CN102702132A - Novel carbazole derivative and application in organic light-emitting diode device thereof - Google Patents
Novel carbazole derivative and application in organic light-emitting diode device thereof Download PDFInfo
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- CN102702132A CN102702132A CN201010565455XA CN201010565455A CN102702132A CN 102702132 A CN102702132 A CN 102702132A CN 201010565455X A CN201010565455X A CN 201010565455XA CN 201010565455 A CN201010565455 A CN 201010565455A CN 102702132 A CN102702132 A CN 102702132A
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- XMCMOOCZHPIARP-UHFFFAOYSA-N CC(C)(C)c(cc1)ccc1-c1nnc(-c2cccc(-[n](c(ccc(-c3ccccc3)c3)c3c3c4)c3ccc4-c3ccccc3)c2)[o]1 Chemical compound CC(C)(C)c(cc1)ccc1-c1nnc(-c2cccc(-[n](c(ccc(-c3ccccc3)c3)c3c3c4)c3ccc4-c3ccccc3)c2)[o]1 XMCMOOCZHPIARP-UHFFFAOYSA-N 0.000 description 2
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Abstract
The invention discloses a novel carbazole derivative and the application in an organic light-emitting diode device thereof. The carbazole derivative can be simultaneously or independently used as a hole transport layer of the organic light-emitting diode device, a subject or an object of a luminescent layer, or an electron transporting layer.
Description
Technical field
The present invention relates to a kind of novel carbazole (Carbazole) verivate; It can be used as the hole transmission layer of oled device, the main body of luminescent layer (host) or object (guest) or electron transfer layer uses, and relates to a kind of oled device of using it.
Background technology
(Organic Light-Emitting Diode OLED) has advantages such as active illuminating, high contrast, no visual angle limit, response speed is fast to Organic Light Emitting Diode, is considered to be promising indicating meter.The OLED element comprises negative and positive two utmost points and organic layer, and organic layer is made up of hole mobile material, electron transport material and luminescent material.The characteristics such as second-order transition temperature that planarity is good because of having for the carbazoles verivate, π key conjugated degree is high, can effectively transmit electric charge, structure tool rigidity can promote material often are used as hole transmission layer or the luminescent layer material of OLED.
For instance, disclosed phenyl carbazole compound among the CN 1978441, can be used as hole injection layer, hole transmission layer or luminescent layer material with excellent charge transport ability.Then disclosed the carbazole compound of the main body that can be used as blue light phosphorescence twinkler among the WO 2007/069607; With this patented material and FIrpic (two (4; 6-difluorophenyl pyridine) picolinamide iridium (III) (iridium (III) bis (4; 6-difluorophenylpyridinato) picolate)) film of common vapor deposition made, the phosphorescence quantum yield almost can reach 100%.JP 2006-69962 has disclosed the carbazole compound of the main body that can be used on green glow phosphorescence twinkler.Then disclosed carbazole compound among the TW I297038 with high glass-transition temperature; This patent with carbazole material as hole transmission layer and luminescent layer, and with TPBI (1,3; 5-three (the benzene (1 of N-phenyl benzimidazolyl-2 radicals-yl); 3,5-tris (N-phenylbenzimidazole-2-yl) benzene)) be used as electron transfer layer, its element luminous efficacy is 2.51m/W in the time of 5 volts.EP 1972625 has disclosed a series ofly has carbazole Ji the material of oxadiazole structure; Its compound structure characteristics are that three, six positions of carbazole are hydrogen or aliphatic functionality; Though this patent is pointed out its material and is fit to be used as the agent structure of luminescent layer, do not have the real data evidence.Angew.Chem.Int.Ed.2008 mentions a kind of carbazole compound that is suitable for use in the main body of green glow phosphorescence twinkler in 47,8104., and its efficiency of element can reach 20.2%.
In above-mentioned reported in literature, carbazole derivative is widely used in hole transmission layer or the luminescent layer, but is not taken as the electric transmission layer material and uses.In view of this, the present invention develops a kind of novel carbazole derivative that can be used as the electric transmission layer material, can use as hole transmission layer, electron transfer layer and luminescent layer simultaneously, effectively simplifies element and makes flow process.
Summary of the invention
The object of the present invention is to provide a kind of novel carbazole derivative organic materials and be applied in the oled device.With reference to the structural representation of figure 1 oled device, organic electroluminescent element mainly comprises anode 60, organic luminous layer (EML) 40 and negative electrode 10.Anode 60 is made up of the conductive tin indium oxide of the layer of transparent that on glass substrate 70, is plated (ITO) layer.The metal level of negative electrode 10 for for example being formed by aluminium (Al).Comprise hole transmission layer (HTL) 50 between organic luminous layer 40 and the anode 60.Comprise electron transfer layer (ETL) 30 and electron injecting layer (EIL) 20 between organic luminous layer 40 and the negative electrode 10.
Another object of the present invention is to provide a kind of oled device, in this OLED device, use main body or object, hole transmission layer or the electron transfer layer of the aforesaid carbazole derivative organic materials of a kind of the present invention at least as luminescent layer.After in the application examples stated, contain carbazole derivative of the present invention as the main body of the hole transmission layer of oled device, luminescent layer or object and the electron transfer layer material of one deck at least wherein.
Carbazole derivative of the present invention is as shown in the formula (1) represented person:
In the formula (1), R
1～R
10Be selected from hydrogen, OH, NH respectively
2, NO
2, CN, C
1～6Alkoxyl group, C
1～10Alkyl, C
1～20Fluorinated alkyl, C
2～10Thiazolinyl, C
2～10Alkynyl, C
6～20Aromatic base, C
6～20Fluoridize aromatic base, C
4～20Heterocyclic aromatic base; X
1～X
2Be selected from the represented arbitrary structure in following formula (2)～(4),
Wherein, R
11～R
33Be selected from hydrogen, OH, NH respectively
2, NO
2, CN, C
1～6Alkoxyl group, C
1～10Alkyl, C
1～20Fluorinated alkyl, C
2～10Thiazolinyl, C
2～10Alkynyl, C
6～20Aromatic base, C
6～20Fluoridize aromatic base, C
4～20Heterocyclic aromatic base; X
3Be selected from the represented arbitrary structure in following formula (5)～(7),
Wherein, R
34～R
37And R
39～R
48Be selected from hydrogen, OH, NH respectively
2, NO
2, CN, C
1～6Alkoxyl group, C
1～10Alkyl, C
1～20Fluorinated alkyl, C
2～10Thiazolinyl, C
2～10Alkynyl, C
6～20Aromatic base, C
6～20Fluoridize aromatic base, C
4～20Heterocyclic aromatic base, and R
38Be selected from hydrogen, C
1～4Alkyl, C
6～10Aromatic base.
To specify the test of synthesizing and being applied to the OLED element with embodiment below according to a series of carbazole derivative of the present invention.Embodiments of the invention are intended to assist the understanding to content of the present invention; Be not in order to limit the present invention; Any those skilled in the art; Do not breaking away from the spirit and scope of the present invention, when can doing various changes and variation to it, so protection scope of the present invention is when being as the criterion according to the appending claims person of defining.
Description of drawings
Fig. 1 is the structural representation of oled device.
Embodiment
According to an advantageous embodiment of the invention, synthetic below a series of carbazole derivative, and be applied to the test of OLED element.
Work as X
1, X
2Be selected from carbazyl (carbazol), X
3Be selected from 5-(4-tert-butyl-phenyl)-1,3, during the 4-oxadiazole, the chemical formula of this carbazole derivative is following:
Work as X
1, X
2Be selected from phenyl, X
3Be selected from 5-(4-tert-butyl-phenyl)-1,3, during the 4-oxadiazole, the chemical formula of this carbazole derivative is following:
Work as X
1, X
2Be selected from N, and the N-diphenylamine (N, N-diphenylamino), X
3Be selected from 5-(4-tert-butyl-phenyl)-1,3, during the 4-oxadiazole, the chemical formula of this carbazole derivative is following:
Work as X
1, X
2Be selected from phenyl, X
3When being selected from 1-methyl isophthalic acid H-tetrazolium-5-basic (1-Methyl-1H-tetraazol-5-yl), the chemical formula of this carbazole derivative is following:
Work as X
1, X
2Be selected from phenyl, X
3Be selected from 4,5-phenylbenzene-1,3-oxazole-2-base (4,5-diphenyl-1, in the time of 3-oxazol-2-yl), the chemical formula of this carbazole derivative is following:
Below the compound method of carbazole derivative of the present invention is elaborated.
(synthesizing of compound 1)
In 250 milliliters of twoport flasks, add 80 milliliters of N, dinethylformamide (DMF), 2.92 gram (6.85mmol) 3-(3,6-two bromo-9H-carbazole-9-yls) cyanobenzenes, 0.98 gram (15.08mmol) sodiumazide (NaN
3), 0.81 gram (15.08mmol) ammonium chloride (NH
4Cl) and magnetite, refluxed under nitrogen reaction 24 hours, after reaction is accomplished; Add 20 milliliter of 10% spirit of salt (HCl) after-filtration; Use the tubing string chromatography to give purifying, get 3.21 gram white solids 3,6-two bromo-9-(3-1H-tetrazolium-5-base phenyl)-9H-carbazole (productive rate 82.9%).
In one 50 milliliters of twoport flasks, add 2.5 gram (5.33mmol) 3,6-two bromo-9-(3-1H-tetrazolium-5-base phenyl)-9H-carbazole, 4.19 milliliters of (21.45mmol) 4-tert.-butylbenzene formyl chlorides, 35 milliliters of pyridines and magnetite; The refluxed under nitrogen reaction extracted after eight hours; Use the tubing string chromatography to give purifying, get white solid 3,6-two bromo-9-(2-(4-tert-butyl-phenyl)-1; 3,4-oxadiazole base phenyl)-9H-carbazole (productive rate 69.1%).
In 250 milliliters of twoport flasks, add 75 milliliters of toluene, 0.15 gram (0.62mmol) palladium (Pd (OAc)
2) catalyzer, 2.00 gram (20.79mmol) sodium tert-butoxide (NaO
tBu), 50 milliliters of (2.5mmol) tri-butyl phosphine (P
tBu
3), 1.74 the gram (10.39mmol) carbazoles, 2.5 the gram (4.16mmol) 3,6-two bromo-9-(2-(4-tert-butyl-phenyl)-1,3; 4-oxadiazole base phenyl)-and 9H-carbazole and magnetite, reaction refluxed 30 hours, added 10% spirit of salt after reaction is accomplished; Extract with water and ETHYLE ACETATE (EA) again; After the organic layer that obtains concentrated, use the tubing string chromatography to give purifying, white solid (productive rate 31.7%).
In 250 milliliters twoport flask, add 50 milliliters of toluene, 2.7 ml waters, 0.144 gram (0.125mmol) four (triphen phosphino-) palladium (Pd (pph
3)
4) catalyzer, 0.75 restrains (5.4mmol) salt of wormwood, 0.67 gram (5.48mmol) phenyl-boron dihydroxide, 1.5 restrains (2.49mmol) 3,6-two bromo-9-(2-(4-tert-butyl-phenyl)-1,3,4-oxadiazole base phenyl)-9H-carbazole, 5 milliliters of (0.25mmol) p
tBu
3And magnetite, refluxed under nitrogen also stirred 24 hours, after reaction is accomplished, with methylene dichloride and water extraction, with the organic layer that obtains concentrate again solid, use the tubing string chromatography to give purifying, get white solid (productive rate 37%).
In 250 milliliters of twoport flasks, add 75 milliliters of toluene, 0.15 gram (0.62mmol) palladium catalyzer, 2.00 gram (20.79mmol) NaO
tBu, 50 milliliters of (2.5mmol) p
tBu
3, 1.76 the gram (10.39mmol) pentanoic, 2.5 the gram (4.16mmol) 3,6-two bromo-9-(2-(4-tert-butyl-phenyl)-1,3; 4-oxadiazole base phenyl)-and 9H-carbazole and magnetite, reaction refluxed 30 hours, added 10% spirit of salt after reaction is accomplished; Extract with water and ETHYLE ACETATE again; After the organic layer that obtains concentrated, use the tubing string chromatography to give purifying, yellow solid (productive rate 77%).
In 250 milliliters twoport flask, add 30 milliliters of toluene, 12 ml waters, 0.5 gram (0.4mmol) Pd (pph
3)
4, 3.3 gram (24mmol) salt of wormwood, 1.5 gram (12.3mmol) phenyl-boron dihydroxides, 2 gram (4.7mmol) 3-(3,6-two bromo-9H-carbazole-9-yls) cyanobenzenes, 20 milliliters of (1mmol) p
tBu
3And magnetite, refluxed under nitrogen also stirred 24 hours, after reaction is accomplished; With the extraction of methylene dichloride and water, with the organic layer that obtains concentrate again solid, use the tubing string chromatography to give purifying; Get white solid 3-(3,6-phenylbenzene-9H-carbazole-9-yl) cyanobenzene (productive rate 69.8%).
In 250 milliliters of twoport flasks; Add 60 milliliters of Ns, 450 milligrams of (1.07mmol) 3-(3; 6-phenylbenzene-9H-carbazole-9-yl) cyanobenzene, 208.71 milligrams of (3.21mmol) sodiumazide, 171.73 milligrams of (3.21mmol) ammonium chloride and magnetite, 100 ℃ of reactions of constant temperature are 38 hours under nitrogen, after reaction is accomplished; Add 10 milliliter of 10% spirit of salt after-filtration; And with the extraction of ETHYLE ACETATE and water, organic layer drain light orange solid 3,6-phenylbenzene-9-(3-1H-tetrazyl-5-base-phenyl)-9H-carbazole (productive rate 85%).
At 250 milliliters of single port bottles, add 100 milliliters of acetone (acetone), 486 milligrams of (1.05mmol) 3,6-phenylbenzene-9-(3-1H-tetrazyl-5-base-phenyl)-9H-carbazole, 149 milligrams of (1.05mmol) methyl-iodide (CH
3I), 145.1 milligrams of (1.05mmol) salt of wormwood and magnetite, 18 hours after-filtration of back flow reaction, with the tubing string purifying, white solid (productive rate 38%).
At 50 milliliters of single port bottles, add 15 milliliters of toluene, 500 milligrams of (1.17mmol) 3-(3,6-two bromo-9H-carbazole-9-yls) cyanobenzene, 154 milligrams of (0.785mmol) phenylbenzene ethyl ketones (2-Phenylacetophenone), 0.05 milliliter of (0.94mmol) vitriol oil and magnetite; 24 hours after-filtration of back flow reaction; After ETHYLE ACETATE and water extraction, concentrating under reduced pressure gets white solid 3,6-two bromo-9-3-(4; 5-phenylbenzene-1,3-oxazole-2-yl) phenyl-9H-carbazole (productive rate 77.8%).
In 50 milliliters twoport flask, add 15 milliliters of toluene, 1.9 ml waters, 10.9 milligrams of (0.009mmol) Pd (pph
3)
4, 533 milligrams of (3.8mmol) salt of wormwood, 82 milligrams of (0.67mmol) phenyl-boron dihydroxides, 454 milligrams of (0.73mmol) 3,6-two bromo-9-3-(4,5-phenylbenzene-1,3-oxazole-2-yl) phenyl-9H-carbazole, 0.4 milliliter of (0.02mmol) P
tBu
3And magnetite, refluxed under nitrogen also stirred 24 hours, after reaction is accomplished, with methylene dichloride and water extraction, with the organic layer that obtains concentrate again solid, use the tubing string chromatography to give purifying, get white solid (productive rate 50%).
The application example of a plurality of different oled devices is proposed below, the units property detection of going forward side by side, these test results can manifest material of the present invention and have prospect.Test result is listed in table one.
Element one
Anode: indium tin oxide is arranged at (thickness 120nm) on the glass substrate
Hole injection layer: PEDOT (gather (3,4-ethylene oxo thiophene) (Poly (3,4-ethylenedioxythiophene)), 4000rpm)
Hole transmission layer, luminescent layer and electron transfer layer: be all compound 2 (thickness 100nm)
Electron injecting layer: LiF (thickness 0.3nm)
Negative electrode: Al (thickness 100nm)
Element two
Anode: indium tin oxide is arranged at (thickness 120nm) on the glass substrate
Hole transmission layer: compound 2 (thickness 40nm)
Luminescent layer: guest materials three (2-phenylpyridine) iridium (Ir (ppy)
3) and material of main part compound 2 (thickness 30nm)
Hole blocking layer: 2,9-dimethyl--4,7-phenylbenzene-1,10-phenanthrolene (BCP) (thickness 10nm)
Electron transfer layer: compound 2 (thickness 20nm)
Electron injecting layer: LiF (thickness 0.3nm)
Negative electrode: Al (thickness 100nm)
Element three
Anode: indium tin oxide is arranged at (thickness 120nm) on the glass substrate
Hole injection layer: PEDOT (4000rpm)
Hole transmission layer: N, N '-two (naphthalene-1-yl)-N, N '-two (phenyl) p-diaminodiphenyl (NPB) (thickness 40nm)
Luminescent layer: compound 3 (thickness 30nm)
Electron transfer layer: three (oxine) aluminium (Tris (8-hydroxyquinolinato) aluminum, Alq
3) (thickness 30nm)
Electron injecting layer: LiF (thickness 0.3nm)
Negative electrode: Al (thickness 100nm)
Element four
Anode: indium tin oxide is arranged at (thickness 120nm) on the glass substrate
Hole transmission layer: NPB (thickness 40nm)
Luminescent layer: guest materials Ir (ppy)
3And material of main part compound 2 (thickness 30nm)
Hole blocking layer: BCP (thickness 10nm)
Electron transfer layer: Alq
3(thickness 20nm)
Electron injecting layer: LiF (thickness 0.3nm)
Negative electrode: Al (thickness 100nm)
Table one:
| Element | WV (V) | Electric current (mA) | Brightness (cd/m 2) |
| Element one | ?12.79 | 57.99 | 30 |
| Element two | ?12.89 | 0.91 | 1000 |
| Element three | ?7.31 | 4.31 | 1000 |
| Element four | ?6.92 | 5.67 | 10000 |
(industry applications)
Novel carbazole derivative of the present invention; Can be separately as the hole transmission layer of Organic Light Emitting Diode, main body or the object or the electron transfer layer use of luminescent layer; Also can use as hole transmission layer, electron transfer layer and luminescent layer simultaneously, effectively simplify element and make flow process.These materials can be used as the light-emitting device that possesses indicator elment usefulness, Electrofax, illuminating source, indicating meter, recording light source, read-write light source, signal plate, optics communication means or illumination etc.
The main element nomenclature
10 negative electrodes, 20 electron injecting layers (EIL)
30 electron transfer layers (ETL), 40 luminescent layers (EML)
50 hole transmission layers (HTL), 60 anodes
70 substrates.
Claims (7)
1. carbazole derivative has with the represented structure of following formula (1):
In the formula (1), R
1～R
10Be selected from hydrogen, OH, NH respectively
2, NO
2, CN, C
1～6Alkoxyl group, C
1～10Alkyl, C
1～20Fluorinated alkyl, C
2～10Thiazolinyl, C
2～10Alkynyl, C
6～20Aromatic base, C
6～20Fluoridize aromatic base, C
4～20Heterocyclic aromatic base; X
1～X
2Be selected from the represented arbitrary structure in following formula (2)～(4),
Wherein, R
11～R
33Be selected from hydrogen, OH, NH respectively
2, NO
2, CN, C
1～6Alkoxyl group, C
1～10Alkyl, C
1～20Fluorinated alkyl, C
2～10Thiazolinyl, C
2～10Alkynyl, C
6～20Aromatic base, C
6～20Fluoridize aromatic base, C
4～20Heterocyclic aromatic base; X
3Be selected from the represented arbitrary structure in following formula (5)～(7),
Wherein, R
34～R
37And R
39～R
48Be selected from hydrogen, OH, NH respectively
2, NO
2, CN, C
1～6Alkoxyl group, C
1～10Alkyl, C
1～20Fluorinated alkyl, C
2～10Thiazolinyl, C
2～10Alkynyl, C
6～20Aromatic base, C
6～20Fluoridize aromatic base, C
4～20Heterocyclic aromatic base, and R
38Be selected from hydrogen, C
1～4Alkyl, C
6～10Aromatic base.
2. according to the carbazole derivative of claim 1, wherein, X
1, X
2Be selected from carbazyl, and X
3Be selected from 5-(4-tert-butyl-phenyl)-1,3, the 4-oxadiazole, and have following chemical formula:
3. according to the carbazole derivative of claim 1, wherein, X
1, X
2Be selected from phenyl, and X
3Be selected from 5-(4-tert-butyl-phenyl)-1,3, the 4-oxadiazole, and have following chemical formula:
4. according to the carbazole derivative of claim 1, wherein, X
1, X
2Be selected from N, N-diphenylamine, and X
3Be selected from 5-(4-tert-butyl-phenyl)-1,3, the 4-oxadiazole, and have following chemical formula:
5. according to the carbazole derivative of claim 1, wherein, X
1, X
2Be selected from phenyl, and X
3Be selected from 1-methyl isophthalic acid H-tetrazolium-5-base, and have following chemical formula:
6. according to the carbazole derivative of claim 1, wherein, X
1, X
2Be selected from phenyl, and X
3Be selected from 4,5-phenylbenzene-1,3-oxazole-2-base, and have following chemical formula:
7. oled device; It is characterized by: between pair of electrodes, include according to each carbazole derivative in the claim 1 to 6, this carbazole derivative is to use hole transmission layer, electron transfer layer or luminescent layer main body or the guest materials as this oled device.
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| WO2017101675A1 (en) * | 2015-12-18 | 2017-06-22 | 昆山国显光电有限公司 | Thermally activated delayed fluorescence material and use thereof in organic electroluminescent device |
| CN106892857A (en) * | 2015-12-18 | 2017-06-27 | 昆山国显光电有限公司 | Thermal activation delayed fluorescence material and its application in organic electroluminescence device |
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| US11104669B2 (en) | 2018-02-02 | 2021-08-31 | Kyulux, Inc. | Composition of matter for use in organic light-emitting diodes |
| US11608333B2 (en) | 2018-03-20 | 2023-03-21 | Kyulux, Inc. | Composition of matter for use in organic light-emitting diodes |
| US11498914B2 (en) | 2018-03-30 | 2022-11-15 | Kyulux, Inc. | Composition of matter for use in organic light-emitting diodes |
| CN110606821A (en) * | 2019-07-24 | 2019-12-24 | 三明学院 | Organic monomolecular material bromocarbazole benzophenone derivative for emitting white light and preparation method thereof |
| CN110606821B (en) * | 2019-07-24 | 2023-04-18 | 三明学院 | Organic monomolecular material bromocarbazole benzophenone derivative for emitting white light and preparation method thereof |
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