JP6355890B2 - Polymer containing a triazine ring - Google Patents

Description

  The present invention relates to a triazine ring-containing polymer, a composition containing the same, a thin film, a film, a transparent plate or a lens made of the composition, and an electronic device, a light emitting device or an optical device containing them.

  (Meth) acrylic resins such as polymethylmethacrylate, and transparent resins such as polycarbonate resin, transparent epoxy resin, and transparent silicone resin are lighter and more workable than glass. Widely used in resins, transparent containers, transparent coating agents and the like. In recent years, resin products such as transparent resin lenses have been widely used in the field of optical components such as eyeglasses.

Furthermore, in the field of electronic materials, the above-mentioned transparent resins are being used frequently in applications of optical electronic materials such as antireflection coating agents for liquid crystal displays, transparent coating agents for solar cells, light-emitting diodes, and light-receiving portions of CCDs and CMOS sensors. .
In such applications of optical electronic materials, a high refractive index is often required not only for transparency but also for improving light extraction efficiency and light condensing performance.
Although the conventional transparent resin can control the mechanical properties to some extent by a technique such as crosslinking, a special technique is required to increase the optical characteristics, particularly the refractive index.

  Patent Documents 1 and 2 propose a technique for improving the refractive index by bonding a large amount of heavy atoms such as bromine and sulfur to an organic resin. Patent Documents 3 and 4 propose a method for improving the refractive index by dispersing inorganic oxide fine particles having a high refractive index in an organic resin. Furthermore, a high refractive index material made of a polymerizable triazine-based resin composition is also known (Patent Document 5). Patent Document 6 describes a linear triazine ring polymer or a triazine ring-containing hyperbranched polymer.

  In the methods of Patent Documents 1 and 2, generally, the obtained organic resin is unstable with respect to heat and light, so that there is a problem that it is likely to cause deterioration such as discoloration during long-term use. When used for material parts, there is a concern about electrode corrosion. Also, the methods of Patent Documents 3 and 4 have problems in the long-term storage stability of the obtained fine particle dispersed resin, and a large amount of dispersion is required to improve the dispersion stability of the inorganic oxide fine particles in the resin. Since a stabilizer is required, it becomes difficult to balance the refractive index and dispersion stability.

  Further, according to the method of Patent Document 5, although a resin having a relatively high refractive index and a high heat resistance can be obtained due to the triazine ring in the resin structure, the refractive index is not sufficiently high and further contributes to curing. Since some of the saturated binding sites remain unreacted, there are problems such as easy deterioration due to discoloration and deformation during long-term use. In Patent Document 6, it cannot be said that the refractive index is sufficiently high, and because it is a multi-branched polymer, the physical properties of the polymer obtained by polymerization conditions such as temperature and stirring state are not stable, and depending on the conditions, an insoluble gel There was a problem that sometimes.

JP-A-5-164901 JP 2005-350531 A JP 2007-27099 A JP 2007-308631 A JP 2011-038015 A International Publication No. 2010/128661 Pamphlet

  The present invention has been made in view of such circumstances, and is problematic in terms of heavy atoms with inherent problems such as instability to heat and light and electrode corrosion, long-term storage stability, and dispersion stability balance of refractive index. An object of the present invention is to provide a material having a high refractive index and a higher refractive index than a conventionally known high refractive index material without using a certain inorganic oxide fine particle dispersed resin.

（式（１）〜（５）中、Ｒは、２価の脂肪族炭化水素基、２価の芳香族炭化水素基、又は１以上の２価の脂肪族炭化水素基及び１以上の２価の芳香族炭化水素基から選択される１以上と、単結合、−Ｓ−、−Ｏ−、−ＮＨ−、−ＮＲ''−、−（ＣＯ）−ＮＨ−、−（ＣＯ）−Ｏ−及び−（ＣＯ）−から選択される１以上との組み合わせからなる２価の基を表す。Ｒはさらに置換基によって置換されていてもよい。
Ｒ’は、それぞれ水素原子、脂肪族炭化水素基、芳香族炭化水素基、又は１以上の脂肪族炭化水素基及び１以上の芳香族炭化水素基から選択される１以上と、単結合、−Ｓ−、−Ｏ−、−ＮＨ−、−ＮＲ''−、−（ＣＯ）−ＮＨ−、−（ＣＯ）−Ｏ−及び−（ＣＯ）−から選択される１以上との組み合わせからなる基を表す。Ｒ’はさらに置換基によって置換されていてもよい。
Ｒ^１は、水素原子、アセチル基、脂肪族炭化水素基、芳香族炭化水素基を有する脂肪族炭化水素基、又は芳香族炭化水素基と単結合、−Ｓ−、−Ｏ−、−ＮＨ−、−ＮＲ''−、−（ＣＯ）−ＮＨ−、−（ＣＯ）−Ｏ−及び−（ＣＯ）−から選択される１以上との組み合わせからなる基を有する脂肪族炭化水素基を表す。Ｒ^１はさらに置換基によって置換されていてもよい。
Ｒ^２は、脂肪族炭化水素基、芳香族炭化水素基を有する脂肪族炭化水素基、又は芳香族炭化水素基と単結合、−Ｓ−、−Ｏ−、−ＮＨ−、−ＮＲ''−、−（ＣＯ）−ＮＨ−、−（ＣＯ）−Ｏ−及び−（ＣＯ）−から選択される１以上との組み合わせからなる基を有する脂肪族炭化水素基を表す。Ｒ^２はさらに置換基によって置換されていてもよい。
Ｒ''は、脂肪族炭化水素基、芳香族炭化水素基、又は１以上の脂肪族炭化水素基及び１以上の芳香族炭化水素基から選択される１以上の組み合わせからなる基を表す。
Ｒ^３は、水素原子、置換もしくは無置換の炭素数１〜１０の脂肪族炭化水素基又は置換もしくは無置換の環形成炭素数６〜１０の芳香族炭化水素基を表す。
Ｒ^４は、置換もしくは無置換の炭素数１〜４の脂肪族炭化水素基を表す。
Ａｒは、２価の芳香族炭化水素基を表す。
Ｘは、それぞれヘテロ原子含有基を表す。
ｍは１〜５の整数を表す。
Ｙは、２価のヘテロ原子含有基（ただし、−ＮＲ’−を除く）である。
ｎはポリマーにおける繰り返し単位の繰り返し数を表し、２以上１０，０００以下の整数を表す。）
２．前記式（１）〜（５）において、Ｒ^１が水素原子、アセチル基又は炭素数１〜４の脂肪族炭化水素基であり、Ｒ^２が炭素数１〜４の脂肪族炭化水素基、又は環形成炭素数６〜１０の芳香族炭化水素基を有する炭素数１〜４の脂肪族炭化水素基であり、Ｒ^３が水素原子、炭素数１〜６の脂肪族炭化水素基又は環形成炭素数６〜１０の芳香族炭化水素基であり、Ｒ^４がメチル基又はエチル基であり、Ａｒが環形成炭素数６〜１０の２価の芳香族炭化水素基であり、Ｘがシアノ基、アミノ基、アルキルアミノ基、アリールアミノ基、ニトロ基、カルバモイル基、チオール基、アルキルメルカプト基、アリールメルカプト基、アルコキシ基、アルコキシカルボニル基又はアルコキシカルボニルオキシ基であり、Ｙが−Ｓ−又は−Ｏ−である１に記載のトリアジン環含有ポリマー。
３．下記式（６）〜（４８）のいずれかで表される繰返し単位を含むトリアジン環含有ポリマー。

（式（６）〜（４８）中、ｎはポリマーにおける繰り返し単位の繰り返し数を表し、２以上１０，０００以下の整数を表す。）
４．１〜３のいずれかに記載のトリアジン環含有ポリマー及び有機溶剤を含む組成物。
５．１〜３のいずれかに記載のトリアジン環含有ポリマー及び紫外線硬化剤を含む組成物。
６．１〜３のいずれかに記載のトリアジン環含有ポリマー及び熱硬化剤を含む組成物。
７．４〜６のいずれかに記載の組成物を用いて得られた薄膜、フィルム、透明板又はレンズ。
８．７に記載の薄膜、フィルム、透明板又はレンズを含む電子デバイス、発光デバイス又は光学デバイス。 According to the present invention, the following triazine ring-containing polymers and the like are provided.
1. The triazine ring containing polymer containing the repeating unit represented by either of following formula (1)-(5).

(In the formulas (1) to (5), R represents a divalent aliphatic hydrocarbon group, a divalent aromatic hydrocarbon group, or one or more divalent aliphatic hydrocarbon groups and one or more divalents. One or more selected from the following aromatic hydrocarbon groups, and a single bond, —S—, —O—, —NH—, —NR ″ —, — (CO) —NH—, — (CO) —O—. And a divalent group consisting of a combination with one or more selected from-(CO)-, wherein R may be further substituted with a substituent.
R ′ represents a hydrogen atom, an aliphatic hydrocarbon group, an aromatic hydrocarbon group, or one or more selected from one or more aliphatic hydrocarbon groups and one or more aromatic hydrocarbon groups, a single bond, — A group consisting of a combination with one or more selected from S-, -O-, -NH-, -NR "-,-(CO) -NH-,-(CO) -O- and-(CO)-. Represents. R ′ may be further substituted with a substituent.
R ¹ represents a hydrogen atom, an acetyl group, an aliphatic hydrocarbon group, an aliphatic hydrocarbon group having an aromatic hydrocarbon group, or an aromatic hydrocarbon group and a single bond, —S—, —O—, —NH—. , —NR ″ —, — (CO) —NH—, — (CO) —O—, and — (CO) — represents an aliphatic hydrocarbon group having a group formed of a combination with one or more. R ¹ may be further substituted with a substituent.
R ² represents an aliphatic hydrocarbon group, an aliphatic hydrocarbon group having an aromatic hydrocarbon group, or an aromatic hydrocarbon group and a single bond, —S—, —O—, —NH—, —NR ″ —. ,-(CO) -NH-,-(CO) -O- and-(CO)-represents an aliphatic hydrocarbon group having a group consisting of a combination with one or more. R ² may be further substituted with a substituent.
R ″ represents an aliphatic hydrocarbon group, an aromatic hydrocarbon group, or a group consisting of one or more combinations selected from one or more aliphatic hydrocarbon groups and one or more aromatic hydrocarbon groups.
R ³ represents a hydrogen atom, a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 ring carbon atoms.
R ⁴ represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 4 carbon atoms.
Ar represents a divalent aromatic hydrocarbon group.
Each X represents a heteroatom-containing group.
m represents an integer of 1 to 5.
Y is a divalent heteroatom-containing group (excluding —NR′—).
n represents the number of repeating units in the polymer and represents an integer of 2 or more and 10,000 or less. )
2. In the formulas (1) to (5), R ¹ is a hydrogen atom, an acetyl group, or an aliphatic hydrocarbon group having 1 to 4 carbon atoms, and R ² is an aliphatic hydrocarbon group having 1 to 4 carbon atoms, or A C 1-4 aliphatic hydrocarbon group having an aromatic hydrocarbon group having 6-10 ring-forming carbon atoms, wherein R ³ is a hydrogen atom, an aliphatic hydrocarbon group having 1-6 carbon atoms, or a ring-forming carbon An aromatic hydrocarbon group having 6 to 10 carbon atoms, R ⁴ is a methyl group or an ethyl group, Ar is a divalent aromatic hydrocarbon group having 6 to 10 ring carbon atoms, and X is a cyano group, An amino group, an alkylamino group, an arylamino group, a nitro group, a carbamoyl group, a thiol group, an alkyl mercapto group, an aryl mercapto group, an alkoxy group, an alkoxycarbonyl group or an alkoxycarbonyloxy group, and Y is —S— or —O. -Described in 1 Triazine ring-containing polymer.
3. The triazine ring containing polymer containing the repeating unit represented by either of following formula (6)-(48).

(In formulas (6) to (48), n represents the number of repeating units in the polymer, and represents an integer of 2 to 10,000.)
The composition containing the triazine ring containing polymer in any one of 4.1-3, and the organic solvent.
The composition containing the triazine ring containing polymer in any one of 5.1-3, and a ultraviolet curing agent.
The composition containing the triazine ring containing polymer in any one of 6.1-3, and a thermosetting agent.
A thin film, a film, a transparent plate or a lens obtained using the composition according to any one of 7.4 to 6.
An electronic device, light emitting device or optical device comprising the thin film, film, transparent plate or lens according to 8.7.

  According to the present invention, a triazine ring-containing polymer having a high refractive index can be provided.

2 is an NMR chart of the intermediate obtained in Example 1. 2 is an NMR chart of the triazine ring-containing polymer obtained in Example 1. It is a NMR chart of the intermediate body obtained in Examples 2-39. It is a NMR chart of the intermediate body obtained in Examples 2-39. It is a NMR chart of the intermediate body obtained in Examples 2-39. It is a NMR chart of the intermediate body obtained in Examples 2-39. It is a NMR chart of the intermediate body obtained in Examples 2-39. It is a NMR chart of the intermediate body obtained in Examples 2-39. It is a NMR chart of the intermediate body obtained in Examples 2-39. It is a NMR chart of the intermediate body obtained in Examples 2-39. It is a NMR chart of the intermediate body obtained in Examples 2-39. It is a NMR chart of the intermediate body obtained in Examples 2-39. It is a NMR chart of the intermediate body obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the triazine ring containing polymer obtained in Examples 2-39. It is a NMR chart of the intermediate body obtained in Examples 40-41. It is a NMR chart of the triazine ring containing polymer obtained in Examples 40-41. It is a NMR chart of the triazine ring containing polymer obtained in Examples 40-41. 2 is an NMR chart of the intermediate obtained in Example 42. 2 is an NMR chart of a triazine ring-containing polymer obtained in Examples 42 and 43. 2 is an NMR chart of a triazine ring-containing polymer obtained in Examples 42 and 43. 3 is an NMR chart of an intermediate obtained in Comparative Example 1. 2 is an NMR chart of a triazine ring-containing polymer obtained in Comparative Example 1. 4 is an NMR chart of intermediates obtained in Comparative Examples 2 and 3. 2 is an NMR chart of a triazine ring-containing polymer obtained in Comparative Examples 2 and 3. FIG. 2 is an NMR chart of a triazine ring-containing polymer obtained in Comparative Examples 2 and 3. FIG. It is a figure which shows the measurement result of the refractive index in the evaluation example 1. It is a figure which shows the measurement result of the refractive index in the evaluation example 2. It is a figure which shows the measurement result of the refractive index in the evaluation example 3. It is a figure which shows the measurement result of the refractive index in the evaluation example 4. It is a figure which shows the measurement result of the refractive index in the evaluation example 5. It is a figure which shows the measurement result of the refractive index in the evaluation example 6. It is a figure which shows the measurement result of the refractive index in the evaluation example 7. It is a figure which shows the measurement result of the refractive index in the evaluation example 8. It is a figure which shows the measurement result of the refractive index in the evaluation example 9. It is a figure which shows the measurement result of the refractive index in the evaluation example 10. It is a figure which shows the measurement result of the refractive index in the evaluation example 11. It is a figure which shows the measurement result of the refractive index in the evaluation example 12. It is a figure which shows the measurement result of the refractive index in the evaluation example 13. It is a figure which shows the measurement result of the refractive index in the evaluation example 14. It is a figure which shows the measurement result of the refractive index in the evaluation example 15. It is a figure which shows the measurement result of the refractive index in the evaluation example 16. It is a figure which shows the measurement result of the refractive index in the evaluation example 17. It is a figure which shows the measurement result of the refractive index in the evaluation example 18. It is a figure which shows the measurement result of the refractive index in the evaluation example 19. It is a figure which shows the measurement result of the refractive index in the evaluation example 20. It is a figure which shows the measurement result of the refractive index in the evaluation example 21. It is a figure which shows the measurement result of the refractive index in the evaluation example 22. It is a figure which shows the measurement result of the refractive index in the evaluation example 23. It is a figure which shows the measurement result of the refractive index in the evaluation example 24. It is a figure which shows the measurement result of the refractive index in the evaluation example 25. It is a figure which shows the measurement result of the refractive index in the evaluation example 26. It is a figure which shows the measurement result of the refractive index in the evaluation example 27. It is a figure which shows the measurement result of the refractive index in the evaluation example 28. It is a figure which shows the measurement result of the refractive index in the evaluation example 29. It is a figure which shows the measurement result of the refractive index in the evaluation example 30. It is a figure which shows the measurement result of the refractive index in the evaluation example 31. It is a figure which shows the measurement result of the refractive index in the evaluation example 32. It is a figure which shows the measurement result of the refractive index in the evaluation example 33. It is a figure which shows the measurement result of the refractive index in the evaluation example 34. It is a figure which shows the measurement result of the refractive index in the evaluation example 35. It is a figure which shows the measurement result of the refractive index in the evaluation example 36. It is a figure which shows the measurement result of the refractive index in the evaluation example 37. It is a figure which shows the measurement result of the refractive index in the evaluation example 38. It is a figure which shows the measurement result of the refractive index in the evaluation example 39. It is a figure which shows the measurement result of the refractive index in the evaluation example 40. It is a figure which shows the measurement result of the refractive index in the evaluation example 41. It is a figure which shows the measurement result of the refractive index in the evaluation example 42. It is a figure which shows the measurement result of the refractive index in the evaluation example 43. It is a figure which shows the measurement result of the refractive index in the evaluation example 44. It is a figure which shows the measurement result of the refractive index in the evaluation example 45. It is a figure which shows the measurement result of the refractive index in the evaluation example 46.

（式（１）〜（５）中、Ｒは、２価の脂肪族炭化水素基、２価の芳香族炭化水素基、又は１以上の２価の脂肪族炭化水素基及び１以上の２価の芳香族炭化水素基から選択される１以上と、単結合、−Ｓ−、−Ｏ−、−ＮＨ−、−ＮＲ''−、−（ＣＯ）−ＮＨ−、−（ＣＯ）−Ｏ−及び−（ＣＯ）−から選択される１以上との組み合わせからなる２価の基を表す。Ｒはさらに置換基によって置換されていてもよい。Ｒ’は、それぞれ水素原子、脂肪族炭化水素基、芳香族炭化水素基、又は１以上の脂肪族炭化水素基及び１以上の芳香族炭化水素基から選択される１以上と、単結合、−Ｓ−、−Ｏ−、−ＮＨ−、−ＮＲ''−、−（ＣＯ）−ＮＨ−、−（ＣＯ）−Ｏ−及び−（ＣＯ）−から選択される１以上との組み合わせからなる基を表す。Ｒ’はさらに置換基によって置換されていてもよい。Ｒ^１は、水素原子、アセチル基、脂肪族炭化水素基、芳香族炭化水素基を有する脂肪族炭化水素基、又は芳香族炭化水素基と、単結合、−Ｓ−、−Ｏ−、−ＮＨ−、−ＮＲ''−、−（ＣＯ）−ＮＨ−、−（ＣＯ）−Ｏ−及び−（ＣＯ）−から選択される１以上との組み合わせからなる基を有する脂肪族炭化水素基を表す。Ｒ^１はさらに置換基によって置換されていてもよい。Ｒ^２は、脂肪族炭化水素基、芳香族炭化水素基を有する脂肪族炭化水素基、又は芳香族炭化水素基と、単結合、−Ｓ−、−Ｏ−、−ＮＨ−、−ＮＲ''−、−（ＣＯ）−ＮＨ−、−（ＣＯ）−Ｏ−及び−（ＣＯ）−から選択される１以上との組み合わせからなる基を有する脂肪族炭化水素基を表す。Ｒ^２はさらに置換基によって置換されていてもよい。Ｒ''は、脂肪族炭化水素基、芳香族炭化水素基、又は１以上の脂肪族炭化水素基及び１以上の芳香族炭化水素基から選択される１以上の組み合わせからなる基を表す。Ｒ^３は、水素原子、置換もしくは無置換の炭素数１〜１０の脂肪族炭化水素基又は置換もしくは無置換の環形成炭素数６〜１０の芳香族炭化水素基を表す。Ｒ^４は、置換もしくは無置換の炭素数１〜４の脂肪族炭化水素基を表す。Ａｒは、２価の芳香族炭化水素基を表す。Ｘは、それぞれヘテロ原子含有基を表す。ｍは１〜５の整数を表す。Ｙは、２価のヘテロ原子含有基（ただし、−ＮＲ’−を除く）である。ｎはポリマーにおける繰り返し単位の繰り返し数を表し、２以上１０，０００以下の整数を表す。） The triazine ring-containing polymer of the present invention includes a repeating unit represented by any of the following formulas (1) to (5).

(In the formulas (1) to (5), R represents a divalent aliphatic hydrocarbon group, a divalent aromatic hydrocarbon group, or one or more divalent aliphatic hydrocarbon groups and one or more divalents. One or more selected from the following aromatic hydrocarbon groups, and a single bond, —S—, —O—, —NH—, —NR ″ —, — (CO) —NH—, — (CO) —O—. And a divalent group consisting of a combination with one or more selected from-(CO)-, wherein R may be further substituted with a substituent, and R 'is a hydrogen atom or an aliphatic hydrocarbon group, respectively. , An aromatic hydrocarbon group, or one or more selected from one or more aliphatic hydrocarbon groups and one or more aromatic hydrocarbon groups, a single bond, -S-, -O-, -NH-, -NR ″ Represents a group consisting of a combination with one or more selected from —, — (CO) —NH—, — (CO) —O—, and — (CO) —. Good .R ¹ be substituted by a substituent, the hydrogen atom, an acetyl group, an aliphatic hydrocarbon group, an aliphatic hydrocarbon group, or an aromatic hydrocarbon group having an aromatic hydrocarbon group, a single bond , -S-, -O-, -NH-, -NR "-,-(CO) -NH-,-(CO) -O- and-(CO)- R ¹ may be further substituted with a substituent, R ² may be an aliphatic hydrocarbon group, an aliphatic hydrocarbon group having an aromatic hydrocarbon group, or From an aromatic hydrocarbon group and a single bond, —S—, —O—, —NH—, —NR ″ —, — (CO) —NH—, — (CO) —O— and — (CO) —. R ² represents an aliphatic hydrocarbon group having a group consisting of a combination with one or more selected, and R ² is further substituted. R ″ is an aliphatic hydrocarbon group, an aromatic hydrocarbon group, or one or more selected from one or more aliphatic hydrocarbon groups and one or more aromatic hydrocarbon groups. And R ³ represents a hydrogen atom, a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 ring carbon atoms. R ⁴ represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 4 carbon atoms, Ar represents a divalent aromatic hydrocarbon group, and X represents a heteroatom-containing group. m represents an integer of 1 to 5. Y is a divalent hetero atom-containing group (excluding —NR′—), n represents the number of repeating units in the polymer, and is 2 or more and 10,000. Represents the following integers.)

  The triazine ring-containing polymer of the present invention has a structure in which the monomer structure represented by any of the above formulas (1) to (5) is linearly connected, and exhibits a high refractive index when formed into a thin film or the like.

The triazine ring-containing polymer of the present invention exhibits a high refractive index due to the structure of other sites, even if R is any group shown above.
In the compounds other than the present invention, if R is a sterically bulky divalent aromatic hydrocarbon group, the refractive index may be relatively low. For example, a compound exemplified in Patent Document 6, that is, in the formula (1) of the present invention, R ′ is a hydrogen atom, R ¹ is a hydrogen atom, R ² is a phenyl group, and R is a divalent group containing a fluorene skeleton. In some compounds, fluorene is sterically large when each polymer molecular chain interacts, and since the interaction is weaker than that of the present invention, the intermolecular voids increase and the refractive index becomes relatively low.

As for carbon number of the bivalent aliphatic hydrocarbon group of R, 1-20 are preferable. The ring-forming carbon number of the divalent aromatic hydrocarbon group is preferably 6-10.
R is preferably a divalent aromatic hydrocarbon group or one or more divalent aromatic hydrocarbon groups and a single bond, -S-, -O-, -NH-, -NR-,-( It is a divalent group consisting of a combination with one or more selected from CO) —NH—, — (CO) —O— and — (CO) —.
R may be further substituted with other groups, and these substituents are as described later.

As for carbon number of the aliphatic hydrocarbon group of R ', 1-20 are preferable. The ring-forming carbon number of the aromatic hydrocarbon group is preferably 6-10.
Even if R ′ is any of the groups shown above, the triazine ring-containing polymer of the present invention exhibits a high refractive index due to the structure of other sites, but R ′ is a hydrogen atom, an aromatic hydrocarbon group, or 1 From the above aromatic hydrocarbon group and a single bond, —S—, —O—, —NH—, —NR—, — (CO) —NH—, — (CO) —O— and — (CO) —. A group consisting of a combination with one or more selected is preferred.
R ′ may be further substituted with other groups, and these substituents are as described later.

The number of carbon atoms of the aliphatic hydrocarbon group R ¹ from 1 to 20 are preferred. The ring-forming carbon number of the aromatic hydrocarbon group is preferably 6-10.
R ¹ is preferably a hydrogen atom, an acetyl group, or an aliphatic hydrocarbon group having 1 to 4 carbon atoms.
When R ¹ is an aliphatic hydrocarbon group having 1 to 4 carbon acetyl group or a C, steric repulsion of R ¹ each other between the polymer is reduced, the intermolecular voids is preferred because relatively small.
When R ¹ is a hydrogen atom, the interaction is further strengthened by forming a hydrogen bond with an amino group other than the nitrogen atom to which the hydrogen atom is bonded, a hetero atom-containing substituent X, or a triazine ring site, It is preferable because the intermolecular voids are further reduced and the refractive index becomes relatively high.
R ¹ may be further substituted with other groups, and these substituents are as described later.

The number of carbon atoms of the aliphatic hydrocarbon group R ² is from 1 to 20 are preferred. The ring-forming carbon number of the aromatic hydrocarbon group is preferably 6-10.
R ² is preferably an aliphatic hydrocarbon group having 1 to 4 carbon atoms or an aliphatic hydrocarbon group having 1 to 4 carbon atoms having an aromatic hydrocarbon group having 6 to 10 ring carbon atoms.
R ² may be further substituted with other groups, and these substituents are as described later.

R ³ is preferably a hydrogen atom, an aliphatic hydrocarbon group having 1 to 6 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 ring carbon atoms.
R ⁴ is preferably a methyl group or an ethyl group.

  Ar is preferably a divalent aromatic hydrocarbon group having 6 to 10 ring carbon atoms, and specifically, a phenyl group or a naphthyl group is preferable. When the number of carbon atoms is 10 or less, inhibition of intermolecular interaction due to steric repulsion can be reduced, and a material having excellent solubility and easy handling can be obtained.

（式中、Ｒ’はそれぞれ上記と同じである。）
Ｘは、シアノ基、ニトロ基又はカルバモイル基であるとより好ましい。
ＸのＡｒ上の置換数、即ちｍは１〜５であり、Ａｒに複数のＸが置換する場合、それぞれのＸは同一でも異なっていてもよい。ｍは好ましくは１〜３である。 Examples of the hetero atom-containing group of X include a nitrogen atom-containing group, an oxygen atom-containing group, a sulfur atom-containing group, and the like, preferably a cyano group, an amino group, an alkylamino group, an arylamino group, a nitro group, a carbamoyl group, A thiol group, an alkyl mercapto group, an aryl mercapto group, an alkoxy group, an alkoxycarbonyl group, an alkoxycarbonyloxy group or a group represented by the following formula (6) further enhances the above interaction, and has a higher refractive index. This is preferable.

(Wherein R ′ is the same as above)
X is more preferably a cyano group, a nitro group or a carbamoyl group.
The number of substitution of X on Ar, that is, m is 1 to 5, and when Ar is substituted with a plurality of X, each X may be the same or different. m is preferably 1 to 3.

Y is preferably -S- or -O-.
n is preferably 5 to 2,000.

  Examples of the substituent include an alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an aromatic hydrocarbon group, and a heterocyclic group. And hetero atom-containing substituents.

In the formula (1), the side chain amino group site (—N (—R ¹ ) (— R ² )) is an amino group having at least one aliphatic hydrocarbon group directly bonded to a nitrogen atom. (That is, when R ¹ is a hydrogen atom or an aliphatic hydrocarbon group and / or R ² is an aliphatic hydrocarbon group), an amino having at least one aromatic hydrocarbon group directly bonded to the nitrogen atom Compared to the case of the group (that is, the case where either ^one of R ¹ and R ² includes an aromatic hydrocarbon group directly bonded to the nitrogen atom), the electron density of the amine nitrogen is increased. This is preferable because the interaction is strengthened, the intermolecular voids are reduced, and the electron density at the triazine ring portion is increased to obtain a relatively high refractive index.
Further, it is preferable that R ¹ is an acetyl group because the electron density of the amine nitrogen increases due to the electronic interaction of the carbonyl group site, and the refractive index becomes relatively high by the same mechanism.

The aliphatic hydrocarbon group in the formula (1) is more preferably 1 to 4 carbon atoms because the steric repulsion between them is reduced and the intermolecular voids are relatively reduced.
When R ¹ is a hydrogen atom and R ² is an aliphatic hydrocarbon group, the hydrogen atom of R ¹ is bonded to an amino group other than the nitrogen atom to which the hydrogen atom is bonded or to a triazine ring site. And the interaction is further strengthened, and therefore, the intermolecular voids are further reduced and the refractive index is relatively high, which is preferable.

In the formula (2), the side chain amino group site (—N (—R ¹ ) (— Ar— (X) _m )) has one aromatic hydrocarbon group having at least one heteroatom-containing substituent. Since it is an amino group, the electron density of the amine nitrogen is increased as compared with the case of an amino group having one aromatic hydrocarbon group that does not have a heteroatom-containing substituent. Interactions such as hydrogen bonds with aromatic ring sites such as hydrogen and triazine ring on the amino group are generated, thereby strengthening the interaction between each molecule and reducing intermolecular voids. Furthermore, the electron density of the triazine ring site Therefore, a relatively high refractive index is preferable.

In the case of formula (3), in the side chain thioether moiety (—S—R ³ ), when R ³ is a thioether having an aliphatic hydrocarbon group or an aromatic hydrocarbon group, an amine having an aromatic hydrocarbon group Compared to other cases, the interaction between each molecule based on the thioether moiety is strengthened, the intermolecular voids are reduced, and the electron density of the triazine ring moiety is increased, resulting in a relatively high refractive index. It becomes.
When R ³ is an aliphatic hydrocarbon group, it is more preferable that the number of carbon atoms is 1 to 6 because steric repulsion between them is reduced and intermolecular voids are relatively reduced.
When R ³ is an aromatic hydrocarbon group, it is more preferable that the ring-forming carbon number is 6 to 10 because the steric repulsion between them is reduced and the intermolecular voids are relatively reduced.
These aliphatic hydrocarbon groups and aromatic hydrocarbon groups may have a substituent such as a heteroatom-containing substituent. Examples of the hetero atom-containing substituent include a nitrogen atom-containing group, an oxygen atom-containing group, a sulfur atom-containing group, and the like, specifically as described later.

In the case of formula (4), the side chain moiety (—O—R ⁴ ) is an alkoxyl group in which R ⁴ is an aliphatic hydrocarbon group, so that the side chain has an aryloxy group or an aromatic hydrocarbon group. Compared to the case of the same type, since the substituent is not sterically bulky, the intermolecular voids are reduced and the refractive index is relatively high. R ⁴ is more preferably a methyl group or an ethyl group because the steric repulsion between them is reduced and the intermolecular voids are relatively reduced.
These aliphatic hydrocarbon groups and aromatic hydrocarbon groups may have a substituent such as a heteroatom-containing substituent. Examples of the hetero atom-containing substituent include a nitrogen atom-containing group, an oxygen atom-containing group, a sulfur atom-containing group, and the like, specifically as described later.

  In the formula (5), Y is a divalent heteroatom-containing substituent (except when it is —NR′—), and is a divalent substituent represented by —S— or —O—. Preferably there is.

In the structures of the above formulas (1) to (5), when the triazine ring is centered, two or three nitrogen atoms of the amino group are bonded to three carbon atoms of the triazine ring, and in the two cases, the remaining A sulfur atom or oxygen atom which is a hetero atom is bonded to one carbon atom . In order to develop a high refractive index, the above structure is preferable because the electron density of the triazine ring structure is relatively high electronically .

  The high refractive index materials represented by the above formulas (1) to (5) have different structures, but the mechanism for achieving a high refractive index is the same, and the degree of effect differs depending on the type of each group selected. However, these advantages and disadvantages cannot be generally stated.

Further, in the triazine ring-containing polymer of the above formulas (1) to (5), a strong interaction such as a hydrogen bond is expressed between the triazine ring and each substituent, or between each substituent, and each polymer molecular chain is mutually connected. A structure having a substituent that reduces intermolecular voids by acting is further preferred. This is because the degree of effect differs depending on the type of R ¹ , R ² , R ³ , R, R ′, X, etc. to be selected, and furthermore, since they influence in a complex manner, it cannot be said about their superiority or inferiority. Specifically, the following formulas (6), (7), (9), (13), (14), (20), (21), (22), (24), (27), ( In the case of the triazine ring-containing polymer represented by 28), (35), (36), (37), (41), (42), (45), n _D exceeds 1.80 and is particularly high in refractive index. Is particularly preferable.

Hereinafter, each group in said formula (1)-(5) is demonstrated concretely.
Examples of the aliphatic hydrocarbon group (alkyl group) include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, and n-hexyl. Group, n-heptyl group, n-octyl group, cyclopentyl group, cyclohexyl group and the like.
Examples of the divalent aliphatic hydrocarbon group include groups in which one hydrogen atom has been removed from the above.

As the aromatic hydrocarbon group (aryl group), phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, naphthacenyl group, chrysenyl group, benzo [c] phenanthryl group, benzo [g] chrysenyl group, triphenylenyl group, 1-fluorenyl group, 2-fluorenyl group, 3- Fluorenyl group, 4-fluorenyl group, 9-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, terphenyl group, fluoranthenyl Groups and the like.
Examples of the divalent aromatic hydrocarbon group include groups in which one hydrogen atom has been removed from the above.

Examples of the cycloalkyl group include those in which an example of the alkyl group having 3 or more carbon atoms is an aliphatic ring structure.
Examples of the aralkyl group include those in which a hydrogen atom of the alkyl group is substituted with the aryl group.

  Heterocyclic groups include pyrrole ring, isoindole ring, benzofuran ring, isobenzofuran ring, dibenzothiophene ring, isoquinoline ring, quinoxaline ring, phenanthridine ring, phenanthroline ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, Triazine ring, indole ring, quinoline ring, acridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzoxazole ring, thiazole ring, thiadiazole And groups formed from a ring, a benzothiazole ring, a triazole ring, an imidazole ring, a benzimidazole ring, a pyran ring, a dibenzofuran ring, a benzo [c] dibenzofuran ring, a carbazole ring, and derivatives thereof.

  As the hetero atom-containing substituent, a cyano group, amino group, alkylamino group, arylamino group, nitro group, thiol group, alkyl mercapto group, aryl mercapto group, alkoxycarbonyl group or alkoxycarbonyloxy group is preferred.

  Examples of the alkylamino group include those obtained by substituting one or two hydrogen atoms of an amino group with the above alkyl group, for example, a methylamino group, a dimethylamino group, an ethylamino group, an n-propylamino group, an isopropylamino group. And a cyclohexylamino group.

  Examples of the arylamino group include those obtained by substituting one or two hydrogen atoms of the amino group with the above aryl group. For example, an anilino group, a toluidino group, a mesidino group, a nitrogen atom-containing group, an oxygen atom-containing group, sulfur Anilino group etc. which have hetero atom containing groups, such as an atom containing group, are mentioned.

  Examples of the alkyl mercapto group include those in which the hydrogen atom of the mercapto group is substituted with the above alkyl group, and examples thereof include a methylthio group, an ethylthio group, an n-propylthio group, and an isopropylthio group.

  Examples of the aryl mercapto group include those in which the hydrogen atom of the mercapto group is substituted with the aryl group, and examples thereof include a phenylthio group and a naphthylthio group.

  Examples of the alkoxycarbonyl group include groups obtained by bonding the above alkyl group, oxygen atom and carbonyl group in this order, and examples thereof include a methoxycarbonyl group and an ethoxycarbonyl group.

  Examples of the alkoxycarbonyloxy group include groups obtained by bonding the above alkyl group, carbonyl group and oxygen atom in this order, and examples thereof include a methoxycarbonyloxy group and an ethoxycarbonyloxy group.

（式（６）〜（４８）中、ｎはポリマーにおける繰り返し単位の繰り返し数を表し、２以上１０，０００以下の整数を表す。） The triazine ring-containing polymer of the present invention preferably contains a repeating unit represented by any of the following formulas (6) to (48).

(In formulas (6) to (48), n represents the number of repeating units in the polymer, and represents an integer of 2 to 10,000.)

  The triazine ring-containing polymer of the present invention is a condensation reaction of a conventionally known dichlorotriazine compound and a compound having a nucleophilic functional group represented by a diamine compound, or a triazine ring-containing compound having a conventionally known nucleophilic functional group. It can manufacture using the reaction of an active ester compound. Specifically, as described in the examples.

The 1st composition of this invention contains said triazine ring containing polymer and an organic solvent.
As the organic solvent, any organic solvent can be used as long as the above-described high refractive index material is dissolved. Specifically, amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide, Examples thereof include halogen solvents such as 1,1,2,2-tetrachloroethane, chloroform and dichloromethane, ketone solvents such as cyclohexanone and methyl ethyl ketone, ester solvents such as ethyl acetate, and ether solvents such as tetrahydrofuran.
The content of the organic solvent cannot be defined unconditionally depending on the type of high refractive index material used, the type of solvent, the use of the high refractive index composition, or the use conditions, but is usually 50 to 99.9% by weight based on the entire composition. It is.

The 2nd composition of this invention contains said triazine ring containing polymer and a ultraviolet curing agent.
Examples of the ultraviolet curing agent include conventionally known persulfates such as ammonium persulfate, azo compounds such as 4,4′-azobis (4-cyanovaleric acid), diacyl peroxide compounds such as isobutyryl peroxide, bis (4- and peroxydicarbonate compounds such as t-butylcyclohexyl) peroxydicarbonate.
The content of the ultraviolet curing agent is 0.001 to 10% by weight based on the entire composition.

The 3rd composition of this invention contains said triazine ring containing polymer and a thermosetting agent.
Examples of the thermosetting agent include known epoxy resin-aliphatic amine-based curing agents, polyisocyanate-based curing agents, and the like.
The content of the thermosetting agent is 0.01 to 30% by weight based on the entire composition.

  Moreover, you may add a curing catalyst, a stabilizer, a film thickness adjusting material, a leveling material, a transparency improving material, a strength improving material, etc. as another additive. What is necessary is just to adjust these kinds, addition amount, etc. suitably according to the triazine ring containing polymer etc. which are contained in a composition.

A thin film, a film, a transparent plate, or a lens (thin film, etc.) can be obtained using the above composition. The thin film of the present invention has a high refractive index.
These can be produced by a known method, and specifically, can be produced by spin coating, flow coating, casting, stretching, pressing, injection, or the like.

  The above thin film or the like can be used for an electronic device, a light emitting device, an optical device, or the like. As these devices, for example, an optical information processing apparatus and the like in addition to a lighting fixture and a display made up of an LED device, an organic EL device, and the like.

Example 1
A 500 ml three-necked flask equipped with a low temperature thermometer of −50 ° to 50 °, a 100 ml dropping funnel, and a Jim Roth condenser is charged with 200 ml of 14.8 g (80 mmol) of cyanuric chloride in tetrahydrofuran and ice / salt Cooled in a bath to -10 ° C. As a side chain structure precursor, a solution of 2.7 g (88 mmol) of methylamine in 60 ml of tetrahydrofuran was dropped from a dropping funnel over 90 minutes, and after completion, stirring was continued for 30 minutes at the same temperature. Thereafter, the content was poured into 400 ml of water containing 2 ml of concentrated hydrochloric acid, extracted with ethyl acetate, the organic layer was washed twice with saturated brine, and the solvent was distilled off under reduced pressure to obtain the target intermediate. 12.9 g (yield 90%) of certain 2-methylamino-4,6-dichlorotriazine (A-1) was obtained. The NMR chart of the target intermediate is shown in FIG.

Subsequently, 2.3 g (10 mmol) of 4,4′-diaminobenzanilide as a main chain diamine skeleton precursor was added to a 100 ml three-necked flask equipped with a 200 ° C. thermometer, a 50 ml dropping funnel, and a Jim Roth condenser. And 20 ml of N, N′-dimethylacetamide was added and dissolved by stirring for 10 minutes in an oil bath set at 100 ° C. in advance. To this solution, 10 ml of N, N′-dimethylacetamide solution of 1.8 g (10 mmol) of 2-methylamino-4,6-dichlorotriazine (A-1) obtained as a triazine monomer was added from a dropping funnel for about 5 seconds. At a stroke and stirred at 100 ° C. for 5 minutes. 0.5 ml of aniline was charged at a time, and further stirred for 10 minutes, and then allowed to cool to room temperature. This solution was put into 200 ml of water containing 3.75 g of potassium carbonate, and the precipitated crystals were separated by filtration. The crystals were washed with ethanol and dried under reduced pressure to quantitatively obtain the target product (B-1). The NMR chart of the target product is shown in FIG.

Examples 2-39
The target intermediates (A-2) to (A-11) were obtained in the same manner as in Example 1 except that the side chain structure precursor shown in Table 1 was used as the side chain structure precursor. NMR charts of the target intermediates (A-2) to (A-11) are shown in FIGS.
Subsequently, the obtained target intermediate was used in the same manner as in Example 1 except that the main chain diamine skeleton precursor described in Table 1 was used as the main chain diamine skeleton precursor. (B-39) was obtained. NMR charts of the target products (B-2) to (B-39) are shown in FIGS.

Examples 40 and 41
Instead of the tetrahydrofuran solution of methylamine in Example 1, an equimolar amount of sodium hydride was added to the tetrahydrofuran solution of the side chain structure precursor described in Table 1, and a suspension in the form of a sodium salt was used. In the same manner as in Example 1, the target intermediate (A-12) was obtained. An NMR chart of the target intermediate (A-12) is shown in FIG.
Then, using the obtained target intermediate, the target product (B-40) was obtained in the same manner as in Example 1 except that the main chain diamine skeleton precursor described in Table 1 was used as the main chain diamine skeleton precursor. (B-41) was obtained. The NMR chart of the target product is shown in FIGS.

Examples 42 and 43
In the same manner as in Example 15, the target intermediate (A-4-2) was obtained.
Next, using the obtained intermediate (A-4-2), as a main chain diamine skeleton precursor, N of the main chain diamine skeleton precursor described in Table 1 instead of 4,4′-diaminobenzanilide. , N′-dimethylacetamide solution was reacted at room temperature (25 ° C.) for 30 minutes and purified to obtain polymerization intermediates (A-42) and (A-43). The target products (B-42) and (B-43) were obtained in the same manner as in Example 15 except that the reaction was performed at 100 ° C. by the above method. NMR charts of the polymerization intermediate (A-42) and the target products (B-42) and (B-43) are shown in FIGS.

Comparative Example 1
The target product was obtained by the same method as that described in Example 5 of WO2010 / 128661. That is, the target intermediate (C-1) was obtained in the same manner as in Example 1 except that aniline was used instead of monomethylamine as the side chain structure precursor.
Subsequently, Example was used except that 9,9-bis (4-aminophenyl) fluorene was used in place of 4,4′-diaminobenzanilide as the main chain diamine skeleton precursor using intermediate (C-1). 1 was obtained in the same manner as in Example 1.
NMR charts of the intermediate (C-1) and the target product (D-1) are shown in FIGS.

Comparative Examples 2 and 3
Instead of the tetrahydrofuran solution of methylamine in Example 1, an equimolar amount of sodium hydride was added to a tetrahydrofuran solution of N-phenylacetamide to obtain a sodium salt suspension. (C-2) was obtained. The NMR chart of the target intermediate (C-2) is shown in FIG.
Subsequently, 4,4′-diaminobenzanilide (Comparative Example 2) or 9,9-bis (4-aminophenyl) fluorene (Comparative Example 3) was used as a main chain diamine skeleton precursor using the obtained target intermediate. Except that was used, in the same manner as in Example 1, the desired products (D-2) and (D-3) were obtained. The NMR chart of the target product is shown in FIGS.

Evaluation Examples 1-46
N-methyl-2-pyrrolidone as a coating solvent, triazine ring-containing polymers (B-1) to (B-43) and (D-1) obtained in Examples 1 to 43 and Comparative Examples 1 to 3 as a solid content Using (D-3), a coating solution was prepared so that the solid content was 2.5% by weight. A synthetic quartz substrate having a size of 2 cm × 2 cm and a thickness of 1 mm is fixed to a spin coater, and the coating solution filtered through a filter having a pore diameter of 0.2 μ is dropped on this substrate, and rotated at 2000 rpm for 60 seconds on the substrate. It was applied evenly. Then, the said board | substrate was set | placed on the hotplate preset to 200 degreeC, the solvent was volatilized by making it heat-dry for 30 minutes, and the thin film which consists of a triazine ring containing polymer was formed on the board | substrate.

About the said thin film, it analyzed with the general dispersion formula model using the spectroscopic ellipsometry apparatus, and calculated | required the refractive index in the wavelength range of 190-1700 nm. The results are shown in FIGS. Further, Table 2 shows n _D and Abbe number obtained from FIGS.

The Abbe number is a numerical value representing the wavelength dispersion of the refractive index, and was calculated by (n _D −1) / (n _F −n _C ). _{n D,} n F, n _C is as follows.
n _D : refractive index of D line (589.3 nm) n _F : refractive index of F line (486.1 nm) n _C : refractive index of C line (656.3 nm)

  From these results, it can be seen that the thin film obtained using the triazine ring-containing polymer of the present invention has a high refractive index.

  The thin film obtained from the polymer of the present invention can be used for electronic devices, light emitting devices, optical devices and the like.

Claims (9)

The triazine ring containing polymer containing the repeating unit represented by either of following formula (1)- (4) .

(In the formulas (1) to (4) , R represents two divalent aromatic hydrocarbon groups, —S—, —O—, —NH—, —NR ″ —, and — (CO) —). Represents a divalent group consisting of a combination with one or more selected from R. R may be further substituted with a substituent.
R ′ is a hydrogen atom, an aliphatic hydrocarbon group, an aromatic hydrocarbon group, or one or more selected from one or more aliphatic hydrocarbon groups and one or more aromatic hydrocarbon groups, and —S—, A group consisting of a combination with one or more selected from —O—, —NH—, —NR ″ —, and — (CO) —. R ′ may be further substituted with a substituent.
R ¹ represents a hydrogen atom, an acetyl group, an aliphatic hydrocarbon group, an aliphatic hydrocarbon group having an aromatic hydrocarbon group, or an aromatic hydrocarbon group; and —S—, —O—, —NH—, — It represents an aliphatic hydrocarbon group having a group consisting of one or more selected from NR ″ — and — (CO) —. R ¹ may be further substituted with a substituent.
R ² represents an aliphatic hydrocarbon group, an aliphatic hydrocarbon group having an aromatic hydrocarbon group, or an aromatic hydrocarbon group; and —S—, —O—, —NH—, —NR ″ —, and An aliphatic hydrocarbon group having a group consisting of one or more selected from — (CO) —. R ² may be further substituted with a substituent.
R ″ represents an aliphatic hydrocarbon group, an aromatic hydrocarbon group, or a group consisting of one or more combinations selected from one or more aliphatic hydrocarbon groups and one or more aromatic hydrocarbon groups.
R ³ represents a hydrogen atom, a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 ring carbon atoms.
R ⁴ represents a substituted or unsubstituted aliphatic hydrocarbon group having 1 to 4 carbon atoms.
Ar represents a divalent aromatic hydrocarbon group.
Each X represents a heteroatom-containing group.
m represents an integer of 1 to 5 .
n represents the number of repeating units in the polymer and represents an integer of 2 or more and 10,000 or less. ) In the above formulas (1) to (4) , R ¹ is a hydrogen atom, an acetyl group or an aliphatic hydrocarbon group having 1 to 4 carbon atoms, and R ² is an aliphatic hydrocarbon group having 1 to 4 carbon atoms, or A C 1-4 aliphatic hydrocarbon group having an aromatic hydrocarbon group having 6-10 ring-forming carbon atoms, wherein R ³ is a hydrogen atom, an aliphatic hydrocarbon group having 1-6 carbon atoms, or a ring-forming carbon An aromatic hydrocarbon group having 6 to 10 carbon atoms, R ⁴ is a methyl group or an ethyl group, Ar is a divalent aromatic hydrocarbon group having 6 to 10 ring carbon atoms, and X is a cyano group, The triazine ring-containing product according to claim 1, which is an amino group, alkylamino group, arylamino group, nitro group, carbamoyl group, thiol group, alkyl mercapto group, aryl mercapto group, alkoxy group, alkoxycarbonyl group or alkoxycarbonyloxy group. Po Ma. The triazine ring containing polymer containing the repeating unit represented by either of following formula (6)-(13), (15)-(20), (23)-(35), and (38)-(46).

(In the formulas (6) to (13), (15) to (20), (23) to (35), and (38) to (46), n represents the number of repeating units in the polymer, 2 to 10 Represents an integer of 1,000 or less.) A triazine ring containing a repeating unit represented by any of the following formulas (21), (22), (36) and (37), having a refractive index of D-line exceeding 1.80 and containing an aniline residue polymer.

(In the formulas (21), (22), (36) and (37), n represents the number of repeating units in the polymer and represents an integer of 2 to 10,000)   The composition containing the triazine ring containing polymer and organic solvent in any one of Claims 1-4.   A composition comprising the triazine ring-containing polymer according to claim 1 and an ultraviolet curing agent.   A composition comprising the triazine ring-containing polymer according to claim 1 and a thermosetting agent.   A thin film, film, transparent plate or lens obtained using the composition according to any one of claims 5 to 7.   An electronic device, a light emitting device or an optical device comprising the thin film, film, transparent plate or lens according to claim 8.

Images