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DIARYLETHENE COMPOUND meetings

Foreign code F180009389
Posted date Apr 20, 2018
Country WIPO
International application number 2017JP030075
International publication number WO 2018038145
Date of international filing Aug 23, 2017
Date of international publication Mar 1, 2018
Priority data
  • P2016-165105 (Aug 25, 2016) JP
Title DIARYLETHENE COMPOUND meetings
Abstract Provided is a diarylethene compound which does not require an additional component such as an acid for color development, while suitably exerting functions such as a switching function (coloring by means of ultraviolet light irradiation), excellent stability of a colored state under visible light, and irreproducible decoloring due to temperature increase in a low temperature environment (for example, room temperature or less). A diarylethene compound which is represented by general formula (1).
Outline of related art and contending technology BACKGROUND ART
Refrigeration and refrigeration by the development of technology, the article of food or medicine or the like over a long time, quality and safety can be maintained becomes. In addition, the popularization and development of low-temperature transport technology, a variety of frozen food and refrigerated food market is also as has been circulated. For this reason, storage and distribution control the temperature of the article in the course of the step becomes important. For example, in the case where the food article, an unexpected events such as power failure, and the management cannot be a predetermined temperature, the food and bacterial growth, decay, such as a cause of the deterioration. In addition, the article is distributed internationally as the current, in the food distribution industry, the shipping of the product temperature at the equator under management (safety) is a problem.
Once the article is exposed to the conditions of controlled temperature or more to determine whether or not, only by viewing the article may be difficult to easily determined. Therefore, low-temperature storage food such as to an individual article, a temperature indicator or thermosensitive material affixed to control the temperature of the article have been tried. A temperature indicator or a thermosensitive material, the conditions of a temperature higher than the article management when subjected to discoloration, the photomask is then held over a long period, i.e. the discoloration is desirable that the irreversible type.
A temperature indicator or as a thermosensitive material, a variety of materials and application techniques have been proposed. For example, in Patent Document 1, the color former layer, the temperature detecting layer and a developer layer, low temperature non-reversible color change ('colored' or 'color' may also be referred) is the temperature history display has been proposed. Also, for example, in Patent Document 2, the dye precursor and on the support, at the time of heating the dye precursor and the reaction to form a colored color developer-sensitive recording layer containing as a main component, the permeation layer containing the pigment to binder, the melting point of 0°C or more of the temperature-sensitive material containing a microcapsule-containing layer, the protective layer are sequentially stacked has been proposed the thermochromic label.
However, Patent Document 1 to 2 and the thermochromic display or a temperature history of the label, and the temperature-sensitive agent having a melting point of the temperature-specific material is used for, after the manufacture of the label and the thermochromic display or a temperature history, state of use of the transport of up to, during storage, is maintained below a predetermined temperature is necessary. In addition, the material for the irreversible type, and the color once it, cannot be used. Therefore, these materials, the temperature changing mechanism capable of operating a switch mechanism is desirable.
Such a switch mechanism (the temperature history display material) as a material, colored by irradiation with ultraviolet light, the photochromic compound to the start of the temperature history (photochromic material) are sometimes used. For example, to Patent Document 3, the colored state, the conventional 10 times the sensitivity of the sensed temperature, the irreversible photochromic material to be decolored is disclosed. However, such a photochromic material in order to express a function, a strong acid such as trifluoromethanesulfonic acid is required. In addition, in the solid state is to express a predetermined function, it is necessary to uniformly add the acid, the acid is added, on the manufacturing steps, a serious problem.
In addition, the inventors of the present invention, described in non-patent document 1 compounds, the temperature change, ultraviolet light or visible light irradiation, it was found that discoloration are reversible. However, the compounds include, for example the surface of the article in a state in which the compound is exposed to the ultraviolet light is irradiated, is used as a temperature sensor when starting, the color is colored by the ultraviolet light irradiation, the articles in the environment, even when the visible light, even if the temperature in the, disappears. Therefore, visible light in an environment, the compound is a problem that cannot be used.
Further, the inventors of the present invention, ultraviolet light is irradiated after being colored, the colored state under visible light is extremely stable and, furthermore, from disappearing due to a irreversible by heating a compound (Patent Document 4) are found. However, the compound described in Patent Document 4 is, the half-life of a colored compound, and 30°C for about 30 at maximum, for example at a temperature lower than room temperature under a temperature change occurs in the case, little coloring is not lost. For this reason, this compound is, for example under a low temperature below room temperature is used as a temperature sensor difficult. In addition, also a compound of the non-patent document 1, under a lower temperature than room temperature when a temperature change occurs, for most color is not lost, in addition to the problems described above, difficult to use under a low temperature has a problem.
Scope of claims (In Japanese)[請求項1]
下記一般式(1)で表される、ジアリールエテン化合物。
[化1]
[式(1)中、環Aは、5員環構造または6員環構造を示しており、
Xは、S、NR7、またはOであり、R7は、水素原子またはアルキル基であり、
Y1及びY2は、それぞれ独立に、CまたはNであり、
3つのR1は、それぞれ独立に、アルキル基または芳香族基であり、
3つのR2は、それぞれ独立に、アルキル基または芳香族基であり、
R3は、Y1がCである場合には、水素原子、フェニル基、アルキル基、アルコキシ基、またはシアノ基、あるいはR4と互いに結合して環構造を形成しており、Y1がNである場合には、電子対であり、
R5は、Y2がCである場合には、水素原子、フェニル基、アルキル基、アルコキシ基、またはシアノ基、あるいはR6と互いに結合して環構造を形成しており、Y2がNである場合には、電子対であり、
R4は、水素原子、フェニル基、アルキル基、アルコキシ基、またはシアノ基、あるいはR3と互いに結合して環構造を形成しており、
R6は、水素原子、フェニル基、アルキル基、アルコキシ基、またはシアノ基、あるいはR5と互いに結合して環構造を形成している。]
[請求項2]
前記環Aが、5員環構造であり、
前記Xは、Sであり、
前記Y1及びY2が、それぞれ、Cであり、
前記R3及びR4は、それぞれ独立に、水素原子、フェニル基、または炭素数が1~5のアルキル基であるか、前記R3とR4とが互いに結合して6員環構造を形成しており、
前記R5及びR6は、それぞれ独立に、水素原子、フェニル基、または炭素数が1~5のアルキル基であるか、前記R5とR6とが互いに結合して6員環構造を形成している、請求項1に記載のジアリールエテン化合物。
[請求項3]
下記一般式(1A)で表される、請求項2に記載のジアリールエテン化合物。
[化2]
[式(1A)中、6つのZは、それぞれ独立に、水素原子またはフッ素原子であり、R1、R2、R3、R4、R5、及びR6は、それぞれ、請求項2と同じである。]
[請求項4]
下記一般式(1B)で表される、請求項3に記載のジアリールエテン化合物。
[化3]
[式(1B)中、Z、R1、R2、R3、及びR5は、それぞれ、請求項3と同じである。]
[請求項5]
下記式で表される、ジアリールエテン化合物。
[化4]
[請求項6]
請求項1~5のいずれかに記載のジアリールエテン化合物を含む、フォトクロミック材料。
[請求項7]
請求項6に記載のフォトクロミック材料を含む、光機能素子。
[請求項8]
請求項6に記載のフォトクロミック材料を含む、温度センサー。
  • Applicant
  • ※All designated countries except for US in the data before July 2012
  • OSAKA CITY UNIVERSITY
  • Inventor
  • KOBATAKE, Seiya
IPC(International Patent Classification)
Specified countries National States: AE AG AL AM AO AT AU AZ BA BB BG BH BN BR BW BY BZ CA CH CL CN CO CR CU CZ DE DJ DK DM DO DZ EC EE EG ES FI GB GD GE GH GM GT HN HR HU ID IL IN IR IS JO JP KE KG KH KN KP KR KW KZ LA LC LK LR LS LU LY MA MD ME MG MK MN MW MX MY MZ NA NG NI NO NZ OM PA PE PG PH PL PT QA RO RS RU RW SA SC SD SE SG SK SL SM ST SV SY TH TJ TM TN TR TT TZ UA UG US UZ VC VN ZA ZM ZW
ARIPO: BW GH GM KE LR LS MW MZ NA RW SD SL SZ TZ UG ZM ZW
EAPO: AM AZ BY KG KZ RU TJ TM
EPO: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR
OAPI: BF BJ CF CG CI CM GA GN GQ GW KM ML MR NE SN ST TD TG

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