CN103467450A - Novel organic electroluminescent (EL) material and application thereof in devices - Google Patents
Novel organic electroluminescent (EL) material and application thereof in devices Download PDFInfo
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- CN103467450A CN103467450A CN2013103982981A CN201310398298A CN103467450A CN 103467450 A CN103467450 A CN 103467450A CN 2013103982981 A CN2013103982981 A CN 2013103982981A CN 201310398298 A CN201310398298 A CN 201310398298A CN 103467450 A CN103467450 A CN 103467450A
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Abstract
The invention discloses a novel organic electroluminescent (EL) material and an application thereof in devices. The molecular structural general formula of a carbazole compound is shown in the specification, wherein in the formula, a carbazole group can be connected with other aromatic substituent groups and heterocyclic substituent groups; Ar is an aromatic azacyclo group with carbon number of 15-18. The carbazole compound has high luminescent efficiency. The high luminescent efficiency shows that the compound can be applied to organic EL devices as a luminescent material or a luminescent host material. The carbazole compound is lower in manufacturing cost, prolongs the lives of the organic EL devices and reduces the manufacturing costs of the organic EL devices.
Description
Technical field
The present invention relates to the organic photoelectrical material field, relate in particular to a class new Organic Electro Luminescent Materials and the application in device thereof.
Background technology
Organic electroluminescent (EL) device (hereinafter, referred to as " organic EL device ").Generally by two opposed electrodes and at least one deck organic light emission compound of being inserted between these two electrodes, formed.Electric charge is implanted in the organic layer formed between anode and negative electrode, to form electronics and hole pair, make to have fluorescence or phosphorescent characteristics the organic compound deposits yields light emission.
Research for organic EL Material is from nineteen fifty Bernose, the macromolecule membrane that contains organic pigment to be applied to high current/voltage observation to obtain.Nineteen sixty-five, the people such as Pope have found the Electroluminescence Properties of anthracene single crystal first, and this is the first electro optical phenomenon of organic compound.1987, the people such as the Tang of Kodak found, even the organic luminescent device with separation function lamination formed by organic materials also can provide 1000cd/cm under 10V or less low voltage
2or higher high brightness.
Because the mobility in hole in organic materials is significantly higher than electronic mobility, so can be more effectively to luminescent layer transporting holes and electronics when using suitable hole transmission layer and electron transfer layer.In addition, when the hole density in luminescent layer and electron density balance, can improve luminous efficiency.
When the combination again in organic molecule of electronics, hole, can, because of electron spinning symmetric mode difference, produce the form of two kinds of excited state.A kind of is the singlet excited form that the ground state electronics symmetrical by non-spin forms, and it can release energy and get back to ground state with the form of fluorescence; Another kind is by the triplet excited state form that forms of the symmetrical ground state electronics of spin, with the form of phosphorescence, gives off energy and gets back to ground state.But organic EL device of the prior art only has the short life of 150 hours, because the second-order transition temperature of CBP is very low, only 110 ℃, and the possibility of crystallization is arranged, increase user cost.
Therefore, prior art needs further improve and develop.
Summary of the invention
In view of above-mentioned the deficiencies in the prior art, the object of the present invention is to provide a class new Organic Electro Luminescent Materials and the application in device thereof, be intended to a kind of new efficient electroluminescent organic material.
Technical scheme of the present invention is as follows:
A kind of containing carbazole compound, wherein, the general formula of molecular structure of described carbazole compound is:
Wherein, carbazole group can connect other aromatic substituent and heterocyclic substituent.Ar is the aromatics Azacyclyl that carbonatoms is 15～18.
Described containing carbazole compound, wherein, the aromatics replaced on described carbazole group is substituting group or heterocyclic substituent.
Described containing carbazole compound, wherein, the described carbazole compound that contains is:
In a kind of.
A kind of preparation method containing carbazole compound, it comprises the steps:
Step S1: to the compound, potassium hydroxide and the solvent that add carbazoles substitution compound, Ar group in reaction vessel;
Step S2: reaction system is carried out degassed, then add catalyzer;
Step S4: rising temperature of reaction to 140 ℃-160 ℃ and backflow, fully reaction, obtain described containing carbazole compound.
Described preparation method, wherein, described solvent is oxine and dimethyl sulfoxide (DMSO).
A kind of organic electroluminescent device, wherein, comprise the first electrode, the second electrode and be placed in the one or more carbazole compound layers that contain between described the first electrode, described the second electrode.
A kind of containing the application of carbazole compound in organic electroluminescence device, wherein, the described carbazole compound that contains is used as the green material of main part of phosphorescence, fluorescent green material of main part, hole-injecting material or hole mobile material in described organic electroluminescence device.
A class new Organic Electro Luminescent Materials provided by the invention and the application in device thereof, there is high luminous efficiency containing carbazole compound, high luminous efficiency shows that this compound can be used as luminescent material or luminous material of main part, be applied in organic electroluminescence device, its manufacturing cost is lower, extend the life-span of organic electroluminescence device, reduced the manufacturing cost of organic electroluminescence device.
Embodiment
The invention provides a class new Organic Electro Luminescent Materials and the application in device thereof, clearer, clear and definite for making purpose of the present invention, technical scheme and effect, below the present invention is described in more detail.Should be appreciated that specific embodiment described herein, only in order to explain the present invention, is not intended to limit the present invention.
The invention provides a kind of carbazole compound that contains, wherein, the general formula of molecular structure of described carbazole compound is:
Wherein, carbazole group can connect other aromatic substituent and heterocyclic substituent.Ar is the aromatics Azacyclyl that carbonatoms is 15～18.And the aromatics replaced on described carbazole group is substituting group or heterocyclic substituent.
Further, described is a kind of in sequence number 1-54 in table 1 containing carbazole compound.
Table 1
The present invention also provides a kind of preparation method containing carbazole compound, and it comprises the steps:
Step S1: to the compound, potassium hydroxide and the solvent that add carbazoles substitution compound, Ar group in reaction vessel; Wherein, described solvent is oxine and dimethyl sulfoxide (DMSO);
Step S2: reaction system is carried out degassed, then add catalyzer;
Step S4: rising temperature of reaction to 140 ℃-160 ℃ and backflow, fully reaction, obtain
Described containing carbazole compound.
It is more specifically:
Such as synthesizing of compound 1
Pyrimidine compound 5g (12.81mmol), carbazole 1.93g (11.51mmol), cuprous iodide 0.79g, (4.17mmol), potassium hydroxide 1.17g (2.86mmol), oxine 2.01g (13.91mmol), dimethyl sulfoxide (DMSO) 100mL, and carry out degassedly, be warming up to 150 ℃ of stirrings under nitrogen.Reaction finishes to be cooled to normal temperature (25 ℃), adds methyl alcohol, filters, and the solid of filtration adds distilled water and methanol wash, then uses methylene dichloride and recrystallizing methanol, and the quality obtained containing carbazoles beige solid compound 1 is 3.85g, and productive rate is 70%.
As for the concrete preparation method of synthetic compound 2-54, and the usage quantity of each raw material and each raw material, take and fully react as standard, can determine as required, this is no longer going to repeat them.Only it be the results are shown in to table 2.
Table 2
The present invention also provides a kind of organic electroluminescent device, and it comprises the first electrode, the second electrode and is placed in the one or more carbazole compound layers that contain between described the first electrode, described the second electrode.
And a kind of containing the application of carbazole compound in organic electroluminescence device, its described carbazole compound that contains is used as the green material of main part of phosphorescence, fluorescent green material of main part, hole-injecting material or hole mobile material in described organic electroluminescence device.
For more detailed description the present invention, below enumerate comparative sample and sample of the present invention carries out performance comparison.
Comparative sample
Following chemical formula a is as luminous material of main part, following chemical formula b is as mixing material, 2-TNATA (4,4,4-tri-(N-naphthyl)-N-phenyl amino) be-triphenylamine) hole transporting material, α-NPD (N, N '-bis-(naphthyl)-N, N '-diphenylbenzidine) be hole mobile material, made the organic luminescent device of following structure.
TNATA (80nm)/α-NPD (30nm)/compound a+compound b (30nm)/Alq3 (30nm)/LiF (0.5nm)/Al (60nm).The present embodiment and the EL evaporator that adopts in embodiment DOV company to manufacture are once made device.
15 Ω of Corning society/cm
2 
after the cut-out of ito glass substrate 50mm*50mm*0.7mm size, at acetone, Virahol is respectively cleaned 15 minutes in pure water in microwave, in ultraviolet, cleans 30 minutes again.The 2-TNATA of vacuum evaporation 80nm thickness on substrate, form hole injection layer.Above hole injection layer, the α-NPD of vacuum evaporation 30nm thickness, formed hole transporting layer.The compound that the compound that above hole transporting layer, the chemical formula a of vacuum evaporation 30nm thickness means and chemical formula b mean (doping rate 10%), formed luminescent layer.Above electron supplying layer, a vacuum evaporation LiF0.5nm (electronic injection) and Al60nm have made organic luminescent device.
The compound sample of sequence number 1-54 of the present invention
Adopt the green glow host compound of sequence number compound 1-54 of the present invention to replace compound a in comparative sample, other all adopt method ITO/2-TNATA same in comparative sample (80nm)/α-NPD (30nm)/[a kind of in the green host compound 1～54 of phosphorescence]/b (10%)] (30nm)/Alq
3(30nm) organic luminescent device of the structure of/LiF (0.5nm)/Al (60nm).
Measure the luminescent properties of the compound sample of comparative sample and sequence number 1-54 of the present invention, adopt Keithleysourcemeter " 2400 ", KONIKA MINOLTA " CS-2000 " estimates driving voltage, luminosity, luminous efficiency, glow color.The compound sample of comparative sample and sequence number 1-54 of the present invention.The results are shown in Table 3 for it.
Table 3
Represented according to table 3, the compound sample of comparative sample and sequence number 1-54 of the present invention, comparative sample shows the green emitting peak value in scope 511nm-517nm.And the compounds of this invention luminous efficiency is significantly improved.
Should be understood that, application of the present invention is not limited to above-mentioned giving an example, and for those of ordinary skills, can be improved according to the above description or convert, and all these improvement and conversion all should belong to the protection domain of claims of the present invention.
Claims (7)
1. one kind contains carbazole compound, it is characterized in that, the general formula of molecular structure of described carbazole compound is:
Wherein, carbazole group can connect other aromatic substituent and heterocyclic substituent.Ar is the aromatics Azacyclyl that carbonatoms is 15～18.
2. the carbazole compound that contains according to claim 1, is characterized in that, the aromatics replaced on described carbazole group is substituting group or heterocyclic substituent.
3. the carbazole compound that contains according to claim 1, is characterized in that, the described carbazole compound that contains is:
4. one kind as claimed in claim 1 containing the preparation method of carbazole compound, and it comprises the steps:
Step S1: to the compound, potassium hydroxide and the solvent that add carbazoles substitution compound, Ar group in reaction vessel;
Step S2: reaction system is carried out degassed, then add catalyzer;
Step S4: rising temperature of reaction to 140 ℃-160 ℃ and backflow, fully reaction, obtain described containing carbazole compound.
5. preparation method according to claim 4, is characterized in that, described solvent is oxine and dimethyl sulfoxide (DMSO).
6. an organic electroluminescent device, is characterized in that, comprises the first electrode, the second electrode and be placed in the one or more carbazole compound layers that contain between described the first electrode, described the second electrode.
7. one kind contains the application of carbazole compound in organic electroluminescence device, it is characterized in that, the described carbazole compound that contains is used as the green material of main part of phosphorescence, fluorescent green material of main part, hole-injecting material or hole mobile material in described organic electroluminescence device.
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| WO2016086885A1 (en) * | 2014-12-04 | 2016-06-09 | 广州华睿光电材料有限公司 | Deuterated organic compound, mixture and composition containing said compound, and organic electronic device |
| CN106083721A (en) * | 2015-04-28 | 2016-11-09 | 三星显示有限公司 | Compound and include organic luminescent device and the panel display apparatus of this compound |
| KR101764006B1 (en) | 2014-08-20 | 2017-08-02 | 주식회사 엘지화학 | Organic light emitting diode |
| KR101764976B1 (en) | 2014-09-18 | 2017-08-04 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| CN109791996A (en) * | 2016-12-08 | 2019-05-21 | 广州华睿光电材料有限公司 | High polymer and electroluminescent device |
| CN113896734A (en) * | 2020-07-06 | 2022-01-07 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds, various host materials and organic electroluminescent device comprising the same |
| KR20220005388A (en) | 2020-07-06 | 2022-01-13 | 롬엔드하스전자재료코리아유한회사 | Organic electroluminescent compound, a plurality of host materials and organic electroluminescent device comprising the same |
| DE102021121719A1 (en) | 2020-08-21 | 2022-02-24 | Rohm And Haas Electronic Materials Korea Ltd. | ORGANIC ELECTROLUMINESCENT COMPOUND, MULTIPLE HOST MATERIALS AND THIS COMPREHENSIVE ORGANIC ELECTROLUMINESCENT DEVICE |
| CN114195700A (en) * | 2021-10-28 | 2022-03-18 | 陕西莱特光电材料股份有限公司 | Organic compound, and organic electroluminescent device and electronic device comprising the same |
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| CN113896734A (en) * | 2020-07-06 | 2022-01-07 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds, various host materials and organic electroluminescent device comprising the same |
| KR20220005388A (en) | 2020-07-06 | 2022-01-13 | 롬엔드하스전자재료코리아유한회사 | Organic electroluminescent compound, a plurality of host materials and organic electroluminescent device comprising the same |
| DE102021117045A1 (en) | 2020-07-06 | 2022-01-13 | Rohm And Haas Electronic Materials Korea Ltd. | ORGANIC ELECTROLUMINESCENT COMPOUND, MULTIPLE HOST MATERIALS AND THIS COMPREHENSIVE ORGANIC ELECTROLUMINESCENT DEVICE |
| DE102021121719A1 (en) | 2020-08-21 | 2022-02-24 | Rohm And Haas Electronic Materials Korea Ltd. | ORGANIC ELECTROLUMINESCENT COMPOUND, MULTIPLE HOST MATERIALS AND THIS COMPREHENSIVE ORGANIC ELECTROLUMINESCENT DEVICE |
| CN114195700A (en) * | 2021-10-28 | 2022-03-18 | 陕西莱特光电材料股份有限公司 | Organic compound, and organic electroluminescent device and electronic device comprising the same |
| CN114195700B (en) * | 2021-10-28 | 2022-09-13 | 北京莱特众成光电材料科技有限公司 | Organic compound, and organic electroluminescent device and electronic device comprising the same |
| US11963444B2 (en) | 2021-10-28 | 2024-04-16 | Shaanxi Lighte Optoelectronics Material Co., Ltd. | Organic compound, organic electroluminescent device and electronic apparatus including same |
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