Semiconductor mixed material and application thereof

Patent metadata

Field	Value
Publication number	US-11950491-B2
Application number	US-202016950600-A
Country	US
Kind code	B2
Filing date	Nov 17, 2020
Priority date	Apr 28, 2020
Publication date	Apr 2, 2024
Grant date	Apr 2, 2024

Abstract

A semiconductor mixed material comprises an electron donor, a first electron acceptor and a second electron acceptor. The first electron donor is a conjugated polymer. The energy gap of the first electron acceptor is less than 1.4 eV. At least one of the molecular stackability, π-π*stackability, and crystallinity of the second electron acceptor is smaller than the first electron acceptor. The electron donor system is configured to be a matrix to blend the first electron acceptor and the second electron acceptor. The present invention also provides an organic electronic device including the semiconductor mixed material.

First claim

What is claimed is:

1. A semiconductor mixed material, comprising:
an electron donor which is a random copolymer with at least two structural units randomly arranged comprising the structure of Formula V:

wherein, the structural units comprise A and B, the electron donor comprises continuous a plurality of monomers with Formula V, and the number of A and B of each monomer with Formula V is random, and an arrangement with A and B of each monomer is random, without an arrangement with only a single A and a single B of each monomer;
X is selected from one of following: C, S, N, and O;
X 1 to X 4 can be the same or different, and X 1 to X 4 are independently selected from the group consisting of C, C—F, C—Cl, C—Br, and C—I;
Ar 5 to Ar 8 an be the same or different, and Ar 5 to Ar 8 are independently selected from the group consisting of C1-C30 fused ring with and without substituents, C1-C30 fused heteroaromatic ring with and without substituents, C1-C30 fused heterocyclic ring with and without substituents, benzene ring with and without substituents, five-membered ring with and without substituents, and six-membered ring with and without substituents, wherein Formula V comprises at least one of Ar 5 ≠Ar 5 ≠ and Ar 7 ≠Ar 8 ;
π 5 and π 6 can be the same or different, and π 5 and π 6 are independently selected from the group consisting of C8-C30 fused ring with and without substituents, C8-C30 fused heteroaromatic ring with and without substituents, C8-C30 fused heterocyclic ring with and without substituents, wherein Ar 5 to Ar 8 are different from π 5 and π 6 ;
a to f can be the same or different, and a to f are integers independently selected from 1 to 5; and
the sum of x and y is 1, x≠0 and y≠0;

a first electron acceptor with an energy gap less than 1.4 eV, the first electron acceptor comprising a structure of Formula 1:

wherein R 1 and R 2 can be the same or different, and R 1 and R 2 are independently selected from the group consisting of C1-C30 alkyl chain with and without substitutents, and halogen;
Ar 1 , Ar 2 , EG 1 and EG 2 can be the same or different, and Ar 1 , Ar 2 , EG 1 and EG 2 are independently selected from the group consisting of C1-C30 fused ring with and without substituents, C1-C30 fused heteroaromatic ring with and without substituents, and C1-C30 fused heterocyclic ring with and without substituents, benzene ring with and without substituents, five-membered heterocyclic ring with and without substituents, and six-membered heterocyclic ring with and without substituents; and
π 1 and π 2 can be the same as or different from each other, and π 1 and π 2 are independently selected from the group consisting of C1-C30 fused rings with and without substituents, C1-C30 fused heterocyclic ring with and without substituents, C1-C30 fused ring with and without substituents, benzene ring with and without substituents, five-membered ring with and without substituents, and six-membered ring with and without substituents, alkene with and without substituents and alkyne with and without substituents, wherein m is an integer selected from 0 to 5; and

a second electron acceptor, wherein at least one of molecular stack ability, π-π* stack ability, and crystallinity of the second electron acceptor is less than that of the first electron acceptor;
wherein, the electron donor is configured as a substrate for mixing the first electron acceptor and the second electron acceptor.

2. The semiconductor mixed material of claim 1 , wherein R 1 and R 2 can be the same or different, and R 1 and R 2 are respectively selected from the group consisting of C1-C30 alkyl chain with carbon branched chain structure with substituents and without substituents.

3. The semiconductor mixed material of claim 1 , wherein the substituent of Formula I is selected from the group consisting of C1-C30 alkyl, C1-C30 branched alkyl, C1-C30 silyl, C1-C30 ester, C1-C30 alkoxy, C1-C30 alkylthio, C1-C30 haloalkyl, C1-C30 alkenyl, C1-C30 alkynyl, C1-C30 cyano-containing carbon chain, C1-C30 nitro-containing carbon chain, C1-C30 hydroxy-containing carbon chain, C1-C30 keto-containing carbon chain, oxygen, and halogen.

4. The semiconductor mixed material of claim 1 , wherein the second acceptor comprises at least one structure of Formula II, Formula III, and Formula IV:

wherein, Z is selected from one of following: C, Si, and Ge;
R 3 to R 17 can be the same or different, and R 3 , AR 17 are independently selected from the group consisting of C1-C30 alkyl chain with and without substituents and halogen;
Ar 3 , Ar 4 , EG 3 , EG 4 can be the same or different, and Ar 3 , Ar 4 , EG 3 , EG 4 are independently selected from the group consisting of C1-C30 fused ring with and without substituents, C1-C30 fused heteroaromatic ring with and without substituents, and C1-C30 fused heterocyclic ring with and without substituents, benzene ring with and without substituents, five-membered heterocyclic ring with and without substituents, and six-membered heterocyclic ring with and without substituents; and
π 3 and π 4 can be the same or different, and π 3 and π 4 are independently selected from the group consisting of C1-C30 fused ring with and without substituents, C1-C30 fused heteroaromatic ring with and without substituents, C1-C30 fused heterocyclic ring with and without substituents, benzene ring with and without substituents, five-membered ring with and without substituents, and six-membered ring with and without substituents, alkene and alkyne with and without substituents, wherein m is an integer selected from 0 to 5.

5. The semiconductor mixed material of claim 1 , wherein one of Ar 5 to Ar 8 further comprises at least one of Si and S.

6. The semiconductor mixed material of claim 1 , wherein the weight percentage of the first electron acceptor is not less than that of the second electron acceptor in the semiconductor mixed material.

7. A semiconductor mixed material, comprising:
an electron donor which is a random copolymer with at least two structural units randomly arranged comprising the structure of Formula V:

wherein, the structural units comprise A and B, the electron donor comprises continuous a plurality of monomers with Formula V, and the number of A and B of each monomer with Formula V is random, and an arrangement with A and B of each monomer is random, without an arrangement with only a single A and a single B of each monomer;
X is selected from one of following: C, S, N, and O;
X 1 to X 4 can be the same or different, and X 1 to X 4 are independently selected from the group consisting of C, C—F, C—Br, and C—I;
Ar 5 to Ar 8 can be the same or different, and Ar 5 to Ar 8 are independently selected from the group consisting of C1-C30 fused ring with and without substituents, C1-C30 fused heteroaromatic ring with and without substituents, C1-C30 fused heterocyclic ring with and without substituents, benzene ring with and without substituents, five-membered ring with and without substituents, and six-membered ring with and without substituents, wherein Formula V comprises at least one of Ar 5 ≠Ar 7 and Ar 6 ≠Ar 8

Assignees

• Raynergy Tek Inc

Inventors

• Chang Yi-Ming
• Liao Chuang-Yi
• Li Wei-Long
• Hsiao Yu-Tang
• Lee Chun-Chieh
• Li Chia-Hua
• Tan Huei-Shuan

Classifications

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K85/113 Primary

  Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene · CPC title

• C07D495/22 Primary

  in which the condensed system contains four or more hetero rings · CPC title

• C08G61/126

  with a five-membered ring containing one sulfur atom in the ring · CPC title

• C08K3/045

  Fullerenes · CPC title