- Super alkali material and preparation method thereof, and organic light-emitting diode
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The invention discloses a super alkali material and a preparation method thereof, and an organic light-emitting diode. The super alkali material has a general structural formula as described in the specification. In the general structural formula, aromatic rings Ar1, Ar2, Ar3 and Ar4 are respectively and independently selected from substituted or unsubstituted aryl or heteroaryl groups; N is a nitrogen atom; E is the same or different, and each E is an sp2-hybridized carbon or nitrogen atom; and Cy1, Cy2, Cy3 and Cy4 are respectively and independently selected from substituted or unsubstituted heterocyclic rings. The electron injection performance of a device can be effectively improved by introducing a functional group with an alkaline acid dissociation constant (pKa), and a planar rigid structure is adopted, so the material is closely stacked to show high electron mobility, the glass-transition temperature (Tg) of the material is increased, and the stability of the device is improved. On the premise that HOMO and LUMO energy levels are maintained, injection energy barriers are reduced, turn-on voltage is reduced, and when the material serves as an electron transport material of the organic light-emitting diode, the material has the advantages of being high in carrier mobility, excellent in device performance, good in stability and the like.
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Paragraph 0056-0060
(2022/03/18)
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- Synthesis method of 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene
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The invention discloses a synthesis method of 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, which comprises the following steps: salifying 3,3'-diaminodipropylamine and a hydrobromic acid solution in tetrahydrofuran, and conducting heating and reacting with tetraethyl orthocarbonate and 3,3'-diaminodipropylamine by taking dimethyl sulfoxide as a solvent; after the reaction is finished, adding tetrahydrofuran for crystallization, and conducting suction filtration, suspension washing and drying to obtain an intermediate compound IV; then conducting reacting with sodium methoxide, conducting dissociating to obtain a crude compound V, purifying the compound V through toluene crystallization, and conducting reacting with dimethyl sulfate under the action of alkali to obtain a crude target compound VI; and carrying out reduced pressure distillation on the crude product, and collecting 80-85 DEG C/55Pa fractions to obtain colorless transparent liquid. According to the high-purity 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene prepared by the method disclosed by the invention, the GC (Gas Chromatography) purity can reach 99% or above, and the total yield is 79% or above.
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Paragraph 0019-0021; 0029-0031
(2021/08/11)
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- PROCESS FOR PREPARING BICYCLIC GUANIDINES
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Bicyclic guanidines are prepared by reacting dialkylenetriamines with dialkylcarbonates in the presence of a silane of the formula [in-line-formulae]Si(ORx)oRY(4?o) ??(IV)[/in-line-formulae] and/or their partial hydrolysates, with the proviso that contain minimally one unit IV which is a monovalent optionally substituted hydrocarbon radial with 3 to 10 carbon atoms.
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Paragraph 0103-0109
(2021/07/17)
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- PROCESS FOR THE PRODUCTION OF CYCLIC GUANIDINE DERIVATES
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The present invention relates to a process for the production of cyclic guanidine derivates of formula I or mixtures of them (formula I) by reacting a triamine in the present of a C1-source and a solid material in the gas or liquid phase under inert atmosphere.
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Page/Page column 12-13
(2021/04/30)
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- METHOD FOR PREPARING A BICYCLIC GUANIDINE AND ITS DERIVATIVES
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The present invention relates to a method of producing a bicyclic guanidine and its derivatives. In particular, the present invention relates to a method of producing triazabicyclodecene (TBD) and its derivatives, particularly alkyl derivatives, such as methyl triazabicyclodecene (MTBD), and MTBD-derived ionic liquids. The invention also relates to the use of said compounds in cellulose dissolution and subsequent processing.
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Paragraph 0054
(2019/05/30)
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- Phase transfer catalysis process for synthesizing bicyclic guanidine TBD process method (by machine translation)
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Phase transfer catalysis process for synthesizing bicyclic guanidine TBD process method. The invention provides a double (3 - aminopropyl) amine and guanidine hydrochloride as the raw material, macroporous anion-exchange resin as phase transfer catalyst in the water and oil in the two-phase solution (water - mesitylenic) synthesis of bicyclic guanidine TBD (1, 5, 7 - three-azabicyclo [4.4.0] - decyl - 5 - ene) of the new process. The process of the invention is beneficial characteristics: low reaction temperature, reaction time is short, simple and convenient operation, the phase-transfer catalyst and solvent are three toluene can be recycled and reused. (by machine translation)
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Paragraph 0020-0027; 0028-0030; 0031-0039
(2017/10/06)
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- Application to photoreactive materials of photochemical generation of superbases with high efficiency based on photodecarboxylation reactions
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A thin film of polystyrene containing 4c was spin-coated on a CaF2 plate and irradiated with 365 nm light. The absorption band arising from the carboxylate of 4c at 1372 cm-1 in the FTIR spectrum decreased after UV irradiation. Radical UV curing materials that are well established in the marketplace have drawbacks because of high volume shrinkage and oxygen inhibition. The anionically cured film showed high transparency and no volume shrinkage, in contrast to a conventional radical UV curing system, which showed large volume shrinkage. This is probably due to relatively low quantum yields for photobase generation and weaker basicity of photo-generated bases, leading to low photosensitivity of photoreactive materials sensitized with photobase generators. Furthermore, many of the photobase generators reported are generally prepared via several synthetic steps.
- Arimitsu, Koji,Endo, Ryosuke
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p. 4461 - 4463
(2014/01/06)
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- METHODS FOR PRODUCING 1,5,7-TRIAZABICYCLO[4.4.0]DEC-5-ENE BY REACTION OF A DISUBSTITUTED CARBODIIMIDE AND DIPROPYLENE TRIAMINE
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Methods for producing 1,5,7-triazabicyclo[4.4.0]dec-5-ene using a disubstituted carbodiimide, dipropylene triamine and optionally an ethereal solvent and/or an alcohol are disclosed. Use of 1,5,7-triazabicyclo[4.4.0]dec-5-ene produced by this method in an electrodepositable coating composition, and electrophoretic deposition of such coating onto a substrate to form a coated substrate, are also disclosed.
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Paragraph 0024; 0025; 0026; 0027; 0030; 0031; 0032; 0033
(2013/11/06)
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- Convenient preparation of bicyclic guanidines
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New synthesis of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) was developed from inexpensive and nontoxic chemicals. Guanidine, cyanamide, or their derivatives are heated with bis (3-aminopropyl)amine and a strong acid at 140-180 °C for 7-9 h to form TBD in 95-97% yield. Copyright Taylor & Francis Group, LLC.
- Usachev, Sergei,Gridnev, Alexei
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experimental part
p. 3683 - 3688
(2011/10/13)
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- Ti-amide catalyzed synthesis of cyclic guanidines from di-/triamines and carbodiimides
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A titanacarborane monoamide catalyzed, one-step synthesis of mono/bicyclic guanidines from commercially available di/triamines and carbodiimides is reported. The reaction mechanism is also proposed.
- Shen, Hao,Wang, Yang,Xie, Zuowei
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supporting information; experimental part
p. 4562 - 4565
(2011/10/12)
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- METHOD OF MAKING CYCLIC GUANIDINE FROM DICYANDIAMIDE AND COATING COMPOSITIONS CONTAINING SAME
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The present invention is directed to a method for preparing a cyclic guanidine comprising reacting (i) a cyanamide, (ii) a polyamine, and (iii) a weak acid. The present invention is also directed to a coating composition comprising the cyclic guanidine.
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Page/Page column 18-19
(2011/10/05)
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- CURABLE COMPOSITION
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The present invention has its object to provide a curable composition which comprises a guanidine compound as a non-organotin type catalyst, is less discolored, has good surface curability, depth curability, strength rise and adhesiveness, and can retain the curability even after storage; the above object can be achieved by a curable composition which comprises: (A) an organic polymer containing a silyl group capable of crosslinking under siloxane bond formation, the silyl group being a group represented by the general formula (1): -SiX 3 (1) (wherein X represents a hydroxyl group or a hydrolyzable group and the three X groups may be mutually the same or different), (B) a guanidine compound (B-1) as a silanol condensation catalyst, and (C) a plasticizer, wherein the content of the component (B-1) is not lower than 0.1 part by weight but lower than 8 parts by weight per 100 parts by weight of the component (A), and a non-phthalate ester plasticizer accounts for 80 to 100% by weight of the (C) component plasticizer.
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- Cyclic guanidine organic catalysts: What is magic about triazabicyclodecene?
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(Chemical Equation Presented) The bicyclic guanidine 1,5,7- triazabicyclo[4.4.0]dec-5-ene (TBD) is an effective organocatalyst for the formation of amides from esters and primary amines. Mechanistic and kinetic investigations support a nucleophilic mechanism where TBD reacts reversibly with esters to generate an acyl-TBD intermediate that acylates amines to generate the amides. Comparative investigations of the analogous bicyclic guanidine 1,4,6-triazabicyclo[3.3.0]oct-4-ene (TBO) reveal it to be a much less active acylation catalyst than TBD. Theoretical and mechanistic studies imply that the higher reactivity of TBD is a consequence of both its higher basicity and nucleophilicity than TBO as well as the high reactivity of the acyl-TBD intermediate, which is sterically prevented from adopting a planar amide structure.
- Kiesewetter, Matthew K.,Scholten, Marc D.,Kirn, Nicole,Weber, Ryan L.,Hedrick, James L.,Waymouth, Robert M.
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supporting information; experimental part
p. 9490 - 9496
(2010/03/24)
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- METHOD FOR PRODUCING BICYCLIC GUANIDINES BY USE OF A CYCLIC UREA
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The present invention is directed to a method for producing bicyclic guanidines comprising heating a cyclic urea to a temperature >200° C. to form the bicyclic guanidines.
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Page/Page column 3
(2009/12/04)
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- Bicyclic guanidinium tetraphenylborate: A photobase generator and a photocatalyst for living anionic ring-opening polymerization and cross-linking of polymeric materials containing ester and hydroxy groups
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,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) with pKa of 26.03 in acetonitrile can be effectively released by photolysis of TBD?HBPh4 salt, which represents a new family of short-wave UV photobase generators. This photobase generator enables the photoinduced living ring-opening polymerization of cyclic esters and the photoinduced cross-linking of various polymeric materials containing the hydroxyl-ester groups. Copyright
- Sun, Xun,Gao, Jian Ping,Wang, Zhi Yuan
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supporting information; experimental part
p. 8130 - 8131
(2009/02/02)
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- Process for the acrylamidoacylation of alcohols
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The present invention provides a dramatically improved process for the preparation of acrylamide and methacrylamide functional monomers, oligomers, and polymers that avoids the use of acidic catalysts which can cause undesired side reactions. The present invention process involves reacting an alkenyl azlactone with a hydroxy functional compound in the presence of a catalytic amount of either a bicyclic amidine or a trivalent phosphorus compound. These efficient basic catalysts provide unexpectedly increased reaction rates under mild conditions.
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