CN1803970A - Organic metal complex and organic electro photoluminescence device comprising the same - Google Patents
Organic metal complex and organic electro photoluminescence device comprising the same Download PDFInfo
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- CN1803970A CN1803970A CN 200510002015 CN200510002015A CN1803970A CN 1803970 A CN1803970 A CN 1803970A CN 200510002015 CN200510002015 CN 200510002015 CN 200510002015 A CN200510002015 A CN 200510002015A CN 1803970 A CN1803970 A CN 1803970A
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Abstract
The provided organic metal complex has structural formula as the right (A1 for substituted or unsubstituted hetero-aromatic ring; A2 for substituted or unsubstituted aromatic ring; A3 for acetylacetone or pyridine-alpha-carboxyl; and X for the group of fluorine, trifluoromethyl, alkoxy, alkylthio and amido). The opposite organic electroluminescence device needs low drive voltage with high efficiency.
Description
Technical field
The present invention relates to a kind of organometallic complex, particularly a kind of organometallic complex that is used for OLED.
Background technology
People such as Pope in 1962 are monocrystalline impressed voltage and luminous with the anthracene, the research of having opened organic electric-excitation luminescent.The people such as Tan of nineteen eighty-two Kodak company make two-layer equation organic film device in the evaporation mode, and it all has significantly improvement on brightness and efficient, and then cause the follow-up research of all circles.Organometallic complex is in the application of OLED, just show up prominently in the field of photoelectrochemistry in the 1980's, having comprised with Pt (II), Ru (II), Os (II), Eu (III) and Ir (III) etc. is the complex compound of central metal, and Ir (III) being most widely used at OLED wherein.
The ruddiness phosphorescence doping complex compound of very early time, as M.E.Thompson and S.R.Forrest at document Nature, 395,1988,151-154 is disclosed, be to be the complex compound PtOEP that central metal forms with Pt, emission wavelength is 650nm, quantum yield is 1.3%, resulting luminous intensity is 0.15lm/W under the current density of 100cd/A, at that time, and the very novel high-level efficiency red light material of can saying so, thereafter M.E.Thompson delivers document in calendar year 2001 again and (consults J.Am.Chem.Soc.2001,123,4304-4312), organic iridium (Iridium) doping object complex compound of many types is disclosed, its emission wavelength has been crossed over ruddiness, green glow and blue light, and delivered in 2003 organic iridium complex the specificity of facial and two kinds of isomers of meridional (consult J.Am.Chem.Soc.2003,125,7377-7387), illustrate that both in efficient and the significant difference on the life-span, have also caused the ardent research of all circles.Relevant organic iridium complex is a lot of in the application of organic light-emitting device, pertinent literature can be consulted United States Patent (USP) and disclose No. 2002024293 in early days, No. 2002034656, No. 2002045061, No. 2003017361, No. 2003092935, No. 2003102800, No. 2004053071, No. 2004102632, No. 2004086743 and No. 2004110031 etc., or No. the 2002226495th, Japanese Patent Laid Open Publication, No. 2002338588, No. 2003109758, No. 2003113246, No. 2003119179, No. 2003123982, No. 2003147021, No. 2003171391, No. 2003206320, No. 2003253128, No. 2003253129, No. 2003253145 and No. 2004111379 etc., and world patent discloses No. 2004026886 in early days, No. 2004028217, No. 2004037836, No. 2004048395 and No. 2004055130 etc.
Organic iridium metals complex compound kind is a lot, as special No. 1434286 of Europe disclose, make a search at a series of organic iridium complexs to the similar dentate of methyl ethyl diketone (acetyl acetone).Organic iridium complex for another United States Patent (USP) is disclosed for No. 2002024293 is the blue phosphorescent material, emission wavelength (λ
Max) approximately greater than 500nm, its external quantum efficiency is greater than 5%.In the doping object of the organic iridium complex of phosphorescence, tangerine light is photochromic to get the brush-off, related compound such as Bt
2Ir (acac), its λ
MaxAbout about 560nm, can consult the pertinent literatures that the people delivered such as Thompson (J.Am.Chem.Soc.2001,123,4304-4312) and for example disclosed in the world patent the 2003040250th, the emission wavelength of its tangerine optical range is about 570nm.
Summary of the invention
The invention provides a kind of organometallic complex, have following chemical formula (I):
n＝0～5 (I)
Wherein A1 comprises replacement or unsubstituted hetero-aromatic ring; A2 comprises and replacing or unsubstituted aromatic nucleus; A3 is acetylacetone based or pyridine-α-carboxylic acid group; And X is selected from the group that fluorine, trifluoromethyl, alkoxyl group, alkylthio and amido are formed.
Organometallic complex provided by the invention, A1 more comprise thienyl, benzene thienyl, furyl or pyridyl.
Organometallic complex provided by the invention, A2 more comprise benzene, benzene thiophene or naphthalene.
Organometallic complex provided by the invention, wherein this complex compound comprises
Wherein
A3 is acetylacetone based or pyridine-α-carboxylic acid group.
Organometallic complex provided by the invention, wherein this complex compound is a luminescent material.
Organometallic complex provided by the invention, wherein this complex compound is an orange phosphorescence filler.
The present invention provides a kind of OLED in addition, and it comprises pair of electrodes, and an organic light emitting medium layer, is arranged between this counter electrode, and wherein this organic light emitting medium layer comprises just like the described organometallic complex of above-mentioned chemical formula (I).
OLED provided by the invention, wherein this organic light emitting medium layer comprises a luminescent layer, and this luminescent layer comprises this organometallic complex.
OLED provided by the invention, wherein this organometallic complex is as tangerine light filler (dopant) material.
OLED provided by the invention, wherein this organic light emitting medium layer more comprises a hole transport layer, a hole blocking layer, an electron transfer layer or a buffer layer.
OLED provided by the invention, wherein the driving voltage of this OLED is between 4.66～5.55 volts.
OLED provided by the invention, wherein the luminosity of this OLED is between 220～400cd/m
2
OLED provided by the invention, wherein this OLED forelock luminance brightness is between 20～45cd/A.
OLED provided by the invention, wherein the luminous efficiency of this OLED is between 12.4～26.1lm/W.
OLED provided by the invention, wherein the purity of color of this OLED is x=0.47～0.50, y=0.49～0.51.
OLED provided by the invention, wherein the emission wavelength of this OLED is between 560～580nm.
The OLED that the present invention makes has low driving voltage, high efficiency element superiority.
Description of drawings
Fig. 1 is the diagrammatic cross-section that shows OLED structure of the present invention.
Embodiment
The invention provides a kind of organometallic complex, have chemical formula (I):
In chemical formula (I), A1 comprises thienyl, benzene thienyl, furyl or pyridyl for replacing or unsubstituted hetero-aromatic ring, is preferably thienyl or benzene thienyl.
A2 comprises benzene, benzene thiophene or naphthalene for replacing or unsubstituted aromatic nucleus.
A3 is acetylacetone based or pyridine-α-carboxylic acid group.
X then comprises fluorine, trifluoromethyl, alkoxyl group, alkylthio or amido.
Below list the particular instance of organometallic complex of the present invention:
In above-claimed cpd, A3 is acetylacetone based or pyridine-α-carboxylic acid group.
Chemical formula (I) can be synthetic by following manner, at first, complies with the dentate compound that general organic synthesis technology synthesizes organometallic complex earlier, for example phenyl thienopyridine, naphthyl thienopyridine or phenyl benzene thienopyridine.Then, mixed ligand based compound, metal halide, solvent and deionized water place reaction flask, and wherein this metal halide for example is hydration iridous chloride (IrCl
3H
2O), solvent for example is cellosolvo (2-ethoxy ethanol), heating reflux reaction 45～50 hours, afterwards, make reaction soln be cooled to room temperature, filter, collect solid, again for example to be the cleaning of water or methanol solvent on a small quantity, dry, obtain the organo-metallic binary, then, mix the organo-metallic binary and be yellow soda ash (Na for example
2CO
3) salt, two tooth auxiliary group and for example place reaction flask for the solvent of cellosolvo, heated and stirred reaction 20～25 hours, wherein this pair tooth auxiliary group for example is acetylacetone based or pyridine-α-carboxylic acid group, afterwards, make reaction soln be cooled to room temperature, filter, collect solid, for example to be that water or methanol solvent are cleaned on a small quantity, drying can obtain by two dentate compounds and the two formed organometallic complex of tooth auxiliary group (chemical formula (I)) again.
The iridium of this d6 family (Ir) metal complex has intensive spin-orbit coupling effect (spin-orbital coupling), makes the transmission of electronics can see through metal-dentate charge transfer MLCT (Metal to Ligand Charge Transfer) and (П-П
*) mixing of dentate, impelling from singlet excited to the ride-through capability between triplet excited state system increases, and having crossed over spin and having prohibited, and strengthens the luminous efficiency of phosphorescence.This phosphorescence radiation wavelength drops on tangerine, yellow range (530～600nm), this has the novel phosphor material of high-luminous-efficiency and low driving voltage characteristic simultaneously, more good than prior art, and use luminescence component that this compound makes in the easier NTSC specification that meets existing TV on the white light backlight, on white-light illuminating and the full-color display.
The present invention provides a kind of OLED in addition, comprises, pair of electrodes, and an organic light emitting medium layer are arranged between this counter electrode, and wherein this organic light emitting medium layer comprises just like the described organometallic complex of above-mentioned chemical formula (1).
Above-mentioned organic light emitting medium layer comprises a luminescent layer, and luminescent layer comprises the organometallic complex as chemical formula (I), wherein organometallic complex is as ruddiness filler (dopant) material, and the material of main part of luminescent layer for example is CBP, TCTA, CzTT, TPBI, TAZ, BAlq, MCP, UGHI, UGH2 or UGH3.The organic light emitting medium layer more comprises a hole transport layer, a hole blocking layer, an electron transfer layer or a buffer layer, wherein the hole-transfer layer material for example is HTM2, TPD, NPB, PPD, TBPB, spiro-TAD, spiro-NPB, TPTE2, TPTE1, NTPA or DNPD, the hole barrier layer material for example is Bphen, BCP, BAlq, CF-X, TAZ or CF-Y, the electric transmission layer material for example is t-Bu-PBD, Alq3, BeBq, TAZ, Almq3, BAlq or TPBI, and cushioning layer material for example is lithium fluoride or Lithium Oxide 98min.The abbreviation of above-mentioned each compound, represent following structural:
Then, the making of OLED of the present invention is described, at first, provide a substrate as anode, then, the evaporation hole transmission layer is on substrate, and the thickness of hole transmission layer is between 400～600 , afterwards, plate guest emitter (guest)-iridium metals complex compound and host emitter as luminescent layer (lightemitting layer) in evaporation mode altogether on hole transport layer, wherein the ratio of guest emitter/host emitter is 5～10% (v/v), and the thickness of luminescent layer is between 150～250 , then, evaporation hole blocking layer on luminescent layer (hole blocker), the thickness of hole blocking layer is between 100～200 , the person of connecing, evaporation electron transfer layer on hole blocking layer, the thickness of electron transfer layer is followed evaporation buffer layer on electron transfer layer (buffer layer) between 100～200 , the thickness of buffer layer is between 3～10 , at last, plate negative electrode on buffer layer, the thickness of negative electrode is between 1000～1400 , so far, promptly finish the making of this OLED.
The driving voltage of this OLED is between 4.66～5.55 volts, and its luminosity is between 220～400cd/m
2, or 20～45cd/A, its luminous efficiency is between 12.4～26.1lm/W, and its purity of color is x=0.47～0.50, y=0.49～0.51, its emission wavelength is between 560～580nm.
Below by several embodiment to illustrate further the features and advantages of the present invention.
Embodiment 1
Synthesizing of compound 1
Synthesis step:
(1) phenyl-thiene-3-yl--ketone (Phenyl-thiophen-3-yl-methanone) (compound 1a) of getting 1 gram mixes 2 of 1.03 grams, 2-dimethoxy-ethamine (2,2-Dimethoxy-ethylamine) and 15 milliliters toluene place single neck bottle of 50 milliliters, be heated to 110 degree Celsius, stir and rise again to room temperature after 12 hours, remove a large amount of toluene 2 with low-pressure distillation, 2-dimethoxy-ethamine (2,2-Dimethoxy-ethylamine), again with the tubing string chromatography (towards extract, ethyl acetate: normal hexane=1: 4) give purifying, get the compound 1b of the yellow liquid of 1.12 grams, productive rate 83%.
(2) the compound 1b that the get 2.75 grams polyphosphoric acids (PPA) that mix 10 grams place single neck bottle of 50 milliliters, be heated to 120 degree Celsius, stir and rise again to room temperature after 6 hours, the water that adds 200 milliliters, and be neutralized to alkalescence with an amount of potassium hydroxide, with 120 milliliters ethyl acetate extraction, dewater with the anhydrous magnesium sulfates of 2 grams, can get the compound 1c of 1.79 gram white solids after concentrating, productive rate 85%.
(3) get the compound 1c of 0.725 gram and the IrCl of 0.57 gram
3H
2O is mixed in the water of 15 milliliters cellosolvo (2-ethoxy ethanol) and 5 milliliters, cooling after refluxing 48 hours with 110 degree Celsius steams solvent in the mode of low-pressure distillation, behind the washing and drying, obtain the compound 1d of 0.743 gram yellow powder shape, productive rate 81%.
(4) mix compound 1d, 1.12 methyl ethyl diketones (aceticacetone) that restrain and 0.59 yellow soda ash that restrains of 1.46 grams in 20 milliliters cellosolvo (2-ethoxy ethanol) solution, heat to 120 degree Celsius, stir cooling after 24 hours, mode with low-pressure distillation steams solvent, behind the washing and drying, promptly obtain the compound 1 of 1.60 gram yellow powder shapes, productive rate 68%.
Embodiment 2
Synthesizing of compound 2
Compound 2
Synthesis step:
(1) phenyl-thiophene-2-base-ketone (Phenyl-thiophen-2-yl-methanone) (compound 2a) of getting 1 gram mixes 2 of 1.03 grams, 2-dimethoxy-ethamine (2,2-Dimethoxy-ethylamine) and 15 milliliters toluene place single neck bottle of 50 milliliters, be heated to 110 degree Celsius, stir and rise again to room temperature after 12 hours, remove a large amount of toluene 2 with low-pressure distillation, 2-dimethoxy-ethamine (2,2-Dimethoxy-ethylamine), again with the tubing string chromatography (towards extract, ethyl acetate: normal hexane=1: 4) give purifying, get the compound 2b of the yellow liquid of 1.09 grams, productive rate 81%.
(2) the compound 2b that the get 2.5 grams polyphosphoric acids (PPA) that mix 9 grams place single neck bottle of 50 milliliters, be heated to 120 degree Celsius, stir and rise again to room temperature after 6 hours, the water that adds 200 milliliters, and be neutralized to alkalescence with an amount of potassium hydroxide, with 120 milliliters ethyl acetate extraction, dewater with the anhydrous magnesium sulfates of 2 grams, can get the compound 2c of 1.53 gram white solids after concentrating, productive rate 80%.
(3) get the compound 2c of 0.80 gram and the IrCl of 0.62 gram
3H
2O is mixed in the water of 15 milliliters cellosolvo (2-ethoxy ethanol) and 5 milliliters, cooling after refluxing 48 hours with 110 degree Celsius steams solvent in the mode of low-pressure distillation, behind the washing and drying, obtain the compound 2d of 0.79 gram yellow powder shape, productive rate 78%.
(4) mix compound 2d, 1.21 methyl ethyl diketones (aceticacetone) that restrain and 0.60 yellow soda ash that restrains of 1.5 grams in 20 milliliters cellosolvo (2-ethoxy ethanol) solution, heat to 120 degree Celsius, stir cooling after 24 hours, mode with low-pressure distillation steams solvent, behind the washing and drying, promptly obtain the compound 2 of 1.43 gram yellow powder shapes, productive rate 61%.
Embodiment 3
The making of OLED
See also Fig. 1, the making of OLED of the present invention is described, at first, one tin indium oxide (ITO is provided, Indium-tin-oxide) substrate 100 of glass is as anode, substrate 100 cleans with commercially available glass cleaner earlier, again with washed with de-ionized water and oven dry, then, evaporation NPB (4 on ito glass substrate 100,4 '-bis[N-(naphthyl)-N-phenyl-amino] biphenyl), as hole transmission layer 110, the thickness of hole transmission layer 110 is 500 , afterwards, on hole transport layer 110, plate guest emitter (guest)-iridium metals complex compound (compound 1) and host emitter (host)-CBP (4 to be total to the evaporation mode, 4 '-N, N '-dicarbazole-biphenyl) as luminescent layer (light emitting layer) 120, wherein the ratio of guest emitter/host emitter is 6% (v/v), the thickness of luminescent layer 120 is 200 , then, evaporation BCP (bathocuproine) on luminescent layer 120, as hole blocking layer (holeblocker) 130, the thickness of hole blocking layer 130 is 150 , the person of connecing, evaporating Al q3 on hole blocking layer 130 (tris (8-hydroxyquinoline) aluminum (III)), as electron transfer layer 140, the thickness of electron transfer layer 140 is 200 , then, and evaporation lithium fluoride on electron transfer layer 140, as buffer layer (bufferlayer) 150, the thickness of buffer layer 150 is 5 , and is last, plated aluminum on buffer layer 150 (Al) metal, as negative electrode 160, the thickness of negative electrode 160 is 1200 , so far, promptly finishes the making of this OLED.
Then, carry out the making of other 3 kinds of OLEDs, because making step and above-mentioned steps are similar, then do not give unnecessary details at this, adulterated guest emitter kind and ratio difference to some extent in the luminescent layer 120 only wherein, for example, making a kind of guest emitter is that compound 2, doping ratio are 6% device, or makes the device that doping ratio is 9%, guest emitter is respectively compound 1 and compound 2.
See also table 1, list the OLED that the present invention utilizes different guest emitter kinds and different doping ratio to be made, it is in the data of driving voltage, luminosity, CIE coordinate and wavelength.
Table 1:
| The doping object | Compound 1 (6%) | Compound 1 (9%) | Compound 2 (6%) | Compound 2 (9%) |
| Driving voltage (volts) | 5.21 | 4.66 | 5.55 | 5.46 |
| Luminosity (cd/m 2) | 399 | 390 | 222 | 288 |
| Luminosity (cd/A) | 40.3 | 38.7 | 21.9 | 28.7 |
| Luminous efficiency (lm/W) | 24.3 | 26.1 | 12.4 | 16.5 |
| CIE coordinate (x, y) value | (0.48，0.50) | (0.49，0.50) | (0.49，0.50) | (0.49，0.50) |
| Wavelength | 560 | 560 | 564 | 564 |
Because listed driving voltage, the luminosity (cd/m of table 1
2) and luminous efficiency (lm/W) data all be measured under the condition of 1mA/cm, therefore, show that the OLED that the present invention makes has low driving voltage, high efficiency element superiority.
Though the present invention with preferred embodiment openly as above, so it is not in order to limit the present invention.Anyly be familiar with this technology person, 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 is as the criterion with claim.
Symbol description:
100～anode;
110～hole transport layer;
120～luminescent layer;
130～hole blocking layer;
140～electron transfer layer;
150～buffer layer;
160～negative electrode.
Claims (16)
1, a kind of organometallic complex is characterized in that having following chemical formula (I):
Wherein
A1 comprises and replacing or unsubstituted hetero-aromatic ring;
A2 comprises and replacing or unsubstituted aromatic nucleus;
A3 is acetylacetone based or pyridine-α-carboxylic acid group; And
X selects from fluorine, trifluoromethyl, alkoxyl group, alkylthio, one of the amino or group that formed.
2, organometallic complex according to claim 1 is characterized in that A1 more comprises thienyl, benzene thienyl, furyl or pyridyl.
3, organometallic complex according to claim 1 is characterized in that A2 more comprises benzene, benzene thiophene or naphthalene.
4, organometallic complex according to claim 1 is characterized in that this complex compound comprises
Or
Wherein
A3 is acetylacetone based or pyridine-α-carboxylic acid group.
5, organometallic complex according to claim 1 is characterized in that this complex compound is a luminescent material.
6,, it is characterized in that this complex compound is an orange phosphorescence filler according to the described organometallic complex of claim 1.
7, a kind of OLED is characterized in that comprising:
Pair of electrodes; And
One organic light emitting medium layer is arranged between this counter electrode, it is characterized in that this organic light emitting medium layer comprises organometallic complex according to claim 1.
8, OLED according to claim 7 it is characterized in that this organic light emitting medium layer comprises a luminescent layer, and this luminescent layer comprises this organometallic complex.
9, OLED according to claim 8 is characterized in that this organometallic complex is as tangerine light filler material.
10, OLED according to claim 7 is characterized in that this organic light emitting medium layer more comprises a hole transport layer, a hole blocking layer, an electron transfer layer or a buffer layer.
11, according to claim 7 a described OLED, the driving voltage that it is characterized in that this OLED is between 4.66～5.55 volts.
12, OLED according to claim 7, the luminosity that it is characterized in that this OLED is between 220～400cd/m
2
13, OLED according to claim 7, the luminosity that it is characterized in that this OLED is between 20～45cd/A.
14, OLED according to claim 7, the luminous efficiency that it is characterized in that this OLED is between 12.4～26.1lm/W.
15, according to claim 7 a described OLED, the purity of color that it is characterized in that this OLED is x=0.47～0.50, y=0.49～0.51.
16, according to claim 7 a described OLED, the emission wavelength that it is characterized in that this OLED is between 560～580nm.
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| CN 200510002015 CN1803970A (en) | 2005-01-12 | 2005-01-12 | Organic metal complex and organic electro photoluminescence device comprising the same |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102911211A (en) * | 2011-08-05 | 2013-02-06 | 财团法人工业技术研究院 | Organometallic compound and organic electroluminescent device comprising the same |
| CN102952162A (en) * | 2011-08-29 | 2013-03-06 | 财团法人工业技术研究院 | Organometallic compound and organic electroluminescence device and composition containing same |
| CN104744517A (en) * | 2013-12-26 | 2015-07-01 | 财团法人工业技术研究院 | Organic metal complex and organic electroluminescent device comprising the same |
| US10164199B2 (en) | 2014-12-03 | 2018-12-25 | Industrial Technology Research Institute | Organic metal compound and organic light-emitting device employing the same |
-
2005
- 2005-01-12 CN CN 200510002015 patent/CN1803970A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102911211A (en) * | 2011-08-05 | 2013-02-06 | 财团法人工业技术研究院 | Organometallic compound and organic electroluminescent device comprising the same |
| CN102911211B (en) * | 2011-08-05 | 2016-01-06 | 财团法人工业技术研究院 | Organometallic compound and organic electroluminescent device comprising the same |
| CN102952162A (en) * | 2011-08-29 | 2013-03-06 | 财团法人工业技术研究院 | Organometallic compound and organic electroluminescence device and composition containing same |
| CN104744517A (en) * | 2013-12-26 | 2015-07-01 | 财团法人工业技术研究院 | Organic metal complex and organic electroluminescent device comprising the same |
| US9893304B2 (en) | 2013-12-26 | 2018-02-13 | Industrial Technology Research Institute | Organic metal complexes and organic electroluminescent devices comprising the same |
| US10164199B2 (en) | 2014-12-03 | 2018-12-25 | Industrial Technology Research Institute | Organic metal compound and organic light-emitting device employing the same |
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