US 12,035,623 B2
Organic molecules for optoelectronic devices
Stefan Seifermann, Bühl (DE)
Assigned to Samsung Display Co., Ltd., Yongin-si (KR)
Appl. No. 17/265,776
Filed by SAMSUNG DISPLAY CO., LTD., Yongin-si (KR)
PCT Filed Aug. 7, 2019, PCT No. PCT/EP2019/071208
§ 371(c)(1), (2) Date Feb. 3, 2021,
PCT Pub. No. WO2020/035365, PCT Pub. Date Feb. 20, 2020.
Claims priority of application No. 102018119598.2 (DE), filed on Aug. 13, 2018.
Prior Publication US 2021/0399230 A1, Dec. 23, 2021
Int. Cl. H10K 85/00 (2023.01); C07D 403/14 (2006.01); C07D 487/04 (2006.01); C07D 491/048 (2006.01); C07D 495/04 (2006.01); C09K 11/06 (2006.01); H10K 85/60 (2023.01); H10K 50/11 (2023.01); H10K 101/10 (2023.01)
CPC H10K 85/6572 (2023.02) [C07D 403/14 (2013.01); C07D 487/04 (2013.01); C07D 491/048 (2013.01); C07D 495/04 (2013.01); C09K 11/06 (2013.01); H10K 85/654 (2023.02); H10K 85/657 (2023.02); C09K 2211/1018 (2013.01); H10K 50/11 (2023.02); H10K 2101/10 (2023.02)] 20 Claims
OG exemplary drawing
 
1. An organic molecule, comprising:
a first chemical moiety comprising a structure of Formula I,

OG Complex Work Unit Chemistry
and
two second chemical moieties, each independently comprising a structure of Formula II,

OG Complex Work Unit Chemistry
wherein the first chemical moiety is linked to each of the two second chemical moieties via a single bond;
wherein
RT, RV, RW, RX, and RY is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is selected from the group consisting of R2 and 1,3,5-triazinyl, which is substituted with two substituents RTz;

OG Complex Work Unit Chemistry
wherein the dashed line indicates the binding site of 1,3,5-triazinyl;
T, V, W, X, and Y is the binding site of a single bond linking the first chemical moiety to one of the two second chemical moieties or is selected from the group consisting of R2 and 1,3,5-triazinyl, which is substituted with two substituents RTz;
# represents the binding site of a single bond linking the second chemical moieties to the first chemical moiety;
Z is at each occurrence independently selected from the group consisting of a direct bond, CR3R4, C═CR3R4, C═O, C═NR3, NR3, O, SiR3R4, S, S(O) and S(O)2;
R1, R2, RI is independently from each other at each occurrence independently selected from the group consisting of:
hydrogen, deuterium,
C1-C5-alkyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C2-C8-alkenyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C2-C8-alkynyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium; and
C6-C18-aryl,
which is optionally substituted with one or more substituents R6;
RTz is at each occurrence independently selected from the group consisting of:
hydrogen, deuterium,
C1-C5-alkyl,
wherein one or more hydrogen atoms are optionally substituted by deuterium;
C6-C18-aryl,
which is optionally substituted with one or more substituents R5, and
C3-C17-heteroaryl,
which is optionally substituted with one or more substituents R5;
Ra, R3 and R4 is at each occurrence independently selected from the group consisting of:
hydrogen, deuterium, N(R5)2, OR5, Si(R5)3, B(OR5)2, OSO2R5, CF3, CN, F, Br, I,
C1-C40-alkyl,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C═CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C═S, C═Se, C═NR5, P(═O)(R5), SO, SO2, NR5, O, S or CONR5;
C1-C40-alkoxy,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C═CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C═S, C═Se, C═NR5, P(═O)(R5), SO, SO2, NR5, O, S or CONR5;
C1-C40-thioalkoxy,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C═CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C═S, C═Se, C═NR5, P(═O)(R5), SO, SO2, NR5, O, S or CONR5;
C2-C40-alkenyl,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C═CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C═S, C═Se, C═NR5, P(═O)(R5), SO, SO2, NR5, O, S or CONR5;
C2-C40-alkynyl,
which is optionally substituted with one or more substituents R5 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R5C═CR5, C≡C, Si(R5)2, Ge(R5)2, Sn(R5)2, C═O, C═S, C═Se, C═NR5, P(═O)(R5), SO, SO2, NR5, O, S or CONR5;
C6-C60-aryl,
which is optionally substituted with one or more substituents R5;
C3-C57-heteroaryl,
which is optionally substituted with one or more substituents R5; and
a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system formed by ring-closure with one or more of the other substituents selected from the group consisting of Ra, R3, R4 and R5;
R5 is at each occurrence independently selected from the group consisting of hydrogen, deuterium, N(R6)2, OR6, Si(R6)3, B(OR6)2, OSO2R6, CF3, CN, F, Br, I,
C1-C40-alkyl,
which is optionally substituted with one or more substituents R6 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R6C═CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C═S, C═Se, C═NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
C1-C40-alkoxy,
which is optionally substituted with one or more substituents R6 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R6C═CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C═S, C═Se, C═NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
C1-C40-thioalkoxy,
which is optionally substituted with one or more substituents R6 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R6C═CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C═S, C═Se, C═NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
C2-C40-alkenyl,
which is optionally substituted with one or more substituents R6 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R6C═CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C═S, C═Se, C═NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
C2-C40-alkynyl,
which is optionally substituted with one or more substituents R6 and
wherein one or more non-adjacent CH2-groups are optionally substituted by R6C═CR6, C≡C, Si(R6)2, Ge(R6)2, Sn(R6)2, C═O, C═S, C═Se, C═NR6, P(═O)(R6), SO, SO2, NR6, O, S or CONR6;
C6-C60-aryl,
which is optionally substituted with one or more substituents R6;
C3-C57-heteroaryl,
which is optionally substituted with one or more substituents R6; and
a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system formed by ring-closure with one or more of the other substituents selected from the group consisting of Ra, R3, R4 and R5;
R6 is at each occurrence independently selected from the group consisting of: hydrogen, deuterium, OPh, CF3, CN, F,
C1-C5-alkyl,
wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;
C1-C5-alkoxy,
wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;
C1-C5-thioalkoxy,
wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;
C2-C5-alkenyl,
wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;
C2-C5-alkynyl,
wherein one or more hydrogen atoms are optionally, independently from each other substituted by deuterium, CN, CF3, or F;
C6-C18-aryl,
which is optionally substituted with one or more C1-C5-alkyl substituents;
C3-C17-heteroaryl,
which is optionally substituted with one or more C1-C5-alkyl substituents;
N(C6-C18-aryl)2;
N(C3-C17-heteroaryl)2,
and N(C3-C17-heteroaryl)(C6-C18-aryl);
wherein the substituents Ra, R3, R4 or R5 independently from each other optionally form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system together with one or more of the other substituents Ra, R3, R4 or R5;
wherein
exactly one substituent selected from the group consisting of RT, RV, RW, RX, and RY is 1,3,5-triazinyl, which is substituted with two substituents RTz;
exactly one substituent selected from the group consisting of T, V, W, X, and Y is 1,3,5-triazinyl, which is substituted with two substituents RTz;
exactly one substituent selected from the group consisting of RT, RV, RW, RX, and RY represents the binding site of a single bond linking the first chemical moiety and one of the two second chemical moieties, and
exactly one substituent selected from the group consisting of T, V, W, X and Y represents the binding site of a single bond linking the first chemical moiety and one of the two second chemical moieties.