CN100548984C - A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material - Google Patents

A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material Download PDF

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CN100548984C
CN100548984C CN200710114641.XA CN200710114641A CN100548984C CN 100548984 C CN100548984 C CN 100548984C CN 200710114641 A CN200710114641 A CN 200710114641A CN 100548984 C CN100548984 C CN 100548984C
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indoles
organic electroluminescent
carbazole derivative
carbazole
octyl
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陶绪堂
赵华平
蒋民华
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Shandong University
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Abstract

The present invention relates to a kind of high brightness, high efficiency indoles [3,2-b] carbazole derivative organic electroluminescent material, belong to the electroluminescent organic material technical field.A kind of indoles [3,2-b] carbazole derivative organic electroluminescent compound, general structure is as follows: wherein, R 3, R 7The aromatic base that=alkyl or alkyl replace, R 1, R 2, R 4-R 6, R 8=hydrogen atom, benzene, naphthalene, anthracene, fluorenes, carbazole, three arylamine, thiophene, pyridine, pyrans, quinoline, pyrroles, furans or imidazoles.Compound among the present invention all has very strong fluorescence in solution and solid film, also have good film-forming properties, thermostability and light stability simultaneously.

Description

A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material
Technical field
The present invention relates to a kind of high brightness, high efficiency indoles [3,2-b] carbazole derivative organic electroluminescent material, belong to the electroluminescent organic material technical field.
Background technology
Because existing technique of display can't satisfy people's requirement more and more higher to device for display of message, impel people constantly to seek more novel luminescent material more efficiently, further investigate its luminescence mechanism, the display device that processability is higher, cost is cheaper.(organic light-emitting diodes, OLED) flat panel display as a new generation arises at the historic moment organic electroluminescence device.Advantages such as series of advantages such as OLED has from main light emission, low voltage direct drive, solidifies entirely, the visual angle is wide, color is abundant are compared with liquid-crystal display, and OLED does not need backlight, the visual angle is big, power is low, response speed is fast, with low cost.Therefore, display of organic electroluminescence has boundless application prospect.
The luminescent material of excellent property is the basis of preparation organic electroluminescence device, the selection that organic materials is a material with its inherent diversity provides broad scope, design, assembling and reduction by to organic molecular structure can realize the demonstration of any color from ruddiness to the blue light.Must satisfy following requirement as luminescent material:
(1) high fluorescence quantum efficiency, fluorescence spectrum mainly is distributed in 400～700nm visible region;
(2) good characteristic of semiconductor promptly has high electric conductivity, can conduction electron or hole;
(3) good film-forming properties does not produce pin hole in the thin layer of tens nano thickness;
(4) good thermostability and light stability.
At present generally can be divided into two big classes by the molecular structure of compound: organic micromolecule compound and high molecular polymer as the luminous organic material of OLED.Compare with high molecular polymer, organic micromolecule compound has that chemically modified is strong, range of choice is wide, be easy to characteristics such as purification, fluorescence quantum yield height.As publication number is that the Chinese patent of CN1362464 discloses a kind of electroluminescent organic material, and this material is the derivative of anthracene, but does not find as the relevant report of electroluminescent organic material with indoles [3,2-b] carbazole derivative.
Indoles [3,2-b] carbazole has the condensed ring structure of similar pentacene, have bigger band gap and lower HOMO energy level, its big conjugate planes rigid structure helps the transmission in current carrier (electronics or hole), and makes it have good thermostability and environmental stability.Indoles [3,2-b] carbazole also has the advantage of a highly significant, is exactly that it can be very easy to such an extent that carry out chemically modified, at indoles [3,2-b] introduce fluorophors such as fluorenes, carbazole, triphenylamine, naphthalene, anthracene on the molecular skeleton of carbazole, thus can obtain a series of new high performance luminescent materials.
Summary of the invention
At the deficiencies in the prior art, the invention provides a kind of novel fluorescent material, can be used as the luminescent material in the organic electroluminescence device, expand the kind of the luminous organic material that is used for organic electroluminescence device.
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, general structure is as follows:
Figure C20071011464100031
Wherein, R 3, R 7The aromatic base that=alkyl or alkyl replace, R 1-R 2, R 4-R 6, R 8=hydrogen atom, benzene, naphthalene, anthracene, fluorenes, carbazole, three arylamine, thiophene, pyridine, pyrans, quinoline, pyrroles, furans or imidazoles.
Preferably, indoles [3,2-b] carbazole derivative organic electroluminescent compound, this structural formula of compound is as follows:
Wherein, R 3, R 7Be all the aromatic base of 1～24 carbon atom alkyl, alkoxyl group, alkyl replacement, the heterocyclic substituent that alkyl replaces; R 8A kind of in hydrogen atom, benzene, naphthalene, anthracene, pyrene, pyridine, thiophene, carbazole, fluorenes, the triarylamine group.
Preferably, indoles [3,2-b] carbazole derivative organic electroluminescent compound is characterized in that this structural formula of compound is as follows:
Figure C20071011464100042
Wherein, R 3, R 7Be all the aromatic base of 1～24 carbon atom alkyl, alkoxyl group, alkyl replacement, the heterocyclic substituent that alkyl replaces; R 1, R 5And R 8Be in hydrogen atom, benzene, naphthalene, anthracene, pyrene, pyridine, thiophene, carbazole, fluorenes, the triarylamine group any one, R 1, R 5And R 8Can be the same or different.
Preferably, indoles [3,2-b] carbazole derivative organic electroluminescent compound, this structural formula of compound is as follows:
Figure C20071011464100043
Wherein, R 3, R 7Be all the aromatic base of 1～24 carbon atom alkyl, alkoxyl group, alkyl replacement or the heterocyclic substituent that alkyl replaces; R 2, R 6And R 8Be in hydrogen atom, benzene, naphthalene, anthracene, pyrene, pyridine, thiophene, carbazole, fluorenes, the triarylamine group any one, R 2, R 6And R 8Can be the same or different.
More excellent, indoles [3,2-b] carbazole derivative organic electroluminescent compound, R 2, R 3Be selected among group A1～A13 in the table 1, R 1, R 4And R 5Be selected from one of group A12～A30 in the table 1.
Table 1
Among the present invention compound in the organic electroluminescence device that the multilayer organic materials is formed carrier blocking layers or the application in the luminescent layer.
Detailed Description Of The Invention
According to three kinds of structures of above-mentioned I ~ III, associative list 1 couple of the present invention be further elaborated:
The I compounds, preferred substituted R 2, R 3Can be among the group A1 ~ A13 in the identical table 1, R 1Can be among A12 ~ A30.In the I class formation particularly preferred compound be I-1 to I-12, structural formula is as follows:
Figure C20071011464100052
Figure C20071011464100061
The II compounds, preferred substituted R 2, R 3Can be among the group A1～A13 in the identical table 1, R 1, R 4And R 5Can be identical or different as one among the listed group A12～A30 of table 1, in the II class formation particularly preferred compound be II-1 to II-32, structural formula is as follows:
Figure C20071011464100062
Figure C20071011464100071
Figure C20071011464100081
Figure C20071011464100091
Figure C20071011464100101
The III compounds, preferred substituted R 2, R 3Can be among the group A1 ~ A13 in the identical table 1, R 1, R 4And R 5Can be identical or different as one among the listed group A12 ~ A30 of table 1, in the III class formation particularly preferred compound be III-1 to III-32, structural formula is as follows:
Figure C20071011464100102
Figure C20071011464100111
Figure C20071011464100131
Figure C20071011464100141
The synthetic route of indoles among the present invention [3,2-b] carbazole derivative organic electroluminescent material is as follows:
Figure C20071011464100142
The synthetic method of luminous organic material of the present invention mainly adopts Vilsmeier reaction well known in the art, Wittig reaction, organic synthesis such as Suzuki reaction.
Beneficial effect
Luminous organic material of the present invention has following characteristics: fluorescence is strong, and glow color is tunable, and Heat stability is good has good carrier transmission performance, can form stable unformed film.
Material among the present invention can be used as luminescent material, also has carrier transmission performance simultaneously.Compound among the present invention all has very strong fluorescence in solution and solid film, also have good film-forming properties, thermostability and light stability simultaneously.
Description of drawings
Fig. 1 be the present invention prepare 5, the electroluminescent spectrum of the electroluminescent device of 11-di-n-octyl-6-(4-triphen amido) styryl-indoles [3,2-b] carbazoles (I-2).
Fig. 2 be the present invention prepare 5, the voltage-to-current density-brightness curve of the electroluminescent device of 11-di-n-octyl-6-(4-triphen amido) styryl-indoles [3,2-b] carbazoles (I-2).
Fig. 3 be the present invention prepare 5, the current density-current efficiency-luminous efficiency curve of the electroluminescent device of 11-di-n-octyl-6-(4-triphen amido) styryl-indoles [3,2-b] carbazoles (I-2).
Embodiment
Below in conjunction with embodiment and Figure of description, the present invention is further elaborated.
Embodiment 1. synthetic routes are as follows:
Figure C20071011464100151
Synthesizing of the used part intermediate of the present invention:
Compound 1 according to document (J.Am.Chem.Soc., 2005,127, method 614-618) is synthetic.
Synthesizing of compound 2: add 0.372mL (4.8mmol) N in the round-bottomed flask of 250mL, dinethylformamide is cooled to 0 ℃, slowly drips 0.44mL (4.8mmol) phosphorus oxychloride then, generates white solid.Add 20mL 1, the 2-ethylene dichloride dissolves white solid.Then 1.924g (4mmol) compound 1 is dissolved in 60mL 1, the solution of 2-ethylene dichloride slowly is added drop-wise in the round-bottomed flask, slowly returns to room temperature then, continues reaction 1 hour, is warming up to backflow then, reacts 48 hours.After reaction finishes, steam and remove major part 1, the 2-ethylene dichloride is cooled to room temperature, and resistates is poured in the frozen water, is neutralized to about PH=8 with sodium bicarbonate aqueous solution, uses dichloromethane extraction, washing, anhydrous sodium sulfate drying.Cross post with sherwood oil/methylene dichloride=4/1 as elutriant and purify, get 5,11-di-n-octyl-6-formyl indole [3,2-b] carbazoles (2) 954mg. 1H?NMR(CDCl 3，400MHz，ppm)δ：0.83-0.86(m，6H)，1.23-1.46(m，20H)，1.79-1.83(m，2H)，1.90-1.95(m，2H)，4.42-4.46(t，2H，J＝7.29Hz)，4.55-4.59(t，2H，J＝7.80Hz)，7.28-7.32(m，2H)，7.45-7.56(m，4H)，8.19(d，1H，J＝7.66Hz)，8.27(s，1H)，8.61(d，1H，J＝8.14Hz)，11.35(s，1H). 13C?NMR(CDCl 3，100.61MHz，ppm)δ：13.65，22.11，26.32，26.88，28.20，28.44，28.70，28.83，28.92，31.27，31.32，42.68，46.79，104.82，108.27，109.33，115.54，118.34，119.04，119.35，121.25，121.83，122.20，124.41，124.90，126.13，135.19，135.48，141.65，142.92，189.81.Anal.Calcd?for?C 35H 44N 2O：C，82.63；H，8.72；N，5.51；O，3.14.Found：C，82.61；H，8.69；N，5.50。
Synthesizing of compound 3: (1.275g, 2.5mmol) (1.926g 3.75mmol), adds 100mL exsiccant methylene dichloride then with the p-bromobenzyl bromide phosphonium salt to add compound 2 at the bottom of the 250mL garden in the flask.Slowly add after thing to be mixed dissolves fully potassium tert.-butoxide (2.526g, 22.55mmol).Mixture at room temperature reacted 24 hours.Reaction is used dichloromethane extraction after finishing, washing, saturated common salt washing, anhydrous sodium sulfate drying.Cross post with sherwood oil/methylene dichloride=4/1 as elutriant and purify, get compound 3 (1.431g, productive rate: 86.3%). 1H?NMR(CDCl 3，400MHz，ppm)δ：0.84-0.88(m，6H)，1.14-1.31(m，16H)，1.38-1.39(m，2H)，1.45-1.47(m，2H)，1.73-1.76(m，2H)，1.93-1.97(m，2H)，4.38-4.41(t，2H，J＝7.32Hz，J＝7.23Hz)，4.45-4.39(t，2H，J＝8.02Hz，J＝7.88Hz)，6.93-6.97(m，1H)，7.04-7.08(m，1H)，7.21-7.25(m，1H)，7.37-7.47(m，4H)，7.49-7.61(m，4H)，7.97-8.02(m，2H)，8.18-8.25(dd，2H，J＝7.65Hz，J＝7.94Hz). 13C?NMR(CDCl 3，100.61MHz，ppm)δ：14.06，22.61，27.07，27.42，28.76，29.22，29.25，29.46，31.74，31.84，43.19，45.08，97.88，108.21，108.77，115.76，117.84，118.30，119.97，120.98，121.94，122.86，123.21，123.79，125.26，125.39，125.88，127.95，132.14，133.30，134.85，135.96，136.01，141.80，142.65.Anal.Calcd?for?C 42H 49BrN 2：C，76.23；H，7.46；N，4.23.Found：C，76.60；H，7.56；N，4.12.
Under the condition of nitrogen protection; with compound 3 (500mg; 0.76mmol), to (N; N '-phenylbenzene) phenylo boric acid (289mg, 1mmol), four (triphenyl phosphorus) palladium (0.116g; 0.1mmol);, 20mL tetrahydrofuran (THF) and 10mL (2M) aqueous sodium carbonate join in the 100mL there-necked flask, is warming up to backflow, reacted 24 hours.After reaction finished, reaction mixture was cooled to room temperature, uses the 100mL dichloromethane extraction, washing, saturated common salt washing, anhydrous sodium sulfate drying.Cross post with sherwood oil/methylene dichloride=4/1 as elutriant and purify, get compound 5,11-di-n-octyl-6-(4-triphen amido) styryl-indoles [3,2-b] carbazoles (I-2) (588mg, productive rate: 93.6%). 1H?NMR(CDCl 3，400MHz，ppm)δ：0.78-0.81(m，3H)，0.84-0.88(m，3H)，1.12-1.35(m，16H)，1.37-1.45(m，2H)，1.47-1.51(m，2H)，1.75-1.77(m，2H)，1.93-1.96(m，2H)，4.37-4.41(t，2H，J＝7.11Hz，J＝7.12Hz)，4.49-4.53(t，2H，J＝7.70Hz，J＝7.76Hz)，7.01-7.08(m，4H)，7.14-7.18(m，7H)，7.26-7.30(m，4H)，7.37-7.47(m，4H)，7.54-7.56(m，2H)，7.66-7.71(m，4H)，7.96-8.03(m，2H)，8.19(d，1H，J＝7.65Hz)，8.34(d，1H，J＝7.93Hz). 13C?NMR(CDCl 3，100.61MHz，ppm)δ：14.05，14.07，22.61，22.63，27.09，27.44，28.77，29.23，29.28，29.32，29.48，29.49，31.75，31.86，43.18，45.10，97.67，108.11，108.76，116.33，117.84，118.21，119.95，121.10，122.92，123.03，123.07，123.35，123.72，123.83，124.21，124.52，125.19，125.80，126.95，127.05，127.59，129.31，133.40，134.44，135.58，135.65，136.05，140.28，141.80，142.65，147.37，147.66.Anal.Calcd?for?C 60H 63N 3：C，87.23；H，7.69；N，5.09.Found：C，87.62；H，7.75；N，5.01.
Embodiment 2: compound 1,2,3 synthetic as embodiment 1, and difference is:
Under the condition of nitrogen protection; with compound 3 (500mg; 0.76mmol), 9; 9 '-di-n-butyl fluorenes-2-boric acid (322mg, 1mmol), four (triphenyl phosphorus) palladium (0.116g; 0.1mmol);, 20mL tetrahydrofuran (THF) and 10mL (2M) aqueous sodium carbonate join in the 100mL there-necked flask, is warming up to backflow, reacted 24 hours.After reaction finished, reaction mixture was cooled to room temperature, uses the 100mL dichloromethane extraction, washing, saturated common salt washing, anhydrous sodium sulfate drying.Cross post with sherwood oil/methylene dichloride=4/1 as elutriant and purify, get compound 5,11-di-n-octyl-6-[4-(9,9-di-n-butyl fluorenyl) styryl]-indoles [3,2-b] carbazoles (I-4) (567mg, productive rate: 86.8%). 1H?NMR(CDCl 3，400MHz，ppm)δ：0.63-0.72(m，8H)，0.79-0.82(m，3H)，0.85-0.88(m，3H)，1.06-1.16(m，5H)，1.19-1.34(m，16H)，1.36-1.44(m，2H)，1.46-1.50(m，2H)，1.53(s，1H)，1.76-1.80(m，2H)，1.92-2.00(m，2H)，2.04-2.06(m，4H)，4.41-4.54(m，4H)，7.06-7.10(m，2H)，7.30-7.50(m，8H)，7.64-7.67(m，2H)，7.74-7.81(m，6H)，7.98-8.09(m，2H)，8.21(d，1H，J＝7.70Hz)，8.36(d，1H，J＝7.95Hz). 13C?NMR(CDCl 3，100.61MHz，ppm)δ：13.82，13.85，14.06，14.08，22.59，22.61，22.63，33.10，26.02，27.11，27.45，28.81，29.24，29.50，31.73，31.86，40.29，43.17，45.06，55.12，108.16，108.80，117.87，118.27，119.77，120.01，121.22，122.91，123.05，123.36，124.40，125.19，125.81，126.83，126.98，127.11，127.63，135.69，135.91，139.42，140.66，140.75，141.31，151.00，151.47.Anal.Calcd?for?C 63H 74N 2：C，88.06；H，8.68；N，3.26.Found：C，88.44；H，8.77；N，3.17.
Embodiment 3;
Adopt luminescent material 5 of the present invention, 11-di-n-octyl-6-(4-triphen amido) styryl-indoles [3,2-b] carbazoles (I-2) are manufactured with organic electroluminescence devices:
At first, clean ito glass, use washing lotion (the special-purpose washing lotion of ito glass) to the ito glass ultrasonic cleaning earlier, and then use flushing with clean water, then, use a large amount of clear water ultrasonic irrigation ito glasses more again with the ultrasonic ito glass of washing of washing lotion, then successively with acetone, Virahol is ultrasonic washes, the substrate of cleaning dries up with nitrogen again, uses ultraviolet ray-ozonize 25 minutes with its surface of abundant cleaning at last.
According to the structure of the designed device thick hole mobile material of evaporation 30nm: N on the ITO substrate successively in order, N '-phenylbenzene-N, N '-two (1-naphthyl)-1,1 '-biphenyl-4,4 '-diamines (NPB); The thick luminescent material of the present invention 5 of evaporation 40nm then, 11-di-n-octyl-6-(4-triphen amido) styryl-indoles [3,2-b] carbazoles (I-2) are as luminescent layer; Then evaporation 40nm thick 1,3,5-three (N-phenyl-2-benzoglyoxaline) benzene (TPBI) is as electron transfer layer and hole blocking layer, the aluminium (Al) that thick lithium fluoride of evaporation 1nm (LiF) and 80nm are thick successively is as the negative electrode of device at last.Whole evaporate process is all in high vacuum (～10 -6Torr) carry out under the environment, the evaporation rate of organic layer is controlled at 0.2～0.3nm/s, and the evaporation rate of metal level is controlled at 0.5～0.7nm/s.The thickness of film and sedimentation rate are all monitored and are detected by quartz resonator.Galvanic positive pole is added on the ITO layer, negative pole is added on the LiF/Al layer, promptly launch bright uniform green glow from the ITO layer, glow peak is at 502nm, peak width at half height is 70nm, and the CIE coordinate is (0.224,0.562), trigger voltage 2.6V, when voltage is 14.5V, reach high-high brightness, be 51522cd/m 2, maximum current efficient is 6.00cd/A, maximum lumen efficient is 6.76lm/W.The electroluminescent device result shows that luminescent material of the present invention has outstanding electroluminescent properties.
Embodiment 4:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 1-R 2, R 4-R 6, R 8Be hydrogen atom, R 3, R 7Be n-octyl, it has following structure:
Figure C20071011464100171
Embodiment 5:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 1-R 2, R 4-R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 8Be 9 ', 9-two (normal-butyl) fluorenes, it has following structure:
Figure C20071011464100181
Embodiment 6:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 1-R 2, R 4-R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 8Be N-butyl carbazole, it has following structure:
Figure C20071011464100182
Embodiment 7:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 1-R 2, R 4-R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 8Be triphenylamine, it has following structure:
Embodiment 8:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 1-R 2, R 4-R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 8Be naphthalene, it has following structure:
Figure C20071011464100184
Embodiment 9:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 1-R 2, R 4-R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 8Be pyrene, it has following structure:
Figure C20071011464100191
Embodiment 10:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 2, R 4, R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 1, R 5, R 8Be 9 ', 9-two (normal-butyl) fluorenes, it has following structure:
Figure C20071011464100192
Embodiment 11:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 2, R 4, R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 1, R 5Be 9 ', 9-two (normal-butyl) fluorenes, R 8Be triphenylamine, it has following structure:
Figure C20071011464100193
Embodiment 12:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 2, R 4, R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 1, R 5Be 9 ', 9-two (normal-butyl) fluorenes, R 8Be N-butyl carbazole, it has following structure:
Figure C20071011464100201
Embodiment 13:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 2, R 4, R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 1, R 5Be 9 ', 9-two (normal-butyl) fluorenes, R 8Be naphthalene, it has following structure:
Figure C20071011464100202
Embodiment 14:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 2, R 4, R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 1, R 5Be 9 ', 9-two (normal-butyl) fluorenes, R 8Be pyrene, it has following structure:
Figure C20071011464100203
Embodiment 15:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 2, R 4, R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 1, R 5Be triphenylamine, R 8Be 9 ', 9-two (normal-butyl) fluorenes, it has following structure:
Embodiment 16:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 2, R 4, R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 1, R 5, R 8Be triphenylamine, it has following structure:
Figure C20071011464100212
Embodiment 17:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 2, R 4, R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 1, R 5Be triphenylamine, R 8Be N-butyl carbazole, it has following structure:
Figure C20071011464100213
Embodiment 18:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 2, R 4, R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 1, R 5Be triphenylamine, R 8Be naphthalene, it has following structure:
Embodiment 19:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 2, R 4, R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 1, R 5Be triphenylamine, R 8Be pyrene, it has following structure:
Embodiment 20:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 2, R 4, R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 1, R 5Be N-butyl carbazole, R 8Be 9 ', 9-two (normal-butyl) fluorenes, it has following structure:
Figure C20071011464100222
Embodiment 21:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 2, R 4, R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 1, R 5Be N-butyl carbazole, R 8Be triphenylamine, it has following structure:
Figure C20071011464100223
Embodiment 22:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 2, R 4, R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 1, R 5, R 8Be N-butyl carbazole, it has following structure:
Figure C20071011464100231
Embodiment 23:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 2, R 4, R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 1, R 5Be N-butyl carbazole, R 8Be naphthalene, it has following structure:
Embodiment 24:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 2, R 4, R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 1, R 5Be N-butyl carbazole, R 8Be pyrene, it has following structure:
Figure C20071011464100233
Embodiment 25:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 2, R 4, R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 1, R 5Be pyrene, R 8Be 9 ', 9-two (normal-butyl) fluorenes, it has following structure:
Figure C20071011464100234
Embodiment 26:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 2, R 4, R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 1, R 5Be pyrene, R 8Be triphenylamine, it has following structure:
Figure C20071011464100241
Embodiment 27:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 2, R 4, R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 1, R 5Be pyrene, R 8Be N-butyl carbazole, it has following structure:
Figure C20071011464100242
Embodiment 28:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 2, R 4, R 6Be hydrogen atom, R 3, R 7Be n-octyl, R 1, R 5, R 8Be pyrene, it has following structure:
Embodiment 29:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 1, R 4, R 5Be hydrogen atom, R 3, R 7Be n-octyl, R 2, R 6, R 8Be 9 ', 9-two (normal-butyl) fluorenes, it has following structure:
Figure C20071011464100251
Embodiment 30:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 1, R 4, R 5Be hydrogen atom, R 3, R 7Be n-octyl, R 2, R 6, R 8Be triphenylamine, it has following structure:
Figure C20071011464100252
Embodiment 31:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 1, R 4, R 5Be hydrogen atom, R 3, R 7Be n-octyl, R 2, R 6, R 8Be N-butyl carbazole, it has following structure:
Figure C20071011464100253
Embodiment 32:
A kind of indoles [3,2-b] carbazole derivative organic electroluminescent material, wherein said R 1, R 4, R 5Be hydrogen atom, R 3, R 7Be n-octyl, R 2, R 6, R 8Be pyrene, it has following structure:
Figure C20071011464100261
Although describe the present invention in conjunction with the preferred embodiments, but the present invention is not limited to the foregoing description, be to be understood that, claims have been summarized scope of the present invention, under the guiding of the present invention's design, it should be appreciated by one skilled in the art that the certain change to the various embodiments of the present invention scheme is carried out all will be covered by the spirit and scope of claims of the present invention.

Claims (2)

1, a kind of indoles [3,2-b] carbazole derivative organic electroluminescent compound, structural formula is as follows:
Figure C2007101146410002C1
2, in the claim 1 indoles [3,2-b] carbazole derivative organic electroluminescent compound in the organic electroluminescence device that the multilayer organic materials is formed carrier blocking layers or the application in the luminescent layer.
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