method including a method comprising providing a reaction mixture comprising a first monomer, an organic oxidant, and at least one Lewis acid or Brönsted acid, wherein the first monomer comprises at least one optionally substituted heterocyclic ring, wherein the heterocyclic ring comprises at least one heteroatom; and reacting the reaction mixture to obtain a conjugated polymer. The method can reduce the content of undesirable entities in the polymer such as halogens and metals, which can be useful in organic electronic device applications. Purification methods also are adapted to remove organic and inorganic impurities.

Abstract translation: 一种改进的聚合方法，包括提供包含第一单体，有机氧化剂和至少一种路易斯酸或布朗斯台德酸的反应混合物的方法，其中第一单体包含至少一个任选取代的杂环，其中杂环包含 至少一个杂原子; 并使反应混合物反应，得到共轭聚合物。 该方法可以降低聚合物中不需要的实体的含量，例如卤素和金属，其可用于有机电子器件应用。 净化方法也适用于去除有机和无机杂质。

公开(公告)号：US20130092887A1

公开(公告)日：2013-04-18

申请号：US13573676

申请日：2012-10-03

Applicant: Plextronics, Inc.

Inventor： Venkataramanan Seshadri ,  Neetu Chopra

IPC: H01B1/12

CPC classification number: H01B1/12 ,  C08F12/22 ,  C08F12/24 ,  C08F12/26 ,  C08F226/06 ,  C09D125/18 ,  C09K11/06 ,  C09K2211/1416 ,  C09K2211/1433 ,  C09K2211/1458 ,  C09K2211/1466 ,  C09K2211/1483 ,  H01B1/122 ,  H01B1/127 ,  H01L51/002 ,  H01L51/0059 ,  H01L51/008 ,  H01L51/0081 ,  H01L51/0082 ,  H01L51/506 ,  H05B33/18 ,  Y02E10/549 ,  C08F212/32 ,  C08F212/14

Abstract: A method including combining at least one first compound in a neutral form with at least one ionic dopant in a first solvent system to provide a first doped reaction product, isolating the first doped reaction product in solid form, and combining the isolated first doped reaction product with at least one conjugated polymer in neutral form in a second solvent system to form a second doped reaction product including an oxidized form of the conjugated polymer a neutral form of the first compound. Advantages include better stability, ease of use, and lower metal content. Applications include organic electronic devices including OLEDs.

Abstract translation: 一种方法，包括在第一溶剂系统中将至少一种中性形式的至少一种第一化合物与至少一种离子掺杂剂组合以提供第一掺杂反应产物，分离出固体形式的第一掺杂反应产物，以及将分离的第一掺杂反应产物 与至少一种中性形式的共轭聚合物在第二溶剂体系中形成第二掺杂的反应产物，其包括第一化合物的中性形式的共轭聚合物的氧化形式。 优点包括更好的稳定性，易用性和更低的金属含量。 应用包括有机电子器件，包括OLED。

公开(公告)号：US08815639B2

公开(公告)日：2014-08-26

申请号：US13868924

申请日：2013-04-23

Applicant: Plextronics, Inc.

Inventor： Christopher T. Brown ,  Neetu Chopra ,  Christopher Knittel ,  Mathew Mathai ,  Venkataramanan Seshadri ,  Jing Wang ,  Brian Woodworth

IPC: H01L51/00

CPC classification number: H01L51/0007 ,  C07D403/00 ,  C08F226/02 ,  C08G73/0206 ,  C08G2261/222 ,  C08G2261/312 ,  C08G2261/3142 ,  C08G2261/3162 ,  C08G2261/364 ,  C08G2261/512 ,  C08G2261/76 ,  C09B57/008 ,  C09B69/109 ,  C09D11/102 ,  C09D11/106 ,  C09D11/52 ,  H01B1/12 ,  H01L51/0003 ,  H01L51/0039 ,  H01L51/0043 ,  H01L51/0059 ,  H01L51/006 ,  H01L51/0074 ,  H01L51/5004 ,  H01L51/5056 ,  H01L2251/552

Abstract: A composition comprising: at least one compound comprising a hole transporting core, wherein the core is covalently bonded to a first arylamine group and also covalently bonded to a second arylamine group different from the first, and wherein the compound is covalently bonded to at least one intractability group, wherein the intractability group is covalently bonded to the hole transporting core, the first arylamine group, the second arylamine group, or a combination thereof, and wherein the compound has a molecular weight of about 5,000 g/mole or less. Blended mixtures of arylamine compounds, including fluorene core compounds, can provide good film formation and stability when coated onto hole injection layers. Solution processing of OLEDs is a particularly important application.

Abstract translation: 一种组合物，其包含：至少一种包含空穴传输核心的化合物，其中所述核共价键合到第一芳胺基团并且还共价键合到与第一芳基胺基团不同的第二芳胺基团，并且其中所述化合物共价键合至至少一个 难处理性基团，其中难处理性基团共价键合到空穴传输核心，第一芳基胺基团，第二芳基胺基团或其组合，并且其中该化合物的分子量为约5,000g / mole或更低。 芳基胺化合物（包括芴核心化合物）的混合物可以在涂覆到空穴注入层上时提供良好的成膜和稳定性。 OLED的解决方案处理是一个特别重要的应用。

公开(公告)号：US08716706B2

公开(公告)日：2014-05-06

申请号：US13753262

申请日：2013-01-29

Applicant: Plextronics, Inc.

Inventor： Christopher T. Brown ,  Mathew K. Mathai ,  Venkataramanan Seshadri

IPC: H01L33/00

CPC classification number: H01L51/0036 ,  C08L65/00 ,  C08L65/02 ,  C09D165/00 ,  C09D165/02 ,  H01L51/005 ,  H01L51/006 ,  H01L51/008 ,  H01L51/5052 ,  H01L51/5056 ,  H01L51/5088 ,  Y02E10/549 ,  Y02P70/521 ,  C08L2666/22

Abstract: Compositions for use in hole transporting layers (HTLs) or hole injection layers (HILs) are provided, as well as methods of making the compositions and devices fabricated from the compositions. OLED devices can be made. The compositions comprise at least one conductive conjugated polymer, at least one semiconducting matrix component that is different from the conductive conjugated polymer, and an optional dopant, and are substantially free of an insulating matrix component.

Abstract translation: 提供了用于空穴传输层（HTL）或空穴注入层（HIL）的组合物，以及制备由组合物制备的组合物和装置的方法。 可以制造OLED器件。 组合物包含至少一种导电共轭聚合物，至少一种不同于导电共轭聚合物的半导体基质组分和任选的掺杂剂，并且基本上不含绝缘基质组分。

公开(公告)号：US20130344648A1

公开(公告)日：2013-12-26

申请号：US13868924

申请日：2013-04-23

Applicant: Plextronics, Inc.

Inventor： Christopher T. Brown ,  Neetu Chopra ,  Christopher Knittel ,  Mathew Mathai ,  Venkataramanan Seshadri ,  Jing Wang ,  Brian Woodworth

IPC: H01L51/00

CPC classification number: H01L51/0007 ,  C07D403/00 ,  C08F226/02 ,  C08G73/0206 ,  C08G2261/222 ,  C08G2261/312 ,  C08G2261/3142 ,  C08G2261/3162 ,  C08G2261/364 ,  C08G2261/512 ,  C08G2261/76 ,  C09B57/008 ,  C09B69/109 ,  C09D11/102 ,  C09D11/106 ,  C09D11/52 ,  H01B1/12 ,  H01L51/0003 ,  H01L51/0039 ,  H01L51/0043 ,  H01L51/0059 ,  H01L51/006 ,  H01L51/0074 ,  H01L51/5004 ,  H01L51/5056 ,  H01L2251/552

Abstract: A composition comprising: at least one compound comprising a hole transporting core, wherein the core is covalently bonded to a first arylamine group and also covalently bonded to a second arylamine group different from the first, and wherein the compound is covalently bonded to at least one intractability group, wherein the intractability group is covalently bonded to the hole transporting core, the first arylamine group, the second arylamine group, or a combination thereof, and wherein the compound has a molecular weight of about 5,000 g/mole or less. Blended mixtures of arylamine compounds, including fluorene core compounds, can provide good film formation and stability when coated onto hole injection layers. Solution processing of OLEDs is a particularly important application.

Abstract translation: 一种组合物，其包含：至少一种包含空穴传输核心的化合物，其中所述核共价键合到第一芳胺基团并且还共价键合到与第一芳基胺基团不同的第二芳胺基团，并且其中所述化合物共价键合至至少一个 难处理性基团，其中难处理性基团共价键合到空穴传输核心，第一芳基胺基团，第二芳基胺基团或其组合，并且其中该化合物的分子量为约5,000g / mole或更低。 芳基胺化合物（包括芴核心化合物）的混合物可以在涂覆到空穴注入层上时提供良好的成膜和稳定性。 OLED的解决方案处理是一个特别重要的应用。

公开(公告)号：US20130214257A1

公开(公告)日：2013-08-22

申请号：US13753262

申请日：2013-01-29

Applicant: Plextronics, Inc.

Inventor： Christopher T. Brown ,  Mathew K. Mathai ,  Venkataramanan Seshadri

IPC: H01L51/00

CPC classification number: H01L51/0036 ,  C08L65/00 ,  C08L65/02 ,  C09D165/00 ,  C09D165/02 ,  H01L51/005 ,  H01L51/006 ,  H01L51/008 ,  H01L51/5052 ,  H01L51/5056 ,  H01L51/5088 ,  Y02E10/549 ,  Y02P70/521 ,  C08L2666/22

Abstract: Compositions for use in hole transporting layers (HTLs) or hole injection layers (HILs) are provided, as well as methods of making the compositions and devices fabricated from the compositions. OLED devices can be made. The compositions comprise at least one conductive conjugated polymer, at least one semiconducting matrix component that is different from the conductive conjugated polymer, and an optional dopant, and are substantially free of an insulating matrix component.

Abstract translation: 提供了用于空穴传输层（HTL）或空穴注入层（HIL）的组合物，以及制备由组合物制备的组合物和装置的方法。 可以制造OLED器件。 组合物包含至少一种导电共轭聚合物，至少一种不同于导电共轭聚合物的半导体基质组分和任选的掺杂剂，并且基本上不含绝缘基质组分。

公开(公告)号：US20140217334A1

公开(公告)日：2014-08-07

申请号：US14176951

申请日：2014-02-10

Applicant: Plextronics, Inc.

Inventor： Christopher T. BROWN ,  Mark A. Bower ,  Venkataramanan Seshadri

IPC: H01L51/00

CPC classification number: H01L51/008 ,  C08G61/126 ,  C08G2261/1424 ,  C08G2261/3223 ,  C08G2261/512 ,  C08G2261/792 ,  C08G2261/91 ,  C08G2261/92 ,  C08G2261/94 ,  C08K5/55 ,  C08L65/00 ,  C08L2205/02 ,  Y02E10/549 ,  C08L2666/22

Abstract: Compositions comprising at least one hole transport material, such as a conjugated polymer, and at least one dopant, providing improved thermal stability. Compositions can be applied to substrates and used in HIL and HTL layers and organic electronic devices such as light emitting devices such as OLEDs or OPVs. The conjugated polymer can be a polythiophene, including a 3,4-substituted polythiophene or a regioregular polythiophene. The dopant can be a silver salt such as silver tetrakis(pentafluorophenyl)borate. Improved methods of making dopant are provided.

Abstract translation: 包含至少一种空穴传输材料如共轭聚合物和至少一种掺杂剂的组合物，提供改进的热稳定性。 组合物可以应用于基底并用于HIL和HTL层以及有机电子器件如发光器件如OLED或OPV。 共轭聚合物可以是聚噻吩，包括3,4-取代的聚噻吩或区域性聚噻吩。 掺杂剂可以是银盐如四（五氟苯基）硼酸银。 提供了制备掺杂剂的改进方法。

公开(公告)号：US20140054509A1

公开(公告)日：2014-02-27

申请号：US13768967

申请日：2013-02-15

Applicant: Plextronics, Inc.

Inventor： Venkataramanan Seshadri ,  Brian Woodworth ,  Christopher Greco ,  Darin Laird ,  Mathew Mathai

IPC: H01L51/00

CPC classification number: H01L51/0036 ,  C08G61/126 ,  C08G2261/1424 ,  C08G2261/1452 ,  C08G2261/18 ,  C08G2261/212 ,  C08G2261/3223 ,  C08G2261/43 ,  C08G2261/512 ,  C08G2261/722 ,  C08G2261/79 ,  C08G2261/95 ,  C08L65/00 ,  C09D165/00 ,  H01G9/028 ,  H01G11/48 ,  H01G11/56 ,  H01L51/006 ,  H01L51/0081 ,  H01L51/5048 ,  H01L51/5088 ,  Y02E10/549 ,  Y02E60/13 ,  Y10T428/31504 ,  Y10T428/31533 ,  Y10T428/31678 ,  C08L2666/02

Abstract: Conducting polymer systems for hole injection or transport layer applications including a composition comprising: a water soluble or water dispersible regioregular polythiophene comprising (i) at least one organic substituent, and (ii) at least one sulfonate substituent comprising sulfonate sulfur bonding directly to the polythiophene backbone. The polythiophene can be water soluble, water dispersible, or water swellable. They can be self-doped. The organic substituent can be an alkoxy substituent, or an alkyl substituent. OLED, PLED, SMOLED, PV, and ESD applications can be used.

Abstract translation: 用于空穴注入或传输层应用的导电聚合物体系包括包含以下组合物的组合物：水溶性或水分散性区域性聚噻吩，其包含（i）至少一种有机取代基，和（ii）至少一种磺酸盐取代基，其包含与所述聚噻吩直接结合的磺酸盐 骨干。 聚噻吩可以是水溶性的，水分散的或水可溶胀的。 它们可以是自掺杂的。 有机取代基可以是烷氧基取代基或烷基取代基。 可以使用OLED，PLED，SMOLED，PV和ESD应用。

公开(公告)号：US20130109813A1

公开(公告)日：2013-05-02

申请号：US13656561

申请日：2012-10-19

Applicant: Plextronics, Inc.

Inventor： Elena M. Sheina ,  Chad Landis ,  Venkataramanan Seshadri ,  Christopher T. Brown ,  Samuel M. Mazza

IPC: C08G75/06

CPC classification number: A61B8/4427 ,  A61B8/0841 ,  A61B8/0891 ,  A61B8/4455 ,  A61B8/465 ,  A61B34/25 ,  A61B2017/3413 ,  C08G61/124 ,  C08G61/125 ,  C08G61/126 ,  C08G75/06 ,  C08G2261/1424 ,  C08G2261/3222 ,  C08G2261/3223 ,  C08G2261/3241 ,  C08G2261/3243 ,  C08G2261/43

Abstract: An improved polymerization method including a method comprising providing a reaction mixture comprising a first monomer, an organic oxidant, and at least one Lewis acid or Brönsted acid, wherein the first monomer comprises at least one optionally substituted heterocyclic ring, wherein the heterocyclic ring comprises at least one heteroatom; and reacting the reaction mixture to obtain a conjugated polymer. The method can reduce the content of undesirable entities in the polymer such as halogens and metals, which can be useful in organic electronic device applications. Purification methods also are adapted to remove organic and inorganic impurities.