Resist composition containing specific cross-linking agent

Details Resist composition containing specific cross-linking agent Resist composition containing specific cross-linking agent

1998-06-22

2002-01-01

Ashton, Rosemary (Department: 1752)

Radiation imagery chemistry: process, composition, or product th

Imaging affecting physical property of radiation sensitive...

Radiation sensitive composition or product or process of making

C430S325000, C430S270100, C549S512000

Reexamination Certificate

active

06335143

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to a resist composition containing a specific cross-linking agent useful in the production of semiconductor devices, etc., a process for forming a pattern using the resist composition, and a cross-linking agent for a negative working resist material using ArF excimer laser beams.
Recently, with an increase of integration of semiconductor integrated circuits, the minimum pattern in the integrated circuits becomes submicron order and this tendency is further advancing to more minimized one. It is a photolithography technique that plays an important role in the formation of fine patterns in the production of semiconductor devices.
Generally speaking, a resolution degree R of a resist in a reduced projective method is shown by the equation of Rayleigh: R=k·&lgr;/NA (wherein &lgr; is a wavelength of light from an exposure source, NA is a numerical aperture of a lens, and k is a process constant). As is clear from this equation, it is understood that in advance of minimization, the resolution degree of a resist can be increased proportionally, when a more shortened wavelength of light from the exposure source is used. By applying this, at present, an ultra LSI has been produced by an exposure technique using i-line light (wavelength of 365 nm) and KrF excimer laser beams (wavelength of 248 nm) as an exposure source, and further an exposure technique using ArF excimer laser beams (wavelength of 193 nm) as an exposure source has been developed in order to comply with still further minimized processing.
In order to form a pattern of submicron order with the use of an exposure light having more shortened wavelength such as deep UV light and one belonging to an area of vacuum UV, a resist used is required to have excellent transmittance against the wavelength of the exposure light and further to have excellent dry etching resistance. However, so far known resist materials have such a defect in that they show high absorbance against ArF excimer laser beams and hardly transmit the laser beams because they contain an aromatic ring such as phenol in its molecule, resulting in failing to form a fine pattern.
Under such a situation, resist materials containing no aromatic ring, having high transmittance against ArF excimer laser beams and high dry etching resistance have been developed. For instance, it is reported in JP-A 9-73173 and JP-A 8-259626 that resist materials wherein methacrylic acid is used as a base resin and an alicyclic ring is introduced show high transmittance and high dry etching resistance and thus can form a fine pattern of 0.2 &mgr;m or less. However, all of these resist materials as mentioned above belong to positive type resist in which the part (or area) exposed to a light is dissolved in a developing solution.
On the other hand, a Levenson type phase shift method using a phase of light has been developed in i-line light lithography and KrF excimer laser lithography as an ultra resolution technique in compliance with minimization beyond the resolution limit of light. This technique is considered to be applied also to ArF excimer laser lithography. However, the Levenson type phase shift technique requires a negative type resist process because of a structure of a mask and cannot be applied to so far developed positive type resists.
Additionally, so far known negative type resists generally comprise as a matrix polymer a resin containing a benzene ring such as novolac resin and polyvinyl phenol and a triazine type compound as a cross-linking agent. Further, a resist using an epoxy group has been proposed as disclosed in Willard Conley, et al, Proc. SPIE, vol. 1262, 49 (1990). However, since a phenol resin is used as a matrix polymer, there is such a defect in that ArF excimer laser beams cannot be used because of its high absorbability to ArF excimer laser beams.
As mentioned above, a combination of the ArF excimer laser beams exposure technique with the Levenson type phase shift method seems to be very effective for the minimization, but there has been a problem in that no negative type resist applicable thereto has been developed yet and thus no negative type pattern can be formed.
SUMMARY OF THE INVENTION
Under such circumstances as mentioned above, the present invention has been accomplished to overcome the defects of prior art.
An object of the present invention is to provide a novel resist composition capable of giving a resist film which shows high transmittance of deep UV light having such a short wavelength as 220 nm or less and excellent etching resistance and thus can be applied to ArF excimer laser lithography using the Levenson type phase shift method, to provide a process for forming a pattern using this resist composition and to provide a novel cross-linking agent for an ArF negative type resist material.
The present invention provides a resist composition comprising
(a) an aliphatic alkali-soluble polymer,
(b) a compound represented by the following formula [1], [2] or [3],
(c) a photo-sensitive compound which generates an acid upon exposure to light, and
(d) a solvent capable of dissolving the- above components (a) to (c);
A
1
—T
1
—R
1
—T
2
—A
2
  [1]
wherein R
1
is a divalent aliphatic hydrocarbon residue which may contain at least one of —O—, —CO—, —COO— and —OCO—; A
1
and A
2
are independently an alkyl group containing one or more oxirane rings; and T
1
and T
2
are independently, —O—, —COO— or —OCO—,
wherein R
2
is a trivalent aliphatic hydrocarbon residue which may contain at least one of —O—, —CO—, —COO — and —OCO—; A
1
to A
3
are independently an alkyl group containing one or more oxirane rings; and T
1
to T
3
are independently, —O—, —COO— or —OCO—,
wherein R
3
is a tetravalent hydrocarbon residue which may contain at least one of —O—, —CO—, —COO— and —OCO—; A
1
to A
4
are independently an alkyl group containing one or more oxirane rings; and T
1
to T
4
are independently, —O—, —COO— or —OCO—.
The present invention also provides a process for forming a pattern, which comprises
a step of applying a resist composition described above to a substrate,
a step of subjecting the resulting substrate to heat treatment and then exposure to light having a wavelength of 220 nm or less through a mask, and
a step of developing the thus treated substrate using a developing solution, if necessary, after baking treatment.
The present invention further provides a cross-linking agent for an ArF negative working resist material, comprising a compound represented by the following formula [1], [2] or [3]:
A
1
—T
1
—R
1
—T
2
—A
2
  [1]
wherein R
1
, A
1
, A
2
, T
1
and T
2
are as defined above,
wherein R
2
, A
1
, A
2
, A
3
, T
1
, T
2
and T
3
are as defined above,
wherein R
3
, A
1
, A
2
, A
3
, A
4
, T
1
, T
2
, T
3
and T
4
are as defined above.
The present invention still further provides a compound represented by the formula:
wherein R
2
, A
1
, A
2
, A
3
, T
1
, T
2
and T
3
are as defined above, except for a case wherein R
2
is
each of T
1
to T
3
is —O—; and each of A
1
to A
3
is a glycidyl group.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The present inventors have made extensive study for realizing the above-mentioned objects to find that when the compound of the formula [1], [2] or [3] is used as a cross-linking agent, a resist composition showing high photo-transparency in a wavelength range of 220 nm or less and capable of forming a fine negative type pattern can be obtained, and have accomplished the present invention on the basis of this finding.
The resist composition of the present invention comprises
(a) an aliphatic alkali-soluble polymer,
(b) a compound represented by the formula:
A
1
—T
1
—R
1
—T
2
—A
2
  [1]
wherein R
1
is a divalent aliphatic hydrocarbon residue which may contain at least one of —O—, —CO—, —COO— and —OCO—; A
1
and A
2
are independently an alkyl group containing one or more oxirane rings; and T
1

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