CN103952148A - Blue ray material with triaryl anthracene or triaryl phenanthrene structure and preparation method of blue ray material - Google Patents
Blue ray material with triaryl anthracene or triaryl phenanthrene structure and preparation method of blue ray material Download PDFInfo
- Publication number
- CN103952148A CN103952148A CN201410205893.3A CN201410205893A CN103952148A CN 103952148 A CN103952148 A CN 103952148A CN 201410205893 A CN201410205893 A CN 201410205893A CN 103952148 A CN103952148 A CN 103952148A
- Authority
- CN
- China
- Prior art keywords
- triaryl
- anthracene
- luxuriant
- rich
- blue light
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Indole Compounds (AREA)
Abstract
The invention discloses a novel blue ray material with a 1,2,3-triaryl anthracene or 1,2,3-triaryl phenanthrene structure and a preparation method of the blue ray material. Derivatives of 1-(1-naphthyl)-2-(2-benzoxazolyl) acetylene and 1-(2-naphthyl)-2-(2-benzoxazolyl) acetylene are adopted as raw materials, a light ring addition reaction between hetero-aryl acetylenes is carried out in acetonitrile under irradiation of ultraviolet light. Maximum ultraviolet absorption wavelength of the novel triaryl anthracene or phenanthrene derivative is 280-300nm, shoulder peak of the novel triaryl anthracene or phenanthrene derivative extends to 380nm, and the novel triaryl anthracene or phenanthrene derivative can emit blue fluorescent lights with maximum emission wavelength of 380-400nm and shoulder peak extending to 500nm.
Description
Technical field:
The present invention relates to organic photoelectric functional material field, especially relate to organic blue light material with anthracene or luxuriant and rich with fragrance structure.
Background technology:
Organic electroluminescent technology is the novel technique of display that development in recent years is got up, and has replaced gradually traditional electronical display and lcd technology.Organic electroluminescent technology has the advantages such as brightness is high, functional molecular is simple in structure, energy consumption is low, visible angle is large, emission wavelength is adjustable, active illuminating, very extensive in the application prospect in various demonstrations field, is the study hotspot of organic functional material aspect.
In color organic electroluminescence display material, the exploitation of blue light material is an important gordian technique.Than green glow and ruddiness, blue light wavelength is the shortest, and energy is the highest, shifted and can be obtained green glow and ruddiness, then the blue light of launching with self coordinates by energy, can realize full color and show.Therefore the blue light emitting material of developing efficient stable has important theory significance and using value.
The machine blue light material of common are has polymer-type and organic molecule type.Polymer-type blue light material is easy to film forming, and with other materials compound property excellence, but preparation is complicated conventionally, and quality control difficulty is larger.And organic molecule type blue light material is easy to prepare, purity is high, steady quality, but be short of to some extent aspect film-forming properties and other materials compound property.Common small molecules type blue light material has aromatic hydrocarbons and arylamine class blue light material, in addition, goes back organic boron and silicone based blue light material etc.The function aryl of composition aromatic hydrocarbons blue light material has comprised the functional groups such as anthracene, fluorenes, pyrene, two alkenyl arenes.
In aromatic hydrocarbons blue light material, anthracene nucleus structure is the common used material that a class has good luminescent properties and chemical property, is subject to the attention of theoretical investigation always, and has practical application widely.But parent anthracene itself exists more serious defect, this is easy to crystallization as flush type molecule, and the film forming is loose, to the performance of device produced larger shadow to.By introduce substituting group on maternal anthracene nucleus, can improve the performance of anthracene nucleus, meet the performance requriements of electroluminescent device harshness.As introduced synthetic 9, the 10-diphenylanthrancene of phenyl or naphthyls and 9,10-bis-(betanaphthyl) anthracene etc. at 9 of anthracene nucleus and 10.
We have designed and synthesized novel 1,2, the 3-triaryl that has of a class and have replaced the new small molecule blue light material that anthracene or 1,2,3-triaryl replace luxuriant and rich with fragrance structure.Its substituting group is not to be positioned at anthracene or luxuriant and rich with fragrance 9 and 10, but at 1 of the same phenyl ring of a side, prosposition is set up the structure of introducing three aryl, and having synthesized the novel anthracene with unsymmetrical structure is that phenanthrene is blue light material.
Summary of the invention:
Main purpose of the present invention is to provide a kind of novel 1,2,3-triaryl replaces anthracene or 1,2,3-triaryl replaces the new Organic Electro Luminescent Materials of luxuriant and rich with fragrance structure, by changing different substituting groups, regulate and control the structure of whole molecule, thereby obtain organic molecule anthracene class and the luxuriant and rich with fragrance class blue light material of different luminescent properties.
It is characterized in that: general structure is suc as formula (I) with (II):
Wherein R group is-H ,-CH
3,-Cl ,-C (CH
3)
3,-CH
3o ,-F ,-Br ,-CN ,-(CH
2)
ncH
3(n=1～15).
The present invention explores and utilizes photochemically reactive technology, starts with from simple heteroaryl acetylene compound, by intermolecular photocycloaddition, has successfully realized the synthetic of this quasi-molecule.It is characterized in that: in acetonitrile solvent, add the heteroaryl ethane monomer taking 1-(2-naphthyl)-2-(2-benzoxazolyl) acetylene and 1-(1-naphthyl)-2-(2-benzoxazolyl) acetylene as representative, under the irradiation of medium-pressure or high pressure mercury lamp UV-light, there is intermolecular photocycloaddition, make 1,2,3-triaryl anthracene or 1, the derivative of 2,3-triaryl phenanthrene, reaction formula is as follows:
Provided by the present invention 1,2,3-triaryl anthracene and 1,2, the molecule of the luxuriant and rich with fragrance structure of 3-triaryl is unsymmetric structure, on one end phenyl ring of anthracene or phenanthrene, be connected with a naphthyl and two benzoxazolyls, parent anthracene or luxuriant and rich with fragrance conjugated system and moment of dipole are not only increased, the existence of simultaneously large steric hindrance naphthylene group has also destroyed the planarity of molecule, molecule is not easy mutually close, thereby has reduced intermolecular quenching effect, strengthened luminous intensity, also the solubleness that has increased this material, has strengthened the blending with other materials simultaneously.
The present invention designed 1,2, the ultraviolet maximum absorption wavelength of 3-triaryl anthracene and 1,2,3-triaryl phenanthrene derivative, between 282-292nm, has the characteristic ultraviolet absorption of typical anthracene and luxuriant and rich with fragrance compounds.Maximum emission wavelength is positioned at 400nm left and right, is typical blue-fluorescence, and the acromion of fluorescence extends to 500nm.
Brief description of the drawings:
Fig. 1 is compound a, b, c and the d ultra-violet absorption spectrum in methylene dichloride
Fig. 2 is compound a, b, c and the d fluorescence emission spectrum in methylene dichloride
Description of reference numerals
A has the compound of the structure (R=H) of structural formula (I)
B has the compound of the structure (R=H) of structural formula (II)
C has the structure (R=-C (CH of structural formula (I)
3)
3) compound
D has the structure (R=-C (CH of structural formula (II)
3)
3) compound
Specific implementation method:
The application's book has been listed part embodiment, but the embodiment that the scope of the compound of listing in the application's book is not limited only to list also comprises other compounds of enumerating in claims.
Embodiment mono-, 1-(2-naphthyl)-2, the structure of 3-bis-(2-benzoxazolyl) anthracene and synthetic
Take 400mg (1.48mmol) 1-(2-naphthyl)-2-(2-benzoxazolyl) acetylene and, in inner-immersed type photoreactor, add 80ml acetonitrile, ultrasonic it is dissolved completely, solution is colourless liquid, then sealing.Under nitrogen protection environment, with the illumination of 300W medium pressure mercury lamp, TLC monitors reaction at any time.After 2 hours, find that there is unique new dot generation, continue illumination, solution colour deepens gradually, and after 6 hours, raw material primitive reaction is complete, stopped reaction.Be spin-dried for solvent and obtain tan solid, with the separation of 100-200 order silica gel column chromatography, the de-agent in Shen is methylene dichloride: ethyl acetate=1: 1, obtain 260mg white powder, and yield is 65%, m.p.:212-214 DEG C.
1H?NMR(400MHz，CDCl
3，25℃，TMS)：δ(ppm)9.05(s，1H)，8.02(d，1H，J＝8.8Hz)，7.98(s，1H)，7.95(d，1H，J＝4Hz)，7.90(d，1H，J＝7.6HZ)，7.82-7.79(m，2H)，7.71(d，1H，J＝7.6Hz)，7.55(d，2H，J＝8.4Hz)，7.487.40(m，6H)，7.25-7.20(m，4H)，7.11-7.08(m，1H)，7.00-7.69(m，1H)；
13C?NMR(400MHz，CDCl
3，25℃，TMS)：δ(ppm)161.43，161.28，150.63，150.52，143.06，141.69，141.18，138.00，134.58，134.46，133.32，132.51，130.73，130.48，130.39，130.22，128.87，128.73，128.46，128.30，129.19，127.80，127.73，127.24，127.21，126.82，126.23，126.17，126.11，125.32，124，72，124.48，123.85，120.28，119.93，110.28；HRMS(ESI
+)[M+H]
+calculated?for?C
38H
23N
2O
2：539.1760，found：539.1758。
Embodiment bis-, 1-(1-naphthyl)-2, the structure that 3-bis-(2-benzoxazolyl) is luxuriant and rich with fragrance and synthetic
Get 1.00g1-(1-naphthyl)-2-(2-benzoxazolyl) acetylene and be dissolved in the acetonitrile of 150ml, obtain clarifying yellow solution.Adopt the medium pressure mercury lamp of 300W to irradiate after 6h, some plate finds, reaction is carried out completely, being spin-dried for acetonitrile solvent substantially, with PE: EA: DCM=90: carrying out column chromatography at 1: 1 obtains 0.721g pure substance, and productive rate is 72%, and m.p.:224-228 DEG C,
1h NMR (400MHz, CDCl
3, 25 DEG C, TMS): δ 9.93 (s, 1H, J=8.4Hz), 9.10-9.08 (d, 1H, J=8.4Hz), 7.2-7.90 (m, 1H), 7.55-7.40 (m, 6H), 7.34-7.30 (m, 1H), 7.26-7.12 (m, 6H) ppm;
13c NMR (400MHz, CDCl
3, 25 DEG C, TMS): 6161.1,160.5,149.9,149.7,141.2,140.9,140.3,133.7,132.3,132.2,132.1,131.7,130.6,129.1,128.0,127.7,127.7,127.3,127.2,126.9,125.6,125.1,124.5,124.2,124.1,124.0,124.0,123.8,123.7,1230.0,122.8,119.4,119.1,109.5ppm; HRMS (ESI): [M+H]
+=539.1746.
Embodiment tri-, 1-(2-naphthyl)-2, the structure of 3-bis-(the 5-tertiary butyl-2-benzoxazolyl) anthracene and synthetic
Using 1-(2-naphthyl)-2-(the 5-tertiary butyl-2-benzoxazolyl) acetylene is raw material, adopts the reaction conditions identical with embodiment mono-to be prepared.Yield 70%, m.p.:232-234 DEG C;
1h NMR (400MHz, CDCl
3, 25 DEG C, TMS): δ (ppm) 9.01 (s, 1H), 7.98 (d, 1H, J=8.8Hz), 7.93-7.86 (m, 3H), 7.81-7.77 (m, 2H), 7.68 (d, 1H, J=7.6Hz), 7.55-7.53 (m, 3H), 7.46-7.38 (m, 4H), 7.28 (s, 2H), 7.24 (m, 4H), 1.31 (d, 18H, J=2Hz);
13cNMR (400MHz, CDCl
3, 25 DEG C, TMS): δ (ppm) 161.59,161.40,148.77,148.64,147.99,147.09,142.89,141.59,141.34,138.16,134.52,134.43,133.39,132.53,130.67,130.42,130.34,130.21,128.83,128.74,128.46,128.27,127.94,127.70,127.27,127.11,127.05,126.13,126.04,125.07,123.06,122.37,116.67,116.43,109.38,109.35,34.84,34.82,31.72,31.67; HRMS (ESI
+) [M+H]
+calculated for C
46h
39n
2o
2: 651.3012, found:651.3016.
Embodiment tetra-, 1-(1-naphthyl)-2, the structure that 3-bis-(the 5-tertiary butyl-2-benzoxazolyl) is luxuriant and rich with fragrance and synthetic
Using 1-(1-naphthyl)-2-(the 5-tertiary butyl-2-benzoxazolyl) acetylene is raw material, adopts with the identical reaction conditions of embodiment bis-synthetic.Yield 74%, m.p., 262-268 DEG C;
1h NMR (400MHz, CDCl
3, 25 DEG C, TMS): δ 9.88 (s, 1H), 9.06-9.03 (d, 1H, J=8Hz), 7.90-7.79 (m, 4H), 7.73-7.69 (m, 1H), 7.65-7.61 (m, 2H), 7.55-7.41 (m, 6H), 7.34-7.25 (m, 2H), 7.16-7.12 (m, 2H), 6.95-6.93 (m, 1H) ppm;
13c NMR (400MHz, CDCl
3, 25 DEG C, TMS): δ 148.7,148.5,147.9,141.1,133.4,133.1,132.3,130.1,128.5,127.6,126.9,125.9,125.2,124.3,118.0,116.8,109.8,91.7,82.3,77.3,77.0,76.7ppm; HRMS (ESI): [M+H]
+=651.3005.
Claims (4)
1. there is the blue light material of the luxuriant and rich with fragrance structure of triaryl anthracene or triaryl, it is characterized in that: 1,2,3-triaryl anthracene and 1,2, the molecule of the luxuriant and rich with fragrance structure of 3-triaryl is unsymmetric structure, is connected with the benzoxazolyl of a naphthyl and two replacements on one end phenyl ring of anthracene or phenanthrene, and this type of structural compounds can be used as a kind of blue light emitting material.
2. there is the preparation method of the blue light material of the luxuriant and rich with fragrance structure of triaryl anthracene or triaryl, it is characterized in that: in acetonitrile solvent, taking 1-(2-naphthyl)-2-(5-R-2-benzoxazolyl) acetylene and 1-(1-naphthyl)-2-(5-R-2-benzoxazolyl) acetylene as raw material, under the irradiation of UV-light, there is intermolecular photocycloaddition.
3. the blue light material with triaryl anthracene or the luxuriant and rich with fragrance structure of triaryl according to claim 1, is characterized in that in the luxuriant and rich with fragrance structure of 1,2,3-triaryl anthracene or 1,2,3-triaryl R=-H ,-CH
3,-Cl ,-C (CH
3)
3,-CH
3o ,-F ,-Br ,-CN ,-(CH
2)
ncH
3(n=1～15).
4. the preparation method of the blue light material with triaryl anthracene or the luxuriant and rich with fragrance structure of triaryl according to claim 2, is characterized in that, photochmeical reaction is carried out in acetonitrile solution, and the ultraviolet lighting equipment using is medium-pressure or high pressure mercury lamp.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410205893.3A CN103952148A (en) | 2014-05-16 | 2014-05-16 | Blue ray material with triaryl anthracene or triaryl phenanthrene structure and preparation method of blue ray material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410205893.3A CN103952148A (en) | 2014-05-16 | 2014-05-16 | Blue ray material with triaryl anthracene or triaryl phenanthrene structure and preparation method of blue ray material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103952148A true CN103952148A (en) | 2014-07-30 |
Family
ID=51329508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410205893.3A Pending CN103952148A (en) | 2014-05-16 | 2014-05-16 | Blue ray material with triaryl anthracene or triaryl phenanthrene structure and preparation method of blue ray material |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103952148A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104845612A (en) * | 2015-04-29 | 2015-08-19 | 南华大学 | Polystyrene mercury ion fluorescence recognition materials and preparation method thereof |
-
2014
- 2014-05-16 CN CN201410205893.3A patent/CN103952148A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104845612A (en) * | 2015-04-29 | 2015-08-19 | 南华大学 | Polystyrene mercury ion fluorescence recognition materials and preparation method thereof |
| CN104845612B (en) * | 2015-04-29 | 2017-05-03 | 南华大学 | Polystyrene mercury ion fluorescence recognition materials and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107614659B (en) | Pyrromethene boron complex, color conversion composition, color conversion film, and light source unit, display, and lighting device comprising same | |
| CN104498025B (en) | Many phenyl benzene constructs cyano-containing light emitting molecule and its production and use | |
| CN104447582B (en) | Tetraphernl pyrazine small molecule derivative, tetraphernl pyrazine polymer and gathering induced luminescence material | |
| CN103242298A (en) | 1,2,4-triazole derivative, preparation method and application thereof and organic electroluminescent device | |
| CN104629721B (en) | Organic luminescent material with excellent performance and preparation method thereof | |
| CN109734608A (en) | A kind of organic compound and its organic electroluminescence device using the compound | |
| Song et al. | Novel fluorescent blue-emitting materials based on anthracene-fluorene hybrids with triphenylsilane group for organic light-emitting diodes | |
| CN108794382B (en) | Multifunctional aggregation-induced emission enhancement compound and preparation method and application thereof | |
| CN113402561A (en) | High-color-purity platinum (II) complex luminescent material based on spirofluorene structure and application thereof | |
| CN107312017A (en) | A kind of electroluminescent organic material and its organic luminescent device of Han phenoxazines/Sai oxazine analog derivatives | |
| CN104311588B (en) | Aggregation-induced emission molecule based on silicon fluorene and its preparation method and application | |
| CN102617466A (en) | Top-bottom asymmetrical tert-butyl spirobifluorene compound | |
| Wu et al. | Dual emission from donor-modified MR-TADF emitter: Evidence for coexistence of TICT and MR excited states | |
| Dong et al. | Binaphthol-based chiral host molecules for efficient solution-processed circularly polarized OLEDs | |
| CN108129431B (en) | Fluorenonaphthofuran derivative and application thereof | |
| CN103539737A (en) | Aza-phenanthro-fluorene derivative and preparation method thereof as well as electrically-induced fluorescence luminescent device | |
| CN103952148A (en) | Blue ray material with triaryl anthracene or triaryl phenanthrene structure and preparation method of blue ray material | |
| CN105085551B (en) | Aromatic heterocycle derivative and the organic light emitting diode device using the compound | |
| CN110759935B (en) | Blue thermal activity delayed fluorescent material based on fluorine boron complex and application thereof | |
| CN103102299B (en) | A kind of benzanthrene derivative, its preparation method and the electroluminescent organic material be made up of it | |
| CN112174980B (en) | Organic compound with eight-membered ring as core structure and application thereof | |
| CN101575506B (en) | Organic-inorganic hybrid blue light luminescent material based on polyhedral oligomeric silsesquioxane, preparation method and application thereof | |
| CN110724105B (en) | Triphenylene nitrogen-containing seven-membered ring compound and preparation method and application thereof | |
| CN110467914B (en) | Thermal-activation delay fluorescent material, preparation method thereof and OLED device | |
| CN113201022A (en) | Small conjugated phosphorescent metal iridium (III) complex with isomer and preparation method and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20140730 |