CN102190627A - 9,10-phenanthroimidazole derivatives and use thereof as electroluminescent materials - Google Patents

9,10-phenanthroimidazole derivatives and use thereof as electroluminescent materials Download PDF

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CN102190627A
CN102190627A CN 201010581452 CN201010581452A CN102190627A CN 102190627 A CN102190627 A CN 102190627A CN 201010581452 CN201010581452 CN 201010581452 CN 201010581452 A CN201010581452 A CN 201010581452A CN 102190627 A CN102190627 A CN 102190627A
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phenyl
naphthyl
thienyl
carbazyl
tetraphenyl
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马於光
路萍
王志明
高曌
李维军
刘贺
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Jilin University
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Jilin University
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Abstract

The invention discloses 9,10-phenanthroimidazole derivatives and use thereof as electroluminescent materials, and belongs to the technical field of organic electroluminescence. The luminescent materials have the structural general formula as the description. A core group is 9,10-phenanthro4,5-1,3imidazole or derivatives; substituent groups R0-R8 are respectively selected from hydrogen, alkyl, hydroxyl, alkoxy, nitro, cyan, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthyl, furyl, thienyl, pyrryl, pyridyl, pyranyl, quinolyl, indolyl, carbazolyl and aniline. The organic electroluminescent materials can be applied to luminous layers or carrier transmission layers in multi-layer organic electroluminescent devices.

Description

9,10-phenanthro-imdazole derivatives and as the application of electroluminescent material
Technical field
The invention belongs to technical field of organic electroluminescence, be specifically related to the novel luminous organic material of a class, this type of material can be used for flat-panel display device, photodiode and electronic imaging device.
Background technology
Now, along with the arriving of Development of Multimedia Technology and information society, more and more higher to the flat pannel display performance demands.Emerging in recent years three kinds of technique of display: plasma display, Field Emission Display and display of organic electroluminescence (OLED) have all remedied the deficiency of cathode tube and liquid-crystal display to a certain extent.Wherein, a series of advantages such as the organic film El element has from main light emission, low voltage direct drive, solidifies entirely, the visual angle is wide, color is abundant, compare with liquid-crystal display, OLED does not need backlight, and the visual angle is big, and power is low, its response speed reaches 1000 times of liquid-crystal display, its manufacturing cost but is lower than the LCD product of equal resolving power, and therefore, display of organic electroluminescence certainly will have broad application prospects.The typical structure of OLED comprises cathode layer, anode layer, and the organic luminous layer between this is two-layer, can comprise one or more functional layers in electron transfer layer, hole transmission layer and the luminescent layer in the organic luminous layer.
The luminescent material that adopts functional perfect in shape and function is the important foundation of this type of OLED device of preparation.The patent No. is 4,539,507, United States Patent (USP) in mentioned material with small organic molecule as luminescent material, but small molecule material has a lot of shortcomings, and is bad as film forming properties, and easily crystallization etc.Begin one's study in recent years and use polymkeric substance, but the luminous efficiency of general polymerization thing is lower than small molecule material as luminous organic material.So, seek and a kind ofly have higher photoluminescence efficiency, and in film process, be difficult for the key issue that the crystalline material becomes the technical field of OLED material.
Found that now glyoxaline compound, particularly aromatics imdazole derivatives are the compounds that a class relatively is suitable as electroluminescent organic material.The patent No. is 5,646, the compound that relates to a kind of imidazoles in 948 the United States Patent (USP), this compound couples together three benzoglyoxaline groups by phenyl group, whole material has showed good film-forming properties and high thermodynamic stability, particularly You Yi electronics injection efficiency makes it become most widely used now electron injecting layer material and luminous fertile material.
Summary of the invention
Purpose of the present invention proposes the novel fluorescent material of a class, have the good hole and the function of injecting of electronics simultaneously, can be directly as multi-functional luminescent material, also can be used as and inject transmission class material or fertile material, can be thereby expanded for the kind of the organic compound for preparing the organic luminescent device use.
A class electroluminescent organic material provided by the invention, this material is 9, and the derivative of 10-phenanthro-imidazoles is characterized in that, and this luminescent material has following general structure:
Figure BDA0000037275220000021
In the said structure, the core group is a 9.10-phenanthro-4,5-1,3 imidazoles or derivatives thereofs (being called for short the phenanthro-imidazoles), substituent R 0～R 8Be selected from respectively in hydrogen, alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthyl, furyl, thienyl, pyrryl, pyridyl, pyranyl, quinolyl, indyl, carbazyl or the anilino a kind of (further, wherein the carbonatoms of alkyl or alkoxyl group is 1～12), n is 1～4.X has been the direction group (being that X links to each other with No. 2 positions of imidazoles group) of link effect, the X group is a phenyl, xenyl and methyl biphenyl, triphenyl substituted benzene and methyl triphenyl substituted benzene, tetraphenyl and methyl tetraphenyl substituted benzene, pentapheneyl, hexaphenyl, also can be selected from carbazyl and carbazyl derivative, triphen amido and triphenylamine radical derivative, silica-based and the tetraphenyl-silicon radical derivative of tetraphenyl, anthryl and anthryl derivative, naphthyl and naphthyl derivatives, Spirofluorene-based and Spirofluorene-based derivative, tetraphenyl vinyl and tetraphenyl ethenyl derivatives, thienyl and thienyl derivative, other aromatic structures such as rope sieve cyclic group and rope Luo Huan radical derivative.
The structural formula of X is as follows:
Figure BDA0000037275220000031
The structural formula of the preferred typical compound of the present invention is following I-IV type:
Figure BDA0000037275220000032
Figure BDA0000037275220000033
(annotate: be convenient statement, R0 adopts phenyl as substituting group more in the following preferred structure, can also select other groups).
Concrete building-up process:
(with aniline is example with an amount of phenanthrenequione, aromatic aldehyde, aromatic amine, also can select other amine structures) and ammonium acetate in an amount of acetic acid, be heated near boiling point, after stirring for some time, stop heating, be cooled to the room temperature after-filtration, adopt the post partition method to purify and obtain target product, productive rate＞60%.
Further, the present invention proposes a class electroluminescent organic material, and wherein X is a phenyl, R 1, R 4, R 5, R 8Be H, R 2, R 7, R 3And R 6For in hydrogen, alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthyl, furyl, thienyl, pyrryl, pyridyl, pyranyl, quinolyl, indyl, carbazyl or the anilino a kind of (further, wherein the carbonatoms of alkyl or alkoxyl group is 1～12), n=1～4; The structural formula of further preferred compound is as follows again:
Further, the present invention proposes a class electroluminescent organic material, and wherein X is xenyl or methyl biphenyl, R 1, R 4, R 5, R 8Be H, R 2, R 7, R 3And R 6For in hydrogen, alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthyl, furyl, thienyl, pyrryl, pyridyl, pyranyl, quinolyl, indyl, carbazyl or the anilino a kind of (further, wherein the carbonatoms of alkyl or alkoxyl group is 1～12), n=1～4; The structural formula of further preferred compound is as follows again:
Xenyl is nuclear:
Figure BDA0000037275220000051
Methyl biphenyl is nuclear:
Figure BDA0000037275220000052
Further, the present invention proposes a class electroluminescent organic material, and wherein X is triphenyl substituted benzene and methyl triphenyl substituted benzene, tetraphenyl and methyl tetraphenyl substituted benzene, R 1, R 4, R 5, R 8Be H, R 2, R 7, R 3And R 6For in hydrogen, alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthyl, furyl, thienyl, pyrryl, pyridyl, pyranyl, quinolyl, indyl, carbazyl or the anilino a kind of (further, wherein the carbonatoms of alkyl or alkoxyl group is 1～12), n=1～4; The structural formula of further preferred compound is as follows again:
Figure BDA0000037275220000061
Further, the present invention proposes a class electroluminescent organic material, and wherein X is triphen amido and methyl triphen amido or contains naphthalene triphen amido, wherein R 1, R 4, R 5, R 8Be H, R 2, R 7, R 3And R 6For in hydrogen, alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthyl, furyl, thienyl, pyrryl, pyridyl, pyranyl, quinolyl, indyl, carbazyl or the anilino a kind of (further, wherein the carbonatoms of alkyl or alkoxyl group is 1～12), n=1～4; The structural formula of further preferred compound is as follows again:
Figure BDA0000037275220000071
Further, the present invention proposes a class electroluminescent organic material, and wherein X is carbazyl, phenyl carbazole base or naphthyl carbazole base, R 1, R 4, R 5, R 8Be H, R 2, R 7, R 3And R 6For in hydrogen, alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthyl, furyl, thienyl, pyrryl, pyridyl, pyranyl, quinolyl, indyl, carbazyl or the anilino a kind of (further, wherein the carbonatoms of alkyl or alkoxyl group is 1～12), n=1～4; The structural formula of further preferred compound is as follows again:
Figure BDA0000037275220000072
Further, the present invention proposes a class electroluminescent organic material, and wherein X is that tetraphenyl is silica-based and the methyl tetraphenyl is silica-based, R 1, R 4, R 5, R 8Be H, R 2, R 7, R 3And R 6For in hydrogen, alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthyl, furyl, thienyl, pyrryl, pyridyl, pyranyl, quinolyl, indyl, carbazyl or the anilino a kind of (further, wherein the carbonatoms of alkyl or alkoxyl group is 1～12), n=1～4; The structural formula of further preferred compound is as follows again:
Figure BDA0000037275220000081
Further, the present invention proposes a class electroluminescent organic material, and wherein X is that anthryl, phenyl replace anthryl, naphthyl, phenyl substituted naphthyl, Spirofluorene-based, tetraphenyl vinyl, thienyl or rope sieve cyclic group, R 1, R 4, R 5, R 8Be H, R 2, R 7, R 3And R 6For in hydrogen, alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthyl, furyl, thienyl, pyrryl, pyridyl, pyranyl, quinolyl, indyl, carbazyl or the anilino a kind of (further, wherein the carbonatoms of alkyl or alkoxyl group is 1～12), n=1～4; The structural formula of further preferred compound is as follows again:
Figure BDA0000037275220000082
Figure BDA0000037275220000091
Go up in the structural formula with I-IV, wherein R 1, R 4, R 5, R 8Be H, R 2, R 7, R 3And R 6Preferred structure can be shown in following a kind of or hydrogen atom 29 kinds:
Figure BDA0000037275220000101
Figure BDA0000037275220000102
Description of drawings
Fig. 1: multilayer organic electroluminescence device structural representation;
A class electroluminescent organic material of the present invention can be applicable to luminescent layer or carrier blocking layers in the multilayer organic electroluminescence device.
This figure is the electroluminescent device of a multilayered structure, and it 1 is represented transparent glass and adhere to superincumbent conductive layer (positive pole) ITO (tin indium oxide); 5 represent metal (Al, Mg:Ag alloy, Ca, Na, K) layer (negative pole); 2,3,4 representatives are clipped in two carrier injection layer (hole injection/transport layer 2 and electronics injection/transport layer 4) and the luminescent layer 3 between the two poles of the earth.Material wherein of the present invention can be directly used as luminescent layer 3 as luminescent layer 3 or with adulterated main body or guest materials, and other are two-layer selects hole injection/transport material (as NPB etc.) and electronics injection/transport material (as TPBi etc.) respectively for use; Material of the present invention has the character of hole injection/transport material or electronics injection/transport material simultaneously, can replace transmitting the class material and use, and possesses luminescent properties simultaneously.
Hole and electronics inject from positive and negative polarities respectively, transmission in hole transmission layer and electron transfer layer (also being luminescent layer) respectively in two-layer near interface zone electronics and hole-recombination, and produces exciton, exciton is got back to ground state by radiative transition, just has light to send.This radiative color can be used material of the present invention and can prepare blue luminescent device by changing the compound change of using as luminescent layer.Adding can pack between one deck electronics injecting layer and/or electron transfer layer, electroluminescence layer and anode one deck hole injecting layer and/or the hole migrating layer of packing between electroluminescence layer and the negative electrode is in order to improve device performance.
The compounds of this invention all has in solution and solid film than hyperfluorescence, can form good amorphous thin film, has goodish heat, light equistability simultaneously again.Show higher carrier mobility ability and very high electroluminescent efficiency in the electroluminescent device applications.These el light emitting devices can be as the application on self luminous indicator elment such as signal lamp, aplhanumeric visual display, direction board, the photoelectronic coupler, in various flat-panel monitor (display screens of mobile phone, Digital Video, Digit camera, palm PC etc.) and the electronic imaging technology.
The electroluminescent device spectrogram of Fig. 2: embodiment 11 preparations;
The electroluminescent device efficient luminance graph of Fig. 3: embodiment 11 preparations;
The nuclear magnetic spectrogram (from top to bottom) of Fig. 4: embodiment 1,2,3 products.
Embodiment
Luminous organic material of the present invention adopts the compound and 9 that contains corresponding aldehyde groups, and method prepares below the heating condition in acetic acid for 10-phenanthrenequione, ammonium acetate.
Compounds process for production thereof:
Figure BDA0000037275220000111
Embodiment 1:1, the 2-phenylbenzene replaces 9,10-phenanthro-imidazoles
Figure BDA0000037275220000112
An amount of phenanthrenequione (2.0g), phenyl aldehyde (0.5ml), aniline (0.5ml) and ammonium acetate (8.0g) are heated to 140 ℃ of backflows after two hours in the 120ml Glacial acetic acid, stop heating, be cooled to the room temperature after-filtration, obtain white solid, adopt SiO 2Post separates, and developping agent is CH 2Cl 2, purifying obtains target product, productive rate 90.5%.
1H?NMR(500MHz，DMSO，ppm)：8.93(d，J＝8.2Hz，1H)，8.75(d，J＝8.5Hz，1H)，8.69(d，J＝7.6Hz，1H)，7.78(t，J＝7.6Hz，7.0Hz，1H)，7.73-7.65(m，6H)，7.58(dd，J＝7.9Hz，2.1Hz，2H)，7.55(t，J＝7.0Hz，7.3Hz，1H)，7.39-7.30(m，4H)，7.08(d，J＝8.2Hz，1H)。Mass-spectrometric data (C 27H 18N 2) theoretical value: 370.5; Measured value: 370.2.Ultimate analysis (C 27H 18N 2) theoretical value: C, 87.54; H, 4.90; N, 7.56. measured value: C, 87.50; H, 4.92; N, 7.55.
Show and obtained target product.
Embodiment 2:4,4-pair-(1-phenyl-9,10-phenanthro-imidazoles) biphenyl
With an amount of phenanthrenequione (2.0g), 4,4-two substituted biphenyl dialdehydes (1.0g), aniline (0.5ml) and ammonium acetate (8.0g) are heated to 140 ℃ of backflows in the 120ml Glacial acetic acid, after 2 hours, stop heating, be cooled to the room temperature after-filtration, obtain the yellow-green colour solid, adopt SiO 2Post separates, and developping agent is CH 2Cl 2, purifying obtains target product, productive rate 80.5%.
1H?NMR(500MHz，DMSO，ppm)：8.94(d，J＝8.5Hz，2H)，8.89(d，J＝8.2Hz，2H)，8.72(d，J＝8.2Hz，2H)，7.80-7.65(m，22H)，7.57(t，J＝7.9Hz，7.6Hz，2H)，7.35(t，J＝7.3Hz，7.3Hz，2H)，7.09(d，J＝8.2Hz，2H)。Mass-spectrometric data (C 54H 34N 4) theoretical value: 738.28; Measured value: 739.0.Ultimate analysis (C 54H 34N 4) theoretical value: C, 87.78; H, 4.64; N, 7.58.Measured value: C, 87.80; H, 4.62; N, 7.57.
Show and obtained target product.
Embodiment 3:1,3,5-triphenyl-(1-phenyl-9,10-phenanthro-imidazoles) benzene
Figure BDA0000037275220000122
With an amount of phenanthrenequione (2.0g), 1,3, the 5-triphenyl replaces three aldehyde (0.6g), aniline (1ml) and ammonium acetate (10g) and is heated to 140 ℃ of backflows after two hours in the 120ml Glacial acetic acid, stop heating, be cooled to the room temperature after-filtration, obtain the yellow-green colour solid, adopt SiO 2Post separates, and developping agent is CH 2Cl 2, purifying obtains target product, productive rate 76.5%.
1H?NMR(500MHz，DMSO，ppm)：8.93(d，J＝8.8Hz，3H)，8.88(d，J＝7.3Hz，3H)，8.72(d，J＝7.6Hz，3H)，7.98(s，3H)，7.93(d，J＝8.2Hz，6H)，7.80-7.66(m，27H)，7.57(t，J＝7.9Hz，7.6Hz，3H)，7.35(t，J＝8.2Hz，7.3Hz，3H)，7.09(d，J＝7.9Hz，3H)。Mass-spectrometric data (C 87H 54N 6) theoretical value: 1182.44; Measured value: 1183.50.Ultimate analysis (C 87H 54N 6) theoretical value: C, 88.30; H, 4.60; N, 7.10.Measured value: C, 88.26; H, 4.60; N, 7.08.
Show and obtained target product.
Embodiment 4:4-(1-phenyl-9,10-phenanthro-imidazoles)-triphenylamine
Figure BDA0000037275220000131
With an amount of phenanthrenequione (2.0g), 4-triphenylamine aldehyde (1.0g), aniline (1.2ml) and ammonium acetate (8.0g) in the 120ml Glacial acetic acid, be heated in 140 ℃ refluxed 2 hours after, stop heating, be cooled to the room temperature after-filtration, obtain the light green solid, adopt SiO 2Post separates, and developping agent is CH 2Cl 2, purifying obtains white object product, productive rate 75.5%.
1H?NMR(500MHz，DMSO，ppm)：8.93(d，J＝8.8Hz，1H)，8.88(d，J＝7.3Hz，1H)，8.68(d，J＝7.6Hz，1H)，7.77(t，J＝7.9Hz，7.6Hz，1H)，7.72-7.60(m，6H)，7.54(t，J＝7.9Hz，7.6Hz，3H)，7.48(d，J＝7.9Hz，2H)，7.34-7.30(m，5H)，7.11(t，J＝8.2Hz，7.3Hz，2H)，7.05-6.90(m，5H)，6.84(d，J＝7.9Hz，2H)。Mass-spectrometric data (C 39H 27N 3) theoretical value: 537.2; Measured value: 537.4.Ultimate analysis (C 39H 27N 3) theoretical value: C, 87.12; H, 5.06; N, 7.82.Measured value: C, 87.2; H, 5.0; N, 7.7.
Show and obtained target product.
Embodiment 5:4,4 '-two-(1-phenyl-9,10-phenanthro-imidazoles)-triphenylamine
Figure BDA0000037275220000141
With an amount of phenanthrenequione (3.0g), 4,4 '-triphenylamine dialdehyde (2.0g), aniline (2ml) and ammonium acetate (10.0g) were heated to 140 ℃ of backflows after two hours in the 120ml Glacial acetic acid, stop heating, were cooled to the room temperature after-filtration, obtain the light green solid, adopt SiO 2Post separates, and developping agent is CH 2Cl 2Purification obtains the white object product, productive rate 68.0%.
1H?NMR(500MHz，DMSO，ppm)：8.94(d，J＝8.8Hz，2H)，8.88(d，J＝7.3Hz，2H)，8.69(d，J＝7.6Hz，2H)，7.72-7.60(m，14H)，7.55(t，J＝7.9Hz，7.6Hz，2H)，7.52(d，J＝7.9Hz，4H)，7.37(t，J＝8.2Hz，7.3Hz，2H)，7.33(t，J＝8.6Hz，7.2Hz，2H)，7.17(t，J＝8.2Hz，7.6Hz，1H)，7.06(t，J＝8.2Hz，7.3Hz，4H)，6.91(t，J＝8.2Hz，7.3Hz，4H)。Mass-spectrometric data (C 60H 39N 5) theoretical value: 830.0; Measured value: 831.2.Ultimate analysis (C 60H 39N 5) theoretical value: C, 86.83; H, 4.74; N, 8.44.Measured value: C, 86.7; H, 4.8; N, 8.4.
Show and obtained target product.
Embodiment 6:4,4 ', 4 "-three-(1-phenyl-9,10-phenanthro-imidazoles)-triphenylamine
Figure BDA0000037275220000142
With an amount of phenanthrenequione (1.0g), aniline (1.2ml), 4,4 ', 4 "-triphenylamine dialdehyde (0.4g) and ammonium acetate (6.0g) be heated to 140 ℃ of streams after two hours in the 120ml Glacial acetic acid; and stop heating; be cooled to the room temperature after-filtration, obtain the light green solid, adopt SiO 2Post separates, and developping agent is CH 2Cl 2Purification obtains faint yellow target product, productive rate 60.0%.
1H?NMR(500MHz，DMSO，ppm)：8.94(d，J＝8.8Hz，3H)，8.88(d，J＝7.3Hz，3H)，8.70(d，J＝7.6Hz，3H)，7.75-7.66(m，14H)，7.54(m，9H)，7.34(t，J＝8.2Hz，7.3Hz，3H)，7.08(t，J＝7.6Hz，7.3Hz，3H)，6.95(d，J＝7.9Hz，3H)。Mass-spectrometric data (C 81H 51N 7) theoretical value: 1122.3; Measured value: 1123.3.Ultimate analysis (C 81H 51N 7) theoretical value: C, 86.68; H, 4.58; N, 8.74.Measured value: C, 86.7; H, 4.0; N, 8.6.
Show and obtained target product.
Embodiment 7:4,4-pair-2-(1-benzene cyano group-9,10-phenanthro-imidazoles) biphenyl
Figure BDA0000037275220000151
With an amount of phenanthrenequione (2.0g), 4,4-two substituted biphenyl dialdehydes (0.8g), cyano-aniline (3.0g) and ammonium acetate (6.0g) are heated to 140 ℃ in the 120ml Glacial acetic acid, after two hours, stop heating, be cooled to the room temperature after-filtration, obtain the yellow-green colour solid, adopt SiO 2Post separates, and developping agent is CH 2Cl 2Purification obtains faint yellow target product, productive rate 80.5%.
1H?NMR(500MHz，DMSO，ppm)：8.94(d，J＝8.5Hz，2H)，8.89(d，J＝8.2Hz，2H)，8.72(d，J＝8.2Hz，2H)，8.22(d，J＝8.2Hz，2H)，8.06(d，J＝8.2Hz，2H)，7.80-7.65(m，16H)，7.57(t，J＝7.9Hz，7.6Hz，2H)，7.35(t，J＝7.3Hz，7.3Hz，2H)，7.09(d，J＝8.2Hz，2H)。Mass-spectrometric data (C 56H 32N 6) theoretical value: 738.28; Measured value: 739.0.Ultimate analysis (C 56H 32N 6) theoretical value: C, 85.26; H, 4.09; N, 10.65.Measured value: C, 85.2; H, 4.09; N, 10.8.
Show and obtained target product.
Embodiment 8: two-4 '-(1,2-phenylbenzene-9,10-phenanthro-imidazoles) replaces anthracene
Figure BDA0000037275220000152
An amount of phenanthrenequione (2.0g), 9,10 phenylbenzene dialdehydes (0.6g), aniline (3ml) and ammonium acetate (3.0g) are heated to 140 ℃ in the 120ml Glacial acetic acid, reflux after two hours, stop heating, be cooled to the room temperature after-filtration, obtain the yellow-green colour solid, adopt SiO 2Post separates, and developping agent is CH 2Cl 2Purification obtains target product, productive rate 60.2%.
1H?NMR(500MHz，DMSO，ppm)：8.98(d，J＝8.5Hz，4H)，8.93(d，J＝8.2Hz，4H)，8.79(d，J＝8.2Hz，4H)，7.89-7.86(m，16H)，7.99-7.79(m，18H)，7.74(t，J＝7.9Hz，7.6Hz，4H)，7.59(t，J＝7.3Hz，7.3Hz，4H)，7.59-7.36(m，8H)，7.48-7.46(m，16H)，7.49(t，J＝7.9Hz，7.6Hz，4H)，7.16(d，J＝8.2Hz，4H)。Mass-spectrometric data (C 68H 42N 4) theoretical value: 915.1; Measured value: 916.4.Ultimate analysis (C 68H 42N 4) theoretical value: C, 89.25; H, 4.63; N, 6.12.Measured value: C, 89.4; H, 4.5; N, 6.1.
Show and obtained target product.
Embodiment 9:3-(1-phenyl-9,10-phenanthro-imidazoles)-9-phenyl-carbazole
Figure BDA0000037275220000161
An amount of phenanthrenequione (2.0g), 3-carbazole aldehyde (1.0g), aniline (1.0ml) and ammonium acetate (3.0g) are heated to 140 ℃ in the 120ml Glacial acetic acid, stop heating, be cooled to the room temperature after-filtration, obtain the light green solid, adopt SiO 2Post separates, and developping agent is CH 2Cl 2Purification obtains the white object product, productive rate 80.5%.
1H?NMR(500MHz，DMSO，ppm)：8.96(d，J＝8.5Hz，1H)，8.91(d，J＝8.2Hz，4H)，8.76(d，J＝8.2Hz，1H)，8.35(s，1H)，8.08(d，J＝8.2Hz，1H)，7.81-7.76(m，4H)，7.76-7.70(m，6H)，7.64(d，J＝7.9Hz，2H)，7.57(t，J＝7.3Hz，7.3Hz，2H)，7.45(t，J＝7.6Hz，7.3Hz，1H)，7.39-7.30(m，4H)，7.16(d，J＝8.2Hz，1H)。。Mass-spectrometric data (C 39H 27N 3) theoretical value: 535.2; Measured value: 535.4.Ultimate analysis (C 39H 25N 3) theoretical value: C, 87.45; H, 4.70; N, 7.84.Measured value: C, 87.5; H, 4.7; N, 7.8.
Show and obtained target product.
Embodiment 10:9-(1-phenyl-9,10-phenanthro-imidazoles)-9-phenyl-carbazole
Figure BDA0000037275220000162
An amount of phenanthrenequione (2.0g), 9-carbazole aldehyde (1.0g), aniline (1.0g) and ammonium acetate (3.0g) are heated to 140 ℃ in the 120ml Glacial acetic acid, stop heating, be cooled to the room temperature after-filtration, obtain the light green solid, adopt SiO 2Post separates, and developping agent is CH 2Cl 2Purification obtains target product, productive rate 90.5%.
1H?NMR(500MHz，DMSO，ppm)：8.96(d，J＝8.5Hz，2H)，8.91(d，J＝8.2Hz，2H)，8.74(d，J＝8.2Hz，2H)，8.26(d，J＝8.2Hz，2H)，7.84-7.78(m，12H)，7.71(t，J＝7.9Hz，7.6Hz，2H)，7.65(d，J＝8.2Hz，4H)，7.57(t，J＝7.3Hz，7.3Hz，2H)，7.44(t，J＝7.3Hz，7.3Hz，4H)，7.40-7.34(m，6H)，7.30(t，J＝7.3Hz，7.3Hz，4H)，7.11(d，J＝8.2Hz，2H)。Mass-spectrometric data (C 39H 27N 3) theoretical value: 535.2; Measured value: 535.4.Ultimate analysis (C 39H 25N 3) theoretical value: C, 87.45; H, 4.70; N, 7.84.Measured value: C, 87.5; H, 4.7; N, 7.8.
Show and obtained target product.
Embodiment 11:
Figure BDA0000037275220000171
To deposit tin indium oxide (ITO) glass substrate of transparent anode through toluene, acetone and ethanol dry after cleaning repeatedly, the hole mobile material that then prepares one deck 60nm: N by the method for vacuum-evaporation, N '-phenylbenzene-N, N '-two (1-naphthyl)-1,1 '-biphenyl-4,4 '-diamines (NPB), on this hole transmission layer, continue then by the material among the present invention of vacuum evaporation last layer 60nm (embodiment 2 described materials), at last again evaporation one deck LiF (0.5nm)/Al (100nm) as the negative electrode of device, galvanic positive pole is added on the ITO layer, negative pole is added on metal level, can obtain from the bright sky uniformly blue light that the ITO layer sends, the CIE coordinate is (0.16,0.21), opens bright voltage 2.8V, high-high brightness is 40000cd/A, maximum efficiency is 6.87cd/A, and maximum external quantum efficiency is 4.0%, and maximum lumen efficient is 6.2lm/W; When brightness reaches 1000cd/m 2The time, current efficiency is 6.74cd/A, and external quantum efficiency is 3.9%, and luminous main peak is positioned at 468nm.
Embodiment 12:
Figure BDA0000037275220000172
To deposit tin indium oxide (ITO) glass substrate of transparent anode through toluene, acetone and ethanol dry after cleaning repeatedly, the hole mobile material that then prepares one deck 60nm: N by the method for vacuum-evaporation, N '-phenylbenzene-N, N '-two (1-naphthyl)-1,1 '-biphenyl-4,4 '-diamines (NPB), on this hole transmission layer, continue then by the material among the present invention of vacuum evaporation last layer 20nm (example 7 described materials), evaporation one deck 1 again, 3,5-three (benzene (TPBi) of 1-phenyl-1H-benzimidazolyl-2 radicals-yl), at last again evaporation one deck LiF (0.5nm)/Al (100nm) as the negative electrode of device, galvanic positive pole is added on the ITO layer, negative pole is added on metal level, can obtains from the bright sky uniformly blue light that the ITO layer sends, the CIE coordinate is (0.16,0.23), open bright voltage 3.8V, high-high brightness is 34000cd/A, and maximum efficiency is 6.62cd/A, maximum external quantum efficiency is 3.6%, and maximum lumen efficient is 4.1lm/W; When brightness reaches 1000cd/m 2The time, current efficiency is 6.56cd/A, and external quantum efficiency is 3.6%, and luminous main peak is positioned at 468nm.
Embodiment 13:
Figure BDA0000037275220000181
To deposit tin indium oxide (ITO) glass substrate of transparent anode through toluene, acetone and ethanol dry after cleaning repeatedly, the hole mobile material that then prepares one deck 60nm: N by the method for vacuum-evaporation, N '-phenylbenzene-N, N '-two (1-naphthyl)-1,1 '-biphenyl-4,4 '-diamines (NPB), on this hole transmission layer, continue then by the material among the present invention of vacuum evaporation last layer 20nm (example 3 described materials), evaporation one deck 1 again, 3,5-three (benzene (TPBi) of 1-phenyl-1H-benzimidazolyl-2 radicals-yl), at last again evaporation one deck LiF (0.5nm)/Al (100nm) as the negative electrode of device, galvanic positive pole is added on the ITO layer, negative pole is added on metal level, can obtains from the bright sky uniformly blue light that the ITO layer sends, the CIE coordinate is (0.20,0.22), open bright voltage 4.2V, high-high brightness is 5000cd/A, and maximum efficiency is 3.1cd/A, maximum external quantum efficiency is 1.3%, and maximum lumen efficient is 1.8lm/W; When brightness reaches 1000cd/m 2The time, current efficiency is 1.49cd/A, and external quantum efficiency is 1.0%, and luminous main peak is positioned at 451nm.
Embodiment 14:
Figure BDA0000037275220000191
To deposit tin indium oxide (ITO) glass substrate of transparent anode through toluene, acetone and ethanol dry after cleaning repeatedly, the hole mobile material that then prepares one deck 60nm: N by the method for vacuum-evaporation, N '-phenylbenzene-N, N '-two (1-naphthyl)-1,1 '-biphenyl-4,4 '-diamines (NPB), on this hole transmission layer, continue then by the material among the present invention of vacuum evaporation last layer 20nm (example 8 described materials), evaporation one deck 1,3 again, the 5-three (benzene (TPBi) of 1-phenyl-1H-benzimidazolyl-2 radicals-yl), at last again evaporation one deck LiF (0.5nm)/Al (100nm) as the negative electrode of device, galvanic positive pole is added on the ITO layer, negative pole is added on metal level, can obtain the bright day blue light uniformly that sends from the ITO layer, the CIE coordinate is (0.17,0.25), opening bright voltage 2.8V, high-high brightness is 14000cd/A, maximum efficiency is 5.0cd/A, maximum external quantum efficiency is 3.0%, and maximum lumen efficient is 2.8lm/W, and luminous main peak is positioned at 472nm.

Claims (10)

1. one kind 9,10-phenanthro-imdazole derivatives, it has following general structure:
Figure FDA0000037275210000011
Wherein, R 0～R 8Be hydrogen, alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthyl, furyl, thienyl, pyrryl, pyridyl, pyranyl, quinolyl, indyl, a kind of in carbazyl or the anilino, the X phenyl, xenyl, methyl biphenyl, the triphenyl substituted benzene, the methyl triphenyl substituted benzene, tetraphenyl, methyl tetraphenyl substituted benzene, pentapheneyl, hexaphenyl, anthryl, anthryl derivative, naphthyl, naphthyl derivatives, carbazyl, the carbazyl derivative, the triphen amido, the triphenylamine radical derivative, tetraphenyl is silica-based, the tetraphenyl-silicon radical derivative, Spirofluorene-based, Spirofluorene-based derivative, the tetraphenyl vinyl, the tetraphenyl ethenyl derivatives, thienyl, the thienyl derivative, rope sieve cyclic group or rope Luo Huan radical derivative, n is 1～4.
2. as claimed in claim 1 a kind of 9,10-phenanthro-imdazole derivatives is characterized in that: the carbonatoms of alkyl or alkoxyl group is 1～12.
3. as claimed in claim 1 a kind of 9,10-phenanthro-imdazole derivatives is characterized in that: X is a phenyl, R 1, R 4, R 5, R 8Be H, R 2, R 7, R 3And R 6A kind of in hydrogen, alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthyl, furyl, thienyl, pyrryl, pyridyl, pyranyl, quinolyl, indyl, carbazyl or the anilino.
4. as claimed in claim 1 a kind of 9,10-phenanthro-imdazole derivatives is characterized in that: X is xenyl or methyl biphenyl, R 1, R 4, R 5, R 8Be H, R 2, R 7, R 3And R 6A kind of in hydrogen, alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthyl, furyl, thienyl, pyrryl, pyridyl, pyranyl, quinolyl, indyl, carbazyl or the anilino.
5. as claimed in claim 1 a kind of 9,10-phenanthro-imdazole derivatives is characterized in that: X is triphenyl substituted benzene, methyl triphenyl substituted benzene, tetraphenyl or methyl tetraphenyl substituted benzene, R 1, R 4, R 5, R 8Be H, R 2, R 7, R 3And R 6A kind of in hydrogen, alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthyl, furyl, thienyl, pyrryl, pyridyl, pyranyl, quinolyl, indyl, carbazyl or the anilino.
6. as claimed in claim 1 a kind of 9,10-phenanthro-imdazole derivatives is characterized in that: X is triphen amido, methyl triphen amido or contains naphthalene triphen amido, wherein R 1, R 4, R 5, R 8Be H, R 2, R 7, R 3And R 6A kind of in hydrogen, alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthyl, furyl, thienyl, pyrryl, pyridyl, pyranyl, quinolyl, indyl, carbazyl or the anilino.
7. as claimed in claim 1 a kind of 9,10-phenanthro-imdazole derivatives is characterized in that: X is carbazyl, phenyl carbazole base or naphthyl carbazole base, R 1, R 4, R 5, R 8Be H, R 2, R 7, R 3And R 6A kind of in hydrogen, alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthyl, furyl, thienyl, pyrryl, pyridyl, pyranyl, quinolyl, indyl, carbazyl or the anilino.
8. as claimed in claim 1 a kind of 9,10-phenanthro-imdazole derivatives is characterized in that: X is that tetraphenyl is silica-based or the methyl tetraphenyl is silica-based, R 1, R 4, R 5, R 8Be H, R 2, R 7, R 3And R 6A kind of in hydrogen, alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthyl, furyl, thienyl, pyrryl, pyridyl, pyranyl, quinolyl, indyl, carbazyl or the anilino.
9. as claimed in claim 1 a kind of 9,10-phenanthro-imdazole derivatives is characterized in that: X is that anthryl, phenyl replace anthryl, naphthyl or phenyl substituted naphthyl, Spirofluorene-based, tetraphenyl vinyl, thienyl or rope sieve cyclic group, R 1, R 4, R 5, R 8Be H, R 2, R 7, R 3And R 6A kind of in hydrogen, alkyl, hydroxyl, alkoxyl group, nitro, cyano group, amino, sulfydryl, halogen atom, phenyl, tolyl, naphthyl, furyl, thienyl, pyrryl, pyridyl, pyranyl, quinolyl, indyl, carbazyl or the anilino.
10. any one is described a kind of 9 for claim 1～9, and 10-phenanthro-imdazole derivatives is in the application aspect electroluminescent organic material.
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Application publication date: 20110921