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1. WO2000031163 - POLY(ARYLENE ETHER) HOMOPOLYMER COMPOSITIONS AND METHODS OF MANUFACTURE THEREOF

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[ EN ]

We claim:

1. A poly (arylene ether) having the structure:


wherein Y is a first divalent arylene radical selected from a first group consisting of:

and mixtures thereof;

Ar is a second divalent arylene radical selected from a second group consisting of:

and mixtures thereof;

n is between 1 and 200; and

Z is either H, CH3 or is a monovalent arylene radical selected from the group consisting of:

2. The poly (arylene ether) of Claim 1 wherein: Y has the structure:


and; Ar has the structure


3. The poly (arylene ether) as in Claim 2 wherein n is between approximately 5 and 60.

4. The poly (arylene ether) as in Claim 2 wherein n is between approximately 10 and 50.

5. The poly (arylene ether) as in Claim 1 wherein:

Y has the structure:

and; Ar has the structure:


6. The poly(arylene ether) as in Claim 5 wherein n is between approximately 5 and 60.

7. The poly (arylene ether) as in Claim 5 wherein n is between approximately 10 and 50.

8. A process for producing a poly (arylene ether) having the structure:


wherein Y is a first divalent arylene radical selected from a first group consisting of:

and mixtures thereof;

Ar is a second divalent arylene radical selected from a second group consisting of:

and mixtures thereof;

n is between 1 and 200; and Z is hydrogen, a methyl group or a

monovalent arylene radical selected from the

group consisting of:


comprising the steps of:

charging a reaction vessel with a first monomer of the structure HO—Y—OH, a second monomer of the structure, F—Ar—F and a solvent, wherein a reaction mixture is provided; and

heating said reaction mixture for a first time to provide polymerization of said monomers.

9. The process for producing a poly (arylene ether) as in Claim 8 wherein heating said reaction mixture comprises heating to a first temperature sufficiently high to begin azeotropic distillation of said reaction mixture to provide an azeotropic distillate.

10. A process for producing a poly (arylene ether) as in Claim 9 wherein heating said reaction mixture to a first temperature comprises removing a portion of said azeotropic distillate, wherein the first temperature is increased to a second temperature.

11. A process for producing a poly (arylene ether) as in Claim 8 wherein said solvent is a mixture of a first solvent selected from the group consisting essentially of N-methyl-2-pyrrolidinone (NMP), N,N-dimethyl acetamide (DMAC) and sulfolane, and a second solvent selected from the group consisting essentially of toluene and benzene.

12. A process for producing a poly (arylene ether) as in Claim 11 wherein said solvent is a mixture of sulfolane and toluene.

13. A process for producing a poly (arylene ether) as in Claim 8 wherein the reaction vessel is charged with

4-fluoro-3'-(4-fluorobenzoyl)tolane and

9,9'-bis(4-hydroxyphenyl)-fluorene having a 1:1 molar ratio.

14. A process for producing a poly (arylene ether) as in Claim 8 wherein the reaction vessel is charged with

3,3'-bis(4-fluorobenzoyl)tolane and

9,9'-bis(4-hydroxyphenyl)-fluorene having a 1:1 molar ratio.

15. A process for producing a poly (arylene ether) as in Claim 8 wherein the reaction vessel is charged with

4-fluoro-3'-(4-fluorobenzoyl)tolane and α,δ-bis(4-hydroxy) sexiphenylene having a 1:1 molar ratio.

16. A process for producing a poly (arylene ether) as in Claim 8 comprising providing methyl chloride gas to the reaction mixture, after the first time.

17. A microelectronic device comprising a dielectric layer disposed overlying a surface, wherein said dielectric layer comprises a poly (arylene ether) having repeating units of the structure:


wherein Y is a first divalent arylene radical selected from a first group consisting of:

and mixtures thereof;

Ar is a second divalent arylene radical selected from a second group consisting of:

and mixtures thereof; and

n is between 1 and 200; and

Z is either H, CH3 or is a monovalent arylene radical selected from the group consisting of:

18. A microelectronic device comprising a dielectric layer, as in Claim 17 wherein said surface comprises silicon oxide and/or aluminum, and wherein said dielectric layer has an adhesion of at least 7,500 pounds per square inch to said surface, a dielectric constant less than 3.0 and a glass transition temperature of at least 350°C.

19. A microelectronic device comprising a dielectric layer, as in Claim 18 wherein said dielectric layer has a film thickness uniformity of at least 99 per cent and a gap fill ability, for gaps having a depth of up to 0.8 micron, of less than or equal to 0.25 micron.

20. A microelectronic device comprising a dielectric layer, as in Claim 17 wherein:

Y of said poly (arylene ether) has the structure:


; and

Ar of said poly (arylene ether) has the structure


21. A microelectronic device comprising a dielectric layer, as in Claim 20 wherein n of said poly (arylene ether) is between approximately 10 and 50.

22. A microelectronic device comprising a dielectric layer, as in Claim 21 wherein said surface comprises silicon oxide and/or aluminum, and wherein said dielectric layer has an adhesion of at least 8,000 pounds per square inch to said surface, a dielectric constant less than 3.0 and a glass transition temperature of at least 400°C.

23. A microelectronic device comprising a dielectric layer, as in Claim 22 wherein said dielectric layer has a film thickness uniformity of at least 99 per cent and a gap fill ability, for gaps having a depth of up to 0.8 micron, of less than or equal to 0.13 micron.

24. A microelectronic device comprising a dielectric layer, as in Claim 17 wherein:

Y of said poly (arylene ether) has the structure:


and

Ar of said poly (arylene ether) has the structure


25. A microelectronic device comprising a dielectric layer, as in Claim 24 wherein n of said poly (arylene ether) is between approximately 10 and 50.

26. A microelectronic device comprising a dielectric layer, as in Claim 25 wherein said surface comprises silicon oxide and/or aluminum, and wherein said dielectric layer has an adhesion of at least 8,000 pounds per square inch to said surface, a dielectric constant less than 3.0 and a glass transition temperature of at least 400°C.

27. A microelectronic device comprising a dielectric layer, as in Claim 24 wherein said dielectric layer has a film thickness uniformity of at least 99 per cent and a gap fill ability, for gaps having a depth of up to 0.8 micron, of less than or equal to 0.13 micron.

28. A method for synthesizing a fluoro-substituted- (4-fluorobenzoyl) tolane comprising the conversion of a bromo-4'-fluorobenzophenone in the presence of 1-ethynl-4- fluorobenzene, a catalyst, and a de-aerated, aprotic solvent to provide said fluoro-substituted- (4- fluorobenzoyl)tolane.

29. A method for synthesizing a fluoro-substituted- (4-fluorobenzoyl) tolane as in Claim 28 wherein said fluoro- substituted-(4-fluorobenzoyl) tolane is 4-fluoro-3'- (4-fluorobenzoyl) tolane and said bromo-4'- fluorobenzophenone is 3-bromo-4'-fluorobenzophenone.

30. A method for synthesizing a fluoro-substituted- (4-fluorobenzoyl)tolane as in Claim 28 wherein said fluoro- substituted-(4-fluorobenzoyl) tolane is 4-fluoro-4'- (4-fluorobenzoyl) tolane and said bromo-4'- fluorobenzophenone is 4-bromo-4'-fluorobenzophenone.

31. A method for synthesizing 4-fluoro-3'- (4-fluorobenzoyl)tolane comprising:

charging a reaction vessel with 3-bromobenzoic acid, thionyl chloride and fluorobenzene to provide a first reaction mixture;

cooling said first reaction mixture and adding anhydrous aluminum chloride to provide a second reaction mixture;

heating said second reaction mixture wherein a 3- bromo-4'-fluorobenzophenone intermediate is provided; charging a second reaction vessel with said 3- bromo-4'-fluorobenzophenone intermediate, 1-ethynyl-4- fluorobenzene, triphenylphosphine, a catalyst and a de-aerated solvent to from a second reaction mixture; heating said second reaction mixture wherein 4- fluoro-3'-(4-fluorobenzoyl) tolane is provided.

32. A method for synthesizing a bis(4-fluorobenzoyl) tolane comprising:

charging a reaction vessel with a bromo-4'- fluorobenzophenone, a catalyst, and anhydrous THF as a solvent to provide a reaction mixture;

adding dropwise a solution of a bis (tri-n- butylstannyl) compound in said solvent;

heating said reaction mixture in an inert atmosphere to form crystals;

purifying said crystals wherein a bis(4- fluorobenzoyl) tolane is provided.

33. A method for synthesizing a bis(4-fluorobenzoyl)tolane as in Claim 32 wherein said bis(4-fluorobenzoyl)tolane is 4,4'-bis(4-fluorobenzoyl)tolane, said bromo-4'-fluorobenzophenone is 4-bromo-4'-fluorobenzophenone, and said bis(tri-n-butylstannyl) compound is bis (tri-n-butylstannyl) ethyne.

34. A method for synthesizing a bis (4-fluorobenzoyl)tolane as in Claim 32 wherein said bis (4-fluorobenzoyl)tolane is 3,3'-bis(4-fluorobenzoyl)tolane, said bromo-4'-fluorobenzophenone is 3-bromo-4'-fluorobenzophenone and said bis (tri-n-butylstannyl)compound is bis (tri-n-butylstannyl)acetylene.