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- Nachgewiesen in: USPTO Patent Grants
- Sprachen: English
- Patent Number: 11800,785
- Publication Date: October 24, 2023
- Appl. No: 16/766378
- Application Filed: November 16, 2018
- Assignees: KWANSEI GAKUIN EDUCATIONAL FOUNDATION (Hyogo, JP), SK MATERIALS JNC CO., LTD. (Gyeonggi-Do, KR)
- Claim: 1. A material for an organic device, comprising a polycyclic aromatic compound represented by formula (1): [chemical expression included] wherein: R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen therein may be replaced by aryl, heteroaryl, alkyl or cycloalkyl, and adjacent groups of R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 may be bonded to each other to form an aryl ring or a heteroaryl ring together with a b ring, a c ring or a d ring, and at least one hydrogen in the ring formed may be replaced by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen therein may be replaced by aryl, heteroaryl, alkyl or cycloalkyl, X 1 is >N—R, R of the >N—R is aryl having 6 to 12 carbons, and at least one hydrogen therein is replaced by aryl having 6 to 12 carbons, heteroaryl having 2 to 15 carbons, alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons, Z 1 and Z 2 are independently aryl, diarylamino, aryloxy, aryl-substituted alkyl, hydrogen or alkyl, and at least one hydrogen therein may be replaced by aryl, alkyl or cycloalkyl, when Z 1 is phenyl which may be substituted by alkyl or cycloalkyl, m-biphenylyl which may be substituted by alkyl or cycloalkyl, p-biphenylyl which may be substituted by alkyl or cycloalkyl, diphenylamino which may be substituted by alkyl or cycloalkyl, hydrogen or alkyl, a case where Z 2 is hydrogen, alkyl or alkoxy is excluded, and at least one hydrogen in the compound represented by formula (1) may be replaced by halogen or deuterium.
- Claim: 2. The material for the organic device according to claim 1 , wherein R 1 , R 3 , R 4 , R 5 ,R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, aryl having 6 to 30 carbons, heteroaryl having 2 to 30 carbons, diarylamino (in which aryl is aryl having 6 to 12 carbons), alkyl having 1 to 6 carbons, cycloalkyl having 3 to 14 carbons, alkoxy having 1 to 6 carbons or aryloxy having 6 to 12 carbons, and at least one hydrogen therein may be replaced by aryl having 6 to 12 carbons, alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons, and adjacent groups of R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 may be bonded to each other to form an aryl ring having 9 to 16 carbons or a heteroaryl ring having 6 to 15 carbons together with a b ring, a c ring or a d ring, and at least one hydrogen in the ring formed may be replaced by aryl having 6 to 30 carbons, heteroaryl having 2 to 30 carbons, diarylamino (in which aryl is aryl having 6 to 12 carbons), alkyl having 1 to 6 carbons, cycloalkyl having 3 to 14 carbons, alkoxy having 1 to 6 carbons or aryloxy having 6 to 12 carbons, X 1 is >N—R, R of the >N—R is aryl having 6 to 12 carbons, and at least one hydrogen therein is replaced by aryl having 6 to 12 carbons, alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons, Z 1 and Z 2 are independently aryl having 6 to 30 carbons, diarylamino (in which aryl is aryl having 6 to 16 carbon), aryloxy having 6 to 30 carbons, alkyl having 1 to 6 carbons in which replacement is made by aryl having 6 to 12 carbons, hydrogen, alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons, and at least one hydrogen therein may be replaced by aryl having 6 to 16 carbons or alkyl having 1 to 6 carbons, when Z 1 is phenyl which may be substituted by alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons, m-biphenylyl which may be substituted by alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons, p-biphenylyl which may be substituted by alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons, diphenylamino which may be substituted by alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons, hydrogen or alkyl having 1 to 6 carbons, a case where Z 2 is hydrogen or alkyl having 1 to 6 carbons is excluded, and at least one hydrogen in the compound represented by formula (1) may be replaced by halogen or deuterium.
- Claim: 3. The material for the organic device according to claim 1 , wherein R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, aryl having 6 to 16 carbons, heteroaryl having 2 to 20 carbons, diarylamino (in which aryl is aryl having 6 to 12 carbons), alkyl having 1 to 6 carbons, cycloalkyl having 3 to 14 carbons, alkoxy having 1 to 6 carbons or aryloxy having 6 to 12 carbons, and adjacent groups of R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 may be bonded to each other to form an aryl ring having 9 to 16 carbons or a heteroaryl ring having 6 to 15 carbons together with a b ring, a c ring or a d ring, and at least one hydrogen in the ring formed may be replaced by aryl having 6 to 16 carbons, heteroaryl having 2 to 20 carbons, diarylamino (in which aryl is aryl having 6 to 12 carbons), alkyl having 1 to 6 carbons, cycloalkyl having 3 to 14 carbons, alkoxy having 1 to 6 carbons or aryloxy having 6 to 12 carbons, X 1 is >N—R, and R of the >N—R is aryl having 6 to 12 carbons, and at least one hydrogen therein is replaced by alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons, Z 1 and Z 2 are independently aryl having 6 to 16 carbons, diarylamino (in which aryl is aryl having 6 to 16 carbon), aryloxy having 6 to 16 carbons, alkyl having 1 to 6 carbons in which at least one hydrogen is replaced by aryl having 6 to 12 carbons, hydrogen or alkyl having 1 to 6 carbons, and at least one hydrogen therein may be replaced by aryl having 6 to 16 carbons, alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons, when Z 1 is phenyl which may be substituted by alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons, m-biphenylyl which may be substituted by alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons, p-biphenylyl which may be substituted by alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons, diphenylamino which may be substituted by alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons, hydrogen or alkyl having 1 to 6 carbons, a case where Z 2 is hydrogen or alkyl having 1 to 6 carbons is excluded, and at least one hydrogen in the compound represented by formula (1) may be replaced by halogen or deuterium.
- Claim: 4. The material for the organic device according to claim 1 , wherein R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are independently hydrogen, aryl having 6 to 16 carbons, heteroaryl having 2 to 20 carbons, diarylamino (in which aryl is aryl having 6 to 12 carbons), alkyl having 1 to 6 carbons, cycloalkyl having 3 to 14 carbons, alkoxy having 1 to 6 carbons or aryloxy having 6 to 12 carbons, and adjacent groups of R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 may be bonded to each other to form a naphthalene ring, a fluorene ring or a carbazole ring together with a b ring, a c ring or a d ring, and at least one hydrogen in the ring formed may be replaced by aryl having 6 to 16 carbons, heteroaryl having 2 to 20 carbons, diarylamino (in which aryl is aryl having 6 to 12 carbons), alkyl having 1 to 6 carbons, cycloalkyl having 3 to 14 carbons, alkoxy having 1 to 6 carbons or aryloxy having 6 to 12 carbons, X 1 is >N—R, and R of the >N—R is aryl having 6 to 12 carbons, and at least one hydrogen therein is replaced by alkyl having 1 to 6 carbons or cycloalkyl having 3 to 14 carbons, Z 1 and Z 2 are independently aryl having 6 to 10 carbons, diarylamino (in which aryl is aryl having 6 to 12 carbon), alkyl having 1 to 4 carbons in which at least one hydrogen therein is replaced by one to three aryl having 6 to 10 carbons, hydrogen, alkyl having 1 to 4 carbons or cycloalkyl having 5 to 10 carbons, and at least one hydrogen therein may be replaced by aryl having 6 to 12 carbons, alkyl having 1 to 4 carbons or cycloalkyl having 5 to 10 carbons, when Z 1 is phenyl which may be substituted by alkyl having 1 to 4 carbons or cycloalkyl having 5 to 10 carbons, m-biphenylyl which may be substituted by alkyl having 1 to 4 carbons or cycloalkyl having 5 to 10 carbons, p-biphenylyl which may be substituted by alkyl having 1 to 4 carbons or cycloalkyl having 5 to 10 carbons, diphenylamino which may be substituted by alkyl having 1 to 4 carbons or cycloalkyl having 5 to 10 carbons, hydrogen or alkyl having 1 to 4 carbons, a case where Z 2 is hydrogen or alkyl having 1 to 4 carbons is excluded, and at least one hydrogen in the compound represented by formula (1) may be replaced by halogen or deuterium.
- Claim: 5. The material for the organic device according to claim 1 , wherein Z 1 is diarylamino, aryloxy, triaryl-substituted alkyl having 1 to 4 carbons, hydrogen, alkyl having 1 to 4 carbons or cycloalkyl having 5 to 10 carbons, and aryl therein is independently phenyl, biphenylyl or naphthyl in which at least one hydrogen therein may be replaced by alkyl having 1 to 4 carbons or phenyl, Z 2 is phenyl, biphenylyl or naphthyl in which at least one hydrogen therein may be replaced by alkyl having 1 to 4 carbons or cycloalkyl having 5 to 10 carbons, or hydrogen, alkyl having 1 to 4 carbons or cycloalkyl having 5 to 10 carbons, and when Z 1 is diphenylamino which may be substituted by alkyl having 1 to 4 carbons or cycloalkyl having 5 to 10 carbons, hydrogen or alkyl having 1 to 4 carbons, a case where Z 2 is hydrogen or alkyl having 1 to 4 carbons is excluded.
- Claim: 6. The material for the organic device according to claim 1 , wherein the polycyclic aromatic compound represented by formula (1) is at least one selected from the group consisting of: [chemical expression included] [chemical expression included] [chemical expression included] [chemical expression included] [chemical expression included] [chemical expression included] [chemical expression included]
- Claim: 7. The material for the organic device according to claim 1 , wherein the material for the organic device is a material for an organic electroluminescent device, a material for an organic field effect transistor or a material for an organic thin film photovoltaic cell.
- Claim: 8. An organic electroluminescent device, comprising a pair of electrodes formed of an anode and a cathode, and a luminescent layer arranged between the anode and the cathode, wherein the luminescent layer comprises the material for the organic device according to claim 1 .
- Claim: 9. The organic electroluminescent device according to claim 8 , wherein the luminescent layer comprises a host and the material for the organic device as a dopant.
- Claim: 10. The organic electroluminescent device according to claim 9 , wherein the host is an anthracene-based compound, a dibenzochrysene-based compound or a fluorene-based compound.
- Claim: 11. The organic electroluminescent device according to claim 8 , having an electron transport layer and/or an electron injection layer which are arranged between the cathode and the luminescent layer, wherein at least one of the electron transport layer and the electron injection layer comprises at least one derivative or complex selected from the group of a borane derivative, a pyridine derivative, a fluoranthene derivative, a BO-based derivative, an anthracene derivative, a benzofluorene derivative, a phosphine oxide derivative, a pyrimidine derivative, a carbazole derivative, a triazine derivative, a benzimidazole derivative, a phenanthroline derivative and a quinolinol-based metal complex.
- Claim: 12. The organic electroluminescent device according to claim 11 , wherein the electron transport layer and/or the electron injection layer further comprises at least one selected from the group of an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, an oxide of an alkaline earth metal, a halide of an alkaline earth metal, an oxide of a rare earth metal, a halide of a rare earth metal, an organic complex of an alkali metal, an organic complex of an alkaline earth metal and an organic complex of a rare earth metal.
- Claim: 13. A display unit or a lighting unit, comprising the organic electroluminescent device according to claim 8 .
- Claim: 14. The material for the organic device according to claim 1 , wherein Z 1 is phenylnaphthylamino or dinaphthylamino in which at least one hydrogen therein may be replaced by aryl, alkyl or cycloalkyl.
- Claim: 15. The material for the organic device according to claim 14 , wherein Z 2 is hydrogen.
- Claim: 16. The material for the organic device according to claim 14 , wherein the polycyclic aromatic compound represented by formula (1) is at least one selected from the group consisting of: [chemical expression included] [chemical expression included]
- Claim: 17. The material for the organic device according to claim 1 , wherein Z 1 is phenylnaphthyamino in which at least one hydrogen therein may be replaced by aryl, alkyl or cycloalkyl.
- Claim: 18. The material for the organic device according to claim 17 , wherein Z 2 is hydrogen.
- Claim: 19. The material for the organic device according to claim 17 , wherein the polycyclic aromatic compound represented by formula (1) is at least one selected from the group consisting of: [chemical expression included] [chemical expression included]
- Claim: 20. The material for the organic device according to claim 1 , wherein the polycyclic aromatic compound represented by formula (1) is at least one selected from the group consisting of: [chemical expression included] [chemical expression included]
- Patent References Cited: 20040131881 July 2004 Zheng et al. ; 20070106103 May 2007 Ikeda et al. ; 20120319052 December 2012 Brocke et al. ; 20140058099 February 2014 Wakamiya et al. ; 20150097162 April 2015 Ono et al. ; 20150236274 August 2015 Hatakeyama ; 20180094000 April 2018 Hatakeyama et al. ; 20180301629 October 2018 Hatakeyama et al. ; 20190058124 February 2019 Hatakeyama ; 104641483 May 2015 ; 105431439 March 2016 ; 106905367 June 2017 ; 3 109 253 December 2016 ; 2001-172232 June 2001 ; 2005-170911 June 2005 ; 201739751 November 2017 ; 2004/061047 July 2004 ; 2010/098119 September 2010 ; 2011/107186 September 2011 ; 2012/118164 September 2012 ; 2015/102118 July 2015 ; 2016/152418 September 2016 ; 2016/152544 September 2016 ; 2017/138526 August 2017 ; 2018/181188 October 2018
- Other References: International Search Report (ISR) dated Feb. 19, 2019 in International (PCT) Application No. PCT/JP2018/042412. cited by applicant ; Office Action dated May 10, 2022 in Japanese Patent Application No. 2019-555285, with English-language translation. cited by applicant ; Office Action dated Nov. 9, 2022 in corresponding Chinese Patent Application No. 201880073800.2, with English language translation. cited by applicant ; Decision to Grant a Patent dated Jan. 10, 2023 in corresponding Japanese Patent Application No. 2019-555285, with English language translation. cited by applicant ; Decision to Grant dated May 10, 2023 in corresponding Chinese Patent Application No. 201880073800.2,with English Translation. cited by applicant
- Primary Examiner: Clark, Gregory D
- Attorney, Agent or Firm: Wenderoth, Lind & Ponack, L.L.P.
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