US 11,835,856 B2
Photosensitive compositions, preparation methods thereof, quantum dot polymer composite prepared therefrom
Shin Ae Jun, Seongnam-si (KR); Shang Hyeun Park, Yongin-si (KR); Hojeong Paek, Suwon-si (KR); Jonggi Kim, Suwon-si (KR); Hyeyeon Yang, Yongin-si (KR); Eun Joo Jang, Suwon-si (KR); and Yong Seok Han, Anyang-si (KR)
Assigned to SAMSUNG ELECTRONICS CO., LTD., Gyeonggi-Do (KR); and SAMSUNG SDI CO., LTD., Gyeonggi-Do (KR)
Filed by SAMSUNG ELECTRONICS CO., LTD., Suwon-si (KR); and Samsung SDI Co., Ltd., Yongin-si (KR)
Filed on Mar. 17, 2021, as Appl. No. 17/204,110.
Application 17/204,110 is a division of application No. 15/241,208, filed on Aug. 19, 2016, granted, now 10,983,432.
Claims priority of application No. 10-2015-0119128 (KR), filed on Aug. 24, 2015.
Prior Publication US 2021/0200082 A1, Jul. 1, 2021
Int. Cl. G03F 7/00 (2006.01); G03F 7/033 (2006.01); G02B 5/20 (2006.01); G02B 5/22 (2006.01); C09K 11/02 (2006.01); C09K 11/08 (2006.01)
CPC G03F 7/0007 (2013.01) [C09K 11/02 (2013.01); C09K 11/08 (2013.01); G02B 5/207 (2013.01); G02B 5/223 (2013.01); G03F 7/033 (2013.01)] 19 Claims
 
1. A quantum dot-polymer composite pattern comprising:
a first quantum dot polymer composite, wherein the first quantum dot polymer composite is configured to emit a first light,
wherein the first quantum dot polymer composite comprises a matrix comprising an acid group-containing polymer and a polymerization product of a photopolymerizable monomer comprising a carbon-carbon double bond;
a plurality of quantum dots dispersed in the matrix;
wherein the acid group-containing polymer has an acid value of greater than or equal to about 80 milligrams of KOH per gram of acid group-containing polymer as measured by a titration with a solution of potassium hydroxide,
wherein the quantum dots comprise an organic ligand, and wherein the organic ligand comprises RCOOH, RNH2, R2NH, R3N, RSH, R3P, ROH, RCOOR′, RPO(OH)2, R2POOH (wherein R and R′ are independently a C5 to C24 aliphatic hydrocarbon group, a C5 to C20 alicyclic hydrocarbon group, or a C6 to C20 aromatic hydrocarbon group), or a combination thereof,
wherein the acid group-containing polymer is a copolymer consisting of a first repeating unit, a second repeating unit, and a third repeating unit,
wherein the first repeating unit is a repeating unit represented by Chemical Formula 1-1, a repeating unit represented by Chemical Formula 1-2, or a combination thereof:

OG Complex Work Unit Chemistry
wherein
R1 is hydrogen, a C1 to C3 alkyl group, or —(CH2)n1—COOH (wherein n1 is 0 to 2),
R2 is hydrogen, a C1 to C3 alkyl group, or —COOH,
L is a single bond, a C1 to C15 aliphatic hydrocarbon group, a C6 to C30 aromatic hydrocarbon group, a C6 to C30 alicyclic hydrocarbon group, or a C1 to C15 aliphatic hydrocarbon group substituted with a C6 to C30 aromatic hydrocarbon group or a C6 to C30 alicyclic hydrocarbon group, and
* indicates a portion connected to an adjacent atom;

OG Complex Work Unit Chemistry
wherein
R1 is hydrogen, a C1 to C3 alkyl group, or —(CH2)n1—COOH (wherein n1 is 0 to 2),
R2 is hydrogen or a C1 to C3 alkyl group,
L is a C1 to C15 alkylene group, a C1 to C15 alkylene group wherein at least one methylene group is substituted with —C(═O)—, —O—, or —C(═O)O—, a C6 to C30 aromatic hydrocarbon group, a C6 to C30 alicyclic hydrocarbon group, or a C1 to C15 aliphatic hydrocarbon group substituted with a C6 to C30 aromatic hydrocarbon group or a C6 to C30 alicyclic hydrocarbon group,
n is an integer of 1 to 3, and
* indicates a portion connected to an adjacent atom;
wherein the second repeating unit is a repeating unit represented by Chemical Formula 2, a repeating unit represented by Chemical Formula 4, a repeating unit represented by Chemical Formula 5, a repeating unit represented by Chemical Formula A, or a combination thereof:

OG Complex Work Unit Chemistry
wherein
R1 is hydrogen or a C1 to C3 alkyl group,
R2 is a C1 to C15 aliphatic hydrocarbon group, a C6 to C30 aromatic hydrocarbon group, a C6 to C30 alicyclic hydrocarbon group, or a C1 to C15 aliphatic hydrocarbon group substituted with a C6 to C30 aromatic hydrocarbon group or a C6 to C30 alicyclic hydrocarbon group,
R3 is hydrogen or a C1 to C3 alkyl group, and
* indicates a portion connected to an adjacent atom;

OG Complex Work Unit Chemistry
wherein
R1 is hydrogen or a C1 to C3 alkyl group,
L is a C1 to C15 alkylene group, a C1 to C15 alkylene group wherein at least one methylene group is substituted with —C(═O)—, —O—, or —C(═O)O—, a C6 to C30 aromatic hydrocarbon group, a C6 to C30 alicyclic hydrocarbon group, or a C1 to C15 aliphatic hydrocarbon group substituted with a C6 to C30 aromatic hydrocarbon group or a C6 to C30 alicyclic hydrocarbon group,
R2 is a C1 to C15 aliphatic hydrocarbon group, a C6 to C30 aromatic hydrocarbon group, a C6 to C30 alicyclic hydrocarbon group, or a C1 to C15 aliphatic hydrocarbon group substituted with a C6 to C30 aromatic hydrocarbon group or a C6 to C30 alicyclic hydrocarbon group,
R3 is hydrogen or a C1 to C3 alkyl group,
n is an integer of 1 to 3, and
* indicates a portion connected to an adjacent atom;

OG Complex Work Unit Chemistry
wherein
each of R1 and R2 is independently hydrogen or a C1 to C3 alkyl group,
Ar is a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group or a substituted or unsubstituted C6 to C30 alicyclic hydrocarbon group, and
* indicates a portion connected to an adjacent atom;

OG Complex Work Unit Chemistry
wherein
R1 is hydrogen or a C1 to C3 alkyl group,
R2 is a C1 to C15 aliphatic hydrocarbon group, a C6 to C30 aromatic hydrocarbon group, a C6 to C30 alicyclic hydrocarbon group, or a C1 to C15 aliphatic hydrocarbon group substituted with a C6 to C30 aromatic hydrocarbon group or a C6 to C30 alicyclic hydrocarbon group,
R3 is hydrogen or a C1 to C3 alkyl group, and
* indicates a portion connected to an adjacent atom,
wherein the third repeating unit is a repeating unit represented by Chemical Formula 3:

OG Complex Work Unit Chemistry
wherein
each of R1 and R2 is independently hydrogen or a C1 to C3 alkyl group,
L is a C1 to C15 alkylene group, a C1 to C15 alkylene group wherein at least one methylene group is substituted with —C(═O)—, —O—, or —C(═O)O—, a C6 to C30 aromatic hydrocarbon group, a C6 to C30 alicyclic hydrocarbon group, or a C1 to C15 aliphatic hydrocarbon group substituted with a C6 to C30 aromatic hydrocarbon group or a C6 to C30 alicyclic hydrocarbon group,
Z is a hydroxyl group (—OH), a mercapto group (—SH), or an amino group (—NHR, wherein R is hydrogen or a C1 to C5 alkyl group), and
* indicates a portion connected to an adjacent atom,
wherein in the composite, the plurality of quantum dots are configured to emit the first light with a quantum yield of greater than or equal to about 60% when being irradiated with an excitation light, and
wherein an amount of the plurality of quantum dots comprising the organic ligand is greater than about 5 weight percent based on a total amount of the composite.