CN105294774A - Red organic electrophosphorescence iridium complex and application thereof in OLED devices - Google Patents
Red organic electrophosphorescence iridium complex and application thereof in OLED devices Download PDFInfo
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- CN105294774A CN105294774A CN201510816504.5A CN201510816504A CN105294774A CN 105294774 A CN105294774 A CN 105294774A CN 201510816504 A CN201510816504 A CN 201510816504A CN 105294774 A CN105294774 A CN 105294774A
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Abstract
The present invention discloses a red organic electrophosphorescence iridium complex and application thereof in OLED devices, the iridium complex as a light emitting layer dopant material may improve the performance of the OLED light-emitting devices, the OLED devices prepared by the iridium complex have good photoelectric properties, and can meet the requirements of panel manufacturers.
Description
Technical field
The present invention relates to technical field of semiconductors, especially relate to a kind of electroluminescent phosphorescence organic iridium complex and as the application of luminescent layer dopant material on Organic Light Emitting Diode.
Background technology
Organic electroluminescent (OLED:OrganicLightEmissionDiodes) device technology both can be used for manufacturing novel display product, also may be used for making novel illumination product, be expected to alternative existing liquid-crystal display and fluorescent lighting, application prospect is very extensive.
Current, OLED technique of display is at smart mobile phone, and the fields such as panel computer obtain application, further also will to large size Application Areas expansions such as TVs.But require to compare with the product application of reality, the luminous efficiency of OLED, the performances such as work-ing life also need further lifting.
OLED luminescent device, just as the structure of sandwich, comprises electrode materials rete, and is clipped in the organic functional material between Different electrodes rete, and various difference in functionality material is mutually superimposed according to purposes and jointly forms OLED luminescent device.As current device, when applying voltage to the two end electrodes of OLED luminescent device, and by positive and negative charge in electric field action organic layer functional materials rete, positive and negative charge is compound in luminescent layer further, namely produces OLED electroluminescent.
High performance research is carried for OLED luminescent device comprise: the driving voltage reducing device, improve the luminous efficiency of device, improve the work-ing life etc. of device.In order to realize the continuous lifting of the performance of OLED, not only needing the innovation from OLED structure and manufacture craft, more needing oled light sulfate ferroelectric functional material constantly study and innovate, formulating out the functional materials of more high-performance OLED.
The people such as the Forrest of Princeton university in 1998 study discovery, use organic luminescent device prepared by general organic materials or employing fluorescence dye doping techniques, due to the quantum mechanics transition rule constraint by spin conservation, its maximum luminous internal quantum efficiency is 25%.They are by phosphorescent coloring octaethylporphyrin platinum dopant in main body luminescent material, and preparing external quantum efficiency is 4%, and internal quantum efficiency reaches the luminescent device of 23%, thus opens the frontier of electrophosphorescence.
Because phosphorescent complexes has very high efficiency and brightness, Phosphorescent title complex has stronger application prospect at organic solid-state lighting field.But, because the phosphorescent complexes reported at present exists comparatively serious T-T annihilation and poor carrier transport ability, such title complex often will could realize high performance electroluminescent within the scope of very low, very narrow doping content, this just requires comparatively harsh device preparation condition, thus the higher cost in causing industrialization to be produced, affect quality and the commercial competition ability of product.
Therefore, for the industry application requiring of current OLED, and the photoelectric characteristic demand of OLED, must select to be more suitable for, there is high performance luminescent layer dopant material, the overall characteristic of the high-level efficiency of device, long lifetime and low voltage could be realized.
With regard to the actual demand of current OLED display lighting industry, the development of current OLED material is also nowhere near, and lags behind the requirement of panel manufacturing concern, and the exploitation as the more high performance organic functional material of material enterprise development seems particularly important.
Summary of the invention
For the problems referred to above that prior art exists, the applicant provides a kind of red organic electrophosphorescenpolymer complex of iridium and the application in OLED thereof.Complex of iridium of the present invention can improve OLED luminescent device performance, and the OLED that the present invention produces has good photoelectric properties, can meet the requirement of panel manufacturing concern.
Technical scheme of the present invention is as follows:
A kind of red organic electrophosphorescenpolymer complex of iridium, the formula of described complex of iridium is as shown in general formula (1):
General formula (1)
In general formula (1), R in metal iridium right side structure
a, R
b, R
cindependently be selected from alkyl, cycloalkyl, assorted alkyl, aralkyl, aryl or heteroaryl;
In general formula (1), metal iridium left side structure is the functional group being formed coordinate bond by C, N element and metal iridium, and described functional group is selected from:
Wherein, R
1~ R
13independently be selected from hydrogen, alkyl, cycloalkyl, assorted alkyl, aralkyl, aryl or heteroaryl.
In described general formula (1), R in metal iridium right side structure
a, R
b, R
cpreferred C respectively
1-6straight or branched alkyl, six-ring alkyl, substituted or unsubstituted phenyl, xenyl, naphthyl or six-membered heterocycle base.
In described general formula (1), R in metal iridium right side structure
a, R
b, R
cpreferable methyl, ethyl, sec.-propyl, the tertiary butyl, cyclohexyl, substituted or unsubstituted phenyl, xenyl, naphthyl, triazinyl or pyridyl respectively.
In described general formula (1), R in metal iridium left side structure
1~ R
13preferred hydrogen, C respectively
1-6straight or branched alkyl.
In described general formula (1), R in metal iridium left side structure
1~ R
13preferable methyl, ethyl, sec.-propyl, the tertiary butyl or cyclohexyl respectively.
In described general formula (1), the structure optimization on the right side of metal iridium:
In described general formula (1), the structure optimization on the left of metal iridium:
The concrete structure formula of described complex of iridium is:
Comprise an electroluminescent device for described complex of iridium, described complex of iridium is as the dopant material of electroluminescent device luminescent layer.
The technique effect that the present invention is useful is:
Red organic electrophosphorescenpolymer complex of iridium of the present invention can be applicable to OLED luminescent device and makes, and good device performance can be obtained, described red organic electrophosphorescenpolymer complex of iridium as OLED luminescent device luminescent layer dopant material use time, the current efficiency of device, power efficiency and external quantum efficiency are all greatly improved; Meanwhile, for promoting clearly device lifetime.Red organic electrophosphorescenpolymer complex of iridium of the present invention has good effect in OLED luminescent device, has good industrialization prospect.
Accompanying drawing explanation
Fig. 1 is the structural representation of the OLED of materials application cited by the present invention;
In figure, 1 is transparent substrate layer, and 2 is ITO, and 3 is hole injection layer, and 4 is hole transmission layer, and 5 is luminescent layer, and 6 is hole barrier/electron transfer layer, and 7 is electron injecting layer, and 8 is negative electrode reflection electrode layer.
The chemical structural formula of material therefor when Fig. 2 is the embodiment of the present invention 27 making devices.
Embodiment
In order to the technique means of the present invention of understanding clearly and practical purpose, by enumerating embodiment and comparative example, being aided with necessary picture simultaneously and being illustrated.
The synthesis of embodiment 1 compd A 1
Chemical reaction route is as follows:
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of bromobenzene (0.02mol), stirs after 1.5 hours, in mixed solution, drip N, N '-DIC (0.02mol), after instillation, stirring reaction, after 2 hours, obtains yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L1 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 2.8 grams (compd A 1), HPLC:96.7%.
Its molecular weight of mass spectroscopy is 803.8 (C
43h
39irN
4).Results of elemental analyses is: C:64.10; H:5.00; N:7.02; (theoretical value is Ir:23.88: C:64.24; H:4.89; N:6.97; Ir:23.90).
The synthesis of embodiment 2 compd A 2
Chemical reaction route is as follows:
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of bromobenzene (0.02mol), stirs after 1.5 hours, in mixed solution, drip N, N '-DIC (0.02mol), after instillation, stirring reaction, after 2 hours, obtains yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L2 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 2.5 grams (compd A 2), HPLC:96.2%.
Its molecular weight of mass spectroscopy is 859.50 (C
47h
47irN
4).Results of elemental analyses is: C:65.30; H:5.65; N:6.70; (theoretical value is Ir:22.35: C:65.63; H:5.51; N:6.51; Ir:22.35).
The synthesis of embodiment 3 compound A-13
Chemical reaction route is as follows:
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of bromobenzene (0.02mol), stirs after 1.5 hours, in mixed solution, drip N, N '-DIC (0.02mol), after instillation, stirring reaction, after 2 hours, obtains yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L3 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 2.6 grams (compound A-13), HPLC:97.5%.
Its molecular weight of mass spectroscopy is 859.10 (C
47h
47irN
4).Results of elemental analyses is: C:65.40; H:5.75; N:6.60; (theoretical value is Ir:22.25: C:65.63; H:5.51; N:6.51; Ir:22.35).
The synthesis of embodiment 4 compd A 4
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of bromobenzene (0.02mol), stirs after 1.5 hours, in mixed solution, drip N, N '-DIC (0.02mol), after instillation, stirring reaction, after 2 hours, obtains yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L4 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 2.76 grams (compd A 4), HPLC:98.1%.
Its molecular weight of mass spectroscopy is 888.20 (C
49h
51irN
4).Results of elemental analyses is: C:66.40; H:5.75; N:6.20; (theoretical value is Ir:21.65: C:66.26; H:5.79; Ir:21.64; N:6.31).
The synthesis of embodiment 5 compound A-45
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of bromobenzene (0.02mol), stirs after 1.5 hours, in mixed solution, drip N, N '-DIC (0.02mol), after instillation, stirring reaction, after 2 hours, obtains yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L5 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 2.52 grams (compound A-45), HPLC:98.4%.
Its molecular weight of mass spectroscopy is 888.10 (C
49h
51irN
4).Results of elemental analyses is: C:66.30; H:5.70; N:6.40; (theoretical value is Ir:21.60: C:66.26; H:5.79; Ir:21.64; N:6.31).
The synthesis of embodiment 6 compd A 6
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of bromobenzene (0.02mol), stirs after 1.5 hours, in mixed solution, drip N, N '-DIC (0.02mol), after instillation, stirring reaction, after 2 hours, obtains yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L6 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 3.01 grams (compd A 6), HPLC:97.4%.
Its molecular weight of mass spectroscopy is 972.0 (C
55h
63irN
4).Results of elemental analyses is: C:67.80; H:6.80; N:5.40; (theoretical value is Ir:20.00: C:67.94; H:6.53; Ir:19.77; N:5.76).
The synthesis of embodiment 7 compd A 9
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of bromobenzene (0.02mol), stirs after 1.5 hours, in mixed solution, drip N, N '-DIC (0.02mol), after instillation, stirring reaction, after 2 hours, obtains yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L9 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 5.0 grams (compd A 9), HPLC:97.3%.
Its molecular weight of mass spectroscopy is 1156.3 (C
68h
91irN
4).Results of elemental analyses is: C:70.3; H:8.02; N:5.00; (theoretical value is Ir:16.68: C:70.61; H:7.93; Ir:16.62; N:4.84).
The synthesis of embodiment 8 compd A 10
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of bromobenzene (0.02mol), stirs after 1.5 hours, in mixed solution, drip N, N '-DIC (0.02mol), after instillation, stirring reaction, after 2 hours, obtains yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L10 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours.Reaction solution is cooled to room temperature, and underpressure distillation is except desolventizing, and thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtains dark red powder 3.5 grams (compd A 10), HPLC:97.4%.
Its molecular weight of mass spectroscopy is 902.5 (C51H
43irN
4).Results of elemental analyses is: C:68; H:4.60; N:6.0; (theoretical value is Ir:21.40: C:67.75; H:4.79; Ir:21.26; N:6.20).
The synthesis of embodiment 9 compd A 12
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of bromobenzene (0.02mol), stirs after 1.5 hours, in mixed solution, drip N, N '-DIC (0.02mol), after instillation, stirring reaction, after 2 hours, obtains yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L12 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 3.5 grams (compd A 12), HPLC:98.2%.
Its molecular weight of mass spectroscopy is 902.5 (C
39h
35irN
4s
2).
Results of elemental analyses is: C:57.60; H:4.60; N:6.90; S:8.0; (theoretical value is Ir:22.90: C:57.40; H:4.32; Ir:23.55; N:6.87; S:7.86).
The synthesis of embodiment 10 compd A 13
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of bromobenzene (0.02mol), stirs after 1.5 hours, in mixed solution, drip N, N '-DIC (0.02mol), after instillation, stirring reaction, after 2 hours, obtains yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L13 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 2.7 grams (compd A 13), HPLC:98.9%.
Its molecular weight of mass spectroscopy is 806.3 (C
41h
37irN
6).Results of elemental analyses is: C:60.8; H:4.60; N:10.6; (theoretical value is Ir:24: C:61.10; H:4.63; Ir:23.85; N:10.43).
The synthesis of embodiment 11 compd A 14
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of bromobenzene (0.02mol), stirs after 1.5 hours, in mixed solution, drip N, N '-DIC (0.02mol), after instillation, stirring reaction, after 2 hours, obtains yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L14 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 2.7 grams (compd A 13), HPLC:97.3%.
Its molecular weight of mass spectroscopy is 958 (C
53h
45irN
6).Results of elemental analyses is: C:66.10; H:4.60; N:9.00; (theoretical value is Ir:20.3: C:66.43; H:4.73; Ir:20.06; N:8.77).
The synthesis of embodiment 12 compd A 15
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of bromobenzene (0.02mol), stirs after 1.5 hours, in mixed solution, drip N, N '-DIC (0.02mol), after instillation, stirring reaction, after 2 hours, obtains yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L15 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 2.9 grams (compd A 15), HPLC:97.0%.
Its molecular weight of mass spectroscopy is 890.3 (C
47h
49irN
6).Results of elemental analyses is: C:63.20; H:5.70; N:9.10; (theoretical value is Ir:22.0: C:63.42; H:5.55; Ir:21.59; N:9.44).
The synthesis of embodiment 13 compd A 16
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) containing M3 (0.02mol), stirring reaction, after 2 hours, obtains yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L1 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 2.4 grams (compd A 16), HPLC:98.4%.
Its molecular weight of mass spectroscopy is 784.10 (C
41h
43irN
4).
Results of elemental analyses is: C:63.0; H:5.70; N:7.0; (theoretical value is Ir:24.3: C:62.81; H:5.53; Ir:24.52; N:7.15).
The synthesis of embodiment 14 compd A 17
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) containing M3 (0.02mol), stirring reaction, after 2 hours, obtains yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L2 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 2.6 grams (compd A 17), HPLC:98.7%.
Its molecular weight of mass spectroscopy is 840.4 (C
45h
51irN
4).Results of elemental analyses is: C:64.0; H:5.80; N:6.9; (theoretical value is Ir:23.2: C:64.33; H:6.12; Ir:22.88; N:6.67).
The synthesis of embodiment 15 compd A 18
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) containing M3 (0.02mol), stirring reaction, after 2 hours, obtains yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L3 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 2.7 grams (compd A 18), HPLC:98.2%.
Its molecular weight of mass spectroscopy is 840.4 (C
45h
51irN
4).Results of elemental analyses is: C:64.0; H:5.80; N:6.9; (theoretical value is Ir:23.2: C:64.33; H:6.12; Ir:22.88; N:6.67).
The synthesis of embodiment 16 compd A 20
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of 3,5-dimethyl bromobenzene (0.02mol), stir after 1.5 hours, in mixed solution, drip N, N-DIC (0.02mol), after instillation, stirring reaction, after 2 hours, obtains yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L2 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 3.5 grams (compd A 20), HPLC:97.0%.
Its molecular weight of mass spectroscopy is 888.30 (C
49h
51irN
4).Results of elemental analyses is: C:66.50; H:5.60; N:6.20; (theoretical value is Ir:21.70: C:66.26; H:5.79; Ir:21.64; N:6.31).
The synthesis of embodiment 17 compd A 21
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of 3,5-dimethyl bromobenzene (0.02mol), stir after 1.5 hours, in mixed solution, drip N, N-DIC (0.02mol), after instillation, stirring reaction, after 2 hours, obtains yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L6 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 3.0 grams (compd A 21), HPLC:97.9%.
Its molecular weight of mass spectroscopy is 888.30 (C
57h
37irN
4).Results of elemental analyses is: C:68.50; H:6.60; N:5.50; (theoretical value is Ir:19.40: C:68.43; H:6.75; Ir:19.21; N:5.60).
The synthesis of embodiment 18 compd A 23
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of M12, stir after 1.5 hours, obtain yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L2 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 3.2 grams (compd A 23), HPLC:98.2%.
Its molecular weight of mass spectroscopy is 916.50 (C
51h
55irN
4).Results of elemental analyses is: C:67.0; H:6.00; N:6.00; (theoretical value is Ir:21.0: C:66.86; H:6.05; Ir:20.98; N:6.11).
The synthesis of embodiment 19 compd A 25
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of M21, stir after 1.5 hours, obtain yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L7 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 4.0 grams (compd A 25), HPLC:98.7%.
Its molecular weight of mass spectroscopy is 1022.50 (C
59h
65irN
4).Results of elemental analyses is: C:69.50; H:6.30; N:5.50; (theoretical value is Ir:18.70: C:69.31; H:6.41; Ir:18.80; N:5.48).
The synthesis of embodiment 20 compd A 27
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of M19, stir after 1.5 hours, obtain yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L3 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 3.4 grams (compd A 27), HPLC:98.0%.
Its molecular weight of mass spectroscopy is 956.0 (C
55h
47irN
4).Results of elemental analyses is: C:69.20; H:5.0; N:6.0; (theoretical value is Ir:19.80: C:69.08; H:4.95; Ir:20.10; N:5.86).
The synthesis of embodiment 21 compound A-13 1
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of M21, stir after 1.5 hours, obtain yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L13 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 2.8 grams (compound A-13 1), HPLC:98.5%.
Its molecular weight of mass spectroscopy is 856.10 (C
45h
39irN
6).Results of elemental analyses is: C:63.20; H:4.70; N:10.0; (theoretical value is Ir:22.10: C:63.14; H:4.59; Ir:22.45; N:9.82).
The synthesis of embodiment 22 compound A-13 5
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of M20, stir after 1.5 hours, obtain yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L2 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 3.1 grams (compound A-13 5), HPLC:98.2%.
Its molecular weight of mass spectroscopy is 968.0 (C
55h
59irN
4).Results of elemental analyses is: C:68.0; H:6.0; N:6.0; (theoretical value is Ir:20: C:68.22; H:6.14; Ir:19.85; N:5.79).
The synthesis of embodiment 23 compound A-13 6
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of M23.Stir after 1.5 hours, obtain yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L1 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 3.0 grams (compound A-13 6), HPLC:98.4%.
Its molecular weight of mass spectroscopy is 805 (C
42h
38irN
5).Results of elemental analyses is: C:62.40; H:5.0; N:8.50; (theoretical value is Ir:24.10: C:62.66; H:4.76; Ir:23.88; N:8.70).
The synthesis of embodiment 24 compound A-13 8
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of M22, stir after 1.5 hours, obtain yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L1 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 3.1 grams (compound A-13 8), HPLC:98.0%.
Its molecular weight of mass spectroscopy is 891.3 (C
46h
48irN
7).Results of elemental analyses is: C:62.20; H:5.10; N:11.20; (theoretical value is Ir:21.50: C:62.0; H:5.43; Ir:21.57; N:11.0).
The synthesis of embodiment 25 compd A 41
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of M12, stir after 1.5 hours, obtain yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L12 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 2.8 grams (compd A 41), HPLC:98.0%.
Its molecular weight of mass spectroscopy is 872 (C
43h
43irN
4s
2).Results of elemental analyses is: C:59.0; H:4.85; N:6.20; S:7.50; (theoretical value is Ir:22.45: C:59.22; H:4.97; Ir:22.04; N:6.42; S:7.35).
The synthesis of embodiment 26 compd A 42
In 100ml four-hole boiling flask, be cooled to-80 DEG C, pass into nitrogen, n-BuLi (0.02mol) is dropwise added to the hexane solution (100ml) of M24, stir after 1.5 hours, obtain yellow solution; Yellow solution is dropped in the tetrahydrofuran solution (100mL) of L13 bridging complex of iridium (0.01mol), after dropwising, be warming up to 60 DEG C, stir 12 hours, reaction solution is cooled to room temperature, underpressure distillation is except desolventizing, thick product ether rinses three times repeatedly, and after then dissolving with methylene dichloride, filtrate crosses neutral alumina pillar, obtain dark red powder 3.4 grams (compd A 42), HPLC:98.0%.
Its molecular weight of mass spectroscopy is 876.40 (C
45h
31irN
8).Results of elemental analyses is: C:61.50; H:3.70; N:12.45; (theoretical value is Ir:22.35: C:61.70; H:3.57; Ir:21.94; N:12.79).
By the following examples 27 and comparative example 1-20 describe in detail the present invention synthesis the effect of complex of iridium in OLED.Described comparative example 1-20 is invention application examples, compared with embodiment 27, the manufacture craft of device is identical, and have employed identical baseplate material and electrode materials, the thickness of electrode materials is also consistent, and difference changes dopant material in luminescent layer in device.
Embodiment 27
Structure shown in Figure 1, makes OLED luminescent device:
Ito transparent electrode (thickness is 150nm) is washed, carries out ultraviolet-ozone washing after namely carrying out neutralizing treatment, pure water, drying successively again with the organic residue removing transparent ITO surface.
Carried out, on the ito anode (i.e. transparent substrate layer 1) after above-mentioned washing, utilizing vacuum deposition apparatus, evaporation thickness is that the HAT-CN (CAS:105598-27-4) of 30nm uses as hole injection layer 2.And then the NPDN of evaporation 50nm thickness, N'-phenylbenzene-N, N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamines, uses as hole transmission layer 3.And then evaporation 110nm thickness TCTA (4,4', 4 "-three (carbazole-9-base) triphenylamine) is as hole transmission layer 4.
After above-mentioned hole mobile material evaporation terminates, make the luminescent layer of OLED luminescent device, its structure comprise OLED luminescent layer 5 use material C BP (4,4'-bis-(9-carbazole) biphenyl) as material of main part, (piq)
2ir (acac) two (1-phenyl-isoquinoline 99.9) (methyl ethyl diketone) is as phosphorescence dopant material, and phosphor material doping ratio is 5% weight ratio, and luminescent layer thickness is 40nm.
After above-mentioned luminescent layer, continuing vacuum evaporation hole barrier/electron transport layer materials is TPBi (1,3,5-tri-(1-phenyl-1H-benzimidazolyl-2 radicals-Ji) benzene), the vacuum evaporation thickness of this material is 30nm, and this layer is hole barrier/electron transfer layer 6.
On hole barrier/electron transfer layer 6, by vacuum deposition apparatus, make lithium fluoride (LiF) layer that thickness is 1nm, this layer is electron injecting layer 7.
On electron injecting layer 7, by vacuum deposition apparatus, make aluminium (Al) layer that thickness is 80nm, this layer is negative electrode reflection electrode layer 8.
In the present embodiment, the structural formula of critical materials used as shown in Figure 2.
After completing OLED luminescent device as described above, with known driving circuit, anode and negative electrode are coupled together, the luminous efficiency of measuring element, the I-E characteristic of luminescent spectrum and device.The performance test data of obtained device is shown in Table 1.
Comparative example 1
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compd A 1 of embodiment 1.The performance test data of obtained device is shown in Table 1.
Comparative example 2
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compd A 2 of embodiment 2.The performance test data of obtained device is shown in Table 1.
Comparative example 3
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compound A-13 of embodiment 3.The performance test data of obtained device is shown in Table 1.
Comparative example 4
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compd A 4 of embodiment 4.The performance test data of obtained device is shown in Table 1.
Comparative example 5
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compound A-45 of embodiment 5.The performance test data of obtained device is shown in Table 1.
Comparative example 6
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compd A 6 of embodiment 6.The performance test data of obtained device is shown in Table 1.
Comparative example 7
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compd A 9 of embodiment 7.The performance test data of obtained device is shown in Table 1.
Comparative example 8
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compd A 10 of embodiment 8.The performance test data of obtained device is shown in Table 1.
Comparative example 9
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compd A 12 of embodiment 9.The performance test data of obtained device is shown in Table 1.
Comparative example 10
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compd A 13 of embodiment 10.The performance test data of obtained device is shown in Table 1.
Comparative example 11
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compd A 14 of embodiment 11.The performance test data of obtained device is shown in Table 1.
Comparative example 12
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compd A 16 of embodiment 13.The performance test data of obtained device is shown in Table 1.
Comparative example 13
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compd A 17 of embodiment 14.The performance test data of obtained device is shown in Table 1.
Comparative example 14
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compd A 18 of embodiment 15.The performance test data of obtained device is shown in Table 1.
Comparative example 15
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compd A 20 of embodiment 16.The performance test data of obtained device is shown in Table 1.
Comparative example 16
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compd A 23 of embodiment 18.The performance test data of obtained device is shown in Table 1.
Comparative example 17
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compd A 25 of embodiment 19.The performance test data of obtained device is shown in Table 1.
Comparative example 18
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compd A 27 of embodiment 20.The performance test data of obtained device is shown in Table 1.
Comparative example 19
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compound A-13 1 of embodiment 21.The performance test data of obtained device is shown in Table 1.
Comparative example 20
This comparative example is compared with embodiment 27, and difference is: in OLED luminescent device, the phosphorescence dopant material of luminescent layer 5 is by (piq)
2ir (acac) becomes the obtained compound A-13 5 of embodiment 21.The performance test data of obtained device is shown in Table 1.
Table 1
| Device code name | Driving voltage | Luminous efficiency (cd/A) | Color | External quantum efficiency (%) | Drive the life-span |
| Embodiment 27 | 1.0 | 1.0 | Red | 1.0 | 1.0 |
| Comparative example 1 | 0.98 | 1.20 | Dark red | 1.4 | 2.5 |
| Comparative example 2 | 1.01 | 1.37 | Red | 1.5 | 2.8 |
| Comparative example 3 | 0.99 | 1.60 | Pale red | 1.55 | 2.7 |
| Comparative example 4 | 1.02 | 1.68 | Red | 1.70 | 2.67 |
| Comparative example 5 | 1.03 | 1.59 | Pale red | 1.65 | 2.54 |
| Comparative example 6 | 0.97 | 1.70 | Pale red | 1.55 | 2.77 |
| Comparative example 7 | 1.03 | 1.74 | Dark red | 1.65 | 2.43 |
| Comparative example 8 | 1.0 | 1.42 | Pale red | 1.54 | 2.80 |
| Comparative example 9 | 0.96 | 1.32 | Red | 1.40 | 2.70 |
[0199]
| Comparative example 10 | 1.02 | 1.40 | Red | 1.44 | 2.43 |
| Comparative example 11 | 1.03 | 1.35 | Red | 1.41 | 2.34 |
| Comparative example 12 | 0.97 | 1.21 | Pale red | 1.35 | 2.49 |
| Comparative example 13 | 1.10 | 1.24 | Pale red | 1.48 | 2.66 |
| Comparative example 14 | 1.04 | 1.33 | Light red | 1.44 | 2.60 |
| Comparative example 15 | 1.15 | 1.40 | Pale red | 1.28 | 2.30 |
| Comparative example 16 | 1.02 | 1.23 | Red | 1.30 | 2.0 |
| Comparative example 17 | 0.99 | 1.19 | Red | 1.33 | 2.40 |
| Comparative example 18 | 1.07 | 1.31 | Dark red | 1.37 | 1.90 |
| Comparative example 19 | 1.08 | 1.08 | Red | 1.19 | 2.0 |
| Comparative example 20 | 0.98 | 1.09 | Red | 1.15 | 1.89 |
Note: device detection performance is using embodiment 27 as reference, and embodiment 27 device property indices is set to 1.0.
As can be seen from the result of table 1, red organic electrophosphorescenpolymer complex of iridium of the present invention can be applicable to OLED luminescent device and makes, and can obtain good device performance; Comparative example 1-20 relative to embodiment 27, the current efficiency of device, power efficiency and external quantum efficiency are all greatly improved; Meanwhile, promote also clearly device lifetime.
From above market demand, red organic electrophosphorescenpolymer complex of iridium of the present invention has good effect in OLED luminescent device, has good industrialization prospect.
Although disclose the present invention by embodiment and preferred implementation, should be understood that and the invention is not restricted to disclosed embodiment.On the contrary, it will be understood by those skilled in the art that it is intended to contain various modification and similar arrangement.Therefore, the scope of claims should be consistent with the widest explanation to contain all such modification and similar arrangement.
Claims (8)
1. a red organic electrophosphorescenpolymer complex of iridium, is characterized in that the formula of described complex of iridium is as shown in general formula (1):
In general formula (1), R in metal iridium right side structure
a, R
b, R
cindependently be selected from alkyl, cycloalkyl, assorted alkyl, aralkyl, aryl or heteroaryl;
In general formula (1), metal iridium left side structure is the functional group being formed coordinate bond by C, N element and metal iridium, and described functional group is selected from:
Wherein, R
1~ R
13independently be selected from hydrogen, alkyl, cycloalkyl, assorted alkyl, aralkyl, aryl or heteroaryl.
2. complex of iridium according to claim 1, is characterized in that in described general formula (1), R in metal iridium right side structure
a, R
b, R
cbe respectively C
1-6straight or branched alkyl, six-ring alkyl, substituted or unsubstituted phenyl, xenyl, naphthyl or six-membered heterocycle base.
3. complex of iridium according to claim 1, is characterized in that in described general formula (1), R in metal iridium right side structure
a, R
b, R
cbe separately methyl, ethyl, sec.-propyl, the tertiary butyl, cyclohexyl, substituted or unsubstituted phenyl, xenyl, naphthyl, triazinyl or pyridyl.
4. complex of iridium according to claim 1, is characterized in that in described general formula (1), R in metal iridium left side structure
1~ R
13be separately hydrogen, C
1-6straight or branched alkyl.
5. complex of iridium according to claim 1, is characterized in that in described general formula (1), R in metal iridium left side structure
1~ R
13be separately methyl, ethyl, sec.-propyl, the tertiary butyl or cyclohexyl.
6. complex of iridium according to claim 1, is characterized in that in described general formula (1), the structure on the right side of metal iridium:
7. complex of iridium according to claim 1, is characterized in that described complex of iridium is:
8. comprise an electroluminescent device for complex of iridium described in any one of claim 1 ~ 7, it is characterized in that the dopant material of described complex of iridium as electroluminescent device luminescent layer.
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