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US 12,349,592 B2Granted
Compound and photoelectric device, image sensor, and electronic device including the same
AssigneeSamsung Electronics Co., Ltd.
InventorsSeon-Jeong Lim, Norihito Ishii, Katsunori Shibata, Yong Wan Jin, Taejin Choi, Kyung Bae Park, Sung Jun Park, Jisoo Shin, Sung Young Yun
Life of this patent
Estimating the term…
Abstract
A compound of Chemical Formula 1, and an organic photoelectric device, an image sensor, and/or an electronic device including the same are disclosed: In Chemical Formula 1, each substituent is the same as defined in the detailed description.
Claims27
A compound represented by Chemical Formula 1:
- wherein, in Chemical Formula 1,
- Ar1 and Ar2 are independently a substituted or unsubstituted C6 to C30 arene group, or a substituted or unsubstituted C3 to C30 heteroarene group, or a condensed ring thereof,
- X1 is —Se—, —Te—, or —NRa1—, wherein Ra1 is hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group,
- X2 is —O—, —S—, —Se—, —Te—, —S(═O)—, —S(═O)2—, —NRa1—, —BRa2—, —SiRbRc—, —SiRbbRcc—, —GeRdRe—, —GeRddRee—, —(CRfRg)n1—, —(CRffRgg)—, —(C(Rm)═C(Rn))—, —(C(Rmm)═C(Rnn))—, or —(C(Rp)═N))—, wherein Ra1, Ra2, Rb, Rc, Rd, Re, Rf, Rg, Rm, Rn, and Rp are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, and Rbb and Rcc, Rdd and Ree, Rff and Rgg, and Rmm and Rnn are linked with each other to provide a ring structure, and n1 of —(CRfRg)n1— is 1 or 2,
- L is —O—, —S—, —Se—, —Te—, —NRa1—, —BRa2—, —SiRbRc—, —SiRbbRcc—, —GeRdRe—, —GeRddRee—, —(CRfRg)n1—, —(CRffRgg)—, —(C(Rm)═C(Rn))—, —(C(Rmm)═C(Rnn))—, —(C(Rp)═N))—, or a single bond, wherein Ra1, Ra2, Rb, Rc, Rd, Re, Rf, Rg, Rm, Rn, and Rp are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, and Rbb and Rcc, Rdd and Ree, Rff and Rgg, and Rmm and Rnn are linked with each other to provide a ring structure, and n1 of —(CRfRg)n1— is 1 or 2,
- when L is —NRa1—, —BRa2—, —SiRbRc—, —GeRdRe—, —(CRfRg)n1—, —(C(Rm)═C(Rn))—, or —(C(Rp)═N))—, L is optionally linked with Ar1 or Ar2 to provide a ring structure,
- Ar3 is a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group having at least one functional group selected from C═O, C═S, C═Se, and C═Te, or a substituted or unsubstituted C2 to C30 heterocyclic group having at least one functional group selected from C═O, C═S, C═Se, and C═Te, or a fused ring thereof, and
- R1 and R2 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 acyl group, a halogen, a cyano group, a cyano-containing group, a nitro group, a pentafluorosulfanyl group (—SF5), a hydroxyl group, an amine group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, or —SiRaRbRc, wherein Ra, Rb, and Rc are independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group.
5 more elements
A compound represented by Chemical Formula 2B:
- wherein, in Chemical Formula 2B,
- X1 is —Se—, —Te—, or —NRa1—, wherein Ra1 is hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group,
- X2 is —O—, —S—, —Se—, —Te—, —S(═O)—, —S(═O)2—, —NRa1—, —BRa2—, —SiRbRc—, —SiRbbRcc—, —GeRdRe—, —GeRddRee—, —(CRfRe)n1—, —(CRffRgg)—, —(C(Rm)═C(Rn))—, —(C(Rmm)═C(Rnn))—, or —(C(Rp)═N))—, wherein Ra1, Ra2, Rb, Rc, Rd, Re, Rf, Rg, Rm, Rn, and Rp are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, and Rbb and Rcc, Rdd and Ree, Rff and Rgg, and Rmm and Rnn are linked with each other to provide a ring structure, and n1 of —(CRfRg)n1— is 1 or 2,
- Ar3 is a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group having at least one functional group selected from C═O, C═S, C═Se, and C═Te, or a substituted or unsubstituted C2 to C30 heterocyclic group having at least one functional group selected from C═O, C═S, C═Se, and C═Te, or a fused ring thereof,
- R1 and R2 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 acyl group, a halogen, a cyano group, a cyano-containing group, a nitro group, a pentafluorosulfanyl group (—SF5), a hydroxyl group, an amine group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, or —SiRaRbRc, wherein Ra, Rb, and Rc are independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group,
- L is —O—, —S—, —Se—, —Te—, —NRa1—, —BRa2—, —SiRbRc—, —SiRbbRcc—, —GeRdRe—, —GeRddRee—, —(CRfRg)n1—, —(CRffRgg)—, —(C(Rm)═C(Rn))—, —(C(Rmm)═C(Rnn))—, —(C(Rp)═N))—, or a single bond, wherein Ra1, Ra2, Rb, Rc, Rd, Re, Rf, Rg, Rm, Rn, and Rp are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, and Rbb and Rcc, Rdd and Ree, Rff and Rgg, and Rmm and Rnn are linked with each other to provide a ring structure, and n1 of —(CRfRg)n1— is 1 or 2,
- Y1 to Y5 are independently N or CRk, wherein Rk is hydrogen, deuterium, a halogen, a cyano group, a nitro group, a hydroxyl group, an amine group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C1 to C10 alkoxy group, or adjacent Rk's are linked to each other to provide a substituted or unsubstituted C6 to C30 arene group, or a substituted or unsubstituted C3 to C30 heteroarene group, or a condensed ring thereof, and
- X3 is —O—, —S—, —Se—, —Te—, —S(═O)—, —S(═O)2—, —NRa1—, —BRa2—, —SiRbRc—, —SiRbbRcc—, —GeRdRe—, —GeRddRee—, —CRfRg—, or —CRffRgg—, wherein Ra1, Ra2, Rb, Rc, Rd, Re, Rf, and Rg are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, and Rbb and Rcc, Rdd and Ree, and Rff and Rgg are linked to each other to provide a ring structure.
5 more elements
A compound represented by Chemical Formula 2C:
- wherein, in Chemical Formula 2C,
- X1 is —Se—, —Te—, or —NRa1—, wherein Ra1 is hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group,
- X2 is —O—, —S—, —Se—, —Te—, —S(═O)—, —S(═O)2—, —NRa1—, —BRa2—, —SiRbRc—, —SiRbbRcc—, —GeRdRe—, —GeRddRee—, —(CRfRg)n1—, —(CRffRgg)—, —(C(Rm)═C(Rn))—, —(C(Rmm)═C(Rnn))—, or —(C(Rp)═N))—, wherein Ra1, Ra2, Rb, Rc, Rd, Re, Rf, Rg, Rm, Rn, and Rp are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, and Rbb and Rcc, Rdd and Ree, Rff and Rgg, and Rmm and Rnn are linked with each other to provide a ring structure, and n1 of —(CRfRg)n1— is 1 or 2,
- Ar3 is a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group having at least one functional group selected from C═O, C═S, C═Se, and C═Te, or a substituted or unsubstituted C2 to C30 heterocyclic group having at least one functional group selected from C═O, C═S, C═Se, and C═Te, or a fused ring thereof,
- R1 and R2 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 acyl group, a halogen, a cyano group, a cyano-containing group, a nitro group, a pentafluorosulfanyl group (—SF5), a hydroxyl group, an amine group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, or —SiRaRbRc, wherein Ra, Rb, and Rc are independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group,
- L is —O—, —S—, —Se—, —Te—, —NRa1—, —BRa2—, —SiRbRc—, —SiRbbRcc—, —GeRdRe—, —GeRddRee—, —(CRfRe)n1—, —(CRffRgg)—, —(C(Rm)═C(Rn))—, —(C(Rmm)═C(Rnn))—, —(C(Rp)═N))—, or a single bond, wherein Ra1, Ra2, Rb, Rc, Rd, Re, Rf, Rg, Rm, Rn, and Rp are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, and Rbb and Rcc, Rdd and Ree, Rff and Rgg, and Rmm and Rnn are linked with each other to provide a ring structure, and n1 of —(CRfRg)n1— is 1 or 2,
- Y1 to Y5 are independently N or CRk, wherein Rk is hydrogen, deuterium, a halogen, a cyano group, a nitro group, a hydroxyl group, an amine group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C1 to C10 alkoxy group, or adjacent Rk's are linked to each other to provide a substituted or unsubstituted C6 to C30 arene group, or a substituted or unsubstituted C3 to C30 heteroarene group, or a condensed ring thereof, and
- X3 is —O—, —S—, —Se—, —Te—, —S(═O)—, —S(═O)2—, —NRa1—, —BRa2—, —SiRbRc—, —SiRbbRcc—, —GeRdRe—, —GeRddRee—, —CRfRg—, or —CRffRgg—, wherein Ra1, Ra2, Rb, Rc, Rd, Re, Rf, and Rg are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, and Rbb and Rcc, Rdd and Ree, and Rff and Rgg are linked to each other to provide a ring structure.
5 more elements
A compound represented by Chemical Formula 2D:
- wherein, in Chemical Formula 2D,
- X1 is —Se—, —Te—, or —NRa1—, wherein Ra1 is hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group,
- X2 is —O—, —S—, —Se—, —Te—, —S(═O)—, —S(═O)2—, —NRa1—, —BRa2—, —SiRbRc—, —SiRbbRcc—, —GeRdRe—, —GeRddRee—, —(CRfRe)n1—, —(CRffRgg)—, —(C(Rm)═C(Rn))—, —(C(Rmm)═C(Rnn))—, or —(C(Rp)═N))—, wherein Ra1, Ra2, Rb, Rc, Rd, Re, Rf, Rg, Rm, Rn, and Rp are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, and Rbb and Rcc, Rdd and Ree, Rff and Rgg, and Rmm and Rnn are linked with each other to provide a ring structure, and n1 of —(CRfRg)n1— is 1 or 2,
- Ar3 is a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group having at least one functional group selected from C═O, C═S, C═Se, and C═Te, or a substituted or unsubstituted C2 to C30 heterocyclic group having at least one functional group selected from C═O, C═S, C═Se, and C═Te, or a fused ring thereof,
- R1 and R2 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 acyl group, a halogen, a cyano group, a cyano-containing group, a nitro group, a pentafluorosulfanyl group (—SF5), a hydroxyl group, an amine group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, or —SiRaRbRc, wherein Ra, Rb, and Rc are independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group,
- L is —O—, —S—, —Se—, —Te—, —NRa1—, —BRa2—, —SiRbRc—, —SiRbbRcc—, —GeRdRe—, —GeRddRee—, —(CRfRg)n1—, —(CRffRgg)—, —(C(Rm)═C(Rn))—, —(C(Rmm)═C(Rnn))—, —(C(Rp)═N))—, or a single bond, wherein Ra1, Ra2, Rb, Rc, Rd, Re, Rf, Rg, Rm, Rn, and Rp are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, and Rbb and Rcc, Rdd and Ree, Rff and Rgg, and Rmm and Rnn are linked with each other to provide a ring structure, and n1 of —(CRfRg)n1— is 1 or 2,
- Y1 to Y5 are independently N or CRk, wherein Rk is hydrogen, deuterium, a halogen, a cyano group, a nitro group, a hydroxyl group, an amine group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C1 to C10 alkoxy group, or adjacent Rk's are linked to each other to provide a substituted or unsubstituted C6 to C30 arene group, or a substituted or unsubstituted C3 to C30 heteroarene group, or a condensed ring thereof, and
- X3 is —O—, —S—, —Se—, —Te—, —S(═O)—, —S(═O)2—, —NRa1—, —BRa2—, —SiRbRc—, —SiRbbRcc—, —GeRdRe—, —GeRddRee—, —CRfRg—, or —CRffRgg—, wherein Ra1, Ra2, Rb, Rc, Rd, Re, Rf, and Rg are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, and Rbb and Rcc, Rdd and Ree, and Rff and Rgg are linked to each other to provide a ring structure.
5 more elements
A compound represented by Chemical Formula 2E:
- wherein, in Chemical Formula 2E,
- X1 is —Se—, —Te—, or —NRa1—, wherein Ra1 is hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group,
- X2 is —O—, —S—, —Se—, —Te—, —S(═O)—, —S(═O)2—, —NRa1—, —BRa2—, —SiRbRc—, —SiRbbRcc—, —GeRdRe—, —GeRddRee—, —(CRfRg)n1—, —(CRffRgg)—, —(C(Rm)═C(Rn))—, —(C(Rmm)═C(Rnn))—, or —(C(Rp)═N))—, wherein Ra1, Ra2, Rb, Rc, Rd, Re, Rf, Rg, Rm, Rn, and Rp are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, and Rbb and Rcc, Rdd and Ree, Rff and Rgg, and Rmm and Rnn are linked with each other to provide a ring structure, and n1 of —(CRfRg)n1— is 1 or 2,
- Ar3 is a substituted or unsubstituted C6 to C30 hydrocarbon cyclic group having at least one functional group selected from C═O, C═S, C═Se, and C═Te, or a substituted or unsubstituted C2 to C30 heterocyclic group having at least one functional group selected from C═O, C═S, C═Se, and C═Te, or a fused ring thereof,
- R1 and R2 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heteroaryl group, a substituted or unsubstituted C2 to C30 acyl group, a halogen, a cyano group, a cyano-containing group, a nitro group, a pentafluorosulfanyl group (—SF5), a hydroxyl group, an amine group, a hydrazine group, a hydrazone group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, or —SiRaRbRc, wherein Ra, Rb, and Rc are independently hydrogen or a substituted or unsubstituted C1 to C10 alkyl group,
- L is —O—, —S—, —Se—, —Te—, —NRa1—, —BRa2—, —SiRbRc—, —SiRbbRcc—, —GeRdRe—, —GeRddRee—, —(CRfRg)n1—, —(CRffRgg)—, —(C(Rm)═C(Rn))—, —(C(Rmm)═C(Rnn))—, —(C(Rp)═N))—, or a single bond, wherein Ra1, Ra2, Rb, Rc, Rd, Re, Rf, Rg, Rm, Rn, and Rp are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, and Rbb and Rcc, Rdd and Ree, Rff and Rgg, and Rmm and Rnn are linked with each other to provide a ring structure, and n1 of —(CRfRg)n1— is 1 or 2,
- Y1 to Y5 are N or CRk, wherein Rk is hydrogen, deuterium, a halogen, a cyano group, a nitro group, a hydroxyl group, an amine group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C1 to C10 alkoxy group, or adjacent Rk's are linked to each other to provide a substituted or unsubstituted C6 to C30 arene group, or a substituted or unsubstituted C3 to C30 heteroarene group, or a condensed ring thereof, and
- X3 is —O—, —S—, —Se—, —Te—, —S(═O)—, —S(═O)2—, —NRa1—, —BRa2—, —SiRbRc—, —GeRdRe—, —GeRddRee—, —CRfRg—, or —CRffRgg—, wherein Ra1, Ra2, Rb, Rc, Rd, Re, Rf, and Rg are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 to C20 aryloxy group, and Rbb and Rcc, Rdd and Ree, and Rff and Rgg are linked to each other to provide a ring structure.
5 more elements
Dependencies are inferred from the claim text.