IP Library › Granted Patent US 9,096,725

Granted Patent B2

US 9,096,725 · App. 12/766,074 · Granted Aug 4, 2015

Cross-linked polyazole, method of preparing the polyazole, electrode for fuel cell including the cross-linked polyazole, electrolyte membrane for fuel cell including the cross-linked polyazole, method of manufacturing the electrolyte membrane, and fuel cell including the cross-linked polyazole

Inventors: Seong-woo Choi (Yongin-si, KR); Jong-chan Lee (Seoul, KR); Jung-ock Park (Yongin-si, KR)

Assignees: SAMSUNG ELECTRONICS CO., LTD.; SNU R&D FOUNDATION

C08G73/18 C08G61/12 C08J5/2256 C08K5/357 C08L79/04 H01M8/103 H01M8/1027 H01M8/1048 H01M8/1072 H01M8/1081 H01M8/1088 C08G2261/126 C08G2261/312 C08G2261/3241 C08G2261/516 C08G2261/592 C08G2261/598 C08G2261/62 C08J2379/06 Y02E60/521

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Quick Facts

Patent No.: US 9,096,725
App. No.: 12/766,074
Granted: Aug 4, 2015
Kind: B2

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Abstract

A cross-linked polyazole, a method of preparing the cross-linked polyazole, an electrode and an electrolyte membrane for a fuel cell, which include the cross-linked polyazole, a method of manufacturing the electrolyte membrane, and a fuel cell including the cross-linked polyazole.

Claims (172)

1. A composition comprising: a polyazole including a first repeating unit comprising a repeating unit represented by one of the following formulas:

wherein Ar is selected from among the following groups:

an azole second repeating unit having at least one amino group; and a benzoxazine-based monomer, wherein, assuming that m and n represent the relative molar amount of the first repeating unit and the azole second repeating unit, respectively, in the polyazole such that m+n=1, m ranges from 0.1 to 0.9 and n ranges from 0.1 to 0.9:

and

wherein the azole second repeating unit comprises a repeating unit represented by

wherein, in Formula 2a, R 3 , R 3 ′, R 3 ″, R 3 ′″, R 4 , R 4 ′, R 4 ″, R 5 , R 5 ′, and R 5 ″ are each independently a hydrogen atom, an unsubstituted or substituted C1-C20 alkyl group, an unsubstituted or substituted C1-C20 alkoxy group, an unsubstituted or substituted C6-C20 aryl group, an unsubstituted or substituted C6-C20 aryloxy group, an unsubstituted or substituted C3-C20 heteroaryl group, or an unsubstituted or substituted C3-C20 heteroaryloxy group, wherein R 1 and R 2 may be linked to form a C4-C20 carbon ring or a C3-C20 hetero ring; and

L represents a linker.

2. The composition of claim 1 , wherein the amount of the polyazole is in the range of about 40 parts to about 210 parts by weight based on 100 parts by weight of the benzoxazine-based monomer.

3. The composition of claim 1 , wherein L in Formula 2a is —CH 2 —, —C(CH 3 ) 2 —, or —C(CF 3 ) 2 —.

4. The composition of claim 1 , wherein the polyazole is a block copolymer including the first repeating unit and the second repeating unit of Formula 2a.

5. The composition of claim 1 , wherein the polyazole has a degree of polymerization of about 1 to about 900.

6. The composition of claim 1 , wherein the polyazole comprises a block copolymer represented by Formula 3 below:

wherein, in Formula 3, R 1 , R 1 ′ and R 2 are hydrogen;

Ar is selected from among the following groups:

m is a number from 0.1 to 0.9;

a is 1;

R 3 , R 3 ′, R 3 ″, R 3 ′″, R 4 , R 4 ′, R 4 ″, R 5 , R 5 ′, and R 5 ″ are each independently a hydrogen atom, an unsubstituted or substituted C1-C20 alkyl group, an unsubstituted or substituted C1-C20 alkoxy group, an unsubstituted or substituted C6-C20 aryl group, an unsubstituted or substituted C6-C20 aryloxy group, an unsubstituted or substituted C3-C20 heteroaryl group, or an unsubstituted or substituted C3-C20 heteroaryloxy group, wherein R 1 and R 2 may be linked to form a C4-C20 carbon ring or a C3-C20 hetero ring;

L represents a linker;

n is a number from greater than 0 to 0.99; and

k represents a degree of polymerization of the polyazole and is a number from 10 to 300.

7. The composition of claim 1 , wherein the benzoxazine-based monomer comprises at least one compound selected from among the compounds represented by Formulae 6 through 11 below:

in Formula 6, R 1 through R 4 are each independently a hydrogen atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 6 -C 20 aryloxy group, a substituted or unsubstituted C 2 -C 20 heteroaryl group, a substituted or unsubstituted C 2 -C 20 heteroaryloxy group, a substituted or unsubstituted C 4 -C 20 carbon ring group, a substituted or unsubstituted C 4 -C 20 carbocyclic alkyl group, a substituted or unsubstituted C 2 -C 20 heterocyclic group, a halogen atom, a hydroxyl group, or a cyano group; and

R 5 is a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 6 -C 20 aryloxy group, a substituted or unsubstituted C 7 -C 20 arylalkyl group, a substituted or unsubstituted C 2 -C 20 heteroaryl group, a substituted or unsubstituted C 2 -C 20 heteroaryloxy group, a substituted or unsubstituted C 2 -C 20 heteroarylalkyl group, a substituted or unsubstituted C 4 -C 20 carbocyclic group, a substituted or unsubstituted C 4 -C 20 carbocyclic alkyl group, a substituted or unsubstituted C 2 -C 20 heterocyclic group, or a substituted or unsubstituted C 2 -C 20 heterocyclic alkyl group,

in Formula 7, R 5 ′ is a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 6 -C 20 aryloxy group, a substituted or unsubstituted C 7 -C 20 arylalkyl group, a substituted or unsubstituted C 2 -C 20 heteroaryl group, a substituted or unsubstituted C 2 -C 20 heteroaryloxy group, a substituted or unsubstituted C 2 -C 20 heteroarylalkyl group, a substituted or unsubstituted C 4 -C 20 carbocyclic group, a substituted or unsubstituted C 4 -C 20 carbocyclic alkyl group, a substituted or unsubstituted C 2 -C 20 heterocyclic group, or a substituted or unsubstituted C 2 -C 20 heterocyclic alkyl group; and

R 6 is selected from the group consisting of a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C 2 -C 20 alkenylene group, a substituted or unsubstituted C 2 -C 20 alkynylene group, a substituted or unsubstituted C 6 -C 20 arylene group, a substituted or unsubstituted C 2 -C 20 heteroarylene group, —C(═O)—, and —SO 2 —,

in Formula 8, A, B, C, D and E are all carbon; or one or two of A, B, C, D and E is nitrogen and the others are carbon; and

R 1 and R 2 are linked to form a ring, wherein the ring is a C 6 -C 10 carbon ring group, a C 3 -C 10 heteroaryl group, a fused C 3 -C 10 heteroaryl group, a C 3 -C 10 heterocyclic group or a fused C 3 -C 10 heterocyclic group;

in Formula 9, A is a substituted or unsubstituted C 1 -C 20 heterocyclic group, a substituted or unsubstituted C 4 -C 20 cycloalkyl group, or a substituted C 1 -C 20 alkyl group, and wherein A includes at least one oxazine moiety; and

R 1 through R 8 are each independently a hydrogen atom, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group, a C 6 -C 20 aryloxy group, a C 1 -C 20 heteroaryl group, a C 1 -C 20 heteroaryloxy group, a C 4 -C 20 cycloalkyl group, a C 1 -C 20 heterocyclic group, a halogen atom, a cyano group, or a hydroxy group,

in Formula 10, R 1 and R 2 are each independently a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group, a C 6 -C 20 aryloxy group or a group represented by Formula 10A below,

in Formulae 10 and 10A, R 3 is a hydrogen atom, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group, a C 6 -C 20 aryloxy group, a halogenated C 6 -C 20 aryl group, a halogenated C 6 -C 20 aryloxy group, a C 1 -C 20 heteroaryl group, a C 1 -C 20 heteroaryloxy group, a halogenated C 1 -C 20 heteroaryl group, a halogenated C 1 -C 20 heteroaryloxy group, a C 4 -C 20 carbon ring group, a halogenated C 4 -C 20 carbon ring group, a C 1 -C 20 heterocyclic group or a halogenated C 1 -C 20 heterocyclic group,

in Formula 11, at least two adjacent groups selected from among R 2 , R 3 and R 4 are linked to form a group represented by Formula 12A below, and the non-selected, remaining group is a hydrogen atom, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group, a C 6 -C 20 aryloxy group, a halogenated C 6 -C 20 aryl group, a halogenated C 6 -C 20 aryloxy group, a C 1 -C 20 heteroaryl group, a C 1 -C 20 heteroaryloxy group, a halogenated C 1 -C 20 heteroaryl group, a halogenated C 1 -C 20 heteroaryloxy group, a C 4 -C 20 carbon ring group, a halogenated C 4 -C 20 carbon ring group, a C 1 -C 20 heterocyclic group or a halogenated C 1 -C 20 heterocyclic group; and

at least two adjacent groups selected from among R 5 , R 6 and R 7 are linked to form the group represented by Formula 12A below, and the non-selected, remaining group is a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group, a C 6 -C 20 aryloxy group, a halogenated C 6 -C 20 aryl group, a halogenated C 6 -C 20 aryloxy group, a C 1 -C 20 heteroaryl group, a C 1 -C 20 heteroaryloxy group, a halogenated C 1 -C 20 heteroaryl group, a halogenated C 1 -C 20 heteroaryloxy group, a C 4 -C 20 carbon ring group, a halogenated C 4 -C 20 carbon ring group, a C 1 -C 20 heterocyclic group or a halogenated C 1 -C 20 heterocyclic group, and

in Formula 12A, R 1 is a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 6 -C 20 aryloxy group, a substituted or unsubstituted C 7 -C 20 arylalkyl group, a substituted or unsubstituted C 2 -C 20 heteroaryl group, a substituted or unsubstituted C 2 -C 20 heteroaryloxy group, a substituted or unsubstituted C 2 -C 20 heteroarylalkyl group, a substituted or unsubstituted C 4 -C 20 carbon ring group, a substituted or unsubstituted C 4 -C 20 carbocyclic alkyl group, a substituted or unsubstituted C 2 -C 20 heterocyclic group, or a substituted or unsubstituted C 2 -C 20 heterocyclic alkyl group; and

* denotes the sites at which the at least two adjacent groups selected from among R 2 , R 3 and R 4 of Formula 11 and the at least two adjacent groups selected from among R 5 , R 6 and R 7 are linked, respectively.

8. A cross-linked polyazole obtained through a cross-linking reaction of the composition of claim 1 .

9. A method of preparing the cross-linked polyazole of claim 8 , the method comprising:

mixing a polyazole including a first repeating unit comprising a repeating unit represented by one of the following formulas:

wherein Ar is selected from among the following groups:

an azole second repeating unit having at least one amino group, a benzoxazine-based monomer and a phosphoric acid-based material to obtain a mixture, wherein, assuming that m and n represent the relative molar amount of the first repeating unit and the azole second repeating unit, respectively, in the polyazole such that m+n=1, m ranges from 0.1 to 0.9 and n ranges from 0.1 to 0.9; and

thermally treating the mixture,

wherein the azole second repeating unit comprises a repeating unit represented by

L represents a linker.

10. The method of claim 9 , wherein the thermally treating is performed at a temperature of about 60 to about 250° C.

11. The method of claim 9 , wherein the phosphoric acid-based material comprises at least one material selected from the group consisting of polyphosphoric acid, phosphonic acid (H 3 PO 3 ), ortho-phosphoric acid (H 3 PO 4 ), pyro-phosphoric acid (H 4 P 2 O 7 ), triphosphoric acid (H 5 P 3 O 10 ), meta-phosphoric acid, and a derivative thereof.

12. The method of claim 9 , wherein the polyazole including the first repeating unit and the azole second repeating unit having at least one amino group is prepared through polymerization using a material that generates phosphoric acid when hydrolyzed.

13. The method of claim 12 , wherein the material that generates phosphoric acid when hydrolyzed comprises polyphosphoric acid.

14. The method of claim 9 , wherein the polyazole including the first repeating unit and the azole second repeating unit having at least one amino group is prepared by a method comprising:

mixing biphenyl-3,3′,4,4′-tetraaminetetrahydrochloride and phosphoric acid, and thermally treating the mixture at a temperature of about 60 to about 250° C. to obtain a (2,2-(m-phenylene)-5,5-bibenzimidazole) oligomer; and

mixing the (2,2-(m-phenylene)-5,5-bibenzimidazole) oligomer with 3,4-diaminobenzoic acid and thermally treating the mixture at a temperature of about 60 to about 250° C.

15. An electrolyte membrane for a fuel cell, the electrolyte membrane comprising a composition comprising: a polyazole including a first repeating unit comprising a repeating unit represented by one of the following formulas:

wherein Ar is selected from among the following groups:

an azole second repeating unit; and a benzoxazine-based monomer, wherein, assuming that m and n represent the relative molar amount of the first repeating unit and the azole second repeating unit, respectively, in the polyazole such that m+n=1, m is a number from 0.1 to 0.9 and n is a number from 0.1 to 0.9:

and wherein the azole second repeating unit comprises a repeating unit represented by Formula 2a:

L represents a linker.

16. An electrolyte membrane for a fuel cell, the electrolyte membrane comprising a cross-linked polyazole obtained through a cross-linking reaction of a composition comprising: a polyazole including a first repeating unit comprising a repeating unit represented by one of the following formulae:

wherein Ar is selected from among the following groups:

and

wherein the azole second repeating unit comprises a repeating unit represented by Formula 2a:

L represents a linker.

17. A method of manufacturing an electrolyte membrane for a fuel cell of claim 16 , the method comprising:

mixing a polyazole including a first repeating unit comprising a repeating unit represented by one of the following formulae:

wherein Ar is selected from among the following groups:

casting the mixture on a substrate and thermally treating the cast mixture to obtain a thermally-treated product;

impregnating the thermally-treated product with the phosphoric acid-based material to obtain a resulting product; and

drying the resulting product,

wherein the azole second repeating unit comprises a repeating unit represented by Formula 2a:

L represents a linker.

18. The method of claim 17 , further comprising treating the thermally-treated product in a constant-temperature and constant humidity condition at a temperature of about −20 to about 30° C. and a relative humidity of about 5 to about 50%.

19. The method of claim 17 , wherein, the mixing of the polyazole including the first repeating unit and the azole second repeating unit having at least one amino group, the benzoxazine-based monomer and the phosphoric acid-based material comprises: mixing the polyazole with the phosphoric acid-based material at a temperature of about 100° C. to about 160° C. to obtain a blend, and mixing the blend with the benzoxazine-based monomer to obtain the mixture.

20. The method of claim 17 , wherein the phosphoric acid-based material comprises at least one material selected from the group consisting of polyphosphoric acid, phosphonic acid (H 3 PO 3 ), ortho-phosphoric acid (H 3 PO 4 ), pyro-phosphoric acid (H 4 P 2 O 7 ), triphosphoric acid (H 5 P 3 O 10 ), meta-phosphoric acid, and a derivative thereof.

21. The method of claim 17 , wherein the polyazole including the first repeating unit and the azole second repeating unit having at least one amino group is prepared through polymerization using a material that generates phosphoric acid when hydrolyzed.

22. The method of claim 21 , wherein the material that generates phosphoric acid when hydrolyzed comprises polyphosphoric acid.

23. The method of claim 17 , wherein the polyazole including the first repeating unit and the azole second repeating unit having at least one amino group is prepared by a method comprising:

mixing biphenyl-3,3′,4,4′-tetraaminetetrahydrochloride and polyphosphoric acid, and thermally treating the mixture at a temperature of about 60 to about 250° C. to obtain a (2,2-(m-phenylene)-5,5-bibenzimidazole) oligomer; and

mixing the (2,2-(m-phenylene)-5,5-bibenzimidazole) oligomer with 3,4-diaminobenzoic acid and thermally treating the mixture at a temperature of about 60 to about 250° C.

24. An electrode for a fuel cell, the electrode comprising the composition of claim 1 .

25. An electrolyte for a fuel cell, the electrolyte comprising the cross-linked polyazole of claim 8 .

26. A fuel cell comprising:

a cathode;

an anode; and

an electrolyte membrane according to claim 15 disposed between the cathode and the anode.

27. A fuel cell comprising:

a cathode;

an anode; and

an electrolyte membrane according to claim 16 disposed between the cathode and the anode.

28. The electrolyte membrane of claim 15 , wherein the amount of the polyazole is in the range of about 40 parts to about 210 parts by weight based on 100 parts by weight of the benzoxazine-based monomer.

29. The electrolyte membrane of claim 15 , wherein L in Formula 2a is —CH 2 —, —C(CH 3 ) 2 —, or —C(CF 3 ) 2 —.

30. The electrolyte membrane of claim 15 , wherein the polyazole is a block copolymer including the first repeating unit and the second repeating unit of Formula 2a.

31. The electrolyte membrane of claim 15 , wherein the polyazole has a degree of polymerization of about 1 to about 900.

32. The electrolyte membrane of claim 15 , wherein the polyazole comprises a block copolymer represented by Formula 3 below:

wherein, in Formula 3, R 1 , R 1 ′ and R 2 are hydrogen;

Ar is selected from among the following groups:

m is a number from 0.1 to 0.9;

a is 1;

L represents a linker;

n is a number from 0.1 to 0.9; and

k represents a degree of polymerization of the polyazole and is a number from 10 to 300.

33. The electrolyte membrane of claim 15 , wherein the benzoxazine-based monomer comprises at least one compound selected from among the compounds represented by Formulae 6 through 11 below:

in Formula 8, A, B, C, D and E are all carbon; or one or two of A, B, C, D and E is nitrogen and the others are carbon; and

in Formula 10, R 1 and R 2 are each independently a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group, a C 6 -C 20 aryloxy group or a group represented by Formula 10A below,

34. The electrolyte membrane of claim 16 , wherein the amount of the polyazole is in the range of about 40 parts to about 210 parts by weight based on 100 parts by weight of the benzoxazine-based monomer.

35. The electrolyte membrane of claim 16 , wherein L in Formula 2a is —CH 2 —, —C(CH 3 ) 2 —, or —C(CF 3 ) 2 —.

36. The electrolyte membrane of claim 16 , wherein the polyazole is a block copolymer including the first repeating unit and the second repeating unit of Formula 2a.

37. The electrolyte membrane of claim 16 , wherein the polyazole has a degree of polymerization of about 1 to about 900.

38. The electrolyte membrane of claim 16 , wherein the polyazole comprises a block copolymer represented by Formula 3 below:

wherein, in Formula 3, R 1 , R 1 ′ and R 2 are hydrogen; Ar is selected from among the following groups:

m is a number from 0.1 to 0.9;

a is 1;

L represents a linker;

n is a number from 0.1 to 0.9; and

k represents a degree of polymerization of the polyazole and is a number from 10 to 300.

39. The electrolyte membrane of claim 16 , wherein the benzoxazine-based monomer comprises at least one compound selected from among the compounds represented by Formulae 6 through 11 below:

R 6 is selected from the group consisting of a substituted or unsubstituted C 1 -C 20 alkylene group, a substituted or unsubstituted C 2 -C 20 alkenylene group, a substituted or unsubstituted C 2 ′ C 20 alkynylene group, a substituted or unsubstituted C 6 -C 20 arylene group, a substituted or unsubstituted C 2 -C 20 heteroarylene group, —C(═O)—, and —SO 2 —,

in Formula 8, A, B, C, D and E are all carbon; or one or two of A, B, C, D and E is nitrogen and the others are carbon; and

in Formula 10, R 1 and R 2 are each independently a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group, a C 6 -C 20 aryloxy group or a group represented by Formula 10A below,

40. The membrane of claim 15 , wherein the molar ratio of the first repeating unit to the second repeating unit is about 8:2, about 5:5, or about 2:8.

41. The membrane of claim 16 , wherein the molar ratio of the first repeating unit to the second repeating unit is about 8:2, about 5:5, or about 2:8.

42. The membrane of claim 16 , wherein the benzoxazine-based monomer comprises at least one compound selected from among the compounds represented by Formulae 6 through 11:

in Formula 6, R 1 , R 2 and R 4 are each independently a hydrogen atom, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 6 -C 20 aryloxy group, a substituted or unsubstituted C 2 -C 20 heteroaryl group, a substituted or unsubstituted C 2 -C 20 heteroaryloxy group, a substituted or unsubstituted C 4 -C 20 carbon ring group, a substituted or unsubstituted C 4 -C 20 carbocyclic alkyl group, a substituted or unsubstituted C 2 -C 20 heterocyclic group, a halogen atom, a hydroxyl group, or a cyano group;

R 3 is independently a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 6 -C 20 aryloxy group, a substituted or unsubstituted C 2 -C 20 heteroaryloxy group, a substituted or unsubstituted C 4 -C 20 carbocyclic alkyl group, a halogen atom, a hydroxyl group, or a cyano group; and

in Formula 7, R 5 ′ is a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 6 -C 20 aryloxy group, or a substituted or unsubstituted C 2 -C 20 heteroaryloxy group; and

in Formula 8, A, B, C, D and E are all carbon; or one or two of A, B, C, D and E is nitrogen and the others are carbon; and

in Formula 10, R 1 and R 2 are each independently a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group, a C 6 -C 20 aryloxy group or a group represented by Formula 10A below,

43. An electrolyte membrane for a fuel cell, the electrolyte membrane comprising a cross-linked polyazole obtained through a cross-linking reaction of a composition comprising: a polyazole including a first repeating unit comprising a repeating unit represented by one of the following formulae:

wherein Ar is selected from among the following groups:

wherein the azole second repeating unit comprises a repeating unit represented by Formula 2a:

L represents a linker, and

wherein the benzoxazine-based monomer comprises at least one compound selected from:

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 26, 2010

From: CHOI, SEONG-WOO; LEE, JONG-CHAN; PARK, JUNG-OCK

To: SAMSUNG ELECTRONICS CO., LTD.; SNU R&D FOUNDATION

Reel/Frame 024291/0424 →

Priority Claims (1)

KR 10-2009-0036233 · Apr 24, 2009 · national

Continuity (1)

Related Publication 20100273087A1 · Oct 28, 2010