CN112110919A - Chiral thermal activation delayed fluorescent material and preparation method and application thereof - Google Patents
Chiral thermal activation delayed fluorescent material and preparation method and application thereof Download PDFInfo
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- CN112110919A CN112110919A CN202010838369.5A CN202010838369A CN112110919A CN 112110919 A CN112110919 A CN 112110919A CN 202010838369 A CN202010838369 A CN 202010838369A CN 112110919 A CN112110919 A CN 112110919A
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- delayed fluorescence
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- activated delayed
- fluorescence material
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- 239000000463 material Substances 0.000 title claims abstract description 101
- 230000003111 delayed effect Effects 0.000 title claims abstract description 72
- 238000002360 preparation method Methods 0.000 title abstract description 31
- 238000007725 thermal activation Methods 0.000 title abstract description 28
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 230000000694 effects Effects 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 7
- -1 phenylmethylene, naphthylmethylene, thienylmethylene, furanylmethylene Chemical group 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 8
- 238000007112 amidation reaction Methods 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000003446 ligand Substances 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical class C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 3
- 125000000958 aryl methylene group Chemical group 0.000 claims description 3
- BYVCTYDTPSKPRM-UHFFFAOYSA-N naphthalene-1-carbonyl naphthalene-1-carboxylate Chemical class C1=CC=C2C(C(OC(=O)C=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 BYVCTYDTPSKPRM-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000004166 substituted arylmethylene group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000001639 phenylmethylene group Chemical group [H]C(=*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 230000010287 polarization Effects 0.000 abstract description 10
- 150000002894 organic compounds Chemical class 0.000 abstract description 8
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 230000009286 beneficial effect Effects 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
- 238000002347 injection Methods 0.000 description 22
- 239000007924 injection Substances 0.000 description 22
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000012043 crude product Substances 0.000 description 18
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- 230000000903 blocking effect Effects 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- KXMHPELKLKNUCC-UHFFFAOYSA-N 9-(3-carbazol-9-ylphenyl)carbazole-3-carbonitrile Chemical compound N#CC1=CC2=C(C=C1)N(C1=C2C=CC=C1)C1=CC(=CC=C1)N1C2=C(C=CC=C2)C2=C1C=CC=C2 KXMHPELKLKNUCC-UHFFFAOYSA-N 0.000 description 11
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 11
- 238000004587 chromatography analysis Methods 0.000 description 10
- 239000011259 mixed solution Substances 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000000151 deposition Methods 0.000 description 5
- 238000004020 luminiscence type Methods 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
- CDOYZTOFTGTGBC-UHFFFAOYSA-N 1-tert-butyl-4-phenylbenzene Chemical group C1=CC(C(C)(C)C)=CC=C1C1=CC=CC=C1 CDOYZTOFTGTGBC-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000009987 spinning Methods 0.000 description 4
- DTUOTSLAFJCQHN-UHFFFAOYSA-N 4-bromo-1,8-naphthalic anhydride Chemical compound O=C1OC(=O)C2=CC=CC3=C2C1=CC=C3Br DTUOTSLAFJCQHN-UHFFFAOYSA-N 0.000 description 3
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Inorganic materials O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- IVURTNNWJAPOML-UHFFFAOYSA-N 5,10-dihydrophenazine Chemical compound C1=CC=C2NC3=CC=CC=C3NC2=C1 IVURTNNWJAPOML-UHFFFAOYSA-N 0.000 description 2
- HMFPRCSANHVXES-UHFFFAOYSA-N 9,9'-spirobi[10h-acridine] Chemical compound C12=CC=CC=C2NC2=CC=CC=C2C11C2=CC=CC=C2NC2=CC=CC=C21 HMFPRCSANHVXES-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- RFDGVZHLJCKEPT-UHFFFAOYSA-N tris(2,4,6-trimethyl-3-pyridin-3-ylphenyl)borane Chemical compound CC1=C(B(C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C(C)=CC(C)=C1C1=CC=CN=C1 RFDGVZHLJCKEPT-UHFFFAOYSA-N 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 description 1
- RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 1
- XBWOPGDJMAJJDG-SSDOTTSWSA-N (1r)-1-cyclohexylethanamine Chemical compound C[C@@H](N)C1CCCCC1 XBWOPGDJMAJJDG-SSDOTTSWSA-N 0.000 description 1
- XBWOPGDJMAJJDG-ZETCQYMHSA-N (1s)-1-cyclohexylethanamine Chemical compound C[C@H](N)C1CCCCC1 XBWOPGDJMAJJDG-ZETCQYMHSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
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- 238000010168 coupling process Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- SORXVYYPMXPIFD-UHFFFAOYSA-N iron palladium Chemical compound [Fe].[Pd] SORXVYYPMXPIFD-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000003325 tomography Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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Abstract
The invention discloses a chiral thermal activation delayed fluorescent material and a preparation method and application thereof, wherein the structural general formula of the chiral thermal activation delayed fluorescent material is
In the formulas I to IV, R is chiral alkyl or chiral aralkyl, and R' are independently selected from aryl or heteroaryl with electron donating effect. The chiral organic compound with the structure and taking the 1, 8-naphthalimide as a parent nucleus has good Thermal Activation Delayed Fluorescence (TADF) characteristics and high asymmetric excess value, is beneficial to obtaining circularly polarized light with high asymmetric factor, and can obtain high device luminous efficiency when being used in a luminous layer of an OLED. The preparation method of the chiral thermal activation delayed fluorescence material is simple, the raw materials are easy to obtain, and a simple and effective solution is provided for obtaining the circular polarization light-emitting device with low manufacturing cost, high efficiency and large asymmetric factor.
Description
Technical Field
The invention relates to the field of electroluminescent materials, in particular to a chiral thermal activation delayed fluorescent material and a preparation method and application thereof.
Background
Organic Light-Emitting diodes (OLEDs), which are a new type of flat panel display devices, have attracted attention in the fields of flat panel display and lighting due to their advantages of self-luminescence, high flexibility, high resolution, high efficiency, fast response time, wide temperature range, low driving voltage, and low power consumption. However, current OLEDs typically use polarizers and 1/4 waveplates to reduce ambient reflections to achieve higher image contrast, resulting in half of the OLED light being lost. Therefore, designing the luminescent material as a molecule having circularly polarized luminescence can avoid absorption by the polarizer, thereby improving light extraction efficiency to reduce power consumption of the OLED display. Meanwhile, the circular polarization luminescent material can also be used in the leading-edge technologies such as 3D display, information storage and processing, electromagnetic coupling devices, tomography and the like.
Compared with the OLED based on the traditional luminescent material, the device based on the circular polarization luminescent material has less research, and the External Quantum Efficiency (EQE) and the large asymmetry factor (g) should be realized at the same time at presentEL) Still a major challenge.
Accordingly, the prior art is yet to be improved and developed.
Disclosure of Invention
In view of the defects of the prior art, the present invention aims to provide a chiral thermally activated delayed fluorescence material, a preparation method and an application thereof, and aims to solve the problem that the conventional OLED based on a circular polarization luminescent material does not have high external quantum efficiency and large asymmetry factor.
The technical scheme of the invention is as follows:
in a first aspect, the present invention provides a chiral thermal activation delayed fluorescence material, wherein the structural general formula of the chiral thermal activation delayed fluorescence material is
In the formulas I to IV, R is chiral alkyl or chiral aralkyl, and R' are independently selected from aryl or heteroaryl with electron donating effect.
In a second aspect, the present invention provides a method for preparing the chiral thermally activated delayed fluorescence material as described above, according to the reaction formula
The method comprises the following steps:
E. carrying out amidation reaction on chiral primary amine A and halogenated 1, 8-naphthalic anhydride B in a first solvent under an inert atmosphere, and after the reaction is finished, carrying out purification treatment to obtain chiral halogenated 1, 8-naphthalimide C;
wherein, the chiral primary amine A is
R is chiral alkyl or chiral aralkyl; halogenated 1, 8-naphthalic anhydrides B are
X ═ Br or I; chiral halogenated 1, 8-naphthalimides C is
F. Under the inert atmosphere, carrying out coupling reaction on chiral halogenated 1, 8-naphthalimide C and a compound D containing R 'or R' in a second solvent under the action of a palladium catalyst, an organophosphorus ligand and an alkaline substance, and after the reaction is finished, carrying out purification treatment to obtain the chiral thermally activated delayed fluorescent material;
wherein the compound D containing R 'or R' is
R'、R”Independently selected from aryl or heteroaryl groups having an electron donating effect.
In a third aspect, the present invention provides an organic light emitting diode comprising an anode, a cathode, and a light emitting layer disposed between the anode and the cathode, wherein the material of the light emitting layer comprises the chiral thermally activated delayed fluorescence material as described above.
Has the advantages that: the chiral organic compound with the structure and taking the 1, 8-naphthalimide as a parent nucleus has good Thermal Activation Delayed Fluorescence (TADF) characteristics and high asymmetric excess value, is beneficial to obtaining circularly polarized light with high asymmetric factor, and can obtain high device luminous efficiency when being used in a luminous layer of an OLED. In addition, the preparation method of the chiral thermal activation delayed fluorescence material is simple, raw materials are easy to obtain, and a simple and effective solution is provided for obtaining a circular polarization light-emitting device with low manufacturing cost, high efficiency and large asymmetric factor.
Drawings
Fig. 1 is a schematic structural diagram of an upright OLED according to an embodiment of the present invention.
FIG. 2 is a graph comparing the asymmetry factors of circularly polarized light of OLED-103 and OLED-104 in example 11 of the present invention.
Detailed Description
The invention provides a chiral thermal activation delayed fluorescence material and a preparation method and application thereof, and the invention is further described in detail below in order to make the purpose, technical scheme and effect of the invention clearer and more clear. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The embodiment of the invention provides a chiral thermal activation delayed fluorescence material, which has a structural general formula
In the formulas I to IV, R is chiral alkyl or chiral aralkyl, and R' are independently selected from aryl or heteroaryl with electron donating effect.
In the embodiment, the chiral organic compound with the structure and taking 1, 8-naphthalimide as a parent nucleus has good Thermal Activation Delayed Fluorescence (TADF) characteristics and high asymmetric excess value, is beneficial to obtaining circularly polarized light with high asymmetric factor, and can obtain high device luminous efficiency when being used in a light emitting layer of an OLED.
Specifically, the chiral organic compound with the structure comprises an electron donor with strong electron donating capability and a naphthalimide core with strong electron pulling capability as electron acceptors, and due to the rigid structures and large steric hindrance of the electron donor and the electron acceptors, the torsion angle between the electron donor and the electron acceptors in the molecule can be increased, so that the extremely poor energy (delta E) of a singlet state and a triplet state is obtainedST) Further, higher reverse inter-system crossing (RISC) rate and higher energy utilization rate are realized; by introducing a chiral substituent R on naphthalimide as an electron acceptor, R can be used as a protective group of N and provides a chiral environment required by molecules, and the preparation of the chiral TADF material is realized. In addition, the chiral organic compound containing 1, 8-naphthalimide and having the structure has larger conjugation area, and can improve the overlapping integral area of radiative transition, thereby obtaining higher oscillator strength (f); due to the unique configuration and radiation transition mode of the molecule, the crystal has higher plane transition dipole moment ratio and has certain gain effect on light coupling-out in the device.
In one embodiment, R may be selected from, but is not limited to
R1Can be selected from but not limited to C2～C20Alkyl of (C)3～C10Cycloalkyl of, C5～C20Arylmethylene or C of5～C20Substituted arylmethylene of (a);
Ar1can be selected from, but not limited to, phenyl (Ph), naphthyl, thienyl, furyl, pyridyl, C1～C6Alkyl of (C)2～C6Alkenyl of, C2～C6Alkynyl of (A), C1～C6At least one substituted phenyl, naphthyl, thienyl, furyl or pyridyl group. In addition, the curved key
For R only, curved bonds
The position is the connection position of R.
In one embodiment, said C5～C20Arylmethylene of (a) may be selected from, but is not limited to, phenylmethylene, naphthylmethylene, thienylmethylene, furanylmethylene, or pyridylmethylene;
said C is5～C20The substituted arylmethylene group of (A) can be selected from but is not limited to C1～C6Alkyl of (C)2～C6Alkenyl of, C2～C6Alkynyl of (A), C1～C6And at least one substituted phenylmethylene, naphthylmethylene, thienylmethylene, furylmethylene, pyridylmethylene of (a).
In one embodiment, R' may be selected from, but is not limited to
R2Can be selected from but not limited to hydrogen, C1～C4Alkyl of (C)3～C6Cycloalkyl of, C4～C20Aryl or C of4～C20Substituted aryl of (a);
Ar2can be selected from, but not limited to, phenyl, naphthyl, thienyl, furyl, pyridyl, C1～C4Alkyl of (C)2～C6Alkenyl of, C2～C6Alkynyl of (A), C1～C6Alkoxy and diPhenyl, naphthyl, thienyl, furyl and pyridyl substituted by at least one of anilino. It should be noted that the upper curve key
For R' only, curved bonds
The position is the linking position of R'.
In one embodiment, said C4～C20Aryl of (a) may be selected from, but not limited to, phenyl, naphthyl, thienyl, furyl, or pyridyl;
said C is4～C20Substituted aryl of (A) may be selected from, but not limited to, C1～C4Alkyl of (C)2～C6Alkenyl of, C2～C6Alkynyl of (A), C1～C6At least one substituted phenyl, naphthyl, thienyl, furyl or pyridyl group.
In one embodiment, R' may be selected from, but is not limited to
In addition, the curved key
For R "only, curved bonds
The position is the linking position of R'.
In one embodiment, the chiral thermally activated delayed fluorescence material may be, but is not limited to
The compounds have obvious D-A structure, and the compounds have small energy range difference (delta E) of singlet state and triplet stateST) Is favorable for effectively realizing a reverse systemCross-talk, thereby obtaining highly efficient thermally induced delayed fluorescence (TADF) characteristics; meanwhile, the light-emitting diode has very high asymmetric excess value, and is more favorable for obtaining circular polarization luminescence. Preferably, the chiral thermally activated delayed fluorescence material is
The embodiment of the invention also provides a preparation method of the chiral thermal activation delayed fluorescence material, which is based on the reaction formula
The method comprises the following steps:
E. carrying out amidation reaction on chiral primary amine A and halogenated 1, 8-naphthalic anhydride B in a first solvent under an inert atmosphere, and after the reaction is finished, carrying out purification treatment to obtain chiral halogenated 1, 8-naphthalimide C;
wherein, the chiral primary amine A is
R is chiral alkyl or chiral aralkyl; halogenated 1, 8-naphthalic anhydrides B are
X ═ Br or I; chiral halogenated 1, 8-naphthalimides C is
F. Under the inert atmosphere, carrying out coupling reaction on chiral halogenated 1, 8-naphthalimide C and a compound D containing R 'or R' in a second solvent under the action of a palladium catalyst, an organophosphorus ligand and an alkaline substance, and after the reaction is finished, carrying out purification treatment to obtain the chiral thermally activated delayed fluorescent material;
wherein the compound D containing R 'or R' is
R 'and R' are independently selected from aryl or heteroaryl groups having an electron donating effect.
In the embodiment, the preparation method of the chiral thermal activation delayed fluorescence material is simple, raw materials are easy to obtain, and a simple and effective solution is provided for obtaining a circular polarization light-emitting device with low manufacturing cost, high efficiency and large asymmetric factor.
In one embodiment, the inert atmosphere may be, but is not limited to, nitrogen (N)2) An atmosphere or an argon (Ar) atmosphere.
In one embodiment, in step E, the temperature of the amidation reaction is 110 to 150 ℃, such as 110 ℃, 120 ℃, 150 ℃ and the like; the amidation reaction time is 12-48 h, such as 12h, 24h, 48h and the like. The molar ratio of the chiral primary amine A to the halogenated 1, 8-naphthalic anhydride B is 0.8-1.5: 1, and the preferable molar ratio is 1.1: 1. The first solvent may be selected from, but is not limited to, one of toluene, acetic acid, N-dimethylformamide, and chlorobenzene. The purification treatment specifically comprises: removing volatile components in the reaction liquid, carrying out column chromatography separation to obtain a crude product, and recrystallizing the crude product.
In one embodiment, in step F, the temperature of the coupling reaction is 80 to 150 ℃, such as 80 ℃, 110 ℃, 120 ℃, 150 ℃ and the like; the coupling reaction time is 12-48 h, such as 12h, 24h, 48h and the like.
In one embodiment, in step F, when the compound D containing R 'or R' is
When the catalyst is used, the molar ratio of the chiral halogenated 1, 8-naphthalimide C to the palladium catalyst to the organic phosphine ligand to the alkaline substance to the compound D containing R 'or R' is 0.8-1.2: 0.01-0.1: 0.02-0.2: 1.0-2.0: 1, preferably in a molar ratio of 1.1: 0.02: 0.04:1.1: 1; when the compound D containing R 'or R' is
When the compound is a chiral halogenated 1, 8-naphthalimide C, a palladium catalyst, an organic phosphine ligand, an alkaline substance, a compound containing R' or RThe molar ratio of the substances D is 2.0-3.0: 0.02-0.2: 0.04-0.4: 2.0-3.0: 1, preferably in a molar ratio of 2.2:0.04:0.08:2.2: 1. The palladium catalyst can be selected from one or more of palladium acetate, tris (dibenzylidene-BASE acetone) dipalladium and 1, 1-bis (diphenylphosphino) dicyclopentadieny iron palladium dichloride. The organophosphine ligand may be selected from, but is not limited to, one or more of tri-tert-butylphosphine tetrafluoroborate, triphenylphosphine, and 1,1' -bis (diphenylphosphino) ferrocene. The basic substance may be selected from, but is not limited to, one or more of sodium tert-butoxide, potassium carbonate and cesium carbonate. The second solvent may be selected from, but is not limited to, one of toluene, xylene, tetrahydrofuran, and ethanol. The purification treatment specifically comprises: adding water into the reaction solution to quench and react, extracting, collecting an organic phase, removing volatile components in the organic phase, separating by column chromatography to obtain a crude product, and recrystallizing the crude product.
The embodiment of the invention provides an organic light-emitting diode, which comprises an anode, a cathode and a light-emitting layer arranged between the anode and the cathode, wherein the material of the light-emitting layer comprises the chiral thermally activated delayed fluorescence material.
In this embodiment, the chiral TADF material can be used as a material of a light-emitting layer in an OLED, and the chiral TADF material can be used in combination with a suitable host material to improve the light-emitting efficiency of the OLED, and can achieve 10-1The asymmetric factor of the level circular polarization luminescence provides a solution for a luminescent device with low manufacturing cost and high efficiency, and can be widely applied to the field of organic electroluminescence.
In one embodiment, the material of the light emitting layer is composed of 0.1 to 100 wt% of the chiral thermally activated delayed fluorescence material and 0 to 99.9 wt% of an organic functional material.
In one embodiment, the organic functional material may be selected from, but not limited to, one of a hole injection material, a hole transport material, a hole blocking material, an electron injection material, an electron transport material, an electron blocking material, an exciton blocking material, a fluorescent material, a phosphorescent material, a host material, and an organic dye.
In one embodiment, the chiral thermally activated delayed fluorescence material is a guest material and the organic functional material is a host material.
In one embodiment, the electroluminescent wavelength of the organic light emitting diode is 550 to 650 nm.
In one embodiment, the organic light emitting diode may be an inverted OLED or an upright OLED; of course, if necessary, a hole injection layer and/or a hole transport layer may be further disposed between the anode and the light emitting layer, and when both the hole injection layer and the hole transport layer are disposed, the hole injection layer is disposed near the anode side, and the hole transport layer is disposed near the light emitting layer side; when the electron injection layer and the electron transport layer are arranged at the same time, the electron injection layer is arranged close to one side of the cathode, and the electron transport layer is arranged close to one side of the luminous layer. Further, an electron/exciton blocking layer may be further disposed between the hole transport layer and the light emitting layer, and a hole/exciton blocking layer may be further disposed between the electron transport layer and the light emitting layer. The OLED of this embodiment will be described with reference to an OLED further provided with a hole injection layer, a hole transport layer, an electron/exciton blocking layer, an electron transport layer, and an electron injection layer, and as shown in fig. 1, the OLED sequentially includes, from bottom to top: an anode 1, a hole injection layer 2, a hole transport layer 3, an electron/exciton blocking layer 4, a light emitting layer 5, an electron transport layer 6, an electron injection layer 7 and a cathode 8. The anode, the cathode, the hole injection layer, the hole transport layer, the electron/exciton blocking layer, the electron injection layer, the electron transport layer and the thickness of the organic light emitting diode can be set according to the existing organic light emitting diode.
The present invention will be described in detail below with reference to specific examples.
Example 1 chiral thermally activated delayed fluorescence material 97: preparation of (S) -4- [10- (4' -tert-butyl-1, 1' -biphenyl) -9,9' -spirodiazanyl ] -N- (1-cyclohexylethyl) -1, 8-naphthalimide
(1) According to the reaction formula
Intermediate C2-1 (chemical name ((S) -4-bromo-N- (1-cyclohexylethyl) -1, 8-naphthalimide) was prepared according to the following procedure:
a250 mL flask was charged with 4-bromo-1, 8-naphthalenedicarboxylic anhydride (B-1, 2.8g,10mmol), (S) -1-cyclohexylethylamine (A2-1, 1.4g,11mmol) and 50mL of toluene, and the mixture was refluxed under Ar for 24 hours. Cooling to room temperature, removing solvent by spinning, performing column chromatography to obtain crude product, and recrystallizing with dichloromethane and n-hexane to obtain 3.43g of intermediate product C2-1 as white powder. MS (EI) M/z 386.6[ M ]+]。
(2) According to the reaction formula
The chiral thermally activated delayed fluorescence material 97 was prepared as follows:
a50 mL three-necked flask was charged with (S) -4-bromo-N- (1-cyclohexylethyl) -1, 8-naphthalimide (C2-1, 1.93g,5mmol), 10- (4' -tert-butyl-1, 1' -biphenyl) -9,9' -spirobiacridine (D-1-1, 2.77g,5mmol), palladium acetate (23mg,0.1mmol), tri-tert-butylphosphine tetrafluoroborate (58mg,0.2mmol), sodium tert-butoxide (528mg,5.5mmol), and 15mL of toluene, and reacted at 110 ℃ for 24 hours under Ar atmosphere. Cooling to room temperature, pouring the mixed solution into water, extracting with dichloromethane, collecting an organic phase, washing with water for several times, and performing chromatography by using a chromatographic column to obtain a crude product, and recrystallizing dichloromethane and n-hexane to obtain 4.05g of the chiral thermal activation delayed fluorescent material 97 as orange powder. MS (EI) M/z 860.3[ M ]+]。
Example 2 chiral thermally activated delayed fluorescence material 98: preparation of (R) -4- [10- (4' -tert-butyl-1, 1' -biphenyl) -9,9' -spirodiazanyl ] -N- (1-cyclohexylethyl) -1, 8-naphthalimide
(1) According to the reaction formula (2-1)
Intermediate C1-1 (chemical name (R) -4-bromo-N- (1-cyclohexylethyl) -1, 8-naphthalimide) was prepared according to the following procedure:
into a 250mL flask was added4-bromo-1, 8-naphthalenedicarboxylic anhydride (B-1, 2.8g,10mmol), (R) -1-cyclohexylethylamine (A1-1, 1.4g,11mmol) and 50mL of toluene were added, and the mixture was refluxed under Ar atmosphere for 24 hours. Cooling to room temperature, removing solvent by spinning, performing column chromatography to obtain crude product, and recrystallizing with dichloromethane and n-hexane to obtain 3.32g of intermediate product C1-1 as white powder. MS (EI) M/z 386.4[ M ]+]。
(2) According to the reaction formula
The chiral thermally activated delayed fluorescence material 98 was prepared as follows:
a50 mL three-necked flask was charged with (R) -4-bromo-N- (1-cyclohexylethyl) -1, 8-naphthalimide (C1-1, 1.93g,5mmol), 10- (4' -tert-butyl-1, 1' -biphenyl) -9,9' -spirobiacridine (D1-1, 2.77g,5mmol), palladium acetate (23mg,0.1mmol), tri-tert-butylphosphine tetrafluoroborate (58mg,0.2mmol), sodium tert-butoxide (528mg,5.5mmol), and 15mL of toluene, and reacted at 110 ℃ for 24 hours under Ar atmosphere. Cooling to room temperature, pouring the mixed solution into water, extracting with dichloromethane, collecting an organic phase, washing with water for several times, and carrying out chromatography by using a chromatographic column to obtain a crude product, and recrystallizing with dichloromethane and n-hexane to obtain 4.01g of the chiral thermal activation delayed fluorescent material 98 which is orange powder. MS (EI) M/z 860.3[ M ]+]。
Example 3 chiral thermally activated delayed fluorescence material 103: preparation of (S) -4- (9, 9-diphenylacridinyl) -N- (1-phenylethyl) -1, 8-naphthalimide
(1) According to the reaction formula
Intermediate C2-2 (chemical name (S) -4-bromo-N- (1-phenylethyl) -1, 8-naphthalimide) was prepared according to the following procedure:
a250 mL flask was charged with 4-bromo-1, 8-naphthalic anhydride (B-1, 2.8g,10mmol), (S) -1-phenylethylamine (A2-2, 1.33g,11mmol) and 50mL of toluene, and heated under reflux for 24 hours under Ar. Cooling to room temperature, removing solvent by spinning, performing chromatographic column chromatography to obtain a crude product, and recrystallizing dichloromethane and n-hexane to obtain 3.46g of an intermediate product C2-2 as white powder. MS (EI) M/z 379.5[ M ]+]。
(2) According to the reaction formula
The chiral thermally activated delayed fluorescence material 103 is prepared as follows:
a50 mL three-necked flask was charged with (S) -4-bromo-N- (1-phenylethyl) -1, 8-naphthalimide (C2-2, 1.9g,5mmol), 9-dimethylacridine (D1-2, 1.15g,5.5mmol), palladium acetate (23mg,0.1mmol), tri-tert-butylphosphine tetrafluoroborate (58mg,0.2mmol), sodium tert-butoxide (528mg,5.5mmol), and 15mL of toluene, and reacted at 110 ℃ for 24 hours under Ar atmosphere. And cooling to room temperature, pouring the mixed solution into water, extracting with dichloromethane, collecting an organic phase, washing with water for several times, and carrying out chromatography by using a chromatographic column to obtain a crude product, and recrystallizing with dichloromethane and n-hexane to obtain the chiral thermal activation delayed fluorescence material 103 which is 2.35g of orange powder. MS (EI) M/z 508.6[ M ]+]. Example 4 chiral thermally activated delayed fluorescence material 104: preparation of (R) -4- (9, 9-diphenylacridinyl) -N- (1-phenylethyl) -1, 8-naphthalimide
(1) According to the reaction formula
Intermediate C1-2 (chemical name (S) -4-bromo-N- (1-phenylethyl) -1, 8-naphthalimide) was prepared according to the following procedure:
a250 mL flask was charged with 4-bromo-1, 8-naphthalic anhydride (B-1, 2.8g,10mmol), (R) -1-phenylethylamine (1.33g,11mmol) and 50mL of toluene, and heated under reflux for 24 hours under Ar. Cooling to room temperature, removing the solvent by spinning, performing chromatographic column chromatography to obtain a crude product, and recrystallizing dichloromethane and n-hexane to obtain 3.21g of a product C1-2 as white powder. MS (EI) M/z 379.7[ M ]+]。
(2) According to the reaction formula
The chiral thermally activated delayed fluorescence material 104 was prepared as follows:
a50 mL three-necked flask was charged with (R) -4-bromo-N- (1-phenylethyl) -1, 8-naphthalimide (C1-2, 1.9g,5mmol), 9-dimethylacridine (D1-2, 1.15g,5.5mmol), palladium acetate (23 m)g,0.1mmol), tri-tert-butylphosphine tetrafluoroborate (58mg,0.2mmol), sodium tert-butoxide (528mg,5.5mmol) and 15mL of toluene were reacted at 110 ℃ for 24 hours under Ar atmosphere. And cooling to room temperature, pouring the mixed solution into water, extracting with dichloromethane, collecting an organic phase, washing with water for several times, and carrying out chromatography by using a chromatographic column to obtain a crude product, and recrystallizing dichloromethane and n-hexane to obtain the chiral thermal activation delayed fluorescence material 104 which is 2.35g of orange powder. MS (EI) M/z 508.2[ M+]。
Example 5 chiral thermally activated delayed fluorescence material 277: preparation of (S, S) -10,10 '-bis [4-N- (1-cyclohexylethyl) -1, 8-naphthalimide ] -9,9' -spirobiacridine
According to the reaction formula
The preparation method comprises the following steps:
a50 mL three-necked flask was charged with (S) -4-bromo-N- (1-cyclohexylethyl) -1, 8-naphthalimide (C2-1, 2.12g,5.5mmol), 10H,10'H-9,9' -spirobiacridine (D3-1, 0.86g,2.5mmol), palladium acetate (23mg,0.1mmol), tri-tert-butylphosphine tetrafluoroborate (58mg,0.2mmol), sodium tert-butoxide (528mg,5.5mmol), and 15mL of toluene, and reacted at 110 ℃ for 24H under Ar atmosphere. And cooling to room temperature, pouring the mixed solution into water, extracting by using dichloromethane, collecting an organic phase, washing for a plurality of times, and carrying out chromatography by using chromatographic column to obtain a crude product, and recrystallizing by using dichloromethane and normal hexane to obtain 2.13g of the chiral thermal activation delayed fluorescent material 277, which is orange powder. MS (EI) M/z 957.3[ M ]+]。
Example 6 chiral thermally activated delayed fluorescence material 278: preparation of (R, R) -10,10 '-bis [4-N- (1-cyclohexylethyl) -1, 8-naphthalimide ] -9,9' -spirodicridine
According to the reaction formula
The preparation method comprises the following steps:
a50 mL three-necked flask was charged with (R) -4-bromo-N- (1-cyclohexylethyl) -1, 8-naphthalimide (C1-1, 2.12g,5.5mmol), 10H,10'H-9,9' -spirobiacridine (D3-1, 0.86g,2.5mmol), palladium acetate (23mg,0.1mmol), tri-tert-butylphosphine tetrafluoroborate (58mg, 0.5 mmol)2mmol), sodium tert-butoxide (528mg,5.5mmol) and 15mL of toluene were reacted at 110 ℃ for 24h under Ar. Cooling to room temperature, pouring the mixed solution into water, extracting with dichloromethane, collecting an organic phase, washing with water for several times, and performing chromatography by using a chromatographic column to obtain a crude product, and recrystallizing dichloromethane and n-hexane to obtain 2.23g of the chiral thermal activation delayed fluorescent material 278 as orange powder. MS (EI) M/z 957.1[ M ]+]。
Example 7 chiral thermally activated delayed fluorescence material 295: preparation of (S, S) -10,10 '-bis [4-N- (1-phenylethyl) -1, 8-naphthalimide ] -9,9' -silaspiroacridine
According to the reaction formula
The preparation method comprises the following steps:
a50 mL three-necked flask was charged with (S) -4-bromo-N- (1-phenylethyl) -1, 8-naphthalimide (C2-2, 2.12g,5.5mmol), 10H,10'H-9,9' -silaspirobiacridine (D3-2, 0.91g,2.5mmol), palladium acetate (23mg,0.1mmol), tri-tert-butylphosphine tetrafluoroborate (58mg,0.2mmol), sodium tert-butoxide (528mg,5.5mmol), and 15mL of toluene, and reacted at 110 ℃ for 24 hours under Ar atmosphere. And cooling to room temperature, pouring the mixed solution into water, extracting by using dichloromethane, collecting an organic phase, washing for a plurality of times, and carrying out chromatography by using chromatographic column to obtain a crude product, and recrystallizing by using dichloromethane and normal hexane to obtain 2.20g of the chiral thermal activation delayed fluorescent material 295 as orange powder. MS (EI) M/z 961.5[ M ]+]。
Example 8 chiral thermally activated delayed fluorescence material 296: preparation of (R, R) -10,10 '-bis [4-N- (1-phenylethyl) -1, 8-naphthalimide ] -9,9' -silaspiroacridine
According to the reaction formula
The preparation method comprises the following steps:
a50 mL three-necked flask was charged with (R) -4-bromo-N- (1-phenylethyl) -1, 8-naphthalimide (C1-2, 2.12g,5.5mmol), 10H,10'H-9,9' -silaspirobiacridine (D3-2, 0.91g,2.5mmol), palladium acetate (23mg,0.1mmol), tri-tert-butylphosphine tetrafluoroborate (58mg,0.2mmol), sodium tert-butoxide (528mg,5.5mmol), and 15mLToluene was reacted at 110 ℃ for 24 hours under Ar atmosphere. Cooling to room temperature, pouring the mixed solution into water, extracting with dichloromethane, collecting an organic phase, washing with water for several times, and performing chromatography by using a chromatographic column to obtain a crude product, and recrystallizing dichloromethane and n-hexane to obtain 2.10g of chiral thermal activation delayed fluorescent material 296 as orange powder. MS (EI) M/z 961.3[ M ]+]。
Example 9 chiral thermally activated delayed fluorescence material 311: preparation of (S, S) -5, 10-di [4-N- (1-phenylethyl) -1, 8-naphthalimide ] -phenazine
According to the reaction formula
The preparation method comprises the following steps:
a50 mL three-necked flask was charged with (S) -4-bromo-N- (1-phenylethyl) -1, 8-naphthalimide (C2-2, 2.12g,5.5mmol), 5, 10-dihydrophenazine (D3-3, 0.46g,2.5mmol), palladium acetate (23mg,0.1mmol), tri-tert-butylphosphine tetrafluoroborate (58mg,0.2mmol), sodium tert-butoxide (528mg,5.5mmol), and 15mL of toluene, and reacted at 110 ℃ for 24 hours under Ar atmosphere. And cooling to room temperature, pouring the mixed solution into water, extracting with dichloromethane, collecting an organic phase, washing with water for several times, and carrying out chromatography by using a chromatographic column to obtain a crude product, and recrystallizing with dichloromethane and n-hexane to obtain 1.70g of the chiral thermal activation delayed fluorescent material 311 as red powder. MS (EI) M/z 780.6[ M ]+]。
Example 10 chiral thermally activated delayed fluorescence material 312: preparation of (R, R) -5, 10-di [4-N- (1-phenylethyl) -1, 8-naphthalimide ] -phenazine
According to the reaction formula
The preparation method comprises the following steps:
a50 mL three-necked flask was charged with (R) -4-bromo-N- (1-phenylethyl) -1, 8-naphthalimide (C1-2, 2.12g,5.5mmol), 5, 10-dihydrophenazine (D3-3, 0.46g,2.5mmol), palladium acetate (23mg,0.1mmol), tri-tert-butylphosphine tetrafluoroborate (58mg,0.2mmol), sodium tert-butoxide (528mg,5.5mmol), and 15mL of toluene, and reacted at 110 ℃ for 24 hours under Ar atmosphere. Cooling to room temperature, pouring the mixed solution into water, and extracting with dichloromethaneCollecting and collecting an organic phase, washing with water for several times, performing chromatography by a chromatographic column to obtain a crude product, and recrystallizing dichloromethane and n-hexane to obtain the chiral thermally activated delayed fluorescence material 312 which is 1.61g of orange powder. MS (EI) M/z 780.5[ M ]+]。
Example 11 preparation of OLEDs based on different chiral thermally activated delayed fluorescence materials and testing of their Properties
The following embodiments are described in terms of OLED structures: anode/hole injection layer/hole transport/(electron/exciton blocking layer)/light emitting layer/electron transport layer/electron injection layer/cathode OLEDs based on chiral thermally activated delayed fluorescence materials 97, 98, 103, 104, 277, 278, 295, 296, 311, 312 were prepared and tested for their performance, respectively.
The preparation steps are as follows: referring to fig. 1, a glass substrate coated with ITO (indium tin oxide, anode 1) having a thickness of 75nm was ultrasonically washed with isopropyl alcohol and pure water for 5 minutes, respectively, and then cleaned with ultraviolet ozone, and then transferred into a vacuum deposition chamber; injecting hole injection material MoO3Vacuum (about 10 nm) at a thickness of 1nm-7Torr) is thermally deposited on the transparent ITO electrode to form a hole injection layer 2; depositing TAPC with the thickness of 70nm on the hole injection layer 2 in a vacuum manner to form a hole transport layer 3, and depositing mCP with the thickness of 10nm on the hole transport layer 3 in a vacuum manner to form an electron/exciton blocking layer 4; carrying out vacuum deposition on the mPCN doped with the chiral thermal activation delayed fluorescence material with the concentration of 3 wt% and the thickness of 20nm on the electron/exciton blocking layer 4 to form a light emitting layer 5; the electron transport layer 6 was formed using 3TPYMB to a thickness of 70 nm; depositing lithium fluoride with the thickness of 1nm on the electron transport layer 7 to form an electron injection layer 7; depositing aluminum with the thickness of 100nm on the electron injection layer 7 to form a cathode 8; the device was transferred from the deposition chamber into a glove box and then encapsulated with a UV curable epoxy and a glass cover plate containing a moisture absorber. Wherein, the structural formulas of TAPC, mCP, mCPCN and 3TPYMB are respectively as follows:
the OLEDs prepared based on the chiral thermal activation delayed fluorescence materials 97, 98, 103, 104, 277, 278, 295, 296, 311 and 312 are named as OLED-97, OLED-98, OLED-103, OLED-104, OLED-277, OLED-278, OLED-295, OLED-296, OLED-311 and OLED-312 respectively, and the specific structures of the OLEDs are as follows:
OLED-97: ITO (75nm, anode)/MoO3(1nm, hole injection layer)/TAPC (70nm, hole transport layer)/mCP (10nm, (electron/exciton blocking layer))/mCPCN 3 wt% 97(20nm, light emitting layer)/3 TPYMB (70nm, electron transport layer)/LiF (1nm, electron injection layer)/Al (100nm, cathode).
OLED-98: the difference from OLED-97 is that 3 wt% 98 was substituted for 3 wt% 97 to form a light emitting layer with mCPCN.
OLED-103: the difference from OLED-97 is that 3 wt% 103 is substituted for 3 wt% 97 to form the light emitting layer with mCPCN.
An OLED-104: the difference from OLED-97 is that 3 wt% 104 was substituted for 3 wt% 97 to form a light emitting layer with mCPCN.
OLED-277: the difference from OLED-97 is that 3 wt% 277 is substituted for 3 wt% 97 to form a light emitting layer with mCPCN.
OLED-278: the difference from OLED-97 is that 3 wt% 278 instead of 3 wt% 97 forms the light emitting layer with mCPCN.
OLED-295: the difference from OLED-97 is that 3 wt% 97 was replaced with 3 wt% 295 to form a light emitting layer with mCPCN.
OLED-296: the difference from OLED-97 is that 3 wt% 296 was substituted for 3 wt% 97 to form a light emitting layer with mCPCN.
OLED-311: the difference from OLED-97 is that 3 wt% 97 is replaced with 3 wt% 311 to form a light emitting layer with mCPCN.
An OLED-312: the difference from OLED-97 is that 3 wt% 312 instead of 3 wt% 97 forms the light emitting layer with mCPCN.
The luminous efficiency, External Quantum Efficiency (EQE) of the OLED device was determined by a Keithley source measurement system (Keithley 2400source meter, Keithley 2000Currentmeter) with calibrated silicon photodiodes, the electroluminescence spectra were measured by SPEX CCD3000 spectrometer, JY, france, the circularly polarized light asymmetry factor (g) of the OLEDEL) Is a system measurement which is strictly set up according to the literature standard (ACS Nano,2017,11, 12713), and all the measurements are carried out in a roomThe reaction is completed in warm atmosphere. Luminous efficiency, External Quantum Efficiency (EQE), circularly polarized light asymmetry factor (g) of each OLED deviceEL) The measurement results are shown in table 1; as can be seen from Table 1, the chiral thermally activated delayed fluorescence materials prepared in examples 1-10 can be used as materials of light emitting layers in OLEDs, and can improve the light emitting efficiency of the OLED by matching with proper host materials, and meanwhile, 10 can be obtained-1The asymmetric factor of the level circular polarization luminescence provides a solution for a luminescent device with low manufacturing cost and high efficiency, and can be widely applied to the field of organic electroluminescence. In addition, comparing the circularly polarized light asymmetry factors of OLED-103 and OLED-104 as shown in FIG. 2, it can be seen that OLED-103 and OLED-104 obtain circularly polarized light with very high asymmetry factor.
TABLE 1
| Device with a metal layer | Color coordinates CIE | Luminous efficiency (lm/W) | EQE(％) | gEL |
| OLED-97 | x＝0.52,y＝0.43 | 45.7 | 22.3 | 0.05 |
| OLED-98 | x＝0.52,y＝0.43 | 45.5 | 22.1 | -0.04 |
| OLED-103 | x＝0.59,y＝0.40 | 43.2 | 18.5 | 0.30 |
| OLED-104 | x＝0.59,y＝0.40 | 43.5 | 19.0 | -0.38 |
| OLED-277 | x＝0.57,y＝0.41 | 45.5 | 26.4 | 0.03 |
| OLED-278 | x＝0.57,y＝0.41 | 46.0 | 26.0 | -0.04 |
| OLED-295 | x＝0.55,y＝0.40 | 43.3 | 25.8 | 0.23 |
| OLED-296 | x＝0.55,y＝0.40 | 43.0 | 25.5 | -0.28 |
| OLED-311 | x＝0.57,y＝0.43 | 42.0 | 20.1 | 0.15 |
| OLED-312 | x＝0.57,y＝0.43 | 42.3 | 20.5 | -0.17 |
In summary, the invention provides a chiral thermally activated delayed fluorescence material, and a preparation method and an application thereof, wherein the chiral organic compound with the structure, which takes 1, 8-naphthalimide as a parent nucleus, has good Thermally Activated Delayed Fluorescence (TADF) characteristics and a high asymmetric excess value, and is beneficial to obtaining circularly polarized light with a high asymmetric factor, and when the chiral organic compound is used in a light emitting layer of an OLED, the chiral organic compound can obtain high device light emitting efficiency. In addition, the preparation method of the chiral thermal activation delayed fluorescence material is simple, raw materials are easy to obtain, and a simple and effective solution is provided for obtaining a circular polarization light-emitting device with low manufacturing cost, high efficiency and large asymmetric factor.
It is to be understood that the invention is not limited to the examples described above, but that modifications and variations may be effected thereto by those of ordinary skill in the art in light of the foregoing description, and that all such modifications and variations are intended to be within the scope of the invention as defined by the appended claims.
Claims (10)
1. A chiral thermally activated delayed fluorescence material, wherein the chiral thermally activated delayed fluorescence material is characterized in thatThe general structural formula of the fluorescent material is
In the formulas I to IV, R is chiral alkyl or chiral aralkyl, and R' are independently selected from aryl or heteroaryl with electron donating effect.
2. The chiral thermally activated delayed fluorescence material of claim 1, wherein R is selected from the group consisting of
R1Is selected from C2～C20Alkyl of (C)3～C10Cycloalkyl of, C5～C20Arylmethylene or C of5～C20Substituted arylmethylene of (a);
Ar1selected from phenyl, naphthyl, thienyl, furyl, pyridyl, C1～C6Alkyl of (C)2～C6Alkenyl of, C2～C6Alkynyl of (A), C1～C6At least one substituted phenyl, naphthyl, thienyl, furyl or pyridyl group.
3. The chiral thermally activated delayed fluorescence material of claim 2, wherein C is5～C20The arylmethylene of (a) is selected from the group consisting of phenylmethylene, naphthylmethylene, thienylmethylene, furanylmethylene, or pyridylmethylene;
said C is5～C20The substituted arylmethylene group is selected from C1～C6Alkyl of (C)2～C6Alkenyl of, C2～C6Alkynyl of (A), C1～C6At least one substituted phenylmethylene or naphthylmethylene of alkoxy and diphenylaminoA phenyl group, a thienylmethylene group, a furanylmethylene group, a pyridylmethylene group.
4. The chiral thermally activated delayed fluorescence material of claim 1, wherein R' is selected from the group consisting of
R2Selected from hydrogen, C1～C4Alkyl of (C)3～C6Cycloalkyl of, C4～C20Aryl or C of4～C20Substituted aryl of (a);
Ar2selected from phenyl, naphthyl, thienyl, furyl, pyridyl, C1～C4Alkyl of (C)2～C6Alkenyl of, C2～C6Alkynyl of (A), C1～C6At least one substituted phenyl, naphthyl, thienyl, furyl or pyridyl group.
5. The chiral thermally activated delayed fluorescence material of claim 4, wherein C is4～C20Aryl of (a) is selected from phenyl, naphthyl, thienyl, furyl or pyridyl;
said C is4～C20Is selected from C1～C4Alkyl of (C)2～C6Alkenyl of, C2～C6Alkynyl of (A), C1～C6At least one substituted phenyl, naphthyl, thienyl, furyl or pyridyl group.
6. The chiral thermally activated delayed fluorescence material of claim 1, wherein R "is selected from the group consisting of
7. The chiral thermally activated delayed fluorescence material of claim 1, wherein the chiral thermally activated delayed fluorescence material is
8. A method for preparing the chiral thermally activated delayed fluorescence material of any claim 1 to 7, wherein the method is based on the reaction formula
The method comprises the following steps:
E. carrying out amidation reaction on chiral primary amine A and halogenated 1, 8-naphthalic anhydride B in a first solvent under an inert atmosphere, and after the reaction is finished, carrying out purification treatment to obtain chiral halogenated 1, 8-naphthalimide C;
wherein, the chiral primary amine A is
R is chiral alkyl or chiral aralkyl; halogenated 1, 8-naphthalic anhydrides B are
X ═ Br or I; chiral halogenated 1, 8-naphthalimides C is
F. Under the inert atmosphere, carrying out coupling reaction on chiral halogenated 1, 8-naphthalimide C and a compound D containing R 'or R' in a second solvent under the action of a palladium catalyst, an organophosphorus ligand and an alkaline substance, and after the reaction is finished, carrying out purification treatment to obtain the chiral thermally activated delayed fluorescent material;
wherein the compound D containing R 'or R' is
R 'and R' are independently selected from aryl or heteroaryl groups having an electron donating effect.
9. The method for preparing the chiral thermally activated delayed fluorescence material according to claim 8, wherein in the step E, the temperature of the amidation reaction is 110 to 150 ℃, and the time of the amidation reaction is 12 to 48 hours;
in the step F, the temperature of the coupling reaction is 80-150 ℃, and the time of the coupling reaction is 12-48 h.
10. An organic light emitting diode comprising an anode, a cathode, and a light emitting layer disposed between the anode and the cathode, wherein the material of the light emitting layer comprises the chiral thermally activated delayed fluorescence material as claimed in any one of claims 1 to 7.
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