JP7314055B2 - Compound, latent base generator, photosensitive resin composition containing said compound, and cured product - Google Patents

Description

The present invention relates to a novel compound useful as a polymerization initiator used in a photosensitive resin composition, a latent base generator containing the compound, a photosensitive resin composition containing the compound in a photosensitive resin, and a cured product of the photosensitive resin composition.

In general, a photosensitive resin composition is obtained by adding a photopolymerization initiator to a photosensitive resin, and can be polymerized, cured, or developed by irradiation with energy rays (light).

Photopolymerization initiators are classified into photoradical generators, photoacid generators, and photobase generators depending on the difference in active species generated by irradiation with energy rays (light). Photoradical generators have advantages such as a fast curing speed and no active species remaining after curing, but they have the disadvantage that oxygen inhibits curing, so a layer that blocks oxygen must be provided when curing a thin film. Photoacid generators have the advantage of not being inhibited by oxygen, but have the disadvantages of corroding metal substrates and denaturing resins after curing due to the residual acid of the active species. Photobase generators are attracting attention because they are unlikely to cause problems such as curing inhibition due to oxygen and corrosion due to residual active species, but generally have a problem of low sensitivity (low curability) compared to photoacid generators. Photobase generators are disclosed in Patent Documents 1 to 4, for example.

US6551761 US8957212 WO2010/064632 US9594302

Accordingly, an object of the present invention is to provide a novel compound exhibiting sufficient absorption in long-wavelength ultraviolet rays (in particular, 365 nm) and having satisfactory sensitivity (base generating ability), a latent base generator containing the compound, a photosensitive resin composition containing the compound as a polymerization initiator, and a cured product thereof.

The present inventor conducted extensive studies and found that a compound having a specific structure has high sensitivity (base generating ability) as a polymerization initiator.

The present invention achieves the above objects by providing the following [1] to [9].

（式中、Ｒ^１は、水素原子、シアノ基、無置換若しくは置換基を有している炭素原子数１～２０の脂肪族炭化水素基又は無置換若しくは置換基を有している炭素原子数６～２０の芳香族炭化水素基を表し、
Ｒ^２、Ｒ^４、Ｒ^５、Ｒ^６及びＲ^７は、それぞれ独立に、水素原子、シアノ基、ニトロ基、－ＯＲ^８、－ＣＯＯＲ^８、－ＣＯ－Ｒ^８、－ＳＲ^８、ハロゲン原子、無置換若しくは置換基を有している炭素原子数１～２０の脂肪族炭化水素基、無置換若しくは置換基を有している炭素原子数６～２０の芳香族炭化水素基又は無置換若しくは置換基を有している炭素原子数２～２０の複素環を含有する基を表し、
Ｒ^３は、無置換若しくは置換基を有している炭素原子数１～２０の脂肪族炭化水素基、無置換若しくは置換基を有している炭素原子数６～２０の芳香族炭化水素基又は複素環を含有し且つ無置換若しくは置換基を有している炭素原子数２～２０の基を表し、
Ｒ^８は、水素原子、無置換若しくは置換基を有している炭素原子数１～２０の脂肪族炭化水素基、無置換若しくは置換基を有している炭素原子数６～２０の芳香族炭化水素基又は複素環を含有し且つ無置換若しくは置換基を有している炭素原子数２～２０の基を表し、
Ｘ^１は、－ＮＲ^１１Ｒ^１２、下記（ａ）又は下記（ｂ）で表される基であり、
Ｒ^１１及びＲ^１２は、それぞれ独立に、水素原子、無置換若しくは置換基を有している炭素原子数１～２０の脂肪族炭化水素基又は無置換若しくは置換基を有している炭素原子数６～２０の芳香族炭化水素基であるか、
Ｒ^１１及びＲ^１２が互いに連結して、無置換若しくは置換基を有し且つ水素原子、窒素原子及び炭素原子からなる炭素原子数１～２０の環、又は無置換若しくは置換基を有し且つ水素原子、酸素原子、窒素原子及び炭素原子からなる炭素原子数１～２０の環を形成しており、
ｎは、０又は１を表す。）

（式中、Ｒ^１３、Ｒ^１４、Ｒ^１５、Ｒ^１６、Ｒ^１７、Ｒ^１８、Ｒ^１９、Ｒ^２０、Ｒ^２１及びＲ^２２は、それぞれ独立に、水素原子、無置換若しくは置換基を有している炭素原子数１～２０の脂肪族炭化水素基又は無置換若しくは置換基を有している炭素原子数６～２０の芳香族炭化水素基であるか、
Ｒ^１３とＲ^１４、Ｒ^１５とＲ^１６、Ｒ^１７とＲ^１８、Ｒ^１９とＲ^２０及びＲ^２１とＲ^２２のうちの少なくとも一組が互いに連結して、無置換若しくは置換基を有し且つ水素原子、窒素原子及び炭素原子からなる炭素原子数１～２０の環、又は無置換若しくは置換基を有し且つ水素原子、酸素原子、窒素原子及び炭素原子からなる炭素原子数１～２０の環を形成しており、
＊は結合手を表す。）[1] A compound represented by the following general formula (I).

(wherein R ¹ represents a hydrogen atom, a cyano group, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms,
R ² , R ⁴ , R ⁵ , R ⁶ and R ⁷ are each independently a hydrogen atom, a cyano group, a nitro group, -OR ⁸ , -COOR ⁸ , -CO-R ⁸ , -SR ⁸ , a halogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or an unsubstituted or substituted group. represents a group containing a heterocyclic ring having 2 to 20 carbon atoms,
R ³ represents an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or a group containing a heterocyclic ring and having 2 to 20 carbon atoms and being unsubstituted or substituted;
R ⁸ represents a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or a group containing a heterocyclic ring and having 2 to 20 carbon atoms and being unsubstituted or substituted;
X ¹ is —NR ¹¹ R ¹² , a group represented by (a) or (b) below,
R ¹¹ and R ¹² are each independently a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms,
R ¹¹ and R ¹² are linked together to form an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of a hydrogen atom, a nitrogen atom and a carbon atom, or an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of a hydrogen atom, an oxygen atom, a nitrogen atom and a carbon atom;
n represents 0 or 1; )

(wherein R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ and R ²² are each independently a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms,
at least one set of R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ , R ¹⁷ and R ¹⁸ , R ¹⁹ and R ²⁰ , and R ²¹ and R ²² is linked to each other to form an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of hydrogen, nitrogen and carbon atoms, or an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of hydrogen, oxygen, nitrogen and carbon atoms; and
* represents a bond. )

[2] The compound according to [1], wherein at least one of R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ in the general formula (I) is a group having a nitro group, a benzoyl group or an o-methylbenzoyl group as a substituent.

（式中、Ｒ^２５、Ｒ^２６、Ｒ^２７、Ｒ^２８及びＲ^２９は、それぞれ独立に、水素原子、シアノ基、ニトロ基、－ＯＲ^３０、－ＣＯＯＲ^３０、－ＣＯ－Ｒ^３０、－ＳＲ^３０、ハロゲン原子、無置換若しくは置換基を有している炭素原子数１～２０の脂肪族炭化水素基、無置換若しくは置換基を有している炭素原子数６～２０の芳香族炭化水素基又は複素環を含有し且つ無置換若しくは置換基を有している炭素原子数２～２０の基又は下記一般式（III）で表される基を表し、
Ｒ^３０は、無置換若しくは置換基を有している炭素原子数１～２０の脂肪族炭化水素基、無置換若しくは置換基を有している炭素原子数６～２０の芳香族炭化水素基又は複素環を含有し且つ無置換若しくは置換基を有している炭素原子数２～２０の基を表し、
Ｒ^２５、Ｒ^２６、Ｒ^２７、Ｒ^２８及びＲ^２９のうち、少なくとも一つが、ニトロ基、－ＣＯ－Ｒ^３０又は下記一般式（III）で表される基を表し、
＊は結合手を表す。）

（式中、Ｒ^３１は、無置換若しくは置換基を有している炭素原子数１～２０の脂肪族炭化水素基又は無置換若しくは置換基を有している炭素原子数６～２０の芳香族炭化水素基を表し、
Ｘ^２は、－ＮＲ^３２Ｒ^３３、下記（ａ’）又は下記（ｂ’）で表される基であり、
Ｒ^３２及びＲ^３３は、それぞれ独立に、水素原子、無置換若しくは置換基を有している炭素原子数１～２０の脂肪族炭化水素基又は無置換若しくは置換基を有している炭素原子数６～２０の芳香族炭化水素基であるか、
Ｒ^３２及びＲ^３３が互いに連結して、無置換若しくは置換基を有し且つ水素原子、窒素原子及び炭素原子からなる炭素原子数１～２０の環、又は無置換若しくは置換基を有し且つ水素原子、酸素原子、窒素原子及び炭素原子からなる炭素原子数１～２０の環を形成しており、
ｍは０又は１を表し、＊は、結合手を表す。）

（式中、Ｒ^３４、Ｒ^３５、Ｒ^３６、Ｒ^３７、Ｒ^３８、Ｒ^３９、Ｒ^４０、Ｒ^４１、Ｒ^４２及びＲ^４３は、それぞれ独立に、水素原子、無置換若しくは置換基を有している炭素原子数１～２０の脂肪族炭化水素基又は無置換若しくは置換基を有している炭素原子数６～２０の芳香族炭化水素基であるか、
Ｒ^３４とＲ^３５、Ｒ^３６とＲ^３７、Ｒ^３８とＲ^３９、Ｒ^４０とＲ^４１及びＲ^４２とＲ^４３のうちの少なくとも一組が互いに連結して、無置換若しくは置換基を有し且つ水素原子、窒素原子及び炭素原子からなる炭素原子数１～２０の環、又は無置換若しくは置換基を有し且つ水素原子、酸素原子、窒素原子及び炭素原子からなる炭素原子数１～２０の環を形成しており、
＊は結合手を表す。）[3] The compound according to [1] or [2], wherein at least one of R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ in general formula (I) is a group represented by general formula (II) below.

(wherein R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ are each independently a hydrogen atom, a cyano group, a nitro group, -OR ³⁰ , -COOR ³⁰ , -CO-R 30 , ^{-SR 30 ,} a halogen atom, an unsubstituted or substituted C 1-20 aliphatic hydrocarbon group, an unsubstituted or substituted C 6-20 an aromatic hydrocarbon group or a group containing a heterocyclic ring and having 2 to 20 carbon atoms which is unsubstituted or substituted, or a group represented by the following general formula (III);
R ³⁰ represents an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or a group containing a heterocyclic ring and having 2 to 20 carbon atoms and being unsubstituted or substituted;
at least one of R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ represents a nitro group, —CO—R ³⁰ or a group represented by the following general formula (III);
* represents a bond. )

(wherein R ³¹ represents an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms or an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms,
X ² is —NR ³² R ³³ , a group represented by (a′) or (b′) below,
R ³² and R ³³ are each independently a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms,
R ³² and R ³³ are linked together to form an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of a hydrogen atom, a nitrogen atom and a carbon atom, or an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of a hydrogen atom, an oxygen atom, a nitrogen atom and a carbon atom;
m represents 0 or 1, * represents a bond. )

(wherein R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ , R ³⁸ , R ³⁹ , R ⁴⁰ , R ⁴¹ , R ⁴² and R ⁴³ are each independently a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms,
at least one of R ³⁴ and R ³⁵ , R ³⁶ and R ³⁷ , R ³⁸ and R ³⁹ , R ⁴⁰ and R ⁴¹ , and R ⁴² and R ⁴³ are linked to each other to form an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of hydrogen, nitrogen and carbon atoms, or an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of hydrogen, oxygen, nitrogen and carbon atoms; and
* represents a bond. )

[4] A latent base generator containing the compound according to any one of [1] to [3].

[5] A polymerization initiator containing the compound according to any one of [1] to [3].

[6] A photosensitive resin composition containing the polymerization initiator (A) according to [5] and a photosensitive resin (B).

[7] The photosensitive resin composition according to [6], wherein the photosensitive resin (B) is an epoxy resin or a phenol resin.

[8] A cured product obtained from the photosensitive resin composition of [6] or [7].

[9] A method for producing a cured product, comprising the step of irradiating the photosensitive resin composition according to [6] or [7] with an energy ray.

Preferred embodiments of the present invention are described in detail below.
The novel compound of the present invention is a carbamoyl oxime compound represented by the above general formula (I). The carbamoyl oxime compound has geometric isomers due to the double bond of the oxime, but the above general formula (I) does not distinguish between them.
That is, in the present specification, the compounds represented by the above general formula (I), and the compounds and exemplary compounds that are preferred forms of the compounds described later represent a mixture or either one of geometric isomers, and are not limited to the isomers of the structures shown.
When the methylene groups in the groups represented by R ¹ to R ⁸ and R ¹¹ to R ²² in general formula (I) are substituted with groups containing carbon atoms, the number including those carbon atoms is the specified number of carbon atoms.

上記一般式（I）中のＲ ^１ ～Ｒ ^８ 、Ｒ ^１１ ～Ｒ ^２２で表される無置換の炭素原子数１～２０の脂肪族炭化水素基としては、例えば、メチル、エチル、プロピル、イソプロピル、ブチル、イソブチル、ｓ－ブチル、ｔ－ブチル、アミル、イソアミル、ｔ－アミル、ヘキシル、ヘプチル、オクチル、イソオクチル、２－エチルヘキシル、ｔ－オクチル、ノニル、イソノニル、デシル、イソデシル、ウンデシル、ドデシル、テトラデシル、ヘキサデシル、オクタデシル、イコシル、シクロペンチル、シクロヘキシル、シクロヘキシルメチル等が挙げられる。 R ¹ to R ⁸ and R ¹¹ to R ²² may be groups in which the methylene groups in these aliphatic hydrocarbon groups are substituted with -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO ₂ -, -NR-, -NR-CO-, -CO-NR-, -NR-COO-, -OCO-NR- or -SiRR'-. However, these substituted divalent groups shall not be adjacent to each other.
R and R' are unsubstituted aliphatic hydrocarbon groups, and examples of the unsubstituted aliphatic hydrocarbon groups include the same groups as those exemplified as the unsubstituted aliphatic hydrocarbon groups having 1 to 20 carbon atoms represented by R ¹ to R ⁸ and R ¹¹ to R ²² above.

Examples of the unsubstituted aromatic hydrocarbon groups having 6 to 20 carbon atoms represented by R ¹ to R ⁸ and R ¹¹ to R ²² in the general formula (I) include phenyl, naphthyl, phenanthryl, pyrenyl and biphenyl, and phenyl, naphthyl, phenanthryl, pyrenyl and biphenyl substituted with an aliphatic hydrocarbon group. In R ¹ to R ⁸ and R ¹¹ to R ²² , the alkylene portion in these aromatic hydrocarbon groups or the methylene group at the bonding portion between the aromatic ring and the aliphatic hydrocarbon group is -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO ₂ -, -NR-, -NR-CO-, -CO-NR-, -NR-COO-, -OCO-NR- Alternatively, it may be a group substituted with -SiRR'-. However, these substituted divalent groups shall not be adjacent to each other.
Examples of the aliphatic hydrocarbon group include groups similar to those exemplified as the unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by R ¹ to R ⁸ and R ¹¹ to R ²² .
R and R' are unsubstituted aliphatic hydrocarbon groups, and examples of the unsubstituted aliphatic hydrocarbon groups include the same groups as those exemplified as the unsubstituted aliphatic hydrocarbon groups having 1 to 20 carbon atoms represented by R ¹ to R ⁸ and R ¹¹ to R ²² above.

As the substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by R ¹ to R ⁸ and R ¹¹ to R ²² and the aromatic hydrocarbon group having 6 to 20 carbon atoms having a substituent represented by R ¹ to R ⁸ and R ¹¹ to R ²² , the unsubstituted hydrogen atom described above may be a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a nitro group, a hydroxyl group or a thiol group. groups, —COOH or —SO ₂ H.

Ｒ ^１１及びＲ ^１２ 、Ｒ ^１３とＲ ^１４ 、Ｒ ^１５とＲ ^１６ 、Ｒ ^１７とＲ ^１８ 、Ｒ ^１９とＲ ^２０及びＲ ^２１とＲ ^２２ 、並びにＲ ^３２とＲ ^３３ 、Ｒ ^３４とＲ ^３５ 、Ｒ ^３６とＲ ^３７ 、Ｒ ^３８とＲ ^３９ 、Ｒ ^４０とＲ ^４１及びＲ ^４２とＲ ^４３のうちの少なくとも一組が互いに連結して形成する、炭素原子数１～２０の水素原子、窒素原子及び炭素原子からなる環としては、結合している窒素原子を含めた基として、ピロール基、ピロリジン基、イミダゾール基、イミダゾリジン基、イミダゾリン基、ピラゾール基、ピラゾリジン基、ピペリジン基、ピペラジン基等が挙げられ、これらの環の水素原子は、フッ素原子、塩素原子、臭素原子、ヨウ素原子、シアノ基、ニトロ基、水酸基、チオール基、－ＣＯＯＨ、－ＳＯ _２ Ｈ又は脂肪族炭化水素基により置換されていてもよい。
Examples of the aliphatic hydrocarbon group include groups similar to those exemplified as the unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by R ¹ to R ⁸ and R ¹¹ to R ²² .

Ｒ ^１１及びＲ ^１２ 、Ｒ ^１３とＲ ^１４ 、Ｒ ^１５とＲ ^１６ 、Ｒ ^１７とＲ ^１８ 、Ｒ ^１９とＲ ^２０及びＲ ^２１とＲ ^２２ 、並びにＲ ^３２とＲ ^３３ 、Ｒ ^３４とＲ ^３５ 、Ｒ ^３６とＲ ^３７ 、Ｒ ^３８とＲ ^３９ 、Ｒ ^４０とＲ ^４１及びＲ ^４２とＲ ^４３のうちの少なくとも一組が互いに連結して形成する、炭素原子数１～２０の水素原子、酸素原子、窒素原子及び炭素原子からなる環としては、結合している窒素原子を含めた基として、モルホリン基、オキサゾール基、オキサゾリン基、オキサジアゾール基等が挙げられ、これらの環の水素原子は、フッ素原子、塩素原子、臭素原子、ヨウ素原子、シアノ基、ニトロ基、水酸基、チオール基、－ＣＯＯＨ、－ＳＯ _２ Ｈ又は脂肪族炭化水素基により置換されていてもよい。
Examples of the aliphatic hydrocarbon group include groups similar to those exemplified as the unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by R ¹ to R ⁸ and R ¹¹ to R ²² .

上記一般式（I）中の、Ｒ ^２ ～Ｒ ^８で表される無置換の炭素原子数２～２０の複素環を含有する基としては、テトラヒドロフラン基、ジオキソラニル基、テトラヒドロピラニル基、モルホリルフラン基、チオフェン基、メチルチオフェン基、ヘキシルチオフェン基、ベンゾチオフェン基、ピロール基、ピロリジン基、イミダゾール基、イミダゾリジン基、イミダゾリン基、ピラゾール基、ピラゾリジン基、ピペリジン基及びピペラジン基、並びに脂肪族炭化水素基で置換されたテトラヒドロフラン基、ジオキソラニル基、テトラヒドロピラニル基、モルホリルフラン基、チオフェン基、メチルチオフェン基、ヘキシルチオフェン基、ベンゾチオフェン基、ピロール基、ピロリジン基、イミダゾール基、イミダゾリジン基、ピラゾール基、ピラゾリジン基、ピペリジン基及びピペラジン基等が挙げられる。 R ² to R ⁸ may be groups in which the alkylene moiety in these heterocyclic-containing groups and the methylene group at the junction between the heterocyclic ring and the alkyl group are substituted with -O-, -COO-, -OCO-, -CO-, -CS-, -S-, -SO-, -SO ₂ -, -NR-, -NR-CO-, -CO-NR-, -NR-COO-, -OCO-NR- or -SiRR'-. Good. However, these substituted divalent groups shall not be adjacent to each other.
In the present specification, "2 to 20" in the "heterocyclic ring-containing group having 2 to 20 carbon atoms" defines the number of carbon atoms in the "heterocyclic ring-containing group" rather than the "heterocyclic ring".
Examples of the aliphatic hydrocarbon group include those exemplified as the unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by R ¹ to R ⁸ and R ¹¹ to R ²² above.
R and R' are unsubstituted aliphatic hydrocarbon groups, and examples of the unsubstituted aliphatic hydrocarbon groups include the same groups as those exemplified as the unsubstituted aliphatic hydrocarbon groups having 1 to 20 carbon atoms represented by R ¹ to R ⁸ and R ¹¹ to R ²² above.

Examples of the group containing a heterocyclic ring having 2 to 20 carbon atoms and having a substituent represented by R ² to R ⁸ include those in which the hydrogen atom of the unsubstituted heterocyclic ring-containing group described above is substituted with a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, —COOH, or —SO ₂ H. In addition, when the group to be substituted contains a carbon atom, and when it has a substituent, the number including the number of carbon atoms becomes the specified number of carbon atoms.

上記一般式（I）で表される新規化合物としては、感光性樹脂組成物に用いた場合、ＵＶ感度、硬化性に優れる点から、Ｘ ^１が、－ＮＲ ^１１ Ｒ ^１２で表される基であり、Ｒ ^１１又はＲ ^１２がフェニル基である化合物、Ｒ ^１１及びＲ ^１２が炭素原子数１～２０の脂肪族炭化水素基である化合物、Ｒ ^１１及びＲ ^１２が互いに連結して水素原子、窒素原子及び炭素原子からなる炭素原子数１～２０の環を形成している化合物、又はＲ ^１１及びＲ ^１２が互いに連結して水素原子、酸素原子、窒素原子及び炭素原子からなる炭素原子数１～２０の環を形成している化合物が好ましい。
Further, from the viewpoint of excellent UV sensitivity, longer absorption wavelength, and excellent solubility in resins, compounds in which at least one of R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ is a nitro group, a cyano group, a hydroxyl group, a carboxyl group or a thiol group, or a group having these groups as a substituent are preferred, and compounds having a nitro group or a group having a nitro group as a substituent are more preferred, and particularly R ³ is a nitro group. A compound having as a substituent is preferred. A nitrophenyl group is preferred as the group having a nitro group as a substituent.
Further, from the viewpoint of excellent sensitivity when used as a polymerization initiator, compounds in which at least one of R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ is a benzoyl group, an o-methylbenzoyl group or a trifluoromethyl group, or groups having these groups as substituents are also preferred, and compounds in which R ³ is a group having a benzoyl group as a substituent are particularly preferred. A benzoylphenyl group is preferable as the group having a benzoyl group as a substituent.
A compound in which at least one of R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ in the general formula (I) is a group having a nitro group, a benzoyl group or an o-methylbenzoyl group as a substituent is preferable because the absorption wavelength range is lengthened (365 nm) and the sensitivity is excellent when used as a polymerization initiator.

In the present invention, the following compounds are preferable because they are excellent in UV sensitivity and curability when used in the photosensitive resin composition, and excellent in sensitivity when used as a polymerization initiator.
上記一般式（I）において、Ｒ ^１が炭素原子数１～２０の脂肪族炭化水素基であり、Ｒ ^２ 、Ｒ ^４ 、Ｒ ^５ 、Ｒ ^６及びＲ ^７が水素原子であり、Ｘ ^１が、－ＮＲ ^１１ Ｒ ^１２で表される基であり且つＲ ^１１及びＲ ^１２が炭素原子数１～２０の脂肪族炭化水素基であるか、又はＲ ^１１及びＲ ^１２が互いに連結して水素原子、窒素原子及び炭素原子からなる炭素原子数１～２０の環、若しくは水素原子、酸素原子、窒素原子及び炭素原子からなる炭素原子数１～２０の環を形成しており、Ｒ ^３が、ニトロ基又はベンゾイル基を置換基として有している基である化合物。

A compound in which at least one of R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ in the general formula (I) is a group represented by the general formula (II) has a longer absorption wavelength range (365 nm), and is excellent in sensitivity when used as a polymerization initiator.
In general formula (II), the unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms and the aromatic hydrocarbon group having 6 to 20 carbon atoms represented by R ²⁵ to R ⁴³ are the same as those exemplified as the unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms and the unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms represented by R ¹ to R ⁸ and R ¹¹ to R ²² . The same group is mentioned respectively.
In general formula (II), the group containing an unsubstituted or substituted heterocyclic ring having 2 to 20 carbon atoms represented by R ²⁵ to R ³⁰ includes the same groups as the groups containing an unsubstituted or substituted heterocyclic ring having 2 to 20 carbon atoms represented by R ² to R ⁸ above.

A compound in which one of R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ in the above general formula (I) is a group represented by the above general formula (II) and the others are a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 6 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon group having 6 to 12 carbon atoms, is preferred in terms of excellent sensitivity and ease of production.

A compound in which R ¹ in the general formula (I) is an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 12 carbon atoms or an unsubstituted or substituted aromatic hydrocarbon group having 6 to 12 carbon atoms is preferable in terms of ease of production.

A compound in which n in the general formula (I) is 0 is preferable because of its excellent sensitivity when used as a polymerization initiator.

A compound in which n is 1 in the above general formula (I) is preferable because, when used as a polymerization initiator, a cured product having excellent transparency can be obtained.

Among the novel compounds represented by the above general formula (I), specific examples of compounds in which n is 0 include the following compound Nos. 1 to No. 74 can be mentioned. However, the present invention is not limited by the following compounds.

Among the novel compounds represented by the above general formula (I), specific examples of compounds in which n is 1 include the following compound Nos. 75 to No. 152 are mentioned. However, the present invention is not limited by the following compounds.

The carbamoyl oxime compound of the present invention represented by the general formula (I) is not particularly limited, but when n=0, it can be produced by the following method according to Reaction Scheme 1 below.
That is, an indole compound 2 is obtained by reacting a known and commercially available indole compound 1 with an aryl halide or an alkyl halide compound. A ketone compound is obtained by reacting this indole compound 2 with an acid chloride, and an oxime compound is obtained by reacting the ketone compound with hydroxylamine hydrochloride. Subsequently, the oxime compound is reacted with 4-nitrophenyl chloroformate and a primary or secondary amine in the presence of triethylamine to obtain the carbamoyl oxime compound of the present invention represented by the general formula (I).
Although the reaction formula 1 below shows the case where X ¹ is —NR ¹¹ R ¹² , compounds in which X ¹ is a group represented by (a) or (b) above can also be produced by changing the amine to be used.
Oxime compounds and carbamoyl oxime compounds can also be produced by the method described in Japanese Patent No. 4,223,071.

（式中、Ｒ^１～Ｒ^１２は、上記一般式（I）と同じである。）Reaction formula 1

(In the formula, R ¹ to R ¹² are the same as in general formula (I) above.)

In addition, the compound in which n=1 in the above general formula (I) is not particularly limited, but can be produced according to Reaction Scheme 2 below by the following method.
That is, the ketone compound 2 is obtained by reacting the indole compound 2 with an acid chloride, and the oxime compound 2 is obtained by reacting the ketone compound with isobutyl nitrite. Subsequently, the oxime compound 2 is reacted with 4-nitrophenyl chloroformate and a primary or secondary amine in the presence of triethylamine to obtain the carbamoyl oxime compound 2 of the present invention represented by the general formula (I).
Although the reaction formula 2 below shows the case where X ¹ is —NR ¹¹ R ¹² , compounds in which X ¹ is a group represented by (a) or (b) above can also be produced by changing the amine used.
Oxime compounds and carbamoyl oxime compounds can also be produced by the method described in Japanese Patent No. 4,223,071.

（式中、Ｒ^１～Ｒ^１２は、上記一般式（I）と同じである。）Reaction formula 2

(In the formula, R ¹ to R ¹² are the same as in general formula (I) above.)

The novel compound of the present invention can be suitably used as a polymerization initiator that is a photobase generator described below because of its excellent curability of photosensitive resins and its high sensitivity to energy rays, and can also be used for chemically amplified resists.

Next, the polymerization initiator, latent base generator and photosensitive resin composition of the present invention will be described. Note that the description of the novel compound of the present invention applies appropriately to points that are not particularly described.

<Latent base generator>
The latent base generator of the present invention contains at least one compound represented by the general formula (I). The content of the compound represented by the general formula (I) in the polymerization initiator is preferably 1 to 100% by mass, more preferably 50 to 100% by mass.
A latent base generator is one that generates a base by light or heat, and can be used as a polymerization initiator, a base catalyst, and a pH adjuster. In the present invention, a latent photobase generator that generates a base upon irradiation with light is more preferable because of its excellent operability.

<Polymerization initiator (A)>
In the polymerization initiator of the present invention and the photosensitive resin composition of the present invention, the polymerization initiator (A) contains at least one compound represented by the general formula (I). The content of the compound represented by the general formula (I) in the polymerization initiator is preferably 1 to 100% by mass, more preferably 50 to 100% by mass.
In the photosensitive resin composition of the present invention, the content of the polymerization initiator (A) is preferably 1 to 20 parts by mass, more preferably 1 to 10 parts by mass with respect to 100 parts by mass of the photosensitive resin (B). When the content of the polymerization initiator (A) is 1 part by mass or more, it is preferable because it is easy to prevent poor curing due to insufficient sensitivity.

<Photosensitive resin (B)>
The photosensitive resin (B) used in the present invention is a resin whose curing temperature is lowered using an anionically polymerizable functional group or a base as a catalyst, and is a photosensitive resin that is polymerized and cured by irradiation with energy rays such as ultraviolet rays or a curable resin whose curing temperature is lowered. The anionic polymerizable functional group means a functional group that can be polymerized by a base generated from a photobase generator by an active energy ray such as ultraviolet rays, and examples thereof include an epoxy group, an episulfide group, a cyclic monomer (δ-valerolactone, ε-caprolactam), a catalyst for forming a urethane bond with an isocyanate and an alcohol, a Michael addition catalyst for a (meth)acrylic group, a catalyst for a crosslinking reaction of a silicone resin, and the like. Examples of the photosensitive resin (B) include epoxy resins, phenol resins, polyamide resins, polyurethane resins, nylon resins, polyester resins, and silicone resins. These resins may be used alone or in combination of two or more. Among them, a combination of an epoxy resin and a phenol resin is preferable because the reaction progresses quickly and the adhesiveness is good.

Examples of the epoxy resin include polyglycidyl ether compounds of mononuclear polyhydric phenol compounds such as hydroquinone, resorcinol, pyrocatechol, and phloroglucinol; Polyglycidyl ethers of polynuclear polyhydric phenol compounds such as bis(4-hydroxycumylbenzene), 1,4-bis(4-hydroxycumylbenzene), 1,1,3-tris(4-hydroxyphenyl)butane, 1,1,2,2-tetra(4-hydroxyphenyl)ethane, thiobisphenol, sulfobisphenol, oxybisphenol, phenol novolak, orthocresol novolak, ethylphenol novolak, butylphenol novolak, octylphenol novolak, resorcinol novolak, and terpene phenol Compound; polyglycidyl ether of polyhydric alcohols such as ethylene glycol, propylene glycol, butylene glycol, hexanediol, polyglycol, thiodiglycol, glycerin, trimethylolpropane, pentaerythritol, sorbitol, bisphenol A-ethylene oxide adduct; Glycidyl esters of aliphatic, aromatic or alicyclic polybasic acids such as terephthalic acid, trimellitic acid, trimesic acid, pyromellitic acid, tetrahydrophthalic acid, hexahydrophthalic acid and endomethylenetetrahydrophthalic acid, and homopolymers or copolymers of glycidyl methacrylate; epoxides of cyclic olefin compounds such as vinylcyclohexene diepoxide, dicyclopentanediene diepoxide, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-6-methylcyclohexylmethyl-6-methylcyclohexanecarboxylate, bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate; epoxidized polybutadiene, epoxidized acrylonitrile-butadiene copolymer, epoxy Examples include epoxidized conjugated diene polymers such as styrene-butadiene copolymers, and heterocyclic compounds such as triglycidyl isocyanurate. In addition, these epoxy resins may be internally crosslinked with prepolymers having terminal isocyanates or may be polymerized with polyvalent active hydrogen compounds (polyhydric phenols, polyamines, carbonyl group-containing compounds, polyphosphate esters, etc.).
Among the above epoxy resins, those having a glycidyl group are preferable, and those having a bifunctional or more glycidyl group are more preferable from the viewpoint of excellent curability.

As the phenol resin, a phenol resin having two or more hydroxy groups in one molecule is preferable, and generally known phenol resins can be used. Examples of phenolic resins include bisphenol A type phenolic resin, bisphenol E type phenolic resin, bisphenol F type phenolic resin, bisphenol S type phenolic resin, phenolic novolac resin, bisphenol A novolac type phenolic resin, glycidyl ester type phenolic resin, aralkyl novolac type phenolic resin, biphenylaralkyl type phenolic resin, cresol novolac type phenolic resin, polyfunctional phenolic resin, naphthol resin, naphthol novolak resin, polyfunctional naphthol resin, anthracene type phenolic resin, and naphthalene skeleton-modified novolak. type phenol resins, phenol aralkyl-type phenol resins, naphthol aralkyl-type phenol resins, dicyclopentadiene-type phenol resins, biphenyl-type phenol resins, alicyclic phenol resins, polyol-type phenol resins, phosphorus-containing phenol resins, polymerizable unsaturated hydrocarbon group-containing phenol resins, and hydroxyl group-containing silicone resins, but are not particularly limited. These phenol resins can be used singly or in combination of two or more.

As the polyamide resin, the acid dianhydride is ethylenetetracarboxylic dianhydride, 1,2,3,4-benzenetetracarboxylic dianhydride, 1,2,3,4-cyclohexanetetracarboxylic dianhydride, 2,2',3,3'-benzophenonetetracarboxylic dianhydride, 2,2,3,3-biphenyltetracarboxylic dianhydride, 1,4,5,8-naphthalenetetracarboxylic dianhydride, and the diamine is (o-, m- or p-). Examples thereof include resins made from phenylenediamine, (3,3'- or 4,4'-)diaminodiphenyl ether, diaminobenzophenone, (3,3'- or 4,4'-)diaminodiphenylmethane, and the like.

Examples of the polyurethane resin include polyfunctional isocyanates such as tolylene diisocyanate, hexamethylene diisocyanate, diphenylmethane diisocyanate, and isophorone diisocyanate, and polyols such as polyether polyols, polyester polyols, and polycarbonate polyols (polyfunctional alcohols) as raw materials.
Examples of the nylon resin include resins made from cyclic monomers such as ε-caprolactam and lauryllactam.
Examples of the polyester resin include resins made from cyclic monomers such as δ-valerolactone and β-propiolactone.
Examples of the silicone resin include methyl silicone resin, methyl/phenyl silicone resin, and organic resin-modified silicone resin.

<Additive>
Additives such as inorganic compounds, colorants, latent epoxy curing agents, chain transfer agents, sensitizers and solvents can be used as optional components in the photosensitive resin composition of the present invention.

Examples of the inorganic compounds include metal oxides such as nickel oxide, iron oxide, iridium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, potassium oxide, silica, and alumina; Copper etc. are mentioned. These inorganic compounds are used as, for example, fillers, antireflection agents, conductive materials, stabilizers, flame retardants, mechanical strength improvers, special wavelength absorbers, ink generating agents, and the like.

Examples of the coloring material include pigments, dyes, and natural pigments. These coloring materials can be used alone or in combination of two or more.

Examples of the above pigments include nitroso compounds; nitro compounds; azo compounds; diazo compounds; xanthene compounds; quinoline compounds; anthraquinone compounds; coumarin compounds; Metal complex compound of dye; lake pigment; carbon black obtained by furnace method, channel method or thermal method, or carbon black such as acetylene black, ketjen black or lamp black; carbon black prepared or coated with epoxy resin; Black, carbon black in which the total oxygen content calculated from CO and CO2 in the volatile matter at 950°C is 9 mg or more per 100 m2 of surface area; graphite, graphitized carbon black, activated carbon, carbon fiber, carbon nanotube, carbon microcoil, carbon nanohorn, carbon aerogel, fullerene; aniline black, pigment black 7, titanium black; , pyridian, emerald green, lead sulfate, yellow lead, zinc yellow, red iron oxide (red iron oxide (III)), cadmium red, synthetic iron black, amber, and other organic or inorganic pigments can be used. These pigments can be used alone or in combination.

Commercially available pigments can also be used as the above pigments. , 184, 185, 192, 200, 202, 209, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, 254; Pigment Yellow 1, 3, 12, 13, 14, 16, 17, 20, 24, 55, 60, 73, 81, 83, 86, 93, 95, 97, 98, 100, 109, 110, 113, 114, 117, 120, 125, 126, 127, 129, 137, 138, 139, 1 Pigment Green 7, 10, 36; Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:5, 15:6, 22, 24, 56, 60, 61, 62, 64; Pigment Bio Rhett 1, 19, 23, 27, 29, 30, 32, 37, 40, 50 and the like.

Examples of the dyes include azo dyes, anthraquinone dyes, indigoid dyes, triarylmethane dyes, xanthene dyes, alizarin dyes, acridine dyes stilbene dyes, thiazole dyes, naphthol dyes, quinoline dyes, nitro dyes, indamine dyes, oxazine dyes, phthalocyanine dyes, cyanine dyes, and the like.

Examples of the latent epoxy curing agent include dicyandiamide, modified polyamines, hydrazides, 4,4'-diaminodiphenylsulfone, boron trifluoride amine complex salts, imidazoles, guanamines, imidazoles, ureas and melamine.

A sulfur atom-containing compound is generally used as the chain transfer agent or sensitizer. For example, thioglycolic acid, thiomalic acid, thiosalicylic acid, 2-mercaptopropionic acid, 3-mercaptopropionic acid, 3-mercaptobutyric acid, N-(2-mercaptopropionyl)glycine, 2-mercaptonicotinic acid, 3-[N-(2-mercaptoethyl)carbamoyl]propionic acid, 3-[N-(2-mercaptoethyl)amino]propionic acid, N-(3-mercaptopropio Nyl)alanine, 2-mercaptoethanesulfonic acid, 3-mercaptopropanesulfonic acid, 4-mercaptobutanesulfonic acid, dodecyl(4-methylthio)phenyl ether, 2-mercaptoethanol, 3-mercapto-1,2-propanediol, 1-mercapto-2-propanol, 3-mercapto-2-butanol, mercaptophenol, 2-mercaptoethylamine, 2-mercaptoimidazole, 2-mercaptobenzimidazole mercapto compounds such as sol, 2-mercapto-3-pyridinol, 2-mercaptobenzothiazole, mercaptoacetic acid, trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptopropionate), disulfide compounds obtained by oxidation of the mercapto compounds, iodoacetic acid, iodopropionic acid, 2-iodoethanol, 2-iodoethanesulfonic acid, 3-iodopropanesulfonic acid Iodinated alkyl compounds such as acids, trimethylolpropane tris(3-mercaptoisobutyrate), butanediol bis(3-mercaptoisobutyrate), hexanedithiol, decanedithiol, 1,4-dimethylmercaptobenzene, butanediol bisthiopropionate, butanediol bisthioglycolate, ethylene glycol bisthioglycolate, trimethylolpropane tristhioglycolate, butanediol bisthiopropionate, trimethyl propane tristhiopropionate, trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakisthioglycolate, trishydroxyethyl tristhiopropionate, diethylthioxanthone, diisopropylthioxanthone, compound no. Aliphatic polyfunctional thiol compounds such as C1 and trimercaptopropionate tris(2-hydroxyethyl)isocyanurate, Showa Denko Karenz MT BD1, PE1, NR1 and the like.

Examples of the solvent include solvents capable of dissolving or dispersing the components (polymerization initiator (A), photosensitive resin (B), etc.), such as ketones such as methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, and 2-heptanone; Ester solvents such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, and texanol; cellosolve solvents such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; alcohol solvents such as methanol, ethanol, iso- or n-propanol, iso- or n-butanol and amyl alcohol; Ether ester solvents such as methyl ether-2-acetate, dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate and ethoxyethyl propionate; BTX solvents such as benzene, toluene and xylene; Aliphatic hydrocarbon solvents such as hexane, heptane, octane and cyclohexane; Terpene hydrocarbon oils such as turpentine oil, D-limonene and pinene; )), paraffin solvents such as Solvesso #100 (Exxon Chemical Co., Ltd.); halogenated aliphatic hydrocarbon solvents such as carbon tetrachloride, chloroform, trichlorethylene, methylene chloride and 1,2-dichloroethane; halogenated aromatic hydrocarbon solvents such as chlorobenzene; carbitol solvents; dimethyl sulfoxide; water and the like can be used, and these solvents can be used alone or as a mixed solvent of two or more.
Among these, ketones or ether ester solvents, particularly propylene glycol-1-monomethyl ether-2-acetate or cyclohexanone, are preferably used from the standpoints of alkali developability, patterning properties, film forming properties, and solubility.
In the photosensitive resin composition of the present invention, the content of the solvent is not particularly limited, and each component is uniformly dispersed or dissolved, and the photosensitive resin composition of the present invention may be in an amount that exhibits a liquid or paste state suitable for each application. Usually, it is preferable to contain the solvent in a range where the solid content (all components other than the solvent) in the photosensitive resin composition of the present invention is 10 to 90% by mass.

Moreover, the photosensitive resin composition of the present invention can improve the properties of the cured product by using an organic polymer. Examples of the organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, poly(meth)acrylic acid, styrene-(meth)acrylic acid copolymer, (meth)acrylic acid-methyl methacrylate copolymer, ethylene-vinyl chloride copolymer, ethylene-vinyl copolymer, polyvinyl chloride resin, ABS resin, nylon 6, nylon 66, nylon 12, urethane resin, polycarbonate polyvinyl butyral, cellulose ester, polyacrylamide, saturated polyester, phenolic resin, pheno epoxy resin and the like.
When the above organic polymer is used, the amount used is preferably 10 to 500 parts by mass with respect to 100 parts by mass of the photosensitive resin (B).

Surfactants, silane coupling agents, melamine compounds and the like can be used in combination with the photosensitive resin composition of the present invention.

Examples of the surfactant include fluorine-based surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates; anionic surfactants such as higher fatty acid alkali salts, alkylsulfonates and alkyl sulfates; cationic surfactants such as higher amine halides and quaternary ammonium salts; nonionic surfactants such as polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters and fatty acid monoglycerides; .

As the silane coupling agent, for example, silane coupling agents manufactured by Shin-Etsu Chemical Co., Ltd. can be used. Among them, silane coupling agents having an isocyanate group, a methacryloyl group, or an epoxy group such as KBE-9007, KBM-502, and KBE-403 are preferably used.

Examples of the melamine compound include compounds in which all or part (at least two) of active methylol groups (CH ₂ OH groups) in nitrogen compounds such as (poly)methylolmelamine, (poly)methylolglycoluril, (poly)methylolbenzoguanamine, and (poly)methylolurea are alkyl-etherified.
Here, the alkyl group constituting the alkyl ether includes a methyl group, an ethyl group and a butyl group, which may be the same or different. In addition, methylol groups that are not alkyl-etherified may be self-condensed within one molecule, or may be condensed between two molecules to form an oligomer component.
Specifically, hexamethoxymethylmelamine, hexabutoxymethylmelamine, tetramethoxymethylglycoluril, tetrabutoxymethylglycoluril and the like can be used.
Among these, alkyl-etherified melamine such as hexamethoxymethylmelamine and hexabutoxymethylmelamine are preferable in terms of solubility in solvents and resistance to crystal precipitation from the photosensitive resin composition.

In the photosensitive resin composition of the present invention, the amount of optional components other than (A) the polymerization initiator and the photosensitive resin (B) (excluding inorganic compounds, coloring materials, and solvents) is appropriately selected depending on the purpose of use and is not particularly limited, but is preferably 50 parts by weight or less in total with respect to 100 parts by weight of the photosensitive resin (B).

The photosensitive resin composition of the present invention can be cured by irradiation with energy rays. The cured product is formed into an appropriate shape according to the application. For example, when forming a film-like cured product, the photosensitive resin composition of the present invention can be applied onto a supporting substrate such as soda glass, quartz glass, semiconductor substrate, metal, paper, plastic, etc. by known means such as spin coater, roll coater, bar coater, die coater, curtain coater, various types of printing, and immersion. In addition, once applied onto a supporting substrate such as a film, it can be transferred onto another supporting substrate, and there are no restrictions on the method of application.

As the light source of the energy rays used for curing the photosensitive resin composition of the present invention, there are high-energy rays such as electromagnetic waves having a wavelength of 2000 angstroms to 7000 angstroms obtained from ultra-high pressure mercury lamps, high pressure mercury lamps, medium pressure mercury lamps, low pressure mercury lamps, mercury vapor arc lamps, xenon arc lamps, carbon arc lamps, metal halide lamps, fluorescent lamps, tungsten lamps, excimer lamps, germicidal lamps, light emitting diodes, CRT light sources, and high energy rays such as electron beams, X-rays and radiation. can be used, but an ultra-high pressure mercury lamp, mercury vapor arc lamp, carbon arc lamp, xenon arc lamp or the like that emits light with a wavelength of 300 to 450 nm is preferably used.

Furthermore, by using a laser beam as an exposure light source, a laser direct writing method in which an image is formed directly from digital information such as a computer without using a mask is useful because it can improve not only productivity but also resolution, positional accuracy, etc. As the laser beam, light with a wavelength of 340 to 430 nm is preferably used, but excimer laser, nitrogen laser, argon ion laser, helium cadmium laser, helium neon laser, krypton ion laser, various semiconductor lasers and YAG lasers. It is also possible to use one that emits light in the visible to infrared region, such as. When using these laser beams, a sensitizing dye that absorbs in the visible to infrared region is preferably added.

In order to cure the photosensitive resin composition of the present invention, it is usually necessary to heat after irradiation with the energy beam, and heating at about 40 to 150° C. is preferable in terms of curing rate.

The photosensitive resin composition of the present invention is a photocurable paint or varnish; a photocurable adhesive; a coating agent for metals; a printed circuit board; or for forming their structures in the manufacturing process of plasma display panels, electroluminescent displays, and LCDs; compositions for encapsulating electrical and electronic components; solder resists; decolorizing materials for image recording materials using microcapsules; photoresist materials for printed wiring boards; photoresist materials for UV and visible laser direct imaging systems;

The photosensitive resin composition of the present invention can also be used for the purpose of forming spacers for liquid crystal display panels and for the purpose of forming projections for vertically aligned liquid crystal display elements. In particular, it is useful as a photosensitive resin composition for simultaneously forming projections and spacers for vertically aligned liquid crystal display devices.

The spacer for a liquid crystal display panel is preferably formed by (1) a step of forming a coating film of the photosensitive resin composition of the present invention on a substrate, (2) a step of irradiating the coating film with energy rays (light) through a mask having a predetermined pattern shape, (3) a baking step after exposure, (4) a step of developing the coating after exposure, and (5) a step of heating the coating after development.

The photosensitive resin composition of the present invention to which a coloring material is added is suitably used as a resist forming each pixel such as RGB in a color filter, or as a black matrix resist forming partition walls of each pixel. Furthermore, in the case of a black matrix resist to which an ink-repellent agent is added, it is preferably used for partition walls for ink-jet type color filters having a profile angle of 50° or more. As the ink repellent agent, a fluorosurfactant and a composition containing the fluorosurfactant are preferably used.

When used as partition walls for an ink-jet type color filter, the partition walls formed from the photosensitive resin composition of the present invention partition the surface of the transfer material, and droplets are applied to the partitioned recesses on the transfer material by an ink-jet method to form an image area. At this time, it is preferable that the droplet contains a coloring agent and the image area is colored. In this case, the optical element manufactured by the above manufacturing method has at least a pixel group consisting of a plurality of colored areas on the substrate and partition walls separating the colored areas of the pixel group.

The photosensitive resin composition of the present invention can also be used as a composition for protective films or insulating films. In this case, an ultraviolet absorber, an alkylated modified melamine and/or an acrylic modified melamine, a mono- or bifunctional (meth)acrylate monomer containing an alcoholic hydroxyl group in the molecule, and/or silica sol can be contained.

The insulating film is used for the insulating resin layer in a laminate in which an insulating resin layer is provided on a peelable supporting base material, the laminate can be developed with an alkaline aqueous solution, and the thickness of the insulating resin layer is preferably 10 to 100 μm.

The photosensitive resin composition of the present invention can be used as a photosensitive paste composition by containing an inorganic compound. The photosensitive paste composition can be used to form fired patterns such as barrier rib patterns, dielectric patterns, electrode patterns and black matrix patterns of plasma display panels.

EXAMPLES The present invention will be described in more detail below with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples and the like.

[Production Example 1] Synthesis of Oxime Form 1 <Step 1>
1.0 eq. of indole was added to a 200 mL four-necked flask. , 4-fluoronitrobenzene 1.2 eq. , potassium carbonate 3.0 eq. and N,N-dimethylformamide (500% by weight of the theoretical yield) were added, and the mixture was heated and stirred at 130° C. for 3 hours under nitrogen flow at 20 mL/min. After cooling to room temperature, 50 g of ion-exchanged water was added and stirred for 1 hour. After the precipitate was collected by filtration, it was dried under reduced pressure at 50° C. to a constant weight to obtain N-nitrophenylindole with a yield of 85%.
<Step 2>
1.0 eq. , aluminum chloride 2.5 eq. and dichloroethane (500% by weight of the theoretical yield) were added and stirred at 5° C. on an ice bath. Myristoyl chloride 1.3 eq. was added dropwise. After raising the temperature to room temperature, the mixture was stirred for 3 hours, and 50 g of ion-exchanged water was added to separate the organic layer. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off and ethanol was added for crystallization. The crystals obtained by filtration were dried under reduced pressure at 50° C. to a constant weight to obtain ketone compound 1 with a yield of 65%.
<Step 3>
1.0 eq. , hydroxylamine hydrochloride 2.0 eq. and pyridine (200% by weight of the theoretical yield) were added, and the mixture was heated and stirred at 95° C. for 2.5 hours under nitrogen flow at 20 mL/min. After cooling to room temperature, 50 g of ion-exchanged water was added to separate the organic layer. After the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off and the residue was dried under reduced pressure at 50° C. to a constant weight to obtain the oxime compound 1 with a yield of 88%.

[Production Example 2] Synthesis of Oxime 2 Oxime 2 was obtained with an overall yield of 11% in the same manner as in Production Example 1 except that 4-fluorobenzophenone was used in place of 4-fluoronitrobenzene in <Step 1> and n-octanoyl chloride was used in place of myristoyl chloride in Step 2.

[Example 1] Compound no. Synthesis of 1 1.0 eq. , dichloromethane (500% by weight of theoretical yield) and 2.0 eq. was added and stirred at 5°C on an ice bath. 1.1 eq. of 4-nitrophenyl chloroformate was added thereto. was added dropwise in dichloromethane. After completion of dropping, the mixture was stirred at room temperature for 30 minutes. After cooling to 5° C. again on an ice bath, 1.1 eq. was added dropwise. The mixture was stirred at room temperature for 3 hours, and the solvent was distilled off under reduced pressure. Ethyl acetate and 5% by mass NaOH aqueous solution were added thereto to separate the organic layer. The organic layer was washed with ion-exchanged water three times and then concentrated. Crystallization was carried out by adding methanol to the residue, and compound No. 2 was obtained. 1 was obtained as a yellow powdery compound in a yield of 70%. The obtained solid was analyzed by TG-DTA (melting point/° C.) and ¹ H-NMR. The results are shown in [Table 1] and [Table 2].

[Example 2] Compound no. Synthesis of Compound No. 2 The procedure of Example 1 was repeated except that oxime body 1 described in Example 1 was changed to oxime body 2. 2 was obtained in 54% yield. The obtained solid was analyzed by TG-DTA (melting point/° C.) and ¹ H-NMR. The results are shown in [Table 1] and [Table 2].

[Production Example 3] Synthesis of oxime derivative 3 A ketone compound 2 was obtained in the same manner as in Production Example 1 except that 4-fluoronitrobenzene in <Step 1> was changed to 4-fluorobenzophenone and myristoyl chloride in <Step 2> was changed to n-octanoyl chloride.
<Step 3>
1.0 eq. , DMF (300% by weight of theoretical yield), hydrochloric acid 1.2 eq. and stirred at 5°C on an ice bath. 1.2 eq. isobutyl nitrite was added thereto. was added dropwise. After heating to room temperature, the mixture was stirred for 6 hours. After that, 50 g of ion-exchanged water and ethyl acetate were added to separate the organic layer. The organic layer was washed with water three times and concentrated under reduced pressure using an evaporator to obtain the oxime compound 3. The obtained oxime derivative 3 was used for the next reaction without purification.

[Example 3] Compound no. Synthesis of 75 A 100 ml four-necked flask was flushed with nitrogen, and 1.0 eq. , dichloromethane (500% by weight of theoretical yield) and 2.0 eq. was added and stirred at 5°C on an ice bath. 1.1 eq. of 4-nitrophenyl chloroformate was added thereto. was added dropwise in dichloromethane. After completion of dropping, the mixture was stirred at room temperature for 30 minutes. After cooling to 5° C. again on an ice bath, piperidine 1.1 eq. was added dropwise. After stirring at room temperature for 5 hours, the solvent was distilled off under reduced pressure. Ethyl acetate and 5 mass % NaOH aqueous solution were added thereto, and the organic layer was separated. The organic layer was washed with ion-exchanged water three times and then concentrated. Crystallization was carried out by adding methanol to the residue, and compound No. 2 was obtained. 75 was obtained as a yellow powdery compound in a yield of 30%. The obtained solid was analyzed by TG-DTA (melting point/° C.) and ¹ H-NMR. The results are shown in [Table 1] and [Table 2].

[Example 4] Compound no. Synthesis of Compound No. 76 The procedure of Example 3 was repeated except that piperidine described in Example 3 was changed to morpholine. 76 was obtained in 51% yield. The obtained solid was analyzed by TG-DTA (melting point/° C.) and ¹ H-NMR. The results are shown in [Table 1] and [Table 2].

[Example 5] Compound no. Synthesis of 77 Piperidine 1.1 eq. the piperazine 0.50 eq. The same operation as in Example 3 was performed except that the compound No. 77 was obtained in 43% yield. The obtained solid was analyzed by TG-DTA (melting point/° C.) and ¹ H-NMR. The results are shown in [Table 1] and [Table 2].

[Example 6] Compound no. Synthesis of Compound No. 152 The procedure of Example 3 was repeated except that dibutylamine was used instead of piperidine. 152 was obtained in 38% yield. The obtained solid was analyzed by TG-DTA (melting point/° C.) and ¹ H-NMR. The results are shown in [Table 1] and [Table 2].

[Comparative Example 1] The following comparative compound No. 1 was used.

[Evaluation Examples 1 to 5 and Comparative Evaluation Example 1] Evaluation of optical resolution Compound No. 1, No. 75, No. 76, No. 77, No. 152 and the following comparative compound Nos. 1 was adjusted to 1.0×10 ⁻⁴ mol of acetonitrile solution and placed in a quartz cell with a lid. The sample was irradiated with ultraviolet light from an ultra-high pressure mercury lamp under the conditions of 100 mJ/cm ² , 500 mJ/cm ² and 1000 mJ/cm ² (accumulated light quantity at 365 nm) to examine the decomposability. For the evaluation of degradability, the amount of decomposition was expressed in % by setting the peak at the time of non-irradiation to 0 using HPLC. The results are shown in [Table 3].

HPLC: Hitachi High Technology, UV detector Chrom master5430
Developing solvent: acetonitrile/water/ammonium acetate
= 90/10/0.2 (volume ratio)
Flow rate: 1ml/min
Column: Inertsil ODS-2
Column temperature: 40°C
Detection: 254nm

From the results in [Table 3] above, the novel compound of the present invention has high decomposability with respect to UV light, and therefore, the amount of base generated by decomposition is large, and high-sensitivity curability is exhibited in the photosensitive resin composition.

[Examples 7 to 12 and Comparative Example 1] Preparation of photosensitive composition [Table 4] was blended, and photosensitive composition No. 1 was prepared. 1 to No. 6 and comparative photosensitive composition no. got 1. In addition, the numerical value of the composition in a table|surface represents a mass part.
In addition, the code of each component in the table represents the following component.
A-1 Compound No. 1
A-2 Compound No. 2
A-3 Compound No. 75
A-4 Compound No. 76
A-5 Compound No. 77
A-6 Compound No. 152
A'-1 Comparative compound No. 1
B-1 EPPN-201
(Phenol novolak type epoxy resin, epoxy equivalent 193 g / eq.,
manufactured by Nippon Kayaku Co., Ltd.)
B-2 TRR-5010G
(cresol novolac type phenol resin, hydroxyl equivalent 120 g/eq.,
Mw = 8,000, manufactured by Asahi Organic Chemicals Industry Co., Ltd.)
C-1 FZ-2122
(Polyether-modified polysiloxane, manufactured by Dow Corning Toray Co., Ltd.)
D-1 Cyclopentanone (solvent)

[Evaluation Examples 6 to 17 and Comparative Evaluation Examples 2 and 3] Evaluation of photosensitive composition and cured product 1 to No. 6 and comparative photosensitive composition no. 1 and their cured products were evaluated for line width sensitivity and residual film rate of cured products by the following procedure. The results are also shown in [Table 5].

[Method for preparing evaluation sample and evaluation method]
Photosensitive composition no. 1 to No. 6 and comparative photosensitive composition no. 1 (coating amount of about 2.0 cc) was applied to a glass substrate with a spin coater (500 rpm×2 seconds→1800 rpm×15 seconds→slope×5 seconds) and prebaked on a hot plate (90° C.×120 seconds).
After that, it was subjected to divisional exposure to ultraviolet light using a Topcon exposure machine (60, 120 mJ/cm ² , gap: 20 μm, illuminance: 20.0 mW/cm ² ).
After exposure, it was post-baked on a hot plate (120°C x 5 minutes), developed with PGMEA (temperature: 23°C, 200 rpm x 10 seconds), and washed with IPA (isopropyl alcohol) (200 rpm x 10 seconds → drying: 500 rpm x 5 seconds).
With respect to the obtained samples, the line width and residual film ratio of a pattern with a mask opening of 20 μm at each exposure dose were measured.

From the results of [Table 5] above, the photosensitive composition of the present invention showed a large line width (high sensitivity) and a high residual film rate (high curability) as compared with the comparative photosensitive composition. Therefore, it is clear that the compound of the present invention is excellent as a polymerization initiator.

[Examples 13 to 15 and Comparative Examples 2 and 3] Preparation of photosensitive composition [Table 6] was blended, and photosensitive composition No. 1 was prepared. 7 to No. 9, and Comparative Photosensitive Composition No. 2 and No. got 3. In addition, the numerical value of the composition in a table|surface represents a mass (g).
In addition, the code of each component in the table represents the following component.
A'-2 Comparative compound No. 2
B-3 KR-300
(Methyl/phenyl silicone resin, 50% xylene solution, manufactured by Shin-Etsu Chemical Co., Ltd.)
B-4 Tetraethoxysilane

[Evaluation Examples 18 to 20 and Comparative Evaluation Examples 4 and 5] Evaluation of photosensitive composition and cured product 7 to No. 9, Comparative photosensitive composition No. 2 and No. 3 and cured products thereof were evaluated for tackiness and transparency according to the following procedure. The results are also shown in [Table 7].

[Method for preparing evaluation sample and evaluation method]
Photosensitive composition no. 7 to No. 9 and comparative photosensitive composition no. 2 and No. 3 (coating amount of about 4.0 cc) was applied to a glass substrate with a spin coater (500 rpm×2 seconds→1800 rpm×15 seconds→slope×5 seconds) and prebaked on a hot plate (90° C.×120 seconds).
Then, it was exposed to ultraviolet light using a Topcon exposure machine (1000 mJ/cm ² , gap: 20 μm, illuminance: 20.0 mW/cm ² ).
After exposure, post-baking was performed on a hot plate (120° C.×5 minutes).
The surface of the obtained sample was rubbed with a cotton swab to check whether tack remained. The case where no tack remained was indicated by ◯, and the case where tack remained was indicated by x. A compound with an evaluation of ◯ is preferable as a polymerization initiator because of its high curability.
In addition, the ultraviolet/visible absorption spectra of the obtained samples were measured using a spectrophotometer, and the transmittance at 400 nm was compared. A compound with a transmittance of 80% or more is preferable as a polymerization initiator because of its high transparency, and a compound with a transmittance of less than 80% is not preferable as a polymerization initiator for applications requiring transparency because of its low transparency.
Spectrophotometer: Hitachi High-Tech Spectrophotometer U-3900

From the results in [Table 7] above, it is clear that the compounds of the present invention are polymerization initiators that are excellent in curability and transparency in compositions using silicone resins.

[Examples 16 and 17 and Comparative Example 4] Preparation of Photosensitive Compositions [Table 8] was blended, and photosensitive composition No. 1 was prepared. 10 and no. 11, and comparative photosensitive composition no. Got 4. In addition, the numerical value of the composition in a table|surface represents a mass (g).
In addition, the code of each component in the table represents the following component.
A'-3 Comparative compound No. 3
B-5 PEMP
(Tetrafunctional thiol monomer, manufactured by SC Organic Chemical Co., Ltd.)

[Evaluation Examples 21 and 22, and Comparative Evaluation Example 6] Evaluation of photosensitive composition and cured product 10 and no. 11, and comparative photosensitive composition no. 4 and their cured products were evaluated for sensitivity according to the following procedure. The results are listed in [Table 9].

[Method for preparing evaluation sample and evaluation method]
Photosensitive composition no. 10 and no. 11, and comparative photosensitive composition no. 4 (coating amount of about 4.0 cc) was applied to a glass substrate with a spin coater (500 rpm×2 seconds→1800 rpm×15 seconds→slope×5 seconds) and pre-baked on a hot plate (90° C.×120 seconds).
After that, a step tablet was placed on the coating film and exposed to ultraviolet light (365 nm, 385 nm, 395 nm) using an LED exposure machine (3000 mJ/cm ² , illuminance: 20.0 mW/cm ² ).
After exposure, it was post-baked on a hot plate (100° C.×20 minutes), developed with PGMEA (30 seconds), and washed with IPA (isopropyl alcohol) (10 seconds).
With respect to the obtained samples, the number of stages in which the film remained after development was recorded. A photosensitive resin composition having 5 or more stages is preferable because of its excellent sensitivity, and a composition having 10 or more stages is particularly preferable.

From the results in [Table 9] above, it is clear that the compound of the present invention is a polymerization initiator with excellent curability in a composition using an epoxy resin and a thiol as a curing agent.

[Examples 18 and 19 and Comparative Example 5] Preparation of Photosensitive Compositions [Table 10] was blended, and photosensitive composition No. 1 was prepared. 12 and no. 13, and comparative photosensitive composition no. Got 5. In addition, the numerical value of the composition in a table|surface represents a mass (g).
In addition, the code of each component in the table represents the following component.
B-6 Polyamic acid (obtained by reacting 3,3′,4,4′-biphenyltetracarboxylic dianhydride and bis(4-aminophenyl) ether in N,N-dimethylacetamide. Weight average molecular weight is about 10,000.)
D-2 NMP (solvent)

[Evaluation Examples 23 to 26 and Comparative Evaluation Examples 7 and 8] Evaluation of photosensitive composition and cured product 12 and no. 13, and comparative photosensitive composition no. 5 and their cured products were evaluated for line width sensitivity and residual film rate of the cured product according to the following procedure. The results are also shown in [Table 11].

[Method for preparing evaluation sample and evaluation method]
Photosensitive composition no. 12 and no. 13, and comparative photosensitive composition no. 5 (coating amount of about 4.0 cc) was applied to a glass substrate with a spin coater (500 rpm×2 seconds→1800 rpm×15 seconds→slope×5 seconds) and prebaked on a hot plate (100° C.×10 minutes).
After that, a Topcon exposure machine was used to perform divisional exposure to ultraviolet light (1000, 3000 mJ/cm ² , gap: 20 μm, illuminance: 20.0 mW/cm ² ).
After exposure, the film was post-baked on a hot plate (100° C. for 30 minutes), developed with IPA (temperature: 23° C., 200 rpm×10 seconds→drying: 500 rpm×5 seconds), and then heated at 300° C. for 1 hour.
With respect to the obtained samples, the line width and residual film ratio of a pattern with a mask opening of 20 μm at each exposure dose were measured.

From the results of [Table 12] above, it is clear that the compound of the present invention is a polymerization initiator having excellent curability in a resin composition using a polyamic acid.

The compounds of the present invention can also be used as thermal base generators.
[Reference Example 1]
The above photosensitive composition No. No. 11 was used to prepare a coating film in the same manner as above. The coating was heated using an oven at 150° C. for 60 minutes. When the resulting film was developed with IPA, it was confirmed that the residual film rate was 40.5% and that the film was cured.

[Reference example 2]
Heating and development were carried out in the same manner as in Reference Example 1, except that a composition without A-1 (compound No. 1) was used. As a result, no film remained.

From these results, it is clear that the compound of the present invention can also be used as a thermal base generator.

When used as a polymerization initiator, the novel compound of the present invention can generate a base more efficiently than conventional photobase generators, and can cure a photosensitive resin even at a low exposure dose.

Claims (10)

A compound represented by the following general formula (I).

(wherein R ¹ represents a cyano group, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms,
R ² , R ⁴ , R ⁵ , R ⁶ and R ⁷ each independently contain a hydrogen atom, a cyano group, a nitro group, -OR ⁸ , -COOR ⁸ , -CO-R ⁸ , -SR ⁸ , a halogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heterocyclic ring; represents an unsubstituted or substituted group having 2 to 20 carbon atoms,
R ³ represents an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or a group containing a heterocyclic ring and having 2 to 20 carbon atoms and being unsubstituted or substituted;
R ⁸ represents a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or a group containing a heterocyclic ring and having 2 to 20 carbon atoms and being unsubstituted or substituted;
X ¹ is —NR ¹¹ R ¹² , a group represented by (a) or (b) below,
R ¹¹ and R ¹² are each independently a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms,
R ¹¹ and R ¹² are linked together to form an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of a hydrogen atom, a nitrogen atom and a carbon atom, or an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of a hydrogen atom, an oxygen atom, a nitrogen atom and a carbon atom;
n represents 0 or 1; )

(wherein R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ and R ²² are each independently a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms,
at least one set of R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ , R ¹⁷ and R ¹⁸ , R ¹⁹ and R ²⁰ , and R ²¹ and R ²² is linked to each other to form an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of hydrogen, nitrogen and carbon atoms, or an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of hydrogen, oxygen, nitrogen and carbon atoms; and
* represents a bond. ) A compound represented by the following general formula (I).

(wherein R ¹ represents a cyano group, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms,
R ² , R ⁴ , R ⁵ , R ⁶ and R ⁷ each independently contain a hydrogen atom, a cyano group, a nitro group, -OR 8 , -COOR 8 , -CO-R 8 , -SR 8 , a halogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or a heterocyclic ring; represents an unsubstituted or substituted group ^having 2 ^to 20 ^carbon atoms ^,
R ³ represents an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or a group containing a heterocyclic ring and having 2 to 20 carbon atoms and being unsubstituted or substituted;
R ⁸ represents a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or a group containing a heterocyclic ring and having 2 to 20 carbon atoms and being unsubstituted or substituted;
X ¹ is —NR ¹¹ R ¹² , a group represented by (a) or (b) below,
R ¹¹ and R ¹² are each independently a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms,
R ¹¹ and R ¹² are linked together to form an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of a hydrogen atom, a nitrogen atom and a carbon atom, or an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of a hydrogen atom, an oxygen atom, a nitrogen atom and a carbon atom;
n represents 0 or 1;
However, at least one of the following conditions (i) and (ii) is satisfied.
(i) R ¹ represents an unsubstituted or substituted aliphatic hydrocarbon group having 6 to 20 carbon atoms;
(ii) n is 1, and R ¹ represents an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms; )

(wherein R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ and R ²² are each independently a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms,
at least one set of R ¹³ and R ¹⁴ , R ¹⁵ and R ¹⁶ , R ¹⁷ and R ¹⁸ , R ¹⁹ and R ²⁰ , and R ²¹ and R ²² is linked to each other to form an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of hydrogen, nitrogen and carbon atoms, or an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of hydrogen, oxygen, nitrogen and carbon atoms; and
* represents a bond. ) 3. The compound according to claim 1 , wherein at least one of R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ in the general formula (I) is a group having a nitro group, a benzoyl group or an o-methylbenzoyl group as a substituent. The compound according to any one of claims 1 to 3, wherein at least one of R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ in general formula (I) is a group represented by general formula (II) below.

(wherein R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ are each independently a hydrogen atom, a cyano group, a nitro group, -OR ³⁰ , -COOR ³⁰ , -CO-R 30 , ^{-SR 30 ,} a halogen atom, an unsubstituted or substituted C 1-20 aliphatic hydrocarbon group, an unsubstituted or substituted C 6-20 an aromatic hydrocarbon group or a group containing a heterocyclic ring and having 2 to 20 carbon atoms which is unsubstituted or substituted, or a group represented by the following general formula (III);
R ³⁰ represents an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms, or a group containing a heterocyclic ring and having 2 to 20 carbon atoms and being unsubstituted or substituted;
at least one of R ²⁵ , R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ represents a nitro group, —CO—R ³⁰ or a group represented by the following general formula (III);
* represents a bond. )

(wherein R ³¹ represents an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms or an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms,
X ² is —NR ³² R ³³ , a group represented by (a′) or (b′) below,
R ³² and R ³³ are each independently a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms,
R ³² and R ³³ are linked together to form an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of a hydrogen atom, a nitrogen atom and a carbon atom, or an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of a hydrogen atom, an oxygen atom, a nitrogen atom and a carbon atom;
m represents 0 or 1, * represents a bond. )

(wherein R ³⁴ , R ³⁵ , R ³⁶ , R ³⁷ , R ³⁸ , R ³⁹ , R ⁴⁰ , R ⁴¹ , R ⁴² and R ⁴³ are each independently a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted or substituted aromatic hydrocarbon group having 6 to 20 carbon atoms,
at least one of R ³⁴ and R ³⁵ , R ³⁶ and R ³⁷ , R ³⁸ and R ³⁹ , R ⁴⁰ and R ⁴¹ , and R ⁴² and R ⁴³ are linked to each other to form an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of hydrogen, nitrogen and carbon atoms, or an unsubstituted or substituted ring having 1 to 20 carbon atoms and consisting of hydrogen, oxygen, nitrogen and carbon atoms; and
* represents a bond. ) A latent base generator comprising the compound according to any one of claims 1 to 4 . A polymerization initiator containing the compound according to any one of claims 1 to 4 . A photosensitive resin composition comprising the polymerization initiator (A) according to claim 6 and a photosensitive resin (B). 8. The photosensitive resin composition according to claim 7 , wherein the photosensitive resin (B) is an epoxy resin or a phenol resin. A cured product of the photosensitive resin composition according to claim 7 or 8 . A method for producing a cured product, comprising the step of irradiating the photosensitive resin composition according to claim 7 or 8 with an energy ray.