CN104672230A - Arylamino-containing fluorene type derivative and application thereof in electroluminescent device - Google Patents
Arylamino-containing fluorene type derivative and application thereof in electroluminescent device Download PDFInfo
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Abstract
The invention provides an arylamino-containing fluorene type derivative. The arylamino-containing fluorene type derivative has the structure as shown in a formula (1), wherein Ar is selected from fluorenylidene or indenylidenofluorenyl; R1 and R2 are independently selected from one of H, C1-12 aliphatic alkyl, C1-12 aliphatic cycloalkyl, C6-30 aryl, C6-30 heterocyclic aryl and triarylamine; Ar1 and Ar2 are respectively and independently selected from C1-12 aliphatic alkyl, C1-12 aliphatic cycloalkyl or C6-30 aryl; L1 and L2 are respectively and independently selected from a single bond, C1-20 alkylene, substituted or unsubstituted C6-30 arylene and subsituted or unsubstituted C6-30 heteroarylene; and the premise is that R1 and R2 are not H at the same time. The compound has stable nature, the preparation process is simple, and when the compound is used as a phosphorescent host material in an electroluminescent device, the device shows relatively high luminous efficiency and relatively low turn-on voltage. The formula is as described in the specification.
Description
Technical field
The present invention relates to a kind of novel organic compound, and the application in ORGANIC ELECTROLUMINESCENCE DISPLAYS technical field.
Background technology
Electroluminescent material and device, through years of researches and development, have reached practical level, various material, such as hole material, electronic material, luminescent material, and display device technology of preparing has achieved considerable progress.Along with the requirement deeply with to material in practical process of research work, day by day obvious as the advantage of luminescent material with phosphorescence.The luminous efficiency of phosphor material, higher than fluorescent material 3 to 4 times, concerning many display products requiring brightness higher, is primary selection with phosphor material.Phosphorescence luminescent layer in device is steamed altogether by two class materials and is formed, and a class is material of main part, accounts for about 90% of common steaming component, and another kind of is phosphorescent coloring, accounts for about 10% of common steaming component.What tradition used is 4 at phosphorescent light body material, 4 '-N, N '-two carbazole biphenyl.This material has higher triplet, can mate well with phosphorescent coloring, but due to this material molecule amount less (molecular weight 484), make second-order transition temperature lower (Tg be about 1100C or once), in the easy crystallization of use procedure, form island, cause not bright spot, device lifetime shortens.The R and D of new phosphorescent light body material are operated in and constantly carry out, wherein there is the research patent (application number 200680047266.5 introduced by pyridyl in material structure, publication number CN101331626A), also the research patent (application number 200580014777.2 introduced by pyrimidyl in material structure is had, publication number CN1951155A), obtain good improvement effect all in various degree.
Therefore, based on existing research, the phosphorescent light body material of exploitation stability and high efficiency further, thus reduced bright voltage, improve device efficiency, there is very important actual application value.
Summary of the invention
The object of the invention is to propose a kind of novel cpd, this compounds may be used for ORGANIC ELECTROLUMINESCENCE DISPLAYS field, phosphorescent light body material is used as in organic luminescence function layer in organic electroluminescent device, and then it is low to obtain driving voltage, the organic electroluminescence device that current efficiency is high, the transformation period is longer.
For solving the problems of the technologies described above, the technical solution adopted in the present invention is as follows:
Provided by the invention containing imidazo ［ 1, 2, a ］ phosphorescent light body material of pyridine groups and triarylamine, there is higher molecular weight, be conducive to the raising of second-order transition temperature, simultaneously, imidazo [1, 2, a] pyridine groups and carbazole group pass through fluorenylidene, the fused ring aryl groups such as Ya Yin And fluorenyl are connected, each substituting group on this compound is in on-plane surface state, make whole molecule on space multistory, form distortion to a certain extent, the stereoeffect irregularity of molecule, be conducive to forming unformed film, particularly on the basis that triarylamine exists, the present invention introduces imidazo ［ 1, 2, a ］ pyridine groups, effectively have adjusted the triplet (T1) of material.When material of the present invention is used for electroluminescent device as phosphorescence host time, electroluminescent improves significantly at everyways such as opening bright voltage, brightness, work-ing life.
For this reason, the invention provides a kind of fluorene derivatives containing aryl amine with structure as the formula (1):
Wherein:
Ar is selected from fluorenylidene or sub-indeno fluorenyl;
R
1and R
2separately be selected from H, substituted or unsubstituted heterocyclic aryl that substituted or unsubstituted aryl that substituted or unsubstituted aliphatics cycloalkyl that substituted or unsubstituted aliphatic alkyl that carbonatoms is 1-12, carbonatoms are 1-12, carbonatoms are 6-30, carbonatoms are 6-30, triarylamine one of them;
Ar
1and Ar
2independently be selected from substituted or unsubstituted aliphatic alkyl that carbonatoms is 1-12, substituted or unsubstituted aryl that substituted or unsubstituted aliphatics cycloalkyl that carbonatoms is 1-12 or carbonatoms are 6-30;
L
1and L
2independently be selected from singly-bound, substituted or unsubstituted heteroarylidene that substituted or unsubstituted arylidene that alkylidene group that carbonatoms is 1-20, carbonatoms are 6-30 or carbonatoms are 6-30;
Prerequisite is R
1and R
2be asynchronously H.
Further, structure shown in general formula (4) can directly and the connection of imidazo ［ 1,2, a ］ pyridine groups, or, work as R
1or R
2during for H, shown in general formula (4), structure passes through R
1or R
2being connected with imidazo ［ 1,2, a ］ pyridine groups, is also just succeed in reaching an agreement structure shown in formula (4) to be connected directly between R
1or R
2position on;
Further, described R
1and R
2separately be selected from H, methyl, ethyl, propyl group, normal-butyl, n-pentyl, n-hexyl, phenyl, tolyl, ethylbenzene, xenyl, naphthyl, naphthylphenyl, triarylamine one of them.
In general formula (1), when Ar is not singly-bound, the skeleton structure of Ar is selected from following structure:
Further, described Ar
1and Ar
2separately be selected from phenyl, C1-10 alkyl replace phenyl, xenyl, C1-10 alkyl replace xenyl, naphthyl, C1-10 alkyl replace naphthyl, naphthylphenyl, triarylamine one of them.
Further, described bridge linkage group L
1and L
2independently be selected from singly-bound, phenylene, biphenylene, naphthylidene, pyridylidene one of them.
Further, R is worked as
1or R
2when not being H, described R
1or R
2be selected from following structure:
In order to more clearly demonstrate content of the present invention, lower mask body describes the preferred structure of the compound that the present invention relates to:
The invention provides a kind of fluorene derivatives containing aryl amine that can be applicable in organic electroluminescence device.
Further, the described fluorene derivatives containing aryl amine can be used as phosphorescent light body material in organic electroluminescence device.
Present invention also offers a kind of organic electroluminescence device, comprise substrate, and form anode layer, organic luminescence function layer and cathode layer on the substrate successively; Described organic luminescence function layer comprises hole transmission layer, organic luminous layer and electron transfer layer, and the material of main part of described organic luminous layer is the fluorene derivatives containing aryl amine described in one or more.
Further, in organic electroluminescence device, described luminescent layer is made up of material of main part and luminescent dye, and described luminescent dye is phosphorescent coloring.
The fluorene derivatives containing aryl amine that the present invention develops, preparation technology is simple, easy and this material has good thermostability, have the molecular orbital(MO) and triplet (T1) that match with phosphorescent coloring, be good phosphorescent light body material in organic electroluminescence device.
Accompanying drawing explanation
In order to make content of the present invention more easily be understood, below according to a particular embodiment of the invention and by reference to the accompanying drawings, the present invention is further detailed explanation; The highest occupied molecular orbital(HOMO) (HOMO) of compound, lowest unoccupied molecular orbital (LUMO) and triplet (T1) is tried to achieve respectively by Gaussian03/6-31 method.Wherein:
Fig. 1 is the highest occupied molecular orbital(HOMO) of organic compound 12 of the present invention, and HOMO energy level is-4.773.ev, triplet T1=2.2819ev;
Fig. 2 is the lowest unoccupied molecular orbital of organic compound 12 of the present invention, and lumo energy is-1.477ev.
Specific embodiment
Pyridine derivate used in the present invention, phenyl-bromide all can have been bought in Chemicals market at home for basic chemical industry raw materials such as aldehyde ketone, aryl boric acid derivative, carbazyl boric acid derivatives, all available common organic procedures synthesis of various condensed-nuclei aromatics bromo-derivative, condensed-nuclei aromatics boric acid derivatives.
The synthesis of various intermediate
The synthesis of intermediate 1
2-amino-5-bromopyridine 0.892g(5mmol is added) in the flask of a 50ml, the bromo-2-phenyl acetophenone (6mmol) of 2-of 1.7g, sodium bicarbonate 0.491g(6mmol), Virahol 15ml, return stirring 12hrs, steam except Virahol, add 30ml Virahol and 60ml methylene dichloride, collect organic phase, use pillar layer separation product, sherwood oil and ethyl acetate drip washing, 3:1 proportioning.Obtain 1.17g, 67% productive rate.
The synthesis of intermediate 2
2-amino-4-bromopyridine 0.892g(5mmol is added) in the flask of a 50ml, the bromo-2-phenyl acetophenone (6mmol) of 2-of 1.7g, sodium bicarbonate 0.491g(6mmol), Virahol 15ml, return stirring 12hrs, steam except Virahol, add 30ml Virahol and 60ml methylene dichloride, collect organic phase, use pillar layer separation product, sherwood oil and ethyl acetate drip washing, 3:1 proportioning.Obtain 1.25g, 71.84% productive rate.
The synthesis of intermediate 3
PA 0.471g(5mmol is added) in the flask of a 50ml, the bromo-2-(4-bromophenyl of 2-of 2.13g) methyl phenyl ketone (6mmol), sodium bicarbonate 0.491g(6mmol), Virahol 15ml, return stirring 12hrs, steam except Virahol, add 30ml Virahol and 60ml methylene dichloride, collect organic phase, use pillar layer separation product, sherwood oil and ethyl acetate drip washing, 3:1 proportioning.Obtain 1.31g, 75.3% productive rate.
The synthesis of intermediate 4
Add as PA 0.471g (5mmol) in the flask of a 50ml, the bromo-2-phenyl of 2-(4-bromophenyl) ethyl ketone (6mmol) of 2.13, sodium bicarbonate 0.491g(6mmol), Virahol 15ml, return stirring 12hrs, steam except Virahol, add 30ml Virahol and 60ml methylene dichloride, collect organic phase, use pillar layer separation product, sherwood oil and ethyl acetate drip washing, 3:1 proportioning.Obtain 1.20g, 69% productive rate.
The synthesis of various intermediate boric acid (for intermediate 1, all the other roughly the same)
At one 500 milliliters of there-necked flasks; join magnetic agitation, Ar gas shielded, add 2 of 14.9g; 3-phenylbenzene-6-bromine imidazo ［ 1; 2, a ］ THF of pyridine (molecular weight 348,0.0428mol) and 120ml; be chilled to-78 DEG C; drip the nBuLi(0.05mol of 25ml2M), temperature maintains-78 DEG C always, drips the B (OiPr) of 30ml after stirring 10min-78 DEG C time
3(0.153mol), stir and add dilute acid hydrolysis to room temperature, upper strata is white solid.Filter, separate solid product, water layer is neutralized to neutrality, and extract by ethyl acetate, extracting solution evaporate to dryness, adds diluted alkaline, and withdraw not molten impurity in alkali by ethyl acetate, water layer is neutralized to neutrality, and adularescent solid is separated out, and filters, obtains product.Be total to obtain 11.7g solid product, molecular weight 314, productive rate 86.46%.
Embodiment 1
The synthesis of compound 1
The first step,
At one 500 milliliters of there-necked flasks, join electric stirring, Ar gas shielded; add the pentanoic (molecular weight 169,0.10mol) of 16.9g, the bromo-7-of 2-iodo-9; 9-dimethyl fluorene 44g(molecular weight 398,0.11mol), copper powder 15g(molecular weight 64; 0.234mol); salt of wormwood 41.4g(molecular weight 138,0.3mol), 18-hat-6 6.13g(molecular weight 264; 0.023mol), solvent orthodichlorobenzene 300ml is altogether added.Return stirring 4 hours, with TLC monitoring reaction.After reacting completely, be naturally stirred to room temperature, steaming desolventizes.Solid mixture silica gel column chromatography is separated, and obtains micro-yellow monobromo intermediate 40.3g, molecular weight 439, purity 97.5%, productive rate 89.4%.
Second step,
1000 milliliters of there-necked flasks, join magnetic agitation, add 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid 9.42g(molecular weight 314,0.03mol), the monobromo intermediate 12.3g(molecular weight 437,0.028mol obtained in the first step), Pd (PPh
3)
4usage quantity 1.8g(molecular weight 1154,0.00155mol), sodium carbonate 175ml(2M), toluene 175ml, ethanol 175ml.After argon replaces, backflow, with TLC monitoring reaction, react completely after 4 hours, cooling, separate organic layer, evaporate to dryness, the ethyl acetate/petroleum ether with 1/10 carries out post separation, obtains the compound 1 of 14.31g, molecular weight 627, purity 98.5%, productive rate 74.5%.
Product MS(m/e): 629, ultimate analysis (C
46h
35n
3): theoretical value C:87.73%, H:5.60%, N:6.67%; Measured value C:87.75%, H:5.62%, N:6.63%.
Embodiment 2
The synthesis of compound 2
Building-up process divides work two step.The first step reaction be same as embodiment 1 the first step, with 1-naphtyl phenyl amine replace pentanoic make raw material, other reagent and process constant, obtain corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, replaces the monobromo intermediate in embodiment 1 with the monobromo intermediate of the synthesis of the first step here, other reagent and process constant, obtain compound 2.
Product MS(m/e): 679, ultimate analysis (C
50h
37n
3): theoretical value C:88.33%, H:5.49%, N:6.18%; Measured value C:88.30%, H:5.48%, N:6.22%.
Embodiment 3
The synthesis of compound 3
Building-up process divides work two step.The first step reaction is same as embodiment 1 the first step, obtains corresponding monobromo intermediate; Second step reaction is same as embodiment 1 the 2nd step, the monobromo intermediate in embodiment 1 is replaced with the monobromo intermediate of the first step synthesis, with 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-7-boric acid replacement 2,3-diphenyl-imidazole is ［ 1,2, a ］ pyridine-6-boric acid also, other reagent and process constant, obtain compound 3.
Product MS(m/e): 629, ultimate analysis (C
46h
35n
3): theoretical value C:87.73%, H:5.60%, N:6.67%; Measured value C:87.70%, H:5.61%, N:6.69%.
Embodiment 4
The synthesis of compound 4
Building-up process divides work two step.The first step reaction be same as embodiment 1 the first step, with 1-naphtyl phenyl amine replace pentanoic make raw material, other reagent and process constant, obtain corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, the monobromo intermediate in embodiment 1 is replaced with the monobromo intermediate of the first step synthesis, with 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-7-boric acid replacement 2,3-diphenyl-imidazole is ［ 1,2, a ］ pyridine-6-boric acid also, other reagent and process constant, obtain compound 4.
Product MS(m/e): 679, ultimate analysis (C
50h
37n
3): theoretical value C:88.33%, H:5.49%, N:6.18%; Measured value C:88.31%, H:5.46%, N:6.23%.
Embodiment 5
The synthesis of compound 5
Building-up process divides work two step.The first step reaction is same as embodiment 1 the first step, obtains corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, the monobromo intermediate in embodiment 1 is replaced with the monobromo intermediate of the first step synthesis, with 4-(3-phenylimidazole also ［ 1,2, a ］ pyridine-2-base) phenylo boric acid replaces 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid, other reagent and process constant, obtain compound 5.
Product MS(m/e): 629, ultimate analysis (C
46h
35n
3): theoretical value C:87.73%, H:5.60%, N:6.67%; Measured value C:87.75%, H:5.61%, N:6.64%.
Embodiment 6
The synthesis of compound 6
Building-up process divides work two step.The first step reaction be same as embodiment 1 the first step, with 1-naphtyl phenyl amine replace pentanoic make raw material, other reagent and process constant, obtain corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, the monobromo intermediate in embodiment 1 is replaced with the monobromo intermediate of the first step synthesis, with 4-(3-phenylimidazole also ［ 1,2, a ］ pyridine-2-base) phenylo boric acid replaces 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid, other reagent and process constant, obtain compound 6.
Product MS(m/e): 679, ultimate analysis (C
50h
37n
3): theoretical value C:88.33%, H:5.49%, N:6.18%; Measured value C:88.34%, H:5.45%, N:6.21%.
Embodiment 7
The synthesis of compound 7
Building-up process divides work two step.The first step reaction is same as embodiment 1 the first step, obtains corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, the monobromo intermediate in embodiment 1 is replaced with the monobromo intermediate of the first step synthesis, with 4-(2-phenylimidazole also ［ 1,2, a ］ pyridin-3-yl) phenylo boric acid replaces 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid, other reagent and process constant, obtain compound 7.
Product MS(m/e): 629, ultimate analysis (C
46h
35n
3): theoretical value C:87.73%, H:5.60%, N:6.67%; Measured value C:87.74%, H:5.63%, N:6.63%.
Embodiment 8
The synthesis of compound 8
Building-up process divides work two step.The first step reaction be same as embodiment 1 the first step, with 1-naphtyl phenyl amine replace pentanoic make raw material, other reagent and process constant, obtain corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, the monobromo intermediate in embodiment 1 is replaced with the monobromo intermediate of the first step synthesis, with 4-(2-phenylimidazole also ［ 1,2, a ］ pyridin-3-yl) phenylo boric acid replaces 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid, other reagent and process constant, obtain compound 8.
Product MS(m/e): 679, ultimate analysis (C
50h
37n
3): theoretical value C:88.33%, H:5.49%, N:6.18%; Measured value C:88.36%, H:5.50%, N:6.14%.
Embodiment 9
The synthesis of compound 9
Building-up process divides work two step.The first step reaction is same as embodiment 1 the first step, obtains corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, replaces the monobromo intermediate in embodiment 1 with the monobromo intermediate of the first step synthesis, other reagent and process constant, obtain compound 9.
Product MS(m/e): 745, ultimate analysis (C
55h
43n
3): theoretical value C:88.56%, H:5.81%, N:5.63%; Measured value C:88.58%, H:5.83%, N:5.59%.
Embodiment 10
The synthesis of compound 10
Building-up process divides work two step.The first step reaction be same as embodiment 1 the first step, with 1-naphtyl phenyl amine replace pentanoic make raw material, other reagent and process constant, obtain corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, replaces the monobromo intermediate in embodiment 1 with the monobromo intermediate of the first step synthesis, other reagent and process constant, obtain compound 10.
Product MS(m/e): 795, ultimate analysis (C
59h
45n
3): theoretical value C:89.02%, H:5.70%, N:5.28%; Measured value C:89.06%, H:5.71%, N:5.23%.
Embodiment 11
The synthesis of compound 11
Building-up process divides work two step.The first step reaction is same as embodiment 1 the first step, obtains corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, the monobromo intermediate in embodiment 1 is replaced with the monobromo intermediate of the first step synthesis, with 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-7-boric acid replacement 2,3-diphenyl-imidazole is ［ 1,2, a ］ pyridine-6-boric acid also, other reagent and process constant, obtain compound 11.
Product MS(m/e): 745, ultimate analysis (C
55h
43n
3): theoretical value C:88.56%, H:
5.81%, N:5.63%; Measured value C:88.53%, H:5.80%, N:5.67%.
Embodiment 12
The synthesis of compound 12
Building-up process divides work two step.The first step reaction be same as embodiment 1 the first step, with 1-naphtyl phenyl amine replace pentanoic make raw material, other reagent and process constant, obtain corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, the monobromo intermediate in embodiment 1 is replaced with the monobromo intermediate of the first step synthesis, with 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-7-boric acid replacement 2,3-diphenyl-imidazole is ［ 1,2, a ］ pyridine-6-boric acid also, other reagent and process constant, obtain compound 12.
Product MS(m/e): 795, ultimate analysis (C
59h
45n
3): theoretical value C:89.02%, H:5.70%, N:5.28%; Measured value C:89.00%, H:5.64%, N:5.36%.
Embodiment 13
The synthesis of compound 13
Building-up process divides work two step.The first step reaction is same as embodiment 1 the first step, obtains corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, the monobromo intermediate in embodiment 1 is replaced with the monobromo intermediate of the first step synthesis, with 4-(3-phenylimidazole also ［ 1,2, a ］ pyridine-2-base) phenylo boric acid replaces 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid, other reagent and process constant, obtain compound 13.
Product MS(m/e): 745, ultimate analysis (C
55h
43n
3): theoretical value C:88.56%, H:5.81%, N:5.63%; Measured value C:88.52%, H:5.80%, N:5.68%.
Embodiment 14
The synthesis of compound 14
Building-up process divides work two step.The first step reaction be same as embodiment 1 the first step, with 1-naphtyl phenyl amine replace pentanoic make raw material, other reagent and process constant, obtain corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, the monobromo intermediate in embodiment 1 is replaced with the monobromo intermediate of the first step synthesis, with 4-(3-phenylimidazole also ［ 1,2, a ］ pyridine-2-base) phenylo boric acid replaces 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid, other reagent and process constant, obtain compound 14.
Product MS(m/e): 795, ultimate analysis (C
59h
45n
3): theoretical value C:89.02%, H:5.70%, N:5.28%; Measured value C:89.05%, H:5.68%, N:5.27%.
Embodiment 15
The synthesis of compound 15
Building-up process divides work two step.The first step reaction is same as embodiment 1 the first step, obtains corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, the monobromo intermediate in embodiment 1 is replaced with the monobromo intermediate of the first step synthesis, with 4-(2-phenylimidazole also ［ 1,2, a ］ pyridin-3-yl) phenylo boric acid replaces 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid, other reagent and process constant, obtain compound 15.
Product MS(m/e): 745, ultimate analysis (C
55h
43n
3): theoretical value C:88.56%, H:5.81%, N:5.63%; Measured value C:88.58%, H:5.83%, N:5.59%.
Embodiment 16
The synthesis of compound 16
Building-up process divides work two step.The first step reaction be same as embodiment 1 the first step, with 1-naphtyl phenyl amine replace pentanoic make raw material, other reagent and process constant, obtain corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, the monobromo intermediate in embodiment 1 is replaced with the monobromo intermediate of the first step synthesis, with 4-(2-phenylimidazole also ［ 1,2, a ］ pyridin-3-yl) phenylo boric acid replaces 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid, other reagent and process constant, obtain compound 16.
Product MS(m/e): 795, ultimate analysis (C
59h
45n
3): theoretical value C:89.02%, H:5.70%, N:5.28%; Measured value C:89.01%, H:5.69%, N:5.30%.
Embodiment 17
The synthesis of compound 17
Building-up process divides work two step.The first step reaction is same as embodiment 1 second step, with the iodo-tetramethyl-indeno ［ 3 of the bromo-7-of 2-, 2, b ］ iodo-9, the 9-dimethyl fluorenes of the fluorenes replacement bromo-7-of 2-, 2 are replaced with triphenylamine-4-boric acid, 3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid makes raw material, other reagent and process constant, obtain corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, replaces the monobromo intermediate in embodiment 1 with the monobromo intermediate of the first step synthesis, other reagent and process constant, obtain compound 17.
Product MS(m/e): 821, ultimate analysis (C
61h
47n
3): theoretical value C:89.13%, H:5.76%, N:5.11%; Measured value C:89.15%, H:5.73%, N:5.12%.
Embodiment 18
The synthesis of compound 18
Building-up process divides work two step.The first step reaction is same as embodiment 1 second step, with the iodo-tetramethyl-indeno ［ 3 of the bromo-7-of 2-, 2, b ］ iodo-9, the 9-dimethyl fluorenes of the fluorenes replacement bromo-7-of 2-, 2 are replaced with triphenylamine-4-boric acid, 3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid makes raw material, other reagent and process constant, obtain corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, replaces the monobromo intermediate in embodiment 1, with 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-7-with the monobromo intermediate of the first step synthesis
Boric acid replaces 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid, other reagent and process constant, obtain compound 18.
Product MS(m/e): 821, ultimate analysis (C
61h
47n
3): theoretical value C:89.13%, H:5.76%, N:5.11%; Measured value C:89.11%, H:5.74%, N:5.15%.
Embodiment 19
The synthesis of compound 19
Building-up process divides work two step.The first step reaction is same as embodiment 1 second step, with the iodo-tetramethyl-indeno ［ 3 of the bromo-7-of 2-, 2, b ］ iodo-9, the 9-dimethyl fluorenes of the fluorenes replacement bromo-7-of 2-, 2 are replaced with triphenylamine-4-boric acid, 3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid makes raw material, other reagent and process constant, obtain corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, the monobromo intermediate in embodiment 1 is replaced with the monobromo intermediate of the first step synthesis, with 4-(3-phenylimidazole also ［ 1,2, a ］ pyridine-2-base) phenylo boric acid replaces 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid, other reagent and process constant, obtain compound 19.
Product MS(m/e): 821, ultimate analysis (C
61h
47n
3): theoretical value C:89.13%, H:5.76%, N:5.11%; Measured value C:89.10%, H:5.72%, N:5.18%.
Embodiment 20
The synthesis of compound 20
Building-up process divides work two step.The first step reaction is same as embodiment 1 second step, with the iodo-tetramethyl-indeno ［ 3 of the bromo-7-of 2-, 2, b ］ iodo-9, the 9-dimethyl fluorenes of the fluorenes replacement bromo-7-of 2-, 2 are replaced with triphenylamine-4-boric acid, 3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid makes raw material, other reagent and process constant, obtain corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, the monobromo intermediate in embodiment 1 is replaced with the monobromo intermediate of the first step synthesis, with 4-(3-phenylimidazole also ［ 1,2, a ］ pyridine-2-base) phenylo boric acid replaces 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid, other reagent and process constant, obtain compound 20.
Product MS(m/e): 821, ultimate analysis (C
61h
47n
3): theoretical value C:89.13%, H:5.76%, N:5.11%; Measured value C:89.16%, H:5.77%, N:5.07%.
Embodiment 21
The synthesis of compound 21
Building-up process divides work two step.The first step reaction is same as embodiment 1 second step, the bromo-7-of 2-iodo-9 is replaced with the bromo-7-of 2-iodo-tetramethyl-indeno ［ 3,2, b ］ fluorenes, 9-dimethyl fluorene, with 4 ', 4 '-dimethyltrianiline-4-boric acid replaces 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid makes raw material, other reagent and process constant, obtain corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, the monobromo intermediate in embodiment 1 is replaced with the monobromo intermediate of the first step synthesis, with 4-(3-phenylimidazole also ［ 1,2, a ］ pyridine-2-base) phenylo boric acid replaces 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid, other reagent and process constant, obtain compound 21.
Product MS(m/e): 849, ultimate analysis (C
63h
51n
3): theoretical value C:89.01%, H:6.05%, N:4.94%; Measured value C:89.03%, H:6.07%, N:4.90%.
Embodiment 22
The synthesis of compound 22
Building-up process divides work two step.The first step reaction is same as embodiment 1 second step, the bromo-7-of 2-iodo-9 is replaced with the bromo-7-of 2-iodo-tetramethyl-indeno ［ 3,2, b ］ fluorenes, 9-dimethyl fluorene, with 4 ', 4 '-dimethyltrianiline-4-boric acid replaces 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid makes raw material, other reagent and process constant, obtain corresponding monobromo intermediate; Second step reaction is same as embodiment 1 second step, the monobromo intermediate in embodiment 1 is replaced with the monobromo intermediate of the first step synthesis, with 4-(2-phenylimidazole also ［ 1,2, a ］ pyridin-3-yl) phenylo boric acid replaces 2,3-diphenyl-imidazole also ［ 1,2, a ］ pyridine-6-boric acid, other reagent and process constant, obtain compound 22.
Product MS(m/e): 849, ultimate analysis (C
63h
51n
3): theoretical value C:89.01%, H:6.05%, N:4.94%; Measured value C:89.02%, H:6.03%, N:4.95%.
Here is the Application Example of the compounds of this invention:
Embodiment 23: the preparation of electroluminescent device and result
The preferred implementation of fabricate devices:
(1) device layout
Conveniently compare the performance of these materials, the present invention devises a simple electroluminescent device (substrate/anode/hole transmission layer (HTL)/phosphorescent coloring/phosphorescence host (EL)/electron transfer layer (ETL)/negative electrode), only use compound 1,4,5,8,10,13,15,18,22 as phosphorescent light body material illustration, CBP or NPB or mCP as phosphorescence host comparative material, Ir(ppy)
3, Ir (piq)
3with Firpic respectively as phosphorescent coloring.The structure of CBP and phosphorescent coloring is:
Substrate can use the substrate in conventional organic luminescence device, such as: glass or plastics.In element manufacturing of the present invention, select glass substrate, ITO makes anode material.
Hole transmission layer can adopt various tri-arylamine group material.Hole mobile material selected in element manufacturing of the present invention is NPB.
Electron transport material selected in element manufacturing of the present invention is Bphen.
Negative electrode can adopt metal and composition thereof structure, as Mg:Ag, Ca:Ag etc., can be also electron injecting layer/metal-layer structure, as LiF/Al, Li
2the common cathode structures such as O/Al.Electron injection material selected in element manufacturing of the present invention is LiF, and cathode material is Al.
(2) element manufacturing
Sheet glass supersound process in commercial detergent of ITO transparency conducting layer will be coated with; rinse in deionized water, at acetone: ultrasonic oil removing in alcohol mixed solvent, be baked under clean environment and remove moisture content completely; by UV-light and ozone clean, and with low energy positively charged ion bundle bombarded surface;
The above-mentioned glass substrate with anode is placed in vacuum chamber, is evacuated to 1 × 10
-5~ 9 × 10
-3pa, on above-mentioned anode tunic, vacuum evaporation NPB is as hole transmission layer, and evaporation rate is 0.1nm/s, and evaporation thickness is 40nm;
Vacuum evaporation phosphorescent light body material 1,4,5,8,10,13,15,18,22 of the present invention on hole transmission layer, is total to evaporation phosphorescent coloring Ir(ppy simultaneously)
3(or FIrpic, or Ir(piq)
3), phosphorescent light body material also can replace with CBP or NPB or mCP.Phosphorescence host and dyestuff are total to the luminescent layer of evaporation as device, evaporation rate is 0.1nm/s, evaporation total film thickness is 30nm, luminescent dye Ir(ppy) 3 doping content be 10%, the doping content of FIrpic is 12%, Ir(piq) doping content of 3 is 5%, doping content mentioned here refers to that the evaporation rate ratio of luminescent dye and material of main part is 10:100,12:100,5:100;
On luminescent layer, vacuum evaporation one deck compd B phen is as the electron transfer layer of device, and its evaporation rate is 0.1nm/s, and evaporation total film thickness is 20nm;
At the upper vacuum evaporation LiF of electron transfer layer (ETL) as electron injecting layer, thickness 0.5nm.On LiF layer, evaporating Al layer is as the negative electrode of device, and thickness is 150nm.
Device performance sees the following form (device architecture: ITO/NPB(40nm)/phosphorescent coloring/phosphorescence host (30nm)/Bphen(20nm)/LiF(0.5nm)/Al(150nm))
| Luminescent layer | Require brightness cd/m 2 | Voltage V | Current density A/m 2 | Current efficiency cd/A | Glow color |
| CBP:Ir(ppy)3 | 1000 | 4.1 | 31.25 | 32.2 | Green glow |
| 1:Ir(ppy)3 | 1000 | 3.6 | 28.01 | 35.7 | Green glow |
| 4:Ir(ppy)3 | 1000 | 3.7 | 27.62 | 36.2 | Green glow |
| 5:Ir(ppy)3 | 1000 | 3.6 | 27.85 | 35.9 | Green glow |
| 8:Ir(ppy)3 | 1000 | 3.8 | 26.38 | 37.9 | Green glow |
| NPB:Ir(piq)3 | 1000 | 4.5 | 140.84 | 7.1 | Ruddiness |
| 10:Ir(piq)3 | 1000 | 4.2 | 123.45 | 8.1 | Ruddiness |
| 13:Ir(piq)3 | 1000 | 4.3 | 128.20 | 7.8 | Ruddiness |
| 15:Ir(piq)3 | 1000 | 4.3 | 131.57 | 7.6 | Ruddiness |
| mCP:FIrpic | 1000 | 4.7 | 68.49 | 14.6 | Blue light |
| 18:FIrpic | 1000 | 4.6 | 64.93 | 15.4 | Blue light |
| 22:FIrpic | 1000 | 4.5 | 65.78 | 15.2 | Blue light |
Above result shows, new organic materials of the present invention is used for organic electroluminescence device, can effectively reduce landing voltage, and improving current efficiency, is phosphorescence host of good performance.
Although describe the present invention in conjunction with the embodiments, the present invention is not limited to above-described embodiment, should be appreciated that, under the guiding of the present invention's design, those skilled in the art can carry out various amendment and improvement, and claims summarise scope of the present invention.
Claims (11)
1., containing a fluorene derivatives for aryl amine, it is characterized in that there is structure as the formula (1):
Wherein:
Ar is selected from fluorenylidene or sub-indeno fluorenyl;
R
1and R
2separately be selected from H, substituted or unsubstituted heterocyclic aryl that substituted or unsubstituted aryl that substituted or unsubstituted aliphatics cycloalkyl that substituted or unsubstituted aliphatic alkyl that carbonatoms is 1-12, carbonatoms are 1-12, carbonatoms are 6-30, carbonatoms are 6-30, triarylamine one of them;
Ar
1and Ar
2independently be selected from substituted or unsubstituted aliphatic alkyl that carbonatoms is 1-12, substituted or unsubstituted aryl that substituted or unsubstituted aliphatics cycloalkyl that carbonatoms is 1-12 or carbonatoms are 6-30;
L
1and L
2independently be selected from singly-bound, substituted or unsubstituted heteroarylidene that substituted or unsubstituted arylidene that alkylidene group that carbonatoms is 1-20, carbonatoms are 6-30 or carbonatoms are 6-30;
Prerequisite is R
1and R
2be asynchronously H.
2. imidazopyridine derivatives according to claim 1, is characterized in that, described R
1and R
2separately be selected from H, methyl, ethyl, propyl group, normal-butyl, n-pentyl, n-hexyl, phenyl, tolyl, ethylbenzene, xenyl, naphthyl, naphthylphenyl, triarylamine one of them.
3. the fluorene derivatives containing aryl amine according to claim 1, it is characterized in that, when Ar is not singly-bound, the skeleton structure of Ar is selected from following structure:
4. the fluorene derivatives containing aryl amine according to claim 1, is characterized in that, described in
Ar
1and Ar
2separately be selected from phenyl, C1-10 alkyl replace phenyl, xenyl, C1-10 alkyl replace xenyl, naphthyl, C1-10 alkyl replace naphthyl, naphthylphenyl, triarylamine one of them.
5. the fluorene derivatives containing aryl amine according to claim 1, is characterized in that, described bridge linkage group L
1and L
2independently be selected from singly-bound, phenylene, biphenylene, naphthylidene, pyridylidene one of them.
6. the fluorene derivatives containing aryl amine according to claim 1, is characterized in that, work as R
1or R
2when not being H, described R
1or R
2be selected from following structure
7. the fluorene derivatives containing aryl amine according to claim 1, it is characterized in that, described organic compound is selected from following structural formula:
8. the organic compound described in any one of claim 1-7, is applied in organic electroluminescence device.
9. a kind of organic compound being applied to organic electroluminescence device according to claim 8, is characterized in that, can be used as phosphorescent light body material.
10. an organic electroluminescence device, comprises substrate, and forms anode layer, organic luminescence function layer and cathode layer on the substrate successively; Described organic luminescence function layer comprises hole transmission layer, organic luminous layer and electron transfer layer, it is characterized in that:
The material of main part of described organic luminous layer is one or more organic compound according to any one of claim 1-7.
11. a kind of organic electroluminescence devices according to claim 10, it is characterized in that, described luminescent layer is made up of material of main part and luminescent dye, and described luminescent dye is phosphorescent coloring.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106905221A (en) * | 2017-03-04 | 2017-06-30 | 长春海谱润斯科技有限公司 | A kind of benzo fluorene kind derivative and its organic luminescent device |
| CN107383003A (en) * | 2017-06-15 | 2017-11-24 | 浙江工业大学 | A kind of synthesis and application of the tri-arylamine group dye sensitizing agent containing quinacridone |
| CN112830925A (en) * | 2019-11-25 | 2021-05-25 | 广东阿格蕾雅光电材料有限公司 | Compound and organic electroluminescent device containing same |
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|---|---|---|---|---|
| KR20110079402A (en) * | 2009-12-31 | 2011-07-07 | (주)씨에스엘쏠라 | Organic light device and organic light compound for the same |
| WO2012108879A1 (en) * | 2011-02-11 | 2012-08-16 | Universal Display Corporation | Organic light emitting device and materials for use in same |
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2013
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20110079402A (en) * | 2009-12-31 | 2011-07-07 | (주)씨에스엘쏠라 | Organic light device and organic light compound for the same |
| WO2012108879A1 (en) * | 2011-02-11 | 2012-08-16 | Universal Display Corporation | Organic light emitting device and materials for use in same |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106905221A (en) * | 2017-03-04 | 2017-06-30 | 长春海谱润斯科技有限公司 | A kind of benzo fluorene kind derivative and its organic luminescent device |
| CN107383003A (en) * | 2017-06-15 | 2017-11-24 | 浙江工业大学 | A kind of synthesis and application of the tri-arylamine group dye sensitizing agent containing quinacridone |
| CN107383003B (en) * | 2017-06-15 | 2019-11-29 | 浙江工业大学 | A kind of synthesis and application of the tri-arylamine group dye sensitizing agent containing quinacridone |
| CN112830925A (en) * | 2019-11-25 | 2021-05-25 | 广东阿格蕾雅光电材料有限公司 | Compound and organic electroluminescent device containing same |
| CN112830925B (en) * | 2019-11-25 | 2022-09-02 | 广东阿格蕾雅光电材料有限公司 | Compound and organic electroluminescent device containing same |
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