KR20190088876A - protected coating material for dicing process - Google Patents

Abstract

The present invention relates to a protective coating agent for a dicing process for producing a semiconductor and, more specifically, to a protective coating agent for a dicing process which is coated on a surface of a wafer or the like to protect the surface of the wafer during a producing process.

Description

[0001] The present invention relates to a protective coating material for a dicing process,

The present invention relates to a protective coating for a dicing process for making a semiconductor, and more particularly, to a protective coating for a dicing process which is coated on the surface of a wafer or the like to protect the surface of the wafer during the manufacturing process.

In the semiconductor wafer processing process, the dicing process is also referred to as sawing, and is a process of separating the wafer into individual chip units between the wafer manufacturing process and the packaging process in the semiconductor production process.

At this time, as the individual chips of the semiconductor wafer are separated using the blades, fragments are scattered on the surface of the chip, causing defects. In order to solve these problems, a nozzle was installed on both sides of the blade and the horizontal direction of the wafer, and a large amount of water was sprayed at a high pressure to immediately remove the pieces falling on the chip surface. This method is useful when the size of the semiconductor chip is large and the processing time is short and the amount of the chips is small. However, since the chip size becomes smaller and the processing time becomes longer and the amount of the generated chips increases, .

Accordingly, in order to overcome the above-mentioned problems, Korean Patent Application No. 10-2009-0066314 discloses a nonionic surface active agent such as polyethylene oxide / polypropylene oxide (PEO-PPO), polyethylene glycol (PEG) It is disclosed that a cleaning liquid composition is prepared using an additive.

However, the above-mentioned composition can remove fragments of a certain size when sawing, but it is impossible to completely remove fine fragments. As a result, defects such as scratches and scratches are still not resolved by the minute fragments remaining.

Therefore, there is a need for a protective coating for dicing that can form a coating layer on the surface of such a wafer and can fundamentally block defects such as scratches, stains, smears, whitening, or corrosion that occur during a cutting process and other processing steps.

It is an object of the present invention to provide a protective coating for a dicing process which can protect a surface during processing of a wafer or the like during a semiconductor manufacturing process to prevent surface damage due to foreign matter inflow or the like .

In order to solve the above-mentioned problems, the protective coating composition for a dicing process of the present invention comprises a compound represented by the following formula (1) and a compound represented by the following formula (2).

[Chemical Formula 1]

또는

이고, R₀은

,

또는

이고, R₉, R₁₀, R₁₁ 및 R₃₂은 각각 독립적으로 C1 ~ C10의 알킬기이며, R₁₂는 C1 ~ C10의 알킬렌기이고, R₁은

,

또는

이고, R₂, R₃, R₄, R₅, R₆, R₇ 및 R₈은 각각 독립적으로 C1 ~ C15의 알킬렌기이며, n, m, l은 각각 독립적으로 1 ~ 50인 유리수이고, R₂₀은 C1 ~ C10의 알킬렌기,

또는

이며, R₂₇, R₂₈, R₂₉, R₃₀ 및 R₃₁은 각각 독립적으로 C1 ~ C10의 알킬렌기이고, R₂₁, R₂₂ 및 R₂₃은 각각 독립적으로 C1 ~ C10의 알킬기이며, R₁₆은 C1 ~ C10의 알킬기이고,Wherein R ₁₃ and R ₁₄ are each independently a C 1 to C 10 alkylene group, R ₁₅ is a C 1 to C 10 alkyl group, and R ₂₄ and R ₂₅ are each independently

or

And R < ₀ >

,

or

, R ₉ , R ₁₀ , R ₁₁ and R ₃₂ are each independently a C 1 to C 10 alkyl group, R ₁₂ is a C 1 to C 10 alkylene group, R ₁ is

,

or

And n, m and l are each independently a rational number of 1 to 50, and R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ are each independently a C 1 to C 15 alkylene group, R < ₂₀ > is a C1-C10 alkylene group,

or

_{And, R 27, R 28, R} 29, R 30 and R ₃₁ are each independently a C1 ~ C10 alkylene group, R _21, R ₂₂ and R ₂₃ is an alkyl group of C1 ~ C10, each independently, R ₁₆ is A C1 to C10 alkyl group,

(2)

In Formula 2, R ₁₇ , R _18, and R ₁₉ are each independently hydrogen, an aryl group, or a C 1 to C 10 alkyl group.

일 수 있다.In a preferred embodiment of the present invention, R ₂₄ and R ₂₅ of the compound represented by the formula (1)

Lt; / RTI >

이고, R₂₅는

일 수 있다.In one preferred embodiment of the present invention, R ₂₄ of the compound represented by Formula 1 is

And R < ₂₅ >

Lt; / RTI >

In one preferred embodiment of the present invention, the protective coating composition of the present invention may further comprise at least one of a polar organic solvent, a surface modifying additive, a flow control agent, and an adhesion promoter.

The protective coating for the dicing process of the present invention may include a compound represented by the following formula (10).

[Chemical formula 10]

또는

이며, R₀은

,

또는

이고, R₉, R₁₀, R₁₁ 및 R₃₂은 각각 독립적으로 수소 또는 C1 ~ C10의 알킬기이고, R₁₂는 C1 ~ C10의 알킬렌기이며, R₁은

,

또는

이고, R₂, R₃, R₄, R₅, R₆, R₇ 및 R₈은 각각 독립적으로 C1 ~ C15의 알킬렌기이며, n, m, l은 각각 독립적으로 1 ~ 50인 유리수이고, R₁₆은 C1 ~ C10의 알킬기이며, R₂₀은 C1 ~ C10의 알킬렌기,

또는

이고, R₂₇, R₂₈, R₂₉, R₃₀ 및 R₃₁은 각각 독립적으로 C1 ~ C10의 알킬렌기이며, R₂₁, R₂₂ 및 R₂₃은 각각 독립적으로 C1 ~ C10의 알킬기이며, A⁺는

이고, R₁₇, R₁₈ 및 R₁₉는 각각 독립적으로 수소, 아릴기 또는 C1 ~ C10의 알킬기이다.In the formula (10), R ₁₃ and R ₁₄ are each independently a C 1 to C 10 alkylene group, R ₁₅ is a C 1 to C 10 alkyl group, R ₂₄ and R ₂₅ each independently

or

And R < ₀ >

,

or

R ₉ , R ₁₀ , R ₁₁ and R ₃₂ are each independently hydrogen or a C 1 to C 10 alkyl group, R ₁₂ is a C 1 to C 10 alkylene group, R ₁ is

,

or

And n, m and l are each independently a rational number of 1 to 50, and R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ are each independently a C 1 to C 15 alkylene group, R ₁₆ is an alkyl group of C1 ~ C10, R ₂₀ is an alkylene group of C1 ~ C10,

or

_{And, R 27, R 28, R} 29, R 30 and R ₃₁ are each independently an alkylene group of _{C1 ~ C10, R 21, R} 22 and R ₂₃ is an alkyl group of C1 ~ C10, each independently, A ⁺ is

, R ₁₇ , R ₁₈ and R ₁₉ are each independently hydrogen, an aryl group or a C 1 to C 10 alkyl group.

일 수 있다.In one preferred embodiment of the present invention, R < ₂₄ > and R < _{25 &}

Lt; / RTI >

이고, R₂₅는

일 수 있다.In one preferred embodiment of the present invention, R ₂₄ of the compound represented by Formula 10 is

And R < ₂₅ >

Lt; / RTI >

In one preferred embodiment of the present invention, the protective coating of the present invention comprises 8 to 500 parts by weight of a polar organic solvent, 0.08 to 100 parts by weight of a surface modifying additive, 0.4 to 10 parts by weight of a flow control agent, 200 parts by weight and an adhesion promoter of 0.32 to 250 parts by weight.

Further, the process for preparing a protective coating for dicing according to the present invention comprises mixing and polymerizing a compound represented by the following formula (7), a compound represented by the following formula (8), a compound represented by the following formula (9) A second step of preparing a second polymer or a third polymer by mixing and reacting the produced first polymer with at least one compound represented by the following formula (6) and a compound represented by the following formula (4) And a third step of preparing a compound represented by the following general formula (10) by mixing and reacting the produced second polymer or the third polymer with a compound represented by the following general formula (2) and water.

(7)

,

또는

이고, R₂, R₃, R₄, R₅, R₆, R₇ 및 R₈은 각각 독립적으로 C1 ~ C15의 알킬렌기이며, n, m, l은 각각 독립적으로 1 ~ 50인 유리수이고, In Formula 7, R ₁ is

,

or

And n, m and l are each independently a rational number of 1 to 50, and R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ are each independently a C 1 to C 15 alkylene group,

[Chemical Formula 8]

,

또는

이고, R₉, R₁₀, R₁₁ 및 R₃₂은 각각 독립적으로 수소 또는 C1 ~ C10의 알킬기이며, R₁₂는 C1 ~ C10의 알킬렌기이고, In Formula 8, R < ₀ >

,

or

, R ₉ , R ₁₀ , R ₁₁ and R ₃₂ are each independently hydrogen or a C 1 to C 10 alkyl group, R ₁₂ is a C 1 to C 10 alkylene group,

[Chemical Formula 9]

In the general formula (9), R ₁₃ and R ₁₄ are each independently a C 1 to C 10 alkylene group, R ₁₅ is a C 1 to C 10 alkyl group,

[Chemical Formula 6]

또는

이고, R₂₇, R₂₈, R₂₉, R₃₀ 및 R₃₁은 각각 독립적으로 C1 ~ C10의 알킬렌기이며, R₂₁, R₂₂ 및 R₂₃은 각각 독립적으로 C1 ~ C10의 알킬기이고,In the formula (6), R ₂₀ represents an alkylene group having 1 to 10 carbon atoms,

or

, R ₂₇ , R ₂₈ , R ₂₉ , R ₃₀ and R ₃₁ are each independently a C 1 to C 10 alkylene group, R ₂₁ , R ₂₂ and R ₂₃ are each independently a C 1 to C 10 alkyl group,

[Chemical Formula 4]

In Formula 4, R ₁₆ is a C 1 to C 10 alkyl group,

(2)

In Formula 2, R ₁₇ , R ₁₈ and R ₁₉ are each independently hydrogen, an aryl group or a C 1 to C 10 alkyl group,

[Chemical formula 10]

또는

이며, R₀은

,

또는

이고, R₉, R₁₀, R₁₁ 및 R₃₂은 각각 독립적으로 수소 또는 C1 ~ C10의 알킬기이고, R₁₂는 C1 ~ C10의 알킬렌기이며, R₁은

,

또는

이고, R₂, R₃, R₄, R₅, R₆, R₇ 및 R₈은 각각 독립적으로 C1 ~ C15의 알킬렌기이며, n, m, l은 각각 독립적으로 1 ~ 50인 유리수이고, R₁₆은 C1 ~ C10의 알킬기이며, R₂₀은 C1 ~ C10의 알킬렌기,

또는

이고, R₂₇, R₂₈, R₂₉, R₃₀ 및 R₃₁은 각각 독립적으로 C1 ~ C10의 알킬렌기이며, R₂₁, R₂₂ 및 R₂₃은 각각 독립적으로 C1 ~ C10의 알킬기이며, A⁺는

이고, R₁₇, R₁₈ 및 R₁₉는 각각 독립적으로 수소, 아릴기 또는 C1 ~ C10의 알킬기이다.In the formula (10), R ₁₃ and R ₁₄ are each independently a C 1 to C 10 alkylene group, R ₁₅ is a C 1 to C 10 alkyl group, R ₂₄ and R ₂₅ each independently

or

And R < ₀ >

,

or

R ₉ , R ₁₀ , R ₁₁ and R ₃₂ are each independently hydrogen or a C 1 to C 10 alkyl group, R ₁₂ is a C 1 to C 10 alkylene group, R ₁ is

,

or

And n, m and l are each independently a rational number of 1 to 50, and R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ are each independently a C 1 to C 15 alkylene group, R ₁₆ is an alkyl group of C1 ~ C10, R ₂₀ is an alkylene group of C1 ~ C10,

or

_{And, R 27, R 28, R} 29, R 30 and R ₃₁ are each independently an alkylene group of _{C1 ~ C10, R 21, R} 22 and R ₂₃ is an alkyl group of C1 ~ C10, each independently, A ⁺ is

, R ₁₇ , R ₁₈ and R ₁₉ are each independently hydrogen, an aryl group or a C 1 to C 10 alkyl group.

In a preferred embodiment of the present invention, the second step is a step of mixing and reacting a compound represented by the following formula (4) with the produced first polymer to prepare a second polymer, and the third step is a step of mixing The compound represented by the formula (2) and water may be mixed and reacted to prepare a compound represented by the following formula (10).

[Chemical formula 10]

이고, R₀은

,

또는

이고, R₉, R₁₀, R₁₁ 및 R₃₂은 각각 독립적으로 C1 ~ C10의 알킬기이고, R₁₂는 C1 ~ C10의 알킬렌기이며, R₁은

,

또는

이고, R₂, R₃, R₄, R₅, R₆, R₇ 및 R₈은 각각 독립적으로 C1 ~ C15의 알킬렌기이며, n, m, l은 각각 독립적으로 1 ~ 50인 유리수이고, R₁₆은 C1 ~ C10의 알킬기이며, A⁺는

이고, R₁₇, R₁₈ 및 R₁₉는 각각 독립적으로 수소, 아릴기 또는 C1 ~ C10의 알킬기이다.In the formula (10), R ₁₃ and R ₁₄ are each independently a C 1 to C 10 alkylene group, R ₁₅ is a C 1 to C 10 alkyl group, and R ₂₄ and R ₂₅ are

And R < ₀ >

,

or

_{And, R 9, R 10, R} 11 and R ₃₂ is an alkyl group of C1 ~ C10, each independently, R ₁₂ is an alkylene group of C1 ~ C10, R ₁ is

,

or

And n, m and l are each independently a rational number of 1 to 50, and R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ are each independently a C 1 to C 15 alkylene group, R ₁₆ is an alkyl group of C1 ~ C10, a ⁺ is

, R ₁₇ , R ₁₈ and R ₁₉ are each independently hydrogen, an aryl group or a C 1 to C 10 alkyl group.

In a preferred embodiment of the present invention, the second step is a step 2-1 in which a compound represented by the formula (6) is mixed and reacted with the produced first polymer to prepare a third intermediate polymer, And a second step (2-2) of mixing and reacting the compound represented by the formula (4) with the polymer to prepare a third polymer, wherein the third step is a step of mixing the compound represented by the formula (2) And the compound represented by the following general formula (10) can be prepared.

[Chemical formula 10]

이고, R₂₅는

이며, R₀은

,

또는

이고, R₉, R₁₀, R₁₁ 및 R₃₂은 각각 독립적으로 C1 ~ C10의 알킬기이고, R₁₂는 C1 ~ C10의 알킬렌기이며, R₁은

,

또는

이고, R₂, R₃, R₄, R₅, R₆, R₇ 및 R₈은 각각 독립적으로 C1 ~ C15의 알킬렌기이며, n, m, l은 각각 독립적으로 1 ~ 50인 유리수이고, R₁₆은 C1 ~ C10의 알킬기이며, R₂₀은 C1 ~ C10의 알킬렌기,

또는

이고, R₂₇, R₂₈, R₂₉, R₃₀ 및 R₃₁은 각각 독립적으로 C1 ~ C10의 알킬렌기이며, R₂₁, R₂₂ 및 R₂₃은 각각 독립적으로 C1 ~ C10의 알킬기이고, A⁺는

이고, R₁₇, R₁₈ 및 R₁₉는 각각 독립적으로 수소, 아릴기 또는 C1 ~ C10의 알킬기이다.In the formula (10), R ₁₃ and R ₁₄ are each independently a C 1 to C 10 alkylene group, R ₁₅ is a C 1 to C 10 alkyl group, and R ₂₄ is

And R < ₂₅ >

And R < ₀ >

,

or

_{And, R 9, R 10, R} 11 and R ₃₂ is an alkyl group of C1 ~ C10, each independently, R ₁₂ is an alkylene group of C1 ~ C10, R ₁ is

,

or

And n, m and l are each independently a rational number of 1 to 50, and R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ are each independently a C 1 to C 15 alkylene group, R ₁₆ is an alkyl group of C1 ~ C10, R ₂₀ is an alkylene group of C1 ~ C10,

or

_{And, R 27, R 28, R} 29, R 30 and R ₃₁ are each independently an alkylene group of _{C1 ~ C10, R 21, R} 22 and R ₂₃ is an alkyl group of C1 ~ C10, each independently, A ⁺ is

, R ₁₇ , R ₁₈ and R ₁₉ are each independently hydrogen, an aryl group or a C 1 to C 10 alkyl group.

In one preferred embodiment of the present invention, the protective coating is prepared by mixing 101 to 153 parts by weight of the compound represented by the general formula (8), 11 to 18 parts by weight of the compound represented by the general formula (9) with respect to 100 parts by weight of the compound represented by the general formula 29 to 45 parts by weight of the compound represented by the general formula (4), 8 to 13 parts by weight of the compound represented by the general formula (2), and 33 to 51 parts by weight of the compound represented by the general formula (6).

에서 표시된 * 표시는 화학식 7의 -OH와 연결되는 부분이다.On the other hand, according to present the compound of the present invention, means a * in the chemical binding sites, it is described a compound represented by the above formula (7) as an example, to configure the R ₁

Is a moiety linked to -OH in formula (7).

The protective coating for the dicing process of the present invention has an effect to fundamentally prevent the damage occurring on the surface of the wafer or the contamination due to the foreign substance during the processing including the cutting process of the wafer during the semiconductor manufacturing process.

Also, it has physical properties to be cured by heat or ultraviolet rays (UV), and is not affected by heat or ultraviolet rays after curing, and includes water resistance and hardness. Therefore, The surface damage can be prevented, and after the manufacturing process is completed, it can be easily removed by the alkali solution.

Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings, which will be readily apparent to those skilled in the art to which the present invention pertains. The present invention may be embodied in many different forms and is not limited to the embodiments described herein. In order to clearly illustrate the present invention, parts not related to the description are omitted, and the same reference numerals are assigned to the same or similar components throughout the specification.

The protective coating composition for a dicing process of the present invention may include a compound represented by the following formula (1) and a compound represented by the following formula (2).

[Chemical Formula 1]

In the above Formula 1, R ₁₃ and R ₁₄ each independently may be an alkylene group of C1 ~ C10, preferably may be an alkylene group of C1 ~ C5.

In the above formula (1), R ₁₅ may be a C1-C10 alkyl group, preferably a C1-C5 alkyl group.

또는

일 수 있다.In the above formula (1), R ₂₄ and R ₂₅ each independently represent

or

Lt; / RTI >

,

또는

일 수 있고, 바람직하게는

일 수 있으며, R₉, R₁₀, R₁₁ 및 R₃₂은 각각 독립적으로 수소 또는 C1 ~ C10의 알킬기일 수 있고, 바람직하게는 C1 ~ C5의 알킬기일 수 있으며, R₁₂는 C1 ~ C10의 알킬렌기일 수 있고, 바람직하게는 C1 ~ C5의 알킬렌기일 수 있다.In Formula 1, R < ₀ >

,

or

, And preferably

R ₉ , R ₁₀ , R ₁₁ and R ₃₂ may each independently be hydrogen or a C 1 to C 10 alkyl group, preferably a C 1 to C 5 alkyl group, and R ₁₂ is a C 1 to C 10 alkyl And may preferably be a C1 to C5 alkylene group.

,

또는

일 수 있고, 바람직하게는

일 수 있다.In the above formula 1, R ₁ is

,

or

, And preferably

Lt; / RTI >

In Formula 1, R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ may each independently be a C 1 to C 15 alkylene group, preferably a C 1 to C 10 alkyl And n, m and l each independently may be a rational number of 1 to 50, preferably 1 to 20, and R < 2 >

또는

일 수 있고, 바람직하게는 C1 ~ C10의 알킬렌기일 수 있으며, 더욱 바람직하게는 C1 ~ C5의 알킬렌기일 수 있고, R₂₇, R₂₈, R₂₉, R₃₀ 및 R₃₁은 각각 독립적으로 C1 ~ C10의 알킬렌기일 수 있으며, 바람직하게는 C1 ~ C10의 알킬렌기일 수 있고, R₂₁, R₂₂ 및 R₂₃은 각각 독립적으로 C1 ~ C10의 알킬기일 수 있고, 바람직하게는 C1 ~ C5의 알킬기일 수 있다.In the above formula 1, R ₁₆ can be an alkyl group of C1 ~ C10, and preferably be an alkyl group of C1 ~ C5, R ₂₀ is an alkylene group of C1 ~ C10,

or

R ₂₇ , R ₂₈ , R ₂₉ , R ₃₀ and R ₃₁ are each independently a C1 to C10 alkylene group, preferably a C1 to C10 alkylene group, more preferably a C1 to C5 alkylene group, may be alkylene date of ~ C10, preferably it may be an alkylene group of _{C1 ~ C10, R 21, R} 22 and R ₂₃ each independently may be an alkyl group of C1 ~ C10, preferably a C1 ~ C5 Alkyl group.

(2)

In the general formula (2), R ₁₇ , R ₁₈ and R ₁₉ may each independently be hydrogen, an aryl group or a C 1 to C 10 alkyl group, preferably a C 1 to C 5 alkyl group.

일 수 있고,Further, the compound represented by the formula (1) is preferably a compound wherein R ₂₄ and R ₂₅ are

Lt; / RTI >

이고, R₂₅는

일 수 있다.The compound represented by the formula (1) is preferably a compound wherein R < ₂₄ >

And R < ₂₅ >

Lt; / RTI >

In addition, the protective coating composition of the present invention may further comprise at least one of a polar organic solvent, a surface modifier additive, a flow modifier, and an adhesion promoter. Preferably, the protective coating composition comprises a polar organic solvent, And an adhesion promoting agent.

In the meantime, the protective coating for the dicing process of the present invention may include a compound represented by the following general formula (10).

[Chemical formula 10]

In Formula 10, R ₁₃ and R ₁₄ may each independently be a C 1 to C 10 alkylene group, preferably a C 1 to C 5 alkylene group, R ₁₅ may be a C 1 to C 10 alkyl group, Preferably a C1 to C5 alkyl group.

또는

일 수 있다.In the above formula (10), R ₂₄ and R ₂₅ each independently represent

or

Lt; / RTI >

,

또는

일 수 있고, 바람직하게는

일 수 있으며, R₉, R₁₀, R₁₁ 및 R₃₂은 각각 독립적으로 수소 또는 C1 ~ C10의 알킬기일 수 있고, 바람직하게는 C1 ~ C5의 알킬기일 수 있으며, R₁₂는 C1 ~ C10의 알킬렌기일 수 있고, 바람직하게는 C1 ~ C5의 알킬렌기일 수 있다.In Formula 10, R < ₀ >

,

or

, And preferably

R ₉ , R ₁₀ , R ₁₁ and R ₃₂ may each independently be hydrogen or a C 1 to C 10 alkyl group, preferably a C 1 to C 5 alkyl group, and R ₁₂ is a C 1 to C 10 alkyl And may preferably be a C1 to C5 alkylene group.

,

또는

일 수 있고, 바람직하게는

일 수 있다.In the above formula (10), R < ₁ >

,

or

, And preferably

Lt; / RTI >

In Formula 10, R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ may each independently be a C 1 to C 15 alkylene group, preferably a C 1 to C 10 alkyl And n, m and l each independently may be a rational number of 1 to 50, preferably 1 to 20, and R < 2 >

또는

일 수 있고, 바람직하게는 C1 ~ C10의 알킬렌기일 수 있으며, 더욱 바람직하게는 C1 ~ C5의 알킬렌기일 수 있고, R₂₇, R₂₈, R₂₉, R₃₀ 및 R₃₁은 각각 독립적으로 C1 ~ C10의 알킬렌기일 수 있으며, R₂₁, R₂₂ 및 R₂₃은 각각 독립적으로 C1 ~ C10의 알킬기일 수 있고, 바람직하게는 C1 ~ C5의 알킬기일 수 있다.In the above Formula 10, R ₁₆ can be an alkyl group of C1 ~ C10, and preferably be an alkyl group of C1 ~ C5, R ₂₀ is an alkylene group of C1 ~ C10,

or

R ₂₇ , R ₂₈ , R ₂₉ , R ₃₀ and R ₃₁ are each independently a C1 to C10 alkylene group, preferably a C1 to C10 alkylene group, more preferably a C1 to C5 alkylene group, And R ₂₁ , R ₂₂ and R ₂₃ may each independently be a C 1 to C 10 alkyl group, preferably a C 1 to C 5 alkyl group.

일 수 있고, R₁₇, R₁₈ 및 R₁₉는 각각 독립적으로 수소, 아릴기 또는 C1 ~ C10의 알킬기일 수 있고, 바람직하게는 C1 ~ C5의 알킬기일 수 있다.In the above formula (10), A ⁺ represents

R ₁₇ , R ₁₈ and R ₁₉ may each independently be hydrogen, an aryl group or a C 1 to C 10 alkyl group, preferably a C 1 to C 5 alkyl group.

일 수 있고,Further, the compound represented by the formula (10) is preferably a compound wherein R < ₂₄ > and R _&

Lt; / RTI >

이고, R₂₅는

일 수 있다.The compound represented by formula (10) is preferably a compound wherein R < ₂₄ >

And R < ₂₅ >

Lt; / RTI >

Furthermore, the protective coating for dicing of the present invention may further comprise at least one of a polar organic solvent, a surface modifying additive, a flow modifier, and an adhesion promoter, and is preferably a polar organic solvent, a surface modifying additive, An adhesion promoting agent. In addition, the protective coating agent for the dicing process of the present invention may further comprise water.

First, the polar organic solvent serves to dissolve the compound represented by the formula (10). The polar organic solvent may include at least one of an alcohol solvent, a ketone solvent, and a glycol ethers solvent, and preferably an alcohol solvent and a ketone And a solvent, and more preferably, a C1-C10 alcohol solvent.

The polar organic solvent may contain 8 to 500 parts by weight, preferably 8 to 36 parts by weight, more preferably 9 to 33 parts by weight, based on 100 parts by weight of the compound represented by the general formula (10) There may be a problem that the compound represented by the general formula (10) precipitates, and if it exceeds 500 parts by weight, there is a problem that the coating of the protective coating agent of the present invention is not properly applied during coating.

Next, the surface modifying additive, which serves to impart slipperiness to the surface after coating using the protective coating of the present invention, may include a silicone-based surface modifying additive, preferably MODAREZ K-SE 305 from PROTEX International , MODAREZ K-SL 106, MODAREZ K-SL 107, and BYK-331, BYK-333, BYK-348 and BYK-3455 of BYK.

The surface modifying additive may include 0.08 to 100 parts by weight, preferably 0.08 to 0.6 part by weight, more preferably 0.09 to 0.55 part by weight, relative to 100 parts by weight of the compound represented by the general formula (10) If it is contained in an amount of less than 1 part by weight, there may be a problem that foreign matter adheres due to insufficient slip property. If it is contained in an amount exceeding 100 parts by weight, adhesion may be deteriorated.

PROX A 300, PROX AM 162 S, SYNTHRO THIX 608, BYK-405, BYK-420 and BYK-7420 of BYK, which are PROTEX international, PROTEX international, ES. ≪ / RTI >

The flow control agent may contain 0.4 to 200 parts by weight, preferably 0.4 to 0.6 parts by weight, more preferably 0.45 to 0.55 parts by weight, relative to 100 parts by weight of the compound represented by the general formula (10) , The coating may have a small thickness when coated with the protective coating of the present invention because of low viscosity. If the coating is used in an amount exceeding 200 parts by weight, the coating may have a high viscosity and non-uniform coating.

Next, the adhesion promoter enhances the adhesion of the protective coating of the present invention, and may include at least one of BYK-4509 and BYK-4500 of BYK.

The adhesion promoting agent may include 0.32 to 250 parts by weight, preferably 0.32 to 1.2 parts by weight, more preferably 0.36 to 1.1 parts by weight, relative to 100 parts by weight of the compound represented by the general formula (10) , There may be a problem that the adhesion is lowered, and when it is more than 250 parts by weight, the slip property may be deteriorated.

Next, the water may include 24 to 48 parts by weight, preferably 27 to 44 parts by weight, more preferably 28.5 to 42 parts by weight, relative to 100 parts by weight of the compound represented by the general formula (10) , There is a problem that when the protective coating agent is coated on the wafer, the coating thickness becomes thick and there may be a problem in peeling off, and when the protective coating agent is contained in an amount exceeding 48 parts by weight, hardening may not be performed well.

Meanwhile, the method for producing a protective coating agent for a dicing process of the present invention includes the first to third steps.

First, a first polymer may be prepared by mixing and polymerizing a compound represented by the following formula (7), a compound represented by the following formula (8), a compound represented by the following formula (9) and a solvent in a first step.

(7)

,

또는

일 수 있고, 바람직하게는

일 수 있다.In Formula 7, R ₁ is

,

or

, And preferably

Lt; / RTI >

In Formula 7, each of R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ may independently be a C 1 to C 15 alkylene group, preferably a C 1 to C 10 alkyl It can be a ring.

In the above formula (1), n, m and 1 each independently may be a positive number of 1 to 50, preferably 1 to 20.

[Chemical Formula 8]

,

또는

일 수 있고, 바람직하게는

일 수 있으다.In Formula 8, R < ₀ >

,

or

, And preferably

.

In Formula 8, R ₉ , R ₁₀ , R _11, and R ₃₂ may each independently be hydrogen or a C 1 to C 10 alkyl group, preferably a C 1 to C 5 alkyl group.

In the general formula (8), R ₁₂ may be a C1-C10 alkylene group, preferably a C1-C5 alkylene group.

[Chemical Formula 9]

In the above formula (9), R ₁₃ and R ₁₄ may each independently be a C 1 to C 10 alkylene group, preferably a C 1 to C 5 alkylene group.

In the above formula (9), R ₁₅ may be a C1-C10 alkyl group, preferably a C1-C5 alkyl group.

The solvent of the first step may include at least one of NMP (N-methylpyrrolidone), DMF (N, N-dimethylformamide), DMA (N, N-dimethylacetamide) and MEK And NMP (N-methylpyrrolidone).

In the first step, the compound represented by the general formula (8) includes 101 to 153 parts by weight, preferably 114 to 140 parts by weight, more preferably 120 to 134 parts by weight, per 100 parts by weight of the compound represented by the general formula If it is contained in an amount less than 101 parts by weight, there may be a problem that the adhesive strength after curing is weakened. If the amount is more than 153 parts by weight, there is a problem that the visibility of the surface of the wafer after coating is deteriorated.

In the first step, the compound represented by the general formula (9) includes 11 to 18 parts by weight, preferably 13 to 17 parts by weight, more preferably 14 to 16 parts by weight, per 100 parts by weight of the compound represented by the general formula If it is contained in an amount of less than 11 parts by weight, there may be a problem that the dispersibility to water is poor. If the amount is more than 18 parts by weight, there may be a problem that the water resistance after curing is inferior.

In the first step, the solvent may include 40 to 61 parts by weight, preferably 45 to 56 parts by weight, more preferably 39 to 45 parts by weight, relative to 100 parts by weight of the compound represented by the general formula (7) If the amount is less than 40 parts by weight, the viscosity may become too strong and the uniformity of the coating may be poor. If the amount is more than 61 parts by weight, the viscosity may become too weak and the coating may not be performed well.

The first stage is a step of mixing and / or mixing at a temperature of 80 to 150 DEG C, preferably 80 to 140 DEG C, 150 to 250 rpm, preferably 170 to 230 rpm for 1 to 3 hours, preferably 1.5 to 2.5 hours, Or a polymerization reaction may be carried out to prepare the first polymer.

At this time, the produced first polymer may be a compound represented by the following formula (5).

[Chemical Formula 5]

In Formula 5, R ₁₃ and R ₁₄ may each independently be a C 1 to C 10 alkylene group, preferably a C 1 to C 5 alkylene group.

In the above formula (5), R ₁₅ may be a C1-C10 alkyl group, preferably a C1-C5 alkyl group.

일 수 있고, R₀은

,

또는

일 수 있고, 바람직하게는

일 수 있으며, R₉, R₁₀, R₁₁ 및 R₃₂은 각각 독립적으로 수소 또는 C1 ~ C10의 알킬기일 수 있고, 바람직하게는 C1 ~ C5의 알킬기일 수 있으며, R₁₂는 C1 ~ C10의 알킬렌기일 수 있고, 바람직하게는 C1 ~ C5의 알킬렌기일 수 있다. In the above formula (5), R < ₂₆ >

And R < ₀ >

,

or

, And preferably

R ₉ , R ₁₀ , R ₁₁ and R ₃₂ may each independently be hydrogen or a C 1 to C 10 alkyl group, preferably a C 1 to C 5 alkyl group, and R ₁₂ is a C 1 to C 10 alkyl And may preferably be a C1 to C5 alkylene group.

,

또는

일 수 있고, 바람직하게는

일 수 있으며, R₂, R₃, R₄, R₅, R₆, R₇ 및 R₈은 각각 독립적으로 C1 ~ C15의 알킬렌기이고, 바람직하게는 C1 ~ C10의 알킬렌기일 수 있으며, n, m, l은 각각 독립적으로 1 ~ 50인 유리수이고, 바람직하게는 1 ~ 20인 유리수일 수 있다.In Formula 5, R < ₁ >

,

or

, And preferably

And R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ are each independently a C 1 to C 15 alkylene group, preferably a C 1 to C 10 alkylene group, and n , m and l are each independently a rational number from 1 to 50, preferably from 1 to 20.

Next, the second step of the production method of the protective coating agent for dicing according to the present invention is a method wherein the first polymer produced in the first step is mixed with at least one compound represented by the following formula (6) and the compound represented by the following formula The second polymer or the third polymer can be prepared by mixing and reacting.

[Chemical Formula 6]

또는

일 수 있고, 바람직하게는 C1 ~ C10의 알킬렌기일 수 있고, 바람직하게는 C1 ~ C5의 알킬렌기일 수 있다. 또한, R₂₇, R₂₈, R₂₉, R₃₀ 및 R₃₁은 각각 독립적으로 C1 ~ C10의 알킬렌기일 수 있고, 바람직하게는 C1 ~ C5의 알킬렌기일 수 있다. In the formula (6), R ₂₀ represents an alkylene group having 1 to 10 carbon atoms,

or

, Preferably a C1-C10 alkylene group, and preferably a C1-C5 alkylene group. Each of R ₂₇ , R ₂₈ , R ₂₉ , R ₃₀ and R ₃₁ may independently be a C 1 to C 10 alkylene group, preferably a C 1 to C 5 alkylene group.

In the above formula (6), R ₂₁ , R ₂₂ and R ₂₃ may each independently be a C 1 to C 10 alkyl group, preferably a C 1 to C 5 alkyl group.

[Chemical Formula 4]

In the above Formula 4, R ₁₆ may be may be an alkyl group of C1 ~ C10, preferably an alkyl group of C1 ~ C5.

The method for producing the second polymer through the second step of the method for producing the protective coating for dicing according to the present invention will be described in detail. The compound represented by the formula 4 is mixed and reacted with the first polymer, 2 polymer, and the second polymer produced may be a compound represented by the following formula (1-1).

[Formula 1-1]

In the above formula 1-1, R ₁₃ and R ₁₄ each independently may be an alkylene group of C1 ~ C10, preferably may be an alkylene group of C1 ~ C5.

In the above formula (1-1), R ₁₅ may be a C1-C10 alkyl group, preferably a C1-C5 alkyl group.

일 수 있다.In the above formula (1-1), R ₂₄ and R ₂₅ represent

Lt; / RTI >

,

또는

일 수 있고, 바람직하게는

일 수 있으며, R₉, R₁₀, R₁₁ 및 R₃₂은 각각 독립적으로 수소 또는 C1 ~ C10의 알킬기일 수 있고, 바람직하게는 C1 ~ C5의 알킬기일 수 있으며, R₁₂는 C1 ~ C10의 알킬렌기일 수 있고, 바람직하게는 C1 ~ C5의 알킬렌기일 수 있다.In Formula 1-1, R < ₀ >

,

or

, And preferably

R ₉ , R ₁₀ , R ₁₁ and R ₃₂ may each independently be hydrogen or a C 1 to C 10 alkyl group, preferably a C 1 to C 5 alkyl group, and R ₁₂ is a C 1 to C 10 alkyl And may preferably be a C1 to C5 alkylene group.

,

또는

일 수 있고, 바람직하게는

일 수 있다.In Formula 1-1, R < ₁ >

,

or

, And preferably

Lt; / RTI >

In Formula 1-1, each of R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ may independently be a C 1 to C 15 alkylene group, And n, m and l each independently may be a rational number of 1 to 50, preferably 1 to 20, and R < 2 >

또는

일 수 있고, 바람직하게는 C1 ~ C10의 알킬렌기일 수 있으며, 더욱 바람직하게는 C1 ~ C5의 알킬렌기일 수 있고, R₂₇, R₂₈, R₂₉, R₃₀ 및 R₃₁은 각각 독립적으로 C1 ~ C10의 알킬렌기일 수 있으며, 바람직하게는 C1 ~ C5의 알킬렌기일 수 있고, R₂₁, R₂₂ 및 R₂₃은 각각 독립적으로 C1 ~ C10의 알킬기일 수 있고, 바람직하게는 C1 ~ C5의 알킬기일 수 있다.In the above formula 1-1, R ₁₆ can be an alkyl group of C1 ~ C10, and preferably be an alkyl group of C1 ~ C5, R ₂₀ is an alkylene group of C1 ~ C10,

or

R ₂₇ , R ₂₈ , R ₂₉ , R ₃₀ and R ₃₁ are each independently a C1 to C10 alkylene group, preferably a C1 to C10 alkylene group, more preferably a C1 to C5 alkylene group, And R ₂₁ , R ₂₂ and R ₂₃ may each independently be a C 1 to C 10 alkyl group, preferably a C 1 to C 5 alkylene group, preferably a C 1 to C 5 alkylene group, Alkyl group.

Further, when the second polymer is produced in the second step, the compound represented by the general formula (4) is used in an amount of 29 to 45 parts by weight, preferably 33 to 41 parts by weight, more preferably If the amount is less than 29 parts by weight, there may be a problem that the adhesive remains after the curing. If the amount exceeds 45 parts by weight, there is a problem that the thickness of the coating after curing becomes thin.

Further, when the second polymer is produced in the second step, it is preferably carried out at a temperature of 70 to 110 ° C, preferably 80 to 100 ° C, at 150 to 250 rpm, preferably at 170 to 230 rpm for 10 to 40 minutes, The second polymer may be prepared by mixing and / or reacting for 20 to 30 minutes.

Meanwhile, the method for producing the third polymer through the second step of the method for producing the protective coating agent for dicing according to the present invention may specifically include steps 2-1 and 2-2.

The second step of the method for producing the protective coating agent for dicing according to the present invention can produce the third intermediate polymer by mixing and reacting the compound represented by the formula (6) with the prepared first polymer, 3 The intermediate polymer may be a compound represented by the following formula (3).

(3)

For Formula 3, R ₁₃ and R ₁₄ each independently may be an alkylene group of C1 ~ C10, preferably may be an alkylene group of C1 ~ C5.

In Formula 3, R ₁₅ may be a C1-C10 alkyl group, preferably a C1-C5 alkyl group.

이고, R₂₅는

일 수 있다.In Formula 3, R < ₂₆ >

And R < ₂₅ >

Lt; / RTI >

,

또는

일 수 있고, 바람직하게는

일 수 있으며, R₉, R₁₀, R₁₁ 및 R₃₂은 각각 독립적으로 수소 또는 C1 ~ C10의 알킬기일 수 있고, 바람직하게는 C1 ~ C5의 알킬기일 수 있으며, R₁₂는 C1 ~ C10의 알킬렌기일 수 있고, 바람직하게는 C1 ~ C5의 알킬렌기일 수 있다.In Formula 3, R < ₀ >

,

or

, And preferably

R ₉ , R ₁₀ , R ₁₁ and R ₃₂ may each independently be hydrogen or a C 1 to C 10 alkyl group, preferably a C 1 to C 5 alkyl group, and R ₁₂ is a C 1 to C 10 alkyl And may preferably be a C1 to C5 alkylene group.

,

또는

일 수 있고, 바람직하게는

일 수 있다.In Formula 3, R < ₁ >

,

or

, And preferably

Lt; / RTI >

In Formula 3, R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ each independently represent a C 1 to C 15 alkylene group, preferably a C 1 to C 10 alkyl And n, m and l each independently may be a rational number of 1 to 50, preferably 1 to 20, and R < 2 >

또는

일 수 있고, 바람직하게는 C1 ~ C10의 알킬렌기일 수 있으며, 더욱 바람직하게는 C1 ~ C5의 알킬렌기일 수 있고, R₂₇, R₂₈, R₂₉, R₃₀ 및 R₃₁은 각각 독립적으로 C1 ~ C10의 알킬렌기일 수 있고, 바람직하게는 C1 ~ C5의 알킬렌기일 수 있으며, R₂₁, R₂₂ 및 R₂₃은 각각 독립적으로 C1 ~ C10의 알킬기일 수 있고, 바람직하게는 C1 ~ C5의 알킬기일 수 있다.In the above formula (3), R ₂₀ represents an alkylene group having from 1 to 10 carbon atoms,

or

R ₂₇ , R ₂₈ , R ₂₉ , R ₃₀ and R ₃₁ are each independently a C1 to C10 alkylene group, preferably a C1 to C10 alkylene group, more preferably a C1 to C5 alkylene group, And R ₂₁ , R ₂₂ and R ₂₃ may each independently be a C 1 to C 10 alkyl group, preferably a C 1 to C 5 alkylene group, preferably a C 1 to C 10 alkylene group, Alkyl group.

When the third intermediate polymer is produced in Step 2-1, the compound represented by Formula 6 is used in an amount of 33 to 51 parts by weight, preferably 37 to 47 parts by weight, based on 100 parts by weight of the compound represented by Formula 7 And more preferably 39 to 45 parts by weight. If the amount is less than 33 parts by weight, there may be a problem that the uniformity of the coating surface after the curing is deteriorated. If the amount exceeds 51 parts by weight, There may be a problem.

Further, when the third intermediate polymer is produced in the second step, the temperature is preferably 80 to 150 ° C, preferably 80 to 140 ° C, at 150 to 250 rpm, preferably at 170 to 230 rpm for 60 to 120 minutes, Can be mixed and / or reacted for 75 to 105 minutes to produce a third intermediate polymer.

Step 2-2 of the process for producing a protective coating for dicing according to the present invention comprises The third polymer may be prepared by mixing and reacting the compound represented by Formula 4 with the third intermediate polymer prepared in Step 2-1. The third polymer may be a compound represented by Formula 1-2 .

[Formula 1-2]

In the above formula (1-2), R ₁₃ and R ₁₄ each independently represent a C 1 to C 10 alkylene group, preferably a C 1 to C 5 alkylene group.

In Formula 1-2, R ₁₅ may be a C1-C10 alkyl group, preferably a C1-C5 alkyl group.

이고, R₂₅는

일 수 있다.In Formula 1-2, R ₂₄ represents

And R < ₂₅ >

Lt; / RTI >

,

또는

일 수 있고, 바람직하게는

일 수 있으며, R₉, R₁₀, R₁₁ 및 R₃₂은 각각 독립적으로 수소 또는 C1 ~ C10의 알킬기일 수 있고, 바람직하게는 C1 ~ C5의 알킬기일 수 있으며, R₁₂는 C1 ~ C10의 알킬렌기일 수 있고, 바람직하게는 C1 ~ C5의 알킬렌기일 수 있다.In Formula 1-2, R < ₀ >

,

or

, And preferably

R ₉ , R ₁₀ , R ₁₁ and R ₃₂ may each independently be hydrogen or a C 1 to C 10 alkyl group, preferably a C 1 to C 5 alkyl group, and R ₁₂ is a C 1 to C 10 alkyl And may preferably be a C1 to C5 alkylene group.

,

또는

일 수 있고, 바람직하게는

일 수 있다.In Formula 1-2, R < ₁ >

,

or

, And preferably

Lt; / RTI >

In Formula 1-2, R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ may each independently be a C 1 to C 15 alkylene group, preferably C 1 to C 10 And n, m and l each independently may be a rational number of 1 to 50, preferably 1 to 20, and R < 2 >

또는

일 수 있고, 바람직하게는 C1 ~ C10의 알킬렌기일 수 있으며, 더욱 바람직하게는 C1 ~ C5의 알킬렌기일 수 있고, R₂₇, R₂₈, R₂₉, R₃₀ 및 R₃₁은 각각 독립적으로 C1 ~ C10의 알킬렌기이며, R₂₁, R₂₂ 및 R₂₃은 각각 독립적으로 C1 ~ C10의 알킬기일 수 있고, 바람직하게는 C1 ~ C5의 알킬기일 수 있다.In the above formula 1-2, R ₁₆ can be an alkyl group of C1 ~ C10, and preferably be an alkyl group of C1 ~ C5, R ₂₀ is an alkylene group of C1 ~ C10,

or

R ₂₇ , R ₂₈ , R ₂₉ , R ₃₀ and R ₃₁ are each independently a C1 to C10 alkylene group, preferably a C1 to C10 alkylene group, more preferably a C1 to C5 alkylene group, And R ₂₁ , R ₂₂ and R ₂₃ each independently represent a C1-C10 alkyl group, preferably a C1-C5 alkyl group.

When the third polymer is produced in Step 2-2, the compound represented by Formula 4 is used in an amount of 29 to 45 parts by weight, preferably 33 to 41 parts by weight, If the amount of the curing agent is less than 29 parts by weight, there may be a problem that the adhesive residue remains after curing. If the amount exceeds 45 parts by weight, there is a problem that the thickness of the coating after curing becomes thin have.

When the third polymer is produced in step 2-2, it is preferable that the temperature is from 70 to 110 DEG C, preferably from 80 to 100 DEG C, from 150 to 250 rpm, preferably from 170 to 230 rpm, And / or may be mixed and / or reacted for 20 to 30 minutes to prepare a third polymer.

Finally, the third step of the method for producing the protective coating agent for dicing process comprises mixing and reacting the produced second polymer or third polymer with a compound represented by the following formula (2) and water to prepare a compound represented by the following formula (10) can do.

(2)

In Formula 2, R ₁₇ , R ₁₈ and R ₁₉ may each be hydrogen, an aryl group or a C 1 to C 10 alkyl group, preferably a C 1 to C 5 alkyl group.

[Chemical formula 10]

In Formula 10, R ₁₃ and R ₁₄ may each independently be a C 1 to C 10 alkylene group, preferably a C 1 to C 5 alkylene group, R ₁₅ may be a C 1 to C 10 alkyl group, Preferably a C1 to C5 alkyl group.

또는

일 수 있다.In the above formula (10), R ₂₄ and R ₂₅ each independently represent

or

Lt; / RTI >

,

또는

일 수 있고, 바람직하게는

일 수 있으며, R₉, R₁₀, R₁₁ 및 R₃₂은 각각 독립적으로 수소 또는 C1 ~ C10의 알킬기일 수 있고, 바람직하게는 C1 ~ C5의 알킬기일 수 있으며, R₁₂는 C1 ~ C10의 알킬렌기일 수 있고, 바람직하게는 C1 ~ C5의 알킬렌기일 수 있다.In Formula 10, R < ₀ >

,

or

, And preferably

R ₉ , R ₁₀ , R ₁₁ and R ₃₂ may each independently be hydrogen or a C 1 to C 10 alkyl group, preferably a C 1 to C 5 alkyl group, and R ₁₂ is a C 1 to C 10 alkyl And may preferably be a C1 to C5 alkylene group.

,

또는

일 수 있고, 바람직하게는

일 수 있다.In the above formula (10), R < ₁ >

,

or

, And preferably

Lt; / RTI >

In Formula 10, R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ may each independently be a C 1 to C 15 alkylene group, preferably a C 1 to C 10 alkyl And n, m and l each independently may be a rational number of 1 to 50, preferably 1 to 20, and R < 2 >

또는

일 수 있고, 바람직하게는 C1 ~ C10의 알킬렌기일 수 있으며, 더욱 바람직하게는 C1 ~ C5의 알킬렌기일 수 있고, R₂₇, R₂₈, R₂₉, R₃₀ 및 R₃₁은 각각 독립적으로 C1 ~ C10의 알킬렌기이고, R₂₁, R₂₂ 및 R₂₃은 각각 독립적으로 C1 ~ C10의 알킬기일 수 있고, 바람직하게는 C1 ~ C5의 알킬기일 수 있다.In the above Formula 10, R ₁₆ can be an alkyl group of C1 ~ C10, and preferably be an alkyl group of C1 ~ C5, R ₂₀ is an alkylene group of C1 ~ C10,

or

R ₂₇ , R ₂₈ , R ₂₉ , R ₃₀ and R ₃₁ are each independently a C1 to C10 alkylene group, preferably a C1 to C10 alkylene group, more preferably a C1 to C5 alkylene group, And R ₂₁ , R ₂₂ and R ₂₃ may each independently be a C 1 to C 10 alkyl group, preferably a C 1 to C 5 alkyl group.

일 수 있고, R₁₇, R₁₈ 및 R₁₉는 각각 독립적으로 수소, 아릴기 또는 C1 ~ C10의 알킬기일 수 있고, 바람직하게는 C1 ~ C5의 알킬기일 수 있다.In the above formula (10), A ⁺ represents

R ₁₇ , R ₁₈ and R ₁₉ may each independently be hydrogen, an aryl group or a C 1 to C 10 alkyl group, preferably a C 1 to C 5 alkyl group.

일 수 있으며, The third step of the method for producing the protective coating agent for dicing process will be described in more detail. The third step of the method for producing the protective coating agent for dicing includes the steps of mixing and reacting the compound represented by Formula 2 with water to the second polymer prepared through the second step, The compound represented by formula (10) is a compound wherein R < ₂₄ > and R _&

Lt; / RTI >

일 수 있고, R₂₅는

일 수 있다.Claim to a compound and the water represented by the above formula (2) in the third polymer prepared in step 2, the mixing and reaction of producing the compound represented by the formula (10) is R ₂₄

And R < ₂₅ >

Lt; / RTI >

In the third step, when the compound represented by Formula 10 is prepared, the compound represented by Formula 2 is used in an amount of 8 to 13 parts by weight, preferably 9 to 12 parts by weight, per 100 parts by weight of the compound represented by Formula 7 And more preferably 9.5 to 11 parts by weight. If the amount is less than 8 parts by weight, the water dispersion may not be satisfactory. If the amount of the component is more than 11 parts by weight, There may still be a problem that remains after.

In the third step, when preparing the compound represented by Formula 10, water is added in an amount of 533 to 800 parts by weight, preferably 600 to 733 parts by weight, more preferably, May contain 632 to 700 parts by weight. If it is contained in an amount of less than 533 parts by weight, there may be a problem that the viscosity becomes too strong. When the amount exceeds 800 parts by weight, the content of the compound represented by the formula 1 becomes too low, There may be a problem losing.

In the fourth step, the compound represented by Formula 2 and water are heated at a temperature of 10 to 50 ° C., preferably 15 to 30 ° C., at 400 to 700 rpm, preferably 500 to 600 rpm for 10 to 120 minutes, , The mixture is prepared at a temperature of 10 to 50 DEG C, preferably 15 to 30 DEG C, at 400 to 700 rpm, preferably at 500 to 600 rpm for 1 to 5 hours , Preferably 1 to 2 hours, to the second polymer or the third polymer to prepare a compound represented by the above formula (10).

In the meantime, the method for preparing a protective coating for dicing according to the present invention can use a polar organic solvent, a surface controlling additive, a flow control agent, an adhesion promoter and water in combination with the compound represented by the formula (10).

The thus-prepared protective coating agent for the dicing process can be used in a wafer processing process as described below as an example.

The wafer processing process includes a wafer dicing process including a first process of coating the wafer surface with the above-mentioned protective coating of the present invention, a second process of placing the wafer in the pulling device, and a third process of dicing the wafer A fifth step of peeling off the protective coating for dicing according to the present invention from the selected good products, and a step for protecting the dicing step of the present invention And a sixth step of inspecting the good where the coating is peeled off.

The first step may be performed at 0 to 50 ° C for 1 to 60 seconds, preferably at 15 to 35 ° C for 20 to 50 seconds.

On the other hand, the coating agent for dicing of the present invention is not necessarily applied to a semiconductor process, but can be preferably applied to a glass manufacturing process which can cause damage or foreign matter contamination due to scratches or the like in the manufacturing process

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments. It will be understood that various changes and modifications may be made without departing from the scope of the present invention. For example, each component specifically illustrated in the embodiments of the present invention can be modified and implemented. It is to be understood that all changes and modifications that come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.

Example 1: Preparation of protective coating agent for dicing process

(1) In a reactor, a compound represented by the following formula (7-1), a compound represented by the following formula (8-1), a compound represented by the following formula (9-1) and NMP (N-methylpyrrolidone) The temperature was adjusted to 100 占 폚. Thereafter, the mixture was polymerized at 200 rpm for 2 hours to prepare a first polymer.

To 100 parts by weight of the compound represented by the following formula (7-1), 126.7 parts by weight of the compound represented by the following general formula (8-1), 14.8 parts by weight of the compound represented by the following general formula (9-1) and NMP (N-methylpyrrolidone) 50.5 parts by weight were used.

[Formula 7-1]

이고, R₂는 -CH₂CH₂CH₂CH₂CH₂CH₂CH₂-이며, R₃는 -CH₂CH₂CH₂CH₂CH₂CH₂CH₂CH₂-이고, n는 7이다.In the formula (7-1), R ₁ is

And, R ₂ is _{-CH 2 CH 2 CH 2 CH 2} CH 2 CH 2 CH 2 - , and, R ₃ is _{-CH 2 CH 2 CH 2 CH 2} CH 2 CH 2 CH 2 CH 2 - and, n is 7 .

[Formula 8-1]

이고, R₉, R₁₀ 및 R₁₁은 메틸기이고, R₁₂는 메틸렌기이다.In the formula (8-1), R < ₀ >

, R ₉ , R ₁₀ and R ₁₁ are methyl groups, and R ₁₂ is a methylene group.

[Formula 9-1]

In the above formula (9-1), R ₁₃ and R ₁₄ are methylene groups and R ₁₅ is an ethyl group.

(2) The compound represented by the following formula (6-1) was added to the prepared first polymer and mixed and reacted at 90 RPM for 90 minutes at 200 RPM to prepare a third intermediate polymer.

At that time, 42 parts by weight of the compound represented by the following formula (6-1) was used for 100 parts by weight of the compound represented by the above formula (7-1).

[Formula 6-1]

In the formula (6-1), R ₂₀ is -CH ₂ CH ₂ CH ₂ -, and R ₂₁ , R ₂₂ and R ₂₃ are methyl groups.

(3) A compound represented by the following formula (4-1) was added to the prepared third intermediate polymer at a temperature of 90 占 폚 and mixed and reacted at 200 RPM for 25 minutes to prepare a third polymer.

At this time, 36.8 parts by weight of the compound represented by the following formula (4-1) was used for 100 parts by weight of the compound represented by the above formula (7-1).

[Formula 4-1]

In the above formula (4-1), R ₁₆ is an ethyl group.

(4) A compound represented by the following formula (2-1) and water were mixed at 25 DEG C and 550 RPM for 1 hour to prepare a mixture. The mixture was added to the prepared third polymer and mixed and reacted at 25 DEG C and 550 RPM for 1 hour to prepare a compound represented by the following formula (10-1).

At this time, 10.1 parts by weight of the compound represented by the following formula (2-1) and 666.3 parts by weight of water were used for 100 parts by weight of the compound represented by the above formula (7-1).

[Formula 2-1]

In the general formula (2-1), R ₁₇ , R ₁₈ and R ₁₉ are each an ethyl group.

[Formula 10-1]

이고, R₂₅는

이며, R₀은

이고, R₉, R₁₀ 및 R₁₁은 메틸기이며, R₁₂는 메틸렌기이고, R₁은

이고, R₂는 -CH₂CH₂CH₂CH₂CH₂CH₂CH₂-이며, R₃는 -CH₂CH₂CH₂CH₂CH₂CH₂CH₂CH₂-이고, n는 7이며, R₁₆은 에틸기이고, R₂₀은 -CH₂CH₂CH₂-이며, R₂₁, R₂₂ 및 R₂₃은 메틸기이며, A⁺는

이고, R₁₇, R₁₈ 및 R₁₉는 에틸기이다.In the above formula (10-1), R ₁₃ and R ₁₄ are methylene groups, R ₁₅ is an ethyl group, and R ₂₄ is

And R < ₂₅ >

And R < ₀ >

R ₉ , R ₁₀ and R ₁₁ are methyl groups, R ₁₂ is a methylene group, R ₁ is

And, R ₂ is _{-CH 2 CH 2 CH 2 CH 2} CH 2 CH 2 CH 2 - , and, R ₃ is _{-CH 2 CH 2 CH 2 CH 2} CH 2 CH 2 CH 2 CH 2 - and, n is 7 and , R ₁₆ is an ethyl group, R ₂₀ is -CH ₂ CH ₂ CH ₂ -, R ₂₁ , R ₂₂ and R ₂₃ are methyl groups, A ⁺ is

And R ₁₇ , R ₁₈ and R ₁₉ are an ethyl group.

Examples 2 to 13: Preparation of protective coating agent for dicing process

A protective coating for dicing process was prepared in the same manner as in Example 1. However, protective coatings for the dicing process were prepared by varying the amounts of the compounds used as shown in Table 1 below.

Example 14: Preparation of protective coating agent for dicing process

(1) In a reactor, a compound represented by the following formula (7-1), a compound represented by the following formula (8-1), a compound represented by the following formula (9-1) and NMP (N-methylpyrrolidone) The temperature was adjusted to 100 占 폚. Thereafter, the mixture was polymerized at 200 rpm for 2 hours to prepare a first polymer.

To 100 parts by weight of the compound represented by the following formula (7-1), 126.7 parts by weight of the compound represented by the following general formula (8-1), 14.8 parts by weight of the compound represented by the following general formula (9-1) and NMP (N-methylpyrrolidone) 50.5 parts by weight were used.

[Formula 7-1]

이고, R₂는 -CH₂CH₂CH₂CH₂CH₂CH₂CH₂CH₂-이며, R₃는 -CH₂CH₂CH₂CH₂CH₂CH₂CH₂-이고, n는 9이다.In the formula (7-1), R ₁ is

, R ₂ is -CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ -, R ₃ is -CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ -, and n is 9 .

[Formula 8-1]

이고, R₉, R₁₀ 및 R₁₁은 메틸기이고, R₁₂는 메틸렌기이다.In the formula (8-1), R < ₀ >

, R ₉ , R ₁₀ and R ₁₁ are methyl groups, and R ₁₂ is a methylene group.

[Formula 9-1]

In the above formula (9-1), R ₁₃ and R ₁₄ are methylene groups and R ₁₅ is an ethyl group.

(2) The compound represented by the following formula (4-1) was added to the prepared first polymer at a temperature of 90 占 폚 and mixed and reacted at 200 RPM for 25 minutes to prepare a second polymer.

At this time, 36.8 parts by weight of the compound represented by the following formula (4-1) was used for 100 parts by weight of the compound represented by the above formula (7-1).

[Formula 4-1]

In the above formula (4-1), R ₁₆ is an ethyl group.

(3) A compound represented by the following formula (2-1) and water were mixed at 25 DEG C and 550 RPM for 1 hour to prepare a mixture. The mixture was added to the prepared second polymer and mixed and reacted at 25 DEG C and 550 RPM for 1 hour to prepare a compound represented by the following formula (10-2).

At this time, 10.1 parts by weight of the compound represented by the following formula (2-1) and 666.3 parts by weight of water were used for 100 parts by weight of the compound represented by the above formula (7-1).

[Formula 2-1]

In the general formula (2-1), R ₁₇ , R ₁₈ and R ₁₉ are each an ethyl group.

[Formula 10-2]

이고, R₀은

이고, R₉, R₁₀ 및 R₁₁은 메틸기이며, R₁₂는 메틸렌기이고, R₁은

이고, R₂는 -CH₂CH₂CH₂CH₂CH₂CH₂CH₂CH₂-이며, R₃는 -CH₂CH₂CH₂CH₂CH₂CH₂CH₂-이고, n는 9이고, R₁₆은 에틸기이며, R₂₀은 -CH₂CH₂CH₂-이고, R₂₁, R₂₂ 및 R₂₃은 메틸기이며, A⁺는

이고, R₁₇, R₁₈ 및 R₁₉는 에틸기이다.Wherein R ₁₃ and R ₁₄ are methylene groups, R ₁₅ is an ethyl group, R ₂₄ and R ₂₅ are each a methylene group,

And R < ₀ >

R ₉ , R ₁₀ and R ₁₁ are methyl groups, R ₁₂ is a methylene group, R ₁ is

And, R ₂ is _{-CH 2 CH 2 CH 2 CH 2} CH 2 CH 2 CH 2 CH 2 - , and, R ₃ is _{-CH 2 CH 2 CH 2 CH 2} CH 2 CH 2 CH 2 - and, n is 1-9 and , R ₁₆ is an ethyl group, R ₂₀ is -CH ₂ CH ₂ CH ₂ -, R ₂₁ , R ₂₂ and R ₂₃ are methyl groups, A ⁺ is

And R ₁₇ , R ₁₈ and R ₁₉ are an ethyl group.

Production Examples 1 to 13

Examples 1 to 13 < RTI ID = 0.0 > 10 parts by weight of isopropyl alcohol as a polar organic solvent, 0.1 parts by weight of a surface modifying additive (BYK, BYK-333), and a flow control agent (PROTEX international, PROX A 300), 0.4 parts by weight of an adhesion promoter (BYK, BYK-4509) and 30 parts by weight of water were mixed at 25 DEG C and 500 RPM for 60 minutes to prepare a protective coating for a dicing process.

Production Example 14

Example 14 < RTI ID = 0.0 > 30 parts by weight of tetrahydrofurfuryl alcohol as a polar organic solvent, 0.5 part by weight of a surface modifying additive (BYK, BYK-331), a flow control agent (PROTEX international, PROX AM 162 S), 1 part by weight of adhesion promoter (BYK, BYK-4500) and 40 parts by weight of water were mixed at 25 DEG C and 500 RPM for 60 minutes to prepare a protective coating for dicing.

Experimental Example 1

Using the protective coating for dicing process prepared in Production Examples 1 to 14, the wafer was spin-coated and then thermally cured at 120 ° C for 1 minute. The following physical properties were measured and the results are shown in Table 2.

(1) Pencil Hardness

A pencil hardness measuring pencil was inserted into a hardness tester (CORE TECH) at an angle of 45 °, and a uniform load (1 kg) was applied while pushing it. The pencil used was a Mitsubishi pencil, and pencils indicating the strength of H-9H, F, HB, B-6B and the like were used.

(2) Adhesion

The cured coating layer was scratched with a cutter on a cured coating layer based on ASTM D 3359, and the 3M tape was closely adhered to the coating layer. Then, the coating layer was peeled off several times with a constant force to observe the adhesion between the coating layer and the substrate. The surface of the coated support was scribed with a cross section at 1 mm intervals at 1 mm intervals to make 100 positive directions, and a tape (3M Tape) was attached thereon and then pulled rapidly to evaluate the surface. If the number of remaining eyes is 100

5B, 95 or more are 4B, 85 or more are 3B, 65 or more are 2B, 35 or more are 1B, and less than 0B.

3. Abrasion resistance (%)

In order to measure the abrasion resistance of the coated film, a Taber abraser (QM600T, Qmesys) was used, which was subjected to a load of 500 g each, was worn from 50 to 300 times at a speed of 70 rpm and then subjected to UV-Visible spectrometer (UV-2450, Shimadzu) And the transmittance was measured in the region of 600 nm. The degree of wear resistance of the coating film was determined by defining% transmittance loss (%) as shown below, and the higher the% loss of permeability, the worse the wear resistance of the sample.

Transmittance Loss% = 100 (B-A) / B

A = transmittance (%) at a wavelength of 600 nm after measurement of abrasion resistance of a sample

B = transmittance (%) at a wavelength of 600 nm before measurement of abrasion resistance of a sample

As shown in Table 2, it was confirmed that the protective coatings for dicing process prepared in Preparation Examples 1 and 14 were not only excellent in pencil hardness and adhesive strength but also remarkably low in abrasion resistance.

In addition, it was confirmed that the protective coatings for the dicing process manufactured in Production Examples 1 to 3 were superior in pencil hardness and adhesive force as compared with the protective coatings for dicing process prepared in Production Examples 4 to 5, and were also low in abrasion resistance .

In addition, it was confirmed that the protective coatings for dicing process manufactured in Production Examples 1, 6 to 7 had better pencil hardness and adhesive strength than the protective coatings for dicing process prepared in Production Examples 8 to 9, and also had low abrasion resistance I could.

In addition, it was confirmed that the protective coatings for the dicing process prepared in Production Examples 1 and 10 to 11 were superior in pencil hardness and adhesive force to the protective coatings for dicing process prepared in Production Examples 12 to 13, and were also low in abrasion resistance I could.

It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.

Claims (10)

Wherein the protective coating is coated on the surface of the wafer.
The method according to claim 1,
Wherein the protective coating has a pencil hardness of 2H to 5H, an adhesion of 2B to 5B and an abrasion resistance of 8 to 35%.
3. The method of claim 2,
Wherein the protective coating comprises a compound represented by the following formula (10).
[Chemical formula 10]

In the formula (10), R ₁₃ and R ₁₄ are each independently a C 1 to C 10 alkylene group, R ₁₅ is a C 1 to C 10 alkyl group, R ₂₄ and R ₂₅ each independently

or

And R < ₀ >

,

or

R ₉ , R ₁₀ , R ₁₁ and R ₃₂ are each independently hydrogen or a C 1 to C 10 alkyl group, R ₁₂ is a C 1 to C 10 alkylene group, R ₁ is

,

or

And n, m and l are each independently a rational number of 1 to 50, and R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ and R ₈ are each independently a C 1 to C 15 alkylene group, R ₁₆ is an alkyl group of C1 ~ C10, R ₂₀ is an alkylene group of C1 ~ C10,

or

_{And, R 27, R 28, R} 29, R 30 and R ₃₁ are each independently an alkylene group of _{C1 ~ C10, R 21, R} 22 and R ₂₃ is an alkyl group of C1 ~ C10, each independently, A ⁺ is

And R ₁₇ , R ₁₈ and R ₁₉ are each independently hydrogen, an aryl group or an alkyl group of a C1 to C10 alkyl group.
The method of claim 3,
Wherein the protective coating further comprises at least one of a polar organic solvent, a surface modifying additive, a flow control agent, and an adhesion promoter.
5. The method of claim 4,
Wherein the protective coating comprises a polar organic solvent, a surface modifying additive, a flow control agent and an adhesion promoter.
6. The method of claim 5,
8 to 500 parts by weight of a polar organic solvent, 0.08 to 100 parts by weight of a surface modifying additive, 0.4 to 200 parts by weight of a flow control agent and 0.32 to 250 parts by weight of an adhesion promoter are added to 100 parts by weight of the compound represented by the general formula (10) ≪ / RTI > wherein the protective coating is a coating for a dicing process.
The method of claim 3,
R ₂₄ and R ₂₅ of the compound represented by the formula (10)

≪ / RTI > wherein the protective coating composition is a protective coating for a dicing process.
The method of claim 3,
The R ₂₄ of the compound represented by the formula (10)

And R < ₂₅ >

≪ / RTI > wherein the protective coating composition is a protective coating for a dicing process.
A first step of coating the wafer surface with a protective coating for dicing according to any one of claims 1 to 8;
A second step of arranging the wafer in a pulling device; And
A third step of dicing the wafer;
And a wafer dicing step of dicing the wafer.
The method according to claim 1,
Wherein the first step is performed at 0 to 50 DEG C for 1 to 60 seconds.