Absorbing compounds for spin-on-glass anti-reflective...

Details Absorbing compounds for spin-on-glass anti-reflective... Absorbing compounds for spin-on-glass anti-reflective...

2000-07-17

2002-04-09

Dawson, Robert (Department: 1712)

Compositions: coating or plastic

Materials or ingredients

Pigment, filler, or aggregate compositions, e.g., stone,...

C556S458000, C556S442000, C528S034000, C528S043000, C528S039000, C430S272100, C525S477000

Reexamination Certificate

active

06368400

ABSTRACT:

TECHNICAL FIELD
The present invention relates generally to light-absorbing spin-on glass materials and more specifically to absorbing compounds that may be incorporated in spin-on glass materials for use as anti-reflective layers in photolithography and methods of producing the absorbing compounds.
BACKGROUND
To meet the requirements for faster performance, the characteristic dimensions of features of integrated circuit devices have continued to be decreased. Manufacturing of devices with smaller feature sizes introduces new challenges in many of the processes conventionally used in semiconductor fabrication. One of the most important of these fabrication processes is photolithography.
It has long been recognized that linewidth variations in patterns produced by photolithography can result from optical interference from light reflecting off an underlying layer on a semiconductor wafer. Variations in photoresist thickness due to the topography of the underlying layer also induce linewidth variations. Anti-reflective coatings (ARC) applied under a photoresist layer have been used to prevent interference from reflection of the irradiating beam. In addition, anti-reflective coatings partially planarize the wafer topography, helping to improve linewidth variation over steps because the photoresist thickness is more uniform.
Organic polymer films, particularly those that absorb at the i-line (365 nm) and g-line (436 nm) wavelengths conventionally used to expose photoresists, and at the recently used 248 nm wavelength, have been employed as anti-reflective coatings. However, the fact that the organic ARC's share many chemical properties with the organic photoresists can limit usable process sequences. Furthermore organic ARC's may intermix with photoresist layers. One solution to avoid intermixing, is to introduce thermosetting binders as additional components of organic ARC's, as described, for example in U.S. Pat. No. 5,693,691 to Flaim et al. Dyes may also be incorporated in organic ARC's, as well as, optionally, additional additives such as wetting agents, adhesions promoters, preservatives, and plasticizers, as described in U.S. Pat. No. 4,910,122 to Amold et al.
Silicon oxynitride is another material that has been used as an anti-reflective coating. However, silicon oxynitride works as an ARC by a destructive interference process rather than by absorption, which means that very tight control of the oxynitride thickness is necessary and that the material may not work well as an ARC over highly variable topography. Furthermore silicon oxynitride is typically deposited by chemical vapor deposition, while photoresist layers are typically applied using a spin-coater. The additional chemical vapor deposition process can add to processing complexity.
Yet another class of materials that can be used as an anti-reflective layer is spin-on-glass (SOG) compositions containing a dye. Yau et al., U.S. Pat. No. 4,587,138, disclose a dye such as basic yellow #11 mixed with a spin-on-glass in an amount approximately 1% by weight. Allman et al. U. S. Pat. No. 5,100,503 disclose a cross-linked polyorganosiloxane containing an inorganic dye such as TiO
2
, Cr
2
O
7
, MoO
4
, MnO
4
, or ScO
4
, and an adhesion promoter. Allman additionally teaches that the spin-on-glass compositions also serve as a planarizing layer. However, the spin-on-glass, dye combinations that have been disclosed to date are not optimal for exposure to the deep ultraviolet, particularly 248 and 193 nm, light sources that are coming into use to produce devices with small feature sizes. In addition, not all dyes can be readily incorporated into an arbitrary spin-on-glass composition.
Thus there remains a need for compounds absorbing strongly in the deep ultraviolet spectral region that may be incorporated into spin-on-glass compositions to provide anti-reflective coatings and for methods of synthesizing such absorbing compounds.
SUMMARY
An anti-reflective coating material for deep ultraviolet photolithography includes one or more organic absorbing compounds incorporated into a spin-on-glass (SOG) material. According to an embodiment of the present invention, an absorbing ether-like compound including a siliconethoxy, silicondiethoxy, or silicontriethoxy species attached to a naphthalene or anthracene chromophore via an oxygen linkage is used as an organic absorbing compound. The absorbing ether-like compounds have a general formula C
14
H
9
(CH
2
)
n
OSiR
m
(OC
2
H
5
)
3-m
or C
10
H
8
(CH
2
)
n
OSiRm(OC
2
H
5
)
3-m
, where n=1-3, m=0-2, and R is hydrogen, or an alkyl group such as a methyl, ethyl, or propyl group.
A method of synthesizing the light-absorbing ether-like compounds of the present invention is based on the reaction of an alcohol-substituted chromophore with an acetoxysilicon compound of the general formula R
m
Si(OCOCH
3
)
4-m
, in the presence of a stoichiometric amount of alcohol, where the reactants have the molar ratio of 1:1 :3-m. For example, the synthesis of 9-anthracene methoxy-methyldiethoxysilane uses 9-anthracene methanol, methyltriacetoxysilane (MTAS), and ethanol in a molar ratio of 1:1:2 as reactants. The reactants are combined with acetone, or a suitable alternative ketone, to form a reaction mixture which is stirred for an extended period sufficient to form the product, and then the acetic acid byproduct is removed by inert gas purging or by vacuum extraction.
The absorbing ether-like compounds may be incorporated into spin-on-glass materials including methylsiloxane, methylsilsesquioxane, phenylsiloxane, phenylsilsesquioxane, methylphenylsiloxane, methylphenylsilsesquioxane, and silicate polymers. As used herein, spin-on-glass materials also include hydrogensiloxane polymers of the general formula (H
0-1.0
SiO
1.5-2.0
)
x
and hydrogensilsesquioxane polymers, which have the formula (HSiO
1.5
)
x
, where x is greater than about 8. Also included are copolymers of hydrogensilsesquioxane and alkoxyhydridosiloxane or hydroxyhydridosiloxane. Spin-on-glass materials additionally include organohydridosiloxane polymers of the general formula (H
0-1.0
SiO
1.5-2.0
)
n
(R′
0-1.0
SiO
1.5-2.0
)
m
, and organohydridosilsesquioxane polymers of the general formula (HSiO
1.5
)
n
(R′SiO
1.5
)
m
, where m is greater than 0and the sum of n and m is greater than about 8 and R′ is alkyl or aryl. Coating solutions of spin-on-glass materials incorporating absorbing compounds are used to form anti-reflecting films on various layers in integrated circuit devices.
According to another aspect of the present invention, methods for synthesizing absorbing spin-on-glass compositions including the absorbing ether compounds are also provided.


REFERENCES:
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Andrews, et al., “Spinnable and UV-Patternable Hybrid Sol-Gel Silica Glass for Direct Semiconductor Dielectric Layer Manufacturing”, p. 347, SPIE 25th Annual Symposium on Microlithography, Feb. 27-Mar. 3, 2000.
Bauer, et al., “ARC technology to minimize CD-Variations during Emitter structuring—Experiment and Simulation”, p. 459, SPIE 25th Annual Symposium on Microlithography, Feb. 27-Mar. 3, 2000.
Chou, et al., “Anti-Reflection Strategies for Sub-0.18 &mgr;m Dual Damascene Patterning in KrF 248nm Lithography”, p. 453, SPIE 25th Annual Symposium on Microlithography, Feb. 27-Mar. 3, 2000.
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