IP Library Granted Patent US 9,921,472
Granted Patent B2
US 9,921,472 · App. 15/295,332 · Granted Mar 20, 2018

Photosensitive compositions and quantum dot polymer composite patterns including the same

Inventors: Hyeyeon Yang (Yongin-si, KR); Tae Hyung Kim (Seoul, KR); Shang Hyeun Park (Yongin-si, KR); Shin Ae Jun (Seongnam-si, KR); Yong Seok Han (Anyang-si, KR); Eun Joo Jang (Suwon-si, KR); Deukseok Chung (Yongin-si, KR)
Assignees: SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG DISPLAY CO., LTD.; SAMSUNG SDI CO., LTD.
G03F7/0007G03F7/0045G03F7/028G03F7/031G03F7/033G03F7/162G03F7/168G03F7/2002G03F7/322G03F7/40
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Quick Facts
Patent No.
US 9,921,472
App. No.
15/295,332
Granted
Mar 20, 2018
Kind
B2
Abstract

A photosensitive composition and a quantum dot-polymer composite pattern formed from the photosensitive composition are disclosed, and the photosensitive composition includes: a plurality of quantum dots; a color filter material including an absorption dye, an absorption pigment, or a combination thereof; a polymer binder; a photopolymerizable monomer having a carbon-carbon double bond; a photoinitiator; and a solvent, wherein in a normalized photoluminescence spectrum of the quantum dot and a normalized ultraviolet-visible absorption spectrum of the color filter material, a photoluminescence peak wavelength (PL peak wavelength) of the quantum dot and a wavelength of maximum absorbance of the color filter material do not overlap with each other, and the color filter material is included in an amount of less than or equal to 1 part by weight per 10 parts by weight of the plurality of quantum dots.

Claims (41)

1. A photosensitive composition comprising

a plurality of quantum dots;

a color filter material comprising an absorption dye, an absorption pigment, or a combination thereof;

a polymer binder;

a photopolymerizable monomer comprising a carbon-carbon double bond;

a photoinitiator; and

a solvent,

wherein in a normalized photoluminescence spectrum of the quantum dot and a normalized ultraviolet-visible absorption spectrum of the color filter material, a range of a photoluminescence peak wavelength of the quantum dot and a range of a wavelength of maximum absorbance of the color filter material do not overlap with each other,

wherein the color filter material is included in an amount of less than or equal to 1 part by weight per 10 parts by weight of the plurality of quantum dots, and

wherein the quantum dot comprises a core comprising a first semiconductor nanocrystal and a shell disposed over the core and comprising a second semiconductor nanocrystal that is different from the first semiconductor nanocrystal.

2. The photosensitive composition of claim 1 , wherein in the normalized photoluminescence spectrum of the quantum dot and the normalized ultraviolet-visible absorption spectrum of the color filter material, an absorption initiation wavelength of the color filter material is present within or before a longer wavelength tail region of the quantum dot.

3. The photosensitive composition of claim 1 , wherein in the normalized photoluminescence spectrum of the quantum dot and the normalized ultraviolet-visible absorption spectrum of the color filter material, an absorption termination wavelength of the ultraviolet absorption spectrum of the color filter material is present within or after a shorter wavelength tail region of the quantum dot.

4. The photosensitive composition of claim 1 , wherein the range of the photoluminescence peak wavelength of the quantum dot is from about 500 nanometers to about 550 nanometers, and the color filter material has an absorption initiation wavelength of greater than or equal to about 500 nanometers.

5. The photosensitive composition of claim 1 , wherein the range of the photoluminescence peak wavelength of the quantum dot is from about 600 nanometers to about 700 nanometers and the color filter material has an absorption initiation wavelength of greater than or equal to about 600 nanometers.

6. The photosensitive composition of claim 1 , wherein the range of the photoluminescence peak wavelength of the quantum dot is from about 600 nanometers to about 700 nanometers, and the color filter material has an absorption initiation wavelength between about 480 nanometers and about 600 nanometers.

7. The photosensitive composition of claim 1 , wherein the quantum dot comprises an organic ligand having a hydrophobic moiety on a surface thereof, and the organic ligand comprises RCOOH, RNH 2 , R 2 NH, R 3 N, RSH, R 3 PO, R 3 P, ROH, RCOOR′, RPO(OH) 2 , R 2 POOH (wherein, R and R′ are independently a C5 to C24 aliphatic hydrocarbon group or a C5 to C20 aromatic hydrocarbon group), or a combination thereof.

8. The photosensitive composition of claim 7 , wherein the organic ligand consists of RCOOH, RNH 2 , R 2 NH, R 3 N, RSH, R 3 PO, R 3 P, ROH, RCOOR′, RPO(OH) 2 , R 2 POOH (wherein, R and R′ are independently a C5 to C24 aliphatic hydrocarbon group or a C5 to C20 aromatic hydrocarbon group), or a combination thereof.

9. The photosensitive composition of claim 1 , wherein the quantum dot comprises a Group II-VI compound, a Group III-V compound, a Group IV-VI compound, a Group IV compound, a Group I-III-VI compound, a Group I-II-IV-IV compound, or a combination thereof.

10. The photosensitive composition of claim 1 , wherein the absorption dye or pigment comprises an organometallic complex, a coumarin compound, a rhodamine compound, a phenoxazone compound, a stilbene compound, a terphenyl compound, a quaterphenyl compound, a perylene compound, a diketopyrrolopyrrole compound, a phthalocyanine compound, an anthraquinone compound, a squaraine compound, or a combination thereof.

11. The photosensitive composition of claim 1 , wherein the polymer binder comprises a carboxyl group, and has an acid value of greater than or equal to about 50 milligrams of potassium hydroxide per gram of the polymer binder.

12. The photosensitive composition of claim 1 , wherein the photosensitive composition comprises

about 5 wt % to about 40 wt % of the plurality of quantum dots;

about 0.5 wt % to about 30 wt % of the polymer binder;

about 0.5 wt % to about 20 wt % of the photopolymerizable monomer;

about 0.01 wt % to about 10 wt % of the photoinitiator; and

a balance amount of the solvent, each based on the total weight of the composition.

13. A quantum dot polymer composite pattern prepared from the photosensitive composition of claim 1 .

14. The quantum dot polymer composite pattern of claim 13 , wherein a photoluminescence spectrum of the quantum dot-polymer composite pattern has a tail region area of about 580 nanometers to about 650 nanometers that is decreased by at least about 10% when being compared with an inherent tail region area of the quantum dot at about 580 nanometers to about 650 nanometers.

15. The quantum dot polymer composite pattern of claim 13 , wherein a National Television System Committee color gamut ratio of the quantum dot-polymer composite pattern is larger than that of the quantum dot.

16. An electronic device comprising the quantum dot-polymer composite pattern of claim 13 .

17. The photosensitive composition of claim 1 , wherein the color filter material is included in an amount of less than 1 part by weight per 100 parts by weight of the plurality of quantum dots.

18. The photosensitive composition of claim 1 , wherein the color filter material is included in an amount of less than or equal to about 0.5 part by weight per 100 parts by weight of the plurality of quantum dots.

19. The photosensitive composition of claim 1 , wherein the absorption dye or pigment comprises an organometallic complex, a coumarin compound, a rhodamine compound, a phenoxazone compound, a stilbene compound, a terphenyl compound, a quaterphenyl compound, a perylene compound, a diketopyrrolopyrrole compound, a phthalocyanine compound, an anthraquinone compound, a squaraine compound, or a combination thereof and the color filter material is included in an amount of less than 1 part by weight per 100 parts by weight of the plurality of quantum dots.

20. A method for the manufacture of a quantum dot polymer composite pattern, the method comprising

preparing a binder solution comprising a polymer binder and a solvent;

dispersing a plurality of quantum dots and a color filter material in the binder solution to obtain a binder dispersion comprising a dispersion of the quantum dots, the color filter material, and a binder;

mixing the binder dispersion with at least one of a photopolymerizable monomer, a photoinitiator, the solvent, or a combination thereof, to form a photosensitive composition; and

preparing the quantum dot polymer composite pattern from the photosensitive compound;

wherein in a normalized photoluminescence spectrum of a quantum dot and a normalized ultraviolet-visible absorption spectrum of the color filter material, a range of a photoluminescence peak wavelength of the quantum dot and a range of a wavelength of maximum absorbance of the color filter material do not overlap with each other,

wherein the color filter material is included in an amount of less than or equal to 1 part by weight per 10 parts by weight of the plurality of quantum dots, and

wherein the quantum dot comprises a core comprising a first semiconductor nanocrystal and a shell disposed over the core and comprising a second semiconductor nanocrystal that is different from the first semiconductor nanocrystal.

Assignments (5)
CORRECTIVE ASSIGNMENT TO CORRECT THE RECEIVING PARTY'S DATA PREVIOUSLY RECORDED ON REEL 045880 FRAME 0215. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Aug 1, 2018
From: SAMSUNG DISPLAY CO., LTD.; SAMSUNG SDI CO., LTD.
To: SAMSUNG DISPLAY CO., LTD.; SAMSUNG SDI CO., LTD.; SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 046686/0414 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 23, 2018
From: SAMSUNG DISPLAY CO., LTD.; SAMSUNG SDI CO., LTD.
To: SAMSUNG DISPLAY CO., LTD.; SAMSUNG SDI CO., LTD.
Reel/Frame 045880/0215 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2018
From: SAMSUNG ELECTRONICS CO., LTD.
To: SAMSUNG DISPLAY CO., LTD.; SAMSUNG SDI CO., LTD.
Reel/Frame 045289/0852 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 20, 2018
From: SAMSUNG ELECTRONICS CO., LTD.
To: SAMSUNG DISPLAY CO., LTD.; SAMSUNG SDI CO., LTD.
Reel/Frame 045290/0125 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 3, 2016
From: YANG, HYEYEON; KIM, TAE HYUNG; PARK, SHANG HYEUN; JUN, SHIN AE; HAN, YONG SEOK; JANG, EUN JOO; CHUNG, DEUKSEOK
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 040827/0552 →
Priority Claims (1)
KR 10-2015-0146973 · Oct 21, 2015 · national
Continuity (1)
Related Publication 20170115561A1 · Apr 27, 2017