JP6884748B2 - ジチオアルキルピロロピロール類および色素としてのその使用 - Google Patents
ジチオアルキルピロロピロール類および色素としてのその使用 Download PDFInfo
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- JP6884748B2 JP6884748B2 JP2018500740A JP2018500740A JP6884748B2 JP 6884748 B2 JP6884748 B2 JP 6884748B2 JP 2018500740 A JP2018500740 A JP 2018500740A JP 2018500740 A JP2018500740 A JP 2018500740A JP 6884748 B2 JP6884748 B2 JP 6884748B2
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- dithiopyrolopyrrole
- light
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- 239000000203 mixture Substances 0.000 claims description 67
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
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- YIUHGBNJJRTMIE-UHFFFAOYSA-N 1,4-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C=12C(=O)NC(C=3SC=CC=3)=C2C(=O)NC=1C1=CC=CS1 YIUHGBNJJRTMIE-UHFFFAOYSA-N 0.000 description 2
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- YPLYFEUBZLLLIY-UHFFFAOYSA-N dipropan-2-yl butanedioate Chemical compound CC(C)OC(=O)CCC(=O)OC(C)C YPLYFEUBZLLLIY-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- HPEUEJRPDGMIMY-IFQPEPLCSA-N molybdopterin Chemical compound O([C@H]1N2)[C@H](COP(O)(O)=O)C(S)=C(S)[C@@H]1NC1=C2N=C(N)NC1=O HPEUEJRPDGMIMY-IFQPEPLCSA-N 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
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- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
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Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
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Description
R1、R2、R3およびR4は互いに独立に、1〜20個の炭素原子を有し直鎖状もしくは分岐状でハロゲンで置換されてよいアルキル基またはハロゲンを表し、
Q1およびQ2は、それぞれ単結合を表すか、互いに独立にO、OCF2、CF2、CF2CF2またはCOを表し、
A1、A2、A3およびA4は、それぞれ単結合を表すか、互いに独立にフェニレン、ピリジン、ピリミジン、ピリダジン、ナフタレン、チオフェン、セレノフェンおよびチアゾールから成る群より選択される基を表し、
ただし(i)少なくともA3およびA4は芳香族環構造を表し、
(ii)芳香族環構造はハロゲン化物で置換されてよい
ことを条件とし、および
Z1、Z2、Z3、Z4、Z5およびZ6は、それぞれ単結合を表すか、互いに独立にC≡C、CH=CH、CF=CF、CF=CH、CH2CH2、CF2−CF2およびCF2Oから成る群より選択される基を表し、
ただし(iii)少なくともZ3およびZ4は単結合またはπ共役基のいずれかを表すことを条件とする。
(i)R1、R2、R3およびR4は互いに独立に、6〜12個の炭素原子を有する分岐状のアルキル基を表し、および/または
(ii)3個、4個または5個の芳香族環構造が存在しており、および/または
(iii)芳香族環構造はハロゲン化物で置換されている
式(1)の誘導体が好ましい。
ジチオピロロピロール誘導体の調製としては一般に、下のスキームDに記載できる。
また本発明の更なる実施形態において本発明によるジチオピロロピロール誘導体は、混合物の構成成分でもよい。
本発明による混合物は特に、液晶化合物を含む。混合物は、好ましくは3〜25種類の異なる液晶化合物、好ましくは8〜18種類、特に好ましくは12〜16種類の異なる液晶化合物を含む。液晶化合物は好ましくは、混合物の主成分を表す。液晶化合物は混合物中に合わせて、特に好ましくは90〜99.99重量%、特に好ましくは93〜99.9重量%、非常に特に好ましくは95〜99.8重量%の割合で存在する。
本発明による混合物は、更に好ましくは、1種類以上のキラルドーパントを含む。キラルドーパントは、好ましくは、0.01〜3重量%、特に好ましくは0.05〜1重量%の総濃度で、本発明による混合物中で使用する。また、デバイス中の混合物を使用する際に高い値のツイストを得るために、キラルドーパントの総濃度を、3重量%より高く、好ましくは最大10重量%までで選択してよい。
本発明による混合物は、更に好ましくは、1種類以上の安定剤を含む。安定剤の総濃度は、好ましくは混合物の0.00001および10重量%の間、特に好ましくは0.0001および1重量%の間である。
少なくとも1種類の式(1)の化合物および液晶化合物から選択される少なくとも1種類の化合物に加え、本発明による混合物は、好ましくは、式(1)と異なる構造を有する1種類以上の色素化合物を含む。本発明による混合物は、特に好ましくは、式(1)と異なる構造を有する1種類、2種類、3種類または4種類の色素化合物、非常に特に好ましくは、式(1)と異なる構造を有する2種類または3種類の色素化合物を含む。これらの色素化合物は、好ましくは、二色性色素化合物である。これらの色素化合物は、更に好ましくは、蛍光色素化合物である。
下記の通り本発明は更に、本発明による色素の産業上の利用可能性に関する。
第1の実施形態において本発明は室内への光の進入を制御するためのデバイスにおける、式(1)のジチオピロロピロール誘導体の使用を包含する。
・基板層、
・導電性透明層、
・配向層
・ジチオピロロピロール誘導体を含むスイッチ層
・配向層
・導電性透明層、
・基板層。
本発明は更に、式(1)のジチオピロロピロール誘導体の、
(i)電子部品中の半導体または増感剤として、ただしこれらは好ましくは太陽電池、ダイオードおよびトランジスタから成る群より選択される。本明細書においては、LED、OLED、LETおよびOLETについて具体的に言及でき、
(ii)特に車両製造において用いることができるポリマー例えば、ポリマーフィルムの着色のために、
(iii)「ゲスト−ホスト」LCD用途における
使用に関する。
<3,6−ジ(チオフェン−2−イル)ピロロ[3,4−c]ピロール−1,4(2H,5H)−ジオン(DKPP)(2)の調製>
前駆体(2)を、以下の反応スキーム(I)に従って調製する。
<3,6−ジ(チオフェン−2−イル)ピロロ[3,4−c]ピロール−1,4(2H,5H)−ジチオン(DTPP)(3)の調製>
前駆体(3)を、以下の反応スキーム(II)に従って調製する。
<3,6−ジ(チオフェン−2−イル)ピロロ[3,4−c]ピロール−[ジ−Br−ジ−S−EtHex−DTTP](5)の調製>
前駆体(5)を、以下の反応スキーム(IV)に従って調製する。
<1,4−ビス−(5−(4−(3−エチルヘプチル)−2−フルオロフェニル)チオフェン−2−イル)−3,6−ビス((2−エチルヘキシル)チオ)ピロロ[3,4−c]ピロール(6)の調製>
本発明による生成物(6)を、以下の反応スキーム(V)に従って調製する。
上および下において、
Δnは、20℃および589nmで測定する光学的異方性を表し、
neは、20℃および589nmで測定する異常光屈折率を表し、
noは、20℃および589nmで測定する常光屈折率を表し、
Δεは、20℃および1kHzで測定する誘電異方性を表し、
cl.p.、T(N,I)は、透明点(℃)を表す。
以下の組成の混合物を調製する:
99.588%の基礎混合物
0.178%の色素1
0.048%の色素2
0.162%の色素3
0.024%の色素4。
Claims (17)
- 式(1)のジチオピロロピロール誘導体を含み、室内への光の進入を制御するデバイス。
R1、R2、R3およびR4は互いに独立に、6〜12個の炭素原子を有する分岐状のアルキル基を表し、
Q1およびQ2は、それぞれ単結合を表すか、互いに独立にO、OCF2、CF2、CF2CF2またはCOを表し、
A1、A2、A3、A4、A5およびA6は、それぞれ単結合を表すか、互いに独立にフェニレン、ピリジン、ピリミジン、ピリダジン、ナフタレン、チオフェン、セレノフェンおよびチアゾールから成る群より選択される基を表し、
ただし(i)少なくともA3およびA4は芳香族環構造を表さなければならず、
(ii)芳香族環構造はハロゲン化物で置換されてよい
ことを条件とし、および
Z1、Z2、Z3、Z4、Z5およびZ6は、それぞれ単結合を表すか、互いに独立にC≡C、CH=CH、CF=CF、CF=CH、CH2CH2、CF2−CF2およびCF2Oから成る群より選択される基を表し、
ただし(iii)少なくともZ3およびZ4は単結合またはπ共役基のいずれかを表すことを条件とする。) - 式(1)の化合物は、3個、4個または5個の芳香族環構造を含有することを特徴とする請求項1に記載のデバイス。
- 式(1)の化合物において芳香族環構造は、フッ化物で置換されていることを特徴とする請求項1または2に記載のデバイス。
- 式(1)のジチオピロロピロール誘導体を含み、室内への光の進入を制御するデバイス。
R1、R2、R3およびR4は互いに独立に、6〜12個の炭素原子を有する分岐状のアルキル基を表し、
Q1およびQ2は、それぞれ単結合を表すか、互いに独立にO、OCF2、CF2、CF2CF2またはCOを表し、
A1、A2、A3、A4、A5およびA6は、それぞれ単結合を表すか、互いに独立にフェニレン、ピリジン、ピリミジン、ピリダジン、ナフタレン、チオフェン、セレノフェンおよびチアゾールから成る群より選択される基を表し、
ただし(i)A1〜A3の少なくとも1つはフルオロフェニレンであり、A1〜A3の他の少なくとも1つはチオフェンジイルであり、
(ii)A4〜A6の少なくとも1つはフルオロフェニレンであり、A4〜A6の他の少なくとも1つはチオフェンジイルである
ことを条件とし、および
Z1、Z2、Z3、Z4、Z5およびZ6は、それぞれ単結合を表すか、互いに独立にC≡C、CH=CH、CF=CF、CF=CH、CH2CH2、CF2−CF2およびCF2Oから成る群より選択される基を表し、
ただし(iii)少なくともZ3およびZ4は単結合またはπ共役基のいずれかを表すことを条件とする。) - 請求項1および4〜8において定義されるジチオピロロピロール誘導体は、200℃より低い温度で中間相を有することを特徴とする請求項1〜8のいずれか1項に記載のデバイス。
- 室内への光の進入を制御するデバイスにおいて使用するための混合物であって、
(a)少なくとも1種類の請求項1および4〜8において定義されるジチオピロロピロール誘導体および
(b1)少なくとも1種類の液晶化合物および/または
(b2)少なくとも1種類のキラルドーパントおよび/または
(b3)少なくとも1種類の安定剤および/または
(b4)少なくとも1種類の、式(1)のものとは異なる好ましくは同種の二色性色素
を含む混合物。 - 室内への光の進入を制御するデバイスにおける、請求項1および4〜8において定義されるジチオピロロピロール誘導体の使用。
- 以下の層順序を有し、
・基板層、
・導電性透明層、
・配向層
・請求項1および4〜8において定義されるジチオピロロピロール誘導体を含むスイッチ層
・配向層
・導電性透明層、
・基板層
ただし更なる層が追加して存在してもよいことを特徴とする請求項1〜9のいずれか1項に記載のデバイス。 - 請求項1〜9のいずれか1項に記載のデバイスを含有する窓。
- 電子部品における半導体または増感剤としての、請求項1および4〜8において定義されるジチオピロロピロール誘導体の使用。
- これらの部品が、太陽電池、ダイオードおよびトランジスタから成る群より選択されることを特徴とする請求項14に記載の使用。
- ポリマーの着色のための、請求項1および4〜8において定義されるジチオピロロピロール誘導体の使用。
- 「ゲスト−ホスト」LCD用途における、請求項1および4〜8において定義されるジチオピロロピロール誘導体の使用。
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US10868257B2 (en) | 2020-12-15 |
KR102602326B1 (ko) | 2023-11-16 |
TW201710262A (zh) | 2017-03-16 |
EP3319964B1 (de) | 2020-07-22 |
TWI717368B (zh) | 2021-02-01 |
CN107849048B (zh) | 2021-05-25 |
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