CN1587268A - Anthracene compound and organic electroluminescent device containing anthracene compound - Google Patents
Anthracene compound and organic electroluminescent device containing anthracene compound Download PDFInfo
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- CN1587268A CN1587268A CN 200410071698 CN200410071698A CN1587268A CN 1587268 A CN1587268 A CN 1587268A CN 200410071698 CN200410071698 CN 200410071698 CN 200410071698 A CN200410071698 A CN 200410071698A CN 1587268 A CN1587268 A CN 1587268A
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Abstract
The present invention relates to one kind one anthracene compound with two silyl phenyls and the anthracene compound has photoluminescent property and may be used in organic electroluminescent device.
Description
Technical field
Relevant a kind of anthracene (anthracene) compound of the present invention, relevant especially a kind of anthracene compound with two silicon phenyl, it can be used as the luminescent material of Organnic electroluminescent device.
Background technology
Organnic electroluminescent device (organic electroluminescent device) also is called Organic Light Emitting Diode (organic light-emitting diode; OLED), be with a kind of photodiode (LED) of organic layer as active layers.Because Organnic electroluminescent device has advantages such as low voltage operating, high brightness, in light weight, wide viewing angle and high correlative value, is used in gradually in recent years on the flat panel display (flatpanel display).
Generally speaking, OLED comprises pair of electrodes, and the luminescent layer between electrode.Luminous is because following phenomenon: when electric field put on two electrodes, negative electrode penetrated electronics to luminescent layer, and anode penetrates the hole to luminescent layer.When electronics combined in luminescent layer with the hole, the energy rank were transferred to valence link and can be with (valence bond band), they are given off energy, and send fluorescence (fluorescent light).
Anthracene compound (anthracene) has been used as the material of hole transmission layer and luminescent layer.For example, United States Patent (USP) the 6th, 465 discloses a kind of organic anthracene material as hole transmission layer in No. 115, has following chemical formula:
Its R
1, R
2, R
3, and R
4Each is hydrogen independently, has the alkyl of 1 to 24 carbon, has the aromatic base of 5 to 20 carbon or the aromatic base of replacement, assorted aromatic base, fluorine, chlorine, bromine or the cyano group that has the assorted aromatic base of 5 to 24 carbon or replacement is arranged are arranged.
At United States Patent (USP) the 6th, 534, disclose a kind of luminous anthracene compound in No. 199, have the molecular moiety of three aromatic perfume amines, wherein can be and have following chemical formula:
At United States Patent (USP) the 6th, 310, disclose a kind of luminous aromatic base silicon compound in No. 231, wherein can be and have following chemical formula:
But the anthracene compound for different structure still has demand, in the hope of promoting luminous efficiency.
Summary of the invention
The invention provides a kind of anthracene compound, have chemical formula (I)
Wherein, each R
1And R
2Can be identical or inequality, independently for hydrogen, the aromatic base with 6 to 20 carbon atoms that replaces or do not have replacement is arranged, have and replace or do not have the assorted aromatic base with 2 to 5 carbon atoms of replacement or the alkyl with 1 to 12 carbon atom that replaces or do not have replacement, each R are arranged
3Can be identically or inequality, replace or do not have the aromatic base with 6 to 20 carbon atoms of replacement or the alkyl with 1 to 12 carbon atom that replaces or do not have replacement is arranged for having independently, wherein this substituting group is C
1-10Alkyl, C
1-10Alkoxyl group, phenyl or halogen.
The present invention provides a kind of Organnic electroluminescent device again, and it comprises pair of electrodes, and the organic light emitting medium layer between this counter electrode, and wherein this organic light emitting medium layer comprises as above-mentioned anthracene compound.
Of the present invention being characterized as according in the anthracene compound of the present invention, respectively has a silica-based phenyl as substituting group on 9 and 10 positions of anthracene nucleus, can have substituting group on the silicon.
In more detail, have chemical formula (I) according to anthracene compound of the present invention:
In the chemical formula (I), R
1And R
2Can be identical or differently, can be hydrogen, the aromatic base with 6 to 20 carbon atoms that replaces or do not have replacement is arranged, have and replace or do not have the assorted aromatic base with 2 to 5 carbon atoms of replacement or the alkyl with 1 to 12 carbon atom that replaces or do not have replacement is arranged.Wherein be preferably hydrogen, the aromatic base with 6 to 10 carbon atoms that replaces or do not have replacement is arranged, have and replace or do not have the assorted aromatic base with 4 to 5 carbon atoms of replacement or the alkyl with 1 to 4 carbon atom that replaces or do not have replacement is arranged.
In the chemical formula (I), each R
3Can be identical or differently, replace or do not have the aromatic base with 6 to 20 carbon atoms of replacement or the alkyl with 1 to 12 carbon atom that replaces or do not have replacement is arranged for having independently.Wherein be preferably and replace or do not have the aromatic base with 6 to 10 carbon atoms of replacement or the alkyl with 1 to 3 carbon atom that replaces or do not have replacement is arranged.
For each R in chemical formula (I) compound
1, R
2, and R
3There is the object lesson that replaces or do not have the aromatic base with 6 to 20 carbon atoms of replacement to include but not limited to phenyl (phenyl), 2-aminomethyl phenyl, 3-aminomethyl phenyl, 4-aminomethyl phenyl, 4-ethylphenyl, xenyl (biphenyl), 4-methyl biphenyl, 4-ethyl biphenyl base, 4-cyclohexyl biphenyl base, terphenylyl (terphenyl), 3,5-dichlorophenyl, naphthyl (naphthyl), 5-methyl naphthyl, anthryl (anthryl) and pyrenyl (pyrenyl).
For each R in chemical formula (I) compound
1, R
2, and R
3, have the object lesson that replaces or do not have the alkyl with 1 to 12 carbon atom of replacement to include but not limited to methyl, ethyl, propyl group, butyl, the second month in a season-butyl, tert-butyl, amyl group, hexyl, heptyl, octyl group, 2-propyloxy phenyl base (2-phenylisopropyl), trichloromethyl and trifluoromethyl.
For each R in chemical formula (I) compound
1And R
2, have the object lesson that replaces or do not have the assorted aromatic base with 2 to 5 carbon atoms of replacement to include but not limited to furyl (furanyl), thienyl (thiophenyl), pyrryl (pyrrolyl), pyranyl (pyranyl), thiapyran base (thiopyranyl), pyridyl (pyridinyl), thiazolyl (thiazolyl), imidazolyl (imidazolyl), pyrimidyl (pyrimidinyl) and triazinyl (triazinyl).
Above-mentioned R
1, R
2, and R
3The substituting group that has for example can be: C
1-10Alkyl, C
1-10Alkoxyl group, phenyl or halogen.
List particular instance down according to anthracene compound of the present invention:
Anthracene compound of the present invention can be luminous, is blue light-emitting in several object lessons particularly, or can be as blue light parent (host) material.This kind luminescent material novelty belongs to higher photoluminescence efficiency person in the blue light material.For example in specific embodiments of the invention, therefore luminous efficiency, can advantageously be applied in the Organnic electroluminescent device up to 3.2 candle light/amperes (cd/A).Moreover according to anthracene compound of the present invention, it has two silica-based phenyl, owing to introduce siliceous substituting group, the molecular moiety that has silane on the structure, therefore except as the luminescent material, also can be as electron transport material in the Organnic electroluminescent device or hole mobile material.
Description of drawings
Fig. 1 shows compound (1) and photoluminescence (PL) intensity map of compound (2) under different wave length.
Embodiment
Below by several embodiment to illustrate further the features and advantages of the present invention.Synthesizing of preparation embodiment 1 intermediate product (2)
Route of synthesis is as follows:
Intermediate product (1) intermediate product (2)
With 1, (5.7g 24mmol) is dissolved in the tetrahydrofuran (THF) (THF) of 100mL the 3-dibromobenzene, and (n-BuLi, 21mmol 2.3M) slowly add in the solution under-78 ℃ with the 9.2mL n-Butyl Lithium.After 30 minutes, (2g 9.6mmol) dropwise adds in the said mixture under-78 ℃ will to be dissolved in the anthraquinone of 30mL THF.Make mixture be back to room temperature, stirred then 24 hours.Add cold water (100mL), separate organic phase.With water with ethyl acetate extraction.Organic phase is with MgSO
4Drying is removed with rotary evaporator then and is desolvated, and obtains intermediate product (1) crude product.With KI (4.7g, 29mmol), sodium hypophosphite monohydrate (sodium hypophosphite monohydrate) (6.8g, 58mmol) and 50mL acetic acid add in the crude product.Heated mixt is to reflux 2 hours.After the cooling, collect white precipitate,, obtain intermediate product (2) (4.5g) then with column chromatography purification.
Synthesizing of embodiment 1 compound (1)
Route of synthesis is as follows:
Compound (1)
(27mmol, (6g is 12.3mmol) in the solution of the anhydrous THF of 150mL 2.4M) slowly to add intermediate product (2) under-78 ℃ with the 11.3mL n-Butyl Lithium.After 30 minutes, (8g 27.1mmol) slowly adds in the said mixture will to be dissolved in the silica-based chlorine of triphen (triphenylsilyl chloride) of the anhydrous THF of 20mL.Make mixture be back to room temperature, stirred then 16 hours.Add cold water (100mL), the filtering precipitation then with 30mL ethanol and 30mL hexane wash filter cake, obtains solid product.Further, obtain the compound (1) of 4.0g with the method purifying of distillation.
Analysis of data:
1H?NMR(400MHz，CDCl
3)：δ7.3～7.5(m，23H)，7.5～7.7(m，15H)，7.7～7.84(m，8H)
FAB-MS：m/e＝847(M+)
The preparation of embodiment 2 compounds (2)
Identical with the method for embodiment 1, but use 1, the 4-dibromobenzene replaces 1, and the 3-dibromobenzene makes intermediate product, and further makes compound (2).
Compound (2)
Fig. 1 is presented under the different wave length, and the photoluminescence (photoluminescent) of compound (1) and (2) is the figure of intensity (PL).Its wavelength that shows the maximum strength of compound (1) and (2) is about 420nm, the expression blue light-emitting.
The preparation of embodiment 3 Organnic electroluminescent devices
Use mild detergent, acetone, and ethanol clean with sonic oscillation the glass baseplate that 750nm is thick with ito transparent electrode (anode).With nitrogen base material is dried up, further with the UV/ ozone clean, in 10
-4Deposit under the pressure of Pa.At first with sedimentation rate 0.1nm/sec with 2T-NATA (4,4 ', 4 " three (N-(2-naphthyl)-N-phenyl amido)-triphenylamines) be deposited on the ito transparent electrode, thickness is 600nm, forms hole injection layer.Then, evaporation is to hole injection layer with NPB (N, N '-two (naphthalene-1-yl)-N, N '-phenylbenzene-p-diaminodiphenyl) with sedimentation rate 0.1nm/sec, and thickness is 30nm, forms hole transmission layer.
Keep vacuum, with the TBPe (2 of sedimentation rate 0.1nm/sec with different source of sediment, 5,8,11-four uncle Ding Ji perylenes) (2,5,8,11-Tetra-tert-butyl-perylene) and the compound of specific embodiments of the invention (1) codeposition on hole transmission layer, thickness is 30nm, weight ratio is 2.5: 100, forms luminescent layer.Afterwards, with sedimentation rate 0.1nm/sec Alq3 (three (oxine) aluminium salt) is deposited on the luminescent layer of gained, thickness is 30nm, forms electronics injection/transport layer.Then, be respectively 1nm and 100nm with sedimentation rate 1nm/sec deposition LiF and Al to thickness on electronics injection/transport layer, the formation anode makes Organnic electroluminescent device.
Use current density 24mA/cm
2The Organnic electroluminescent device of direct current by above-mentioned gained, record 770cd/m
2And the blue-light-emitting of CIE (1931)=(0.15,0.18), maximum luminous efficiency is 3.2cd/A.
Though the present invention discloses as above with preferred embodiment, so it is not in order to limit the present invention.Any those skilled in the art, without departing from the spirit and scope of the present invention, when doing a little change and retouching.Therefore protection scope of the present invention should be according to appended claim.
Claims (12)
1. an anthracene compound has chemical formula (I)
Wherein, each R
1And R
2Independently for hydrogen, the aromatic base with 6 to 20 carbon atoms that replaces or do not have replacement is arranged, have and replace or do not have the assorted aromatic base with 2 to 5 carbon atoms of replacement or the alkyl with 1 to 12 carbon atom that replaces or do not have replacement, each R are arranged
3For replacement being arranged or not having the aromatic base with 6 to 20 carbon atoms of replacement or the alkyl with 1 to 12 carbon atom that replaces or do not have replacement is arranged, wherein this substituting group is C independently
1-10Alkyl, C
1-10Alkoxyl group, phenyl or halogen.
2. anthracene compound as claimed in claim 1, wherein R
3Be phenyl.
3. anthracene compound as claimed in claim 1, wherein R
3Be methyl.
4. anthracene compound as claimed in claim 1, it has one of following chemical formula:
5. anthracene compound as claimed in claim 1 is a luminescent material.
6. anthracene compound as claimed in claim 1 is the blue light fertile material.
7. Organnic electroluminescent device, it comprises pair of electrodes, and the organic light emitting medium layer between this counter electrode, wherein this organic light emitting medium layer comprises anthracene compound, has chemical formula (I)
Wherein, each R
1And R
2Independently for hydrogen, the aromatic base with 6 to 20 carbon atoms that replaces or do not have replacement is arranged, have and replace or do not have the assorted aromatic base with 2 to 5 carbon atoms of replacement or the alkyl with 1 to 12 carbon atom that replaces or do not have replacement, each R are arranged
3For replacement being arranged or not having the aromatic base with 6 to 20 carbon atoms of replacement or the alkyl with 1 to 12 carbon atom that replaces or do not have replacement is arranged, wherein this substituting group is C independently
1-10Alkyl, C
1-10Alkoxyl group, phenyl or halogen.
8. Organnic electroluminescent device as claimed in claim 7, wherein this R
3Be phenyl.
9. Organnic electroluminescent device as claimed in claim 7, wherein this R
3Be methyl.
10. Organnic electroluminescent device as claimed in claim 7, wherein this anthracene compound has one of following chemical formula:
11. Organnic electroluminescent device as claimed in claim 7, wherein this organic light emitting medium layer comprises luminescent layer, and this luminescent layer comprises anthracene compound, and it has chemical formula (I).
12. Organnic electroluminescent device as claimed in claim 7, wherein this organic light emitting medium layer comprises luminescent layer, and this luminescent layer comprises anthracene compound, and it has chemical formula (I), as the blue light fertile material.
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| CN 200410071698 CN1587268A (en) | 2004-07-21 | 2004-07-21 | Anthracene compound and organic electroluminescent device containing anthracene compound |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006332668A (en) * | 2005-05-26 | 2006-12-07 | Au Optronics Corp | Organic electroluminescent element |
| CN100358904C (en) * | 2005-10-12 | 2008-01-02 | 友达光电股份有限公司 | Spiro silane compound, and organic electroluminescent display device using it |
| CN107805494A (en) * | 2017-10-27 | 2018-03-16 | 广州工程技术职业学院 | One kind is by acetylene bridging fluorenes and anthracene derivant blue light material and preparation method |
| WO2018186462A1 (en) * | 2017-04-07 | 2018-10-11 | コニカミノルタ株式会社 | Fluorescent compound, organic material composition, light emitting film, organic electroluminescent element material, and organic electroluminescent element |
-
2004
- 2004-07-21 CN CN 200410071698 patent/CN1587268A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006332668A (en) * | 2005-05-26 | 2006-12-07 | Au Optronics Corp | Organic electroluminescent element |
| US7479330B2 (en) | 2005-05-26 | 2009-01-20 | Au Optronics Corporation | Anthracene derivatives for organic electroluminescent device |
| CN100358904C (en) * | 2005-10-12 | 2008-01-02 | 友达光电股份有限公司 | Spiro silane compound, and organic electroluminescent display device using it |
| WO2018186462A1 (en) * | 2017-04-07 | 2018-10-11 | コニカミノルタ株式会社 | Fluorescent compound, organic material composition, light emitting film, organic electroluminescent element material, and organic electroluminescent element |
| JPWO2018186462A1 (en) * | 2017-04-07 | 2020-02-27 | コニカミノルタ株式会社 | Fluorescent compound, organic material composition, luminescent film, organic electroluminescent device material, and organic electroluminescent device |
| CN107805494A (en) * | 2017-10-27 | 2018-03-16 | 广州工程技术职业学院 | One kind is by acetylene bridging fluorenes and anthracene derivant blue light material and preparation method |
| CN107805494B (en) * | 2017-10-27 | 2020-03-17 | 广州工程技术职业学院 | Acetylene-bridged fluorene and anthracene derivative blue light material and preparation method thereof |
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