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(12) United States Patent (10) Patent No.: US 9.482,970 B2 Nauka Et Al

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(12) United States Patent (10) Patent No.: US 9.482,970 B2 Nauka Et Al US00948297OB2 (12) United States Patent (10) Patent No.: US 9.482,970 B2 Nauka et al. (45) Date of Patent: Nov. 1, 2016 (54) ORGANIC PHOTOCONDUCTORS HAVING (56) References Cited PROTECTIVE COATINGS WITH NANOPARTICLES U.S. PATENT DOCUMENTS 4,990,418 A 2f1991 Mukoh et al. (75) Inventors: Krzysztof Nauka, Palo Alto, CA (US); 5,476,604 A 12/1995 Nguyen et al. Zhang-Lin Zhou, Palo Alto, CA (US); 5,882,814 A 3, 1999 Fuller et al. Lihua Zhao, Sunnyvale, CA (US) 6,068,957 A 5, 2000 Nair et al. 6,326, 111 B1 12/2001 Chambers et al. Assignee: Hewlett-Packard Development 6,830,858 B2 12/2004 Sugino et al. (73) 6,902,857 B2 6/2005 Yagi et al. Company, L.P., Houston, TX (US) 7,115,346 B2 10/2006 Yokota et al. 7,122.283 B2 10/2006 Qi et al. (*) Notice: Subject to any disclaimer, the term of this 7,132,208 B2 11/2006 Lee et al. patent is extended or adjusted under 35 7,361,438 B2 4/2008 Suzuki et al. U.S.C. 154(b) by 0 days. (Continued) (21) Appl. No.: 14/373,581 FOREIGN PATENT DOCUMENTS (22) PCT Fed: Mar. 30, 2012 EP 2028.549 2, 2009 JP HO8262779 10, 1996 (86) PCT No.: PCT/US2012/03 1559 (Continued) S 371 (c)(1), (2), (4) Date: Jul. 21, 2014 OTHER PUBLICATIONS (87) PCT Pub. No.: WO2O13A147864 PCT International Search Report, Nov. 30, 2012, Application No. PCT/US2012/03 1559 (filed Mar. 30, 2012). PCT Pub. Date: Oct. 3, 2013 (65) Prior Publication Data Primary Examiner — Christopher Rodee (74) Attorney, Agent, or Firm — HP Inc. Patent US 2014/O349227 A1 Nov. 27, 2014 Department (51) Int. C. ABSTRACT GO3G 5/47 (2006.01) (57) (52) U.S. C. An organic photoconductor includes: a conductive Substrate; CPC .......... G03G 5/14726 (2013.01); G03G 5/147 a charge generation layer formed on the conductive Sub (2013.01); G03G 5/14704 (2013.01); G03G strate; a charge transport layer formed on the charge gen 5/14786 (2013.01); G03G 5/14791 (2013.01); eration layer, and a protective coating formed on the charge G03G 2215/00957 (2013.01) transport layer. The protective coating comprises nanopar (58) Field of Classification Search ticles incorporated in an in-situ cross-linked polymer matrix. CPC ..................... G03G 5/14704: G03G 5/14734; A process for increasing mechanical strength in an organic G03G 5/14739; G03G 5/14726 photoconductor is also provided. USPC ................................................... 430/66, 58.7 See application file for complete search history. 12 Claims, 3 Drawing Sheets 30 -128 12 N-124 2-122 US 9,482,970 B2 Page 2 (56) References Cited 2009.0053637 A1 2/2009 Lin et al. 2009/0092914 A1 4, 2009 Wu et al. U.S. PATENT DOCUMENTS 2009/0148182 A1 6/2009 Watanabe et al. 2009,0185821 A1* 7/2009. Iwamoto .............. GO3G 5,0535 7,413,835 B2 8/2008 Lin et al. 430, 58.7 7,645,555 B2 1/2010 Lin et al. 2010.0167193 A1 7, 2010 Nukada et al. 7,691.931 B2 4/2010 Li et al. 2010, 0215405 A1 8, 2010 Patton et al. 9: R: 29 Aal 2010.0260513 A1 10, 2010 Kawasaki et al. J. W. J. ck 2010/0297.543 Al 11/2010 Tong et al. 2005/0233235 A1* 10/2005 Qi .................... G03:59: 2011/0039 197 A1 2/2011 Fujita et al. 2005/0287452 All 12/2005 Tamura et al. 2005/0287.465 A1 12, 2005 Ohshima et al. FOREIGN PATENT DOCUMENTS 2006/0286473 A1 12, 2006 Kami 2007/0042281 A1 2/2007 Orito et al. JP 9006035 1, 1997 2007/01 17033 A1 5/2007 Sugino et al. JP O9034154 2, 1997 2007/0166634 A1 7/2007 Qi et al. JP 2002311612 10, 2002 2008/0145781 A1* 6/2008 Tong .................... GO3G 5,0535 WO WO-2010 104513 9, 2010 430,270.1 WO WO-2012115650 8, 2012 2009.0035672 A1 2/2009 Yanagawa et al. 2009/0047588 A1 2/2009 Yanus et al. * cited by examiner U.S. Patent Nov. 1, 2016 Sheet 1 of 3 US 9,482,970 B2 O2 Fig. A 28 26 N-124 2-122 Fig. 18 U.S. Patent Nov. 1, 2016 Sheet 2 of 3 US 9,482,970 B2 SCratch Depth 204 O 100 200 300 400 500 600 202 Distance (Lm) Fig. 2 U.S. Patent Nov. 1, 2016 Sheet 3 of 3 US 9,482,970 B2 300 \, 304 Tip Load 302 Fig. 3 US 9,482,970 B2 1. 2 ORGANIC PHOTOCONDUCTORS HAVING herein is used for the purpose of describing particular PROTECTIVE COATINGS WITH examples only. The terms are not intended to be limiting NANOPARTICLES because the scope of the present disclosure is intended to be limited only by the appended claims and equivalents thereof. BACKGROUND It is noted that, as used in this specification and the appended claims, the singular forms “a,” “an,” and “the An organic photoconductor (OPC) is one of the compo include plural referents unless the context clearly dictates nents in an electrophotographic (EP) printer. A latent image, otherwise. which is a surface charge pattern, is created on the OPC prior As used herein, “about” means a +10% variance caused to contact with a development system containing charged 10 by, for example, variations in manufacturing processes. marking particles. This is accomplished by uniformly charg As used herein, “alkyl refers to a branched, unbranched, ing the OPC surface, followed by selective illumination that or cyclic Saturated hydrocarbon group, which typically, locally generates opposite charges within the bulk of the although not necessarily, includes from 1 to 50 carbon OPC which then move to the surface and locally neutralize atoms, or 1 to 30 carbon atoms, or 1 to 6 carbons, for deposited charges. The OPC frequently has two layers: an 15 example. Alkyls include, but are not limited to, methyl, inner layer for generating charges (charge generation ethyl, n-propyl, isopropyl. n-butyl, isobutyl, t-butyl, octyl, layer—CGL) and an outer layer containing molecular moi and decyl, for example, as well as cycloalkyl groups such as eties for facilitating charge movement (charge transport cyclopentyl, and cyclohexyl, for example. layer CTL). In the ideal case, the OPC element has very As used herein, “aryl” refers to a group including a single uniform and defect-free structural and electrical character aromatic ring or multiple aromatic rings that are fused istics. Its usable lifetime is often determined by the occur together, directly linked, or indirectly linked (such that the rence of physical defects introduced by mechanical, physi different aromatic rings are bound to a common group Such cochemical, and electrical interactions between the Surface as a methylene or ethylene moiety). Aryl groups described of the CTL and one or more elements of the electrophoto herein may include, but are not limited to, from 5 to about graphic process (commonly known as “OPC wear-out”). 25 50 carbon atoms, or 5 to about 40 carbon atoms, or 5 to 30 Some of the proposed solutions addressing this issue involve carbon atoms or more. Aryl groups include, for example, coating the CTL Surface with a hard, inorganic film that may phenyl, naphthyl, anthryl, phenanthryl, biphenyl, dipheny significantly raise the OPC cost and introduce other delete lether, diphenylamine, and benzophenone. The term “sub rious effects associated with the contamination particles stituted aryl” refers to an aryl group comprising one or more originating from the inorganic coating. 30 substituent groups. The term "heteroaryl refers to an aryl Alternative solutions have proposed coating the OPC with group in which at least one carbon atom is replaced with a an organic coating having Superior damage resistance and heteroatom. If not otherwise indicated, the term “aryl” electrical properties corresponding to the original OPC. This includes unsubstituted aryl, substituted aryl, and heteroaryl. might be accomplished by using a mixture of damage As used herein, 'substituted” means that a hydrogen atom resistant polymer (matrix) and molecular moieties (CTM 35 of a compound or moiety is replaced by another atom Such charge transport material) providing electrical charge con as a carbon atom or a heteroatom, which is part of a group duction, and coating the original OPC with their solvent referred to as a substituent. Substituents include, but are not based mixture. This solution has not been successful due to limited to, for example, alkyl, alkoxy, aryl, aryloxy, alkenyl, a lack of appropriate hole-conducting dopants that can be alkenoxy, alkynyl, alkynoxy, thioalkyl, thioalkenyl, thio used with a solvent that does not attack the original OPC. All 40 alkynyl, and thioaryl. commonly-available hole-CTMs require solvents that are As used herein, “alcohol means a lower alkyl chain incompatible with the polymeric matrix components used alcohol. Such as methanol, ethanol, n-propanol, iso-propa for most of the commercial OPCs. nol, n-butanol, iso-butanol, tert-butanol, pentanol, hexanol, and their analogs. BRIEF DESCRIPTION OF THE DRAWINGS 45 As used herein, a plurality of items, structural elements, compositional elements, and/or materials may be presented FIG. 1A is a schematic diagram of an apparatus that in a common list for convenience. However, these lists employs an example organic photoconductor (OPC) drum, should be construed as though each member of the list is in accordance with the teachings herein. individually identified as a separate and unique member. FIG. 1B is an enlargement of a portion of the OPC drum 50 Thus, no individual member of such list should be construed of FIG. 1A. as a de facto equivalent of any other member of the same list FIG.
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