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US 7,125,814 B2Granted
Bis-o-nitrophenols derivatives and poly-o-hydroxyamides, polybenzoxazoles, materials, and microelectronic devices made therefrom
AssigneeInfineon Technologies AG
InventorRecai Sezi
Life of this patent
Estimating the term…
Abstract
Materials for dielectrics and/or buffer layers in microelectronics utilize polymers can be based on bis-o-nitrophenols. The bis-o-nitrophenols carry a tert-butoxycarbonyl group on at least one of the hydroxyl groups. The polybenzoxazoles prepared from these compounds have a lower dielectric constant than corresponding polymers which are prepared from bis-o-nitrophenols that do not have a tert-butoxycarbonyl group.
Claims19
A bis-o-nitrophenol derivative comprising a compound having a Formula Ia:
- wherein:
- R2 is a substituent independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:
- wherein R3, R4, and R5 are selected from the group consisting of:
- —F, —(CH2)n—CH3, —(CF2)n—CF3, with n being an integer from 0 to 10, and wherein at least one of the radicals R2 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 OR2 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.
3 more elements
A bis-o-nitrophenol derivative comprising a compound having a Formula Ia:
- wherein:
- R2 is a substituent independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:
- wherein R3, R4, and R5 are selected from the group consisting of:
- —F, —(CH2)n—CH3, —(CF2)n—CF3, with n being an integer from 0 to 10, and wherein at least one of the radicals R2 is a tert-butoxycarbonyl group of Formula II;
- and
- Z is a connector selected from the group consisting of —O—, —CO—, —S—, —S—S—, —SO2—, —(CH2)m—, —(CF2)m—, —C(CR6)2—, and any of the following structures:
- wherein m is an integer from 1 to 10, and R6 is independently selected from the group consisting of an alkyl radical with from 1 to 2 carbon atoms, hydrogen, halogen, and pseudo-halogen.
4 more elements
A bis-o-nitrophenol derivative comprising a structure selected from the group consisting of:
- wherein:
- R1 and R2 are substituents independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:
- wherein R3, R4, and R5 are selected from the group consisting of:
- —H, —F, —(CH2)n—CH3, —(CF2)n—CF3, with n being an integer from 0 to 10, provided that at least one of the radicals R3, R4, and R5 is different than hydrogen, and wherein at least one of the radicals R1 and R2 is a tert-butoxycarbonyl group of Formula II.
1 more element
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:
- R1 and R2 are substituents independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:
- wherein R3, R4, and R5 are selected from the group consisting of:
- —H, —F, —(CH2)n—CH3, —(CF2)n—CF3, with n being an integer from 0 to 10, provided that at least one of the radicals R3, R4, and R5 is different than hydrogen, and wherein at least one of the radicals R1 and R2 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 OR1 and said OR2 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:
- R1 and R2 are substituents independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:
- wherein R3, R4, and R5 are selected from the group consisting of:
- —H, —F, —(CH2)n—CH3, —(CF2)n—CF3, with n being an integer from 0 to 10, provided that at least one of the radicals R3, R4, and R5 is different than hydrogen, and wherein at least one of the radicals R1 and R2 is a tert-butoxycarbonyl group of Formula II;
- and
- Z is a connector selected from the group consisting of —O—, —CO—, —S—, —S—S—, —SO2—, —(CH2)m—, —(CF2)m—, —C(CR6)2—, and any of the following structures:
- wherein m is an integer from 1 to 10, and R6 is independently selected from the group consisting of an alkyl radical with from 1 to 2 carbon atoms, hydrogen, halogen, and pseudo-halogen.
13 more elements
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:
- R2 is a substituent independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:
- wherein R3, R4, and R5 are selected from the group consisting of:
- —F, —(CH2)n—CH3, —(CF2)n—CF3, with n being an integer from 0 to 10, and wherein at least one of the radicals R2 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 OR2 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:
- R2 is a substituent independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:
- wherein R3, R4, and R5 are selected from the group consisting of:
- —F, —(CH2)n—CH3, —(CF2)n—CF3, with n being an integer from 0 to 10, and wherein at least one of the radicals R2 is a tert-butoxycarbonyl group of Formula II;
- and
- Z is a connector selected from the group consisting of —O—, —CO—, —S—, —S—S—, —SO2—, —(CH2)m—, —(CF2)m—, —C(CR6)2—, and any of the following structures:
- wherein m is an integer from 1 to 10, and R6 is independently selected from the group consisting of an alkyl radical with from 1 to 2 carbon atoms, hydrogen, halogen, and pseudo-halogen.
13 more elements
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:
- R2 is a substituent independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:
- wherein R3, R4, and R5 are selected from the group consisting of:
- —F, —(CH2)n—CH3, —(CF2)n—CF3, with n being an integer from 0 to 10, and wherein at least one of the radicals R2 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 OR2 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:
- R2 is a substituent independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:
- wherein R3, R4, and R5 are selected from the group consisting of:
- —F, —(CH2)n—CH3, —(CF2)n—CF3, with n being an integer from 0 to 10, and wherein at least one of the radicals R2 is a tert-butoxycarbonyl group of Formula II;
- and
- Z is a connector selected from the group consisting of —O—, —CO—, —S—, —S—S—, —SO2—, —(CH2)m—, —(CF2)m—, —C(CR6)2—, and any of the following structures:
- wherein m is an integer from 1 to 10, and R6 is independently selected from the group consisting of an alkyl radical with from 1 to 2 carbon atoms, hydrogen, halogen, and pseudo-halogen.
13 more elements
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:
- R2 is a substituent independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:
- wherein R3, R4, and R5 are selected from the group consisting of:
- —F, —(CH2)n—CH3, —(CF2)n—CF3, with n being an integer from 0 to 10, and wherein at least one of the radicals R2 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 OR2 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:
- R2 is a substituent independently selected from the group consisting of a hydrogen atom and a tert-butoxycarbonyl group of formula II:
- wherein R3, R4, and R5 are selected from the group consisting of:
- —F, —(CH2)n—CH3, —(CF2)n—CF3, with n being an integer from 0 to 10, and wherein at least one of the radicals R2 is a tert-butoxycarbonyl group of Formula II;
- and
- Z is a connector selected from the group consisting of —O—, —CO—, —S—, —S—S—, —SO2—, —(CH2)m—, —(CF2)m—, —C(CR6)2—, and any of the following structures:
- wherein m is an integer from 1 to 10, and R6 is independently selected from the group consisting of an alkyl radical with from 1 to 2 carbon atoms, hydrogen, halogen, and pseudo-halogen.
16 more elements
Dependencies are inferred from the claim text.