CN104073238A - Organic electroluminescent material and preparation method thereof, and organic electroluminescent device - Google Patents
Organic electroluminescent material and preparation method thereof, and organic electroluminescent device Download PDFInfo
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- CN104073238A CN104073238A CN201310098669.4A CN201310098669A CN104073238A CN 104073238 A CN104073238 A CN 104073238A CN 201310098669 A CN201310098669 A CN 201310098669A CN 104073238 A CN104073238 A CN 104073238A
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- BOPPHKMZOYPASP-UHFFFAOYSA-N Brc(cc1)ccc1-c1cc(-c2ccccn2)nc(-c2ccccn2)c1 Chemical compound Brc(cc1)ccc1-c1cc(-c2ccccn2)nc(-c2ccccn2)c1 BOPPHKMZOYPASP-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention relates to an organic electroluminescent material and a preparation method thereof, and an organic electroluminescent device prepared by using the organic electroluminescent material. The organic electroluminescent material has a general formula (P) as shown in the specification, and in the general formula (P), R is one selected from C1 to C12 alkyl groups. The organic electroluminescent material provided by the invention has good carrier transport performance and thermal stability and excellent dissolving performance and film forming performance.
Description
Technical field
The present invention relates to field of photovoltaic materials, relate in particular to a kind of electroluminescent organic material.The invention still further relates to the preparation method of described electroluminescent organic material and adopt described electroluminescent organic material and the organic electroluminescence device that makes.
Background technology
Along with the development of information age, there is the organic EL display (OLEDs) of efficient, energy-conservation, lightweight and big area white-light illuminating and be more and more subject to people's concern.OLED technology is paid close attention to by global scientist, and relevant enterprise and laboratory are all in the research and development of carrying out this technology.As a kind of novel LED technology, there is active illuminating, light, thin, good contrast, energy consumption organic electroluminescence device low, that can be made into the features such as flexible device material has been proposed to higher requirement.
1987, the Tang of Eastman Kodak company of the U.S. and VanSlyke reported the breakthrough in organic electroluminescent research.And to realize the application purposes such as panchromatic demonstration and illumination, luminescent device must have certain efficiency and life-span.The material at present with high mobility, high stability lacks, and has affected OLED device efficiency and the lifting in life-span.
Therefore, the present invention designs, has synthesized the organic semiconductor material containing thionaphthene sulfone and fluorenes, and this material has good electronic injection, transmission performance and thermal stability.
Summary of the invention
The defect or the deficiency that exist for above-mentioned background technology, the first object of the present invention is to provide a kind of electroluminescent organic material, and described electroluminescent organic material has good electronic injection, transmission performance and thermal stability.
The second object of the present invention is to provide a kind of preparation method of electroluminescent organic material.
The 3rd object of the present invention is to provide a kind of organic electroluminescence device being made by electroluminescent organic material.
In order to realize first object of the present invention, the technical solution adopted in the present invention is:
Electroluminescent organic material of the present invention has following general formula (P),
Wherein, R represents C
1～C
12one in alkyl.Preferably, R is expressed as methyl, hexyl or dodecyl.
In the technical program, described electroluminescent organic material is containing two indenes pyrazine groups, and the structural formula of this two indenes pyrazine group is as follows:
This two indenes pyrazine group has rigid planar structure makes described electroluminescent organic material have high chemical heat stability and thermostability.This two indenes pyrazine group is the effective stacking carrier mobility that described electroluminescent organic material has been had of π – π in film.
In the technical program, described electroluminescent organic material is containing 2,2':6', 2''-terpyridyl group, this 2,2':6', the structural formula of 2''-terpyridyl group is as follows:
These are 2 years old, 2':6', 2''-terpyridyl group is electron deficiency group, be conducive to the electric transmission of described electroluminescent organic material, two pyridine is substituted in 2 of same pyridine simultaneously, 6 upper unit structures that form, also give material certain steric hindrance, can improve the thermostability of described electroluminescent organic material.
In order to realize the second object of the present invention, the technical solution adopted in the present invention is:
The preparation method of above-mentioned electroluminescent organic material, comprises the following steps:
(a) provide following compd A and B;
Compd A:
Compd B:
Wherein, R represents C
1～C
12one in alkyl.
(b) by described compd A, described compd B and catalyst mix, in atmosphere of inert gases, add basic solution and organic solvent, at 75～120 DEG C, carry out Suzuki coupling reaction (also claiming Suzuki coupling reaction) 24～48 hours, make reaction solution, purification by liquid extraction, obtains described electroluminescent organic material; Wherein, described compd A and compd B mol ratio are 1:2～3.
In above-mentioned steps (b), described catalyzer is organic palladium, and the mol ratio of described organic palladium and described compd A is 0.001～0.1:1.
In above-mentioned steps (b), described organic palladium is tetrakis triphenylphosphine palladium, two (triphenylphosphine) palladium chloride or three (dibenzalacetone) two palladiums.
In above-mentioned steps (b), described rare gas element is one or both in nitrogen, argon gas.
In above-mentioned steps (b), described basic solution is Cs
2cO
3, K
2cO
3or Na
2cO
3solution, the concentration of described basic solution is 2mol/L, the solute in described basic solution and the mol ratio of described compd A are 20～25:1.
In above-mentioned steps (b), described organic solvent is tetrahydrofuran (THF), glycol dimethyl ether or toluene.
In above-mentioned steps (b), described purification by liquid extraction step is as follows: described reaction solution is poured in saturated aqueous ammonium chloride, with dichloromethane extraction, organic phase is washed with sodium chloride aqueous solution, dry, revolve steaming and obtain crude product except after desolventizing, subsequently crude product is carried out to silica gel column chromatography separating-purifying.
Reaction formula related in the preparation method of above-mentioned electroluminescent organic material is as follows:
In formula, R represents C
1～C
12one in alkyl.
In order to realize the 3rd object of the present invention, the technical solution adopted in the present invention is:
A kind of organic electroluminescence device, it comprises the substrate, anode layer, hole transmission layer, luminescent layer, electron transfer layer, buffer layer and the cathode layer that stack gradually.The material of described electron transfer layer is above-mentioned electroluminescent organic material.
Compared with prior art, electroluminescent organic material of the present invention has good carrier transmission performance and thermal stability, and there is excellent solubility property and film forming properties, can be dissolved in common organic solvent as conventional in tetrahydrofuran (THF), methylene dichloride, trichloromethane, toluene etc.Adopt the organic electroluminescence device that described electroluminescent organic material makes to use desirable.
Brief description of the drawings
Fig. 1 is the structure iron of the organic electroluminescence device prepared by embodiment 1.
Fig. 2 is the electroluminescent spectrum figure of the organic electroluminescence device prepared by the present embodiment 4.
Embodiment
The following stated is the preferred embodiment of the present invention.It should be pointed out that for those skilled in the art, under the premise without departing from the principles of the invention, can also make some improvement and adjustment, these improvement and adjustment are also considered as in protection scope of the present invention.
Embodiment 1
A kind of electroluminescent organic material P in the open organic semiconductor material of the present embodiment
1: 2,8-bis-(((2,6-bis-(pyridine-2-yl) pyridine)-4-yl) benzene-4-yl)-6,6,12,12-tetramethyl--6,12-dihydro two indenes [1,2-b; 1', 2'-e] pyrazine, it is abbreviated as DTPyPMIPy, described electroluminescent organic material P
1structural formula as follows:
For preparing described compound P
1, related method comprises the steps:
(1) get respectively the compd A that following structural formula represents
1(2,8-bis-(4'-(4-bromophenyl)-2,2':6', 2''-terpyridyl)-6,6,12,12-tetramethyl--6,12-dihydro two indenes [1,2-b; 1', 2'-e] pyrazine) and compd B (4'-(4-bromophenyl)-2,2':6', 2''-terpyridyl);
A
1：
B：
(2) by the compd A of 4.0mmol
1(2,8-bis-(4,4,5,5-tetramethyl--1,3,2-dioxa borine-2-yl)-6,6,12,12-tetramethyl--6,12-dihydro two indenes [1,2-b; 1'; 2'-e] pyrazine), the compd B (4'-(4-bromophenyl)-2 of 8.0mmol; 2':6'; 2''-terpyridyl) and the catalyzer (tetrakis triphenylphosphine palladium) of 0.4mmol join in reaction flask; vacuumize rear logical nitrogen circulation 3 times; make reaction system in anaerobic state, under nitrogen protection, add the Na of the 2mol/L of 55ml tetrahydrofuran solution, 40ml
2cO
3solution, carries out coupling reaction by mixed solution heating, and 75～80 DEG C of back flow reaction 24h make containing 2; 8-bis-(((2,6-bis-(pyridine-2-yl) pyridine)-4-yl) benzene-4-yl)-6,6,12; 12-tetramethyl--6,12-dihydro two indenes [1,2-b; 1', 2'-e] reaction solution of pyrazine, reaction solution is poured in the aqueous solution of saturated ammonium chloride; dichloromethane extraction three times, organic phase is washed with sodium chloride aqueous solution, dry; revolve steaming and obtain crude product except after desolventizing, through silica gel column chromatography separating-purifying, finally obtain the solid product 2 after purifying; 8-bis-(((2,6-bis-(pyridine-2-yl) pyridine)-4-yl) benzene-4-yl)-6,6; 12; 12-tetramethyl--6,12-dihydro two indenes [1,2-b; 1', 2'-e] pyrazine, i.e. described electroluminescent organic material P
1.
In the present embodiment, 2,8-bis-(((2,6-bis-(pyridine-2-yl) pyridine)-4-yl) benzene-4-yl)-6,6,12,12-tetramethyl--6,12-dihydro two indenes [1,2-b; 1', 2'-e] productive rate of pyrazine is 47%.
To described 2,8-bis-(((2,6-bis-(pyridine-2-yl) pyridine)-4-yl) benzene-4-yl)-6,6,12,12-tetramethyl--6,12-dihydro two indenes [1,2-b; 1', 2'-e] pyrazine carries out mass spectroscopy, and the test result obtaining is: MS:m/z=927 (M+).
To described 2,8-bis-(((2,6-bis-(pyridine-2-yl) pyridine)-4-yl) benzene-4-yl)-6,6,12,12-tetramethyl--6,12-dihydro two indenes [1,2-b; 1', 2'-e] pyrazine carries out ultimate analysis, and the test result obtaining is: molecular formula is C
64h
44n
8, wherein the massfraction of C is 82.84%; The massfraction of H is 5.05%; The massfraction of N is 12.12%.
Embodiment 2
A kind of electroluminescent organic material P in the open organic semiconductor material of the present embodiment
2: 2,8-bis-(((2,6-bis-(pyridine-2-yl) pyridine)-4-yl) benzene-4-yl)-6,6,12,12-tetra-hexyl-6,12-dihydro two indenes [1,2-b; 1', 2'-e] pyrazine, it is abbreviated as DTPyPHIPy, described electroluminescent organic material P
2structural formula as follows:
P2:
For preparing described compound P
2, related method comprises the steps:
(1) get respectively the compd A that following structural formula represents
2(2,8-bis-(4,4,5,5-tetramethyl--1,3,2-dioxa borine-2-yl)-6,6,12,12-tetra-hexyl-6,12-dihydro two indenes [1,2-b; 1', 2'-e] pyrazine) and compd B (4'-(4-bromophenyl)-2,2':6', 2''-terpyridyl),
A
2：
B：
(2) by the compd A of 4.0mmol
2(2,8-bis-(4,4,5,5-tetramethyl--1,3,2-dioxa borine-2-yl)-6,6,12,12-tetra-hexyl-6,12-dihydro two indenes [1,2-b; 1'; 2'-e] pyrazine), the compd B (4'-(4-bromophenyl)-2 of 9.0mmol; 2':6'; 2''-terpyridyl) and the catalyzer (three (dibenzalacetone) two palladiums) of 0.12mmol join in reaction flask; vacuumize rear logical argon gas circulation 3 times; make reaction system in anaerobic state, under argon shield, add the K of the 2mol/L of 70mL glycol dimethyl ether, 45ml
2cO
3solution, carries out Suzuki coupling reaction by mixed solution heating, and 95 DEG C of back flow reaction 40h make containing 2; 8-bis-(((2,6-bis-(pyridine-2-yl) pyridine)-4-yl) benzene-4-yl)-6,6,12; 12-tetra-hexyl-6,12-dihydro two indenes [1,2-b; 1', 2'-e] reaction solution of pyrazine, reaction solution is poured in the aqueous solution of saturated ammonium chloride; dichloromethane extraction three times, organic phase is washed with sodium chloride aqueous solution, dry; revolve steaming and obtain crude product except after desolventizing, through silica gel column chromatography separating-purifying, finally obtain the solid product 2 after purifying; 8-bis-(((2,6-bis-(pyridine-2-yl) pyridine)-4-yl) benzene-4-yl)-6,6; 12; 12-tetra-hexyl-6,12-dihydro two indenes [1,2-b; 1', 2'-e] pyrazine, i.e. described electroluminescent organic material P
2.
In the present embodiment, 2,8-bis-(((2,6-bis-(pyridine-2-yl) pyridine)-4-yl) benzene-4-yl)-6,6,12,12-tetra-hexyl-6,12-dihydro two indenes [1,2-b; 1', 2'-e] productive rate of pyrazine is 64%.
To described 2,8-bis-(((2,6-bis-(pyridine-2-yl) pyridine)-4-yl) benzene-4-yl)-6,6,12,12-tetra-hexyl-6,12-dihydro two indenes [1,2-b; 1', 2'-e] pyrazine carries out mass spectroscopy, and the test result obtaining is: MS:m/z=1207 (M+).
To described 2,8-bis-(((2,6-bis-(pyridine-2-yl) pyridine)-4-yl) benzene-4-yl)-6,6,12,12-tetra-hexyl-6,12-dihydro two indenes [1,2-b; 1', 2'-e] pyrazine carries out ultimate analysis, and the test result obtaining is: molecular formula is C
84h
86n
8, the massfraction of C is 83.47%; The massfraction of H is 7.21%; The massfraction of N is 9.32%.
Embodiment 3
A kind of electroluminescent organic material P in the open organic semiconductor material of the present embodiment
3: 2,8-bis-(((2,6-bis-(pyridine-2-yl) pyridine)-4-yl) benzene-4-yl)-6,6,12,12-tetra-(dodecane) base-6,12-dihydro two indenes [1,2-b; 1', 2'-e] pyrazine, it is abbreviated as DTPyPDIPy, described electroluminescent organic material P
3structural formula as follows:
For preparing described compound P
3, related method comprises the steps:
(1) get respectively the compd A that following structural formula represents
3(2,8-bis-(4,4,5,5-tetramethyl--1,3,2-dioxa borine-2-yl)-6,6,12,12-tetra-(dodecane) base-6,12-dihydro two indenes [1,2-b; 1', 2'-e] pyrazine) and compd B (4'-(4-bromophenyl)-2,2':6', 2''-terpyridyl),
A
3：
B：
(2) by the compd A of 4.0mmol
3(2,8-bis-(4,4,5,5-tetramethyl--1,3,2-dioxa borine-2-yl)-6,6,12,12-tetra-(dodecane) base-6,12-dihydro two indenes [1,2-b; 1'; 2'-e] pyrazine), the compd B (4'-(4-bromophenyl)-2 of 12.0mmol; 2':6'; 2''-terpyridyl) and the catalyzer (two (triphenylphosphine) palladium chloride) of 0.004mmol join in reaction flask; the mixed gas that vacuumizes rear logical nitrogen and argon gas circulates 3 times; make reaction system in anaerobic state, under nitrogen and argon gas mixed gas protected, add the 2mol/LCs of 60mL toluene solution, 50ml
2cO
3solution; mixed solution heating is carried out to Suzuki coupling reaction; 120 DEG C of back flow reaction 48h, make containing 2,8-bis-(((2; 6-bis-(pyridine-2-yl) pyridine)-4-yl) benzene-4-yl)-6; 6,12,12-tetra-(dodecane) base-6; 12-dihydro two indenes [1,2-b; 1'; 2'-e] reaction solution of pyrazine; reaction solution is poured in the aqueous solution of saturated ammonium chloride; dichloromethane extraction three times; organic phase is washed with sodium chloride aqueous solution; dry, revolve steaming and obtain crude product except after desolventizing, through silica gel column chromatography separating-purifying; finally obtain the solid product 2 after purifying; 8-bis-(((2,6-bis-(pyridine-2-yl) pyridine)-4-yl) benzene-4-yl)-6,6; 12; 12-tetra-(dodecane) base-6,12-dihydro two indenes [1,2-b; 1', 2'-e] pyrazine, i.e. described electroluminescent organic material P
3.
In the present embodiment 2,8-bis-(((2,6-bis-(pyridine-2-yl) pyridine)-4-yl) benzene-4-yl)-6,6,12,12-tetra-(dodecane) base-6,12-dihydro two indenes [1,2-b; 1', 2'-e] productive rate of pyrazine is 84%.
To described 2,8-bis-(((2,6-bis-(pyridine-2-yl) pyridine)-4-yl) benzene-4-yl)-6,6,12,12-tetra-(dodecane) base-6,12-dihydro two indenes [1,2-b; 1', 2'-e] pyrazine carries out mass spectroscopy, and the test result obtaining is: MS:m/z1544 (M
+).
To described 2,8-bis-(((2,6-bis-(pyridine-2-yl) pyridine)-4-yl) benzene-4-yl)-6,6,12,12-tetra-(dodecane) base-6,12-dihydro two indenes [1,2-b; 1', 2'-e] pyrazine carries out ultimate analysis, and the test result obtaining is: molecular formula is C
108h
134n
8, wherein the massfraction of C is 84.18%; The massfraction of H is 8.74%; The massfraction of N is 7.29%.
The heat stability testing of electroluminescent organic material
Utilize thermogravimetric analyzer (TGA) to detect to above-described embodiment 1 to 3 electroluminescent organic material below.The analysis condition of this thermogravimetric analysis is that nitrogen atmosphere, sweep velocity are 10 DEG C/min.
The heat decomposition temperature data that table 1 is embodiment 1 to 3 electroluminescent organic material that recorded by thermogravimetric analyzer.As shown in Table 1, the heat decomposition temperature of embodiment 1 to 3 electroluminescent organic material more than (5% thermal weight loss), illustrates that this compounds has quite high thermostability up to 410 DEG C.
Table 1
| Compound | Embodiment 1 | Embodiment 2 | Embodiment 3 |
| Heat decomposition temperature (5% thermal weight loss)/DEG C | 425 | 420 | 418 |
Table 2 is electronic mobility data of embodiment 1 to 3 electroluminescent organic material that records by time of flight method method.Test result shows, is 8.0 × 10 at electric field
5vcm
-1time, the electronic mobility of embodiment 1 to 3 electroluminescent organic material is 1.0 × 10
-6cm
2(Vs)
-1above, illustrate that electroluminescent organic material of the present invention has good electronic transmission performance.
Table 2
| Compound | Embodiment 1 | Embodiment 2 | Embodiment 3 |
| Electronic mobility/cm 2(Vs) -1 | 2.7×10 -5 | 4.2×10 -6 | 1.2×10 -6 |
Embodiment 4
Fig. 1 illustrates the organic electroluminescence device of the present embodiment, the electroluminescent organic material P that this organic electroluminescence device adopts embodiment 1 to make
1(DTPyPMIPy) make.
This organic electroluminescence device comprises the substrate, anode layer, hole transmission layer, luminescent layer, electron transfer layer, buffer layer and the cathode layer that stack gradually.Wherein:
The material of substrate adopts glass (glass);
The material of anode layer is preferably the ITO(tin indium oxide that square resistance is 10-20 Ω/mouth), thickness is 150nm;
The material of hole transmission layer is N, N '-bis-(Alpha-Naphthyl)-N, N '-phenylbenzene-4,4 '-diamines (NPB), thickness 40nm;
The material of main part of luminescent layer is N, N '-bis-(Alpha-Naphthyl)-N, N '-phenylbenzene-4,4 '-diamines (NPB), the guest materials of luminescent layer is that two (2-(2'-benzothienyl) pyridine-N, C3') (methyl ethyl diketone) closes iridium (Ir (btp)
2(acac)); Ir (btp)
2(acac) be doped in NPB by 4% mass percent, the thickness of luminescent layer is 30nm.
The material of electron transfer layer is the electroluminescent organic material P that embodiment 1 makes
1(DTPyPMIPy), be 2,8-bis-(((2,6-bis-(pyridine-2-yl) pyridine)-4-yl) benzene-4-yl)-6,6,12,12-tetramethyl--6,12-dihydro two indenes [1,2-b; 1', 2'-e] pyrazine, the thickness of electron transfer layer is 45nm;
The material of buffer layer is lithium fluoride, i.e. LiF, and thickness is 1nm;
The material of cathode layer is aluminium lamination, thickness 120nm.
Therefore, as shown in Figure 1, this organic electroluminescence device is straticulate structure, and its structure is: glass/ITO/NPB/NPB:Ir (btp)
2(acac)/P1/LiF/Al; Wherein, brace "/" represents laminate structure, NPB:Ir (btp)
2(acac) colon ": " in represents doping.
This organic electroluminescence device is tested through at room temperature, in atmospheric environment, and this organic electroluminescence device part of ruddiness has been obtained the maximum light efficiency of 9.6lm/W.
Fig. 2 is the electroluminescent spectrum figure of the present embodiment 4 organic electroluminescence devices, and its maximum emission wavelength is at 612nm place, with red dopant Ir (btp)
2(acac) intrinsic emission peak is consistent, illustrates that exciton energy fully transfers to the material of main part of luminescent layer luminous from the material of main part of luminescent layer.
Foregoing; it is only preferred embodiment of the present invention; not for limiting embodiment of the present invention; those of ordinary skill in the art are according to main design of the present invention and spirit; can carry out very easily corresponding flexible or amendment, therefore protection scope of the present invention should be as the criterion with the desired protection domain of claims.
Claims (10)
1. an electroluminescent organic material, (P) is as follows for its general formula:
(P)：
Wherein, R is C
1～C
12one in alkyl.
2. electroluminescent organic material according to claim 1, is characterized in that, wherein R is methyl, hexyl or dodecyl.
3. a preparation method for electroluminescent organic material claimed in claim 1, is characterized in that, this preparation method comprises the following steps:
(a) provide following compd A and compd B;
Compd A:
Compd B:
Wherein, R is C
1～C
12one in alkyl;
(b), by described compd A, described compd B and catalyst mix, in atmosphere of inert gases, add basic solution and organic solvent, at 75～120 DEG C, carry out Suzuki coupling reaction 24～48 hours, make reaction solution, purification by liquid extraction, obtains described electroluminescent organic material; Wherein, described compd A and compd B mol ratio are 1:2～3.
4. preparation method according to claim 3, is characterized in that, described catalyzer is organic palladium, and the mol ratio of described organic palladium and described compd A is 0.001～0.1:1.
5. preparation method according to claim 4, is characterized in that, described organic palladium is tetrakis triphenylphosphine palladium, two (triphenylphosphine) palladium chloride or three (dibenzalacetone) two palladiums.
6. preparation method according to claim 3, is characterized in that, described rare gas element is one or both in nitrogen, argon gas.
7. preparation method according to claim 3, is characterized in that, described basic solution is Cs
2cO
3, K
2cO
3or Na
2cO
3solution, the concentration of described basic solution is 2mol/L, the solute in described basic solution and the mol ratio of described compd A are 20～25:1.
8. preparation method according to claim 3, is characterized in that, described organic solvent is tetrahydrofuran (THF), glycol dimethyl ether or toluene.
9. preparation method according to claim 3, it is characterized in that, described purification by liquid extraction step is as follows: the reaction solution described in step (b) is poured in saturated aqueous ammonium chloride, with dichloromethane extraction, organic phase is washed with sodium chloride aqueous solution, dry, revolve steaming and obtain crude product except after desolventizing, subsequently crude product is carried out to silica gel column chromatography separating-purifying.
10. an organic electroluminescence device, it comprises the substrate, anode layer, hole transmission layer, luminescent layer, electron transfer layer, buffer layer and the cathode layer that stack gradually, it is characterized in that, the material of described electron transfer layer is electroluminescent organic material claimed in claim 1.
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| CN113321659A (en) * | 2021-05-27 | 2021-08-31 | 武汉尚赛光电科技有限公司 | Organic electroluminescent material and device thereof |
| CN116041738A (en) * | 2023-01-10 | 2023-05-02 | 东北林业大学 | Preparation method of multi-fluorescent-color cellulose-based hydrogel based on excitation wavelength dependence and application of multi-fluorescent-color cellulose-based hydrogel in multi-mode four-dimensional anti-counterfeiting |
| CN116041738B (en) * | 2023-01-10 | 2023-08-22 | 东北林业大学 | Preparation method of multi-fluorescent-color cellulose-based hydrogel based on excitation wavelength dependence and application of multi-fluorescent-color cellulose-based hydrogel in multi-mode four-dimensional anti-counterfeiting |
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Application publication date: 20141001 |