Indium oxoalkoxides for producing coatings containing indium oxide
View Patent ↗The present invention relates to halogenated indium oxo alkoxides of the generic formula In 6 O 2 X 6 (OR) 6 (R′CH(O)COOR″) 2 (HOR) x (HNR′″ 2 ) y where X═F, Cl, Br and/or I, R═C1-C15-alkyl, C1-C15-alkenyl, C1-C15-alkynyl, C1-C15-alkoxyalkyl, C6-C15-aryl- and/or C7-C15-alkoxyaryl, R′═C1-C15-alkyl, C1-C15-alkenyl, C1-C15-alkynyl, C1-C15-alkoxyalkyl, C6-C15-aryl- and/or C7-C15-alkoxyaryl, R″═C1-C15-alkyl, C1-C15-alkenyl, C1-C15-alkynyl, C1-C15-alkoxyalkyl, C6-C15-aryl- and/or C7-C15-alkoxyaryl, R′″═C1-C15-alkyl, C1-C15-alkenyl, C1-C15-alkynyl, C1-C15-alkoxyalkyl, C6-C15-aryl- and/or C7-C15-alkoxyaryl, x=0 to 10 and y=0 to 10, to processes for preparation thereof and to use thereof.
1. An indium oxo alkoxide of formula:
In 6 O 2 X 6 (OR) 6 (R′CH(O)COOR″) 2 (HOR) x (HNR″′ 2 ) y ,
wherein X is at least one selected from the group consisting of F, Cl, Br and I;
R is at least one selected from the group consisting of C1-C15-alkyl, C1-C15-alkenyl, C1-C15-alkynyl, C1-C15-alkoxyalkyl, C6-C15-aryl- and C7-C15-alkoxyaryl;
R′ is at least one selected from the group consisting of C1-C15-alkyl, C1-C15-alkenyl, C1-C15-alkynyl, C1-C15-alkoxyalkyl, C6-C15-aryl- and C7-C15-alkoxyaryl;
R″ is at least one selected from the group consisting of C1-C15-alkyl, C1-C15-alkenyl, C1-C15-alkynyl, C1-C15-alkoxyalkyl, C6-C15-aryl- and C7-C15-alkoxyaryl;
R″′ is at least one selected from the group consisting of C1-C15-alkyl, C1-C15-alkenyl, C1-C15-alkynyl, C1-C15-alkoxyalkyl, C6-C15-aryl- and C7-C15-alkoxyaryl;
x is of from 0 to 10; and
y is of from 0 to 10.
2. The indium oxo alkoxide of claim 1 , having formula:
In 6 O 2 Cl 6 (OCH 2 CH 3 ) 6 (CH 3 CH(O)COOCH 2 CH 3 ) 2 (HN(CH 3 ) 2 ) 2 .
3. A process for preparing the indium oxo alkoxide of claim 1 , comprising
converting an indium(III) salt of formula InX 3
first in presence of an alcohol ROH
and in presence of a secondary amine of formula HNR′″ 2
to obtain an indium(III) halogen alkoxide adduct or an indium(III) oxo halogen alkoxide adduct, and
reacting the indium(III) halogen alkoxide adduct or the indium(III) oxo halogen alkoxide adduct with at least one α-hydroxy ester R′CH(OH)COOR″.
4. The process of claim 3 ,
wherein the indium(III) halogen alkoxide adduct formed as an intermediate is of formula InX(OR) 2 (HNR′″ 2 ) y ,
wherein X═F, Cl, Br, or I;
R is at least one selected from the group consisting of C1-C15-alkyl, C1-C15-alkenyl, C1-C15-alkynyl, C1-C15-alkoxyalkyl, C6-C15-aryl- and C7-C15-alkoxyaryl;
R′″ is at least one selected from the group consisting of C1-C15-alkyl, C1-C15-alkenyl, C1-C15-alkynyl, C1-C15-alkoxyalkyl, C6-C15-aryl- and C7-C15-alkoxyaryl; and
y is of from 0 to 10.
5. The process of claim 4 , wherein the indium(III) halogen alkoxide adduct is at least one selected from the group consisting of InCl(OCH 3 ) 2 (HNMe 2 ) 2 , InCl(OCH 2 CH 3 ) 2 (HNMe 2 ) 2 , InCl(OCH 2 CH 2 CH 3 ) 2 (HNMe 2 ) 2 , InCl(OCH(CH 3 ) 2 ) 2 (HNMe 2 ) 2 , InCl(OCH 2 CH 2 CH 2 CH 3 ) 2 (HNMe 2 ) 2 , InCl(OCH(CH 3 )(CH 2 CH 3 )) 2 (HNMe 2 ) 2 , and InCl(OC(CH 3 ) 3 ) 2 (HNMe 2 ) 2 .
6. The process of claim 3 , wherein the a-hydroxy ester is at least one selected from the group consisting of methyl lactate, ethyl lactate, n-propyl lactate, and n-butyl lactate.
7. The process of claim 3 , wherein the process is performed in a solution comprising an alcohol, and the alcohol is at least one selected from the group consisting of HOCH 3 , HOCH 2 CH 3 , HOCH 2 CH 2 CH 3 , HOCH(CH 3 ) 2 , HOCH 2 CH 2 CH 2 CH 3 , HOCH(CH 3 )(CH 2 CH 3 ), and HOC(CH 3 ) 3 .
8. The indium oxo alkoxide of claim 1 , wherein the indium oxo alkoxide is suitable for producing an indium oxide-containing coating.
9. The indium oxo alkoxide of claim 1 , wherein the indium oxo alkoxide is suitable for producing a liquid coating composition.
10. The indium oxo alkoxide of claim 1 , wherein the indium oxo alkoxide is suitable for producing an electronic component.
11. The indium oxo alkoxide of claim 10 , wherein the electronic component is at least one selected from the group consisting of a transistor, a display, a RFID tag, a circuit, a diode, a sensor, and a solar cell.
12. The indium oxo alkoxide of claim 1 , wherein X═Cl.
13. The indium oxo alkoxide of claim 1 , wherein R is at least one selected from the group consisting of —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH 2 CH 2 CH 3 , —CH 2 CH(CH 3 ) 2 , —CH(CH 3 )(CH 2 CH 3 ), and —C(CH 3 ) 3 .
14. The indium oxo alkoxide of claim 1 , wherein R is at least one selected from the group consisting of —CH 2 CH 2 —OCH 3 , —CH 2 CH 2 —OCH 2 CH 3 , —CH 2 CH 2 —OCH 2 CH 2 CH 3 , —CH 2 CH 2 —OCH(CH 3 ) 2 , —CH 2 CH 2 —OCH 2 CH 2 CH 2 CH 3 , —CH 2 CH 2 —OCH 2 CH(CH 3 ) 2 , —CH 2 CH 2 —OCH(CH 3 )(CH 2 CH 3 ), and —CH 2 CH 2 —OC(CH 3 ) 3 .
15. The indium oxo alkoxide of claim 1 , wherein R′ is at least one selected from the group consisting of —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH 2 CH 2 CH 3 , —CH 2 CH(CH 3 ) 2 , —CH(CH 3 )(CH 2 CH 3 ), and —C(CH 3 ) 3 .
16. The indium oxo alkoxide of claim 1 , wherein R″ is at least one selected from the group consisting of —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH 2 CH 2 CH 3 , —CH 2 CH(CH 3 ) 2 , —CH(CH 3 )(CH 2 CH 3 ), and —C(CH 3 ) 3 .
17. The indium oxo alkoxide of claim 1 , wherein R″′ is at least one selected from the group consisting of —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH(CH 3 ) 2 , —CH 2 CH 2 CH 2 CH 3 , —CH 2 CH(CH 3 ) 2 , —CH(CH 3 )(CH 2 CH 3 ), and —C(CH 3 ) 3 .
18. The indium oxo alkoxide of claim 1 , wherein x is of from 0 to 5 and y is of from 0 to 5.
19. The indium oxo alkoxide of claim 1 , wherein x is of from 1 to 3, and y is of from 1 to 3.
20. The process of claim 3 , wherein a molar ratio of the α-hydroxy ester R′CH(OH)COOR″ to the indium(III) salt is greater than 0.33:1.