N-type semiconductor composition, and thin film, organic photoelectric device, image sensor, and electronic device including the same

Patent metadata

Field	Value
Publication number	US-11322688-B2
Application number	US-202016875168-A
Country	US
Kind code	B2
Filing date	May 15, 2020
Priority date	May 15, 2019
Publication date	May 3, 2022
Grant date	May 3, 2022

Abstract

Disclosed are an N-type semiconductor composition including fullerene or a fullerene derivative; and fullerene subunit derivative represented by Chemical Formula 1, and a thin film, an organic photoelectric device, an image sensor and an electronic device including the same.In Chemical Formula 1, X, Cy and R1 to R8 are the same as defined in the detailed description.

First claim

What is claimed is:

1. An organic photoelectric device comprising:
a first electrode and a second electrode facing each other, and
an organic layer between the first electrode and the second electrode,
wherein the organic layer includes an N-type semiconductor composition, the N-type semiconductor composition including,
fullerene or a fullerene derivative; and
a fullerene subunit derivative represented by Chemical Formula 1:

wherein, in Chemical Formula 1,
Cy is a cyclic hydrocarbon group selected from a C3 to C20 alicyclic hydrocarbon group and a C6 to C20 aromatic hydrocarbon group, or a fused cyclic group of two or more cyclic hydrocarbon groups,
X is at least one bulky substituent selected from a substituted or unsubstituted C3 to C30 branched alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group, and
R 1 to R 8 are independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C1 to C20 linear or branched alkoxy group, a substituted or unsubstituted C3 to C20 linear or branched alkylsilyl group, a substituted or unsubstituted C2 to C20 linear or branched heteroalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, or a combination thereof,
provided at least one of R 1 to R 8 is a bulky substituent selected from a substituted or unsubstituted C3 to C20 branched alkyl group, a substituted or unsubstituted C3 to C20 branched alkoxy group, a substituted or unsubstituted C3 to C20 branched alkylsilyl group, a substituted or unsubstituted C3 to C20 branched heteroalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, and a combination thereof.

2. The organic photoelectric device of claim 1 , wherein
in Chemical Formula 1, at least one of R 1 to R 3 and at least one of R 6 to R 8 are the same or different, and
at least one of R 1 to R 3 and at least one of R 6 to R 8 are a bulky substituent selected from a substituted or unsubstituted C3 to C20 branched alkyl group, a substituted or unsubstituted C3 to C20 branched alkoxy group, a substituted or unsubstituted C3 to C20 branched alkylsilyl group, a substituted or unsubstituted C3 to C20 branched heteroalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, and a combination thereof.

3. The organic photoelectric device of claim 2 , wherein in Chemical Formula 1, at least one bulky substituent of R 1 to R 3 and at least one bulky substituent of R 6 to R 8 are present symmetrically with respect to an axis through Cy.

4. The organic photoelectric device of claim 1 , wherein in Chemical Formula 1,
at least one of R 1 and R 2 and at least one of R 7 and R 8 are the same or different, and
are a bulky substituent selected from a substituted or unsubstituted C3 to C20 branched alkyl group, a substituted or unsubstituted C3 to C20 branched alkoxy group, a substituted or unsubstituted C3 to C20 branched alkylsilyl group, a substituted or unsubstituted C3 to C20 branched heteroalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, and a combination thereof.

5. The organic photoelectric device of claim 1 , wherein In Chemical Formula 1,
R 2 and R 7 are a bulky substituent selected from a substituted or unsubstituted C3 to C20 branched alkyl group, a substituted or unsubstituted C3 to C20 branched alkoxy group, a substituted or unsubstituted C3 to C20 branched alkylsilyl group, a substituted or unsubstituted C3 to C20 branched heteroalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, and a combination thereof, and
R 1 , R 3 , R 4 , R 5 , R 6 , and R 8 are hydrogen, deuterium, a halogen, a cyano group, a C1 to C20 linear alkyl group, or a combination thereof.

6. The organic photoelectric device of claim 1 , wherein in Chemical Formula 1, two adjacent substituents of R 1 to R 3 and two adjacent substituents of R 6 to R 8 are linked to each other to provide a C3 to C20 alicyclic hydrocarbon group.

7. The organic photoelectric device of claim 6 , wherein in Chemical Formula 1,
R 2 and R 3 are linked to each other to provide a C3 to C20 alicyclic hydrocarbon group, and
R 6 and R 7 are linked to each other to provide a C3 to C20 alicyclic hydrocarbon group.

8. The organic photoelectric device of claim 7 , wherein the fullerene subunit derivative represented by Chemical Formula 1 is a compound represented by Chemical Formula 1A:

wherein, in Chemical Formula 1A,
Cy is a cyclic hydrocarbon group selected from a C3 to C20 alicyclic hydrocarbon group and a C6 to C20 aromatic hydrocarbon group, or a fused cyclic group of two or more cyclic hydrocarbon groups,
X is at least one bulky substituent selected from a substituted or unsubstituted C3 to C30 branched alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, and a substituted or unsubstituted C2 to C30 heteroaryl group,
R 1 , R 2a , R 4 , R 5 , R 6a , and R 8 are independently hydrogen, deuterium, a halogen, a cyano group, a substituted or unsubstituted C1 to C20 linear or branched alkyl group, a substituted or unsubstituted C1 to C20 linear or branched alkoxy group, a substituted or unsubstituted C3 to C20 linear or branched alkylsilyl group, a substituted or unsubstituted C2 to C20 linear or branched heteroalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, or a combination thereof, and
a1 and a2 are independently integers of 1 to 4.

9. The organic photoelectric device of claim 1 , wherein the cyclic hydrocarbon group in Cy is a heterocyclic group including at least one functional group selected from —N═, —NR—, —O—, —S—, —Se—, —Te—, —C(═O)—, —C(═S)—, —C(═Se)—, —C(═Te)—, —C(═C(CN) 2 )—, and —C(═NR)— wherein R is a C1 to C10 alkyl group.

10. The organic photoelectric device of claim 1 , wherein in Chemical Formula 1, Cy is pyrrole, furan, pyrroline, pyrrolidinedione, cyclopentanediene, cyclopentanedione, pyrrolo imidazole, pyrrolo imidazole including ketone (C═O) group in the ring, pyridine, pyrimidine, indo

Assignees

• Samsung Electronics Co Ltd

Inventors

• Shibuya Hiromasa
• Baik Chul
• Matsuo Yutaka
• Yun Sung Young
• Lim Seon-Jeong
• Shin Ji Soo
• Lee Gae Hwang
• Choi Yeong Suk
• Choi Taejin
• Hong Hye Rim

Classifications

• H10K85/215 Primary

  comprising substituents, e.g. PCBM · CPC title

• H10K85/621 Primary

  Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide · CPC title

• H10F39/80 Primary

  Constructional details of image sensors · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• C07D209/56

  Ring systems containing three or more rings · CPC title