Aromatic underlayer
Compounds having three or more alkynyl moieties substituted with an aromatic moiety having one or more of certain substituents are useful in forming underlayers useful in semiconductor manufacturing processes.
1. A method comprising: (a) providing an electronic device substrate; (b) coating a layer of a coating composition comprising one or more curable compounds on a surface of the electronic device substrate, wherein the one or more curable compounds comprise an aromatic core chosen from a C 5-6 aromatic ring and a C 9-30 fused aromatic ring system and three or more substituents of formula (1)
wherein at least two substituents of formula (1) are attached to the aromatic core; and wherein Ar 1 is an aromatic ring or fused aromatic ring system having from 5 to 30 carbons; Z is a substituent chosen from OR 1 , protected hydroxyl, carboxyl, protected carboxyl, SR 1 , protected thiol, —O—C(═O)—C 1-6 -alkyl, halogen, and NHR 2 ; each R 1 is chosen from H, C 1-10 alkyl, C 2-10 unsaturated hydrocarbyl, and C 5-30 aryl; each R 2 is 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 4; and * denotes the point of attachment to the aromatic core or the point of attachment to the curable compound other than to the aromatic core; wherein Ar 1 is not further substituted beyond the Z substituent(s) and the alkyne-containing substituent; (c) curing the layer of the curable compound to form an underlayer; (d) coating a layer of a photoresist on the underlayer; (e) exposing the photoresist layer to actinic radiation through a mask; (f) developing the exposed photoresist layer to form a resist pattern; and (g) transferring the pattern to the underlayer to expose portions of the electronic device substrate.
2. The method of claim 1 further comprising the steps of patterning the substrate; and then removing the patterned underlayer.
3. The method of claim 1 further comprising the step of coating one or more of a silicon-containing layer, an organic antireflective coating layer and a combination thereof over the underlayer before step (d).
4. The method of claim 3 further comprising the step of transferring the pattern to the one or more of the silicon-containing layer, the organic antireflective coating layer and the combination thereof after step (f) and before step (g).
5. The method of claim 1 wherein each Z is independently chosen from OR 1 , protected hydroxyl, carboxyl, protected carboxyl, SH, fluorine and NHR 2 .
6. The method of claim 1 wherein aromatic 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.
7. The method 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.
8. The method of claim 1 wherein the coating composition further comprises one or more of an organic solvent, a curing agent, and a surface leveling agent.
9. The method of claim 1 , wherein three substituents of formula (1) are attached to the aromatic core.
10. The method of claim 9 , wherein the aromatic core is a C6 aromatic ring and Z is —OH.
11. The method of claim 1 , wherein Z is —OH.
12. A method comprising: (a) providing an electronic device substrate; (b) coating a layer of a coating composition comprising one or more curable compounds of formula (2)
wherein Ar c is an aromatic core having from 5 to 30 carbon atoms; Ar 1 , Ar 2 , and Ar 3 are each independently an aromatic ring or fused aromatic ring system having from 5 to 30 carbons; Y is a single covalent chemical bond, a divalent linking group, or a trivalent linking group; Z 1 and Z 2 are independently a substituent chosen from OR 1 , protected hydroxyl, carboxyl, protected carboxyl, SR 1 , protected thiol, —O—C(═O)—C 1-6 -alkyl, halogen, and NHR 2 ; each R 1 is chosen from H, C 1-10 alkyl, C 2-10 unsaturated hydrocarbyl, and C 5-30 aryl; each R 2 is 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 ; x1=1 to 4; x2=1 to 4; y1=2 to 4; each y2=0 to 4; y1+each y2≥3; w=0 to 2; and z equals 0 to 2; wherein z=1 when Y is a single covalent chemical bond or a divalent linking group; and z=2 when Y is a trivalent linking group on a surface of the electronic device substrate; wherein each Ar 1 is not further substituted beyond the Z 1 substituent(s) and the respective alkyne-containing substituent, and each Ar 3 is not further substituted beyond the Z 2 substituent(s) and the respective alkyne-containing substituent; (c) curing the layer of the curable compound to form an underlayer; (d) coating a layer of a photoresist on the underlayer; (e) exposing the photoresist layer to actinic radiation through a mask; (f) developing the exposed photoresist layer to form a resist pattern; and (g) transferring the pattern to the underlayer to expose portions of the electronic device substrate.
13. The method of claim 12 , wherein Z 1 and Z 2 are —OH.