Organic-inorganic hybrid thin film and method for producing the same

Patent metadata

Field	Value
Publication number	US-9576876-B2
Application number	US-201314413754-A
Country	US
Kind code	B2
Filing date	Nov 4, 2013
Priority date	Aug 30, 2013
Publication date	Feb 21, 2017
Grant date	Feb 21, 2017

Abstract

The present invention relates to an organic-inorganic hybrid thin film and a method for preparing the same and more specifically to an organic-inorganic hybrid thin film including a stable new functional group and a method for preparing the organic-inorganic hybrid thin film that is formed by the molecular layer deposition method alternately using inorganic precursor and organic precursor.

First claim

We claim:

1. A hybrid organic/inorganic thin film, represented by Formula 1:
[ M - X - R 1- Y -] m -  [Formula 1]

where
m is 1 or more,
R1 is a substituted or an unsubstituted C 1-20 alkyl, C 5-20 cycloalkyl, or aryl or heteroaryl with an atomic number of 5-60,
M is selected from the group consisting of Zn, Sn, In, Cd, Ga, Al, Ti, Si, V, Mn, Fe, Co, Cu, Zr, Ru, Mo, Nb, and W,
X and Y are each selected from the group consisting of O, S, N, NH and CO, and
one of X and Y is S.

2. The hybrid organic/inorganic thin film in of claim 1 , which has a thickness of 1 Å to 500 Å.

3. The hybrid organic/inorganic thin film of claim 1 , wherein when an initial thickness of the hybrid organic/inorganic thin film is d0 and a thickness of the hybrid organic/inorganic thin film after standing under STP conditions for n hours is dn, the following relationship is satisfied:
( dn/d 0)≦0.1 where 0≦ n≦ 240.

4. A functional thin film, comprising:
the hybrid organic/inorganic thin film of claim 1 ; and
an oxide layer of a metal selected from the group consisting of Zn, Sn, In, Cd, Ga, Al, Ti, Si, V, Mn, Fe, Co, Cu, Zr, Ru, Mo, Nb, and W.

5. The functional thin film of claim 4 , wherein a thickness of the oxide layer ranges from 10 Å to 2000 Å.

6. The functional thin film of claim 4 , wherein, when an initial thickness of the functional thin film is D0 and a thickness of the functional thin film after standing under STP conditions for n hours is Dn, the following relationship is satisfied:
0≦( Dn/D 0)≦0.1 where 0≦ n≦ 240.

7. The functional thin film of claim 4 , which is suitable for encapsulation.

8. A method for preparing a hybrid organic/inorganic thin film, the method comprising:
(1) forming an inorganic molecular layer on a surface of a substrate using a first precursor compound of Formula 2:
M ( R 21)( R 22) . . . ( R 2 n )  [Formula 2]

where M is a metal selected from the group consisting of Zn, Sn, Cd, Ti, Si, V, Mn, Fe, Co, Cu, Zr, Ru, Mo, Nb, W, In, Ga, Al, and Tl,
n is determined according to an oxidation number state of the metal M, and
R21 to R2n are each independently C 1-20 alkyl, C 1-20 alkoxide, a chloride group, a hydroxyl group, an oxyhydroxide group, a nitrate group, a carbonate group, an acetate group or an oxalate group, and
(2) forming an organic molecular layer on the inorganic molecular layer via a reaction of a second precursor compound of Formula 3 with the inorganic molecular layer:
R 3- S - R 4- R 5  [Formula 3]

where R3 is hydrogen, COR6, C 1-20 alkyl, C 5-20 cycloalkyl, or aryl or heteroaryl with an atomic number of 5-60,
R4 is C 1-20 alkyl, C 5-20 cycloalkyl, or aryl or heteroaryl with an atomic number of 5-60,
R5 is at least one selected from the group consisting of a C 1-20 alkoxy group, an ether group, a carboxyl group, COR6, a thiol group, and an amine group, and
R6 is at least one selected from the group consisting of hydrogen, an alkoxy group, an ether group, a carboxyl group, a thiol group, and an amine group.

9. The method of claim 8 , wherein the second precursor compound is represented by formula 4:

where Z is a thiol group, Q is a thiol group or a hydroxyl group, and Z and Q are located at the ortho, meta or para position.

10. The method of claim 8 , wherein the second precursor compound is represented by formula 5:

11. The method of claim 8 , wherein the second precursor compound is represented by formula 6:

12. The method of claim 8 , further comprising
repeatedly performing the forming (1) and the forming (2).

13. The method of claim 8 , wherein the substrate is selected from the group consisting of glass, silicon and plastic.

14. The method of claim 8 , further comprising:
forming an oxide layer on the surface of the substrate prior to the forming (1).

15. The method of claim 8 , further comprising:
(3) forming an oxide layer of a metal selected from the group consisting of Zn, Sn, In, Cd, Ga, Al, Ti, Si, V, Mn, Fe, Co, Cu, Zr, Ru, Mo, Nb, and W by atomic layer deposition
wherein when an initial thickness of the hybrid organic/inorganic thin film is d0 and a thickness of the hybrid organic/inorganic thin film after standing under STP conditions for n hours is dn, the following relationship is satisfied:
0≦( dn/d 0)≦0.1, where 0≦ n≦ 240.

16. The method of claim 15 , wherein the forming (3) is repeatedly performed n2 times where n2 is 1 or more after repeatedly performing the forming (1) and the forming (2) n1 times where n1 is 1 or more.

17. The method of claim 15 , wherein the forming (1), the forming (2), and the forming (3) are repeatedly performed.

Assignees

• Iucf-Hyu (Industry-University Coop Found Hanyang University)
• Basf Coatings Gmbh

Inventors

• Sung Myung Mo
• Han Kyu Seok

Classifications

• H10W74/47

  comprising organic materials, e.g. plastics or resins · CPC title

• H10W74/15

  on active surfaces of flip-chip devices, e.g. underfills · CPC title

• H10W74/012

  of encapsulations on active surfaces of flip-chip devices, e.g. forming underfills · CPC title

• H10W74/147 Primary

  the encapsulations being multilayered · CPC title

• C07F3/06

  Zinc compounds · CPC title