IP Library Granted Patent US 7,064,176
Granted Patent B2
US 7,064,176 · App. 10/472,772 · Granted Jun 20, 2006

Coating material for electronic components

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Quick Facts
Patent No.
US 7,064,176
App. No.
10/472,772
Granted
Jun 20, 2006
Kind
B2
Abstract

The invention relates to novel polyhydroxyamide compounds that, in the form of their oxazoles, ane suited as a coating material, particularly for electronic components. The invention also relates to a method for producing these novel compounds and to the use thereof.

Claims (99)

1. A polyhydroxyamide of the following formula I or formula II:

wherein:

a=0 or 1, wherein, if a is 0, c is ≧1,

b=0–100,

c=0–50, wherein, if c is 0, a is 1,

d=1–100,

e=0–100,

f=0–100,

g=0–50,

h=0–100,

k=0–100,

m=0–100,

n=0–50,

p=0 or 1;

wherein:

q=1–100,

r=1–100,

s=0–100,

t=0–100,

u=0–100,

v=0–50,

w=0–100,

x=0–100,

y=0–100,

z=0–50;

each X is independently:

and α=0–100 and β=0–100, wherein α and β are not simultaneously 0;

each R 1 and R 2 is independently:

alkylene, arylene or cycloalkylene each of which is independently substituted or unsubstituted;

each Q is independently —O—, —S— or —NH—;

when at least one of A 1 or A 2 is bonded to Q or —NH—, each of A 1 and A 2 is independently:

H; alkylcarbonyl, alkenylcarbonyl, cycloalkenylcarbonyl, arylcarbonyl, aralkylcarbonyl, aralkenylcarbonyl or aralkynylcarbonyl, each of which is independently substituted or unsubstituted, wherein the carbonyl group is bonded to the aromatic, alkyl, alkenyl, cycloalkenyl or alkynyl group;

when at least one of A 1 or A 2 is bonded to —CO—, each of A 1 and A 2 is independently:

hydroxyl, alkoxy, alkenyloxy, aryloxy, cycloalkenyloxy, amino, alkylamino, alkenylamino, arylamino, arylalkenyloxy, or arylalkylamino, each of which is independently substituted or unsubstituted;

A 3 is:

H, alkylcarbonyl, alkenylcarbonyl, cycloalkenylcarbonyl, arylcarbonyl, aralkylcarbonyl, aralkenylcarbonyl or aralkynylcarbonyl, each of which is independently substituted or unsubstituted, wherein the carbonyl group is bonded to the aromatic or to the alkyl, alkenyl, cycloalkenyl or alkynyl group;

each of Y 1 and Y 2 is independently:

substituted or unsubstituted aryl, a substituted or unsubstituted polynuclear aromatic hydrocarbon compound, or alkyl, alkenyl, alkynyl, aralkyl, aralkenyl, or aralkynyl, each of which is substituted or unsubstituted;

each of Z 1 and Z 2 is independently:

aryl, aralkyl, aralkenyl, aralkynyl, heteroaryl or a polynuclear aromatic hydrocarbon compound.

2. The polyhydroxyamide as claimed in claim 1 , wherein, in formula I, b=0–20, c=0–10, d=4–40, e=0–20, f=0–20, g=0–10, h=0–20, k=0–20, m=0–20 or n=0–10;

and, in formula II, q=3–40, r=1–40, s=0–40, t=0–20, u=0–20, v=0–10, w=0–20, x=0–20, y=0–20 or z=0–10.

3. The polyhydroxyamide of claim 1 wherein α=0–10 or β=0–10.

4. The polyhydroxyamide of claim 1 , wherein at least one of R 1 or R 2 is:

—(CH 2 ) χ —

where

χ=1–20

δ=0–20,

ε=0–20, and

each R 3 and R 4 is independently: —H, or —(CH 2 ) φ —CH 3 , wherein φ=0–10 or —OH, and R 3 and R 4 are not simultaneously —OH.

5. The polyhydroxyamide of claim 1 , wherein each Q is independently —O— or —NH—.

6. The polyhydroxyamide of claim 1 , A 1 or A 2 , if A 1 or A 2 is bonded to Q or —NH—, and A 3 are:

wherein

φ=0–10; and

W=—CN, —C(CH 3 ) 3 , —(CH 2 ) φ —CH 3 , —(CF 2 ) φ —CF 3 , —O—(CH 2 ) φ —CH 3 , —O—(CF 2 ) φ —CF 3 ,

—CH═CH 2 , —C≡CH or

7. The polyhydroxyamide of claim 1 , wherein if at least one of A 1 or A 2 is bonded to —CO—, then at least one of A 1 or A 2 is:

wherein

φ=0–10;

and W=—CN, —C(CH 3 ) 3 , —(CH 2 ) φ —CH 3 , —(CF 2 ) φ —CF 3 , —O—(CH 2 ) φ —CH 3 , —O—(CF 2 ) φ —CF 3 ,

—CH═CH 2 , —C≡CH or

8. The polyhydroxyamide of claim 1 , wherein each Y 1 and Y 2 are independently:

wherein each R5, R6 and R7 is independently a substituent; and

wherein; if R 6 =—CH 2 —, then γ=0–10.

9. The polyhydroxyamide of claim 8 , wherein each R 5 is independently —H, —CN, —C(CH 3 ) 3 , —(CH 2 ) φ —CH 3 , —(CF 2 ) φ —CF 3 , —O—(CH 2 ) φ CH 3 , —O—(CF 2 ) φ —CF 3

wherein

φ=0–10 and W=—CN—, —C(CH 3 ) 3 , —(CH 2 ) φ —CH 3 , —(CF 2 ) φ —CF 3 , —O—(CH 2 ) φ —CH 3 , —O—(CF 2 ) φ —CF 3 ,

—CH═CH 2 , —C≡CH or

10. The polyhydroxyamide of claim 8 , wherein each R 6 is independently —O—, —CO—, —NR 7 —, —S—, —SO 2 —, —S 2 —, —CH 2 —, and wherein R 8 is a substituent

11. The polyhydroxyamide of claim 8 , wherein R 7 is —H

12. The polyhydroxyamide of claim 10 , wherein R 8 is an alkyl radical having 1 to 10 carbon atoms or an aryl radical.

13. The polyhydroxyamide of claim 1 , wherein each Z 1 and Z 2 are independently:

14. A polybenzoxazole, wherein the polybenzoxazole is produced by cyclization of hydroxyamide units of a polyhydroxyamide of claim 1 .

15. An electronic component comprising a coat comprising the polybenzoxazole of claim 14 .

16. The electronic component of claim 15 , wherein the electrical component is a memory chip, logic chip, flip chip, flash memory, multichip module, circuit board, microprocessor or embedded DRAM.

17. A process for the preparation of a polyhydroxyamide of claim 1 , the process comprising;

a) reacting at least one of a compound of the formula Z 1 (NH 2 ) 2 (OH) 2 or Z 2 (NH 2 ) 2 (OH) 2 with at least one of a compound of the formula Y 1 (COCl) 2 or Y 2 (COCl) 2 ,

b) reacting the product resulting from step a) with a compound of the formula X(QOH) 2 or X(QNH 2 ) 2 , and

c) optionally reacting the product obtained from step b) with a precursor compound for formula A 1 , A 2 and/or A 3 , wherein

Z 1 , Z 2 , Y 1 , Y 2 , A 1 , A 2 , A 3 and X are defined as in claim 1 .

18. A process for the preparation of a polybenzoxazoles of claim 1 , wherein a polyhydroxyamide of claim 1 is subjected to a thermal treatment.

19. The process of claim 18 , wherein the thermal treatment is effected at 250–450° C.

20. The process of claim 18 , wherein the thermal treatment is effected for 0.5–3 hours.

21. A process for coating a substrate, the process comprising applying at least one polyhydroxyamide of claim 1 to the substrate and heating the coated substrate in order to form a polybenzoxazole coat on the substrate.

22. The process of claim 21 , wherein the polyhydroxyamide is dissolved in an organic solvent before application to the substrate.

23. The process of claim 22 , wherein the organic solvent is acetone, cyclohexanone, diethylene glycol monoethyl ether, diethylene glycol diethyl ether, N-methylpyrrolidone, γ-butyrolactone, ethyl lactate, tetrahydrofuran, methyl acetate or a mixture thereof.

24. The process of claim 21 , wherein the polyhydroxyamide is applied to the substrate using a spin-coating treatment.

25. The process of claim 21 , wherein the substrate is a silica, silicon nitride, titanium, titanium nitride, tantalum or tantalum nitride surface.

26. The process of claim 21 , wherein the substrate is part of an electronic component.

27. A composition comprising a polyhydroxyamide of claim 1 and an organic solvent.

28. The composition of claim 27 , wherein the composition has a polyhydroxyamide content, based on the total composition, of 10–50% by weight.

29. The polyhydroxyamide of claim 1 , wherein, in X, wherein a=0–10 and β=0–10.

30. The process of claim 18 , wherein the thermal treatment is effected at 300–400° C.

31. The process of claim 18 , wherein the thermal treatment is effected at 300–350° C.

32. The process of claim 18 , wherein the thermal treatment is effected for 1–3 hours.

33. The process of claim 18 , wherein the thermal treatment is effected for 1–2 hours.

34. The composition of claim 27 , wherein the organic solvent is acetone, cyclohexanone, diethylene glycol monoethyl ether, diethylene glycol diethyl ether, N-methylpyrrolidone, γ-butyrolactone, ethyl lactate, tetrahydrofuran, methyl acetate or a mixture thereof.

35. The composition of claim 27 , wherein the polyhydroxyamide content is 20–40% by weight.

36. The composition of claim 27 , wherein the polyhydroxyamide content is about 20% by weight.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 30, 2015
From: INFINEON TECHNOLOGIES AG
To: POLARIS INNOVATIONS LIMITED
Reel/Frame 036723/0021 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 8, 2015
From: QIMONDA AG
To: INFINEON TECHNOLOGIES AG
Reel/Frame 035623/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 12, 2010
From: INFINEON TECHNOLOGIES AG
To: QIMONDA AG
Reel/Frame 023768/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 12, 2004
From: HALIK, MARCUS; LOWACK, KLAUS; SEZI, RECAI; WALTER, ANDREAS
To: INFINEON TECHNOLOGIES AG
Reel/Frame 014971/0558 →