CN1300140C - Compound of quinacridones-carbazole group and application in organic electroluminescence device - Google Patents
Compound of quinacridones-carbazole group and application in organic electroluminescence device Download PDFInfo
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- CN1300140C CN1300140C CNB200410011335XA CN200410011335A CN1300140C CN 1300140 C CN1300140 C CN 1300140C CN B200410011335X A CNB200410011335X A CN B200410011335XA CN 200410011335 A CN200410011335 A CN 200410011335A CN 1300140 C CN1300140 C CN 1300140C
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- quinacridone
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- carbazole
- carbazolyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 30
- 238000005401 electroluminescence Methods 0.000 title claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims description 10
- 238000000576 coating method Methods 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 238000002347 injection Methods 0.000 claims description 5
- 239000007924 injection Substances 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 7
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 238000005516 engineering process Methods 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 77
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 70
- 239000000047 product Substances 0.000 description 65
- 238000004458 analytical method Methods 0.000 description 59
- 150000001793 charged compounds Chemical class 0.000 description 58
- 238000001819 mass spectrum Methods 0.000 description 58
- 239000000126 substance Substances 0.000 description 58
- 150000001716 carbazoles Chemical class 0.000 description 43
- 239000010410 layer Substances 0.000 description 43
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 40
- 229960003750 ethyl chloride Drugs 0.000 description 40
- 239000000463 material Substances 0.000 description 25
- 230000002194 synthesizing effect Effects 0.000 description 25
- -1 aromatic rings organic compound Chemical class 0.000 description 24
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 18
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 17
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical class CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 14
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 14
- 238000004440 column chromatography Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 12
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 7
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 230000005526 G1 to G0 transition Effects 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
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- 230000008020 evaporation Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
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- 229910052751 metal Inorganic materials 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 2
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 2
- HXFSVGUKGVGASD-UHFFFAOYSA-N 3,6-diethyl-9h-carbazole Chemical compound C1=C(CC)C=C2C3=CC(CC)=CC=C3NC2=C1 HXFSVGUKGVGASD-UHFFFAOYSA-N 0.000 description 2
- 229920003026 Acene Polymers 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 229940055858 aluminum chloride anhydrous Drugs 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 1
- KOFZTCSTGIWCQG-UHFFFAOYSA-N 1-bromotetradecane Chemical class CCCCCCCCCCCCCCBr KOFZTCSTGIWCQG-UHFFFAOYSA-N 0.000 description 1
- XJJWQKGKHQTROG-UHFFFAOYSA-N 2,5-dihydroxycyclohexa-1,4-diene-1,4-dicarboxylic acid Chemical compound OC(=O)C1=C(O)CC(C(O)=O)=C(O)C1 XJJWQKGKHQTROG-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- 206010023126 Jaundice Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001348 alkyl chlorides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
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- 229960005081 diclofenamide Drugs 0.000 description 1
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- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WJXIVKDQSNXDLD-UHFFFAOYSA-N n-naphthalen-1-yloxyaniline Chemical compound C=1C=CC2=CC=CC=C2C=1ONC1=CC=CC=C1 WJXIVKDQSNXDLD-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The present invention relates to quinacridone-carbazole compounds shown as a formula (I) and the application thereof in preparing organic electroluminescent devices. In the formula (I), R1 and R2 can be identical or different, and represent H or alkyl of C1 to C4; R3, R4, R5 and R6 are identical, and represent alkyl of C1 to C11, alkoxyl of C1 to C11, substituted alkyl of C1 to C11, aryl, substituted aryl, aromatic fused rings, substituted aromatic fused rings or halogen; and n is equal to 4 to 18. The quinacridone-carbazole compounds can be used for preparing the electroluminescent devices with one or more active layers, and at least one or more compounds are contained in the active layers which can comprise an optical emission layer and/or a transferring layer and/or an electronic charge injecting layer. The electroluminescent efficiency of the devices is kept in a high level within a wider doping range (0.5 to 5 wt%), so the technology of the devices is easy to repeat, and green luminescent devices can be prepared.
Description
Technical field
The present invention relates to a kind of electroluminescent organic material and application thereof, be specifically related to a kind of quinacridone-carbazole compound and as the application of luminescent material in organic electroluminescence device.
Background technology
The organic electroluminescent phenomenon is found the time of existing three more than ten years, before 1987, because the great drawback (cut-in voltage＞200V), limited its application that organic electroluminescence device exists.Because the continuous breakthrough of material and device technology, organic electroluminescent has been reached or since nearly ten years near the practicability stage.
Nineteen sixty-five Gurnee etc. has delivered the patent (U.S.Pat.No.3,172,862,3,173,050) about organic electroluminescence device first.Dresner in 1973 have also delivered the patent (U.S.Pat.No.3,170,167) of organic electroluminescence device aspect.Many aromatic rings organic compound such as anthracene, four acenes, five acenes etc. are used to electroluminescent organic material in these inventions.Early stage device primary structure is characterized as single layer structure, and the thickness of organic luminous layer is greater than 1mm, and the cut-in voltage of device is more than 200v.
The eighties, the Tang etc. of U.S. Kodak company at first found ultra-thin multilayer device structure, the cut-in voltage of device was reduced greatly (U.S.Pat.No.4,356,429).The essential characteristic of its device is to be substrate with the conductive glass, elder generation's evaporation last layer hole injection layer (100nm), also be transport layer simultaneously, spin coating last layer organic electron transport layer then, also be electroluminescence layer simultaneously, plate layer of metal at last as negative pole, this device cut-in voltage is 20v, and brightness is 5cd/m
2Employing aromatic multi-amine such as the VanSlyke of Kodak company is that hole transmission layer carries out the device preparation afterwards, and device performance is improved greatly, and brightness can reach 340cd/m
2
The VanSlyke and the Tang of U.S. Kodak company at first find Alq
3(oxine aluminium) has after the good electroluminescent properties, and people use oxine and derivative and Al in succession
3+, Zn
2+, Ga
3+, Be
2+Deng having synthesized a series of electroluminescent materials, the most of jaundice of these materials green glows, some blue light-emitting (is seen U.S.Pat.No.4,720,432; U.S.Pat.No.4,539,507; C.W.Tang, S.A.VanSlyke, Appl.Phys.1987,51,913; U.S.Pat.No.5,151,629; Hamada, Jpn.J.Appl.Phys., Part2., 1992,32, L 514; Matsumura, Jpn.J.Appl.Phys., 1996,35,5357; Burrows, J.Appys., 1996,79,7991).The Sano of Japan Sanyo company etc. are at U.S.Pat.5, in 432,014 with the west not alkali-Zn complex prepared blue-light device as luminescent layer.Hamada of it should be noted that Japanese Sanyo company etc. synthesizes 10-hydroxy benzo quinoline compound, and its electroluminescent properties has surpassed Alq
3(Hamadadeng Chem.1ett., 1993,950).
Because the discovery of electroluminescent material and the continuing to optimize of device architecture of some excellent propertys make organic electroluminescent obtain some breakthroughs.(see U.S.Pat.Nos.5,151,629; 5,150,006; 5,141,671; 5,073,446; 5,061,569; 5,059,862; 5,059,861; 5,047,687; 4,950,950; 5,104,740; 5,227,252; 5,256,945; 5,069,957; 5,122,711; 5,554,450; 5,683,823; 5,593,788; 5,645,948; 5,451,343; 5,623,080; 5,395,862).
The Murayama of Japan vanguard electronics corporation etc. has at first prepared electroluminescent device with quinacridone and derivative thereof and (has seen U.S.Pat.No.5,227,252), because used quinacridone derivatives such as Murayama are easy to form intermolecular strong hydrogen bonding, cause the stability of device to have certain problem.The improved quinacridone derivatives of usefulness such as Shi Jianmin of Kodak have prepared electroluminescent device and (have seen U.S.Pat.No.5 afterwards, 593,788), its efficient is 7.31cd/A, the improved quinacridone derivative of this class can be avoided the formation of intermolecular strong hydrogen bonding, and the stability of device is significantly improved.The electroluminescent device of the quinacridone derivative preparation that Murayama etc. and Shi Jianmin etc. are used has obtained the good device of performance, but because used quinacridone derivative luminophor molecule is all assembled than being easier to, therefore must could realize higher efficient under the low doping concentration (less than 1%) very much, can cause fluorescent quenching when concentration is higher, make the requirement of device evaporation process very strict like this, when producing in batches, device technology is required very harshness, therefore seek and to realize that in the broad concentration range high efficiency electroluminous material be a problem that presses for solution.The electroluminescent efficiency of the used quinacridone derivative of Murayama etc. and Shi Jianmin etc. is still waiting further raising in addition.
Carbazole is the important source material of compound probabilities such as dyestuff, pigment, medicine, agricultural chemicals and leaded light, conduction special material.In recent years, many carbazoles system with its stronger cavity transmission ability and preferably luminosity be subjected to extensive concern.Research and application to carbazole compound have significance.
Summary of the invention
The purpose of this invention is to provide a class can realize luminous efficiency height, good stability in the broad concentration range electroluminescent organic material, and the application of this material in organic electroluminescence device.The present invention makes the preparation technology of the electroluminescent device easier repetition that becomes, and is more suitable for the batch suitability for industrialized production of device.
Find that after deliberation quinacridone-carbazole compound has good electroluminescence characters.Of the present invention to liking the represented compounds of general formula (I):
General formula (I) representative is the quinacridone derivative of basic structure skeleton with the quinacridone.R wherein
1And R
2Can be the same or different R
1And R
2Be H or C
1-4Alkyl.R
3, R
4, R
5And R
6Identical, be C
1-C
11Alkyl, C
1-C
11Alkoxyl group, C
1-C
11Substituted alkyl, aromatic base, substituted aromatic base, aromatic condensed ring, substituted aroma condensed ring, halogen; N=4-18.
As the preferable range of The compounds of this invention, R in the formula (1)
1And R
2Be H or C
1-4Alkyl, R
3, R
4, R
5And R
6Be identical C
1-C
6Alkyl, C
1-C
6Alkoxyl group, phenyl, phenyl derivatives, phenylol, phenylol derivative.n＝4-10。
Formula of the present invention (I) is new quinacridone-carbazole compound, be applicable to preparation high performance electroluminescent organic device, the EL efficiency height, electroluminescent efficiency (0.5-5wt%) in the doping scope of broad remains on high level, make the repetition that is easy to of device technology change, help the devices in batches suitability for industrialized production.
For preparation quinacridone-carbazole compound is undertaken by following reaction pattern 1:
Reaction pattern 1:
Owing to have more substituted radical by 1 synthetic quinacridone derivative of reaction pattern, therefore intermolecular be not easy to produce assemble, therefore under higher doping content condition, has very high luminous efficiency, therefore also insensitive with the EL efficiency of these material preparations for the variation of doping content, can under higher doping content, obtain high electroluminescent efficiency.
, with alkyl chloride the Fu Shi alkylated reaction takes place and generate compound (A) under the Aluminum chloride anhydrous existence condition by reaction pattern 1 carbazole.With 2,5-dihydroxyl-1,4-cyclohexadiene-1,4-dicarboxylate and disubstituted benzene amine are raw material, with ethanol is solvent, condensation reaction takes place under the hydrochloric acid existence condition generate compound (B), compound (B) is in chloronaphthalene, cyclization takes place under 260 ℃ of conditions generate compound (C), compound (C) is at oil of mirbane, potassium hydroxide, ethanol, reaction obtains compound (D) in acetate and the ethylene glycol monoemethyl ether mixed solvent, compound (D) is (under the NaH existence condition) and two bromoalkane reacting generating compounds (E) in tetrahydrofuran solution, and compound (E) (under KOH existence condition) in butanone solution reacts with compound (A) and can obtain target compound (I).
Compound of the present invention can be used as electroluminescent material and prepares electroluminescent device, especially can be used for the active coating of electroluminescent device.So-called active coating is exactly can be luminous under certain driving voltage or have that electric charge injects, the organic thin film layer of transmission performance.Therefore object of the present invention also is formula of the present invention (I) compound as the application of electroluminescent material and contains the application of the mixture of formula (I) compound as electroluminescent material.
By electroluminescent spectrum, brightness, current/voltage characteristic analytical procedure test material and device performance, its characteristic of electroluminescent device of using formula of the present invention (I) compound is as follows: about cut-in voltage 5V, maximum brightness can reach 60000cd/m
2More than, luminous efficiency can reach more than the 20cd/A, is that 0.5-5wt% scope internal efficiency remains on more than the 10cd/A in doping content.This shows that the synthetic method of the compound of formula of the present invention (I) is simple, purification is convenient, be applied to electroluminescent material has characteristics such as cut-in voltage is low, brightness is high, luminous efficiency is high, good stability.
Description of drawings
Fig. 1: the electroluminescent device structural representation of using organic materials of the present invention.
The application of formula of the present invention (I) compound in electroluminescent device now is described by reference to the accompanying drawings. Object of the present invention can be used for preparing the electroluminescent device with one or more active layers, and in these active layers at least one deck contain one or more compounds of the present invention. Active layer can be a light-emitting layer and/or a migrating layer and/or a charge injection layer. The basic structure of this type of luminescent device as shown in Figure 1, this figure is the electroluminescent device of a sandwich construction, it is by ITO (tin indium oxide) conductive layer (positive pole) 2 and the metal (Al that are attached on the transparent glass 1, Mg: Ag alloy, Ca, Na, K) layer (negative pole) 7 and be clipped in two carrier injection layer (hole injection layer 3 and electron injecting layer 6) and two active layers formations between the two poles of the earth, these two active layers also are simultaneously that electron transport material 5 consists of by hole mobile material (such as NPB) 4 and luminescent material respectively, material therefor is electroluminescent organic material of the present invention in 5, or comprises electroluminescent organic material of the present invention. Hole and electronics inject from positive and negative polarities respectively, respectively transmission in hole transmission layer and electron transfer layer (also being luminescent layer) in two-layer near interface zone electronics and hole-recombination, and produces exciton, exciton is got back to ground state by radiation transistion, just has light to send. This radiative color can by changing the compound change of using as luminescent layer, be used material of the present invention and can prepare green light emitting device. In order to improve device performance 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.
These el light emitting devices can as on self luminous indicator elment such as signal lamp, aplhanumeric visual display, direction board, the photoelectronic coupler, the application in the various flat-panel monitor (display screens of mobile phone, DV, Digit camera, palm PC etc.).
Embodiment
Further illustrate the preparation and the application of The compounds of this invention below by example, rather than will limit the present invention with these examples.Due all raw materials of the present invention all can obtain from the commercial channel.
Example 1:TMDCzBQA's is synthetic
Compound 2,5-dihydroxyl-1-1,4-dicarboxylate 5.0 grams, 3,5-dimethyl phenylamino 10ml, hydrochloric acid 0.5ml is solvent reflux 6 hours with ethanol.Cold filtration is washed precipitation with ethanol and is promptly got pink product 2,5-two (3, the 5-xylidino)-1-1,4-dicarboxylate 8.2 grams, productive rate 90.3%.
With compound 2,5-two (3, the 5-xylidino)-1-1,4-dicarboxylate 5.0 gram and 1-chloronaphthalene were 260 ℃ of reflux 2 hours, filter, wash, promptly get product 1,3 with chloroform, 8,10-tetramethyl--6,13-dihydro-quinacridone 3.2 grams, productive rate 81.2%.
With compound 1,3,8,10-tetramethyl--6,13-dihydro-quinacridone 2.5 grams add oil of mirbane, potassium hydroxide, ethylene glycol monoemethyl ether, reflux 2 hours added ethanol 100ml, acetate 150ml reflux 2 hours again, product filter by washing, ethanol wash, chloroform washes and promptly gets red product.1,3,8,10-tetramethyl-quinacridone (TMQA) 2.1 gram productive rates 84.5%.
1，3，8，10-Tetramethyl-5，12-bis-(4-N-carbazolyl-butyl)quinacridone
TMDCzBQA
Above-mentioned TMQA is added in the tetrahydrofuran solvent, add 2.0ml 1,4-dibromobutane and a little sodium hydride, heating reflux reaction 12h.Cooling adds an amount of methyl alcohol and leaves standstill.Filter, separating out orange red solid with sherwood oil is 1,3,8,10-tetramethyl--5,12-two (4-brombutyl) quinacridone, product 2.0 grams, productive rate 50%.
With 1.05 gram carbazoles and above-mentioned 1,3,8,10-tetramethyl--5,12-two (4-brombutyl) quinacridone under a little KOH existence condition, heating reflux reaction 12h in butanone.Cooling washes with water, uses dichloromethane extraction again.With Al
2O
3Be stationary phase, hexanaphthene is that developping agent is walked chromatographic column, obtains red powder shape solid product 1,3,8,10-tetramethyl--5,12-two the 4-N-carbazyl) and butyl } quinacridone (TMDCzBQA) 0.76 gram, productive rate 30%.Mass spectrum molecular ion peak: 830.5.Chemical formula C is pressed in ultimate analysis
57H
58N
4O
2Calculate: C:82.4%; H:7.0%; N:6.7%; Experimental value: C:82.6%; H:7.2%; N:6.5%.
Example 2:TMDCzHQA's is synthetic
TMDCzHQA's is synthetic the same with example 1, and just with 1, the 6-dibromo-hexane replaces 1, and the 4-dibromobutane promptly gets product 1,3,8,10-tetramethyl--5,12-two the 4-N-carbazyl) and hexyl } quinacridone (TMDCzHQA).Mass spectrum molecular ion peak: 886.5.Chemical formula C is pressed in ultimate analysis
61H
66N
4O
2Calculate: C:82.6%; H:7.5%; N:6.3%; Experimental value: C:82.6%; H:7.2%; N:6.5%.
Example 3:TMDCzOQA's is synthetic
TMDCzOQA's is synthetic the same with example 1, and just with 1,8-two bromooctanes replace 1, and the 4-dibromobutane promptly gets product 1,3,8,10-tetramethyl--5,12-two the 4-N-carbazyl) and octyl group } quinacridone (TMDCzOQA).Mass spectrum molecular ion peak: 942.6.Chemical formula C is pressed in ultimate analysis
65H
74N
4O
2Calculate: C:82.8%; H:7.9%; N:5.9%; Experimental value: C:82.6%; H:7.8%; N:6.0%.
1，3，8，10-Tetramethyl-5，12-bis- 1，3，8，10-Tetramethyl-5，12-bis-(4-N-carbazolyl)-hexyl)quinacridone (4-N-carbazolyl-octyl)quinacridone
TMDCzHQA TMDCzOQA
Example 4:TMDCzDQA's is synthetic
TMDCzDQA's is synthetic the same with example 1, and just with 1, the 10-dibromo-decane replaces 1, and the 4-dibromobutane promptly gets product 1,3,8,10-tetramethyl--5,12-two the 4-N-carbazyl) and decyl } quinacridone (TMDCzDQA).Mass spectrum molecular ion peak: 998.6.Chemical formula C is pressed in ultimate analysis
69H
82N
4O
2Calculate: C:82.9%; H:8.3%; N:5.6%; Experimental value: C:82.6%; H:8.2%; N:5.8%.
1，3，8，10-Tetramethyl-5，12-bis- 1，3，8，10-Tetramethyl-5，12-bis-(4-N-carbazolyl-decyl)quinacridone (4-(3，6-diethyl-N-carbazolyl)-butyl)quinacridone
TMDCzDQA TMDECzBQA
Example 5:TMDECzBQA's is synthetic
Add 3.0 gram carbazoles in the reaction flask, 5ml ethyl chloride, an amount of Aluminum chloride anhydrous, 0 ℃ of following stirring reaction 24h.Reaction mixture is slowly poured in the water, left standstill.Use the dichloromethane extraction crude product, be spin-dried for.With Al
2O
3Be stationary phase, hexanaphthene is that developping agent is walked chromatographic column.Obtain 3,6-diethyl carbazole 2.0 grams, productive rate 50%.
1,3,8,10-tetramethyl--5, the synthesis step of 12-two (4-brombutyl) quinacridone is identical with example 1.
With obtain 3,6-diethyl carbazole and 1,3,8,10-tetramethyl--5,12-two (4-brombutyl) quinacridone under a little KOH existence condition, heating reflux reaction 12h in butanone.Cooling washes with water, uses dichloromethane extraction again.With Al
2O
3Be stationary phase, hexanaphthene is that developping agent is walked chromatographic column, obtains product 1,3,8,10-tetramethyl--5,12-two { 4-(3,6-diethyl-N-carbazyl) butyl } quinacridone (TMDECzBQA) 0.82 gram, productive rate 30%.Mass spectrum molecular ion peak: 924.5.Chemical formula C is pressed in ultimate analysis
64H
68N
4O
2Calculate: C:83.1%; H:7.4%; N:6.1%; Experimental value: C:83.1%; H:7.7%; N:6.0%.
Example 6:TMDECzHQA
TMDECzHQA's is synthetic the same with example 5, and just with 1, the 6-dibromo-hexane replaces 1, and the 4-dibromobutane promptly gets product 1,3,8,10-tetramethyl--5,12-two { 4-(3,6-diethyl-N-carbazyl) hexyl } quinacridone (TMDECzHQA).Mass spectrum molecular ion peak: 980.6.Chemical formula C is pressed in ultimate analysis
68H
76N
4O
2Calculate: C:83.2%; H:7.8%; N:5.7%; Experimental value: C:83.1%; H:7.9%; N:5.8%.
Example 7:TMTECzBQA
Synthetic and the example 5 of TMTECzBQA is similar, just the amount of ethyl chloride is increased to six times of carbazole amount when the synthetic substituted carbazole of the first step, can obtain 1,3,6 by column chromatography again, 8-tetraethyl-carbazole.
Product 1,3,8,10-tetramethyl--5,12-two { 4-(1,3,6,8-tetraethyl--N-carbazyl) butyl } quinacridone (TMTECzBQA).Mass spectrum molecular ion peak: 1036.7.Chemical formula C is pressed in ultimate analysis
72H
84N
4O
2Calculate: C:83.4%; H:8.2%; N:5.4%; Experimental value: C:83.5%; H:8.3%; N:5.0%.
1，3，8，10-Tetramethyl-5，12-bis- 1，3，8，10-Tetramethyl-5，12-bis-(4-(3，6-diethyl-N-carbazolyl)-hexyl)quinacridone (4-(1，3，6，8-tetraethyl-N-carbazolyl)-butyl)quinacridone
TMDECzHQA TMTECzBQA
Example 8:TMTECzOQA
TMTECzOQA's is synthetic similar with example 7, and just with 1,8-two bromooctanes replace 1, and the 4-dibromobutane promptly gets product 1,3,8,10-tetramethyl--5,12-two { 4-(1,3,6,8-tetraethyl--N-carbazyl) octyl group } quinacridone (TMTECzOQA).Mass spectrum molecular ion peak: 1148.8.Chemical formula C is pressed in ultimate analysis
80H
100N
4O
2Calculate: C:83.6%; H:8.8%; N:4.9%; Experimental value: C:83.5%; H:8.7%; N:4.7%.
Example 9:TMDPCzBQA
TMDPCzBQA's is synthetic similar with example 5, just when the first step is synthesized substituted carbazole, replaces ethyl chloride with propyl chloride.Product 1,3,8,10-tetramethyl--5,12-two { 4-(3,6-dipropyl-N-carbazyl) butyl } quinacridone (TMDPCzBQA).Mass spectrum molecular ion peak: 980.6.Chemical formula C is pressed in ultimate analysis
68H
76N
4O
2Calculate: C:83.2%; H:7.8%; N:5.7%; Experimental value: C:83.0%; H:7.9%; N:5.6%.
1，3，8，10-Tetramethyl-5，12-bis- 1，3，8，10-Tetramethyl-5，12-bis-{4-(1，3，6，8-tetraethyl-N-carbazolyl)-octyl}quinacridone {4-(3，6-dipropyl-N-carbazolyl)-butyl}quinacridone
TMTECzOQA TMDPCzBQA
Example 10:TMDPCzOQA
TMDPCzOQA's is synthetic similar with example 9, and just with 1,8-two bromooctanes replace 1,4-dibromobutane, product 1,3,8,10-tetramethyl--5,12-two { 4-(3,6-dipropyl N-carbazyl) octyl group } quinacridone (TMDPCzOQA).Mass spectrum molecular ion peak: 1092.7.Chemical formula C is pressed in ultimate analysis
76H
92N
4O
2Calculate: C:83.5%; H:8.5%; N:5.1%; Experimental value: C:83.2%; H:8.6%; N:5.2%.
1，3，8，10-Tetramethyl-5，12-bis-(4-(3，6-dipropyl- 1，3，8，10-Tetramethyl-5，12-bis-(4-(1，3，6，8-tet
N-carbazolyl)-octyl)quinacridone rapropyl-N-carbazolyl)-hexyl)quinacridone
TMDPCzOQA TMTPCzHQA
Example 11:TMTPCzHQA
Synthetic and the example 5 of TMTPCzHQA is similar, replaces ethyl chloride with propyl chloride when the synthetic substituted carbazole of the first step, and the amount of propyl chloride is increased to six times of carbazole amount, can obtain 1,3,6 by column chromatography again, 8-tetrapropyl carbazole.
With 1, the 6-dibromo-hexane replaces 1, the 4-dibromobutane.Product 1,3,8,10-tetramethyl--5,12-two { 4-(1,3,6,8-tetrapropyl-N-carbazyl) hexyl } quinacridone (TMTPCzHQA).Mass spectrum molecular ion peak: 1204.9.Chemical formula C is pressed in ultimate analysis
84H
108N
4O
2Calculate: C:83.7%; H:9.0%; N:4.7%; Experimental value: C:83.4%; H:9.2%; N:4.7%.
Example 12:TMTPCzDQA
TMTPCzDQA's is synthetic similar with example 11, and with 1, the 10-dibromo-decane replaces 1, and the 6-dibromo-hexane promptly gets product 1,3,8,10-tetramethyl--5,12-two { 4-(1,3,6,8-tetrapropyl-N-carbazyl) decyl } quinacridone (TMTPCzDQA).Mass spectrum molecular ion peak: 1317.0.Chemical formula C is pressed in ultimate analysis
92H
124N
4O
2Calculate: C:83.8%; H:9.5%; N:4.3%; Experimental value: C:83.7%; H:9.8%; N:4.1%
1，3，8，10-Tetramethyl-5，12-bis-(4-(1，3，6，8-tetr 1，3，8，10-Tetramethyl-5，12-bis-(4-(3，6-di-tert-
apropyl-N-carbazolyl)-decyl)quinacridone butyl-N-carbazolyl)-butyl)quinacridone
TMTPCzDQA TMDTCzBQA
Example 13:TMDTCzBQA
TMDTCzBQA's is synthetic similar with example 5, replaces ethyl chloride with tertiary butyl chloride when the first step is synthesized substituted carbazole, can obtain 3 by column chromatography again, 6-di-t-butyl carbazole.
Product 1,3,8,10-tetramethyl--5,12-two { 4-(3,6-di-t-butyl-N-carbazyl) butyl } quinacridone (TMDTCzBQA).Mass spectrum molecular ion peak: 1036.7.Chemical formula C is pressed in ultimate analysis
72H
84N
4O
2Calculate: C:83.4%; H:8.2%; N:5.4%; Experimental value: C:83.4%; H:84%; N:5.2%.
Example 14:TMDTCzHQA
TMDTCzHQA's is synthetic similar with example 13, and just with 1, the 6-dibromo-hexane replaces 1, and the 4-dibromobutane promptly gets product 1,3,8,10-tetramethyl--5,12-two { 4-(3,6-di-t-butyl-N-carbazyl) hexyl } quinacridone (TMDTCzHQA).Mass spectrum molecular ion peak: 1092.7.Chemical formula C is pressed in ultimate analysis
76H
92N
4O
2Calculate: C:83.5%; H:8.5%; N:5.1%; Experimental value: C:83.5%; H:8.3%; N:5.3%.
1，3，8，10-Tetramethyl-5，12-bis-(4-(3，6-di-tert-buty 1，3，8，10-Tetramethyl-5，12-bis-(4-(1，3，6，8-tetra-tert-buty
l-N-carbazolyl)-hexyl)quinacridone l-N-carbazolyl)-hexyl)quinacridone
TMDTCzHQA TMTTCzHQA
Example 15:TMTTCzHQA
Synthetic and the example 13 of TMTTCzHQA is similar, just the amount of tertiary butyl chloride is increased to six times of carbazole amount when synthetic substituted carbazole, can obtain 1,3,6 by column chromatography again, 8-tetra-tert carbazole.
With 1, the 6-dibromo-hexane replaces 1, and the 4-dibromobutane promptly gets product 1,3,8,10-tetramethyl--5,12-two { 4-(1,3,6,8-tetra-tert-N-carbazyl) hexyl } quinacridone (TMTTCzHQA).Mass spectrum molecular ion peak: 1317.0.Chemical formula C is pressed in ultimate analysis
92H
124N
4O
2Calculate: C:83.8%; H:9.5%; N:4.3%; Experimental value: C:83.8%; H:9.4%; N:4.4%.
Example 16:TMTTCzOQA
TMTTCzOQA's is synthetic the same with example 15, and just with 1,8-two bromooctanes replace 1, and the 6-dibromo-hexane promptly gets product 1,3,8,10-tetramethyl--5,12-two { 4-(1,3,6,8-tetra-tert-N-carbazyl) octyl group } quinacridone (TMTTCzOQA).Mass spectrum molecular ion peak: 1373.0.Chemical formula C is pressed in ultimate analysis
96H
132N
4O
2Calculate: C:83.9%; H:9.7%; N:4.1%; Experimental value: C:84.0%; H:9.4%; N:3.9%.
1，3，8，10-Tetramethyl-5，12-bis-(4-(1，3，6，8-tetra- 1，3，8，10-Tetramethoxyl-5，12-bis-(4-(3，6-di
tert-butyl-N-carbazolyl}-octyl)quinacridone ethyl-N-carbazolyl)-butyl)quinacridone
TMTTCzOQA TMODECzBQA
Example 17:TMODECzBQA
TMDECzBQA's is synthetic similar in the synthetic and example 5 of TMODECzBQA, and with 3, the 5-dimethoxyaniline replaces 3, the 5-xylidine.Obtain product 1,3,8,10-tetramethoxy-5,12-two { 4-(3,6-diethyl-N-carbazyl) butyl } quinacridone (TMODECzBQA).Mass spectrum molecular ion peak: 988.5.Chemical formula C is pressed in ultimate analysis
64H
68N
4O
6Calculate: C:77.7%; H:6.9%; N:5.7%; Experimental value: C:77.8%; H:7.0%; N:5.5%.
Example 18:TMOTECzHQA
Similar with example 17, just when synthetic substituted carbazole, the amount of ethyl chloride is increased to six times of carbazole amount, can obtain 1,3,6 by column chromatography again, 8-tetraethyl-carbazole.With 1, the 6-dibromo-hexane replaces 1, the 4-dibromobutane.Product 1,3,8,10-tetramethoxy-5,12-two { 4-(1,3,6,8-tetraethyl--N-carbazyl) hexyl } quinacridone (TMOTECzHQA).Mass spectrum molecular ion peak: 1156.7.Chemical formula C is pressed in ultimate analysis
76H
92N
4O
6Calculate: C:78.9%; H:8.0%; N:4.8%; Experimental value: C:78.8%; H:8.0%; N:5.0%.
1，3，8，10-Tetramethoxyl-5，12-bis-(4-(1，3，6，8-tetra 1，3，8，10-Tetramethoxyl-5，12-bis-(4-(3，6-dipropyl
ethyl-N-carbazolyl)-hexyl)quinacridone -N-carbazolyl)-octyl)quinacridone
TMOTECzHQA TMODPCzOQA
Example 19:TMODPCzOQA
TMODPCzOQA's is synthetic similar with example 17, just replaces ethyl chloride with propyl chloride when the first step is synthesized substituted carbazole, and with 1,8-two bromooctanes replace 1, the 4-dibromobutane.Product 1,3,8,10-tetramethoxy-5,12-two { 4-(3,6-dipropyl-N-carbazyl) octyl group } quinacridone (TMODPCzOQA).Mass spectrum molecular ion peak: 1156.7.Chemical formula C is pressed in ultimate analysis
76H
92N
4O
6Calculate: C:78.9%; H:8.0%; N:4.8%; Experimental value: C:78.8%; H:4.0%; N:4.9%.
Example 20:TMOTPCzHQA
Synthetic and the example 18 of TMOTPCzHQA is similar, just replaces ethyl chloride with propyl chloride when synthetic substituted carbazole, and the amount of propyl chloride is increased to six times of carbazole amount, obtains 1,3,6 by column chromatography again, 8-tetrapropyl carbazole.Product 1,3,8,10-tetramethoxy-5,12-two { 4-(1,3,6,8-tetrapropyl N-carbazyl) hexyl } quinacridone (TMOTPCzHQA).Mass spectrum molecular ion peak: 1268.8.Chemical formula C is pressed in ultimate analysis
84H
108N
4O
6Calculate: C:79.5%; H:8.6%; N:4.4%; Experimental value: C:79.8%; H:8.4%; N:4.3%.
1，3，8，10-Tetramethoxyl-5，12-bis-(4-(1，3，6，8-tetrapr 1，3，8，10-Tetramethoxyl-5，12-bis-(4-(3，6-di-tert-butyl-N-
opyl-N-carbazolyl)-hexyl)quinacridone carbazolyl)-decyl)quinacridone
TMOTPCzHQA TMODTCzDQA
Example 21:TMODTCzDQA
Similar in the synthetic and example 17 of TMODTCzDQA, just when synthesizing substituted carbazole, the first step replaces ethyl chloride with tertiary butyl chloride, with 1, the 10-dibromo-decane replaces 1, the 4-dibromobutane, obtain product 1,3,8,10-tetramethoxy-5,12-two { 4-(3,6-di-t-butyl-N-carbazyl) decyl } quinacridone (TMODTCzDQA).Mass spectrum molecular ion peak: 1268.8.Chemical formula C is pressed in ultimate analysis
84H
108N
4O
6Calculate: C:79.5%; H:8.6%; N:4.4%; Experimental value: C:79.4%; H:8.5%; N:4.4%.
Example 22:TMOTTCzDoQA
Synthetic and the example 18 of TMOTTCzDoQA is similar, just replaces ethyl chloride with tertiary butyl chloride when synthetic substituted carbazole, and the amount of tertiary butyl chloride is increased to six times of carbazole amount, obtains 1,3,6 by column chromatography again, 8-tetra-tert carbazole.With 1, the 12-dibromo-dodecane replaces 1, the 6-dibromo-hexane.Product 1,3,8,10-tetramethoxy-5,12-two { 4-(1,3,6,8-tetra-tert-N-carbazyl) dodecyl } quinacridone (TMOTTCzDoQA).Mass spectrum molecular ion peak: 1549.1.Chemical formula C is pressed in ultimate analysis
104H
148N
4O
6Calculate: C:80.6%; H:9.6%; N:3.6%; Experimental value: C:80.5%; H:9.4%; N:3.7%.
1，3，8，10-Tetramethoxyl-5，12-bis-(4-(1，3，6，8-tetra- 1，3，8，10-Tetraphenoxy-5，12-bis-(4-(3，6-dieth
tert-butyl-N-carbazolyl)-dodecyl)quinacridone yl-N-carbazolyl)-hexyl)quinacridone
TMOTTCzDoQA TPODECzHQA
Example 23:TPODECzHQA
Synthetic similar in the synthetic and example 5 of TPODECzHQA, with 3,5-two phenoxybenzamines replace 3, the 5-xylidine, with 1, the 6-dibromo-hexane replaces 1, the 4-dibromobutane, promptly get product 1,3,8,10-four phenoxy groups-5,12-two { 4-(3,6-diethyl-N-carbazyl) hexyl } quinacridone (TPODECzHQA).Mass spectrum molecular ion peak: 1292.6.Chemical formula C is pressed in ultimate analysis
88H
84N
4O
6Calculate: C:81.7%; H:6.5%; N:4.3%; Experimental value: C:81.5%; H:48.2%; N:4.5%.
Example 24:TPOTECzDQA
Synthetic and the example 23 of TPOTECzDQA is similar, just the amount of ethyl chloride is increased to six times of carbazole amount when synthetic substituted carbazole, can obtain 1,3,6 by column chromatography again, 8-tetraethyl-carbazole.With 1, the 10-dibromo-decane replaces 1, the 6-dibromo-hexane.Obtain product 1,3,8,10-four phenoxy groups-5,12-two { 4-(1,3,6,8-tetraethyl--N-carbazyl) decyl } quinacridone (TPOTECzDQA).Mass spectrum molecular ion peak: 1516.9.Chemical formula C is pressed in ultimate analysis
104H
116N
4O
6Calculate: C:82.3%; H:7.7%; N:3.7%; Experimental value: C:82.5%; H:7.8%; N:3.5%.
1，3，8，10-Tetraphenoxy-5，12-bis-(4-(1，3，6，8-tetrae
thyl-N-carbazolyl)-decyl)quinacridone
TPOTECzDQA
Example 25:TPODPCzBQA
Synthetic similar in the synthetic and example 23 of TPODPCzBQA, just when synthesizing substituted carbazole, replace ethyl chloride with propyl chloride.With 1, the 4-dibromobutane replaces 1, the 6-dibromo-hexane.
Product 1,3,8,10-four phenoxy groups-5,12-two { 4-(3,6-dipropyl-N-carbazyl) butyl } quinacridone (TPODPCzBQA).Mass spectrum molecular ion peak: 1292.6.Chemical formula C is pressed in ultimate analysis
88H
84N
4O
6Calculate: C:81.7%; H:6.5%; N:4.3%; Experimental value: C:81.8%; H:6.3%; N:4.5%.
1，3，8，10-Tetraphenoxy-5，12-bis-(4-(3，6-dipropyl
-N-carbazolyl)-butyl)quinacridone
TPODPCzBQA
Example 26:TPOTPCzDoQA
TPOTPCzDoQA's is synthetic similar with example 24, just replaces ethyl chloride with propyl chloride when synthesizing substituted carbazole.With 1, the 12-dibromo-dodecane replaces 1, the 10-dibromo-decane.
Product 1,3,8,10-four phenoxy groups-5,12-two { 4-(1,3,6,8-tetrapropyl-N-carbazyl) dodecyl } quinacridone (TPOTPCzDoQA).Mass spectrum molecular ion peak: 1685.1.Chemical formula C is pressed in ultimate analysis
116H
140N
4O
6Calculate: C:82.6%; H:8.4%; N:3.3%; Experimental value: C:82.5%; H:8.6%; N:3.5%.
1，3，8，10-Tetraphenoxy-5，12-bis-(4-(1，3，6，8-tetr
apropyl-N-carbazolyl)-dodecyl)quinacridone
TPODPCzBQA
Example 27:TPODTCzDoQA
Synthetic similar in the synthetic and example 23 of TPODTCzHQA, just when synthesizing substituted carbazole, replace ethyl chloride with tertiary butyl chloride.With 1, the 12-dibromo-dodecane replaces 1, and the 6-dibromo-hexane promptly gets product 1,3,8,10-four phenoxy groups-5,12-two { 4-(3,6-di-t-butyl-N-carbazyl) dodecyl } quinacridone (TPODTCzDoQA).Mass spectrum molecular ion peak: 1573.0.Chemical formula C is pressed in ultimate analysis
108H
124N
4O
6Calculate: C:82.4; H:7.9%; N:3.6%; Experimental value: C:82.5%; H:7.9%; N:32%.
1，3，8，10-Tetraphenoxy-5，12-bis-(4-(3，6-di-tert-bu
tyl-N-carbazolyl)-dodecyl)quinacridone
TPODTCzDoQA
Example 28:TPOTTCzDQA
Synthetic similar in the synthetic and example 24 of TPOTTCzDQA, just when synthesizing substituted carbazole, replace ethyl chloride with tertiary butyl chloride.Promptly get product 1,3,8,10-four phenoxy groups-5,12-two { 4-(1,3,6,8-tetra-tert-N-carbazyl) decyl } quinacridone (TPOTTCzDQA).Mass spectrum molecular ion peak: 1741.1.Chemical formula C is pressed in ultimate analysis
120H
148N
4O
6Calculate: C:82.7%; H:8.6%; N:3.2%; Experimental value: C:82.5%; H:8.5%; N:3.3%.
Example 29:TFDECzHQA
The synthetic of TFDECzHQA synthetic with example 5 in synthetic similar, with 3, the 5-difluoroaniline replaces 3, the 5-xylidine, with 1,6-dibromo-hexane replacement 1,4-dibromobutane.
Product 1,3,8,10-tetrafluoro-5,12-two { 4-(3,6-diethyl N-carbazyl) hexyl } quinacridone (TFDECzHQA).Mass spectrum molecular ion peak: 996.5.Chemical formula C is pressed in ultimate analysis
64H
64F
4N
4O
2Calculate: C:77.1%; H:6.5%; N:5.6%; Experimental value: C:77.3%; H:6.4%; N:5.5%.
1，3，8，10-Tetraphenoxy-5，12-bis-(4-(1，3，6，8-tetra-t 1，3，8，10-Tetrafluoro-5，12-bis-(4-(3，6-dieth
ert-butyl-N-carbazolyl)-decyl)quinacridone yl-N-carbazolyl)-hexyl)quinacridone
TPOTTCzDQA TFDECzHQA
Example 30:TFTECzDQA
Synthetic and the example 29 of TPOTECzDQA is similar, just the amount of ethyl chloride is increased to six times of carbazole amount when synthetic substituted carbazole, can obtain 1,3,6 by column chromatography again, 8-tetraethyl-carbazole.With 1, the 10-dibromo-decane replaces 1, the 6-dibromo-hexane.Product 1,3,8,10-tetrafluoro-5,12-two { 4-(1,3,6,8-tetraethyl--N-carbazyl) decyl } quinacridone (TFTECzDQA).Mass spectrum molecular ion peak: 1220.8.Chemical formula C is pressed in ultimate analysis
80H
96F
4N
4O
2Calculate: C:78.7%; H:7.9%; N:4.6%; Experimental value: C:78.5%; H:8.0%; N:4.5%.
1，3，8，10-Tetrafluoro-5，12-bis-(4-(1，3，6，8-tetraeth 1，3，8，10-Tetrafluoro-5，12-bis-(4-(3，6-dipropy
yl-N-carbazolyl)-decyl)quinacridone l-N-carbazolyl)-butyl)quinacridone
TFTECzDQA TFDPCzBQA
Example 31:TFDPCzBQA
Synthetic similar in the synthetic and example 29 of TFDPCzBQA, just when synthesizing substituted carbazole, replace ethyl chloride with propyl chloride.With 1, the 4-dibromobutane replaces 1, the 6-dibromo-hexane.
Product 1,3,8,10-tetrafluoro-5,12-two { 4-(3,6-dipropyl-N-carbazyl) butyl } quinacridone (TFDPCzBQA).Mass spectrum molecular ion peak: 996.5.Chemical formula C is pressed in ultimate analysis
64H
64F
4N
4O
2Calculate: C:77.1%; H:6.5%; N:5.6%; Experimental value: C:77.3%; H:6.3%; N:5.8%.
Example 32:TFTPCzOQA
Synthetic similar in the synthetic and example 30 of TFTPCzOQA, just when synthesizing substituted carbazole, replace ethyl chloride with propyl chloride.With 1,8-two bromooctanes replace 1, the 10-dibromo-decane.
Product 1,3,8,10-tetrafluoro-5,12-two { 4-(1,3,6,8-tetrapropyl-N-carbazyl) octyl group } quinacridone (TFTPCzOQA).Mass spectrum molecular ion peak: 1276.8.Chemical formula C is pressed in ultimate analysis
84H
104F
4N
4O
2Calculate: C:79.0%; H:8.2%; N:4.4%; Experimental value: C:79.3%; H:8.3%; N:4.2%.
1，3，8，10-Tetrafluoro-5，12-bis-(4-(1，3，6，8-te 1，3，8，10-Tetrafluoro-5，12-bis-(4-(3，6-di-tert-but
trapropyl-N-carbazolyl)-octyl)quinacridone yl-N-carbazolyl)-butyl)quinacridone
TFTPCzOQA TFDTCzBQA
Example 33:TFDTCzBQA
Synthetic similar in the synthetic and example 29 of TFDTCzBQA, just when synthesizing substituted carbazole, replace ethyl chloride with tertiary butyl chloride.With 1, the 4-dibromobutane replaces 1, the 6-dibromo-hexane.Product 1,3,8,10-tetrafluoro-5,12-two { 4-(3,6-di-t-butyl N-carbazyl) butyl } quinacridone (TFDTCzBQA).Mass spectrum molecular ion peak: 1052.6.Chemical formula C is pressed in ultimate analysis
68H
72F
4N
4O
2Calculate: C:77.5%; H:6.9%; N:5.3%; Experimental value: C:77.6%; H:6.9%; N:5.0%.
Example 34:TFTTCzDQA
Synthetic similar in the synthetic and example 30 of TFDTCzDQA, just when synthesizing substituted carbazole, replace ethyl chloride with tertiary butyl chloride.Product 1,3,8,10-tetrafluoro-5,12-two { 4-(1,3,6,8-tetra-tert-N-carbazyl) decyl } quinacridone (TFTTCzDQA).Mass spectrum molecular ion peak: 1445.Chemical formula C is pressed in ultimate analysis
96H
128F
4N
4O
2Calculate: C:79.7%; H:8.9%; N:3.9%; Experimental value: C:79.5%; H:8.9%; N:4.0%.
Example 35:TCDECzOQA
Synthetic similar in the synthetic and example 5 of TCDECzOQA, with 3, the 5-dichlorphenamide bulk powder replaces 3, the 5-xylidine.With 1,8-two bromooctanes replace 1, the 4-dibromobutane.
Product 1,3,8,10-tetrachloro-5,12-two { 4-(3,6-diethyl-N-carbazyl) octyl group } quinacridone (TCDECzOQA).Mass spectrum molecular ion peak: 1116.4.Chemical formula C is pressed in ultimate analysis
68H
72Cl
4N
4O
2Calculate: C:73.0%; H:6.5%; N:5.0%; Experimental value: C:73.4%; H:6.4%; N:5.1%.
1，3，8，10-Tetrafluoro-5，12-bis-(4-(1，3，6，8-tertra- 1，3，8，10-Tetrachloro-5，12-bis-(4-(3，6-diethyl-N
tert-butyl-N-carbazolyl)-decyl)quinacridone -carbazolyl)-octyl)quinacridone
TFTTCzDQA TCDECzOQA
Example 36:TCTECzDQA
Synthetic similar in the synthetic and example 35 of TCTECzDQA, just when synthetic substituted carbazole, the amount of ethyl chloride is increased to six times of carbazole amount, can obtain 1,3,6 by column chromatography again, 8-tetraethyl-carbazole.With 1, the 10-dibromo-decane replaces 1,8-two bromooctanes.Mass spectrum molecular ion peak: 1284.6.Chemical formula C is pressed in ultimate analysis
80H
96Cl
4N
4O
2Calculate: C:74.6%; H:7.5%; N:4.4%; Experimental value: C:74.4%; H:4.4%; N:4.6%
1，3，8，10-Tetrachloro-5，12-bis-(4-(1，3，6，8-tetr 1，3，8，10-Tetrachloro-5，12-bis-(4-(3，6-dipropy
aethyl-N-carbazolyl)-decyl)quinacridone l-N-carbazolyl)-hexyl)quinacridone
TCTECzDQA TCDPCzHQA
Example 37:TCDPCzHQA
Synthetic similar in the synthetic and example 35 of TCDPCzHQA, just when synthesizing substituted carbazole, replace ethyl chloride with propyl chloride.With 1, the 6-dibromo-hexane replaces 1,8-two bromooctanes.
Product 1,3,8,10-tetrachloro-5,12-two { 4-(3,6-dipropyl-N-carbazyl) hexyl } quinacridone (TCDPCzHQA).Mass spectrum molecular ion peak: 1116.4.Chemical formula C is pressed in ultimate analysis
68H
72Cl
4N
4O
2Calculate: C:73.0%; H:6.5%; N:5.0%; Experimental value: C:73.2%; H:6.2%; N:5.1%.
Example 38:TCTPCzDoQA
Synthetic similar in the synthetic and example 36 of TCTPCzDoQA, just when synthesizing substituted carbazole, replace ethyl chloride with propyl chloride.
Product 1,3,8,10-tetrachloro-5,12-two { 4-(1,3,6,8-tetrapropyl-N-carbazyl) dodecyl } quinacridone (TCTPCzDoQA).Mass spectrum molecular ion peak: 1452.8.Chemical formula C is pressed in ultimate analysis
92H
120Cl
4N
4O
2Calculate: C:75.9%; H:8.3%; N:3.9%; Experimental value: C:75.8%; H:8.2%; N:4.2%.
1，3，8，10-Tetrachloro-5，12-bis-(4-(1，3，6，8-tetr 1，3，8，10-Tetrachloro-5，12-bis-(4-(3，6-di-ter
apropyl-N-carbazolyl)-dodecyl)quinacridone t-butyl-N-carbazolyl)-octyl)quinacridone
TCTPCzDoQA TCDTCzOQA
Example 39:TCDTCzOQA
Synthetic similar in the synthetic and example 35 of TCDTCzOQA, just when synthesizing substituted carbazole, replace ethyl chloride with tertiary butyl chloride.Product 1,3,8,10-tetrachloro-5,12-two { 4-(3,6-di-t-butyl-N-carbazyl) octyl group } quinacridone (TCDTCzOQA).Mass spectrum molecular ion peak: 1228.6.Chemical formula C is pressed in ultimate analysis
76H
88Cl
4N
4O
2Calculate: C:74.1%; H:7.2%; N:4.6%; Experimental value: C:74.2%; H:6.9%; N:4.5%.
Example 40:TCTTCzTQA
Synthetic similar in the synthetic and example 36 of TCTTCzTQA, just when synthesizing substituted carbazole, replace ethyl chloride with tertiary butyl chloride.With 1,14-two bromo-tetradecanes replace 1,10 dibromo-decane promptly to get product.Product 1,3,8,10-tetrachloro-5,12-two { 4-(1,3,6,8-tetra-tert-N-carbazyl) tetradecyl } quinacridone (TCTTCzTQA).Mass spectrum molecular ion peak: 1621.Chemical formula C is pressed in ultimate analysis
104H
144Cl
4N
4O
2Calculate: C:76.9%; H:8.9%; N:3.5%; Experimental value: C:76.8%; H:8.7%; N:3.8%.
Example 41:TNDECzBQA
TNDECzBQA's is synthetic similar with example 5, and with 3,5-two (1-naphthyloxy) aniline replaces 3, the 5-xylidine.Product 1,3,8,10-four (1-naphthyloxy)-5,12-two { 4-(3,6-diethyl-N-carbazyl) butyl } quinacridone (TNDECzBQA).Mass spectrum molecular ion peak: 1436.6.Chemical formula C is pressed in ultimate analysis
100H
84N
4O
6Calculate: C:83.5%; H:5.9%; N:3.9%; Experimental value: C:83.6%; H:6.1%; N:3.4%.
1，3，8，10-Tetrachloro-5，12-bis-(4-(1，3，6，8-tetra-t 1，3，8，10-Tetrakis-(naphthalen-1-yl-oxy)-5，12-bis-
ert-butyl-N-carbazolyl)-tetradecyl)quinacridone {4-(3，6-diethyl-N-carbazolyl)-butyl}quinacridone
TCTTCzTQA TNDECzBQA
Example 42:TNTECzDQA
Synthetic similar in the synthetic and example 41 of TNTECzDQA, just when synthetic substituted carbazole, the amount of ethyl chloride is increased to six times of carbazole amount, can obtain 1,3,6 by column chromatography again, 8-tetraethyl-carbazole.With 1, the 10-dibromo-decane replaces 1, the 4-dibromobutane.Product 1,3,8,10-four (1-naphthyloxy)-5,12-two { 4-(1,3,6,8-tetraethyl--N-carbazyl) decyl } quinacridone (TNTECzDQA).Mass spectrum molecular ion peak: 1717.0.Chemical formula C is pressed in ultimate analysis
120H
124N
4O
6Calculate: C:83.9%; H:7.3%; N:3.3%; Experimental value: C:83.6%; H:7.1%; N:3.4%.
1，3，8，10-Tetrakis-(naphthalen-1-yl-oxy)-5，12-bis- (4-(1，3，6，8-tetraethyl-N-carbazolyl)-decyl)quinacridone
TNTECzDQA
1，3，8，10-Tetrakis-(naphthalen-1-yl-oxy)-5，12-bis-
(4-(3，6-dipropyl-N-carbazolyl)-hexyl)quinacridone
TNDPCzHQA
Example 43:TNDPCzHQA
Synthetic similar in the synthetic and example 41 of TNDPCzHQA, just when synthesizing substituted carbazole, replace ethyl chloride with propyl chloride.With 1, the 6-dibromo-hexane replaces 1, and the 4-dibromobutane promptly gets product.
Product 1,3,8,10-four (1-naphthyloxy)-5,12-two { 4-(3,6-dipropyl-N-carbazyl) hexyl } quinacridone (TNDPCzHQA).Mass spectrum molecular ion peak: 1548.8.Chemical formula C is pressed in ultimate analysis
108H
100N
4O
6Calculate: C:83.7%; H:6.5%; N:3.6%; Experimental value: C:83.6%; H:6.1%; N:3.4%
Example 44:TNTPCzOQA
Synthetic similar in the synthetic and example 42 of TNTPCzOQA, just when synthesizing substituted carbazole, replace ethyl chloride with propyl chloride.With 1,8-two bromooctanes replace 1, the 10-dibromo-decane.
Product 1,3,8,10-four (1-naphthyloxy)-5,12-two { 4-(1,3,6,8-tetrapropyl-N-carbazyl) octyl group } quinacridone (TNTPCzOQA).Mass spectrum molecular ion peak: 1773.0.Chemical formula C is pressed in ultimate analysis
124H
132N
4O
6Calculate: C:83.9%; H:7.5%; N:3.2%; Experimental value: C:83.6%; H:7.6%; N:3.4%.
1，3，8，10-Tetrakis-(naphthalen-1-yl-oxy)-5，12-bis- (4-(1，3，6，8-tetrapropyl-N-carbazolyl)-octyl)quinacridone
TNTPCzOQA
Example 45:TNDTCzHQA
TNDTCzHQA's is synthetic similar with example 41, just replaces ethyl chloride with tertiary butyl chloride when synthesizing substituted carbazole.With 1, the 6-dibromo-hexane replaces 1, and the 4-dibromobutane promptly gets product.Product 1,3,8,10-four (1-naphthyloxy)-5,12-two { 4-(3,6-di-t-butyl N-carbazyl) hexyl } quinacridone (TNDTCzHQA).Mass spectrum molecular ion peak: 1604.8.Chemical formula C is pressed in ultimate analysis
112H
108N
4O
6Calculate: C:83.8%; H:6.8%; N:3.5%; Experimental value: C:84.0%; H:6.8%; N:3.4%.
1，3，8，10-Tetrakis-(naphthalen-1-yl-oxy)-5，12-bis- (4-(3，6-di-tert-butyl-N-carbazolyl)-hexyl)quinacridone
TNDTCzHQA
Example 46:TNTTCzDQA
TNTTCzDQA's is synthetic similar with example 42, just replaces ethyl chloride with tertiary butyl chloride when synthesizing substituted carbazole.Product 1,3,8,10-four (1-naphthyloxy)-5,12-two { 4-(1,3,6,8-tetra-tert-N-carbazyl) decyl } quinacridone (TNTTCzDQA).Mass spectrum molecular ion peak: 1941.2.Chemical formula C is pressed in ultimate analysis
136H
156N
4O
6Calculate: C:84.1%; H:8.1%; N:2.9%; Experimental value: C:84.3%; H:8.0%; N:3.0%.
1，3，8，10-Tetrakis-(naphthalen-1-yl-oxy)-5，12-bis-(4-(1，3
，6，8-tetra-tert-butyl-N-carbazolyl)-decyl)quinacridone
TNTTCzDQA
Example 47:TPDECzOQA
Synthetic similar in the synthetic and example 5 of TPDECzOQA, with 3,5-phenylbenzene aniline replaces 3, the 5-xylidine.With 1,8-two bromooctanes replace 1, and the 4-dibromobutane promptly gets product.
Product 1,3,8,10-tetraphenyl-5,12-two { 4-(3,6-diethyl-N-carbazyl) octyl group } quinacridone (TPDECzOQA).Mass spectrum molecular ion peak: 1284.7.Chemical formula C is pressed in ultimate analysis
92H
92N
4O
2Calculate: C:85.9%; H:7.2%; N:4.4%; Experimental value: C:86.0%; H:7.5%; N:4.2%.
1，3，8，10-Tetraphenyl-5，12-bis-(4-(3，6-diethyl 1，3，8，10-Tetraphenyl-5，12-bis-(4-(1，3，6，8-t
-N-carbazolyl)-octyl)quinacridone etraethyl-N-carbazolyl)-decyl)quinacridone
TPDECzOQA TPTECzDQA
Example 48:TPTECzDQA
Synthetic similar in the synthetic and example 47 of TPTECzDQA, just when synthetic substituted carbazole, the amount of ethyl chloride is increased to six times of carbazole amount, can obtain 1,3,6 by column chromatography again, 8-tetraethyl-carbazole.With 1, the 10-dibromo-decane replaces 1,8-two bromooctanes.Mass spectrum molecular ion peak: 1452.9.Chemical formula C is pressed in ultimate analysis
104H
116N
4O
2Calculate: C:85.9%; H:8.0%; N:3.9%; Experimental value: C:86.0%; H:7.9%; N:4.2%.
Example 49:TPDPCzDQA
TPDPCzDQA's is synthetic similar with example 47, just replaces ethyl chloride with tertiary butyl chloride when synthesizing substituted carbazole.With 1, the 10-dibromo-decane replaces 1,8-two bromooctanes.
Product 1,3,8,10-tetraphenyl-5,12-two { 4-(3,6-dipropyl-N-carbazyl) decyl } quinacridone (TPDPCzDQA).Mass spectrum molecular ion peak: 1396.9.Chemical formula C is pressed in ultimate analysis
100H
108N
4O
2Calculate: C:85.9%; H:7.8%; N:4.0%; Experimental value: C:86.0%; H:7.5%; N:4.2%.
Example 50:TPTPCzDoQA
TPTPCzDoQA's is synthetic similar with example 48, just replaces ethyl chloride with propyl chloride when synthesizing substituted carbazole.With 1, the 12-dibromo-dodecane replaces 1, the 10-dibromo-decane.
Product 1,3,8,10-tetraphenyl-5,12-two { 4-(1,3,6,8-tetrapropyl-N-carbazyl) dodecyl } quinacridone (TPTPCzDoQA).Mass spectrum molecular ion peak: 1621.1.Chemical formula C is pressed in ultimate analysis
116H
140N
4O
2Calculate: C:85.9%; H:8.7%; N:3.5%; Experimental value: C:86.0%; H:8.5%; N:3.8%.
1，3，8，10-Tetraphenyl-5，12-bis-(4-(3，6-diprop 1，3，8，10-Tetraphenyl-5，12-bis-(4-(1，3，6，8-tetrap
yl-N-carbazolyl)-decyl)quinacridone ropyl-N-carbazolyl)-dodecyl)quinacridone
TPDPCzDQA TPTPCzDoQA
Example 51:TPDTCzOQA
Synthetic similar in the synthetic and example 47 of TPDTCzOQA, just when synthesizing substituted carbazole, replace ethyl chloride with tertiary butyl chloride.Promptly get product 1,3,8,10-tetraphenyl-5,12-two { 4-(3,6-di-t-butyl-N-carbazyl) octyl group } quinacridone (TPDTCzOQA).Mass spectrum molecular ion peak: 1396.9.Chemical formula C is pressed in ultimate analysis
100H
108N
4O
2Calculate: C:85.9%; H:7.8%; N:4.0%; Experimental value: C:86.0%; H:7.5%; N:4.2%.
1，3，8，10-Tetraphenyl-5，12-bis-(4-(3，6-di-tert-buty 1，3，8，10-Tetraphenyl-5，12-bis-(4-(1，3，6，8-tetra
l-N-carbazolyl)-octyl)quinacridone -tert-butyl-N-carbazolyl)-dodecyl)quinacridone
TPDTCzOQA TPTTCzDoQA
Example 52:TPTTCzDoQA
Synthetic similar in the synthetic and example 48 of TPTTCzDoQA, just when synthesizing substituted carbazole, replace ethyl chloride with tertiary butyl chloride.With 1, the 12-dibromo-dodecane replaces 1,10 dibromo-decane promptly to get product.
1,3,8,10-tetraphenyl-5,12-two { 4-(1,3,6,8-tetra-tert-N-carbazyl) dodecyl } quinacridone (TPTTCzDoQA).Mass spectrum molecular ion peak: 1733.2.Chemical formula C is pressed in ultimate analysis
124H
156N
4O
2Calculate: C:85.9%; H:9.1%; N:3.2%; Experimental value: C:86.0%; H:8.8%; N:3.6%.
Example 53:TTDECzHQA
Synthetic similar in the synthetic and example 5 of TTDECzHQA, with 3,5-phenylbenzene aniline replaces 3, the 5-xylidine.With 1, the 6-dibromo-hexane replaces 1,4 dibromobutane promptly to get product.
Product 1,3,8,10-four (4-aminomethyl phenyl)-5,12-two { 4-(3,6-diethyl-N-carbazyl) hexyl } quinacridone (TTDECzHQA).Mass spectrum molecular ion peak: 1284.7.Chemical formula C is pressed in ultimate analysis
92H
92N
4O
2Calculate: C:85.9%; H:7.2%; N:4.4%; Experimental value: C:86.0%; H:7.5%; N:4.2%.
1，3，8，10-Tetra-p-tolyl-5，12-bis-(4-(3，6-di
ethyl-N-carbazolyl)-hexyl)quinacridone
TTDECzHQA
1，3，8，10-Tetra-p-tolyl-5，12-bis-(4-(1，3，6，8-tet
raethyl-N-carbazolyl)-decyl)quinacridone
TTTECzDQA
Example 54:TTTECzDQA
Synthetic similar in the synthetic and example 53 of TTTECzDQA, just when synthetic substituted carbazole, the amount of ethyl chloride is increased to six times of carbazole amount, can obtain 1,3,6 by column chromatography again, 8-tetraethyl-carbazole.With 1, the 10-dibromo-decane replaces 1, the 6-dibromo-hexane.Product 1,3,8,10-four (4-aminomethyl phenyl)-5,12-two { 4-(1,3,6,8-tetraethyl--N-carbazyl) decyl } quinacridone (TTTECzDQA).Mass spectrum molecular ion peak: 1509.0.Chemical formula C is pressed in ultimate analysis
108H
124N
4O
2Calculate: C:85.9%; H:8.3%; N:3.7%; Experimental value: C:86.0%; H:8.5%; N:4.2%.
Example 55:TTDPCzOQA's is synthetic
TTDPCzOQA's is synthetic similar with example 53, just replaces ethyl chloride with propyl chloride when synthesizing substituted carbazole.With 1,8-two bromooctanes replace 1, the 6-dibromo-hexane.
Product 1,3,8,10-four (4-aminomethyl phenyl)-5,12-two { 4-(3,6-dipropyl-N-carbazyl) octyl group } quinacridone (TTDPCzOQA).Mass spectrum molecular ion peak: 1396.9.Chemical formula C is pressed in ultimate analysis
100H
108N
4O
2Calculate: C:85.9%; H:7.8%; N:4.0%; Experimental value: C:86.0%; H:7.5%; N:4.2%.
1，3，8，10-Tetra-p-tolyl-5，12-bis-(4-(3，6-dipr
opyl-N-carbazolyl)-octyl)quinacridone
TTDPCzOQA
Example 56:TTTPCzDoQA's is synthetic
TTTPCzDoQA's is synthetic similar with example 54, just replaces ethyl chloride with propyl chloride when synthesizing substituted carbazole.With 1, the 12-dibromo-dodecane replaces 1, the 10-dibromo-decane.
Product 1,3,8,10-four (4-aminomethyl phenyl)-5,12-two { 4-(1,3,6,8-tetrapropyl-N-carbazyl) dodecyl } quinacridone (TTDPCzDoQA).Mass spectrum molecular ion peak: 1677.2.Chemical formula C is pressed in ultimate analysis
120H
148N
4O
2Calculate: C:85.9%; H:8.9%; N:3.3%; Experimental value: C:86.0%; H:8.5%;
1，3，8，10-Tetra-p-tolyl-5，12-bis-(4-(1，3，6，8-tetra
propyl-N-carbazolyl)-dodecyll)quinacridone
TTTPCzDoQA
1，3，8，10-Tetra-p-tolyl-5，12-bis-(4-(3，6-di-tert
-butyl-N-carbazolyl)-hexyl)quinacridone
TTDTCzHQA
Example 57:TTDTCzHQA's is synthetic
Synthetic similar in the synthetic and example 53 of TTDTCzHQA, just when synthesizing substituted carbazole, replace ethyl chloride with tertiary butyl chloride.Product 1,3,8,10-four (4-aminomethyl phenyl)-5,12-two { 4-(3,6-di-t-butyl-N-carbazyl) hexyl } quinacridone (TTDTCzHQA).Mass spectrum molecular ion peak: 1396.9.Chemical formula C is pressed in ultimate analysis
100H
108N
4O
2Calculate: C:85.9%; H:7.8%; N:4.0%; Experimental value: C:86.0%; H:7.5%; N:4.2%.
Example 58:TTTTCzDQA's is synthetic
Synthetic similar in the synthetic and example 54 of TTTTCzDQA, just when synthesizing substituted carbazole, replace ethyl chloride with tertiary butyl chloride.Product 1,3,8,10-four (4-aminomethyl phenyl)-5,12-two { 4-(1,3,6,8-tetra-tert-N-carbazyl) decyl } quinacridone (TTTTCzDQA).Mass spectrum molecular ion peak: 1733.2.Chemical formula C is pressed in ultimate analysis
124H
156N
4O
2Calculate: C:85.9%; H:9.1%; N:3.2%; Experimental value: C:86.0%; H:9.2%; N:3.2%.
1，3，8，10-Tetra-p-tolyl-5，12-bis-(4-(3，6-di-tert
-butyl-N-carbazolyl)-decyl)quinacridone
TTTTCzDQA
Example 59: luminescent device [ITO/Cu-Pc/NPB/Alq:(I)/LiF/Al]
Be coated with ITO (tin indium oxide, positive pole) plates one deck Cu-Pc (150_) on the glass substrate earlier, hole transmission layer NPB (500_), luminescent layer Alq:(I on the evaporation successively afterwards) (600_) (wherein (I) represents compound of the present invention, and its concentration is 0.5-5wt%), electron injecting layer LiF (15_) and metal electrode Al (2000_).Keeping vacuum tightness in evaporate process is 4 * 10
-6Torr.
Example 60: with TMDECzBQA is the luminescent device of luminescent layer
The luminescent device structure is [ITO/Cu-Pc (150_)/NPB (500_)/Alq:TMDECzBQA (600_)/LiF (15_)/Al (2000_)], and the doping content scope of luminescent material TMDECzBQA in Alq is 0.5-5wt%.Device efficiency has very high efficient (10.3-20.2cd/A) in the concentration range of broad.The luminous peak position of device is green emitting near 535nm, maximum brightness is 65000cd/m
2
1，3，8，10-Tetramethyl-5，12-bis-{4-(3，6-diethyl-N-carbazolyl)-butyl)quinacridone
TMDECzBQA
Example 61: with TMDPCzBQA is the luminescent device of luminescent layer
The luminescent device structure is [ITO/Cu-Pc (150_)/NPB (500_)/Alq:TMDPCzBQA (600_)/LiF (15_)/Al (2000_)], the doping content scope of luminescent material TMDPCzBQA in Alq is 0.5-5wt%, and device efficiency has very high efficient (11.1-21.5cd/A) in the concentration range of broad.The luminous peak position of device is green emitting near 536nm, maximum brightness is 54000cd/m
2
1，3，8，10-Tetramethyl-5，12-bis-{4-(3，6-dipropyl-N-carbazolyl)-butyl}quinacridone
TMDPCzBQA
Example 62: with TMDTCzBQA is the luminescent device of luminescent layer
The luminescent device structure is [ITO/Cu-Pc (150_)/NPB (500_)/Alq:TMDTCzBQA (600_)/LiF (15_)/Al (2000_)], the doping content scope of luminescent material TMDTCzBQA in Alq is 0.5-5wt%, and device efficiency has very high efficient (9.6-19.3cd/A) in the concentration range of broad.The luminous peak position of device is green emitting near 530nm, maximum brightness is 52000cd/m
2
1，3，8，10-Tetramethyl-5，12-bis-{4-(3，6-di-tert-butyl-N-carbazolyl)-butyl}quinacridone
TMDTCzBQA
Example 63: with TMTTCzHQA is the luminescent device of luminescent layer
The luminescent device structure is [ITO/Cu-Pc (150_)/NPB (500_)/Alq:TMTTCzHQA (600_)/LiF (15_)/Al (2000_)], the doping content scope of luminescent material TMTTCzHQA in Alq is 0.5-5wt%, and device efficiency has very high efficient (9.6-19.5cd/A) in the concentration range of broad.The luminous peak position of device is green emitting near 535nm, maximum brightness is 46000cd/m
2
1，3，8，10-Tetramethyl-5，12-bis- {4-(1，3，6，8-tetra-tert-butyl-N-carbazolyl)-hexyl}quinacridone
TMTTCzHQA
Example 64: with TMDCzBQA is the luminescent device of luminescent layer
The luminescent device structure is [ITO/Cu-Pc (150_)/NPB (500_)/Alq:TMDECzBQA (600_)/LiF (15_)/Al (2000_)], the doping content scope of luminescent material TMDCzBQA in Alq is that the 0.5-5wt% device efficiency has very high efficient in the concentration range of broad, and be as shown in table 1.The luminous peak position of device is green emitting near 536nm, maximum brightness is 53000cd/m
2
Device efficiency under table 1. different levels of doping
| Doping content (wt%) | 0.5 | 1.0 | 2.0 | 3.0 | 4.0 | 5.0 |
| Efficient (cd/A) | 21 | 19.0 | 18 | 16 | 12 | 11 |
1，3，8，10-Tetramethyl-5，12-bis-{4-N-carbazolyl)-butyl}quinacridone
TMDCzBQA
Claims (8)
1, the quinacridone-carbazole compound shown in the general formula (I),
R wherein
1And R
2Can be the same or different R
1And R
2Be H or C
1-4Alkyl; R
3, R
4, R
5And R
6Identical, it is C
1-C
11Alkyl, C
1-C
11Alkoxyl group, phenyl, phenylol or halogen, n=4-18.
2, quinacridone-carbazole compound as claimed in claim 1 is characterized in that: R
3, R
4, R
5And R
6Identical, it is C
1-C
6Alkyl or C
1-C
6Alkoxyl group, n=4-10.
3, the quinacridone-carbazole compound that is shown below,
4, the quinacridone-carbazole compound that is shown below,
5, the application of the described quinacridone-carbazole compound of claim 1 aspect the preparation organic electroluminescence device.
6, the application of quinacridone-carbazole compound as claimed in claim 5 aspect the preparation organic electroluminescence device, it is characterized in that: electroluminescent device has one or more active coatings, has at least one deck to contain the described compound of one or more claims 1 (I) in these active coatings.
7, the application of quinacridone-carbazole compound as claimed in claim 6 aspect the preparation organic electroluminescence device, it is characterized in that: active coating is a light-emitting layer and/or a migrating layer and/or an electric charge injection layer.
8, claim 2,3,4 any one described quinacridone-carbazole compound are in the application that is used to prepare aspect the organic electroluminescence device.
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| US7842406B2 (en) | 2007-12-14 | 2010-11-30 | Global Oled Technology Llc | OLED device with substituted acridone compounds |
| CN102060854A (en) * | 2010-11-25 | 2011-05-18 | 吉林大学 | Nitrile substituted quinacridone compounds and application thereof in organic solar cell |
| CN107068881B (en) * | 2016-04-25 | 2019-12-03 | 中节能万润股份有限公司 | A kind of organic electroluminescence device containing acridones compound and its application |
| CN108484596B (en) * | 2018-03-09 | 2020-05-19 | 安徽科技学院 | Preparation method of organic luminescent material based on quinacridone and luminescent device thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5876864A (en) * | 1996-12-31 | 1999-03-02 | Korea Institute Of Science And Technology | Fluorene-based alternating polymers containing acetylene group and electroluminescence element using the same |
| US6630254B2 (en) * | 2001-04-10 | 2003-10-07 | National Research Council Of Canada | Conjugated polycarbazole derivatives in Organic Light Emitting Diodes |
| US6660410B2 (en) * | 2000-03-27 | 2003-12-09 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence element |
| US6670054B1 (en) * | 2002-07-25 | 2003-12-30 | Xerox Corporation | Electroluminescent devices |
| CN1482127A (en) * | 2003-07-08 | 2004-03-17 | 吉林大学 | Quinacridone derivant and application in organic electroluminescent device thereof |
-
2004
- 2004-12-10 CN CNB200410011335XA patent/CN1300140C/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5876864A (en) * | 1996-12-31 | 1999-03-02 | Korea Institute Of Science And Technology | Fluorene-based alternating polymers containing acetylene group and electroluminescence element using the same |
| US6660410B2 (en) * | 2000-03-27 | 2003-12-09 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence element |
| US6630254B2 (en) * | 2001-04-10 | 2003-10-07 | National Research Council Of Canada | Conjugated polycarbazole derivatives in Organic Light Emitting Diodes |
| US6670054B1 (en) * | 2002-07-25 | 2003-12-30 | Xerox Corporation | Electroluminescent devices |
| CN1482127A (en) * | 2003-07-08 | 2004-03-17 | 吉林大学 | Quinacridone derivant and application in organic electroluminescent device thereof |
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