CN103467447A - 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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- CN103467447A CN103467447A CN2013103982996A CN201310398299A CN103467447A CN 103467447 A CN103467447 A CN 103467447A CN 2013103982996 A CN2013103982996 A CN 2013103982996A CN 201310398299 A CN201310398299 A CN 201310398299A CN 103467447 A CN103467447 A CN 103467447A
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- 0 CC1C(c2cc(CCCC3)c3c(*c3)*2c2c3c(CCCC3)c3[n]2C2=CCCC=C2)=NC2NC=CC=C2C1C1=CC=CCC1 Chemical compound CC1C(c2cc(CCCC3)c3c(*c3)*2c2c3c(CCCC3)c3[n]2C2=CCCC=C2)=NC2NC=CC=C2C1C1=CC=CCC1 0.000 description 4
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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 quinoline derivative is shown in the specification, wherein in the formula, W, Z, X and Y are one of carbon atoms or nitrogen atoms; an Ar1 group is aryl with carbon number of 6-14; an Ar2 group is an aromatic heterocyclic radical with carbon number of 12-30. The quinoline derivative 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 quinoline derivative is lower in manufacturing cost, prolongs the service 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 apply in device.
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 electroluminescence 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 apply in device, aim to provide a kind of new efficient electroluminescent organic material.
Technical scheme of the present invention is as follows:
A kind of containing quinoline derivatives, wherein, the general formula of molecular structure of described quinoline derivatives is:
Wherein, W, Z, X, Y are a kind of in carbon atom or nitrogen-atoms; Ar
1group is the aryl that carbonatoms is 6～14, Ar
2group is the aromatic heterocyclic radical that carbonatoms is 12～30.
Described containing quinoline derivatives, wherein, described Ar
1group is a kind of in phenyl, xenyl, 2-naphthyl, 2-anthryl, N-phenyl-3-carbazyl or 2-phenanthryl.
Described containing quinoline derivatives, wherein, the described quinoline derivatives that contains is:
in a kind of.
A kind of described preparation method containing quinoline derivatives, it comprises the steps:
Step S1: to adding the chloro-4-phenylquinoline of 2-analog derivative in reaction vessel, containing Ar
2the aminated compounds of group, potassium hydroxide and solvent:
Step S2: reaction system is carried out degassed, then add catalyzer;
Step S3: rising temperature of reaction to 140 ℃-160 ℃ and backflow, fully reaction, obtain described containing quinoline derivatives.
Described preparation method, wherein, described solvent is oxine and dimethyl sulfoxide (DMSO).
Described preparation method, wherein, the chloro-4-phenylquinoline of the 2-in described step S1 analog derivative is prepared from by 2-chlorine-4-iodine base quinoline derivatives.
Described preparation method, wherein, the step for preparing the chloro-4-phenylquinoline of described 2-analog derivative comprises:
Step N1: to adding 2-chlorine-4-iodine base quinoline derivatives in reaction vessel, containing Ar
1boric acid, salt of wormwood and solvent that group replaces;
Step N2: reaction system is carried out degassed, then add catalyzer, rising temperature of reaction to 140 ℃-160 ℃ also refluxes, fully reaction;
Step N3: through extraction, washing, drying, column chromatography purification, obtain the chloro-4-phenylquinoline of described 2-analog derivative.
A kind of organic electroluminescent device, wherein, comprise the first electrode, the second electrode and be placed in the one or more quinoline derivatives layers that contain between described the first electrode, described the second electrode.
A kind of containing the application of quinoline derivatives in organic electroluminescence device, wherein, the described quinoline derivatives that contains is used as phosphorescent red material of main part, fluorescent red 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 applying in device, there is high luminous efficiency containing quinoline derivatives, 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 apply in device, 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 quinoline derivatives that contains, the general formula of molecular structure of wherein said quinoline derivatives is:
W, Z, X, Y are a kind of in carbon atom or nitrogen-atoms; Ar
1group is the aryl that carbonatoms is 6～14, Ar
2group is the aromatic heterocyclic radical that carbonatoms is 12～30.
And described Ar
1group is a kind of in phenyl, xenyl, 2-naphthyl, 2-anthryl, N-phenyl-3-carbazyl or 2-phenanthryl.
Further, described is a kind of in sequence number 1-46 in table 1 containing quinoline derivatives.
Table 1
The present invention also provides a kind of described preparation method containing quinoline derivatives, and it comprises the steps:
Step S1: to adding the chloro-4-phenylquinoline of 2-analog derivative in reaction vessel, containing Ar
2the aminated compounds of group, potassium hydroxide and solvent:
Step S2: reaction system is carried out degassed, then add catalyzer;
Step S3: rising temperature of reaction to 140 ℃-160 ℃ and backflow, fully reaction, obtain described containing quinoline derivatives.Wherein, described solvent is oxine and dimethyl sulfoxide (DMSO).
Further, the chloro-4-phenylquinoline of the 2-analog derivative in described step S1 is prepared from by 2-chlorine-4-iodine base quinoline derivatives.Its step comprises:
Step N1: to adding 2-chlorine-4-iodine base quinoline derivatives in reaction vessel, containing Ar
1boric acid, salt of wormwood and solvent that group replaces;
Step N2: reaction system is carried out degassed, then add catalyzer, rising temperature of reaction to 140 ℃-160 ℃ also refluxes, fully reaction;
Step N3: through extraction, washing, drying, column chromatography purification, obtain the chloro-4-phenylquinoline of described 2-analog derivative.
In order further to describe preparation method of the present invention, the sequence number of take is 9 is described in detail as example containing quinoline derivatives.
Prepare compound 9
By 2-chlorine-4-iodine quinazoline 50g (172.122mmol); phenylo boric acid 25.19g (206.54mmol), be dissolved in 1L toluene, and carry out degassed; add tetra-triphenylphosphine palladium 11.7g (10.15mmol) under nitrogen protection; salt of wormwood 10.52g (761.28mmol), distilled water 100mL, stirring and refluxing reaction 24 hours; after finishing, reaction adds distilled water under normal temperature; be extracted with ethyl acetate collected organic layer, use anhydrous magnesium sulfate drying, filter.Obtain liquid after underpressure distillation, then column chromatography, drawing the chloro-4-phenylquinoline of white solid intermediate 2-derivative 28.9g, productive rate is 70%.
Then by white solid intermediate 2-chloro-4-phenylquinoline analog derivative 5g (20.77mmol); carbazole 4.16g (24.92mmol); cupric iodide 0.79g (4.17mmol); potassium hydroxide 1.17g (2.86mmol); oxine 2.01g (13.91mmol); dimethyl sulfoxide (DMSO) (DMSO) 100mL, under the nitrogen protection condition, under be warming up to 150 ℃ of stirrings.Reaction finishes to be cooled under normal temperature (25 ℃) condition, adds methyl alcohol, then the solid filtering generated, again the solid of filtration is added to distilled water and methanol wash, use again methylene dichloride and recrystallizing methanol, draw sequence number be 9 containing quinoline derivatives 5.4g, productive rate is 70%.
As for the concrete preparation method of synthetic residue sequence number compound, and the usage quantity of 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 quinoline derivatives layers that contain between described the first electrode, described the second electrode.
And a kind of containing the application of quinoline derivatives in organic electroluminescence device, its described quinoline derivatives that contains is used as phosphorescent red material of main part, fluorescent red 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 dopant material, the 2-TNATA (4,4 that chemical formula c means, 4-tri-(N-naphthyl)-N-phenyl amino) be-triphenylamine) hole transporting material, made the organic electroluminescence device of following structure.
The TNATA that chemical formula d is meaned (80nm)/α-NPD (30nm)/compound a+compound b (30nm)/Alq
3(30nm)/LiF (0.5nm)/Al (60nm).The EL evaporator that adopts DOV company to manufacture in the present embodiment and following examples is made device, makes the contrast organic electroluminescence device.
The compound sample of sequence number 1-46 of the present invention
Adopt the cavitation compound of sequence number compound 1-46 of the present invention to replace compound a in comparative sample, except other employings be method ITO/DNTPD (80nm) same in comparative sample/α-NPD (30nm)/[cavitation compound order 1～46 and doped compound]/b (8.0%)] (25nm)/Alq
3(30nm) organic luminescent device of the structure of/LiF (0.5nm)/Al (60nm).
Measure 1: the luminescent properties of the compound sample of comparative sample and sequence number 1-46
The compound sample of measuring comparative sample and sequence number 1-46 is to adopt KeithleySMU235, and PR650 estimates driving voltage, luminosity, luminous efficiency, glow color.The compound sample of comparative sample and sequence number 1-46 is tested equally, and the results are shown in Table 3.
Table 3
Represented according to table 3, the compound sample of comparative sample and sequence number 1-46, above-mentioned comparative sample shows that in the 632-640nm wavelength region glow color is red, the described quinoline derivatives luminous efficiency that contains is significantly improved.
Measure: the life characteristic evaluation of the compound sample of comparative sample and sequence number 1-46
What adopt is the life-span determination device of the LTS-1004AC of ENC company, and the 3000nit of take has measured each life-span as benchmark and reached for 97% time, and result is illustrated in table 4.
Table 4
| Sample No. | Host compound | Doped compound | Life-span [h] |
| Comparative sample | a | b | 72 |
| 1 | 1 | b | 180 |
| 2 | 2 | b | 153 |
| 3 | 3 | b | 197 |
| 4 | 4 | b | 105 |
| 5 | 5 | b | 120 |
| 6 | 6 | b | 98 |
| 7 | 7 | b | 90 |
| 8 | 8 | b | 188 |
| 9 | 9 | b | 138 |
| 10 | 10 | b | 172 |
| 11 | 11 | b | 122 |
| 12 | 12 | b | 130 |
| 13 | 13 | b | 195 |
| 14 | 14 | b | 186 |
| 15 | 15 | b | 174 |
| 16 | 16 | b | 160 |
| 17 | 17 | b | 91 |
| 18 | 18 | b | 164 |
| 19 | 19 | b | 116 |
| 20 | 20 | b | 117 |
| 21 | 21 | b | 90 |
| 22 | 22 | b | 100 |
| 23 | 23 | b | 107 |
| 24 | 24 | b | 101 |
| 25 | 25 | b | 96 |
| 26 | 26 | b | 199 |
| 27 | 27 | b | 101 |
| 28 | 28 | b | 98 |
| 29 | 29 | b | 152 |
| 30 | 30 | b | 112 |
| 31 | 31 | b | 114 |
| 32 | 32 | b | 102 |
| 33 | 33 | b | 97 |
| 34 | 34 | b | 104 |
| 35 | 35 | b | 108 |
| 36 | 36 | b | 103 |
| 37 | 37 | b | 94 |
| 38 | 38 | b | 98 |
| 39 | 39 | b | 181 |
| 40 | 40 | b | 116 |
| 41 | 41 | b | 100 |
| 42 | 42 | b | 92 |
| 43 | 43 | b | 93 |
| 44 | 44 | b | 116 |
| 45 | 45 | b | 97 |
| 46 | 46 | b | 116 |
According to table 4, can determine, comparative sample is compared with the compound sample of sequence number 1-46, and described quinoline derivatives luminescent lifetime 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 (9)
1. one kind contains quinoline derivatives, it is characterized in that, the general formula of molecular structure of described quinoline derivatives is:
Wherein, W, Z, X, Y are a kind of in carbon atom or nitrogen-atoms; Ar
1group is the aryl that carbonatoms is 6～14, Ar
2group is the aromatic heterocyclic radical that carbonatoms is 12～30.
2. according to claim 1 containing quinoline derivatives, it is characterized in that described Ar
1group is a kind of in phenyl, xenyl, 2-naphthyl, 2-anthryl, N-phenyl-3-carbazyl or 2-phenanthryl.
3. the quinoline derivatives that contains according to claim 1, is characterized in that, the described quinoline derivatives that contains is:
in a kind of.
4. one kind as claimed in claim 1 containing the preparation method of quinoline derivatives, and it comprises the steps:
Step S1: to adding the chloro-4-phenylquinoline of 2-analog derivative in reaction vessel, containing Ar
2the aminated compounds of group, potassium hydroxide and solvent:
Step S2: reaction system is carried out degassed, then add catalyzer;
Step S3: rising temperature of reaction to 140 ℃-160 ℃ and backflow, fully reaction, obtain described containing quinoline derivatives.
5. preparation method according to claim 4, is characterized in that, described solvent is oxine and dimethyl sulfoxide (DMSO).
6. preparation method according to claim 4, is characterized in that, the chloro-4-phenylquinoline of the 2-in described step S1 analog derivative is prepared from by 2-chlorine-4-iodine base quinoline derivatives.
7. preparation method according to claim 6, is characterized in that, the step for preparing the chloro-4-phenylquinoline of described 2-analog derivative comprises:
Step N1: to adding 2-chlorine-4-iodine base quinoline derivatives in reaction vessel, containing Ar
1boric acid, salt of wormwood and solvent that group replaces;
Step N2: reaction system is carried out degassed, then add catalyzer, rising temperature of reaction to 140 ℃-160 ℃ also refluxes, fully reaction;
Step N3: through extraction, washing, drying, column chromatography purification, obtain the chloro-4-phenylquinoline of described 2-analog derivative.
8. an organic electroluminescent device, is characterized in that, comprises the first electrode, the second electrode and be placed in the one or more quinoline derivatives layers that contain between described the first electrode, described the second electrode.
9. one kind contains the application of quinoline derivatives in organic electroluminescence device, it is characterized in that, the described quinoline derivatives that contains is used as phosphorescent red material of main part, fluorescent red material of main part, hole-injecting material or hole mobile material in described organic electroluminescence device.
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| KR101513006B1 (en) | 2012-06-13 | 2015-04-17 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescence compounds and organic electroluminescence device containing the same |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102439004A (en) * | 2010-04-20 | 2012-05-02 | 出光兴产株式会社 | Bicarbazole derivative, material for organic electroluminescent element, and organic electroluminescent element using same |
| CN102625806A (en) * | 2009-07-31 | 2012-08-01 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| WO2012121561A1 (en) * | 2011-03-08 | 2012-09-13 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN103242299A (en) * | 2013-05-16 | 2013-08-14 | 吉林大学 | Quinazoline derivative and application thereof in organic electroluminescent device |
-
2013
- 2013-09-04 CN CN201310398299.6A patent/CN103467447B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102625806A (en) * | 2009-07-31 | 2012-08-01 | 罗门哈斯电子材料韩国有限公司 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN102439004A (en) * | 2010-04-20 | 2012-05-02 | 出光兴产株式会社 | Bicarbazole derivative, material for organic electroluminescent element, and organic electroluminescent element using same |
| WO2012121561A1 (en) * | 2011-03-08 | 2012-09-13 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| CN103242299A (en) * | 2013-05-16 | 2013-08-14 | 吉林大学 | Quinazoline derivative and application thereof in organic electroluminescent device |
Cited By (17)
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| CN105794010A (en) * | 2013-12-18 | 2016-07-20 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compound, and multi-component host material and organic electroluminescent device comprising the same |
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| CN106068267A (en) * | 2014-03-17 | 2016-11-02 | 罗门哈斯电子材料韩国有限公司 | Electronics padded coaming and the Organnic electroluminescent device comprising it |
| EP3119767A4 (en) * | 2014-03-17 | 2017-11-08 | Rohm And Haas Electronic Materials Korea Ltd. | Electron buffering material and organic electroluminescent device comprising the same |
| KR20150124914A (en) * | 2014-04-29 | 2015-11-06 | 유니버셜 디스플레이 코포레이션 | Organic electroluminescent materials and devices |
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| US20150311449A1 (en) * | 2014-04-29 | 2015-10-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US9741941B2 (en) * | 2014-04-29 | 2017-08-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10011608B2 (en) | 2014-07-21 | 2018-07-03 | Duk San Neolux Co., Ltd. | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| WO2016013817A3 (en) * | 2014-07-21 | 2016-08-11 | 덕산네오룩스 주식회사 | Compound for organic electric element, organic electric element using same, and electronic device thereof |
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| WO2016198144A1 (en) | 2015-06-10 | 2016-12-15 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
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