Zobrazit v EDS

Organic electronic material and use of same

Uloženo v:
Podrobná bibliografie
Název: Organic electronic material and use of same
Patent Number: 11508,909
Datum vydání: November 22, 2022
Appl. No: 16/489777
Application Filed: February 28, 2018
Abstrakt: An organic electronic material containing a charge transport compound having at least one of the structural regions represented by formulas (1), (2) and (3) shown below. In the formulas, Ar represents an arylene group or heteroarylene group of 2 to 30 carbon atoms, a represents an integer of 1 to 6, b represents an integer of 2 to 6, c represents an integer of 2 to 6, and X represents a substituted or unsubstituted polymerizable functional group. —Ar—O—(CH2)a—O—CH2—X  (1) —Ar—(CH2)b—O—CH2—X  (2) —Ar—O—(CH2)c—X  (3)
Inventors: HITACHI CHEMICAL COMPANY, LTD. (Tokyo, JP)
Assignees: Showa Denko Materials Co., Ltd. (Tokyo, JP)
Claim: 1. An organic electronic material comprising a charge transport compound having a divalent structural unit, a trivalent or higher structural unit, and a monovalent structural unit represented by formula (3) shown below: —Ar—O—(CH 2) c —X  (3) wherein Ar represents an arylene group or heteroarylene group of 2 to 30 carbon atoms, c represents an integer of 5 to 6, and X represents a substituted or unsubstituted polymerizable functional group, wherein the polymerizable functional group comprises at least one group selected from an oxetane group, epoxy group, vinyl group, acryloyl group and methacryloyl group substituted with a saturated alkyl group with 1 to 4 carbon atoms or an unsubstituted oxetane group, epoxy group, vinyl group, acryloyl group and methacryloyl group, wherein a proportion of the trivalent or higher structural unit based on a total of all the structural units is at least 1 mol % and not more than 50 mol %, and wherein a thermal weight reduction upon heating at 300° C. of the charge transport compound is not more than 3.5% by mass relative to a mass of the charge transport compound prior to heating.
Claim: 2. The organic electronic material according to claim 1 , wherein the structural unit represented by the formula (3) comprises a structure represented by formula 3-1 shown below: [chemical expression included] wherein c represents an integer of 5 to 6, and R represents a methyl group or an ethyl group.
Claim: 3. The organic electronic material according to claim 1 , wherein the charge transport compound has hole injection properties.
Claim: 4. The organic electronic material according to claim 1 , wherein the charge transport compound contains at least one structure selected from the group consisting of aromatic amine structures, carbazole structures, thiophene structures, benzene structures, phenoxazine structures and fluorene structures.
Claim: 5. The organic electronic material according to claim 1 , wherein a molar ratio between the divalent structural unit, the monovalent structural unit, and the trivalent or higher structural unit is 100:(10 to 200):(10 to 100).
Claim: 6. An ink composition comprising the organic electronic material according to claim 1 , and a solvent.
Claim: 7. An organic layer formed using the organic electronic material according to claim 1 .
Claim: 8. An organic electronic element comprising the organic layer according to claim 7 .
Claim: 9. An organic electroluminescent element comprising the organic layer according to claim 7 .
Claim: 10. A display element comprising the organic electroluminescent element according to claim 9 .
Claim: 11. An illumination device comprising the organic electroluminescent element according to claim 9 .
Claim: 12. A display device comprising the illumination device according to claim 11 , and a liquid crystal element as a display unit.
Claim: 13. An organic layer formed using the ink composition according to claim claim 6 .
Claim: 14. An organic electronic element comprising the organic layer according to claim 13 .
Claim: 15. An organic electroluminescent element comprising the organic layer according to claim 13 .
Claim: 16. A display element comprising the organic electroluminescent element according to claim 15 .
Claim: 17. An illumination device comprising the organic electroluminescent element according to claim 15 .
Claim: 18. A display device comprising the illumination device according to claim 17 , and a liquid crystal element as a display unit.
Claim: 19. The organic electronic material according to claim 1 , wherein a proportion of the monovalent structural unit represented by formula (3) based on a total of all monovalent structural units is at least 50 mol %.
Patent References Cited: 2004/0170863 September 2004 Kim
2008/0149923 June 2008 Ohsawa
2009/0278445 November 2009 Jen et al.
2009/0321723 December 2009 Hoshi
2011/0198573 August 2011 Iida
2012/0074360 March 2012 Funyuu et al.
2013/0200337 August 2013 Koichiro et al.
2014/0084279 March 2014 Tanaka et al.
2015/0364718 December 2015 Huang
2016/0329497 November 2016 Radu et al.
101616957 December 2009
102791768 November 2012
107078227 August 2017
109937490 June 2019
3106485 December 2016
2000-036390 February 2000
2003-213002 July 2003
2005-075948 March 2005
2006-279007 October 2006
2007-302886 November 2007
2008-063327 March 2008
2008-179790 August 2008
2008-198989 August 2008
2009-536656 October 2009
2009-283509 December 2009
2010-065213 March 2010
2010-155985 July 2010
2012-158669 August 2012
2013-036023 February 2013
2013-045986 March 2013
2013-124271 June 2013
2013-214565 October 2013
2014-019755 February 2014
2014-169418 September 2014
2015-017231 January 2015
2015-035629 February 2015
2015-159077 September 2015
2016-167570 September 2016
2014-0015385 February 2014
201105703 February 2011
201139558 November 2011
201615687 May 2016
2008/010487 January 2008
2008/108162 September 2008
2011/099531 August 2011
2010/140553 November 2012
2013/002053 January 2013
2016/076375 May 2016
2017/079042 May 2017
Other References: Envin Bacher et al., “Photopatteming of Crosslinkable Hole-Conducting Materials for Application in Organic Light-Emitting Devices”, Macromolecular Rapid Communications, 2004, pp. 1191-1196 XP-002636876 (cited in an search report in counterpart European Patent Application No. 17789309.6 dated Jan. 2, 2020). cited by applicant
Md. A. Karim et al., “Synthesis and Characterization of Spirobifluorene-Based Polymers for Organic Light-Emitting Diode Applications”, Macromolecular Research, vol. 16, No. 4, pp. 337-344 (2008) (cited in an search report in counterpart European Patent Application No. 17789309.6 dated Jan. 2, 2020). cited by applicant
Steffen Jungermann et al., “NovelPhoto-Cross-LinkableHole-TransportingPolymers: Synthesis, Characterization, and Application in Organic Light Emitting Diodes”, Macromolecules 2006, vol. 39, No. 26, pp. 8911-8919 (cited in an search report in counterpart European Patent Application No. 17789309.6 dated Jan. 2, 2020). cited by applicant
Kango Hirose et al., 53rd Meeting of the Japan Society of Applied Physics and Related Societies, 26p-ZK-4 (2006). cited by applicant
Md. Anwarul Karim et al., Synthesis and Characterization of Spirobifluorene-Based Polymers for Organic Light-Emitting Diode Applications, Macromolecular Research, vol. 16, No. 4, pp. 337-344, 2008 (cited in a Search Report in counterpart European Appln. dated Jul. 2, 2020). cited by applicant
Steffen Jungermann et al., Articles, NovelPhoto-Cross-LinkableHole-TransportingPolymers:Synthesis, Characterization, and Application in Organic Light Emitting Diodes, Macromolecules 2006, 39, 8911-8919 (cited in a Search Report in counterpart European Appln. dated Jul. 2, 2020). cited by applicant
Database WPI, Week 201420, Thomson Scientific, London, GB; AN 2014-C36254, XP002796440, (cited in a Search Report in counterpart European Appln. dated Jul. 2, 2020). cited by applicant
Database WPI, Week 201316, Thomson Scientific, London, GB; AN 2013-C49055, XP002796441 (cited in a Search Report in counterpart European Appln. dated Jul. 2, 2020). cited by applicant
Endo, A., Ogasawara, M., Takahashi, A., Yokoyama, D., Kato, Y. and Adachi, C. (2009), Thermally Activated Delayed Fluorescence from Sn4+-Porphyrin Complexes and Their Application to Organic Light Emitting Diodes—A Novel Mechanism for Electroluminescence. Adv. Mater., 21: 4802-4806. doi:10.1002/adma.200900983 (Cited in Specification). cited by applicant
Endo, A., Sato, K., Yoshimura, K., Kai, T., Kawada, A., et al. (2011) Efficient up-conversion of triplet excitons into a singlet state and its application for organic light emitting diodes. Appl. Phys. Lett. 98, 083302 ; doi: 10.1063/1.3558906 (Cited in Specification). cited by applicant
Nakagawa, T., Ku, S., Wong, K., Adachi, C. Electroluminescence based on thermally activated delayed fluorescence generated by a spirobifluorene donor-acceptor structure. Chem. Commun., 48, 9580-9582 (2012) (Cited in Specification). cited by applicant
Lee, S., Yasuda, T., Nomura, H., and Adachi, C. High-efficiency organic light-emitting diodes utilizing thermally activated delayed fluorescence from triazine-based donor-acceptor hybrid molecules Appl. Phys. Lett. 101, 093306 (2012); doi: 10.1063/1.4749285 (Cited in Specification). cited by applicant
Zhang, Q., Li, J., Shizu, K,. Huang, S., Hirata, S., Miyazaki, H., and Adachi, C. Design of Efficient Thermally Activated Delayed Fluorescence Materials for Pure Blue Organic Light Emitting Diodes. J. Am. Chem. Soc., 134, 14706 (2012) (Cited in Specification). cited by applicant
Tanaka, H., Shizu, K., Miyazakiab, H., and Adachi, C. Efficient green thermally activated delayed fluorescence (TADF) from a phenoxazine-triphenyltriazine (PXZ-TRZ) derivative. Chem. Comm., 48, 11392 (2012) (Cited in Specification). cited by applicant
Uoyama, H., Goushi, K., Shizu, K., Nomura, H., and Adachi, C. Highly efficient organic light-emitting diodes from delayed fluorescence. Nature, 492, 234 (2012) (Cited in Specification). cited by applicant
Li, J., Nakagawa, T., MacDonald, J., Zhang, Q., Nomura, H., Miyazaki, H., and Adachi, C. Highly Efficient Organic Light-Emitting Diode Based on a Hidden Thermally Activated Delayed Fluorescence Channel in a Heptazine Derivative. Adv. Mater., 25, 3319 (2013) (Cited in Specification). cited by applicant
Ishimatsu, R., Matsunami, S., Shizu, K., Adachi, C., Nakano, K., and Imato, T. Solvent Effect on Thermally Activated Delayed Fluorescence by 1,2,3,5-Tetrakis(carbazol-9-yl)-4,6-dicyanobenzene J. Phys. Chem. A, 117, 5607 (2013) (Cited in Specification). cited by applicant
Serevicius, T., Nakagawa, T., Kuo, M., Cheng, S., Wong, K., Chang, C., Kwong, R. C., Xiae, S., and Adachi, C. Enhanced electroluminescence based on thermally activated delayed fluorescence from a carbazole-triazine derivative. Phys. Chem. Chem. Phys., 15, 15850 (2013) (Cited in Specification). cited by applicant
Nasu, K., Nakagawa, T., Nomura, H., Lin, C., Cheng, C., Tseng, M., Yasudaad, T., and Adachi, C. A highly luminescent spiro-anthracenone-based organic light-emitting diode exhibiting thermally activated delayed fluorescence Chem. Comm., 49, 10385 (2013) (Cited in Specification). cited by applicant
Li, B., Nomura, H., Miyazaki, H., Zhang, Q., Yoshida, K., Suzuma, Y., Orita, A., Otera, J., Adachi, C. Dicarbazolyldicyanobenzenes as Thermally Activated Delayed Fluorescence Emitters: Effect of Substitution Position on Photoluminescent and Electroluminescent Properties. Chem. Lett., 43, 319 (2014) (Cited in Specification). cited by applicant
Primary Examiner: Fang, Shane
Attorney, Agent or Firm: Fitch, Even, Tabin & Flannery, LLP
Přístupové číslo: edspgr.11508909
Databáze: USPTO Patent Grants
Popis
Abstrakt:An organic electronic material containing a charge transport compound having at least one of the structural regions represented by formulas (1), (2) and (3) shown below. In the formulas, Ar represents an arylene group or heteroarylene group of 2 to 30 carbon atoms, a represents an integer of 1 to 6, b represents an integer of 2 to 6, c represents an integer of 2 to 6, and X represents a substituted or unsubstituted polymerizable functional group. —Ar—O—(CH2)a—O—CH2—X  (1) —Ar—(CH2)b—O—CH2—X  (2) —Ar—O—(CH2)c—X  (3)