CN104370752A - Synthesis of 1,3,5-tri(aryl amido) phenyl aromatic compound and application of 1,3,5-tri(aryl amido) phenyl aromatic compound on OLED (Organic Light-Emitting Diode) device - Google Patents
Synthesis of 1,3,5-tri(aryl amido) phenyl aromatic compound and application of 1,3,5-tri(aryl amido) phenyl aromatic compound on OLED (Organic Light-Emitting Diode) device Download PDFInfo
- Publication number
- CN104370752A CN104370752A CN201410572979.XA CN201410572979A CN104370752A CN 104370752 A CN104370752 A CN 104370752A CN 201410572979 A CN201410572979 A CN 201410572979A CN 104370752 A CN104370752 A CN 104370752A
- Authority
- CN
- China
- Prior art keywords
- oled
- compounds
- general formula
- aromatic
- tri
- 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.)
- Granted
Links
Abstract
The invention provides a synthetic method of an aromatic amine compound with 1,3,5-tri(aryl amido) phenyl group as a main body and application of the aromatic amine compound in an OLED (Organic Light-Emitting Diode). The material has the advantages of good optical-electrical characteristic, easiness for amorphous film formation, high vitrification transfer temperature and decomposition temperature and proper HOMO and LUMO energy level, thereby being used as a hole injection material, a hole transfer material or a hole injection and transfer material in an organic electroluminescent device.
Description
Technical field
The present invention relates to technical field of semiconductors, especially relating to a kind of main body is 1,3, the synthetic method of 5-tri-(arylamine group) phenyl grouping of the world economy compound, and as independently hole-injecting material, independent hole mobile material or the application of hole injection transport material on Organic Light Emitting Diode.
Background technology
Organic electroluminescent (OLED:Organic Light Emission Diodes) device technology both can be used for manufacturing novel display product, also may be used for making novel illumination product, be expected to alternative existing liquid-crystal display and fluorescent lighting, application prospect is very extensive.
Current, OLED technique of display is at smart mobile phone, and the fields such as panel computer obtain application, further also will to large size Application Areas expansions such as TVs.But require to compare with the product application of reality, the luminous efficiency of OLED, the performances such as work-ing life also need further lifting.
OLED luminescent device, just as the structure of sandwich, comprises electrode materials rete, and is clipped in the organic functional material between Different electrodes rete, and various difference in functionality material is mutually superimposed according to purposes and jointly forms OLED luminescent device.As current driving apparatus, when applying voltage to the two end electrodes of OLED luminescent device, and by positive and negative charge in electric field action organic layer functional materials rete, positive and negative charge is compound in luminescent layer further, namely produces OLED electroluminescent.
High performance research is carried for OLED luminescent device comprise: the driving voltage reducing device, improve the luminous efficiency of device, improve the work-ing life etc. of device.In order to realize the continuous lifting of the performance of OLED, not only needing the innovation from OLED structure and manufacture craft, more needing oled light sulfate ferroelectric functional material constantly study and innovate, formulating out the functional materials of more high-performance OLED.
The oled light sulfate ferroelectric functional material being applied to OLED can be divided into two large classes purposes, i.e. charge injection transport material and luminescent material, further, also charge injection transport material can be divided into electron injection transport material and hole to inject transport material, luminescent material can also be divided into main body luminescent material and dopant material.In order to make high performance OLED luminescent device, require that various organic functional material possesses good photoelectric characteristic, for example, as charge transfer material, require that there is good carrier mobility, high-vitrification invert points etc., the material of main part as luminescent layer requires that material has good bipolarity, suitable HOMO/LUMO energy rank etc.
The oled light sulfate ferroelectric functional material rete forming OLED at least comprises two-layer above structure, the OLED structure that industry is applied, then comprise the multiple retes such as hole injection layer, hole transmission layer, luminescent layer, electron injecting layer, that is the photoelectric functional material being applied to OLED at least comprises hole-injecting material, hole mobile material, luminescent material, electron injection material etc., material type and collocation form have rich and multifarious feature.In addition, for the OLED collocation of different structure, the photoelectric functional material used has stronger selectivity, the performance of identical material in different structure device, also may be completely totally different.
Therefore, for the industry application requiring of current OLED, and the difference in functionality rete of OLED, the photoelectric characteristic demand of device, must select to be more suitable for, there is high performance OLED functional materials or combination of materials, the overall characteristic of the high-level efficiency of device, long lifetime and low voltage could be realized.
With regard to the actual demand of current OLED display lighting industry, the development of current OLED material is also nowhere near, and lags behind the requirement of panel manufacturing concern, and the exploitation as the more high performance organic functional material of material enterprise development seems particularly important.
Summary of the invention
For the problems referred to above that prior art exists, the applicant provides a kind of synthesis of novel aromatic compounds and the application in OLED thereof.The OLED that the present invention produces has very high photoelectric properties, can meet the requirement of panel manufacturing concern.
Technical scheme of the present invention is as follows:
An object of the present invention is to base on present the technical development demand of OLED display and lighting enterprise, and provide one can improve OLED luminescent device performance, with 1,3,5-tri-(arylamine group) phenyl, group is the series material of host compound.
Another object of the present invention is to provide a kind of with the application of aromatic amine compounds on OLED taking 1,3,5-tri-(arylamine group) phenyl group as main body.
Another object of the present invention is to the preparation method of above-claimed cpd.
The present invention is realized by following proposal:
A kind of novel aromatic compounds material, this compound is with 1,3,5-tri-(arylamine group) phenyl group for main body, and the formula of its molecular structure is as shown in general formula (1):
In general formula (1), A=B or A ≠ B, and C ≠ D ≠ A, C ≠ D ≠ B;
In general formula (1), A, B and C, D all adopts general formula (2) to represent:
In general formula (2), Ar
1linked by C-N key with the atom N in general formula (1), Ar
1and Ar
2represent benzene, biphenyl, naphthalene, anthracene, phenanthrene, carbazole, fluorenes or other aromatic compounds respectively; R represent carbonatoms be 1 ~ 6 alkyl or carbonatoms be the cycloalkyl of 6 ~ 50, n is 0,1,2,3 ...
The formula of this compound another one molecular structure is general formula (3):
In its formula of (3), R
1, R
2, R
3, R
4, R
5, R
6be respectively benzene, biphenyl, naphthalene, anthracene, luxuriant and rich with fragrance, carbazole, fluorene compound or derivatives thereof; Or for carbonatoms be 1 ~ 6 alkyl or carbonatoms be the cycloalkyl of 6 ~ 50; Wherein R
1, R
2, R
3, R
4, R
5, R
6can be identical or different.
Especially, described R
1, R
2, R
3, R
4, R
5, R
6for hydrogen.
Wherein, A, B, C, D are respectively:
Concrete, the molecular structural formula of this compound is:
Or:
Or:
The preparation method of above-mentioned novel aromatic aminated compounds material, comprises the following steps:
(1) with aromatic bromide and aromatic amine compounds a for raw material, take toluene as solvent, nitrogen protection, adds sodium tert-butoxide, and palladium and tertiary butyl phosphorus are catalyzer, and 100-140 DEG C of backflow, obtains intermediate a;
(2) and then by intermediate a and 3, the bromo-1-chlorobenzene of 5-bis-is raw material, toluene or dimethylbenzene are solvent, nitrogen protection, add sodium tert-butoxide, three (dibenzalacetone) two palladium or palladium, and tertiary butyl phosphorus or normal-butyl two (1-adamantyl) phosphine are catalyzer, 100 ~ 140 DEG C of back flow reaction, obtain intermediate b;
(3) intermediate b and aromatic amine compounds are raw material, and dimethylbenzene is solvent, nitrogen protection, add sodium tert-butoxide, three (dibenzalacetone) two palladium and tertiary butyl phosphorus be catalyzer, 110 ~ 140 DEG C of back flow reaction;
(4) the thick product of target product is purified by means such as column chromatography, making beating and recrystallizations, obtains highly purified white end product after gradient sublimation.
Described aromatic amine compounds a is N-(2-naphthyl)-2-naphthylamines, two (naphthalene-2-base) amine, two (9-(naphthalene-2-base)-9H-carbazole-3-base) amine or other aromatic amine compounds;
Described aromatic amine compounds b is N-phenylaniline, two (4'-methyl-[1,1'-biphenyl]-4-base) amine, two (naphthalene-2-base) amine or other aromatic amine compounds.
The applicant additionally provides a kind of organic electroluminescence device, and by above-mentioned novel aromatic compounds material independently hole-injecting material, independent hole mobile material or hole are injected transport material and used.
Material is used for organic electroluminescent LED.
The technique effect that the present invention is useful is:
OLED material of the present invention can be applicable to OLED luminescent device and makes, and good device performance can be obtained, described material is as the independently hole-injecting material of OLED luminescent device, when transport material use is injected in independent hole mobile material or hole, device drive voltage can obviously reduce, and shows that it has good hole to inject and cavity transmission ability; Meanwhile, the luminous efficiency of device, power efficiency and external quantum efficiency are all greatly improved; Device lifetime is promoted clearly.OLED material of the present invention has good effect in OLED luminescent device, has good industrialization prospect.
Accompanying drawing explanation
Fig. 1 is the structure iron of the OLED of materials application cited by the present invention;
Fig. 2 is the chemical structural formula of the material cited by the present invention.
Embodiment
In order to the technique means of the present invention of understanding clearly and practical purpose, by enumerating embodiment and comparative example, being aided with necessary picture simultaneously and being illustrated.
Embodiment 1 (FDDPR)
The concrete synthetic route of this compound is now provided:
The four-hole bottle of 250ml, under the atmosphere passing into nitrogen, add 27.3 grams of bromo-9,9-dimethyl of (0.1M) 2-) fluorenes, 9.3 grams of (0.1M) aniline, 11.52 grams of (0.12M) sodium tert-butoxides, 0.7 gram of palladium, 0.5 gram of CXA (normal-butyl two (1-adamantyl) phosphine), 200ml toluene, reflux 6 hours, sampling spot plate, reacts completely.Naturally cooling, filter, filtrate revolves steaming, crosses silicagel column, obtains 20.4 grams of faint yellow solids (intermediate a:N-phenyl-9H-9,9-dimethyl fluorene-3-amine), purity 99.12%, yield 71.6%.
The four-hole bottle of 250ml, under the atmosphere passing into nitrogen, add 14.27 grams of (0.05M) N-phenyl-9H-9,9-dimethyl fluorene-3-amine (intermediate a), 6.69 grams of (0.025M) 3, the bromo-1-chlorobenzene of 5-bis-, 3.39 grams of (0.03M) potassium tert.-butoxides, 0.3 gram three (dibenzalacetone) two palladium (pd
2(dba)
3), 0.15 gram of CXA, 150ml dimethylbenzene, reflux 12 hours, sampling spot plate, reacts completely.Naturally cooling, filter, filtrate revolves steaming, crosses silicagel column, obtains 12.0 grams of off-white color solids (chloro-N, the N-bis-(9H-9,9-dimethyl fluorene-2-base) of intermediate b:5--N, N-hexichol-1,3-diamines), purity 98.67%, yield 70.6%.
The four-hole bottle of 250ml, under the atmosphere passing into nitrogen, add 6.8 grams of chloro-N of (0.01M) 5-, N-bis-(9H-9,9-dimethyl fluorene-2-base)-N, N-hexichol-1,3-diamines, 1.9 grams of (0.01M) 4-Methyl-N-phenyl aniline, 2.88 grams of (0.03M) sodium tert-butoxides, 0.3 gram of pd
2(dba)
3, 0.25 gram of tri-tert phosphorus, 100ml toluene, reflux 10 hours, sampling spot plate, reacts completely.Naturally cooling, filter, filtrate revolves steaming, crosses silicagel column, obtains 5.1 grams of faint yellow solids (i.e. target product: FDDPR), purity 99.47%, yield 61.7.
Carry out nuclear magnetic spectrum (1H NMR) analysis to this product, result is as follows:
(200MHz,TMS):5.02(s,3H),6.46(d,5H),7.01(t,6H),6.62(t,3H),6.40(t,5H),6.95(t,3H),2.91(d,4H),2.75(s,2H),3.62(d,3H),5.80(t,4H),5.90(t,5H),6.34(t,2H),6.81(t,2H),2.35(d,3H)
Ultimate analysis structure (molecular formula C
61h
51n
3): theoretical value C, 88.69; H, 6.22; N, 5.09
Test value: C, 88.30; H, 5.80; N, 5.90
Above-mentioned analytical structure shows, material synthesized by the present embodiment and target compound close, simultaneously confirm that synthetic compound is consistent with target compound through nuclear-magnetism and ultimate analysis.
Embodiment 2 (FDTRT)
The concrete synthetic route of this compound is now provided:
The four-hole bottle of 500ml, under the atmosphere passing into nitrogen, add 27.3 grams of bromo-9,9-dimethyl bromine fluorenes of (0.1M) 2-, 14.3 grams of (0.1M) 2-naphthylamines, 11.52 grams of (0.12M) sodium tert-butoxides, 0.7 gram of palladium, 0.5 gram of CXA, 250ml toluene, reflux 6 hours, sampling spot plate, reacts completely.Naturally cooling, filter, filtrate revolves steaming, crosses silicagel column, obtains 21 grams of faint yellow solids (intermediate a2:N-naphthyl-9H-9,9-dimethyl fluorene-3-amine), purity 99.03%, yield 62.7%.
The four-hole bottle of 250ml, under the atmosphere passing into nitrogen, adds 16.8 grams of (0.05M) N-naphthyl-9H-9,9-dimethyl fluorene-3-amine, 6.69 grams (0.025M) 3,5-bis-bromo-1-chlorobenzene, 3.39 grams of (0.03M) potassium tert.-butoxides, 0.3 gram of pd
2(dba)
3, 0.15 gram of CXA, 150ml dimethylbenzene, reflux 12 hours, sampling spot plate, reacts completely.Naturally cooling, filter, filtrate revolves steaming, crosses silicagel column, obtains 12 grams of off-white color solids (chloro-N, the N-bis-(9H-9,9-dimethyl fluorene-2-base) of intermediate b2:5--N, N-dinaphthyl-1,3-diamines), purity 98.77%, yield 61.5%.
The four-hole bottle of 250ml, under the atmosphere passing into nitrogen, add 7.79 grams of chloro-N of (0.01M) 5-, N-bis-(9H-9,9-dimethyl fluorene-2-base)-N, N-dinaphthyl-1,3-diamines, 1.9 grams of (0.01M) 4-Methyl-N-phenyl aniline, 1.15 grams of (0.012M) sodium tert-butoxides, 0.2 gram of pd
2(dba)
3, 0.1 gram of tri-tert phosphorus, 100ml toluene, reflux 10 hours, sampling spot plate, reacts completely.Naturally cooling, filter, filtrate revolves steaming, crosses silicagel column, obtains 7.0 grams of faint yellow solids (target product: FDTRT), purity 99.25%, yield 75.3%.
Carry out nuclear magnetic spectrum (1H NMR) analysis to this product, result is as follows:
(200MHz,TMS):5.02(s,3H),6.46(d,2H),7.01(t,2H),6.62(t,1H),6.40(t,4H),6.95(t,2H),6.76(d,2H),6.51(s,1H),6.79(s,2H),7.51(s,3H),2.91(d,4H),2.75(s,2H),3.62(d,2H),5.80(t,4H),5.90(t,4H),6.34(t,3H),6.81(t,3H),2.35(d,3H),7.553.62(d,2H),7.09(t,2H),7.23(s,2H),7.44(s,2H)
Ultimate analysis structure (molecular formula C
69h
55n
3): theoretical value C, 89.48; H, 5.99; N, 4.54
Test value: C, 89.10; H, 6.00; N, 4.90
Above-mentioned analytical structure shows, material synthesized by the present embodiment and target compound close, simultaneously confirm that synthetic compound is consistent with target compound through nuclear-magnetism and ultimate analysis.
Embodiment 3 (FDPRR)
The concrete synthetic route of this compound is now provided:
The four-hole bottle of 250ml, under the atmosphere passing into nitrogen, add 27.3 grams of bromo-9,9-dimethyl of (0.1M) 2-) fluorenes, 9.3 grams of (0.1M) aniline, 11.52 grams of (0.12M) sodium tert-butoxides, 0.7 gram of palladium, 0.5 gram of CXA, 200ml toluene, reflux 6 hours, sampling spot plate, reacts completely.Naturally cooling, filter, filtrate revolves steaming, crosses silicagel column, obtains 20.4 grams of faint yellow solids (intermediate a3:N-phenyl-9H-9,9-dimethyl-fluorenes-3-amine), purity 99.12%, yield 71.6%.
The four-hole bottle of 50ml, under the atmosphere passing into nitrogen, add 14.27 grams of (0.05M) N-phenyl-9H-9,9-dimethyl fluorene-3-amine (intermediate a), 6.69 grams of (0.025M) 3, the bromo-1-chlorobenzene of 5-bis-, 3.39 grams of (0.03M) potassium tert.-butoxides, 0.3 gram three (dibenzalacetone) two palladium (pd
2(dba)
3), 0.15 gram of CXA, 150ml dimethylbenzene, reflux 12 hours, sampling spot plate, reacts completely.Naturally cooling, filter, filtrate revolves steaming, crosses silicagel column, obtains 12.0 grams of off-white color solids (chloro-N, the N-bis-(9H-9,9-dimethyl fluorene-2-base) of intermediate b3:5--N, N-hexichol-1,3-diamines), purity 98.67%, yield 70.6%.
The four-hole bottle of 250ml, under the atmosphere passing into nitrogen, add 6.8 grams of chloro-N of (0.025M) 5-, N-bis-(9H-9,9-dimethyl fluorene-2-base)-N, N-hexichol-1,3-diamines, 4.93 grams of (0.025M) di-p-tolyl amine, 2.88 grams of (0.03M) sodium tert-butoxides, 0.3 gram of pd
2(dba)
3, 0.25 gram of tri-tert phosphorus, 100ml toluene, reflux 10 hours, sampling spot plate, reacts completely.Naturally cooling, filter, filtrate revolves steaming, crosses silicagel column, obtains 13.6 grams of faint yellow solids (target product: FDPRR), purity 99.64%, yield 64.8%.
Carry out nuclear magnetic spectrum (1H NMR) analysis to this product, result is as follows:
(200MHz,TMS):5.02(s,3H),6.46(d,5H),7.01(t,6H),6.62(t,3H),6.40(t,5H),6.95(t,2H),2.91(d,4H),2.75(s,4H),3.62(d,3H),5.80(t,4H),5.90(t,4H),6.34(t,3H),6.81(t,2H),2.35(d,6H)
Ultimate analysis structure (molecular formula C
62h
53n
3): theoretical value C, 88.64; H, 6.36; N, 5.00
Test value: C, 88.40; H, 6.20; N, 5.40
Above-mentioned analytical structure shows, material synthesized by the present embodiment and target compound close, simultaneously confirm that synthetic compound is consistent with target compound through nuclear-magnetism and ultimate analysis.
Compound of the present invention not only can be expected to use as the hole-injecting material in Fig. 1 structure, can also use, can also use as hole mobile material as hole mobile material.
By the following examples 4 ~ 12 and comparative example 1, comparative example 2, comparative example 3 describe in detail the present invention synthesis the effect of OLED material on device.
Fig. 1 is the device architecture of OLED material of the present invention application, and wherein 1 is transparent substrate layer, and 2 is ITO, and 3 is hole injection layer, and 4 is hole transmission layer, and 5 is luminescent layer, and 6 is electron transfer layer, and 7 is electron injecting layer, and 8 is reflection electrode layer.
Embodiment 4
Ito transparent electrode (thickness is 150nm) is washed, carries out ultraviolet-ozone washing after namely carrying out neutralizing treatment, pure water, drying successively again with the organic residue removing transparent ITO surface.
Having carried out on the ito anode after above-mentioned washing (i.e. transparent substrate layer 1), utilize vacuum deposition apparatus, the material that evaporation embodiment 1 prepares, its thickness has been 10nm, and this layer of organic materials uses as the hole injection layer 3 of luminescent device.And then the TCTA (4,4', 4 "-three (carbazole-9-base) triphenylamine) of evaporation 20nm thickness is as hole transmission layer 4.
After above-mentioned hole mobile material evaporation terminates, make the luminescent layer of OLED luminescent device, its structure comprise OLED luminescent layer 5 use material C BP (4,4'-bis-(9-carbazole) biphenyl) as material of main part, Ir (ppy)
3(three (2-phenylpyridines) close iridium), as phosphorescence dopant material, phosphor material doping ratio is 4% weight ratio, and luminescent layer thickness is 25nm.
After above-mentioned luminescent layer, continuing vacuum evaporation electron transport layer materials is Alq
3(oxine aluminium).The vacuum evaporation thickness of this material is 20nm, and this layer is electron transfer layer 6.
On electron transfer layer 6, by vacuum deposition apparatus, make lithium fluoride (LiF) layer that thickness is 1nm, this layer is electron injecting layer 7.
On electron injecting layer 7, by vacuum deposition apparatus, make aluminium (Al) layer that thickness is 80nm, this layer is that negative electrode reflection electrode layer 8 uses.
After completing OLED luminescent device as described above, with known driving circuit, anode and negative electrode are coupled together, the luminous efficiency of measuring element, the I-E characteristic of luminescent spectrum and device.Its result is presented at table 1.
Embodiment 5
The present embodiment difference from Example 5 is: the material that embodiment 2 prepares changed into by the material of the hole injection layer 3 of OLED luminescent device.
The result of the OLED luminescent device made by embodiment 5 is presented in list 1.
Embodiment 6
The present embodiment difference from Example 5 is: the material that embodiment 3 prepares changed into by the material of the hole injection layer 3 of OLED luminescent device.
The result of the OLED luminescent device made by embodiment 6 is presented in list 1.
Embodiment 7
The present embodiment difference from Example 5 is: the material that embodiment 1 prepares changed into by the material of the hole injection/transport layer (3/4) of OLED luminescent device, evaporation thickness 20nm.
The result of the OLED luminescent device made by embodiment 7 is presented in list 1
Embodiment 8
The present embodiment difference from Example 5 is: the material that embodiment 2 prepares changed into by the material of the hole injection/transport layer (3/4) of OLED luminescent device, evaporation thickness 20nm.
The result of the OLED luminescent device made by embodiment 8 is presented in list 1
Embodiment 9
The present embodiment difference from Example 5 is: the material that embodiment 3 prepares changed into by the material of the hole injection/transport layer (3/4) of OLED luminescent device, evaporation thickness 20nm.
The result of the OLED luminescent device made by embodiment 9 is presented in list 1
Embodiment 10
The present embodiment difference from Example 5 is: hole injection layer 3 material of OLED luminescent device changes NPB (N into by the structural compounds of embodiment 1, N'-phenylbenzene-N, N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamines), evaporation thickness 10nm.The material that embodiment 1 prepares changed into by the material of the hole transmission layer 4 of OLED luminescent device, evaporation thickness 20nm.
The result of the OLED luminescent device made by embodiment 10 is presented in list 1
Embodiment 11
The present embodiment difference from Example 5 is: hole injection layer 3 material of OLED luminescent device changes NPB (N into by the structural compounds of embodiment 1, N'-phenylbenzene-N, N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamines), evaporation thickness 10nm.The material that embodiment 2 prepares changed into by the material of the hole transmission layer 4 of OLED luminescent device, evaporation thickness 20nm.
The result of the OLED luminescent device made by embodiment 11 is presented in list 1
Embodiment 12
The present embodiment difference from Example 5 is: hole injection layer 3 material of OLED luminescent device changes NPB (N into by the structural compounds of embodiment 1, N'-phenylbenzene-N, N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamines), evaporation thickness 10nm.The material that embodiment 3 prepares changed into by the material of the hole transmission layer 4 of OLED luminescent device, evaporation thickness 20nm.
The result of the OLED luminescent device made by embodiment 12 is presented in list 1
Comparative example 1
Comparative example 1 and embodiment 5 difference are: the material of the hole injection layer 3 of OLED luminescent device changes NPB (N, N'-phenylbenzene-N, N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamines) into by the structural compounds of embodiment 1.
Comparative example 2
Comparative example 2 and embodiment 5 difference are: the material that/transport layer (3/4) is injected in the hole of OLED luminescent device changes TCTA (4 into by the structural compounds of embodiment 1,4', 4 "-three (carbazole-9-base) triphenylamine), evaporation thickness 20nm.
Comparative example 3
Comparative example 3 and embodiment 5 difference are: hole injection layer 3 material of OLED luminescent device changes NPB (N into by the structural compounds of embodiment 1, N'-phenylbenzene-N, N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamines), evaporation thickness 10nm.The material of the hole transmission layer 4 of OLED luminescent device changes TCTA (4,4', 4 "-three (carbazole-9-base) triphenylamine) into, evaporation thickness 20nm.
Embodiment 4 to embodiment 6 of the present invention is invention application examples, compared with comparative example 1, described in Application Example 4-6, the manufacture craft of device is identical, and have employed identical baseplate material and electrode materials, the thickness of electrode materials is also consistent, difference has carried out some adjustment to the portion of material used in device, and contrast employs part OLED material of the present invention.
The result that the result of comparative example 1 and the OLED luminescent device made by embodiment 4-6 is presented at the OLED luminescent device in list 1 made by comparative example 1 is presented in list 1.
Table 1
As can be seen from the result of table 1, OLED material of the present invention can be applicable to OLED luminescent device and makes, and can obtain good device performance.When embodiment 1, embodiment 2, material prepared by embodiment 3 use as the hole injection layer 3 of OLED luminescent device, device drive voltage can obviously reduce, and shows that it has good Hole injection capacity; Meanwhile, the luminous efficiency of device, power efficiency and external quantum efficiency are all greatly improved; Device lifetime is promoted clearly.
Embodiment 7 to embodiment 9 of the present invention is invention application examples, compared with comparative example 2, described in Application Example 7-9, the manufacture craft of device is identical, and have employed identical baseplate material and electrode materials, the thickness of electrode materials is also consistent, difference has carried out some adjustment to the portion of material used in device, and contrast employs part OLED material of the present invention.
The result of comparative example 2 and the OLED luminescent device made by embodiment 7-9 is presented in list 2
Table 2
As can be seen from the result of table 2, OLED material of the present invention can be applicable to OLED luminescent device and makes, and can obtain good device performance.When embodiment 1, embodiment 2, material prepared by embodiment 3 use as the hole injection/transport layer (3/4) of OLED luminescent device, device drive voltage can obviously reduce, and shows that it has good hole to inject and transmittability; Meanwhile, the luminous efficiency of device, power efficiency and external quantum efficiency are all greatly improved; Device lifetime is promoted clearly.
Embodiment 10 to embodiment 12 of the present invention is invention application examples, compared with comparative example 3, described in Application Example 10-12, the manufacture craft of device is identical, and have employed identical baseplate material and electrode materials, the thickness of electrode materials is also consistent, difference has carried out some adjustment to the portion of material used in device, and contrast employs part OLED material of the present invention.
The result of comparative example 3 and the OLED luminescent device made by embodiment 10-12 is presented in list 3
Table 3
As can be seen from the result of table 3, OLED material of the present invention can be applicable to OLED luminescent device and makes, and can obtain good device performance.When embodiment 1, embodiment 2, material prepared by embodiment 3 use as the hole transmission layer 4 of OLED luminescent device, device drive voltage can obviously reduce, and shows that it has good cavity transmission ability; Meanwhile, the luminous efficiency of device, power efficiency and external quantum efficiency are all greatly improved; Device lifetime is promoted clearly.
From above market demand, OLED material of the present invention has good effect in OLED luminescent device, has good industrialization prospect.
Although disclose the present invention by embodiment and preferred implementation, should be understood that and the invention is not restricted to disclosed embodiment.On the contrary, it will be understood by those skilled in the art that it is intended to contain various modification and similar arrangement.Therefore, the scope of claims should be consistent with the widest explanation to contain all such modification and similar arrangement.
Claims (8)
1. a novel aromatic compounds material, is characterized in that this compound with 1,3,5-tri-(arylamine group) phenyl group for main body, and the formula of its molecular structure is as shown in general formula (1):
In general formula (1), A=B or A ≠ B, and C ≠ D ≠ A, C ≠ D ≠ B;
In general formula (1), A, B and C, D all adopts general formula (2) to represent:
In general formula (2), Ar
1linked by C-N key with the atom N in general formula (1), Ar
1and Ar
2represent benzene, biphenyl, naphthalene, anthracene, phenanthrene, carbazole, fluorenes or other aromatic compounds respectively; R represent carbonatoms be 1 ~ 6 alkyl or carbonatoms be the cycloalkyl of 6 ~ 50, n is 0,1,2,3 ...
2. novel aromatic compounds material according to claim 1, is characterized in that the formula of the molecular structure of this compound is general formula (3):
General formula (3)
In its formula of (3), R
1, R
2, R
3, R
4, R
5, R
6be respectively benzene, biphenyl, naphthalene, anthracene, luxuriant and rich with fragrance, carbazole, fluorene compound or derivatives thereof; Or for carbonatoms be 1 ~ 6 alkyl or carbonatoms be the cycloalkyl of 6 ~ 50; Wherein R
1, R
2, R
3, R
4, R
5, R
6can be identical or different.
3. novel aromatic compounds material according to claim 2, is characterized in that described R
1, R
2, R
3, R
4, R
5, R
6for hydrogen.
4. novel aromatic compounds material according to claim 1, is characterized in that A, B, C, D are respectively:
5. novel aromatic compounds material according to claim 1, is characterized in that the molecular structural formula of this compound is:
Or:
Or:
6. a preparation method for the novel aromatic aminated compounds material described in any one of Claims 1 to 5, is characterized in that it comprises the following steps:
(1) with aromatic bromide and aromatic amine compounds a for raw material, take toluene as solvent, nitrogen protection, adds sodium tert-butoxide, and palladium and tertiary butyl phosphorus are catalyzer, and 100-140 DEG C of backflow, obtains intermediate a;
(2) and then by intermediate a and 3, the bromo-1-chlorobenzene of 5-bis-is raw material, toluene or dimethylbenzene are solvent, nitrogen protection, add sodium tert-butoxide, three (dibenzalacetone) two palladium or palladium, and tertiary butyl phosphorus or normal-butyl two (1-adamantyl) phosphine are catalyzer, 100 ~ 140 DEG C of back flow reaction, obtain intermediate b;
(3) intermediate b and aromatic amine compounds are raw material, and dimethylbenzene is solvent, nitrogen protection, add sodium tert-butoxide, three (dibenzalacetone) two palladium and tertiary butyl phosphorus be catalyzer, 110 ~ 140 DEG C of back flow reaction;
(4) the thick product of target product is purified by means such as column chromatography, making beating and recrystallizations, obtains highly purified white end product after gradient sublimation.
7. the preparation method of novel aromatic compounds material according to claim 6, its feature is N-(2-naphthyl)-2-naphthylamines, two (naphthalene-2-base) amine, two (9-(naphthalene-2-base)-9H-carbazole-3-base) amine or other aromatic amine compounds in institute in stating aromatic amine compounds a;
Described aromatic amine compounds b is N-phenylaniline, two (4'-methyl-[1,1'-biphenyl]-4-base) amine, two (naphthalene-2-base) amine or other aromatic amine compounds.
8. an organic electroluminescence device, is characterized in that using novel aromatic compounds material according to claim 1 as independently hole-injecting material, and independent hole mobile material or hole are injected transport material and be used for organic electroluminescent LED.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410572979.XA CN104370752B (en) | 2014-10-23 | 2014-10-23 | The synthesis of a kind of 1,3,5-tri-(arylamine group) benzene aromatic compounds and the application in OLED thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410572979.XA CN104370752B (en) | 2014-10-23 | 2014-10-23 | The synthesis of a kind of 1,3,5-tri-(arylamine group) benzene aromatic compounds and the application in OLED thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104370752A true CN104370752A (en) | 2015-02-25 |
| CN104370752B CN104370752B (en) | 2016-07-06 |
Family
ID=52549992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410572979.XA Active CN104370752B (en) | 2014-10-23 | 2014-10-23 | The synthesis of a kind of 1,3,5-tri-(arylamine group) benzene aromatic compounds and the application in OLED thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104370752B (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107098931A (en) * | 2017-05-27 | 2017-08-29 | 南京邮电大学 | A kind of multi-functional amphipathic conjugated molecular material and preparation method and application |
| CN109694328A (en) * | 2017-10-20 | 2019-04-30 | 江苏三月光电科技有限公司 | A kind of triaromatic amine class compound, preparation method and its application in organic electroluminescence device |
| CN109912431A (en) * | 2019-04-09 | 2019-06-21 | 江苏三月光电科技有限公司 | A kind of tri-arylamine group organic compound and its application containing naphthalene |
| CN110003019A (en) * | 2019-04-09 | 2019-07-12 | 江苏三月光电科技有限公司 | It is a kind of using equal benzene as the high mobility organic compound of core and its application |
| CN111170956A (en) * | 2020-01-10 | 2020-05-19 | 黄锦海 | Hole transport material composition containing benzoxazole and thiazole group and application thereof |
| CN111170957A (en) * | 2020-01-10 | 2020-05-19 | 上海百豪新材料有限公司 | Preparation method of hole transport material composition containing benzoxazole and thiazole group |
| CN114075114A (en) * | 2020-08-20 | 2022-02-22 | 江苏三月科技股份有限公司 | Homogeneous benzene arylamine compound and organic electroluminescent device comprising same |
-
2014
- 2014-10-23 CN CN201410572979.XA patent/CN104370752B/en active Active
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107098931A (en) * | 2017-05-27 | 2017-08-29 | 南京邮电大学 | A kind of multi-functional amphipathic conjugated molecular material and preparation method and application |
| CN107098931B (en) * | 2017-05-27 | 2019-02-26 | 南京邮电大学 | Multi-functional amphipathic conjugated molecular material of one kind and the preparation method and application thereof |
| CN109694328A (en) * | 2017-10-20 | 2019-04-30 | 江苏三月光电科技有限公司 | A kind of triaromatic amine class compound, preparation method and its application in organic electroluminescence device |
| CN109694328B (en) * | 2017-10-20 | 2022-03-29 | 江苏三月科技股份有限公司 | Triarylamine compound, preparation method thereof and application thereof in organic electroluminescent device |
| CN109912431A (en) * | 2019-04-09 | 2019-06-21 | 江苏三月光电科技有限公司 | A kind of tri-arylamine group organic compound and its application containing naphthalene |
| CN110003019A (en) * | 2019-04-09 | 2019-07-12 | 江苏三月光电科技有限公司 | It is a kind of using equal benzene as the high mobility organic compound of core and its application |
| CN110003019B (en) * | 2019-04-09 | 2022-08-16 | 江苏三月科技股份有限公司 | High-mobility organic compound with mesitylene as core and application thereof |
| CN109912431B (en) * | 2019-04-09 | 2022-11-15 | 江苏三月科技股份有限公司 | Triarylamine organic compound containing naphthalene and application thereof |
| CN111170956A (en) * | 2020-01-10 | 2020-05-19 | 黄锦海 | Hole transport material composition containing benzoxazole and thiazole group and application thereof |
| CN111170957A (en) * | 2020-01-10 | 2020-05-19 | 上海百豪新材料有限公司 | Preparation method of hole transport material composition containing benzoxazole and thiazole group |
| CN111170957B (en) * | 2020-01-10 | 2023-03-21 | 上海百豪新材料有限公司 | Preparation method of hole transport material composition containing benzoxazole and thiazole groups |
| CN114075114A (en) * | 2020-08-20 | 2022-02-22 | 江苏三月科技股份有限公司 | Homogeneous benzene arylamine compound and organic electroluminescent device comprising same |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104370752B (en) | 2016-07-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106467553B (en) | A kind of boracic organic electroluminescent compounds and its application in OLED device | |
| CN104370752B (en) | The synthesis of a kind of 1,3,5-tri-(arylamine group) benzene aromatic compounds and the application in OLED thereof | |
| JP6864389B2 (en) | Preparation of a metal complex containing a fluorine-substituted structure, an electroluminescent device containing the metal complex, and a compound containing the metal complex. | |
| CN107021926B (en) | Compound containing azaspirofluorene and nitrogen-containing six-membered heterocycle and application of compound in OLED | |
| CN107011248B (en) | Compound and organic electronic device thereof | |
| CN109748909B (en) | Compound containing spiroxanthene fluorene and nitrogen-containing six-membered heterocycle, preparation method thereof and application thereof in organic electroluminescent device | |
| WO2017215549A1 (en) | Organic electroluminescent compound and application thereof | |
| CN105254561A (en) | Organic compound used for OLED and containing fluorene and application thereof | |
| JP2021070681A (en) | Organic electroluminescent material and element | |
| CN106467740B (en) | A kind of organic electroluminescence fluorescent chemicals and its application in electroluminescent device | |
| CN106467544B (en) | A kind of organic fluorescent compounds and its application | |
| CN104356004B (en) | The synthesis of a kind of novel aromatic compounds and the application in OLED thereof | |
| CN112679548B (en) | Organic light-emitting materials with ancillary ligands having partially fluoro substituted substituents | |
| CN106467468A (en) | A kind of organic compound with dibenzo heptene structure and its application | |
| CN105330611B (en) | A kind of compound-material containing double naphthazine structures and its application | |
| CN106467510A (en) | A kind of electroluminescent organic material and its application | |
| CN106543071A (en) | A kind of compound with dibenzo heptenone as core and its application on OLED | |
| JP6940887B2 (en) | Silicon-containing electron transport material and its use | |
| CN110577523A (en) | Compound containing triarylamine structure and organic electroluminescent device prepared from compound | |
| Lee et al. | Deep blue fluorescent host materials based on spirobenzofluorene-fluorene dimers and their properties | |
| CN105384782B (en) | Green phosphorescent organic metal iridium complex and application thereof | |
| KR20140021809A (en) | Aromatic compound derivatives and organic electroluminescent device using the same | |
| CN113354624A (en) | Organic compound and organic light-emitting device using same | |
| CN107778219A (en) | A kind of compound and its application using dibenzo hexatomic ring and nitrogenous hexa-member heterocycle as core | |
| CN107698570B (en) | Compound and organic electronic device thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CP01 | Change in the name or title of a patent holder |
Address after: 214112 No. 210, Xinzhou Road, New District, Jiangsu, Wuxi Patentee after: Jiangsu March Technology Co., Ltd Address before: 214112 No. 210, Xinzhou Road, New District, Jiangsu, Wuxi Patentee before: JIANGSU SUNERA TECHNOLOGY Co.,Ltd. |
|
| CP01 | Change in the name or title of a patent holder |