CN117946109A - Purine derivative and electroluminescent device - Google Patents
Purine derivative and electroluminescent device Download PDFInfo
- Publication number
- CN117946109A CN117946109A CN202410103227.2A CN202410103227A CN117946109A CN 117946109 A CN117946109 A CN 117946109A CN 202410103227 A CN202410103227 A CN 202410103227A CN 117946109 A CN117946109 A CN 117946109A
- Authority
- CN
- China
- Prior art keywords
- layer
- electrode
- purine derivative
- luminescent
- electroluminescent device
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title claims abstract description 10
- 239000000463 material Substances 0.000 claims abstract description 89
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 239000010410 layer Substances 0.000 claims description 95
- 150000001875 compounds Chemical class 0.000 claims description 35
- 230000005525 hole transport Effects 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 239000012044 organic layer Substances 0.000 claims description 12
- 230000005540 biological transmission Effects 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 5
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical group [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 238000004544 sputter deposition Methods 0.000 claims description 5
- 229910001148 Al-Li alloy Inorganic materials 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 4
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 claims description 4
- 229910045601 alloy Inorganic materials 0.000 claims description 4
- 239000000956 alloy Substances 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 238000000151 deposition Methods 0.000 claims description 4
- -1 dibenzofuranyl Chemical group 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052709 silver Inorganic materials 0.000 claims description 4
- 239000004332 silver Substances 0.000 claims description 4
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 claims description 4
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 230000008021 deposition Effects 0.000 claims description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 239000011787 zinc oxide Substances 0.000 claims description 3
- 238000013329 compounding Methods 0.000 claims description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 54
- 150000003212 purines Chemical class 0.000 abstract description 17
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 abstract description 16
- 238000009826 distribution Methods 0.000 abstract description 4
- 238000006467 substitution reaction Methods 0.000 abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 3
- 230000001105 regulatory effect Effects 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 36
- 238000003786 synthesis reaction Methods 0.000 description 36
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 23
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 18
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 18
- 239000012043 crude product Substances 0.000 description 17
- 239000007787 solid Substances 0.000 description 14
- 239000011799 hole material Substances 0.000 description 12
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000001035 drying Methods 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- SXZIXHOMFPUIRK-UHFFFAOYSA-N diphenylmethanimine Chemical compound C=1C=CC=CC=1C(=N)C1=CC=CC=C1 SXZIXHOMFPUIRK-UHFFFAOYSA-N 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 238000007670 refining Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000002346 layers by function Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000005284 excitation Effects 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 3
- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 3
- 229940126639 Compound 33 Drugs 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 3
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- XHCAGOVGSDHHNP-UHFFFAOYSA-N 1-bromo-4-tert-butylbenzene Chemical compound CC(C)(C)C1=CC=C(Br)C=C1 XHCAGOVGSDHHNP-UHFFFAOYSA-N 0.000 description 1
- RMFWVOLULURGJI-UHFFFAOYSA-N 2,6-dichloro-7h-purine Chemical compound ClC1=NC(Cl)=C2NC=NC2=N1 RMFWVOLULURGJI-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- DRLMMVPCYXFPEP-UHFFFAOYSA-N 2-bromo-1,3-benzothiazole Chemical compound C1=CC=C2SC(Br)=NC2=C1 DRLMMVPCYXFPEP-UHFFFAOYSA-N 0.000 description 1
- ZMSUVHHASUJZNH-UHFFFAOYSA-N 2-bromo-1,3-benzoxazole Chemical compound C1=CC=C2OC(Br)=NC2=C1 ZMSUVHHASUJZNH-UHFFFAOYSA-N 0.000 description 1
- RNEOFIVNTNLSEH-UHFFFAOYSA-N 2-bromo-1-benzofuran Chemical compound C1=CC=C2OC(Br)=CC2=C1 RNEOFIVNTNLSEH-UHFFFAOYSA-N 0.000 description 1
- IJICRIUYZZESMW-UHFFFAOYSA-N 2-bromodibenzothiophene Chemical compound C1=CC=C2C3=CC(Br)=CC=C3SC2=C1 IJICRIUYZZESMW-UHFFFAOYSA-N 0.000 description 1
- WGFCNCNTGOFBBF-UHFFFAOYSA-N 2-bromopyrazine Chemical compound BrC1=CN=CC=N1 WGFCNCNTGOFBBF-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- IXJSDKIJPVSPKF-UHFFFAOYSA-N 4-bromo-1-methylpyrazole Chemical compound CN1C=C(Br)C=N1 IXJSDKIJPVSPKF-UHFFFAOYSA-N 0.000 description 1
- CHODTZCXWXCALP-UHFFFAOYSA-N 5-bromoquinoline Chemical compound C1=CC=C2C(Br)=CC=CC2=N1 CHODTZCXWXCALP-UHFFFAOYSA-N 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 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
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000012858 packaging process Methods 0.000 description 1
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses a purine derivative and an electroluminescent device, which utilize an aromatic configuration of a main framework of a purine molecule containing a plurality of nitrogen atoms as an inner core, wherein charges of the purine molecule are distributed asymmetrically between two rings, and then electron distribution of the purine molecule is regulated by carrying out a specific group substitution process on 2, 6 and 9 positions of the purine molecule, so that the purine derivative can be used as an efficient electron transport material for an electron transport layer, and can be used as a main luminescent material with excellent performance for a luminescent layer.
Description
Technical Field
The invention belongs to the technical field of organic luminescent materials, and particularly relates to a purine derivative and an electroluminescent device.
Background
New materials have been one of the heavy tasks of researchers in this field as an important driving force for the development of technological innovations. The current mature OLED device is realized by adopting a multi-layer functional composite mode, and the functional layers mainly comprise a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer, an electron transport layer, an electron blocking layer and a light emitting layer. The main purpose of adding each functional layer is to balance the holes and electrons injected from the anode and cathode, thereby facilitating the recombination of the holes and electrons in the light-emitting layer, improving the exciton utilization rate of the device, and finally improving the light-emitting efficiency and the service life of the device.
However, in the organic electroluminescent device, the electron transport rate in the carrier is lower than the hole transport rate, and the two transport rates are approximately different by an order of magnitude, which makes the number of electrons and holes in the light emitting layer unbalanced, resulting in quenching of luminescence, and affecting the device performance. And the conventional triarylamine hole transport materials are easy to obtain and have wide material development, so that the electron transport materials are obviously rare compared with the hole transport materials.
Therefore, how to develop a light-emitting layer material and an electron-transporting layer material with high light-emitting efficiency and high electron-transporting performance, to improve the electron-transporting rate and further promote the injection balance of positive and negative carriers, so as to improve the light-emitting efficiency of the device and prolong the service life of the whole device is a problem to be solved by those skilled in the art.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a purine derivative and an electroluminescent device, wherein the purine derivative can be used as a main luminescent material and an electron transport material of the electroluminescent device.
In order to solve the technical problems, the technical scheme of the invention is as follows: a purine derivative having the structural formula of formula 1:
Wherein R 1、R2 is independently selected from hydrogen, deuterium, fluorine, cyano, and alkyl or aryl substituted or unsubstituted between C 1～C10 carbon atoms; r 3、R4 is independently selected from C 2～C25 substituted or unsubstituted alkyl, cycloalkyl, phenyl, naphthyl, phenanthryl, biphenyl, pyridyl, quinolinyl, pyrrolyl, benzofuranyl or benzothienyl; r 5 is selected from substituted or unsubstituted heteroaryl.
Preferably, the heteroaryl group comprises pyridyl, pyrazinyl, dibenzothienyl, dibenzofuranyl, benzothiazolyl, benzoxazolyl, pyrazolyl.
Preferably, the general formula 1 includes chemical formulas 1 to 7, and the specific structural formula is:
Wherein R 1、R2 is independently selected from hydrogen, deuterium, fluorine, cyano, and alkyl or aryl substituted or unsubstituted between C 1～C10 carbon atoms; r 3、R4 is independently selected from C 2～C25 substituted or unsubstituted alkyl, cycloalkyl, phenyl, naphthyl, phenanthryl, biphenyl, pyridyl, quinolinyl, pyrrolyl, benzofuranyl or benzothienyl.
Preferably, an electroluminescent device comprising a first electrode, a second electrode and an organic layer between the first electrode and the second electrode, characterized in that any one or a combination of at least two of compounds 1 to 112 comprising a purine derivative is contained in the organic layer.
Preferably, the organic layer includes a hole transport layer, a light emitting layer and an electron transport layer, the first electrode and the second electrode are a cathode and an anode, respectively, the hole transport layer is located between the anode and the light emitting layer, the electron transport layer is located between the cathode and the light emitting layer, and the main luminescent material of the light emitting layer is selected from any one or a combination of at least two of the compounds 1 to 112; the material of the electron transport layer is also selected from, but not limited to, any one or a combination of more of the compounds 1 to 112.
Preferably, the first electrode is formed by sputtering or deposition on a substrate, and when the first electrode is used as an anode, it is selected from indium tin oxide, indium zinc oxide, tin dioxide, zinc oxide, or any combination thereof; when the first electrode is used as a cathode, it is selected from the group consisting of magnesium, silver, aluminum-lithium, calcium, magnesium-indium, magnesium-silver metal or alloy, and any combination thereof.
Preferably, the light emitting layer is made of a composite of a host light emitting material and a guest light emitting material; the guest luminescent material is selected fromAnd the mass ratio of the host luminescent material to the guest luminescent material is 95:5.
Preferably, the hole transport layer is made of one or any combination of HT-1, HT-2 and HT-3, and has the following structural formula:
Compared with the prior art, the invention has the advantages that:
(1) According to the invention, an aromatic structure of a main framework of a purine molecule containing a plurality of nitrogen atoms is used as an inner core, charges of the main framework are asymmetrically distributed between two rings, and then electron distribution of the main framework is regulated by carrying out a specific group substitution process on 2,6 and 9 positions of the main framework, so that the main framework can be used as an efficient electron transport material and applied to an electron transport layer, and can be used as a main luminescent material with excellent performance and applied to a luminescent layer;
(2) According to the invention, purine is taken as a fixed inner core, carbazole is taken as a fixed substituent, and when the molecules are taken as a main luminescent material, the molecules have higher triplet excitation state energy, and the triplet excitation state energy can be effectively utilized in practical application, so that the luminescent power of a device is greatly improved;
(3) The purine derivative provided by the invention is used as a main luminescent material and an electron transport material, so that the three-dimensional stability is better, and a glassy film formed by the material is more stable, so that the maximum contact with the stability of a cathode material is realized, and the reliable and stable transport of electrons is ensured;
(4) The purine derivative disclosed by the invention realizes the integration of luminescence and electron transmission of a device main body, can realize effective simplification of a device structure and reduces the cost.
Drawings
FIG. 1 is a schematic diagram of an electroluminescent device according to the present invention;
FIG. 2, nuclear magnetic resonance spectrum of compound 1 of the present invention;
FIG. 3, nuclear magnetic resonance spectrum of compound 19 of the present invention;
FIG. 4, nuclear magnetic resonance spectrum of compound 33 of the present invention;
FIG. 5, nuclear magnetic resonance spectrum of compound 58 of the present invention;
FIG. 6, nuclear magnetic resonance spectrum of compound 76 of the present invention;
FIG. 7, nuclear magnetic resonance spectrum of compound 95 of the present invention;
FIG. 8, nuclear magnetic resonance spectrum of the compound 105 of the present invention.
Reference numerals illustrate:
1. The light-emitting device comprises a transparent substrate, 2, an anode, 3, a hole injection layer, 4, a hole transport layer, 5, a light-emitting layer, 6, an electron transport layer, 7, an electron injection layer, 8 and a cathode.
Detailed Description
Embodiments of the present invention are described below in conjunction with the examples, and the starting materials and reagents described herein are all commercially available.
A purine derivative having the structural formula of formula 1:
Wherein R 1、R2 is independently selected from hydrogen, deuterium, fluorine, cyano, and alkyl or aryl substituted or unsubstituted between C 1～C10 carbon atoms; r 3、R4 is independently selected from C 2～C25 substituted or unsubstituted alkyl, cycloalkyl, phenyl, naphthyl, phenanthryl, biphenyl, pyridyl, quinolinyl, pyrrolyl, benzofuranyl or benzothienyl; r 5 is selected from substituted or unsubstituted heteroaryl.
Preferably, the heteroaryl group comprises pyridyl, pyrazinyl, dibenzothienyl, dibenzofuranyl, benzothiazolyl, benzoxazolyl, pyrazolyl.
Preferably, the general formula 1 includes chemical formulas 1 to 7, and the specific structural formula is:
Wherein R 1、R2 is independently selected from hydrogen, deuterium, fluorine, cyano, and alkyl or aryl substituted or unsubstituted between C 1～C10 carbon atoms; r 3、R4 is independently selected from C 2～C25 substituted or unsubstituted alkyl, cycloalkyl, phenyl, naphthyl, phenanthryl, biphenyl, pyridyl, quinolinyl, pyrrolyl, benzofuranyl or benzothienyl.
Preferably, the general formula 1 comprises compounds 1 to 112, and the specific structural formula is as follows:
Preferably, an electroluminescent device comprising a first electrode, a second electrode and an organic layer between the first electrode and the second electrode, characterized in that any one or a combination of at least two of compounds 1 to 112 comprising a purine derivative is contained in the organic layer.
Preferably, the organic layer includes a hole transport layer, a light emitting layer and an electron transport layer, the first electrode and the second electrode are a cathode and an anode, respectively, the hole transport layer is located between the anode and the light emitting layer, the electron transport layer is located between the cathode and the light emitting layer, and the main luminescent material of the light emitting layer is selected from any one or a combination of at least two of the compounds 1 to 112; the material of the electron transport layer is also selected from, but not limited to, any one or a combination of more of the compounds 1 to 112.
Preferably, the first electrode is formed by sputtering or deposition on a substrate, and when the first electrode is used as an anode, it is selected from indium tin oxide, indium zinc oxide, tin dioxide, zinc oxide, or any combination thereof; when the first electrode is used as a cathode, it is selected from the group consisting of magnesium, silver, aluminum-lithium, calcium, magnesium-indium, magnesium-silver metal or alloy, and any combination thereof.
Preferably, the light emitting layer is made of a composite of a host light emitting material and a guest light emitting material; the guest luminescent material is selected fromAnd the mass ratio of the host luminescent material to the guest luminescent material is 95:5.
Preferably, the hole transport layer is made of one or any combination of HT-1, HT-2 and HT-3, and has the following structural formula:
the synthesis process of the compounds 1 to 112 is introduced as follows:
key intermediate M1 synthesis step:
The first step:
l3 ligand used in the course of the reaction:
The operation process comprises the following steps: 188g (1.0 mol) of 2, 6-dichloropurine, 166g (1.05 mol) of 2-bromopyridine, 7.2g of cuprous bromide, 30g of L3 ligand, 20g of sodium ascorbate (NaAsc), 0.06g of potassium hydroxide and 1.0L of solvent (DMF: H2O=4:1) are sequentially added into a 2L three-port bottle, the reaction is heated to 120 ℃ and stirred for 20-48H until the reaction is completed. Cooling the reaction solution to room temperature, adding water and ethyl acetate for extraction, drying an organic phase, concentrating, recrystallizing with ethanol, and drying to obtain white solid M1-1, weight 213g, HPLC content 97%, yield 80%, LC-MS:264.98.
And a second step of:
The operation process comprises the following steps: into a 2L three-necked flask, M1-1133g, carbazole 84g, xylene 1.0L, sodium tert-butoxide 96g, pd 2(dba)3 9.2.2 g and Amphos5.3g were added, and the temperature was raised to 120-125℃under an inert atmosphere to complete the reaction for 6-8 hours. The reaction solution is washed with water, dried, concentrated under reduced pressure to obtain crude product, and the crude product is refined by a silica gel column to obtain 151g of white solid with HPLC content of 98%, yield of 76% and LC-MS:396.11.
And a third step of:
The operation process comprises the following steps: under the protection of argon, M1-279g (0.2 mol), benzophenone imine 40g (0.22 mol), toluene 500mL, sodium tert-butoxide 38g (0.4 mol) and Pd 2(dba)3 0.92.92 g (1 mmol) after gas replacement are added into a 1000mL three-necked flask, DPE-phos1.1g (2 mmol) are heated to reflux reaction for 4-5 h until the reaction is complete. Then naturally cooling to room temperature, adding 250mL of water, washing and separating liquid, washing an organic phase with water to be neutral, adding 30mL of concentrated hydrochloric acid, heating to 60-70 ℃, fully stirring and hydrolyzing for 5h until a large amount of solids are separated out from the system, cooling to room temperature, filtering and drying; and (3) collecting the solid, adding the solid into a reaction bottle again, adding 750mL of NaOH solution (1 mol/L), heating to 70-80 ℃, stirring to fully free for 10-12 hours, cooling to room temperature, filtering, and draining to collect a solid crude product. The crude solid product is further boiled, washed and purified by a mixed solvent of toluene and ethanol to obtain an off-white solid M1, 60g of which the HPLC content is 99 percent and the yield is 80 percent; LC-MS molecular weight 377.10.
Key intermediate M2 synthesis step:
The first step:
the operation process comprises the following steps: with reference to the synthesis process of M1-1, 167g of 2-bromopyrazine is added in total to yield M2-1208g, and the yield is 78% and LC-MS:266.12.
And a second step of:
the operation process comprises the following steps: 79g of carbazole is added in total according to the M1-2 synthesis process, and M2-2151g is produced with a yield of 76% and LC-MS:397.85.
And a third step of:
the operation process comprises the following steps: referring to the M1 synthesis procedure, a total of 40g of benzophenone imine was added to yield M259g, yield 78%, LC-MS molecular weight 378.06.
Key intermediate M3 synthesis step:
The first step:
the operation process comprises the following steps: with reference to the synthesis process of M1-1, 276g of 2-bromodibenzothiophene is added in total to yield M3-1267g, and the yield is 72 percent, LC-MS:371.30.
And a second step of:
the operation process comprises the following steps: 79g of carbazole is added in total according to the synthesis process of M1-2, and M3-2188g is produced, the yield is 75%, and LC-MS is 501.21.
And a third step of:
The operation process comprises the following steps: referring to the M1 synthesis process, 40g of benzophenone imine was added together to yield M371g, yield 74%, LC-MS molecular weight 482.04.
Key intermediate M4 synthesis step:
The first step:
The operation process comprises the following steps: 259g of dibenzofuran is added in total according to the synthesis process of M1-1, so that M4-1256g is produced, and the yield is 72 percent, and LC-MS is 355.19.
And a second step of:
The operation process comprises the following steps: 79g of carbazole is added in total according to the M1-2 synthesis process, and M4-2177g is produced, the yield is 73%, and LC-MS is 485.20.
And a third step of:
the operation process comprises the following steps: referring to the M1 synthesis process, a total of 40g of benzophenone imine was added to yield M471g, yield 76% and LC-MS molecular weight 466.06.
Key intermediate M5 synthesis step:
The first step:
the operation process comprises the following steps: referring to the synthesis process of M1-1, 225g of 2-bromobenzothiazole is added together to yield M5-1222g with the yield of 69 percent and LC-MS:322.19.
And a second step of:
The operation process comprises the following steps: 79g of carbazole is added in total according to the synthesis process of M1-2, and M5-2159g is produced with the yield of 70 percent, and LC-MS is 452.95.
And a third step of:
The operation process comprises the following steps: referring to the M1 synthesis process, 40g of benzophenone imine was added together to yield M562g, the yield was 72%, and the LC-MS molecular weight was 433.04.
Key intermediate M6 synthesis step:
The first step:
The operation process comprises the following steps: referring to the synthesis process of M1-1, 2-bromobenzoxazole 208 is added together to yield M6-1214g, the yield is 71%, and LC-MS is 304.97.
And a second step of:
The operation process comprises the following steps: 79g of carbazole is added in total according to the synthesis process of M1-2, and M6-2 162g is produced, the yield is 74%, and LC-MS is 436.05.
And a third step of:
The operation process comprises the following steps: with reference to the M1 synthesis process, 40g of benzophenone imine is added in total to yield 660g of M, and the yield is 72%; LC-MS molecular weight 417.03.
Key intermediate M7 synthesis step:
The first step:
The operation process comprises the following steps: 169g of N-methyl-4-bromopyrazole are added together according to the synthesis process of M1-1, so that M7-1202g is produced, the yield is 75%, and LC-MS is 254.01.
And a second step of:
the operation process comprises the following steps: 79g of carbazole is added in total by referring to the synthesis process of M1-2, and M7-2148g is produced, and the yield is 74% and LC-MS is 399.12.
And a third step of:
The operation process comprises the following steps: referring to the synthesis process of M1, adding 40g of benzophenone imine to obtain M761g, and obtaining 80% of yield; LC-MS molecular weight 380.03.
The synthesis implementation process of the preferred compounds of the chemical formula 1, chemical formula 2, chemical formula 3, chemical formula 4, chemical formula 5, chemical formula 6 and chemical formula 7 is exemplified as follows:
Application example one
Synthesis of Compound 1:
The operation process comprises the following steps: in a 100mL three-necked flask, 13.8g of M, 3.5g of bromobenzene, 50mL of xylene, 3.4g of sodium tert-butoxide, 0.18g of Pd 2(dba)3 and 0.11g of Amphos were placed, and the temperature was raised to 120-125℃under an inert atmosphere to complete the reaction for 6-8 hours. Washing the reaction solution with water, drying, concentrating under reduced pressure to obtain a crude product, refining the crude product by a silica gel column to obtain 4.2g of white solid, wherein the HPLC content is 99%, and the yield is 79%; LC-MS molecular weight 529.13.
Application example II
Synthesis of Compound 19:
The operation process comprises the following steps: in a 100mL three-necked flask, M23.8g, 5.1g of 4-bromobiphenyl, 50mL of xylene, 3.4g of sodium tert-butoxide, 0.18g of Pd 2(dba)3 and 0.11g of Amphos were placed, and the temperature was raised to 120-125℃under an inert atmosphere to complete the reaction for 6-8 hours. Washing the reaction solution with water, drying, concentrating under reduced pressure to obtain crude product, refining the crude product by a silica gel column to obtain white solid with the content of 99% by HPLC and the yield of 75%; LC-MS molecular weight 681.23.
Application example III
Synthesis of Compound 33:
The operation process comprises the following steps: into a 100mL three-necked flask, 34.8g of M, 4.7g of 4-tert-butylbromobenzene, 50mL of xylene, 3.4g of sodium tert-butoxide, 0.18g of Pd 2(dba)3 and 0.11g of Amphos were placed, and the temperature was raised to 120-125 ℃ under an inert atmosphere to react for 6-8 hours until the reaction was completed. Washing the reaction solution with water, drying, concentrating under reduced pressure to obtain a crude product, refining the crude product by a silica gel column to obtain 5.7g of white solid with 99% of HPLC content and 76% of yield; LC-MS molecular weight 746.25.
Application example IV
Synthesis of Compound 58:
The operation process comprises the following steps: into a 100mL three-necked flask, 44.7g of M, 4.3g of 2-bromobenzofuran, 50mL of xylene, 3.4g of sodium tert-butoxide, 0.18g of Pd 2(dba)3 and 0.11g of Amphos were placed, and the temperature was raised to 120-125 ℃ under an inert atmosphere to react for 6-8 hours until the reaction was completed. Washing the reaction solution with water, drying, concentrating under reduced pressure to obtain a crude product, refining the crude product by a silica gel column to obtain 5.0g of white solid with 99% of HPLC content and 72% of yield; LC-MS molecular weight 698.02.
Application example five
Synthesis of Compound 76:
The operation process comprises the following steps: in a 100mL three-necked flask, 54.3g of M, 4.6g of 5-bromoquinoline, 50mL of xylene, 3.4g of sodium tert-butoxide, 0.18g of Pd 2(dba)3 and 0.11g of Amphos were placed, and the temperature was raised to 120-125℃under an inert atmosphere to complete the reaction for 6-8 hours. Washing the reaction solution with water, drying, concentrating under reduced pressure to obtain crude product, refining the crude product by a silica gel column to obtain white solid 4.8g, wherein the HPLC content is 99%, and the yield is 70%; LC-MS molecular weight 687.01.
Application example six
Synthesis of Compound 95:
The operation process comprises the following steps: into a 100mL three-necked flask, M64.2g, bromocyclohexane 4.6g, xylene 50mL, sodium tert-butoxide 3.4g and Pd 2(dba)3 0.18g,Amphos 0.11g were added, and the temperature was raised to 120-125℃under an inert atmosphere to complete the reaction for 6-8 hours. Washing the reaction solution with water, drying, concentrating under reduced pressure to obtain crude product, refining the crude product by a silica gel column to obtain white solid 4.1g, wherein the HPLC content is 99%, and the yield is 70%; LC-MS molecular weight 581.01.
Application example seven
Synthesis of compound 105:
The operation process comprises the following steps: into a 100mL three-necked flask, 73.8g of M3-bromopyridine, 3.5g of xylene, 50mL of sodium tert-butoxide, 3.4g of Pd 2(dba)3 0.18g,Amphos 0.11g and the temperature of 120-125 ℃ were increased under an inert atmosphere to react for 6-8 h until the reaction was completed. Washing the reaction solution with water, drying, concentrating under reduced pressure to obtain a crude product, refining the crude product by a silica gel column to obtain 3.6g of white solid, wherein the HPLC content is 99%, and the yield is 68%; LC-MS molecular weight 534.04.
Other compound synthesis methods are similar, and all refer to the completion of compound 1 synthesis, and key intermediates used in the synthesis of compounds 1-112 are arranged in the following table 1.
TABLE 1
/>
( Remarks: the 16 intermediates in the first column are intermediates for preparing the compounds 1 to 16 respectively, and the other columns are the same, and M1 to M7 react with the intermediates in the corresponding columns respectively to sequentially generate the compounds with the numbers 1 to 112. )
The nuclear magnetic patterns of compound 1, compound 19, compound 33, compound 58, compound 76, compound 95 and compound 105 are shown in FIGS. 2 to 8.
The preferred compounds based on the above compounds 1-112 are used as a main body luminescent material and a transmission material in a test device sample, wherein the basic structure and the preparation method of the device adopt the currently industry-accepted device preparation process technology, the schematic diagram of the device is shown in fig. 1, and the specific description of the device is as follows:
Experimental procedure the test device comprised five major parts, an anode (ITO conductive glass), a Hole Transport Layer (HTL), an emissive layer (EML), an Electron Transport Layer (ETL) and a cathode. Wherein one or more of the above preferred compounds are used in the EML, ETL regions for use as host luminescent materials, electron transport materials for evaluation of experimental procedures, the specific device preparation is briefly described as follows:
Preferably, a substrate can be used below the first electrode or above the second electrode, and the substrate is made of glass or polymer material with excellent mechanical strength, thermal stability, waterproofness and transparency, and ITO conductive glass is adopted in the test process. The substrate for a display may have a Thin Film Transistor (TFT) array and a specific display image formed by combining the arrays.
Preferably, the organic layer includes a hole transport layer, a light emitting layer, and an electron transport layer, the first electrode and the second electrode are an anode and a cathode, respectively, the hole transport layer is located between the anode and the light emitting layer, and the electron transport layer is located between the cathode and the light emitting layer. The host luminescent material of the luminescent layer adopts any one or a combination of a plurality of compounds 1-112 of the invention, and the guest material is matched with the common excellent guest material accepted by industry; the electron transport layer material also employs a combination of any one or more of the compounds 1 to 112 of the present invention.
In particular, the first electrode may be formed by sputtering or depositing a material serving as the first electrode on the substrate. As the first electrode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), zinc oxide (ZnO), or any combination thereof may be selected. The second electrode may be realized by using a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (mg—ag), or an organic combination thereof as the cathode.
The functional organic layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, etc., and the compound used as the organic layer may be small organic molecules, large organic molecules and polymers, and combinations thereof.
The hole transport layer may be a single layer structure Hole Transport Layer (HTL), including a single layer hole transport layer containing only one compound which functions both as hole injection and hole transport, and a composite hole transport layer containing a plurality of compounds. The composite hole transport layer is mainly an organic hole material combination mode of an industry common arrangement mode which comprises a Hole Injection Layer (HIL), a Hole Transport Layer (HTL) and an Electron Blocking Layer (EBL) in sequence. The light-emitting layer is positioned between the hole transport layer and the electron transport layer, the host light-emitting material is realized by selecting one or more combinations of the compounds 1-112, preferably the compounds, the matched guest light-emitting material adopts the guest light-emitting material mature in industry to carry out the matching test, and the host light-emitting material and the guest material are prepared according to the following ratio of 95:5, compounding the components. The electron transport layer material may also be realized with one or more combinations of the compounds 1 to 112, preferably compounds. After the preparation of the functional layer for realizing organic luminescence is finished, evaporating a hole blocking material on the luminescent layer, evaporating an electron transport material on the hole blocking material, evaporating an electron injection material after the evaporation of the electron transport material is finished, sputtering a metal cathode, and finally carrying out a device packaging process in a general packaging device mode in the industry to prepare a sample of 30mm multiplied by 30mm serving as a test device, and then testing and detecting various luminous performance indexes of the sample.
Device comparative example 1:
the organic electroluminescent device is prepared according to the following steps:
Under high vacuum condition, indium tin oxide (anode 2) with the thickness of 20nm, moO 3 with the thickness of 10nm and HT-1 with the thickness of 60nm and the hole injection layer 3 are sequentially evaporated on a substrate of washed conductive glass (namely transparent substrate 1), and after the evaporation of the hole transport material is finished, a luminescent layer 5 of an OLED luminescent device is manufactured, wherein the structure of the luminescent layer 5 comprises BH-1 or BH-2 used by the OLED luminescent layer as a main material, DB-1 is used as a doping material, the doping proportion of the doping material is 5% by weight, and the thickness of the luminescent layer is 30nm. On the light-emitting layer, TPBI was vapor deposited, and the vacuum vapor deposited film thickness of the material was 30nm as the electron transport layer 6. On the electron transport layer, a LiF layer having a film thickness of 10nm, which is an electron injection layer 7, was produced by a vacuum vapor deposition apparatus. An Al electrode layer having a film thickness of 16nm, which is the cathode 8, was formed on the electron injection layer by a vacuum vapor deposition apparatus, and a device as shown in FIG. 1 was manufactured by this method.
Device example 1:
the procedure of device comparative example 1 was conducted except that the host light-emitting materials of the light-emitting layers were replaced with compound 1, respectively.
According to different functional layers as devices, the following can be divided: example 1, example 2, example 3, example 4, example 5, example 6, example 7, example 8, example 9 as a light-emitting layer; example 10, example 11, example 12 as a transport layer; examples 13, 14, 15, which serve as both the light-emitting layer host material and the electron transport material.
The conventional materials used in the preparation process of the device relate to the structure of the functional layer materials as follows:
wherein, the main body luminescent material of the control test device adopts the traditional main body luminescent material as the control, and the control main body luminescent material adopts BH-1 and BH-2 respectively.
TABLE 2
/>
As shown in table 2, from the device test data, compared with the traditional main body luminescent material and electron transport material, the test device prepared by using the compound as the main body luminescent material and electron transport material has the advantages that the driving voltage is obviously reduced, the luminescent brightness is obviously improved, and the efficiency of the whole device is effectively improved; therefore, the compound which is preferable in the invention is used as a main luminescent material and an electron transport material, plays a substantial role in improving the performance of the device, and has potential value for popularization and application.
The invention takes the purine structure as the parent nucleus, and through effective substitution modification of the 2,6 and 9 positions of the purine molecule, the compound molecule can be used as a main material and has high-efficiency electron transmission property.
The electroluminescent device made of the purine derivative has the advantages of reduced driving voltage, obviously improved luminous brightness, effectively improved overall device efficiency, and longer service life than the traditional material device.
The purine derivative provided by the invention is used as a main luminescent material of an electroluminescent device, and has better applicability and performance compared with the traditional main luminescent material.
The purine derivatives of the invention have good transmission effect when used as transmission materials in OLED devices.
The principle of the invention is as follows:
The invention uses the aromatic configuration of purine molecule main body skeleton containing multiple nitrogen atoms as kernel, its own charge distribution is asymmetric between two rings, then uses the substitution process of specific groups to its 2,6 and 9 positions to regulate its electron distribution, so that it can be used as high-effective electron-transport material for electron-transport layer, at the same time can be used as a main body luminescent material with excellent performance for luminescent layer.
The invention takes purine as a fixed inner core and carbazole as a fixed substituent, when the molecules are taken as a main luminescent material, the molecules have higher triplet excitation state energy, and the triplet excitation state energy can be effectively utilized in practical application, so that the luminescent power of the device is greatly improved.
The purine derivative provided by the invention is used as a main luminescent material and an electron transport material, so that the glass state film formed by the material is more stable, the maximum contact with the stability of a cathode material is realized, and the reliable and stable transport of electrons is ensured.
The purine derivative disclosed by the invention realizes the integration of luminescence and electron transmission of a device main body, can realize effective simplification of a device structure and reduces the cost.
While the preferred embodiments of the present invention have been described in detail, the present invention is not limited to the above embodiments, and various changes may be made without departing from the spirit of the present invention within the knowledge of those skilled in the art.
Many other changes and modifications may be made without departing from the spirit and scope of the invention. It is to be understood that the invention is not to be limited to the specific embodiments, but only by the scope of the appended claims.
Claims (9)
1. A purine derivative, characterized in that the purine derivative has the structural formula of formula 1:
Wherein R 1、R2 is independently selected from hydrogen, deuterium, fluorine, cyano, and alkyl or aryl substituted or unsubstituted between C 1～C10 carbon atoms; r 3、R4 is independently selected from C 2～C25 substituted or unsubstituted alkyl, cycloalkyl, phenyl, naphthyl, phenanthryl, biphenyl, pyridyl, quinolinyl, pyrrolyl, benzofuranyl or benzothienyl; r 5 is selected from substituted or unsubstituted heteroaryl.
2. A purine derivative according to claim 1, wherein said heteroaryl group comprises pyridyl, pyrazinyl, dibenzothienyl, dibenzofuranyl, benzothiazolyl, benzoxazolyl, pyrazolyl.
3. The purine derivative according to claim 2, wherein the general formula 1 comprises chemical formulas 1 to 7, and the specific structural formula is:
Wherein R 1、R2 is independently selected from hydrogen, deuterium, fluorine, cyano, and alkyl or aryl substituted or unsubstituted between C 1～C10 carbon atoms; r 3、R4 is independently selected from C 2～C25 substituted or unsubstituted alkyl, cycloalkyl, phenyl, naphthyl, phenanthryl, biphenyl, pyridyl, quinolinyl, pyrrolyl, benzofuranyl or benzothienyl.
4. A purine derivative according to claim 3, wherein said formula 1 comprises compounds 1 to 112, having the specific structural formula:
5. An electroluminescent device comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises any one or a combination of at least two of the compounds 1 to 112 of a purine derivative according to claim 4.
6. An electroluminescent device as claimed in claim 5, characterized in that: the organic layer comprises a hole transmission layer, a luminescent layer and an electron transmission layer, the first electrode and the second electrode are respectively a cathode and an anode, the hole transmission layer is positioned between the anode and the luminescent layer, the electron transmission layer is positioned between the cathode and the luminescent layer, and the main luminescent material of the luminescent layer is selected from any one or a combination of at least two of the compounds 1-112; the material of the electron transport layer is also selected from, but not limited to, any one or a combination of more of the compounds 1 to 112.
7. An electroluminescent device according to claim 6, wherein the first electrode is formed by sputtering or deposition on a substrate, and when the first electrode is used as an anode, it is selected from indium tin oxide, indium zinc oxide, tin dioxide, zinc oxide or any combination thereof; when the first electrode is used as a cathode, it is selected from the group consisting of magnesium, silver, aluminum-lithium, calcium, magnesium-indium, magnesium-silver metal or alloy, and any combination thereof.
8. An electroluminescent device as claimed in claim 6, characterized in that: the light-emitting layer is made of a main light-emitting material and a guest light-emitting material in a compounding way; the guest luminescent material is selected from
Ir(PPy)3 And the mass ratio of the host luminescent material to the guest luminescent material is 95:5.
9. An electroluminescent device as claimed in claim 6, characterized in that: the hole transport layer is made of one or any combination of HT-1, HT-2 and HT-3, and has the following structural formula:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202410103227.2A CN117946109A (en) | 2024-01-25 | 2024-01-25 | Purine derivative and electroluminescent device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202410103227.2A CN117946109A (en) | 2024-01-25 | 2024-01-25 | Purine derivative and electroluminescent device |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117946109A true CN117946109A (en) | 2024-04-30 |
Family
ID=90799431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202410103227.2A Pending CN117946109A (en) | 2024-01-25 | 2024-01-25 | Purine derivative and electroluminescent device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117946109A (en) |
-
2024
- 2024-01-25 CN CN202410103227.2A patent/CN117946109A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111808085B (en) | Compound and application thereof, and organic electroluminescent device comprising compound | |
| CN109928886B (en) | Compound containing triarylamine and fluorene and application thereof | |
| CN113816979B (en) | Organic compound and electroluminescent application thereof | |
| CN115991689B (en) | Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device | |
| CN112079834A (en) | Organic electroluminescent compound and application thereof | |
| CN110256428A (en) | A kind of compound, OLED display panel, display device | |
| CN115557920B (en) | Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device | |
| CN109336782B (en) | Fluorene derivative and organic electroluminescent device thereof | |
| CN116514752B (en) | Light-emitting auxiliary material, preparation method and application thereof in organic electroluminescent device | |
| CN111018898B (en) | Compound, display panel and display device | |
| CN115947706B (en) | Luminescent auxiliary material, preparation method and application | |
| CN114262328B (en) | Organic electroluminescent compound, preparation method thereof and organic electroluminescent device | |
| CN115894412B (en) | Organic electroluminescent compound, preparation method thereof and electroluminescent device | |
| CN115160273A (en) | Compound containing dibenzo heterocycle and preparation method and application thereof | |
| CN116023353A (en) | Light-emitting auxiliary material, preparation method thereof, organic electroluminescent device and application thereof | |
| CN114436754A (en) | Organic compound and application thereof | |
| CN117946109A (en) | Purine derivative and electroluminescent device | |
| CN111410657B (en) | Luminescent material and application thereof | |
| CN109678799B (en) | Dihydrobenzandazole compound, organic electroluminescent device and display device | |
| CN114716418B (en) | Heterocyclic alkane derivative, organic photoelectric device, and display or lighting device | |
| CN115160322B (en) | Hole organic electroluminescent compound and preparation method thereof | |
| CN113582986B (en) | Spiro compound, preparation method thereof, luminescent auxiliary material and organic electroluminescent device | |
| CN117777038B (en) | Organic electroluminescent material, preparation method thereof and organic electroluminescent device | |
| CN115521214B (en) | Organic compound, and electronic component and electronic device including the same | |
| CN115141144B (en) | Organic compound, organic electroluminescent device and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |