Polymer, composition for organic electroluminescent element, organic electroluminescent element, organic EL display device, organic EL lighting, and manufacturing method for organic electroluminescent element
地域：
Tokyo
摘要
Provided are: a highly durable polymer having a high hole-injection/transport capacity; and a composition for an organic electroluminescent element, which contains the polymer. The polymer contains a repeating unit represented by the following Formula (1) or a repeating unit represented by the following Formula (2) (wherein, Ar1 and Ar2 each represent an aromatic hydrocarbon group optionally having a substituent, or an aromatic heterocyclic group optionally having a substituent; X represents —C(R7)(R8)—, —N(R9)—, or —C(R11)(R12)—C(R13)(R14)—; R1 and R2 as well as R3 and R6 each independently represent an alkyl group optionally having a substituent; R4 and R5 each independently represent an alkyl group optionally having a substituent, an alkoxy group optionally having a substituent, or an aralkyl group optionally having a substituent; and R7 to R9 and R11 to R14 each independently represent hydrogen, an alkyl group optionally having a substituent, an aralkyl group optionally having a substituent, or an aromatic hydrocarbon group optionally having a substituent).
說明書
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This is a continuation of U.S. application Ser. No. 17/022,243 filed Sep. 16, 2020, which is a continuation of International Application PCT/JP2019/011229, filed on Mar. 18, 2019 and designated the U.S., and claims priority from Japanese Patent Application 2018-048724 which was filed on Mar. 16, 2018, Japanese Patent Application 2018-083826 which was filed on Apr. 25, 2018 and Japanese Patent Application 2019-021417 which was filed on Feb. 8, 2019, the entire contents of which are incorporated herein by reference.
The present invention relates to: a polymer, more particularly a polymer useful as a charge transporting material of an organic electroluminescent element; a composition for an organic electroluminescent element, which contains the polymer; an organic electroluminescent element including a layer formed from the composition; an organic EL display device and an organic EL lighting, which include the organic electroluminescent element; and a method of producing an organic electroluminescent element.
權(quán)利要求
The invention claimed is:1. A polymer, comprising a repeating unit represented by the following Formula (2): ![embedded image]()
wherein, in Formula (2), Ar2 represents an aromatic hydrocarbon group optionally having a substituent, or an aromatic heterocyclic group optionally having a substituent; at least one Ar2 is represented by the following Formula (10); R3 and R6 each independently represent an alkyl group optionally having a substituent; R4 and R5 each independently represent an alkyl group optionally having a substituent, an alkoxy group optionally having a substituent, or an aralkyl group optionally having a substituent; l represents 0 or 1; m represents 1 or 2; n represents 0 or 1; p represents 0 or 1; q represents 0 or 1; and p and q are not 0 simultaneously; ![embedded image]()
wherein, in Formula (10), Ar11 and Ar12 each independently represent a divalent aromatic hydrocarbon group optionally having a substituent, or an aromatic heterocyclic group optionally having a substituent; Ar13 to Ar15 each independently represent a hydrogen atom or a substituent; and * represents a binding position. 2. The polymer according to claim 1 , whereinat least one Ar2 is a 2-fluorenyl group optionally having a substituent. 3. The polymer according to claim 1 , whereinAr12 is a divalent group or a group constituted by a plurality of the divalent group that are linked together, the divalent group is at least one group selected from the group consisting of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzopyrene ring, a chrysene ring, a triphenylene ring, an acenaphthene ring, a fluoranthene ring, a fluorene ring, a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, an oxadiazole ring, an indole ring, a carbazole ring, a pyrroloimidazole ring, a pyrrolopyrazole ring, a pyrrolopyrrole ring, a thienopyrrole ring, a thienothiophene ring, a furopyrrole ring, a furofuran ring, a thienofuran ring, a benzisoxazole ring, a benzisothiazole ring, a benzimidazole ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinoxaline ring, a phenanthridine ring, a perimidine ring, a quinazoline ring, and a quinazolinone ring. 4. The polymer according to claim 1 , whereinAr12 is a 1,4-phenylene group in which benzene rings are linked at two positions of 1 and 4, a 2,7-fluorenylene group in which fluorene rings are linked at two positions of 2 and 7, or a group constituted by a plurality of these groups that are linked together. 5. The polymer according to claim 1 , whereinAr12 is a group that contains a 1,4-phenylene group, a 2,7-fluorenylene group, and a 1,4-phenylene group-. 6. The polymer according to claim 1 , whereinAr13 to Ar15 are hydrogen atoms. 7. The polymer according to claim 1 , whereinat least one of Ar13 to Ar15 is a substituent group containing a crosslinkable group. 8. The polymer according to claim 1 , whereinAr11 is a 5- or 6-membered monocyclic or 2 to 4-fused-ring divalent group or a group constituted by a plurality of the divalent group that are linked together, the divalent group is at least one group selected from the group consisting of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzopyrene ring, a chrysene ring, a triphenylene ring, an acenaphthene ring, a fluoranthene ring, a fluorene ring, a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, an oxadiazole ring, an indole ring, a carbazole ring, a pyrroloimidazole ring, a pyrrolopyrazole ring, a pyrrolopyrrole ring, a thienopyrrole ring, a thienothiophene ring, a furopyrrole ring, a furofuran ring, a thienofuran ring, a benzisoxazole ring, a benzisothiazole ring, a benzimidazole ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinoxaline ring, a phenanthridine ring, a perimidine ring, a quinazoline ring, and a quinazolinone ring. 9. The polymer according to claim 1 , whereinAr11 contains a 1,3-phenylene group, or a group that contains a substituent and has a distorted structure due to a steric effect of the substituent. 10. The polymer according to claim 1 , further comprising a repeating unit represented by the following Formula (4): ![embedded image]()
wherein, Ar3 represents an aromatic hydrocarbon group optionally having a substituent, or an aromatic heterocyclic group optionally having a substituent; and Ar4 represents a divalent aromatic hydrocarbon group optionally having a substituent, a divalent aromatic heterocyclic group optionally having a substituent, or a divalent group formed by plural aromatic hydrocarbon groups optionally having a substituent and/or plural aromatic heterocyclic groups optionally having a substituent that are linked together directly or via a linking group. 11. The polymer according to claim 10 , wherein at least one Ar3 is represented by the following Formula (10): ![embedded image]()
wherein, Ar11 and Ar12 each independently represent a divalent aromatic hydrocarbon group optionally having a substituent, or an aromatic heterocyclic group optionally having a substituent; Ar13 to Ar15 each independently represent a hydrogen atom or a substituent; and * represents a binding position. 12. The polymer according to claim 11 , whereinAr12 is a group that contains -1,4-phenylene group-2,7-fluorenylene group-1,4-phenylene group-. 13. The polymer according to claim 11 , whereinAr13 to Ar15 are hydrogen atoms. 14. The polymer according to claim 11 , whereinat least one of Ar13 to Ar15 is a substituent group containing a crosslinkable group. 15. The polymer according to claim 11 , whereinAr11 contains a 1,3-phenylene group, or a group that contains a substituent and has a distorted structure due to a steric effect of the substituent. 16. The polymer according to claim 10 , wherein at least one Ar3 is a 2-fluorenyl group optionally having a substituent. 17. The polymer according to claim 10 , further comprising a repeating unit represented by the following Formula (5): ![embedded image]()
wherein, i and j each independently represent an integer of 0 to 3; (i+j) is 1 or larger; k represents 0 or 1; X represents —C(R7)(R8)—, —N(R9)—, or —C(R11)(R12)—C(R13)(R14)—; and R7 to R9 and R11 to R14 each independently represent hydrogen, an alkyl group optionally having a substituent, an aralkyl group optionally having a substituent, or an aromatic hydrocarbon group optionally having a substituent. 18. The polymer according to claim 17 , whereinAr4 in Formula (4) is the repeating unit represented by Formula (5) wherein k is 1, and the repeating unit represented by Formula (5) is linked with N in Formula (4). 19. The polymer according to claim 17 , comprising a repeating unit represented by the following Formula (14): ![embedded image]()
wherein, Ar2, R3, R4, R5, R6, p, q, l, m, n, Ar3, X, i, j, and k are each the same as in Formula (2), (4) or (5). 20. The polymer according to claim 19 , wherein, in Formula (14),X is —C(CH3)(CH3)—, i=j=k=1, and Ar2 and Ar3 are each independently the following Formula (15) or the following Formula (16), with a proviso that Formulae (15) and (16) each optionally have a substituent and * represents a bond with N in Formula (14): ![embedded image]()
21. The polymer according to claim 20 , wherein Formula (15) or (16) has a substituent that is at least one selected from substituents Z and a crosslinkable group,Substituents Z: an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkoxycarbonyl group, a dialkylamino group, a diarylamino group, an arylalkylamino group, an acyl group, a halogen atom, haloalkyl group, an alkylthio group, an arylthio group, an silyl group, an siloxy group, a cyano group, an aromatic hydrocarbon group and an aromatic heterocyclic group; these substituents optionally contain a linear, branched, or cyclic structure. 22. The polymer according to claim 1 , further comprising a repeating unit represented by the following Formula (6): ![embedded image]()
wherein, t represents an integer of 1 to 10; R15 and R16 each independently represent a hydrogen atom, an alkyl group optionally having a substituent, an aromatic hydrocarbon group optionally having a substituent, or an aromatic heterocyclic group optionally having a substituent; and when there are plural R15s and R16s, the R15s and the R16s are optionally the same or different. 23. The polymer according to claim 1 , further comprising a repeating unit represented by the following Formula (7): ![embedded image]()
wherein, Ar5 represents an aromatic hydrocarbon group optionally having a substituent, or an aromatic heterocyclic group optionally having a substituent; R17 to R19 each independently represent an alkyl group optionally having a substituent, an alkoxy group optionally having a substituent, an aralkyl group optionally having a substituent, an aromatic hydrocarbon group optionally having a substituent, or an aromatic heterocyclic group optionally having a substituent; f, g, and h each independently represent an integer of 0 to 4, with (f+g+h) being 1 or larger; and e represents an integer of 0 to 3. 24. The polymer according to claim 23 , whereinthe repeating unit represented by the following Formula (7) is a repeating unit represented by the following Formula (8): ![embedded image]()
where, Ar5, R17 to R19, f, g, h and e are same as the Formula (7). 25. The polymer according to claim 24 , whereinthe repeating unit represented by the following Formula (8) is a repeating unit represented by the following Formula (9): ![embedded image]()
where, Ar5, R17 to R19, f, g, and h are same as the Formula (7). 26. The polymer according to claim 1 , wherein a terminal group of the polymer is an aromatic hydrocarbon group optionally having a substituent composed of a hydrocarbon. 27. The polymer according to claim 1 , comprising a crosslinkable group as a substituent. 28. The polymer according to claim 27 , wherein the crosslinkable group is a group that comprises a cyclobutene ring condensed with an aromatic ring, or an alkenyl group bound to an aromatic ring. 29. The polymer according to claim 1 , having a weight-average molecular weight (Mw) of not less than 10,000, and a degree of dispersion (Mw/Mn) of 3.5 or lower. 30. A composition for an organic electroluminescent element, comprising the polymer according to claim 1 . 31. A composition for an organic electroluminescent element, comprising:the polymer according to claim 1 ; and an organic solvent. 32. A method of producing an organic electroluminescent element that comprises, on a substrate: an anode; a cathode; and organic layers between the anode and the cathode,wherein the method comprises the step of forming at least one of the organic layers by a wet film-forming method using the composition for an organic electroluminescent element according to claim 31 . 33. The method of producing an organic electroluminescent element according to claim 32 , wherein a layer formed by the wet film-forming method is at least one of a hole injection layer and a hole transport layer. 34. The method of producing an organic electroluminescent element according to claim 32 , whereinthe organic electroluminescent element comprises a hole injection layer, a hole transport layer, and a light-emitting layer between the anode and the cathode, and the hole injection layer, the hole transport layer, and the light-emitting layer are all formed by the wet film-forming method. 35. An organic electroluminescent element, comprising a layer that comprises the polymer according to claim 1 , or a polymer obtained by crosslinking the polymer when the polymer contains a crosslinkable group. 36. An organic EL display device, comprising the organic electroluminescent element according to claim 35 . 37. An organic EL lighting, comprising the organic electroluminescent element according to claim 35 .
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