Coating compositions and methods of forming electronic devices
Coating compositions comprise: a B-staged reaction product of one or more compounds comprising: a core chosen from C 6-50 carbocyclic aromatic, C 2-50 heterocyclic aromatic, C 1-20 aliphatic, C 1-20 heteroaliphatic, C 3-20 cycloaliphatic, and C 2-20 heterocycloaliphatic, each of which may be substituted or unsubstituted; and two or more substituents of formula (1) attached to the core: wherein: Ar 1 is an aromatic group independently chosen from C 6-50 carbocyclic aromatic and C 2-50 heteroaromatic, each of which may be substituted or unsubstituted; Z is a substituent independently chosen from OR 1 , protected hydroxyl, carboxyl, protected carboxyl, SR 1 , protected thiol, —O—C(═O)—C 1-6 alkyl, halogen, and NHR 2 ; wherein each R 1 is independently chosen from H, C 1-10 alkyl, C 2-10 unsaturated hydrocarbyl, and C 5-30 aryl; each R 2 is independently chosen from H, C 1-10 alkyl, C 2-10 unsaturated hydrocarbyl, C 5-30 aryl, C(═O)—R 1 , and S(═O) 2 —R 1 ; x is an integer from 1 to the total number of available aromatic ring atoms in Ar 1 ; and * denotes the point of attachment to the core; provided that when the core comprises an aromatic ring, no substituents of formula (1) are in an ortho position to each other on the same aromatic ring of the core; and one or more solvents, wherein the total solvent content is from 50 to 99 wt % based on the coating composition. Coated substrates formed with the coating compositions and methods of forming electronic devices using the compositions are also provided. The compositions, coated substrates and methods find particular applicability in the manufacture of semiconductor devices.
1. A coating composition, comprising:
a B-staged reaction product of reactants consisting of one or more compounds comprising: a core chosen from C 6-50 carbocyclic aromatic, C 2-50 heterocyclic aromatic, C 1-20 aliphatic, C 1-20 heteroaliphatic, C 3-20 cycloaliphatic, and C 2-20 heterocycloaliphatic, each of which may be substituted or unsubstituted; and two or more substituents of formula (1) attached to the core:
wherein: Ar 1 is an aromatic group independently chosen from C 6-50 carbocyclic aromatic and C 2-50 heteroaromatic, each of which may be substituted or unsubstituted; Z is a substituent independently chosen from OR 1 , protected hydroxyl, carboxyl, protected carboxyl, SR 1 , protected thiol, —O—C(═O)—C 1-6 alkyl, halogen, and NHR 2 ; wherein each R 1 is independently chosen from H, C 1-10 alkyl, C 2-10 unsaturated hydrocarbyl, and C 5-30 aryl; each R 2 is independently chosen from H, C 1-10 alkyl, C 2-10 unsaturated hydrocarbyl, C 5-30 aryl, C(═O)—R 1 , and S(═O) 2 —R 1 ; x is an integer from 1 to the total number of available aromatic ring atoms in Ar 1 ; and * denotes the point of attachment to the core; provided that when the core comprises an aromatic ring, no substituents of formula (1) are in an ortho position to each other on the same aromatic ring of the core; and
one or more solvents, wherein the total solvent content is from 50 to 99 wt % based on the coating composition.
2. The coating composition of claim 1 , wherein the core is C 6-50 carbocyclic aromatic or C 2-50 heterocyclic aromatic, each of which may be substituted or unsubstituted, and from two to six substituents of formula (1) are attached to the core.
3. The coating composition of claim 1 , wherein each Z is independently chosen from OR 1 , protected hydroxyl, carboxyl, protected carboxyl, SH, —O—C(═O)—C 1-6 alkyl, and NHR 2 .
4. The coating composition of claim 3 , wherein each Z is hydroxyl.
5. The coating composition of claim 1 , wherein the core is chosen from pyridine, benzene, naphthalene, quinoline, isoquinoline, anthracene, phenanthrene, pyrene, coronene, triphenylene, chrysene, phenalene, benz[a]anthracene, dibenz[a,h]anthracene, and benzo[a]pyrene.
6. The coating composition of claim 1 , wherein each Ar 1 is independently chosen from pyridine, benzene, naphthalene, quinoline, isoquinoline, anthracene, phenanthrene, pyrene, coronene, triphenylene, chrysene, phenalene, benz[a]anthracene, dibenz[a,h]anthracene, and benzo[a]pyrene.
7. The coating composition of claim 1 , further comprising a curing agent, a surface leveling agent, or a flow additive.
8. The coating composition of claim 1 , further comprising a polymer or a crosslinker that is different from the B-staged reaction product.
9. The coating composition of claim 8 , wherein the polymer or the crosslinker comprises an epoxy group.
10. The coating composition of claim 1 , further comprising an epoxy-containing monomer.
11. A coated substrate, comprising:
an electronic device substrate; and
a layer formed from a coating composition of claim 1 on a surface of the electronic device substrate.
12. A method of forming an electronic device, comprising:
(a) providing an electronic device substrate;
(b) coating a layer of a coating composition of claim 1 on a surface of the electronic device substrate; and
(c) curing the layer of the curable compound to form a cured layer.
13. The method of claim 12 , wherein the cured layer is a photoresist underlayer, the method further comprising:
(d) forming a photoresist layer over the underlayer;
(e) patternwise exposing the photoresist layer to activating radiation;
(f) developing the exposed photoresist layer to form a pattern in the photoresist layer; and
(g) transferring the pattern to the underlayer.
14. The method of claim 13 , further comprising coating one or more of a silicon-containing layer, an organic antireflective coating layer, or a combination thereof over the underlayer before step (d).
15. The method of claim 14 , further comprising transferring the pattern to the one or more of the silicon-containing layer, the organic antireflective coating layer, or the combination thereof after step (f) and before step (g).
16. The method of claim 13 , further comprising:
(h) transferring the pattern to a layer of the electronic device substrate below the patterned underlayer; and
(i) removing the patterned underlayer.