CN101560211B - Preparation for 1,2,4-triazolo[1,5-a]pyrimidine-2-ethyl thioether monosubstituted derivative and application thereof - Google Patents
Preparation for 1,2,4-triazolo[1,5-a]pyrimidine-2-ethyl thioether monosubstituted derivative and application thereof Download PDFInfo
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Abstract
The invention discloses preparation for a 1,2,4-triazolo[1,5-a]pyrimidine-2-ethyl thioether monosubstituted derivative with a general formula (1) and application thereof. In the formula, Ar is ferrocenyl, triphenylamine, N-hexyl carbazyl, 6-bromine-N-hexyl carbazyl, 4-(N,N-bis p-bromine diphenyl)aminophenyl or N,N-dimethylamino benzyl. The compound has good solubility and thermal stability, can beused as a blue, green or red electroluminescent material, and can be applied to a flat-panel display.
Description
Technical field
The invention belongs to photoluminescence and electroluminescent technology field, be specifically related to a class 1,2, the preparation of 4-triazolo [1,5-a] pyrimidine-2-ethyl thioether monosubstituted derivative and the application in organic flat-panel monitor thereof as photoluminescence and electroluminescent material.This compounds has good solubility and thermostability, can be used as blueness or green light photoluminescence and electroluminescent material, is applied in the flat-panel monitor.
Background technology
Triazolo pyrimidine class Hete rocyclic derivatives is owing to contain triazole and the important active structure unit of this two class of pyrimidine simultaneously in its molecular structure, thereby shown wide biological activity [1], having obtained using widely [1] at agricultural chemicals and medicine and other fields, is the hot fields of current novel pesticide research and development.For example, people such as Berecz have reported 7-chloro-5,6-cyclohexyl-1,2, and 4-triazolo [1,5-a] pyrimidine-2-sulphur methyl ether has gastric acid inhibitory excretory function [1], in addition, and 1,2,4-triazolo [1,5-a] pyrimidine also has good weeding and fungicidal activity [1].And the pyridine derivatives with fungicidal activity has also been obtained more patent, as RPA407213 (2001), US6002016 (1999), GB2329180 (1999).But 1,2,4-triazolo [1,5-a] pyrimidine-2-ethyl thioether derivative is not seen any report as yet as photoluminescence and electroluminescent material.
Organic electroluminescent (Electroluminescence is called for short EL) began one's study at the initial stage sixties in last century.1963, people such as Pope [2] at first reported the electro optical phenomenon of anthracene single crystal, and they as luminescent layer, apply the driving voltage of 400V with the anthracene crystal at two ends, observe the blue-light-emitting of anthracene.Up to the later stage 1980s, organic electroluminescent research has just had breakthrough progress, and 1987, [3] such as the Tang of Kodak used oxine aluminium (Alq
3) unformed film realized the organic molecule bilayer structure electroluminescent device of high brightness, high-level efficiency, low driving voltage, driving voltage is 10V only, efficient 1.51m/W, and brightness is up to 1000cd/m
2, the life-span of device is 100h in helium atmosphere.This breakthrough has caused various countries scholars' very big concern.People [4] such as nineteen ninety Brroughes have reported the polymer LED of vinylbenzene (PPV) being made of poly-, and it has, and making is simple, the energy efficiency advantages of higher.The research of polymer P PV and PPV derivant material has further promoted the research of Organic Light-Emitting Display thus, and these work have all greatly promoted the development of luminescent device, thereby the research of organic electroluminescent is worldwide extensively carried out.Organic light emitting diode (Organic light-emitting devices by the electroluminescent organic material preparation, OLED) flat-panel monitor that can be made into, have low dc voltage driving, high brightness, high-level efficiency, manufacture craft and simply and easily realize advantages such as panchromatic big area demonstration, generally believed the strongest rival for being flat panel display of new generation.Organic EL device has the characteristic of the DC low-voltage driving that is complementary with unicircuit, and is easy to realize that big area shows; Compare with LCD, its response speed is fast; Compare with inorganic device, organic EL device has easy processing, can be processed into different shape, satisfactory mechanical property and low cost and other advantages.
Though organic electroluminescent has been obtained amazing development, many high performance electroluminescent materials are developed out, the organic EL display device of commercialization also constantly occurs, and the advantage that still want to possess the efficient height simultaneously, cost is low, stability is high, the life-span is long also has many difficulties.According to the relation of luminescence mechanism and structure and performance, scientist and industrial community just actively attempt to develop new and effective stable electroluminescent material at present, to satisfy the colored needs that show of RGB three primary colours; Study new and effective blue light, ruddiness, white light material and also remain one of focus of present organic electroluminescent research.
Under this research background, the present invention has developed and can be used as 1,2 of novel strong luminescent material just, 4-triazolo [1,5-a] pyrimidine-2-ethyl thioether derivative.This patent has prepared a series of with 1,2, and 4-triazolo [1,5-a] pyrimidine is the compound of the conjugated structure of center acceptor, their structure is characterized, and studied their photoluminescence performance.Its design philosophy is: as strong acceptor, itself and different aromatic aldehyde reactions are obtained the different electron donor organic compound that have of the easy modification of D-π-A type structure with this triazolo pyrimidine heterocycle.Absorb and the photoluminescence performance by testing its ultraviolet-visible, prove that they have fluorescence from the blueness to the green, the part of compounds fluorescence quantum yield is higher, and the result shows that these compounds are the organic electroluminescent novel materials with potential using value.
Reference:
1
1、Kleschick，W.A.；Costales，M.J.；Dunbar，J.E.Pestic.Sci.1990，29(3)，341-355.
1
2、Shankar，R.B.J.Heterocyclic.Chem.1993，30(2)，169-171.
1
3、Kleschick，W.A.；Costales，M.J.；Gerwick，B.C.etal.Am.Chem.Soc.1992，1016.
1
4、Kleschick，W.A.；Costales，M.J.；Gerwick，B.C.etal.Am.Chem.Soc.1992，17-25.
1
5、Tominaga，Y.；Sakai，S.Chem.Pharm.Bull.1985，33，962-970.
1
6、Kleschick，W.；Costales，M.J.；Dunber，J.E.etal，Pesticsci.1990，29，341-355.
1
7, Sun Guoxiang, Jiang Xuliang, Wang Yuhua, Shen Delong, modern agricultural chemicals, 2005,4 (1), 14-16.
1
8, imperial Deqing, Wang Yangang, Li Dejiang, king's sharp point, organic chemistry, 2005,25,1498-1502.
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9、Sukata，S.Chem.Soc.Jpn.1983，56，280.
2、PoPe，M.；Kallmann，H.P.；Magnante，P.J.Chem.Phys..1963，38，2042-2043.
3、Tang，C.W.；VanSylek，S.A.Appl.Phys.Lett.1987，51，913-915.
4、Burroughs，J.H.；Bradley，D.D.C.；Brown，A.R.；Marks，R.N.；Maekay，K.；Friend，R.H.；Burn，P.L.；Holmes，A.B.，Nature.1990，347，539-541.
Summary of the invention
The objective of the invention is to explore the compound of good light photoluminescence and electroluminescent properties, provide to have 1,2 of the characteristics of luminescence, 4-triazolo [1,5-a] pyrimidine-2-ethyl thioether monosubstituted derivative.
The present invention proposes 1,2,4-triazolo [1,5-a] pyrimidine-2-ethyl thioether derivative (1):
Ar is ferrocenyl, N in the formula (1), N-dimethylamino phenmethyl, triphen amido, N-hexyl carbazyl, 6-bromo-N-hexyl carbazyl or 4-(N, N-biconjugate bromine phenylbenzene) aminophenyl.
The compound of above-mentioned formula provided by the invention (1) has good photoluminescence and electroluminescent properties, as blueness or green light photoluminescence and electroluminescent material, is applied to can be made into Organic Light Emitting Diode in the flat-panel monitor.
With general formula (1) represented 1,2,4-triazolo [1,5-a] preparation of pyrimidine-2-ethyl thioether derivative, be to make represented compound of general formula (I) and aryl aldehyde ArCHO (II), by Knoevenagel condensation reaction (1) compound of expressing that obtains having general formula
Ar is identical with the definition in the formula (1) in the formula (II),
In the above-mentioned reaction, with n-propyl alcohol (n-propanol) is solvent, piperidines (the piperidine that adds catalytic amount, piperidine), make the represented compound of 1 mole general formula (I) and the represented compound of ArCHO of 2.1 times of moles, Ar is a ferrocenyl, the triphen amido, N-hexyl carbazyl, 6-bromo-N-hexyl carbazyl or 4-(N, N-biconjugate bromine phenylbenzene) aminophenyl, stirring and refluxing (Reflux) reaction 2 days, after having reacted, slough solvent, adopt 300-400 order silica gel chromatographic column to purify, the second colour band compound that obtains is represented derivative (the compound 1a of general formula (1), 1b, 1c, 1d and 1e).
Equally, make the represented compound of 1 mole general formula (I) and the N of 1.1 times of moles, N-dimethylaminobenzaldehyde stirring and refluxing reaction 2 days, after having reacted, slough solvent, adopt silica gel (300-400 order) chromatographic column to purify, the first colour band compound that obtains is the represented derivative of general formula (1) (compound 1f).
Description of drawings
Fig. 1 compound 1a, 1b, 1c, 1d, 1e and the 1f ultraviolet-visible in chloroformic solution absorbs figure
The fluorescent emission figure of Fig. 2 compound 1a, 1b, 1c, 1d, 1e and 1f
Embodiment
Be described more specifically the preparation and the illumination effect of compound in (1) of the present invention formula below by example.
The preparation of compound 1a:
Be equipped with at 50mL and add 0.2g 5 in the round-bottomed flask of reflux condensing tube, 7-dimethyl-1,2,4-triazolo [1,5-a] pyrimidine-2-ethyl thioether and 2.1 mol ratio ferrocene list aldehyde add the dissolving of 20mL n-propyl alcohol, drip 0 of piperidinyl-1, and heated and stirred refluxed 2 days.After its cooling, underpressure distillation boils off solvent, and drying is dissolved it with chloroform, adopts silica gel (300-400 order) chromatographic column purification (eluent: chloroform: ethyl acetate=1: 1 (volume ratio)).Second colour band is red-purple solid chemical compound 1a (0.28g, a productive rate 78%), m.p.178～179 ℃.
Ultimate analysis: measured value C% 59.41 H% 4.98 N% 13.86 S%7.93;
Calculated value C% 59.53 H% 4.87 N% 13.58 S%8.09.
IR(cm
-1)1657(C＝C)，956(C＝C)。
1HNMR(CDCl
3，400MHz)δ：7.96(d，1H，J＝15.0HZ，-CH＝CH-)，7.08(d，1H，J＝15.0HZ，-CH＝CH-)，6.94(s，1H，Py)，4.65(s，2H，Ar)，4.52(s，2H，Ar)，4.20(s，5H，Ar)，3.35(m，2H，J＝4.8HZ，S-CH
2)，2.66(s，3H，Py-CH
3)，1.51(t，3H，J＝7.2HZ，S-CH
2-CH
3)。
Embodiment 2
The preparation of compound 1b:
Be equipped with at 50mL and add 0.2g 5,7-dimethyl-1,2 in the round-bottomed flask of reflux condensing tube; 4-triazolo [1,5-a] pyrimidine-2-ethyl thioether and 2.1 mol ratio 3-formyl radicals-N-hexyl carbazole add the dissolving of 20mL n-propyl alcohol; drip 0 of piperidinyl-1, heated and stirred refluxed 2 days.After its cooling, thick product with its evaporate to dryness, dissolves back silica gel (300-400 order) chromatographic column purification (eluent: chloroform: ethyl acetate=15: 1 (volume ratio)) with chloroform under reduced pressure.Second colour band is yellow solid compound 1b (0.11g, a productive rate 26%), m.p.158～160 ℃.
Ultimate analysis: measured value C% 71.61 H% 6.65 N% 14.86 S% 6.51;
Calculated value C% 71.35 H% 6.74 N% 14.91 S%6.83.
IR(cm
-1)1632(C＝C)，958(C＝C)。
1HNMR(CDCl
3，400MHz)δ：8.16(m，2H，-CH＝CH-and?Ar)，7.78(d，1H，J＝8.8Hz，Ar)，7.56(d，1H，J＝16.4Hz，-CH＝CH-)，7.43(m，4H，Ar)，7.04(s，1H，Py-H)，6.70(s，1H，Ar)，4.29(m，2H，J＝7.2Hz，N-CH
2)，3.37(m，2H，J＝7.6Hz，S-CH
2)，2.65(s，3H，Py-CH
3)，1.89(m，2H，CH
2)，1.51(t，3H，J＝7.6Hz，S-CH
2-CH
3)，1.30(m，6H，CH
2)，0.87(t，3H，J＝6.8Hz，CH
3)。
MS(70eV)m/z：470.2(100)。
Embodiment 3
The preparation of compound 1c:
Be equipped with at 50mL and add 0.2g 5,7-dimethyl-1,2 in the round-bottomed flask of reflux condensing tube; 4-triazolo [1,5-a] pyrimidine-2-ethyl thioether and 2.1 mol ratio 6-bromo-3-formyl radical-N-hexyl carbazoles add the dissolving of 20mL n-propyl alcohol; drip 0 of piperidinyl-1, heated and stirred refluxed 2 days.After its cooling, thick product with its evaporate to dryness, dissolves back silica gel (300-400 order) chromatographic column purification (eluent: chloroform: ethyl acetate=15: 1 (volume ratio)) with chloroform under reduced pressure.Second colour band is yellow solid compound 1c (0.19g, a productive rate 36%), m.p.147～149 ℃.
Ultimate analysis: measured value C% 61.31 H% 5.51 N% 12.77 S% 5.85;
Calculated value C% 61.29 H% 5.72 N% 12.65 S%5.54.
IR(cm
-1)1631(C＝C)，958(C＝C)。
1HNMR(CDCl
3，400MHz)δ：8.28(m，3H，-CH＝CH-and?Ar)，7.83(d，1H，J＝8.4Hz，Ar-H)，7.55(t，2H，Py-H?and?Ar)，7.44(d，1H，J＝6.0Hz，Ar-H)，7.30(d，1H，J＝7.2Hz，Ar-H)，7.08(d，1H，J＝13.2Hz，-CH＝CH-)，4.29(d，2H，J＝6.0Hz，N-CH
2)，3.38(d，2H，J＝7.2Hz，S-CH
2)，2.70(s，3H，Py-CH
3)，1.87(t，2H，J＝4.8Hz，CH
2)，1.53(t，3H，J＝7.2Hz，S-CH
2-CH
3)，1.30(m，6H，CH
2)，0.87(t，3H，J＝7.2Hz，CH
3)。
MS(70eV)m/z：549.1(100)。
Embodiment 4
The preparation of compound 1d:
Be equipped with at 50mL and add 0.2g 5 in the round-bottomed flask of reflux condensing tube, 7-dimethyl-1,2,4-triazolo [1,5-a] pyrimidine-2-ethyl thioether and 2.1 mol ratio triphenylamine list aldehyde add the dissolving of 20mL n-propyl alcohol, drip 0 of piperidinyl-1, and heated and stirred refluxed 2 days.After its cooling, underpressure distillation boils off solvent, and drying is dissolved it with chloroform, adopts silica gel (300-400 order) chromatographic column purification (eluent: chloroform: ethyl acetate=20: 1 (volume ratio)).Second colour band is orange red solid chemical compound 1d (0.07g, a productive rate 15%), m.p.198～199 ℃.
Ultimate analysis: measured value C% 72.54 H% 5.44 N% 15.11 S% 6.92;
Calculated value C% 72.29 H% 5.52 N% 15.34 S%
6.65。IR(cm
-1)1631(C＝C)，956(C＝C)。
1HNMR(CDCl
3，400MHz)δ：7.50(d，1H，J＝8.8Hz，Ar)，7.37(d，1H，J＝16.4Hz，-CH＝CH-)，7.32(m，3H，J＝8.0Hz，Ar)，7.22(t，2H，J＝8.0Hz，Ar)，7.04(d，2H，J＝8.8Hz，Ar)，6.99(m，2H，Py-H?and-CH＝CH-)，6.88(d，2H，J＝7.6HZ，Ar)，6.74(t，2H，Ar)，3.32(m，2H，S-CH
2)，3.27(m，3H，Py-CH
3)，1.46(t，3H，J＝7.2Hz，S-CH
2-CH
3)。
MS(70eV)m/z：463.5(100)。
Embodiment 5
The preparation of compound 1e:
Be equipped with at 50mL and add 0.2g 5,7-dimethyl-1,2 in the round-bottomed flask of reflux condensing tube, 4-triazolo [1,5-a] pyrimidine-2-ethyl thioether and 2.1 mol ratio 4-(N, N-biconjugate bromine phenylbenzene) aminobenzaldehyde, add the dissolving of 20mL n-propyl alcohol, drip 0 of piperidinyl-1, heated and stirred refluxed 2 days.After its cooling, underpressure distillation boils off solvent, and drying is dissolved it with minimum of chloroform, adopts silica gel (300-400 order) chromatographic column purification (eluent: chloroform: ethyl acetate=5: 1 (volume ratio)).Second colour band is orange red solid chemical compound 1e (0.12g, a productive rate 40%), m.p.171～173 ℃.
Ultimate analysis: measured value C% 54.12 H% 3.37 N% 11.27 S% 5.16;
Calculated value C% 54.48 H% 3.01 N% 10.96 S%5.35.
IR(cm
-1)1628(C＝C)，958(C＝C)。
1HNMR(CDCl
3，400MHz)δ：7.97(d，2H，J＝16.0Hz，-CH＝CH-)，7.52(d，2H，J＝8.8Hz，Ar)，7.38(m，4H，Ar?and-CH＝CH-)，7.01(m，6H，Ar)，6.73(t，1H，Py-H)，3.30(m，2H，S-CH
2)，2.72(s，3H，Py-CH
3)，1.49(t，3H，J＝7.6Hz，S-CH
2-CH
3)。
Embodiment 6
The preparation of compound 1f:
Be equipped with at 50mL and add 0.2g 5,7-dimethyl-1,2 in the round-bottomed flask of reflux condensing tube, 4-triazolo [1,5-a] pyrimidine-2-ethyl thioether and 1.1 mol ratio N, N-Dimethylaminobenzene list aldehyde, add the dissolving of 20mL n-propyl alcohol, drip 0 of piperidinyl-1, heated and stirred refluxed 2 days.After its cooling, underpressure distillation boils off solvent, and drying is dissolved it with chloroform, adopts silica gel (300-400 order) chromatographic column purification (eluent: chloroform: ethyl acetate=2: 1 (volume ratio)).First colour band is red solid compound 1f (0.34g, a productive rate 75%), m.p.181～183 ℃.
Ultimate analysis: measured value C% 63.69 H% 6.24 N% 20.63 S%9.45;
Calculated value C% 63.48 H% 6.53 N% 20.94 S%9.62.
IR(cm
-1)1629(C＝C)，968(C＝C)。
1HNMR(CDCl
3，400MHz)δ：7.91(d，1H，J＝16.2Hz，-CH＝CH-)，7.56(d，2H，J＝8.4Hz，Ar-H)，7.33(d，1H，J＝16.2Hz，-CH＝CH-)，6.97(s，1H，Py-H)，6.72(d，2H，J＝8.4Hz，Ar-H)，3.34(m，2H，J＝7.2Hz，S-CH
2-)，3.06(s，6H，N-CH
3)，2.64(s，3H，Py-CH
3)，1.50(t，3H，J＝7.2Hz，S-CH
2-CH
3)。
MS(70eV)m/z(％)：340.0(100)。
Listedly in the table 1 be the compound of synthetic general formula of the present invention (1).The implication of ellipsis in the table: Fc-ferrocenyl, TriPh-triphen amido, N-Car-N-hexyl carbazyl, 6-Br-Car-6-Br-N-hexyl carbazyl, N, N-DMPh-N, N-dimethylamino phenmethyl, N, N-DiBrPh-4-(N, N-biconjugate bromine phenylbenzene) aminophenyl, the m.p.-fusing point
Table 1
From following experiment as can be seen, compound of the present invention (1) has good photoluminescence property in chloroformic solution, and emission wavelength is from 449nm to 553nm, and wherein the luminous quantum efficiency of 2e is the highest.
Embodiment 7
The photoluminescence experiment:
Uv-visible absorption spectra (the λ of compound 1a-1f
Abs Max), fluorescence emission spectrum (λ
Spf Max) and quantum yield (Φ
f) (concentration in chloroformic solution is 1 * 10
-5Mol/L) data see Table 2.
Table 2
Presentation of results the present invention of embodiment 7 passes through molecular designing, synthetic is a series of to have 1 of different donors, 2,4-triazolo [1,5-a] pyrimidine-2-ethyl thioether monosubstituted derivative has good luminous property, study this compounds and both helped developing New n-N-type semiconductorN material, help exploring the structure sexual intercourse of miazines luminescent material again.And part of compounds of the present invention both can be made new and effective blue light, green light material, also can be used as the research of the relevant device of full-color display.
Claims (4)
1. a class 2,4-triazolo [1,5-a] pyrimidine-2-ethyl thioether monosubstituted derivative, (1) structure expressed that it is characterized in that having general formula,
In the formula: Ar is ferrocenyl, triphen amido, N-hexyl carbazyl, 6-bromo-N-hexyl carbazyl, 4-(N, N-biconjugate bromine phenylbenzene) aminophenyl or N, N-dimethylamino phenmethyl.
2. the preparation method of the represented chemical combination derivative of the described general formula of claim 1 (1) is characterized in that making represented compound of general formula (I) and ArCHO (II) reaction, (1) compound of expressing that obtains having general formula,
Ar is identical with the definition in the claim 1 in the formula (II).
3. the preparation method of the derivative that general formula as claimed in claim 2 (1) is represented, it is characterized in that: be solvent with the n-propyl alcohol, the piperidines that adds catalytic amount, make the represented compound of 1 mole general formula (I) and the represented compound of ArCHO of 2.1 times of moles, Ar is a ferrocenyl, the triphen amido, N-hexyl carbazyl, 6-bromo-N-hexyl carbazyl or 4-(N, N-biconjugate bromine phenylbenzene) aminophenyl, stirring and refluxing reaction 2 days, after having reacted, slough solvent, adopt 300-400 order silica gel chromatographic column to purify, the second colour band compound that obtains is the represented derivative of general formula (1).
4. the preparation method of the derivative that general formula as claimed in claim 2 (1) is represented, it is characterized in that: be solvent with the n-propyl alcohol, the piperidines that adds catalytic amount makes the represented compound of 1 mole general formula (I) and the represented compound of ArCHO of 1.1 times of moles, and Ar is N, N-dimethylamino phenmethyl, stirring and refluxing reaction 2 days after having reacted, is sloughed solvent, adopt 300-400 order silica gel chromatographic column to purify, the first colour band compound that obtains is the represented derivative of general formula (1).
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