PL433405A1 - 2,3-bis[7-(N-carbazolyl)-9,9-dibutylfluoren-2-yl]-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide and its preparation - Google Patents
2,3-bis[7-(N-carbazolyl)-9,9-dibutylfluoren-2-yl]-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide and its preparationInfo
- Publication number
- PL433405A1 PL433405A1 PL433405A PL43340520A PL433405A1 PL 433405 A1 PL433405 A1 PL 433405A1 PL 433405 A PL433405 A PL 433405A PL 43340520 A PL43340520 A PL 43340520A PL 433405 A1 PL433405 A1 PL 433405A1
- Authority
- PL
- Poland
- Prior art keywords
- bis
- dibutylfluoren
- carbazolyl
- ethylhexyl
- ghi
- Prior art date
Links
- KJOLVZJFMDVPGB-UHFFFAOYSA-N perylenediimide Chemical compound C=12C3=CC=C(C(NC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)NC(=O)C4=CC=C3C1=C42 KJOLVZJFMDVPGB-UHFFFAOYSA-N 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- 125000005605 benzo group Chemical group 0.000 title 1
- -1 N-carbazolyl Chemical group 0.000 abstract 4
- 229910000071 diazene Inorganic materials 0.000 abstract 4
- LQIRQSNFLPMJLT-UHFFFAOYSA-N C(C)C(CC1=CC=2C=3C4=C1C=CC1=CC=CC(C5=CC=CC(=CC=2)C=35)=C14)CCCC Chemical group C(C)C(CC1=CC=2C=3C4=C1C=CC1=CC=CC(C5=CC=CC(=CC=2)C=35)=C14)CCCC LQIRQSNFLPMJLT-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- 238000006352 cycloaddition reaction Methods 0.000 abstract 3
- JOURFFJRFPWMLJ-UHFFFAOYSA-N CCCCC1(CCCC)C2=CC(N3C4=CC=CC=C4C4=C3C=CC=C4)=CC=C2C(C=C2)=C1C=C2C#CC(C=C1)=CC(C(CCCC)(CCCC)C2=C3)=C1C2=CC=C3N1C2=CC=CC=C2C2=C1C=CC=C2 Chemical group CCCCC1(CCCC)C2=CC(N3C4=CC=CC=C4C4=C3C=CC=C4)=CC=C2C(C=C2)=C1C=C2C#CC(C=C1)=CC(C(CCCC)(CCCC)C2=C3)=C1C2=CC=C3N1C2=CC=CC=C2C2=C1C=CC=C2 JOURFFJRFPWMLJ-UHFFFAOYSA-N 0.000 abstract 2
- 238000004587 chromatography analysis Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 239000000758 substrate Substances 0.000 abstract 2
- PXXHQTTXAFOJNY-UHFFFAOYSA-N C(C)C(CC1=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)CCCC Chemical group C(C)C(CC1=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)CCCC PXXHQTTXAFOJNY-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 239000002086 nanomaterial Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Abstract
Przedmiotem wynalazku jest 2,3-bis[7-(N-karbazolilo)-9,9-dibutylofluoren-2-ylo]-N,N'bis(2-etyloheksylo)benzo[ghi]perylenodiimid przedstawiony wzorem 1 oraz sposób jego otrzymywania pokazany na schemacie 1, polegający na tym, że przeprowadza się proces cykloaddycji 1,2-bis[7-(N-karbazolilo)-9,9-dibutylofluoren-2-ylo]acetylenu do wnęki N,N'-bis(2-etyloheksylo)perylenodiimidu z równoczesną eliminacją wodoru, w taki sposób że do reaktora odpornego na nadciśnienie, korzystnie co najmniej do 5 atmosfer, wprowadza się — w dowolnej kolejności - N,N'-bis(2-etyloheksylo)perylenodiimid oraz 1,2-bis[7-(N-karbazolilo)-9,9-dibutylofluoren-2-ylo]acetylen w proporcjach molowych od 1:1 do 1:10, reaktor zamyka się i wytwarza w nim próżnię, to jest ciśnienie o wartości nie wyższej niż 0,1 Pa, co zapewnia praktycznie usunięcie tlenu i lotnych substancji, po czym prowadzi się reakcję w temperaturze od 260 do 300°C, przez czas nie krótszy niż 24 godziny. Po zakończeniu reakcji cykloaddycji 2,3-bis[7-(N-karbazolilo)-9,9-dibutylofluoren-2-ylo]-N,N'-bis(2-etyloheksylo)benzo[ghi]perylenodiimid wydziela się chromatograficznie, na żelu krzemionkowym, eluując wpierw nieprzereagowany substrat acetylenowy, a następnie produkt - wszystko za pomocą chlorku metylenu. Korzystnie, finalnie produkt oczyszcza się do poziomu > 98% za pomocą ponownej chromatografii lub krystalizacji uzyskując 2,3-bis[7-(N-karbazolilo)-9,9-dibutylofluoren-2-ylo]-N,N'-bis(2-etyloheksylo)benzo[ghi]perylenodiimid z wydajnością do 25%. Produkt reakcji może być luminoforem, prekursorem nanografenów lub nanomateriałów dla organicznej elektroniki, składnikiem warstw aktywnych, na przykład w OLED-ach lub substratem dla dalszych cykloaddycji lub cyklo-dehydrokondensacji.The present invention relates to 2,3-bis [7- (N-carbazolyl) -9,9-dibutylfluoren-2-yl] -N, N'bis (2-ethylhexyl) benzo [ghi] perylene diimide represented by the formula 1 and a method for its preparation shown in Scheme 1, which consists in carrying out the cycloaddition process of 1,2-bis [7- (N-carbazolyl) -9,9-dibutylfluoren-2-yl] acetylene into the N, N'-bis (2- ethylhexyl) perylene diimide with simultaneous elimination of hydrogen, such that N, N'-bis (2-ethylhexyl) perylenediimide and 1,2-bis [7- (N-carbazolyl) -9,9-dibutylfluoren-2-yl] acetylene in molar proportions from 1: 1 to 1:10, the reactor is closed and a vacuum is created in it, i.e. a pressure of no more than 0 , 1 Pa, which practically removes oxygen and volatile substances, and then the reaction is carried out at a temperature of 260 to 300 ° C for a time not shorter than 24 hours. After the cycloaddition reaction is complete, 2,3-bis [7- (N-carbazolyl) -9,9-dibutylfluoren-2-yl] -N, N'-bis (2-ethylhexyl) benzo [ghi] perylene diimide is separated by chromatography, silica gel, eluting first the unreacted acetylene substrate and then the product - all with methylene chloride. Preferably, the final product is finally purified to> 98% by re-chromatography or recrystallization to afford 2,3-bis [7- (N-carbazolyl) -9,9-dibutylfluoren-2-yl] -N, N'-bis ( 2-ethylhexyl) benzo [ghi] perylene diimide with a yield of up to 25%. The reaction product may be a phosphor, a nanografen or nanomaterials precursor for organic electronics, a component of active layers, for example in OLEDs, or a substrate for further cycloaddition or cyclo-dehydrocondensation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL433405A PL241963B1 (en) | 2020-03-31 | 2020-03-31 | 2,3-bis[7-(N-carbazolyl)-9,9-dibutylfluoren-2-yl]-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL433405A PL241963B1 (en) | 2020-03-31 | 2020-03-31 | 2,3-bis[7-(N-carbazolyl)-9,9-dibutylfluoren-2-yl]-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL433405A1 true PL433405A1 (en) | 2021-10-04 |
| PL241963B1 PL241963B1 (en) | 2023-01-02 |
Family
ID=78055900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL433405A PL241963B1 (en) | 2020-03-31 | 2020-03-31 | 2,3-bis[7-(N-carbazolyl)-9,9-dibutylfluoren-2-yl]-N,N'-bis(2-ethylhexyl)benzo[ghi]perylenediimide and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL241963B1 (en) |
-
2020
- 2020-03-31 PL PL433405A patent/PL241963B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL241963B1 (en) | 2023-01-02 |
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