Method of forming stack layer and method of manufacturing electronic device having the same

• US 20060275987A1
• Filed: 05/17/2006
• Published: 12/07/2006
• Est. Priority Date: 05/18/2005
• Status: Active Grant

• Current Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.), Samsung SDI Company Limited
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.), Samsung SDI Company Limited
• Inventors: Kim, Young-Hwan, Park, Shang-Hyeun, Lee, Hang-Woo
• Granted Patent: US 7,700,269 B2
• Time in Patent Office: Days
• US Class Current: 438/264
• CPC Class Codes: H01J 2329/00 Electron emission display panels, e.g. field emission display panels
• CPC Class Codes: H01J 9/025 of field emission cathodes

Abstract

A method of forming a stacked structure in an electronic device, where a photoresist for performing multi-patterning processes is used. Also, a method of manufacturing a FED in which different structures can be multi-patterned by using a single photoresist mask. The photoresist has a solubility to a solvent by heat-treatment after exposure, and a complicated structure can be formed using the photoresist.

Claims

1. A method of forming a stacked structure in an electronic material, comprising:

coating at least one target material layer on a substrate of the electronic material;

forming a mask layer by coating a positive photoresist having a polymer on the substrate, the polymer comprising at least 50 mole % of monomers having a structure selected from the group consisting of Formulae 1 to 3;

first baking the mask layer at a first temperature;

exposing the mask layer to light with a predetermined pattern;

second baking the mask layer at a second temperature;

developing the mask layer to form an etch window in the mask layer;

etching the target material layer through the etch window;

repeating at least twice the exposing to the developing; and

removing the mask layer;

where R₁ is hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, R₂ is an alkyl group having 1 to 6 linear or cyclic carbon atoms, and R₃ is hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms;

where R₁ is hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, R₂ is an alkyl group having 1 to 6 linear or cyclic carbon atoms, R₃ and R₄ are independently hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, and R₁ and R₂, or R₁ and either R₃ or R4, or R₂ and either R₃ or R₄ are joined to form

where R₁ is hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, R₂ is an alkyl group having 1 to 6 linear or cyclic carbon atoms, R₃ and R₄ are independently hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, and R₁ and R₂, or R₁ and either R₃ or R4, or R₂ and either R₃ or R₄ are joined to form a 5-, 6-, or 7-membered ring.

2. The method of claim 1, wherein the polymer in the photoresist is selected from the group consisting of 1-ehtoxyethyl methacrylate, 1-ehtoxyethyl acrylate, 1-butoxyethyl methacrylate, 1-butoxyethyl acrylate, 1-ethoxy-1-propyl methacrylate, 1-ethoxy-1-propyl acrylate, tetrahydropyranyl methacrylate, tetrahydropyranyl acrylate, tetrahydropyranyl p-vinylbenzoate, 1-ethoxy-1-propyl p-vinylbenzoate, 4-(2-tetrahydropyranyloxy)benzyl methacrylate, 4-(2-tetrahydropyranyloxy)benzyl acrylate, 4-(1-butoxyethoxy)benzyl methacrylate, 4-(1-butoxyethoxy)benzyl acrylate, t-butyl methacrylate, t-butyl acrylate, neopentyl methacrylate, neopentyl acrylate, 1-Bicyclo{2,2,2}octyl methacrylate (or acrylate) and their derivatives, 1-Bicyclo{2,2,1}heptyl methacrylate (or acrylate) and their derivatives, 1-Bicyclo{2,1,1}hexyl methacrylate (or acrylate) and their derivatives, 1-Bicyclo{1,1,1}pentyl methacrylate (or acrylate) and their derivatives, and 1-adamantyl methacrylate (or acrylate) and their derivatives.

3. The method of claim 1, wherein the photoresist further comprises 0.5 to 30 mole % of photoacid generator and 10 to 1,000 ppm of photosensitizer.

4. The method of claim 2, wherein the photoresist further comprises 0.5 to 30 mole % of photoacid generator and 10 to 1,000 ppm of photosensitizer.

5. The method of claim 1, wherein the second temperature is 100 to 130°

C.

6. A method of manufacturing a field emission device, comprising:

forming a stacked structure having a substrate, a cathode having a predetermined pattern on the substrate, a gate insulation layer on the cathode, and a gate electrode layer on the gate insulation layer;

forming a mask layer by coating a positive photoresist having a polymer on the stacked structure, the polymer comprising at least 50 mole % of monomers having a structure selected from the group consisting of Formulae 1 to 3;

first baking the mask layer at a first temperature range;

first exposing the mask layer to light with a first pattern;

second baking the mask layer at a second temperature range;

forming on the mask layer an etch window partially exposing the gate electrode by developing the mask layer;

forming a gate hole in the gate electrode layer by etching a portion of the gate electrode layer exposed by the etch window;

forming a throughhole in the gate electrode layer by etching a portion of the gate insulation layer;

second exposing to light a region including the etch window of the mask layer and having a greater size then the etch window of the mask layer, and baking the second-exposed region at the second temperature range to form an enlarged etch window;

enlarging the gate hole by etching a region adjacent to the gate hole in the gate electrode exposed by the second exposure; and

removing the mask layer;

where R₁ is hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, R₂ is a alkyl group having 1 to 6 linear or cyclic carbon atoms; and

R₃ is hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms;

where R₁ is hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, R₂ is an alkyl group having 1 to 6 linear or cyclic carbon atoms, R₃ and R₄ are independently hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, and R₁ and R₂, or R₁ and either R₃ or R4, or R₂ and either R₃ or R₄ are joined to form a 5-, 6-, or 7-membered ring; and

where R₁ is hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, R₂ is an alkyl group having 1 to 6 linear or cyclic carbon atoms, R₃ and R₄ are independently hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, and R_{1 and R2}, or R₁ and either R₃ or R4, or R₂ and either R₃ or R₄ are joined to form a 5-, 6-, or 7-membered ring.

7. The method of claim 6, wherein the polymer in the photoresist is selected from the group consisting of 1-ehtoxyethyl methacrylate, 1-ehtoxyethyl acrylate, 1-butoxyethyl methacrylate, 1-butoxyethyl acrylate, 1-ethoxy-1-propyl methacrylate, 1-ethoxy-1-propyl acrylate, tetrahydropyranyl methacrylate, tetrahydropyranyl acrylate, tetrahydropyranyl p-vinylbenzoate, 1-ethoxy-1-propyl p-vinylbenzoate, 4-(2-tetrahydropyranyloxy)benzyl methacrylate, 4-(2-tetrahydropyranyloxy)benzyl acrylate, 4-(1-butoxyethoxy)benzyl methacrylate, 4-(1-butoxyethoxy)benzyl acrylate, t-butyl methacrylate, t-butyl acrylate, neopentyl methacrylate, neopentyl acrylate, 1-Bicyclo{2,2,2}octyl methacrylate (or acrylate) and their derivatives, 1-Bicyclo{2,2,1}heptyl methacrylate (or acrylate) and their derivatives, 1-Bicyclo{2,1,1}hexyl methacrylate (or acrylate) and their derivatives, 1-Bicyclo{1,1,1}pentyl methacrylate (or acrylate) and their derivatives, and 1-adamantyl methacrylate (or acrylate) and their derivatives.

8. The method of claim 6, wherein the photoresist further comprises 0.5 to 30 mole % of photoacid generator and 10 to 1,000 ppm of photosensitizer.

9. The method of claim 7, wherein the photoresist further comprises 0.5 to 30 mole % of photoacid generator and 10 to 1,000 ppm of photosensitizer.

10. The method of claim 6, wherein the throughhole in the gate insulation layer and the gate hole in the gate electrode are respectively formed using different etchants.

11. The method of claim 9, wherein the second temperature range is from 100 to 130°

C.

12. The method of claim 6, further comprising forming an electron emitting material layer on the cathode exposed by the through hole.

13. A method of patterning layers of a stacked structure in an electronic device, the method comprising:

forming a photoresist mask layer on the stacked structure having the plural layers, the mask layer comprising a polymer comprising at least 50 mole % of monomers having a structure selected from the group consisting of Formulae 1 to 3;

baking the mask layer at a first temperature range;

exposing the mask layer with a first pattern;

baking the mask layer at a second temperature range;

forming on the mask layer an etch window partially exposing a first layer of the plural layers;

forming a first hole in the first layer by etching a portion of the first layer exposed by the etch window;

forming a second hole in a second layer formed below the first layer by etching a portion of the second layer;

exposing the mask layer to light with a second pattern;

baking the region exposed to the light with the second pattern at the second temperature range; and

removing the mask layer;

where R₁ is hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, and R₂ is a alkyl group having 1 to 6 linear or cyclic carbon atoms; and

R₃ is hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms;

where R₁ is hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, R₂ is an alkyl group having 1 to 6 linear or cyclic carbon atoms, R₃ and R₄ are independently hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, and R_{1 and R2}, or R₁ and either R₃ or R4, or R₂ and either R₃ or R₄ are joined to form a 5-, 6-, or 7-membered ring; and

where R₁ is hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, R₂ is an alkyl group having 1 to 6 linear or cyclic carbon atoms, R₃ and R₄ are independently hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, and R₁ and R₂, or R₁ and either R₃ or R4, or R₂ and either R₃ or R₄ are joined to form a 5-, 6-, or 7-membered ring.

14. The method of claim 13, wherein the polymer in the photoresist is selected from the group consisting of 1-ehtoxyethyl methacrylate, 1-ehtoxyethyl acrylate, 1-butoxyethyl methacrylate, 1-butoxyethyl acrylate, 1-ethoxy-1-propyl methacrylate, 1-ethoxy-1-propyl acrylate, tetrahydropyranyl methacrylate, tetrahydropyranyl acrylate, tetrahydropyranyl p-vinylbenzoate, 1-ethoxy-1-propyl p-vinylbenzoate, 4-(2-tetrahydropyranyloxy)benzyl methacrylate, 4-(2-tetrahydropyranyloxy)benzyl acrylate, 4-(1-butoxyethoxy)benzyl methacrylate, 4-(1-butoxyethoxy)benzyl acrylate, t-butyl methacrylate, t-butyl acrylate, neopentyl methacrylate, neopentyl acrylate, 1-Bicyclo{2,2,2}octyl methacrylate (or acrylate) and their derivatives, 1-Bicyclo{2,2,1}heptyl methacrylate (or acrylate) and their derivatives, 1-Bicyclo{2,1,1}hexyl methacrylate (or acrylate) and their derivatives, 1-Bicyclo{1,1,1}pentyl methacrylate (or acrylate) and their derivatives, and 1-adamantyl methacrylate (or acrylate) and their derivatives.

15. The method of claim 13, wherein the polymer has a molecular weight of 7,000 to 1,000,000.

16. The method of claim 13, wherein a source of the light is a laser radiation or a mercury lamp.

17. The method of claim 13, wherein the first temperature range is from 70 to 100°

C.

18. The method of claim 13, wherein the second temperature range is from 100 to 130°

C.

19. The method of claim 13, wherein the electronic device is a field emission device, the first layer is a gate electrode, and the second layer is a gate insulation layer.

20. A method of forming a photoresist mask layer for a multiple patterning of an electronic device, the method comprising;

preparing a composition having a polymer, the polymer comprising a monomer having a structure selected from the group consisting of Formulae 1 to 3;

where R₁ is hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, and R₂ is a alkyl group having 1 to 6 linear or cyclic carbon atoms; and

R₃ is hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms;

where R₁ is hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, R₂ is an alkyl group having 1 to 6 linear or cyclic carbon atoms, R₃ and R₄ are independently hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, and R₁ and R₂, or R₁ and either R₃ or R4, or R₂ and either R₃ or R₄ are joined to form a 5-, 6-, or 7-membered ring; and

where R₁ is hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, R₂ is an alkyl group having 1 to 6 linear or cyclic carbon atoms, R₃ and R₄ are independently hydrogen or an alkyl group having 1 to 6 linear or cyclic carbon atoms, and R₁ and R₂, or R₁ and either R₃ or R4, or R₂ and either R₃ or R₄ are joined to form a 5-, 6-, or 7-membered ring; and

applying the composition on the electronic device.