CN102702132B - Novel carbazole derivative and organic light-emitting diode device applied thereof - Google Patents
Novel carbazole derivative and organic light-emitting diode device applied thereof Download PDFInfo
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- CN102702132B CN102702132B CN201010565455.XA CN201010565455A CN102702132B CN 102702132 B CN102702132 B CN 102702132B CN 201010565455 A CN201010565455 A CN 201010565455A CN 102702132 B CN102702132 B CN 102702132B
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- 0 Cc1c(C)c(*)c(*)c(*)c1C Chemical compound Cc1c(C)c(*)c(*)c(*)c1C 0.000 description 6
- ZDAWFUBVMHHVCZ-UHFFFAOYSA-N CC(C)(C)c1ccc(C(N)[U]C(c2cccc(-[n]3c(ccc(-[n]4c(cccc5)c5c5c4CCC=C5)c4)c4c4c3CCC(N3c5ccccc5C5C3CCCC5)=C4)c2)=N)cc1 Chemical compound CC(C)(C)c1ccc(C(N)[U]C(c2cccc(-[n]3c(ccc(-[n]4c(cccc5)c5c5c4CCC=C5)c4)c4c4c3CCC(N3c5ccccc5C5C3CCCC5)=C4)c2)=N)cc1 ZDAWFUBVMHHVCZ-UHFFFAOYSA-N 0.000 description 1
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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) derivative, it can be used as the hole transmission layer of oled device, the main body (host) of luminescent layer or object (guest) or electron transfer layer uses, and relates to a kind of oled device applying it.
background technology
Organic Light Emitting Diode (Organic Light-Emitting Diode, OLED) has active illuminating, high contrast, without the advantage such as angle limitations, fast response time, is considered to be promising indicating meter.OLED element comprises negative and positive two pole and organic layer, and organic layer is made up of hole mobile material, electron transport material and luminescent material.Because having, planarity is good, π key conjugated degree is high for carbazoles derivative, effectively can transmit electric charge, structure tool rigidity can promote the characteristics such as the second-order transition temperature of material, is often used as hole transmission layer or the emitting layer material of OLED.
For example, disclose the phenyl carbazole compound with excellent charge transport ability in CN1978441, can be used as hole injection layer, hole transmission layer or emitting layer material.The carbazole compound of the main body that can be used as blue emitting phosphor twinkler is then disclosed in WO2007/069607, with this patented material and FIrpic (two (4,6-difluorophenyl pyridinato) picolinamide iridium (III) (iridium (III) bis (4,6-difluorophenylpyridinato) picolate)) common film made by evaporation, phosphorescence quantum yield almost can reach 100%.JP2006-69962 discloses the carbazole compound of the main body that can be used on green glow phosphorescent emitter.The carbazole compound with high glass-transition temperature is then disclosed in TW I297038, this patent using carbazole material as hole transmission layer and luminescent layer, and with TPBI(1,3,5-tri-(N-phenylbenzimidazol-2-base) benzene (1,3,5-tris (N-phenylbenzimidazole-2-yl) benzene)) be used as electron transfer layer, its element luminous efficacy is 2.51m/W 5 volts time.EP 1972625 discloses a series ofly has carbazole Ji the material of oxadiazole structure, its compound structure feature is three, six positions of carbazole is hydrogen or aliphatic functionality, although this patent points out that its material is applicable to being used as the agent structure of luminescent layer, there is no real data evidence.Angew.Chem.Int.Ed.2008,47, mention a kind of carbazole compound being suitable for use in the main body of green glow phosphorescent emitter in 8104., its efficiency of element can reach 20.2%.
In above-mentioned reported in literature, carbazole derivative is widely used in hole transmission layer or luminescent layer, is not but taken as electron transport layer materials and uses.In view of this, the present invention develops a kind of novel carbazole derivative that can be used as electron transport layer materials, can use simultaneously, effectively simplify element Making programme as hole transmission layer, electron transfer layer and luminescent layer.
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 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 plated on glass substrate 70 (ITO) layer.The metal level of negative electrode 10 for being such as made up of aluminium (Al).Hole transmission layer (HTL) 50 is comprised between organic luminous layer 40 and anode 60.Electron transfer layer (ETL) 30 and electron injecting layer (EIL) 20 is comprised between organic luminous layer 40 and negative electrode 10.
Another object of the present invention is to provide a kind of oled device, in this OLED device, at least use the aforesaid carbazole derivative organic materials of a kind of the present invention as the main body of luminescent layer or object, hole transmission layer or electron transfer layer.In application examples described later, containing the material of carbazole derivative of the present invention as the hole transmission layer of oled device, the main body of luminescent layer or object and electron transfer layer wherein at least one deck.
Carbazole derivative of the present invention is as shown in the formula (1) represented person:
In 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 ~ 20fluorinated aromatic base, C
4 ~ 20heterocyclic aromatic base; X
1~ X
2be selected from the arbitrary structure represented by 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 ~ 20fluorinated aromatic base, C
4 ~ 20heterocyclic aromatic base; X
3be selected from the arbitrary structure represented by 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 ~ 20fluorinated aromatic base, C
4 ~ 20heterocyclic aromatic base, and R
38be selected from hydrogen, C
1 ~ 4alkyl, C
6 ~ 10aromatic base.
To illustrate with embodiment according to the synthesis of a series of carbazole derivative of the present invention and the test being applied to OLED element below.Embodiments of the invention are intended to assist the understanding to content of the present invention; and be not used to limit the present invention; any those skilled in the art; without departing from the spirit and scope of the present invention; when doing various change and change to it, therefore protection scope of the present invention is when being as the criterion according to the appending claims person of defining.
Accompanying drawing explanation
Fig. 1 is the structural representation of oled device.
Embodiment
According to an advantageous embodiment of the invention, the following a series of carbazole derivative of synthesis, and be applied to the test of OLED element.
Work as X
1, X
2be selected from carbazyl (carbazol), X
3when being selected from 5-(4-tert-butyl-phenyl)-1,3,4-oxadiazole, the chemical formula of this carbazole derivative is as follows:
Work as X
1, X
2be selected from phenyl, X
3when being selected from 5-(4-tert-butyl-phenyl)-1,3,4-oxadiazole, the chemical formula of this carbazole derivative is as follows:
Work as X
1, X
2be selected from N, N-diphenylamine (N, N-diphenylamino), X
3when being selected from 5-(4-tert-butyl-phenyl)-1,3,4-oxadiazole, the chemical formula of this carbazole derivative is as follows:
Work as X
1, X
2be selected from phenyl, X
3when being selected from 2-methyl isophthalic acid H-tetrazolium-5-base (2-Methyl-1H-tetraazol-5-yl), the chemical formula of this carbazole derivative is as follows:
Work as X
1, X
2be selected from phenyl, X
3when being selected from 4,5-phenylbenzene-1,3-oxazole-2-base (4,5-diphenyl-1,3-oxazol-2-yl), the chemical formula of this carbazole derivative is as follows:
Below the synthetic method of carbazole derivative of the present invention is elaborated.
(synthesis of compound 1)
In 250 milliliters of twoport flasks, add 80 milliliters of N, dinethylformamide (DMF), 2.92 grams of (6.85mmol) 3-(the bromo-9H-carbazole of 3,6-bis--9-base) cyanobenzenes, 0.98 gram of (15.08mmol) sodiumazide (NaN
3), 0.81 gram of (15.08mmol) ammonium chloride (NH
4and magnetite Cl), back flow reaction 24 hours under a nitrogen, after having reacted, add 20 milliliter of 10% spirit of salt (HCl) to filter afterwards, col-umn chromatography is used to give purifying, obtain the 3.21 grams of bromo-9-of white solid 3,6-bis-(3-2H-tetrazolium-5-base phenyl)-9H-carbazoles (productive rate 82.9%).
In one 50 milliliters of twoport flasks, add 2.5 grams of (5.33mmol) 3, the bromo-9-of 6-bis-(3-2H-tetrazolium-5-base phenyl)-9H-carbazole, 4.19 milliliters of (21.45mmol) 4-tert-butyl benzoyl chloride, 35 milliliters of pyridines and magnetites, refluxed under nitrogen extracts after reacting eight hours, col-umn chromatography is used to give purifying, obtain white solid 3, the bromo-9-of 6-bis-(3-(5-(4-tert-butyl-phenyl)-1,3,4-oxadiazole-2-base) phenyl)-9H-carbazole (productive rate 69.1%).
In 250 milliliters of twoport flasks, add 75 milliliters of toluene, 0.15 gram of (0.62mmol) palladium (Pd (OAc)
2) catalyzer, 2.00 grams of (20.79mmol) sodium tert-butoxide (NaO
tbu), 50 milliliters of (2.5mmol) tri-butyl phosphine (P
tbu
3), 1.74 grams of (10.39mmol) carbazoles, 2.5 grams of (4.16mmol) 3, the bromo-9-of 6-bis-(3-(5-(4-tert-butyl-phenyl)-1,3,4-oxadiazole-2-base) phenyl)-9H-carbazole and magnetite, reaction backflow 30 hours, 10% spirit of salt is added after having reacted, extract with water and ethyl acetate (EA) again, after the organic layer obtained is concentrated, use col-umn chromatography to give purifying, obtain white solid (productive rate 31.7%).
(synthesis of compound 2)
50 milliliters of toluene, 2.7 ml waters, 0.144 gram (0.125mmol) four (triphen phosphino-) palladium (Pd (pph is added in the twoport flask of 250 milliliters
3)
4) catalyzer, 0.75 gram of (5.4mmol) salt of wormwood, 0.67 gram of (5.48mmol) phenyl-boron dihydroxide, 1.5 grams of (2.49mmol) 3, the bromo-9-of 6-bis-(3-(5-(4-tert-butyl-phenyl)-1,3,4-oxadiazole-2-base) phenyl)-9H-carbazole, 5 milliliters of (0.25mmol) P
tbu
3and magnetite, refluxed under nitrogen also stirs 24 hours, after having reacted, and extracts with methylene dichloride and water, and the organic layer obtained is concentrated to obtain solid again, uses col-umn chromatography to give purifying, obtains white solid (productive rate 37%).
(synthesis of compound 3)
In 250 milliliters of twoport flasks, add 75 milliliters of toluene, 0.15 gram of (0.62mmol) palladium acetate catalyst, 2.00 grams of (20.79mmol) NaO
tbu, 50 milliliters of (2.5mmol) P
tbu
3, 1.76 grams of (10.39mmol) pentanoic, 2.5 grams of (4.16mmol) 3, the bromo-9-of 6-bis-(3-(5-(4-tert-butyl-phenyl)-1,3,4-oxadiazole-2-base) phenyl)-9H-carbazole and magnetite, reaction backflow 30 hours, adds 10% spirit of salt after having reacted, extract with water and ethyl acetate again, after the organic layer obtained is concentrated, use col-umn chromatography to give purifying, obtain yellow solid (productive rate 77%).
(synthesis of compound 4)
30 milliliters of toluene, 12 ml waters, 0.5 gram of (0.4mmol) Pd (pph is added in the twoport flask of 250 milliliters
3)
4, 3.3 grams of (24mmol) salt of wormwood, 1.5 grams of (12.3mmol) phenyl-boron dihydroxides, 2 grams of (4.7mmol) 3-(the bromo-9H-carbazole of 3,6-bis--9-base) cyanobenzenes, 20 milliliters of (1mmol) P
tbu
3and magnetite, refluxed under nitrogen also stirs 24 hours, after having reacted, extract with methylene dichloride and water, the organic layer obtained is concentrated to obtain solid again, use col-umn chromatography to give purifying, obtain white solid 3-(3,6-phenylbenzene-9H-carbazole-9-base) cyanobenzene (productive rate 69.8%).
In 250 milliliters of twoport flasks, add 60 milliliters of dimethyl formamides, 450 milligrams of (1.07mmol) 3-(3, 6-phenylbenzene-9H-carbazole-9-base) cyanobenzene, 208.71 milligrams of (3.21mmol) sodiumazide, 171.73 milligrams of (3.21mmol) ammonium chlorides and magnetite, constant temperature 100 DEG C reaction 38 hours under a nitrogen, after having reacted, filter after adding 10 milliliter of 10% spirit of salt, and with ethyl acetate and water extraction, organic layer drains to obtain light orange solid 3, 6-phenylbenzene-9-(3-2H-tetrazolium-5-base-phenyl)-9H-carbazole (productive rate 85%).
At 250 milliliters of single port bottles, add 100 milliliters of acetone (acetone), 486 milligrams (1.05mmol) 3,6-phenylbenzene-9-(3-2H-tetrazolium-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, back flow reaction was filtered after 18 hours, with column purified, obtained white solid (productive rate 38%).
(synthesis of compound 5)
At 50 milliliters of single port bottles, add 15 milliliters of toluene, 500 milligrams of (1.17mmol) 3-(3, the bromo-9H-carbazole of 6-bis--9-base) cyanobenzene, 154 milligrams of (0.785mmol) diphenylethan (2-Phenylacetophenone), 0.05 milliliter of (0.94mmol) vitriol oil and magnetites, back flow reaction was filtered after 24 hours, after ethyl acetate and water extraction, concentrating under reduced pressure obtains white solid 3, the bromo-9-3-(4 of 6-bis-, 5-phenylbenzene-1,3-oxazole-2-base) phenyl-9H-carbazole (productive rate 77.8%).
In the twoport flask of 50 milliliters, 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, the bromo-9-3-(4 of 6-bis-, 5-phenylbenzene-1,3-oxazole-2-base) phenyl-9H-carbazole, 0.4 milliliter of (0.02mmol) P
tbu
3and magnetite, refluxed under nitrogen also stirs 24 hours, after having reacted, and extracts with methylene dichloride and water, and the organic layer obtained is concentrated to obtain solid again, uses col-umn chromatography to give purifying, obtains white solid (productive rate 50%).
Propose the application example of multiple different oled device below, units property detection of going forward side by side, these test results can manifest material of the present invention and have prospect.Test result lists in table one.
Element one
Anode: indium tin oxide is arranged at (thickness 120nm) on glass substrate
Hole injection layer: PEDOT (poly-(3,4-ethylenedioxythiophene) (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 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 glass substrate
Hole injection layer: PEDOT (4000rpm)
Hole transmission layer: N, N '-bis-(naphthalene-1-base)-N, N '-bis-(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 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 | Operating voltage (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 use as the hole transmission layer of Organic Light Emitting Diode, the main body of luminescent layer or object or electron transfer layer separately, also can use as hole transmission layer, electron transfer layer and luminescent layer simultaneously, effectively simplify element Making programme.These materials can be used as the light-emitting device possessing indicator elment use, Electrofax, illuminating source, indicating meter, recording light source, read-write light source, signal plate, optics communication means or illumination etc.
Main element nomenclature
10 negative electrode 20 electron injecting layers (EIL)
30 electron transfer layers (ETL) 40 luminescent layer (EML)
50 hole transmission layers (HTL) 60 anode
70 substrates.
Claims (4)
1. a carbazole derivative, has with the structure represented by following formula (1):
In formula (1), R
1~ R
10be selected from hydrogen, C respectively
6~
20aromatic base, C
6~
20fluorinated aromatic base, C
4~
20heterocyclic aromatic base; X
1~ X
2be selected from the arbitrary structure represented by following formula (2) ~ (4),
Wherein, R
11~ R
33be selected from hydrogen, C respectively
6~
20aromatic base, C
6~
20fluorinated aromatic base, C
4~
20heterocyclic aromatic base; X
3be selected from the arbitrary structure represented by following formula (6) ~ (7),
Wherein, R
39~ R
48be selected from hydrogen, C respectively
6~
20aromatic base, C
6~
20fluorinated aromatic base, C
4~
20heterocyclic aromatic base, and R
38be selected from hydrogen, C
1~
4alkyl, C
6~
10aromatic base.
2. carbazole derivative according to claim 1, wherein, X
1, X
2be selected from phenyl, and X
3be selected from 2-methyl isophthalic acid H-tetrazolium-5-base, and there is following chemical formula:
3. carbazole derivative according to claim 1, wherein, X
1, X
2be selected from phenyl, and X
3be selected from 4,5-phenylbenzene-1,3-oxazole-2-base, and there is following chemical formula:
4. an oled device, it is characterized by: between pair of electrodes, include the carbazole derivative any one of claims 1 to 3, this carbazole derivative is used as the hole transmission layer of this oled device, electron transfer layer or luminescent layer main body or guest materials.
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| WO2018237389A1 (en) * | 2017-06-23 | 2018-12-27 | Kyulux Inc. | Composition of matter for use in organic light-emitting diodes |
| US11778904B2 (en) | 2018-05-09 | 2023-10-03 | Kyulux, Inc. | Composition of matter for use in organic light-emitting diodes |
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| 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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