CN1803783A - Halogen atom-containing bidentate ligand, its iridium complex and electrogenerated phosphorescence device - Google Patents
Halogen atom-containing bidentate ligand, its iridium complex and electrogenerated phosphorescence device Download PDFInfo
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- CN1803783A CN1803783A CN 200510020018 CN200510020018A CN1803783A CN 1803783 A CN1803783 A CN 1803783A CN 200510020018 CN200510020018 CN 200510020018 CN 200510020018 A CN200510020018 A CN 200510020018A CN 1803783 A CN1803783 A CN 1803783A
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Abstract
The disclosed bidentate ligand contains halogen atom and bases on 2-phenyl benzothiazole. Wherein, the opposite iridium complex has chemical formula as Ir(C Lambda N)2(acac) with C Lambda N as the ligand here and acac as acetylacetone anion. The opposite electroluminescent device based on the iridium complex comprises: a conductive glass substrate layer, a hole conduction layer, a luminescent layer, an electronic layer, a barrier layer for hole and exciton, and a cathode layer. Compared with prior art, this invention improves the brightness and efficiency of device, can adjust wavelength, and has wide application.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, relate in particular to a kind of heavy metal element complex of iridium luminescent material that contains at least one halogen atom (chlorine, bromine or iodine) based on 2-phenyl benzothiazole part.
Background technology
1987, the C.W.Tang of Kodak (Appl.Phys.Lett.1987,51,913) reported in double-deck organic film structure, with oxine aluminium (Alq
3) be luminescent material, obtain low driving voltage (10V), high brightness (1000cd/m
2), the organic electroluminescence device (OLEDs) of high-level efficiency (1.5lm/w) makes a breakthrough the research of electroluminous organic small molecular device.The development that (Nature, 1990,347,539) such as nineteen ninety J.H.Burroughes adopt the preparation LED marker of PPV success the organic polymer electroluminescent device obtains pioneering achievement.Organic electroluminescent becomes one of the research focus in luminous field gradually.Organic electroluminescent LED becomes one of technology the most competitive in traditional cathode tube and the third generation flat pannel display after the liquid-crystal display.
Common electroluminescent organic material can be divided into organic molecule and organic polymer.According to spin quantum statistical theory, the formation probability proportion of singlet state exciton and triplet exciton is 1: 3, promptly the singlet state exciton only account for " electron-hole pair " 25%.Common fluorescence luminescent material can only utilize singlet state exciton attenuation luminous, and its electroluminescent maximum quantum yield is 25%.But phosphor material can utilize the singlet state exciton, can utilize triplet exciton again, and in theory, the OLED internal quantum efficiency that utilizes phosphorescent coloring to make can reach 100%.These have d with Os, Ru, Pd, Pt, Ir and Au
6The heavy metal atom of feature is the Organometallic complexes at center, because spin orbital coupling, scurries the probability that jumps between being and increases, and the phosphorescence that causes prohibiting can be launched.The atomic transition of these heavy metal atoms itself is not luminous, but the minimum excited state of their energy normally triplet state metal to the energy of part shift (
3MLCT), make phosphorescent lifetime shorten (＜100 μ s) greatly.Scurry the probability that jumps between strong spin orbital coupling makes and is and improve (＞99%) greatly, excited singlet state and triplet state are mixed, the singlet state of compound and triplet exciton can cause phosphorescent emissions like this, obtain very high phosphorescence efficient.Therefore seeking the phosphor material with better brightness and efficient presses for.
Summary of the invention
The object of the present invention is to provide the electronic phosphorescence material of heavy metal complexes of a kind of brightness height, excellent in efficiency, and the part of this heavy metal complex and the electroluminescent device that adopts this heavy metal complex to make as the phosphorescence dopant material.
Heavy metal complex part of the present invention is a bidentate ligand, contains at least one or a plurality of halogen atom, and the ligand structure formula is:
R in the formula
1～R
9One of at least be halogen atom, all the other are hydrogen, and halogen atom is selected from chlorine, bromine and iodine.
Complex of iridium of the present invention, chemical formula are Ir (C^N)
2(acac), C^N represents the bidentate ligand among the present invention, and acac represents the methyl ethyl diketone negatively charged ion.Its structural formula is:
R in the formula
1～R
4, R
6～R
9One of at least be halogen atom, all the other are hydrogen, and halogen atom is selected from chlorine, bromine and iodine.
For example:
When C^N=4-chloro-2-phenyl benzothiazole, structural formula is:
When C^N=4-bromo-2-phenyl benzothiazole, structural formula is:
When C^N=3-bromo-2-phenyl benzothiazole, structural formula is:
When C^N=4-iodo-2-phenyl benzothiazole, structural formula is:
Electroluminescent device of the present invention, comprise glass substrate, attached to the conductive glass layer on the glass substrate, hole transmission layer with the conductive glass layer applying, luminescent layer with the hole transmission layer applying, with the hole and the exciton barrier-layer of luminescent layer applying, with the electronic shell transport layer of hole and exciton barrier-layer applying, with the cathode layer of electronic shell transport layer applying, luminescent layer is made up of material of main part and dopant material, and the dopant material chemical formula is Ir (C^N)
2(acac), doping ratio is 4wt%-10wt%, and material of main part is 4,4 '-N, N '-two carbazoles-biphenyl (CBP).
(C^N) of the present invention bidentate ligand is compared with disclosed part, introduce one or several halogen atom (chlorine, bromine or iodine), bromine atoms particularly, utilize the halogen atom in the bidentate ligand and the phosphorescence reinforcing effect of heavy metal iridium atom simultaneously, the brightness and the efficient of the device that with the heavy metal complex is the luminescent layer making have been improved, and can be by changing substituent position, number and kind, the emission wavelength of adjusting title complex in certain scope.
Heavy metal complex of the present invention has excellent electroluminescent phosphorescence performance, can be used as electromechanical phosphorescent material, is used for the luminescent layer of electro phosphorescent device.
The inventor has found to have higher photoluminescence efficiency, and can produce high efficiency electroluminous heavy metal complex of iridium.Electroluminescent device performance based on these title complexs is best in the device of reporting at present of the same type, is better than disclosed similar adulterated EL part.A kind of maximum brightness of the optical device that turns to be yellow can reach every square metre of 25409 Kan Tela among the present invention, the highest numerical value 2166 Kan Tela than disclosed similar luminescent device improve 11.7 times for every square metre, maximum current efficient can reach every ampere of 36.83 Kan Tela, maximum lumen efficient reaches every watt of 23.47 lumen, and by changing the position of halogen atom in the bidentate ligand, number and kind are regulated emission wavelength within the specific limits, as work as R
1～R
6, R
8～R
9=H, R
7=Br and R
1～R
5, R
7～R
9=H, R
6During=Br, two heavy metal complex emission wavelengths can be regulated 29nm.
Description of drawings
Fig. 1 is an electroluminescent device structural representation of the present invention;
(luminescent material is Ir (4-bbt) to the emmission spectrum of Fig. 2 electroluminescent device of the present invention
2(acac) and Ir (3-bbt)
2(acac), 4-bbt=4-bromo-2-phenyl benzothiazole, 3-bbt=3-bromo-2-phenyl benzothiazole).
Embodiment
The present invention is further illustrated below by specific embodiment, but the protection domain that these specific embodiments do not limit the present invention in any way.
The used raw material of the present embodiment is a known compound, can buy on market, or available methods known in the art is synthetic.
1. part is synthetic:
In the 25ml round-bottomed flask, (1.25 grams 10mmol) with 4-halobenzene formaldehyde/3-bromobenzaldehyde (10mmol), add 20ml methyl-sulphoxide (DMSO), backflow 4h under the argon shield to put into the amino adjacent mercapto fen of 2-.After being chilled to room temperature, reaction solution is poured in a large amount of frozen water, suction filtration, thick product washes with big water gaging, and dehydrated alcohol (18.6ml) recrystallization is used in the vacuum drying oven oven dry then.
4-chloro-2-phenyl benzothiazole (4-cbt), white crystal, yield 80.3%.
1H NMR (CDCl
3, 300MHz) δ [ppm]: 8.03 (t, J=8.4Hz, 3H), 7.89 (d, J=8.1Hz, 1H), 7.48 (q, J=7.2Hz, 3H), 7.38 (t, J=7.5Hz, 1H). and fusing point: 116.0～116.3 ℃. ultimate analysis: theoretical value C
13H
8NClS:C, 63.54; H, 3.28; N, 5.70. experimental value: C, 63.45; H, 3.19; N, 5.64%.Ms(FAB)：m/e，245(M
+)。
4-bromo-2-phenyl benzothiazole (4-bbt): light green crystal, yield 81.5%.
1H NMR (CDCl
3, 300MHz) δ [ppm]: 8.04 (d, J=7.8Hz, 1H), 7.93 (m, 3H), 7.60 (d, J=8.4Hz, 2H), 7.44 (t, J=8.4Hz, 1H), 7.38 (t, J=8.1Hz, 1H). fusing point: 120.9～121.4 ℃.Ultimate analysis: theoretical value C
13H
8NBrS:C, 53.81; H, 2.78; N, 4.83; Experimental value: C, 53.65; H, 2.92; N, 4.96%.Ms(FAB)：m/e，289(M
+).
3-bromo-2-phenyl benzothiazole (3-bbt): green crystal, yield 82.3%.
1H NMR (CDCl
3, 300MHz) δ [ppm]: 8.27 (s, 1H), 8.07 (d, J=8.1Hz, 1H), 7.98 (d, J=7.8Hz, 1H), 7.90 (d, J=7.8Hz, 1H), 7.61 (d, J=7.2Hz, 1H), 7.51 (t, J=7.5Hz, 1H), 7.38 (m, 2H). fusing point: 123.1～124.5 ℃.Ultimate analysis: theoretical value C
13H
8NBrS:C, 53.81; H, 2.78; N, 4.83; Experimental value: C, 53.75; H, 2.89; N, 4.86%.Ms(FAB)：m/e，289(M
+).
4-iodo-2-phenyl benzothiazole (4-ibt), green crystal, yield 83.4%.
1H NMR (CDCl
3, 300MHz) δ [ppm]: 8.04 (t, J=7.8Hz, 3H), 7.90 (d, J=8.1Hz, 1H), 7.48 (m, 3H), 7.39 (t, J=8.1Hz, 1H). fusing point: 134.5～135.2 ℃.Ultimate analysis: theoretical value C
13H
8NIS:C, 46.31; H, 2.39; N, 4.15.Experimental value: C, 46.35; H, 2.56; N, 4.06%.Ms(FAB)：m/e，337(M
+)。
2. complex of iridium is synthetic
(0.289g 1.0mmol) is dissolved in ethylene glycol ethyl ether: in the solution of water (12: 4), add IrCl then with the above-mentioned part that makes
3NH
2O (0.14g, 0.40mmol), argon shield, 120 ℃ are reacted 24h down.Reaction solution is chilled to the room temperature after-filtration, leaches thing water, ethanol, hexane wash successively.After the drying, obtain Cyclometalated iridium chlorine bridge dimer.(0.12g, 0.08mmol), (86mg 0.8mmol) is dissolved in the 5ml ethylene glycol ethyl ether, argon shield, 120 ℃ of following reaction 16h for methyl ethyl diketone (0.18ml) and anhydrous sodium carbonate with this dimer.Filtration washing, crude product are eluent with the methylene dichloride, and silica gel column chromatography separates.
Ir (4-cbt)
2(acac): orange red solid, yield: 89.3%.
1H NMR (CDCl
3, 300MHz) δ [ppm]: 8.02 (d, J=6.9Hz, 2H), 7.91 (d, J=7.2Hz, 2H), 7.58 (d, J=8.1Hz, 2H), 7.45 (m, 4H), 6.88 (d, J=8.1Hz, 2H), 6.31 (s, 2H), 5.13 (s, 1H), 1.76 (s, 6H). ultimate analysis: theoretical value C
31H
21O
2N
2S
2Cl
2Ir:C, 47.69; H, 2.71; N, 3.59.Experimental value: C, 47.85; H, 2.67; N, 3.64%.Ms(FAB)：m/e，781(M
+)。
Ir (4-bbt)
2(acac): orange red solid, yield 87.4%.
1H NMR (CDCl
3, 300MHz) δ [ppm]: 7.91 (d, J=9.3Hz, 2H), 7.82 (d, J=9.0Hz, 2H), 7.40 (m, 6H), 6.96 (d, J=7.2Hz, 4H), 6.38 (s, 2H), 5.03 (s, 1H), 1.68 (s, 6H). ultimate analysis: theoretical value C
31H
21O
2N
2S
2Br
2Ir:C, 42.81; H, 2.43; N, 3.22. experimental value: C, 42.63; H, 2.15; N, 3.01%.Ms(FAB)：m/e，870(M
+)。
Ir (3-bbt)
2(acac): orange red solid, yield 85.6%.
1H NMR (CDCl
3, 300MHz) δ [ppm]: 7.97 (d, J=7.8Hz, 2H), 7.85 (d, J=6.9Hz, 2H), 7.67 (s, 2H), 7.39 (d, J=3.0Hz, 4H), 6.66 (d, J=7.8Hz, 2H), 6.16 (d, J=8.4Hz, 2H), 5.06 (s, 1H), 1.69 (s, 6H). ultimate analysis: theoretical value C
31H
21O
2N
2S
2Br
2Ir:C, 42.81; H, 2.43; N, 3.22.Experimental value: C, 42.68; H, 2.34; N, 3.05%.Ms(FAB)：m/e，870(M
+)。
Ir (4-ibt)
2(acac): orange red solid, yield: 88.6%.
1H NMR (CDCl
3, 300MHz) δ [ppm]: 8.02 (d, J=6.6Hz, 2H), 7.90 (d, J=8.7Hz, 2H), 7.57 (d, J=8.1Hz, 2H), 7.44 (m, 4H), 6.88 (d, J=7.2Hz, 2H), 6.33 (s, 2H), 5.12 (s, 1H), 1.76 (s, 6H). ultimate analysis: theoretical value C
31H
21O
2N
2S
2I2Ir:C, 38.64; H, 2.20; N, 2.91.Experimental value: C, 38.66; H, 2.69; N, 2.84%.Ms(FAB)：m/e，964(M
+)。
3. the making of device
Complex of iridium of the present invention can comprise glass lined bottom 1 as the device of luminescent layer, conductive glass layer (ITO) 2, hole transmission layer (4,4 '-two { N-(1-naphthyl-N-phenyl-amino)-biphenyl }) (NPB) 3, the luminescent layer complex of iridium mixes 4,4 '-N, N '-two carbazoles-biphenyl (CBP) 4, hole and exciton barrier-layer 2,9-dimethyl-4,7-phenylbenzene-1,10-phenanthrolene (BCP) 5, electron transfer layer oxine aluminium (Alq
3) 6, cathode layer lithium fluoride and aluminium 7.
Electroluminescent device can be made by means known in the art, as presses reference (Adv.Mater., 2004,16,432) disclosed method and make.Concrete grammar is: under high vacuum condition, and evaporation ITO/NPB (40nm)/CBP+ complex of iridium (30nm)/BCP (10nm)/AlQ successively on through conductive glass (ITO) substrate that cleans
3(30nm)/LiF (1nm)/Al (100nm).
Make device as Fig. 1 with this method, the structure of the various devices that make is exemplified below:
Device one: ITO/NPB (40nm)/CBP+5wt%Ir (4-bbt)
2(acac) (30nm)/BCP (10nm)/AlQ
3(30nm)/LiF (1nm)/Al (100nm).
Device two: ITO/NPB (40nm)/CBP+5wt%Ir (3-bbt)
2(acac) (30nm)/BCP (10nm)/AlQ
3(30nm)/LiF (1nm)/Al (100nm).
Device three: ITO/NPB (40nm)/CBP+8wt%Ir (3-bbt)
2(acac) (30nm)/BCP (10nm)/AlQ
3(30nm)/LiF (1nm)/Al (100nm).
When measuring element performance and electroluminescent spectrum, the ITO electrode always links to each other with positive pole.Electroluminescent spectrum is to measure (see figure 2) on the CCD spectrograph, and electric current (I)-voltage (V)-brightness (L) data are measured on Keithey 2400Source meter, and proofreaied and correct by silicon photoelectric diode.Luminous efficiency (cd/A) is measured by silicon photoelectric diode, and is proofreaied and correct by JY SPEX CCD3000spectrometer..
The performance data of device sees the following form:
| Device | Maximum brightness cd/m 2 | Maximum current efficient cd/A | The highest luminous efficiency lm/w | Emission wavelength nm | Luminescent spectrum |
| Device one device two devices three document maximums | 10012 23758 25409 2166 | 38.79 20.97 36.83 8.12 | 16.89 6.04 23.47 4.63 | 565 571 574 546 | See that Fig. 2 sees that Fig. 2 sees Fig. 2 |
Prepared device three is compared with data in literature, the maximum brightness of this device can reach every square metre of 25409 Kan Tela, the highest numerical value 2166 Kan Tela than disclosed similar title complex luminescent device improve 11.7 times for every square metre, maximum current efficient can reach every ampere of 36.83 Kan Tela, maximum lumen efficient reaches every watt of 23.47 lumen, and by changing the position of halogen atom in the bidentate ligand, number and kind are regulated the heavy metal complex emission wavelength within the specific limits.For the similar device made from the title complex of chloride and iodine, the emission wavelength of device is respectively 553 and 568nm, and maximum current efficient is respectively every ampere of 16.23 and 20.02 Kan Tela.Therefore, compare with other iridium complex electroluminescent material of the same type and device, the present invention has higher brightness and better electroluminescent efficiency.
Claims (5)
1. the bidentate ligand of a halogen atom-containing, its structure is:
R in the formula
1～R
9One of at least be halogen atom, all the other are hydrogen, and halogen atom is selected from chlorine, bromine and iodine.
2. the complex of iridium of bidentate ligand according to claim 1, its structure is:
R in the formula
1～R
4, R
6～R
9One of at least be halogen atom, all the other are hydrogen, and halogen atom is selected from chlorine, bromine and iodine.
3. electroluminescent device, comprise glass substrate, attached to the conductive glass layer on the glass substrate, hole transmission layer with the conductive glass layer applying, luminescent layer with the hole transmission layer applying, hole and exciton barrier-layer with the luminescent layer applying, electronic shell transport layer with hole and exciton barrier-layer applying, cathode layer with the applying of electronic shell transport layer, luminescent layer is made up of material of main part and dopant material, it is characterized in that: the dopant material of luminescent layer is the complex of iridium of bidentate ligand as claimed in claim 2.
4. electroluminescent device as claimed in claim 3, the doping ratio that it is characterized in that the complex of iridium of bidentate ligand is 4wt%-10wt%.
5. as claim 3 or 4 described electroluminescent devices, it is characterized in that: material of main part is 4,4 '-N, N '-two carbazoles-biphenyl, hole transmission layer are 4,4 '-two { N-(1-naphthyl-N-phenyl-amino)-biphenyl }, hole and exciton barrier-layer are 2,9-dimethyl-4,7-phenylbenzene-1,10-phenanthrolene, electron transfer layer are oxine aluminium.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102311405A (en) * | 2010-07-07 | 2012-01-11 | 三星移动显示器株式会社 | Organic materials and the organic light-emitting device that comprises this organic materials |
| CN103012481A (en) * | 2012-12-24 | 2013-04-03 | 东莞彩显有机发光科技有限公司 | Phosphorescence host material, and preparation method and application thereof |
| CN103497219A (en) * | 2013-10-12 | 2014-01-08 | 北京科技大学 | Red-light iridium complexes and application thereof in organic white or red electroluminescence device |
| CN107112419A (en) * | 2014-11-05 | 2017-08-29 | 学校法人冲绳科学技术大学院大学学园 | Doping engineering hole transmission layer for the device based on perovskite |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4119999A1 (en) * | 1991-04-12 | 1992-10-15 | Merck Patent Gmbh | SUPERTWIST-liquid-crystal display |
| JP5265840B2 (en) * | 2001-03-14 | 2013-08-14 | ザ、トラスティーズ オブ プリンストン ユニバーシティ | Materials and devices for blue phosphorescence based on organic light emitting diodes |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102311405A (en) * | 2010-07-07 | 2012-01-11 | 三星移动显示器株式会社 | Organic materials and the organic light-emitting device that comprises this organic materials |
| CN103012481A (en) * | 2012-12-24 | 2013-04-03 | 东莞彩显有机发光科技有限公司 | Phosphorescence host material, and preparation method and application thereof |
| CN103497219A (en) * | 2013-10-12 | 2014-01-08 | 北京科技大学 | Red-light iridium complexes and application thereof in organic white or red electroluminescence device |
| CN107112419A (en) * | 2014-11-05 | 2017-08-29 | 学校法人冲绳科学技术大学院大学学园 | Doping engineering hole transmission layer for the device based on perovskite |
| CN107112419B (en) * | 2014-11-05 | 2019-07-05 | 学校法人冲绳科学技术大学院大学学园 | The method of opto-electronic device and manufacture opto-electronic device |
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