US 11,858,911 B2
Squarylium compounds and infrared cut films, infrared cut filters and electronic devices including the same
Moon Gyu Han, Suwon-si (KR); Kyung Bae Park, Hwaseong-si (KR); Dongseon Lee, Suwon-si (KR); Yong Wan Jin, Seoul (KR); and Chul Joon Heo, Busan (KR)
Assigned to Samsung Electronics Co., Ltd., Gyeonggi-do (KR)
Filed by Samsung Electronics Co., Ltd., Suwon-si (KR)
Filed on Feb. 17, 2022, as Appl. No. 17/674,200.
Application 17/674,200 is a continuation of application No. 15/934,069, filed on Mar. 23, 2018, granted, now 11,261,172.
Claims priority of application No. 10-2017-0041844 (KR), filed on Mar. 31, 2017.
Prior Publication US 2022/0169633 A1, Jun. 2, 2022
Int. Cl. C07D 401/14 (2006.01); C09B 57/00 (2006.01); G02B 5/20 (2006.01); G02B 5/22 (2006.01); C09B 23/00 (2006.01); C07C 211/54 (2006.01); C07D 401/04 (2006.01); C07D 403/04 (2006.01); C09B 23/01 (2006.01); H04N 23/57 (2023.01); H10K 85/60 (2023.01); H01L 27/146 (2006.01); H10K 39/32 (2023.01)
CPC C07D 401/14 (2013.01) [C07C 211/54 (2013.01); C07D 401/04 (2013.01); C07D 403/04 (2013.01); C09B 23/0066 (2013.01); C09B 57/007 (2013.01); G02B 5/208 (2013.01); G02B 5/223 (2013.01); H04N 23/57 (2023.01); H10K 85/631 (2023.02); H10K 85/633 (2023.02); H10K 85/636 (2023.02); H10K 85/654 (2023.02); H10K 85/655 (2023.02); H10K 85/657 (2023.02); H10K 85/6572 (2023.02); H01L 27/14621 (2013.01); H10K 39/32 (2023.02)] 19 Claims
 
1. An infrared cut filter comprising an infrared cut film, the infrared cut film comprising:
a squarylium compound represented by Chemical Formula 1:

OG Complex Work Unit Chemistry
wherein, in Chemical Formula 1,
X1 and X2 are each independently one of
a functional group represented by Chemical Formula 1A,
a functional group represented by Chemical Formula 1B,
a functional group represented by Chemical Formula 1C, or
a functional group represented by Chemical Formula 1D,
at least one of X1 and X2 is the functional group represented by Chemical Formula 1A or the functional group represented by Chemical Formula 1B,

OG Complex Work Unit Chemistry
wherein, in Chemical Formula 1A,
Y1 and Y2 are independently N or NR16,
R11 and R12 are linked with each other to collectively comprise a fused ring with a quinazoline ring, or R11 and R12 are each independently one compound of a first set of compounds, the first set of compounds including
hydrogen,
a halogen,
a cyano group,
a nitro group,
a hydroxyl group,
a carboxyl group,
an ester group,
a substituted or unsubstituted C1 to C20 alkyl group,
a substituted or unsubstituted C1 to C20 alkoxy group,
a substituted or unsubstituted C6 to C30 aryl group,
a substituted or unsubstituted C3 to C20 cycloalkyl group,
a substituted or unsubstituted C3 to C20 heteroaryl group, and
a substituted or unsubstituted C2 to C20 heterocycloalkyl group,
R13 is one compound of a second set of compounds, the second set of compounds including
a substituted or unsubstituted C6 to C30 aryl group,
a substituted or unsubstituted C3 to C20 heteroaryl group,
a substituted or unsubstituted C6 to C20 arylamine group, and
a substituted or unsubstituted C3 to C30 heteroarylamine group, and
R14 and R15 are linked with each other to collectively comprise a fused ring with a quinazoline ring, or R14, R15, and R16 are independently one compound of the first set of compounds,

OG Complex Work Unit Chemistry
wherein, in Chemical Formula 1B,
m is 1 or 2,
Z1 and Z2 are independently one of hydrogen or a hydroxyl group,
R21 to R26 are independently one compound of the first set of compounds, and
R27 and R28 are linked with each other to collectively comprise an N-containing aromatic ring group or an N-containing alicyclic cyclic group, or R27 and R28 are independently one compound of a third set of compounds, the third set of compounds including
a substituted or unsubstituted C1 to C20 alkyl group,
a substituted or unsubstituted C1 to C20 alkoxy group,
a substituted or unsubstituted C6 to C30 aryl group,
a substituted or unsubstituted C3 to C20 cycloalkyl group,
a substituted or unsubstituted C3 to C20 heteroaryl group, and
a substituted or unsubstituted C2 to C20 heterocycloalkyl group,

OG Complex Work Unit Chemistry
wherein, in Chemical Formula 1C,
n is 1 or 2,
R31 and R32 are linked with each other to collectively comprise an aromatic ring group or an alicyclic cyclic group,
R33 and R34 are linked with each other to collectively comprise an aromatic ring group or an alicyclic cyclic group, and
R35 to R38 are independently one compound of the first set of compounds,

OG Complex Work Unit Chemistry
wherein, in Chemical Formula 1D,
k is 0 or 1,
Z3 and Z4 are independently one of hydrogen or a hydroxyl group,
R41 and R42 are independently one compound of the first set of compounds, and
R43 and R44 are linked with each other to collectively comprise an N-containing aromatic ring group or an N-containing alicyclic cyclic group, or R43 and R44 are independently one of
a substituted or unsubstituted C1 to C20 alkyl group,
a substituted or unsubstituted C1 to C20 alkoxy group,
a substituted or unsubstituted C6 to C30 aryl group,
a substituted or unsubstituted C3 to C20 cycloalkyl group,
a substituted or unsubstituted C3 to C20 heteroaryl group, or
a substituted or unsubstituted C2 to C20 heterocycloalkyl group,
wherein the substituted or unsubstituted C3 to C20 heteroaryl group in R13 is one of
a substituted or unsubstituted pyridyl group,
a substituted or unsubstituted pyrazinyl group,
a substituted or unsubstituted pyrimidinyl group,
a substituted or unsubstituted pyridazinyl group,
a substituted or unsubstituted quinolyl group,
a substituted or unsubstituted isoquinolyl group,
a substituted or unsubstituted phthalazinyl group,
a substituted or unsubstituted quinazolinyl group,
a substituted or unsubstituted quinoxalinyl group,
a substituted or unsubstituted naphthyridinyl group,
a substituted or unsubstituted cinnolinyl group,
a substituted or unsubstituted pyrrolyl group,
a substituted or unsubstituted pyrazolyl group,
a substituted or unsubstituted imidazolyl group,
a substituted or unsubstituted triazolyl group,
a substituted or unsubstituted tetrazolyl group,
a substituted or unsubstituted thienyl group,
a substituted or unsubstituted thiazolyl group,
a substituted or unsubstituted oxazolyl group,
a substituted or unsubstituted indolyl group,
a substituted or unsubstituted isoindolyl group,
a substituted or unsubstituted indazolyl group,
a substituted or unsubstituted benzoimidazolyl group,
a substituted or unsubstituted benzotriazolyl group,
a substituted or unsubstituted benzothiazolyl group,
a substituted or unsubstituted benzooxazolyl group,
a substituted or unsubstituted carbazole group,
a substituted or unsubstituted phenazinyl group, or
a substituted or unsubstituted acridinyl group.