Bis-o-nitrophenols derivatives and poly-o-hydroxyamides, polybenzoxazoles, materials, and microelectronic devices made therefrom

1. A bis-o-nitrophenol derivative comprising a compound having a Formula Ia:

wherein:

R 2 is a substituent independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:

wherein R 3 , R 4 , and R 5 are selected from the group consisting of: —F, —(CH 2 ) n —CH 3 , —(CF 2 ) n —CF 3 , with n being an integer from 0 to 10, and wherein at least one of the radicals R 2 is a tert-butoxycarbonyl group of Formula II; and

Z is a connector selected from the group consisting of a carbon-carbon single bond, a carbon-carbon bond common to both of said phenyl groups carrying said nitro and one of said OR 2 groups, a divalent alkyl radical with from 1 to 20 carbon atoms, a divalent aryl radical with from 6 to 20 carbon atoms, and a divalent aralkyl radical.

2. The bis-o-nitrophenol derivative according to claim 1 , wherein, if said connector of Z is a divalent alkyl radical, said divalent alkyl radical is branched.

3. The bis-o-nitrophenol derivative according to claim 1 , wherein, if said connector of Z is a divalent alkyl radical, said divalent alkyl radical is cyclic.

4. The bis-o-nitrophenol derivative according to claim 1 , wherein, if said connector of Z is a divalent alkyl radical, said divalent alkyl radical is straight-chain.

5. The bis-o-nitrophenol derivative according to claim 1 , wherein, if said connector of Z is a divalent aralkyl radical, said divalent aralkyl radical includes an alkyl group having from 1 to 10 carbon atoms.

6. The bis-o-nitrophenol derivative according to claim 1 , wherein, if said connector of Z is a divalent aralkyl radical, said divalent aralkyl radical includes an aryl group having from 6 to 20 carbon atoms.

7. The bis-o-nitrophenol derivative according to claim 1 , wherein said connector of Z includes at least one radical selected from the group consisting of a halogen, a pseudo-halogen, and an alkoxy group having from 1 to 10 carbon atoms.

8. The bis-o-nitrophenol derivative according to claim 7 , wherein said alkoxy group has at least one hydrogen atom substituted by a halogen.

9. The bis-o-nitrophenol derivative according to claim 7 , wherein said radical includes an oxygen atom bonding, to said phenyl groups carrying a nitro and at least one of said OR 2 groups, a substituent selected from the group consisting of a divalent heteroatom, a divalent heteroatomic group formed by a plurality of heteroatoms, a divalent silane group having a silicon with further valencies carrying an alkyl group having from 1 to 4 carbon atoms, a divalent siloxane group having from 2 to 5 silicon atoms and a silicon with free valencies carrying an alkyl group having from 1 to 4 carbon atoms.

10. The bis-o-nitrophenol derivative according to claim 9 , wherein, if said substituent is a divalent silane group, said alkyl group is straight-chained.

11. The bis-o-nitrophenol derivative according to claim 9 , wherein, if said substituent is a divalent silane group, said alkyl group is branched.

12. The bis-o-nitrophenol derivative according to claim 9 , wherein, if said substituent is a divalent siloxane group, said alkyl group is straight-chained.

13. The bis-o-nitrophenol derivative according to claim 9 , wherein, if said substituent is a divalent siloxane group, said alkyl group is branched.

14. A bis-o-nitrophenol derivative comprising a compound having a Formula Ia:

wherein:

R 2 is a substituent independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:

wherein R 3 , R 4 , and R 5 are selected from the group consisting of: —F, —(CH 2 ) n —CH 3 , —(CF 2 ) n —CF 3 , with n being an integer from 0 to 10, and wherein at least one of the radicals R 2 is a tert-butoxycarbonyl group of Formula II; and

Z is a connector selected from the group consisting of —O—, —CO—, —S—, —S—S—, —SO 2 —, —(CH 2 ) m —, —(CF 2 ) m —, —C(CR 6 ) 2 —, and any of the following structures:

wherein m is an integer from 1 to 10, and R 6 is independently selected from the group consisting of an alkyl radical with from 1 to 2 carbon atoms, hydrogen, halogen, and pseudo-halogen.

15. A bis-o-nitrophenol derivative comprising a structure selected from the group consisting of:

wherein:

R 1 and R 2 are substituents independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:

wherein R 3 , R 4 , and R 5 are selected from the group consisting of: —H, —F, —(CH 2 ) n —CH 3 , —(CF 2 ) n —CF 3 , with n being an integer from 0 to 10, provided that at least one of the radicals R 3 , R 4 , and R 5 is different than hydrogen, and wherein at least one of the radicals R 1 and R 2 is a tert-butoxycarbonyl group of Formula II.

16. A poly-o-hydroxyamide derived from a bis-o-nitrophenol derivative, wherein said bis-o-nitrophenol derivative comprises a compound selected from the group consisting of:

a compound having a general formula selected from the group consisting of Formula Ia and Formula Ib:

wherein:

R 1 and R 2 are substituents independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:

wherein R 3 , R 4 , and R 5 are selected from the group consisting of: —H, —F, —(CH 2 ) n —CH 3 , —(CF 2 ) n —CF 3 , with n being an integer from 0 to 10, provided that at least one of the radicals R 3 , R 4 , and R 5 is different than hydrogen, and wherein at least one of the radicals R 1 and R 2 is a tert-butoxycarbonyl group of Formula II; and

Z is a connector selected from the group consisting of a carbon-carbon single bond, a carbon-carbon bond common to both of said phenyl groups carrying said nitro and one of said OR 1 and said OR 2 group, a divalent alkyl radical with from 1 to 20 carbon atoms, a divalent aryl radical with from 6 to 20 carbon atoms, and a divalent aralkyl radical;

and

a compound having a general formula selected from the group consisting of Formula Ia and Formula Ib:

wherein:

R 1 and R 2 are substituents independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:

wherein R 3 , R 4 , and R 5 are selected from the group consisting of: —H, —F, —(CH 2 ) n —CH 3 , —(CF 2 ) n —CF 3 , with n being an integer from 0 to 10, provided that at least one of the radicals R 3 , R 4 , and R 5 is different than hydrogen, and wherein at least one of the radicals R 1 and R 2 is a tert-butoxycarbonyl group of Formula II; and

Z is a connector selected from the group consisting of —O—, —CO—, —S—, —S—S—, —SO 2 —, —(CH 2 ) m —, —(CF 2 ) m —, —C(CR 6 ) 2 —, and any of the following structures:

wherein m is an integer from 1 to 10, and R 6 is independently selected from the group consisting of an alkyl radical with from 1 to 2 carbon atoms, hydrogen, halogen, and pseudo-halogen.

17. A polybenzoxazole derived from a bis-o-nitrophenol derivative, wherein said bis-o-nitrophenol derivative includes a compound selected from the group consisting of:

a compound having a Formula Ia:

wherein:

R 2 is a substituent independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:

wherein R 3 , R 4 , and R 5 are selected from the group consisting of: —F, —(CH 2 ) n —CH 3 , —(CF 2 ) n —CF 3 , with n being an integer from 0 to 10, and wherein at least one of the radicals R 2 is a tert-butoxycarbonyl group of Formula II; and

Z is a connector selected from the group consisting of a carbon-carbon single bond, a carbon-carbon bond common to both of said phenyl groups carrying said nitro and one of said OR 2 groups, a divalent alkyl radical with from 1 to 20 carbon atoms, a divalent aryl radical with from 6 to 20 carbon atoms, and a divalent aralkyl radical;

and

a compound having a Formula Ia:

wherein:

R 2 is a substituent independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:

wherein R 3 , R 4 , and R 5 are selected from the group consisting of: —F, —(CH 2 ) n —CH 3 , —(CF 2 ) n —CF 3 , with n being an integer from 0 to 10, and wherein at least one of the radicals R 2 is a tert-butoxycarbonyl group of Formula II; and

Z is a connector selected from the group consisting of —O—, —CO—, —S—, —S—S—, —SO 2 —, —(CH 2 ) m —, —(CF 2 ) m —, —C(CR 6 ) 2 —, and any of the following structures:

wherein m is an integer from 1 to 10, and R 6 is independently selected from the group consisting of an alkyl radical with from 1 to 2 carbon atoms, hydrogen, halogen, and pseudo-halogen.

18. A material for a microelectronic device, based on a bis-o-nitrophenol derivative, the bis-o-nitrophenol derivative comprising a compound having a general formula selected from the group consisting of:

a compound having a Formula Ia:

wherein:

R 2 is a substituent independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:

wherein R 3 , R 4 , and R 5 are selected from the group consisting of: —F, —(CH 2 ) n —CH 3 , —(CF 2 ) n —CF 3 , with n being an integer from 0 to 10, and wherein at least one of the radicals R 2 is a tert-butoxycarbonyl group of Formula II; and

Z is a connector selected from the group consisting of a carbon-carbon single bond, a carbon-carbon bond common to both of said phenyl groups carrying said nitro and one of said OR 2 groups, a divalent alkyl radical with from 1 to 20 carbon atoms, a divalent aryl radical with from 6 to 20 carbon atoms, and a divalent aralkyl radical;

and

a compound having a Formula Ia:

wherein:

R 2 is a substituent independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:

wherein R 3 , R 4 , and R 5 are selected from the group consisting of: —F, —(CH 2 ) n —CH 3 , —(CF 2 ) n —CF 3 , with n being an integer from 0 to 10, and wherein at least one of the radicals R 2 is a tert-butoxycarbonyl group of Formula II; and

Z is a connector selected from the group consisting of —O—, —CO—, —S—, —S—S—, —SO 2 —, —(CH 2 ) m —, —(CF 2 ) m —, —C(CR 6 ) 2 —, and any of the following structures:

wherein m is an integer from 1 to 10, and R 6 is independently selected from the group consisting of an alkyl radical with from 1 to 2 carbon atoms, hydrogen, halogen, and pseudo-halogen.

19. A microelectronic assembly comprising:

a microelectronic device; and

a material coating said electronic device, said material including a bis-o-nitrophenol derivative, said bis-o-nitrophenol derivative including a compound having a general formula selected from the group consisting of:

a compound having a Formula Ia:

wherein:

R 2 is a substituent independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:

wherein R 3 , R 4 , and R 5 are selected from the group consisting of: —F, —(CH 2 ) n —CH 3 , —(CF 2 ) n —CF 3 , with n being an integer from 0 to 10, and wherein at least one of the radicals R 2 is a tert-butoxycarbonyl group of Formula II; and

Z is a connector selected from the group consisting of a carbon-carbon single bond, a carbon-carbon bond common to both of said phenyl groups carrying said nitro and one of said OR 2 groups, a divalent alkyl radical with from 1 to 20 carbon atoms, a divalent aryl radical with from 6 to 20 carbon atoms, and a divalent aralkyl radical;

and

a compound having a Formula Ia:

wherein:

R 2 is a substituent independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:

wherein R 3 , R 4 , and R 5 are selected from the group consisting of: —F, —(CH 2 ) n —CH 3 , —(CF 2 ) n —CF 3 , with n being an integer from 0 to 10, and wherein at least one of the radicals R 2 is a tert-butoxycarbonyl group of Formula II; and

Z is a connector selected from the group consisting of —O—, —CO—, —S—, —S—S—, —SO 2 —, —(CH 2 ) m —, —(CF 2 ) m —, —C(CR 6 ) 2 —, and any of the following structures:

wherein m is an integer from 1 to 10, and R 6 is independently selected from the group consisting of an alkyl radical with from 1 to 2 carbon atoms, hydrogen, halogen, and pseudo-halogen.