US 11,730,055 B2
Dopant, charge transfer salt and organic electronic device
Thomas Kugler, Godmanchester (GB); Sheena Zuberi, Godmanchester (GB); Florence Bourcet, Godmanchester (GB); and Jean-Benoit Giguere, Godmanchester (GB)
Assigned to Cambridge Display Technology Limited, Godmanchester (GB); and Sumitomo Chemical Company Limited, Tokyo (JP)
Appl. No. 16/63,671
Filed by Cambridge Display Technology Limited, Godmanchester (GB); and Sumitomo Chemical Company Limited, Tokyo (JP)
PCT Filed Dec. 16, 2016, PCT No. PCT/GB2016/053967
§ 371(c)(1), (2) Date Jun. 18, 2018,
PCT Pub. No. WO2017/103610, PCT Pub. Date Jun. 22, 2017.
Claims priority of application No. 1522439 (GB), filed on Dec. 18, 2015; application No. 1602925 (GB), filed on Feb. 19, 2016; application No. 1602928 (GB), filed on Feb. 19, 2016; and application No. PCT/GB2016/053967 (WO), filed on Jul. 29, 2016.
Prior Publication US 2020/0274072 A1, Aug. 27, 2020
Int. Cl. H10K 85/60 (2023.01); C07D 235/18 (2006.01); C08G 61/02 (2006.01); H10K 85/10 (2023.01); C09K 11/06 (2006.01); C08L 101/02 (2006.01); H01B 1/12 (2006.01); H10K 50/17 (2023.01); H10K 71/00 (2023.01); H10K 71/15 (2023.01); H10K 71/40 (2023.01); H10K 101/30 (2023.01); H10K 102/10 (2023.01)
CPC H10K 85/6572 (2023.02) [C07D 235/18 (2013.01); C08G 61/02 (2013.01); C08L 101/025 (2013.01); C09K 11/06 (2013.01); H01B 1/128 (2013.01); H10K 85/115 (2023.02); H10K 85/611 (2023.02); C08G 2261/143 (2013.01); C08G 2261/148 (2013.01); C08G 2261/1424 (2013.01); C08G 2261/1426 (2013.01); C08G 2261/3142 (2013.01); C08G 2261/514 (2013.01); C08G 2261/95 (2013.01); H10K 50/171 (2023.02); H10K 71/00 (2023.02); H10K 71/15 (2023.02); H10K 71/441 (2023.02); H10K 2101/30 (2023.02); H10K 2102/103 (2023.02)] 15 Claims
OG exemplary drawing
 
1. A compound of formula (I):
(Core)n-(X)m   (I)
wherein Core is Arz, wherein Ar in each occurrence independently is a C6-20 aryl group that may be unsubstituted or substituted with one or more substituents, and z is at least 1; n is 0 and m is 1, or n is 1 and m is at least 1; and X is a group of formula (II):

OG Complex Work Unit Chemistry
wherein:
R1, R4 and R5 are each independently H or a substituent;
each R2 is independently a C1-40 hydrocarbyl;
R3 is H;
one of R1, R4 and R5 is a direct bond or divalent linking group linking the group of formula (II) to Core in the case where n is 1;
x is 0, 1, 2, 3 or 4;
y is 0, 1, 2, 3 or 4; and
the compound of formula (I) is substituted with at least one ionic substituent of formula (III):
-(Sp1)p-(A)q   (III)
wherein:
in the case where p=1, Sp1 is a spacer group selected from C1-12 alkylene wherein one or more non-adjacent C atoms may be replaced with O, S, C═O or COO; and aryl or heteroaryl that may be unsubstituted or substituted with one or more C1-20 alkyl groups wherein one or more non-adjacent C atoms of the C1-20 alkyl groups may be replaced with O, S, C═O or COO;
A is independently an anion selected from the group consisting of sulfonate and —COO−, or a cation selected from the group consisting of —N(R11)3+; —P(R11)3+, S(R11)2+ and a heteroaromatic cation wherein R11 in each occurrence is H or C1-12 hydrocarbyl;
p is 0 or 1;
q is 1 if p is 0; and
q is at least 1 if p is 1, the compound of formula (I) further comprising at least one counterion B to balance the charge of the one or more anions or cations A;
and wherein:
n is 0 and at least one occurrence of at least one of R1, R4 and R5 is an ionic substituent of formula (III); or
n is 1 and Core is substituted with one or more ionic substituents of formula (III); or
n is 1, Core is not substituted with an ionic substituent and at least one of R1, R4 and R5 is an ionic substituent of formula (III).