CN111153919B - Luminescent material, application thereof and organic electroluminescent device comprising luminescent material - Google Patents
Luminescent material, application thereof and organic electroluminescent device comprising luminescent material Download PDFInfo
- Publication number
- CN111153919B CN111153919B CN202010017691.1A CN202010017691A CN111153919B CN 111153919 B CN111153919 B CN 111153919B CN 202010017691 A CN202010017691 A CN 202010017691A CN 111153919 B CN111153919 B CN 111153919B
- Authority
- CN
- China
- Prior art keywords
- ring
- single bond
- compound
- formula
- bonded
- 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.)
- Active
Links
- 239000000463 material Substances 0.000 title claims abstract description 52
- 150000001875 compounds Chemical class 0.000 claims abstract description 155
- -1 nitro, hydroxyl Chemical group 0.000 claims abstract description 81
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 125000003118 aryl group Chemical group 0.000 claims abstract description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 20
- 125000001424 substituent group Chemical group 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 125000001769 aryl amino group Chemical group 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 9
- 229910052701 rubidium Inorganic materials 0.000 claims abstract description 9
- 229910052796 boron Inorganic materials 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 7
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
- 239000010410 layer Substances 0.000 claims description 90
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 9
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 125000001725 pyrenyl group Chemical group 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 3
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 3
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 2
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 2
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 2
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 claims description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 2
- 125000005266 diarylamine group Chemical group 0.000 claims 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 71
- 238000003786 synthesis reaction Methods 0.000 description 71
- 239000007787 solid Substances 0.000 description 33
- 239000000126 substance Substances 0.000 description 21
- 150000001793 charged compounds Chemical class 0.000 description 18
- 238000000921 elemental analysis Methods 0.000 description 18
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 18
- 238000004128 high performance liquid chromatography Methods 0.000 description 17
- 150000001412 amines Chemical class 0.000 description 16
- 230000005525 hole transport Effects 0.000 description 16
- 150000004820 halides Chemical class 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 11
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000005309 thioalkoxy group Chemical group 0.000 description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000008204 material by function Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000007725 thermal activation Methods 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- IRPWVEBIMPXCAZ-UHFFFAOYSA-N 1,3-dibromo-2-chlorobenzene Chemical compound ClC1=C(Br)C=CC=C1Br IRPWVEBIMPXCAZ-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000003341 Bronsted base Substances 0.000 description 1
- PPQUVWSPDPMRFN-UHFFFAOYSA-N CC(C)(C)[Mg]CC1=CC=CC=C1 Chemical compound CC(C)(C)[Mg]CC1=CC=CC=C1 PPQUVWSPDPMRFN-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 238000010268 HPLC based assay Methods 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- PPTSBERGOGHCHC-UHFFFAOYSA-N boron lithium Chemical compound [Li].[B] PPTSBERGOGHCHC-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012761 high-performance material Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- YAMQOOCGNXAQGW-UHFFFAOYSA-M magnesium;methylbenzene;bromide Chemical compound [Mg+2].[Br-].CC1=CC=CC=[C-]1 YAMQOOCGNXAQGW-UHFFFAOYSA-M 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000006263 metalation reaction Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
- C09K2211/107—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with other heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
- C09K2211/1085—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms with other heteroatoms
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to a novel compound, application thereof and an organic electroluminescent device containing the compound, wherein the compound has a structure shown in the following formula:
wherein, Y1And Y2Are independently N or B, X1、X2、X3And X4Are each independently of the other NR1Or BR2，Ra、Rb、RcAnd RdEach independently represents a single substituent up to the maximum permissible substituents, and each is independently selected from hydrogen, deuterium, or one of the following substituted or unsubstituted groups: one of C1-C36 chain alkyl, C3-C36 cycloalkyl, C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl. The compound of the present invention shows excellent device performance and stability when used as a light emitting material in an OLED device. The invention also protects the organic electroluminescent device adopting the compound with the general formula.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a novel organic compound, application thereof and an organic electroluminescent device containing the compound.
Background
Organic Light Emission Diodes (OLED) are a kind of devices with sandwich-like structure, which includes positive and negative electrode films and Organic functional material layers sandwiched between the electrode films. Because the OLED device has the advantages of high brightness, fast response, wide viewing angle, simple process, flexibility and the like, the OLED device is concerned in the field of novel display technology and novel illumination technology. At present, the technology is widely applied to display panels of products such as novel lighting lamps, smart phones and tablet computers, and further expands the application field of large-size display products such as televisions, and is a novel display technology with fast development and high technical requirements.
As OLEDs continue to advance in both lighting and display areas, much attention has been paid to research into their core materials, since an efficient, long-lived OLED device is generally the result of an optimized arrangement of device structures and various organic materials. In order to prepare an OLED light-emitting device with lower driving voltage, better light-emitting efficiency and longer service life, the performance of the OLED device is continuously improved, the structure and the manufacturing process of the OLED device need to be innovated, and photoelectric functional materials in the OLED device need to be continuously researched and innovated, so that functional materials with higher performance can be prepared. Based on this, the OLED material industry has been working on developing new organic electroluminescent materials to achieve low starting voltage, high luminous efficiency and better lifetime of the device.
In the aspect of selection of OLED materials, the fluorescent material with singlet state luminescence has the advantages of long service life, low price and low efficiency; triplet-emitting phosphorescent materials are efficient, but expensive, and the problem of lifetime of blue materials has not been solved. Adachi at kyushu university of japan proposes a new class of organic light emitting materials, i.e., Thermally Activated Delayed Fluorescence (TADF) materials. Singlet-triplet energy gap (Delta E) of the materialST) Very small (<0.3eV), triplet excitons may be converted into singlet excitons by reverse intersystem crossing (RISC) to emit light, and thus the internal quantum efficiency of the device may reach 100%.
The MR-TADF material has the advantages of high color purity and high luminous efficiency, and has attracted extensive attention in the scientific research and industrial fields. However, due to the pair of peripheral substituents S1The energy level influence is small, namely the luminous color of the material is difficult to regulate and control, the light color of the material is always limited in a blue-deep blue region, and the further application of the MR-TADF material in the fields of high-resolution display, full-color display, white light illumination and the like is greatly limited.
Disclosure of Invention
In order to solve the above technical problems, the present invention provides a novel organic compound, wherein the specific general formula of the compound of the present invention is shown as the following formula (1):
in the formula (I), ring A, ring B, ring C and ring D each independently represent an aromatic ring or a heteroaromatic ring;
said Y is1And Y2Each is independently N or B; said X1、X2、X3And X4Are each independently NR1Or BR2；
The R is1Rings A and/or R which are each independently optionally adjacent theretoaRing B and/or RbRing C and/or RcOr ring D and/or RdLinked to form a ring or not linked to form a ring, wherein the linkage to form a ring may be through-O-, -S-, -CR3R4-or a single bond;
the R is2Rings A and/or R which are each independently optionally adjacent theretoaRing B and/or RbRing C and/or RcOr ring D and/or RdLinked to form a ring or not linked to form a ring, wherein the linkage to form a ring may be through-O-, -S-, -CR3R4-or a single bond;
the R is1、R2、R3And R4Each independently selected from one of the following substituted or unsubstituted groups: C1-C36 chain alkyl, C3-C36 cycloalkyl, C6-C30 arylamine, C3-C30 heteroarylamino, C6-C60 monocyclic aryl, C6-C60 fused ring aryl, C6-C60 aryloxy, C5-C60 monocyclic heteroaryl or C5-C60 fused ring heteroaryl;
the R isa、Rb、RcAnd RdEach independently represents a single substituent up to the maximum permissible substituents, and each is independently selected from hydrogen, deuterium, or one of the following substituted or unsubstituted groups: halogen, chain alkyl of C1-C36, cycloalkyl of C3-C36, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano, amino, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl of C6-C60, condensed ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60, condensed ring heteroaryl of C5-C60One kind of (1);
the R isa、Rb、R cAnd RdMay be bonded to each other and may correspondingly form, together with ring A, ring B, ring C or ring D, a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C3-C30 heteroaryl group;
when the above groups have substituents, the substituents are respectively and independently selected from any one of deuterium, halogen, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano, amino, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl of C6-C60, condensed ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60 and condensed ring heteroaryl of C5-C60.
Preferably, at least one hydrogen in the structural formula of the compound represented by the formula (I) is substituted.
Preferably, ring A, ring B, ring C and ring D in formula (I) each independently represent any one of monocyclic aromatic ring or fused aromatic ring of C5-C20, monocyclic heterocyclic ring or fused heterocyclic ring of C4-C20; still preferably, the a, ring B, ring C and ring D each independently represent any one of a monocyclic aromatic ring or a fused aromatic ring of C5 to C10, a monocyclic heterocyclic ring or a fused heterocyclic ring of C4 to C10; most preferably, the a, ring B, ring C and ring D are each independently selected from any one of a benzene ring, a naphthalene ring or a fluorene ring.
Preferably, the specific general formula of the compound of the present invention is shown in the following formula (1):
said Y is1And Y2Each is independently N or B; said X1、X2、X3And X4Are each independently NR1Or BR2；
The R is1Ring a and/or R independently and adjacently adjacent to each otheraRing b and/or RbRing c and/or RcOr ring d and/or RdLinked to form a ring or not linked to form a ring, wherein the linkage to form a ring may be through-O-, -S-, -CR3R4-or a single bond;
the R is2Ring a and/or R independently and adjacently adjacent to each otheraRing b and/or RbRing c and/or RcOr ring d and/or RdLinked to form a ring or not linked to form a ring, wherein the linkage to form a ring may be through-O-, -S-, -CR3R4-or a single bond;
the R isa、Rb、Rc、Rd、R3And R4Are as defined in formula (I).
Still preferably, the specific general formula of the compound of the present invention is represented by any one of the following formulas (2) to (4):
in formulae (2) to (4), X1、X2、X3、X4、Ra、Rb、RcAnd RdAre as defined in formula (I).
More preferably, the specific general formula of the compound of the present invention is represented by formula (2), wherein in formula (2), X is1、X2、X3And X4Are each independently NR1，Ra、Rb、RcAnd RdAre as defined in formula (I).
More preferably, the specific general formula of the compound of the present invention is represented by formula (3), wherein in formula (3), X is1、X2Are each independently NR1，X3、X4Are respectively independent and are respectively BR2，Ra、Rb、RcAnd RdAre as defined in formula (I).
More preferably, the specific general formula of the compound of the present invention is represented by formula (4), wherein in formula (4), X1、X2、X3And X4Are respectively independent and are respectively BR2，Ra、Rb、RcAnd RdAre as defined in formula (I).
Still more preferably, in the above general formulae (1) to (4) of the present invention, R is1Rings a and/or R independently adjacent theretoaRing b and/or RbRing c and/or RcOr ring d and/or RdWhen the connection is performed to form a ring, the connection is performed through a single bond; the R is2Rings a and/or R independently adjacent theretoaRing b and/or RbRing c and/or RcOr ring d and/or RdWhen they are linked to form a ring, they are linked by a single bond.
More preferably, in the above general formulae (1) to (4) of the present invention, R isa、Rb、RcAnd RdEach independently selected from hydrogen, deuterium, or one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2, 2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, grottoyl, perylenyl, anthrylenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenylenyl, trimeric indenyl, isotridecylinyl, trimeric spiroindenyl, spiromesityl, spiroisotridecylinyl, furanyl, isobenzofuranyl, phenyl, terphenyl, anthryl, terphenyl, pyrenyl, terphenyl, terp, Dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolylPyridoimidazolyl, pyrazinoyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthracenyl, phenanthroxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazanthronyl, 2, 7-diazepyryl, 2, 3-diazepyryl, 1, 6-diazepyryl, 1, 8-diazepyryl, 4,5,9, 10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, 9-dimethylazinyl, triarylamino, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy, silyl, or a combination of two substituents selected therefrom;
when the above groups have substituents, the substituents are respectively and independently selected from any one of halogen, chain alkyl of C1-C12, cycloalkyl of C3-C12, alkoxy or thioalkoxy of C1-C6, arylamino of C6-C30, heteroaryl of C3-C30, monocyclic aromatic hydrocarbon or fused ring aromatic hydrocarbon group of C6-C30, monocyclic heteroaromatic hydrocarbon or fused ring heteroaromatic hydrocarbon group of C3-C30.
Still further preferably, the specific general formula of the compound of the present invention is represented by any one of the formulae (5) to (7):
in formulae (5) to (7), the R1～R24Each independently selected from hydrogen, deuterium, or one of the following substituted or unsubstituted groups: halogen, chain alkyl of C1-C36, and cycloalkyl of C3-C36C1-C10 alkoxy, C1-C10 thioalkoxy, carbonyl, carboxyl, nitro, cyano, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C60 monocyclic aryl, C6-C60 fused ring aryl, C6-C60 aryloxy, C5-C60 monocyclic heteroaryl, C5-C60 fused ring heteroaryl, and R is R1～R24Wherein adjacent two groups may be bonded to each other to form a single bond, or may be bonded to form, together with an adjacent benzene ring, one of a substituted or unsubstituted C5-C30 five-or six-membered aryl ring, a substituted or unsubstituted C5-C30 five-or six-membered heteroaryl ring;
z is1And Z2Each independently selected from hydrogen or a single bond. Preferably, Z1Is a single bond, Z2Is hydrogen; or preferably, Z2Is a single bond, Z1Is hydrogen; or preferably, Z1And Z2Are all hydrogen; or preferably, Z1And Z2Are all single bonds.
Further, the compound represented by the general formula (1) of the present invention may preferably be a compound having the following specific structure: p-1 to P-544, these compounds being representative only:
the present invention also provides an organic electroluminescent device comprising a substrate comprising a first electrode, a second electrode and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer comprises a compound represented by any one of the above general formula (i), general formula (1) to formula (7).
Specifically, embodiments of the present invention provide an organic electroluminescent device including a substrate, and an anode layer, a plurality of light emitting functional layers, and a cathode layer sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is arranged between the hole transport layer and the electron transport layer; among them, the light-emitting layer preferably contains the compound of the general formula of the present invention represented by any one of the general formula (i) and the general formulae (1) to (7).
The specific reason why the above-mentioned compound of the present invention is excellent as an electron transport layer material in an organic electroluminescent device is not clear, and the following reason is presumed:
the general formula compound (shown in the following formula) of the invention is used for amplifying a conjugated framework of a classical MR-TADF material, introducing more nitrogen atoms or boron atoms, realizing the obvious red shift behavior of a target MR-TADF material while keeping the large HOMO and LUMO orbits of a BN rigid framework overlapped, and obtaining the emission of green light, yellow light and even red light.
The OLED device prepared by the compound has narrow half-peak width and shows obvious multiple resonance effect, thereby greatly enriching the material system of multiple resonance-thermal activation delayed fluorescence and the range of luminescent color; the high-performance light-emitting diode has low starting voltage, high light-emitting efficiency and better service life, can meet the requirements of current panel manufacturing enterprises on high-performance materials, and shows good application prospects.
Drawings
FIG. 1: the structure of the organic electroluminescent device prepared by the invention is shown in the figure, wherein 1 is a substrate, 2 is an anode, 3 is a hole transport layer, 4 is an organic luminescent layer, 5 is an electron transport layer, and 6 is a cathode.
Detailed Description
The specific production method of the above-mentioned novel compound of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the production method of the present invention is not limited to these synthesis examples.
Basic chemical raw materials of various chemicals used in the present invention, such as petroleum ether, tert-butylbenzene, ethyl acetate, sodium sulfate, toluene, dichloromethane, potassium carbonate, boron tribromide, N-diisopropylethylamine, reaction intermediate, and the like, are commercially available from shanghai tatarian technologies ltd and silong chemical ltd. The mass spectrometer used for determining the following compounds was a ZAB-HS type mass spectrometer measurement (manufactured by Micromass, UK).
In the following, briefly describing the method for synthesizing the compound of the present invention, X is first synthesized using n-butyllithium, t-butyllithium or the like1、X2、X3And X4The hydrogen and Cl atoms between/on the surface are subjected to ortho-metallation. Subsequently, boron tribromide is added to perform lithium-boron metal exchange, and then Bronsted base (e.g., N-diisopropylethylamine) is added to perform Tandem boron hybrid-krafts Reaction (Tandem Bora-Friedel-Crafts Reaction), thereby obtaining the target product.
More specifically, the following gives a synthetic method of a representative specific compound of the present invention.
Synthetic examples
Synthesis example 1:
synthesis of Compound P-4-1
To a 100 ml two-necked flask, amine (3.00g, 11.52mmol), 1, 3-dibromo-2-chlorobenzene (3.12g, 11.52mmol), sodium tert-butoxide (2.77g, 28.81mmol), tri-tert-butylphosphine (70mg, 0.35mmol), palladium acetate (100mg, 0.46mmol), and 40 ml of toluene were added in this order under a nitrogen atmosphere, and the reaction was stopped after 12 hours at 90 ℃. Cooled to room temperature, 50 ml of ethanol are added, and the mixture is filtered with suction. The filter cake was washed successively with water and ethanol to give white powder P-4-1(3.4 g).
Synthesis of Compound P-4
A solution of tert-butyllithium in pentane (11.18mL, 1.60M, 17.89mmol) was slowly added to a 0 ℃ solution of P-4-1(3.00g, 4.07mmol) in tert-butylbenzene (60mL), and the reaction was then allowed to warm to 60 ℃ for 3 hours each. After the reaction was complete, the temperature was reduced to-30 ℃ and boron tribromide (4.48g, 17.89mmol) was slowly added and stirring continued at room temperature for 0.5 h. N, N-diisopropylethylamine (3.15g, 24.40mmol) was added at room temperature and the reaction was continued at 145 ℃ for 5 hours and stopped. The solvent was spun dry in vacuo and passed through a silica gel column (developing solvent: ethyl acetate: petroleum ether: 50:1) to give the title compound P-4(0.28g, 10% yield, 99.46% analytical purity by HPLC) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 680.36 elemental analysis results: theoretical value: c, 84.74; h, 3.85; b, 3.18; n,8.23 (%); experimental values: c, 84.64; h, 3.85; b, 3.28; n,8.23 (%).
Synthesis example 2:
synthesis of Compound P-19-1
This example is essentially the same as the synthesis of compound P-4-1, except that: in this case, an amine replacing the desired substance. The objective compound P-19-1(3.6g) was a white solid.
Synthesis of Compound P-19
This example is essentially the same as the synthesis of compound P-4, except that: in this case, P-4-1 is replaced by P-19-1 in an equal amount. The title compound P-19(0.18g, 6% yield, 99.75% purity by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 736.46 elemental analysis results: theoretical value: c, 84.80; h, 4.65; b, 2.94; n,7.61 (%); experimental values: c, 84.90; h, 4.55; b, 2.84; n,7.71 (%).
Synthetic example 3:
synthesis of Compound P-9-1
This example is essentially the same as the synthesis of compound P-4-1, except that: in this case, amines and halides are substituted for the desired substances. The objective compound P-9-1(3.2g) was a white solid.
Synthesis of Compound P-9
This example is essentially the same as the synthesis of compound P-4, except that: in this case, P-4-1 is replaced by P-9-1 in an equal amount. The title compound, P-9(0.22g, 8% yield, 99.66% purity by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 676.38 elemental analysis results: theoretical value: c, 85.24; h, 3.28; b, 3.20; n,8.28 (%); experimental values: c, 85.14; h, 3.38; b, 3.30; n,8.18 (%).
Synthetic example 4:
synthesis of Compound P-63-1
This example is essentially the same as the synthesis of compound P-4-1, except that: in this case, amines and halides are substituted for the desired substances. The objective compound P-63-1(4.8g) was a white solid.
Synthesis of Compound P-63
This example is essentially the same as the synthesis of compound P-4, except that: in this case, P-4-1 is replaced by P-63-1 in an amount equivalent to the amount of the substance. The title compound, P-9(0.48g, 12% yield, 99.36% purity by HPLC), was an orange-red solid. MALDI-TOF-MS results: molecular ion peaks: 980.75 elemental analysis results: theoretical value: c, 88.18; h, 3.91; b, 2.20; n,5.71 (%); experimental values: c, 88.28; h, 3.91; b, 2.30; n,5.51 (%).
Synthesis example 5:
synthesis of Compound P-155-1
This example is essentially the same as the synthesis of compound P-4-1, except that: in this case, amines and halides are substituted for the desired substances. The objective compound P-155-1(3.9g) was a white solid.
Synthesis of Compound P-62
This example is essentially the same as the synthesis of compound P-4, except that: in this case, P-4-1 is replaced by P-62-1 in an equal amount. The title compound, P-9(0.23g, 8% yield, 99.85% purity by HPLC) was an orange-red solid. MALDI-TOF-MS results: molecular ion peaks: 712.52 elemental analysis results: theoretical value: c, 80.94; h, 2.83; b, 3.04; f, 5.33; n,7.87 (%); experimental values: c, 80.92; h, 2.82; b, 3.04; f, 5.34; n,7.87 (%).
Synthetic example 6:
synthesis of Compound P-5-1
This example is essentially the same as the synthesis of compound P-4-1, except that: in this case, amines and halides are substituted for the desired substances. The objective compound P-5-1(4.2g) was a white solid.
Synthesis of Compound P-62
This example is essentially the same as the synthesis of compound P-4, except that: in this case, P-4-1 is replaced by P-5-1 in an equivalent amount. The title compound, P-9(0.23g, 8% yield, 99.85% purity by HPLC) was an orange-red solid. MALDI-TOF-MS results: molecular ion peaks: 676.02 elemental analysis results: theoretical value: c, 85.24; h, 3.28; b, 3.20; n,8.28 (%); experimental values: c, 85.14; h, 3.28; b, 3.30; n,8.28 (%).
Synthetic example 7:
synthesis of Compound P-62-1
This example is essentially the same as the synthesis of compound P-4-1, except that: in this case, amines and halides are substituted for the desired substances. The objective compound P-62-1(4.6g) was a white solid.
Synthesis of Compound P-62
This example is essentially the same as the synthesis of compound P-4, except that: in this case, P-4-1 is replaced by P-62-1 in an equal amount. The title compound, P-9(0.36g, 9% yield, 99.55% purity by HPLC), was an orange-red solid. MALDI-TOF-MS results: molecular ion peaks: 980.65 elemental analysis results: theoretical value: c, 88.18; h, 3.91; b, 2.20; n,5.71 (%); experimental values: c, 88.18; h, 3.91; b, 2.20; n,5.71 (%).
Synthesis example 8:
synthesis of Compound P-154-1
This example is essentially the same as the synthesis of compound P-4-1, except that: in this case, amines and halides are substituted for the desired substances. The objective compound P-154-1(3.6g) was a white solid.
Synthesis of Compound P-154
This example is essentially the same as the synthesis of compound P-4, except that: in this case, P-4-1 is replaced by P-154-1 in an equal amount. The title compound, P-9(0.20g, 7% yield, 99.38% purity by HPLC), was an orange-red solid. MALDI-TOF-MS results: molecular ion peaks: 1002.02 elemental analysis results: theoretical value: c, 80.94; h, 2.83; b, 3.04; f, 5.33; n,7.87 (%); experimental values: c, 80.94; h, 2.85; b, 3.04; f, 5.31; n,7.86 (%).
Synthetic example 9:
synthesis of Compound P-177-1
This example is essentially the same as the synthesis of compound P-4-1, except that: in this case, amines and halides are substituted for the desired substances. The objective compound P-177-1(3.6g) was a white solid.
Synthesis of Compound P-177
A solution of tert-butyllithium in pentane (18.59mL, 1.60M, 29.75mmol) was slowly added to a 0 deg.C solution of P-177-1(3.00g, 4.96mmol) in tert-butylbenzene (60mL), and the reaction was then allowed to warm to 60 deg.C in sequence for 3 hours each. After the reaction was complete, the temperature was reduced to-30 ℃ and boron tribromide (3.73g, 14.88mmol) was slowly added and stirring was continued at room temperature for 0.5 hour. N, N-diisopropylethylamine (1.92g, 14.88mmol) was added at room temperature and the reaction was continued at 145 ℃ for 12 hours and then cooled to room temperature, whereupon phenylmagnesium bromide (2.70g, 14.88mmol) was added and the reaction was stopped after 2 hours. The solvent was spun off in vacuo and passed through a silica gel column (developing solvent: ethyl acetate: petroleum ether: 50:1) to give the title compound P-177(0.17g, 5% yield, HPLC assay purity 99.32%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 681.35 elemental analysis results: theoretical value: c, 84.63; h, 4.44; b, 4.76; n,6.17 (%); experimental values: c, 84.64; h, 4.43; b, 4.66; n,6.27 (%).
Synthetic example 10:
synthesis of Compound P-237-1
This example is essentially the same as the synthesis of compound P-4-1, except that: in this case, amines and halides are substituted for the desired substances. The objective compound, P-237-1(5.6g), was a white solid.
Synthesis of Compound P-237
This example is essentially the same as the synthesis of compound P-177, except that: in this case, P-177-1 is replaced by P-237-1 in an equal amount. The title compound, P-237(0.18g, 4.5% yield, 99.28% purity by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 833.02 elemental analysis results: theoretical value: c, 86.47; h, 4.60; b, 3.89; n,5.04 (%); experimental values: c, 86.47; h, 4.50; b, 3.89; n,5.14 (%).
Synthetic example 11:
synthesis of Compound P-179-1
This example is essentially the same as the synthesis of compound P-4-1, except that: in this case, amines and halides are substituted for the desired substances. The title compound, P-179-1(3.6g), was a white solid.
Synthesis of Compound P-179
This example is essentially the same as the synthesis of compound P-4, except that: in this case, P-4-1 is replaced by P-179-1 in an amount equivalent to that of the substance. The title compound P-179(0.16g, 6% yield, 99.63% purity by HPLC) was an orange yellow solid. MALDI-TOF-MS results: molecular ion peaks: 677.02 elemental analysis results: theoretical value: c, 85.14; h, 3.87; b, 4.79; n,6.21 (%); experimental values: c, 85.24; h, 3.77; b, 4.78; n,6.21 (%).
Synthetic example 12:
synthesis of Compound P-185-1
This example is essentially the same as the synthesis of compound P-4-1, except that: in this case, amines and halides are substituted for the desired substances. The objective compound P-185-1(4.6g) was a white solid.
Synthesis of Compound P-185
This example is essentially the same as the synthesis of compound P-177, except that: in this case, P-177-1 is replaced by P-185-1 in equal amount. The title compound P-185(0.22g, 6.6% yield, 99.52% purity by HPLC) was an orange yellow solid. MALDI-TOF-MS results: molecular ion peaks: 673.02 elemental analysis results: theoretical value: c, 85.65; h, 3.29; b, 4.82; n,6.24 (%); experimental values: c, 85.66; h, 3.19; b, 4.81; n,6.34 (%).
Synthetic example 13:
synthesis of Compound P-187-1
This example is essentially the same as the synthesis of compound P-4-1, except that: in this case, amines and halides are substituted for the desired substances. The objective compound, P-187-1(4.6g), was a white solid.
Synthesis of Compound P-187
This example is essentially the same as the synthesis of compound P-4, except that: in this example, P-4-1 is replaced by P-187-1 in an amount equivalent to the amount of the substance. The title compound, P-187(0.22g, 8% yield, 99.48% purity by HPLC), was an orange-red solid. MALDI-TOF-MS results: molecular ion peaks: 673.02 elemental analysis results: theoretical value: c, 85.65; h, 3.29; b, 4.82; n,6.24 (%); experimental values: c, 85.55; h, 3.19; b, 4.92; n,6.34 (%).
Synthesis example 14:
synthesis of Compound P-353-1
This example is essentially the same as the synthesis of compound P-4-1, except that: in this case, amines and halides are substituted for the desired substances. The title compound, P-353-1(3.1g), was a white solid.
Synthesis of Compound P-353
A solution of tert-butyllithium in pentane (18.59mL, 1.60M, 29.75mmol) was slowly added to a 0 deg.C solution of P-353-1(2.34g, 4.96mmol) in tert-butylbenzene (60mL), and the reaction was then allowed to warm to 60 deg.C in sequence for 3 hours each. After the reaction was complete, the temperature was reduced to-30 ℃ and boron tribromide (4.97g, 19.82mmol) was slowly added and stirring continued at room temperature for 0.5 h. N, N-diisopropylethylamine (2.56g, 19.82mmol) was added at room temperature and the reaction was continued at 145 ℃ for 12 hours and then cooled to room temperature, whereupon phenylmagnesium bromide (3.59g, 19.82mmol) was added and the reaction was stopped after 2 hours. The solvent was spun dry in vacuo and passed through a silica gel column (developing solvent: ethyl acetate: petroleum ether: 50:1) to give the title compound P-353(0.30g, 9% yield, 99.62% analytical purity by HPLC) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 678.42 elemental analysis results: theoretical value: c, 85.03; h, 4.46; b, 6.38; n,4.13 (%); experimental values: c, 85.13; h, 4.46; b, 6.28; n,4.13 (%).
Synthetic example 15:
synthesis of Compound P-368
This example is essentially the same as the synthesis of compound P-347, except that: in this case, the phenylmagnesium bromide was replaced by an equivalent amount of tolylmagnesium bromide. The title compound, P-9(0.29g, 8% yield, 99.28% purity by HPLC) was a green solid. MALDI-TOF-MS results: molecular ion peaks: 734.25 elemental analysis results: theoretical value: c, 85.08; h, 5.22; b, 5.89; n,3.82 (%); experimental values: c, 85.18; h, 5.22; b, 5.79; n,3.82 (%).
Synthetic example 16:
synthesis of Compound P-398
This example is essentially the same as the synthesis of compound P-353, except that: in this case, the phenylmagnesium bromide is replaced by the same amount of tert-butylbenzylmagnesium bromide. The title compound P-398(0.40g, 9% yield, 99.44% purity by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 902.02 elemental analysis results: theoretical value: c, 85.18; h, 6.93; b, 4.79; n,3.10 (%); experimental values: c, 85.08; h, 6.93; b, 4.79; n,3.20 (%).
Synthetic example 17:
synthesis of Compound P-359-1
This example is essentially the same as the synthesis of compound P-4-1, except that: in this case, amines and halides are substituted for the desired substances. The objective compound P-359-1(3.5g) was a white solid.
Synthesis of Compound P-62
This example is essentially the same as the synthesis of compound P-347, except that: in this case, P-347-1 is replaced by P-359-1 in an equal amount. The title compound P-359(0.22g, 6.6% yield, 99.34% purity by HPLC) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 674.02 elemental analysis results: theoretical value: c, 85.54; h, 3.89; b, 6.42; n,4.16 (%); experimental values: c, 85.64; h, 3.89; b, 6.32; n,4.16 (%).
Synthetic example 18:
synthesis of Compound P-363-1
This example is essentially the same as the synthesis of compound P-4-1, except that: in this case, amines and halides are substituted for the desired substances. The objective compound P-363-1(3.6g) was a white solid.
Synthesis of Compound P-363
This example is essentially the same as the synthesis of compound P-347, except that: in this case, P-347-1 is replaced by an equivalent amount of P-363-1. The title compound P-363(0.26g, 8% yield, 99.74% purity by HPLC) was an orange yellow solid. MALDI-TOF-MS results: molecular ion peaks: 670.02 elemental analysis results: theoretical value: c, 86.05; h, 3.31; b, 6.45; n,4.18 (%); experimental values: c, 86.15; h, 3.21; b, 6.46; n,4.17 (%).
The technical effects and advantages of the invention are shown and verified by testing practical use performance by specifically applying the compound of the invention to an organic electroluminescent device.
The organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer between the two electrodes. The organic material may be divided into a plurality of regions, for example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
As a material of the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO2), or zinc oxide (ZnO), or any combination thereof can be used. The cathode may be made of magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives, and the like.
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
The preparation process of the organic electroluminescent device is described as follows with reference to the attached figure 1: an anode 2, a hole transport layer 3, an organic light emitting layer 4, an electron transport layer 5, and a cathode 6 are sequentially deposited on a substrate 1, and then encapsulated. In the preparation of the organic light-emitting layer 4, the organic light-emitting layer 4 is formed by a co-deposition method using a wide band gap material source, an electron donor material source, an electron acceptor material source, and a resonance TADF material source.
Specifically, the preparation method of the organic electroluminescent device comprises the following steps:
1. the anode material coated glass plate was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
2. placing the glass plate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, forming a hole injection layer by vacuum evaporation of a hole injection material on the anode layer film, wherein the evaporation rate is 0.1-0.5 nm/s;
3. vacuum evaporating hole transport material on the hole injection layer to form a hole transport layer with an evaporation rate of 0.1-0.5nm/s,
4. vacuum evaporating an electron blocking layer on the hole transport layer, wherein the evaporation rate is 0.1-0.5 nm/s;
5. the organic light-emitting layer of the device is vacuum evaporated on the electron barrier layer, the organic light-emitting layer material comprises a main material and TADF dye, and the evaporation rate of the main material, the evaporation rate of the sensitizer material and the evaporation rate of the dye are adjusted by a multi-source co-evaporation method to enable the dye to reach a preset doping proportion;
6. vacuum evaporating a hole blocking layer on the organic light-emitting layer, wherein the evaporation rate is 0.1-0.5 nm/s;
7. forming an electron transport layer on the hole blocking layer by vacuum evaporation of an electron transport material of the device, wherein the evaporation rate is 0.1-0.5 nm/s;
8. LiF is evaporated on the electron transport layer in vacuum at a speed of 0.1-0.5nm/s to serve as an electron injection layer, and an Al layer is evaporated on the electron transport layer in vacuum at a speed of 0.5-1nm/s to serve as a cathode of the device.
The embodiment of the invention also provides a display device which comprises the organic electroluminescent device provided as above. The display device can be specifically a display device such as an OLED display, and any product or component with a display function including the display device, such as a television, a digital camera, a mobile phone, a tablet computer, and the like. The display device has the same advantages as the organic electroluminescent device compared with the prior art, and the description is omitted here.
The organic electroluminescent device according to the invention is further illustrated by the following specific examples.
Device example 1
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％P-4(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, the total thickness is generally 5-30nm, and the thickness is 10nm in the embodiment; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, 40nm in this embodiment; host is a main body material with wide band gap of an organic light-emitting layer, the compound P-4 of the invention is dye and the doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
A DC voltage was applied to the organic electroluminescent element D1 prepared in this example, and 10cd/m was measured2The characteristics in light emission were such that yellow light emission (driving voltage of 2.6V) having a wavelength of 545nm, a half-peak width of 38nm, CIE color coordinates (x, y) (0.36,0.62), and an external quantum efficiency EQE of 28.8% was obtained.
Device example 2
The same preparation method as that of the device example 1 except that the wide band gap type Host material used in the light emitting layer was replaced with the TADF type Host TD, the specific device structure was as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％P-4(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D2 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were such that yellow light emission (driving voltage of 2.4V) having a wavelength of 548nm, a half-peak width of 41nm, CIE color coordinates (x, y) ═ 0.37,0.63, and an external quantum efficiency EQE of 31.4% was obtained.
Device example 3
The same procedure as in device example 1 was followed except that the dye used in the light-emitting layer was replaced with P-19 from P-4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％P-19(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D3 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were such that yellow light emission (drive voltage of 2.6V) having a wavelength of 548nm, a half-peak width of 40nm, CIE color coordinates (x, y) (0.37,0.64), and an external quantum efficiency EQE of 28.3% was obtained.
Device example 4
The same preparation method as that of device example 1 was used except that the wide band gap type Host material Host in the light-emitting layer was replaced with TADF type Host TD and the dye was replaced with P-4 to P-19. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％P-19(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D4 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were such that yellow light emission (drive voltage of 2.6V) having a wavelength of 550nm, a half-width of 42nm, CIE color coordinates (x, y) (0.38,0.64), and an external quantum efficiency EQE of 30.4% was obtained.
Device example 5
The same procedure as in device example 1 was followed except that the dye in the light-emitting layer was replaced with P-9 from P-4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％P-9(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D5 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were such that yellow light emission (driving voltage of 2.6V) having a wavelength of 555nm, a half-peak width of 35nm, CIE color coordinates (x, y) (0.37,0.63), and external quantum efficiency EQE of 29.3% was obtained.
Device example 6
The same preparation method as that of device example 1 was used except that the wide band gap type Host material Host in the light-emitting layer was replaced with TADF type Host TD and the dye was replaced with P-4 to P-9. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％P-9(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D6 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were such that yellow light emission (driving voltage of 2.6V) with a wavelength of 557nm, a peak width at half maximum of 37nm, CIE color coordinates (x, y) (0.37,0.62), and an external quantum efficiency EQE of 33.6% was obtained.
Device example 7
The same procedure as in device example 1 was followed except that the dye in the light-emitting layer was replaced with P-5 from P-4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％P-5(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D7 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were that orange-yellow light emission (driving voltage of 2.8V) having a wavelength of 575nm, a half-width of 42nm, CIE color coordinates (x, y) (0.41,0.61), and external quantum efficiency EQE of 23.3% was obtained.
Device example 8
The same preparation method as that of device example 1 was used except that the wide band gap type Host material Host in the light-emitting layer was replaced with TADF type Host TD and the dye was replaced with P-4 to P-5. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％P-5(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D8 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were such that orange emission (driving voltage of 2.4V) with a wavelength of 577nm, a half-peak width of 44nm, CIE color coordinates (x, y) ═ 0.41,0.60, and an external quantum efficiency EQE of 27.4% was obtained.
Device example 9
The same procedure as in device example 1 was followed except that the dye in the light-emitting layer was replaced with P-177 from P-4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％P-177(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D9 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The green emission (driving voltage of 2.8V) having a wavelength of 526nm, a half-peak width of 41nm, CIE color coordinates (x, y) (0.32,0.61), and an external quantum efficiency EQE of 28.3% was obtained as characteristics in the emission.
Device example 10
The same preparation method as that of device example 1 was used except that the wide band gap type Host material Host in the light-emitting layer was replaced with TADF type Host TD and the dye was replaced with P-177 from P-4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％P-177(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D10 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The green emission (driving voltage of 2.4V) having a wavelength of 528nm, a half-width of 45nm, CIE color coordinates (x, y) ═ 0.32,0.60, and an external quantum efficiency EQE of 31.4% was obtained as characteristics in the emission.
Device example 11
The same procedure as in device example 1 was followed except that the dye in the light-emitting layer was replaced with P-353 from P-4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％P-353(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D11 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were such that yellow light emission (driving voltage of 2.8V) having a wavelength of 560nm, a half-peak width of 39nm, CIE color coordinates (x, y) (0.34,0.60), and an external quantum efficiency EQE of 28.3% was obtained.
Device example 12
The same preparation method as that of device example 1 was used except that the wide band gap type Host material Host in the light-emitting layer was replaced with TADF type Host TD and the dye was replaced with P-353 from P-4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％P-353(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D12 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were such that yellow light emission (drive voltage of 2.4V) having a wavelength of 561nm, a half-peak width of 42nm, CIE color coordinates (x, y) (0.32,0.59), and an external quantum efficiency EQE of 30.4% was obtained.
Device example 13
The same procedure as in device example 1 was conducted except that the dye in the light-emitting layer was replaced with P-398 from P-4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％P-398(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D13 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were such that yellow light emission (driving voltage of 2.8V) with a wavelength of 565nm, a half-peak width of 45nm, CIE color coordinates (x, y) ═ 0.39,0.58, and an external quantum efficiency EQE of 29.6% was obtained.
Device example 14
The same preparation method as that of device example 1 was used except that the Host of the wide band gap type Host material in the light-emitting layer was replaced with TADF type Host TD and the dye was replaced with P-398 from P-4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％P-398(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D14 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were such that yellow light emission (driving voltage of 2.6V) having a wavelength of 566nm, a half-width of 46nm, CIE color coordinates (x, y) ═ 0.39,0.56, and an external quantum efficiency EQE of 31.4% was obtained.
Device example 15
The same procedure as in device example 1 was followed except that the dye in the light-emitting layer was replaced with P-363 from P-4. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％P-363(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D15 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were such that orange-red light emission (driving voltage of 2.8V) with a wavelength of 585nm, a half-peak width of 46nm, CIE color coordinates (x, y) ═ 0.55,0.42, and an external quantum efficiency EQE of 29.6% was obtained.
Device example 16
The same preparation method as that of device example 1 was used except that the wide band gap type Host material Host in the light-emitting layer was replaced with TADF type Host TD and the dye was replaced with P-4 to P-363. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％P-363(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D16 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were such that orange-red light emission (driving voltage of 2.4V) with a wavelength of 586nm, a peak width at half maximum of 47nm, CIE color coordinates (x, y) ═ 0.55,0.40, and external quantum efficiency EQE of 31.3% was obtained.
Comparative device example 1
The same preparation method as that of device example 1 was used except that the compound P-4 of the present invention used in the light-emitting layer was replaced with the compound P1 of the prior art, and the specific device structure was as follows:
ITO/HI(10nm)/HT(40nm)/Host:3wt％P1(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device DD1 prepared in this example are as follows: when a dc voltage was applied and the characteristics at 10cd/m2 light emission were measured, blue light emission (driving voltage of 3.6V) with a wavelength of 459nm, a full width at half maximum of 28nm, CIE color coordinates (x, y) ((0.13, 0.09)) and an external quantum efficiency EQE of 13.5% was obtained.
Comparative device example 2
The same preparation method as that of device example 2 except that the compound P-4 of the present invention used in the light-emitting layer was replaced with the compound P1 in the prior art, and a specific device structure was as follows:
ITO/HI(10nm)/HT(40nm)/TD:3wt％P1(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device DD2 prepared in this example are as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission include a wavelength of 460nm, a half-width of 28nm, and CIE color coordinates (x, y)(0.13,0.09) and an external quantum efficiency EQE of 18.4% (driving voltage of 3.3V).
The structural formulas of the various organic materials used in the above examples are as follows:
specific performance data of the organic electroluminescent devices D1 to D16 and the devices DD1 and DD2 prepared in the above respective device examples are detailed in table 1 below.
Table 1:
the experimental data show that the compound provided by the invention can realize the obvious red shift behavior of the target MR-TADF material while maintaining the large HOMO and LUMO orbital overlap of BN rigid framework by amplifying the conjugated framework of the classical MR-TADF material and introducing more nitrogen atoms or boron atoms. As can be seen from the half-peak width of the electroluminescence spectrum, the embodiment confirms that the material has effective multiple resonance effect, thereby greatly enriching the material system of multiple resonance-thermal activation delayed fluorescence and the range of luminescent color, and having good application prospect.
Although the invention has been described in connection with the embodiments, the invention is not limited to the embodiments described above, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the invention, and the scope of the invention is outlined by the appended claims.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (18)
1. A compound of the general formula (I):
in the formula (I), ring A, ring B, ring C and ring D independently represent any one of monocyclic aromatic ring or fused aromatic ring of C5-C20, monocyclic heterocyclic ring or fused heterocyclic ring of C4-C20;
said Y is1And Y2Each is independently N or B; said X1、X2、X3And X4Are each independently NR1Or BR2；
When Y is1And Y2When all are N, X1、X2、X3And X4Are all BR2；
The R is1The adjacent ring A, ring B, ring C or ring D are respectively and independently connected into a ring or not connected into a ring, and the adjacent ring A, ring B, ring C or ring D are connected into a ring through a single bond;
the R is2The adjacent ring A, ring B, ring C or ring D are respectively and independently connected into a ring or not connected into a ring, and the adjacent ring A, ring B, ring C or ring D are connected into a ring through a single bond;
the R is1、R2Each independently selected from one of the following substituted or unsubstituted groups: monocyclic aryl of C6-C60, fused ring aryl of C6-C60, monocyclic heteroaryl of C5-C60Or a fused ring heteroaryl of C5-C60;
the R isa、Rb、RcAnd RdEach independently represents a single substituent up to the maximum permissible substituents, and each is independently selected from hydrogen, deuterium, or one of the following groups: one of halogen, substituted or unsubstituted C1-C36 chain alkyl, substituted or unsubstituted C3-C36 cycloalkyl, C1-C10 alkoxy, cyano, C6-C30 arylamine, C3-C30 heteroarylamino, substituted or unsubstituted C6-C60 monocyclic aryl, C6-C60 fused ring aryl, C6-C60 aryloxy, C5-C60 monocyclic heteroaryl, C5-C60 fused ring heteroaryl and trimethylsilyl;
when the above R is1、R2When a substituent exists, the substituent is independently selected from any one of deuterium, halogen, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, cyano, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl of C6-C60, fused ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60 and fused ring heteroaryl of C5-C60;
when the above R isa、Rb、RcAnd RdWhen the substituent exists, the substituent is independently selected from any one of halogen, chain alkyl of C1-C30, cyano and monocyclic aryl of C6-C60;
and the compounds of the general formula shown in formula (I) do not include the following compounds:
2. the compound of general formula (I) according to claim 1, wherein ring A, ring B, ring C and ring D each independently represent any one of a monocyclic aromatic ring or a fused aromatic ring of C5-C10, a monocyclic heterocyclic ring or a fused heterocyclic ring of C4-C10.
3. The compound of general formula (I) as claimed in claim 1, wherein ring A, ring B, ring C and ring D are independently selected from any one of benzene ring, naphthalene ring or fluorene ring.
4. A compound of formula (la) according to claim 1, represented by the following formula (1):
in formula (1):
said Y is1And Y2Each is independently N or B; said X1、X2、X3And X4Are each independently NR1Or BR2；
When Y is1And Y2When all are N, X1、X2、X3And X4Are all BR2；
The R is1The adjacent ring A, ring B, ring C or ring D are respectively and independently connected into a ring or not connected into a ring, and the adjacent ring A, ring B, ring C or ring D are connected into a ring through a single bond;
the R is2The adjacent ring A, ring B, ring C or ring D are respectively and independently connected into a ring or not connected into a ring, and the adjacent ring A, ring B, ring C or ring D are connected into a ring through a single bond;
the R isa、Rb、Rc、Rd、R1、R2Are as defined in formula (I).
5. The general formula compound according to claim 4, represented by any one of the following formulae (2) to (4):
in formulae (2) to (4), X1、X2、X3、X4、Ra、Rb、RcAnd RdAre as defined in formula (I).
6. A compound of formula (la) according to claim 4, represented by the following formula (2):
in the formula (2), X1、X2、X3And X4Are each independently NR1，Ra、Rb、RcAnd RdAre as defined in formula (I).
7. A compound of formula (la) according to claim 4, represented by the following formula (3):
in the formula (3), X1、X2Are each independently NR1，X3、X4Are respectively independent and are respectively BR2，Ra、Rb、RcAnd RdAre as defined in formula (I).
8. A compound of formula (la) according to claim 4, represented by the following formula (4):
in the formula (4), X1、X2、X3And X4Are respectively independent and are respectively BR2，Ra、Rb、RcAnd RdAre as defined in formula (I)The same is true.
9. The compound of formula (I), formula (1) to formula (4) as claimed in any one of claims 1 to 8,
the R isa、Rb、RcAnd RdEach independently selected from hydrogen, deuterium or one of the following substituent groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2, 2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, grottoyl, perylenyl, anthrylenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenylenyl, trimeric indenyl, isotridecylinyl, trimeric spiroindenyl, spiromesityl, spiroisotridecylinyl, furanyl, isobenzofuranyl, phenyl, terphenyl, anthryl, terphenyl, pyrenyl, terphenyl, terp, Dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, pyrimidyl, benzopyrimidinyl, quinoxalyl, 1, 5-diazaanthracenyl, 2, 7-diazpyrenyl, 2, 3-diazpyrenyl, 1, 6-diazpyrenyl, 1, 8-diazpyrenyl, 4,5,9, 10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1, 2-diazenyl4-triazolyl, benzotriazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, 9-dimethylpyridinyl, diarylamine, adamantyl, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, azanyl, indolizinyl, 9-dimethylpyridinyl, diarylamine, adamantyl, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, and the like, Methoxy, trimethylsilyl, or a combination of two substituents selected from the above.
10. A compound of the formula (5):
in the formula (5), R is1～R26Each independently selected from one of hydrogen, deuterium or halogen, chain alkyl of C1-C36, cycloalkyl of C3-C36, alkoxy of C1-C10, cyano, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl of C6-C60, fused ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60, fused ring heteroaryl of C5-C60 and trimethylsilyl, and R is R1～R26Wherein adjacent two groups are bonded or not bonded to each other, form a single bond when bonded, or form one of a substituted or unsubstituted C5-C30 five-or six-membered aryl ring, a substituted or unsubstituted C5-C30 five-or six-membered heteroaryl ring together with an adjacent benzene ring when bonded, when R is5And R6When bonded, are linked by a single bond, when R10And R11When bonded, are linked by a single bond, when R13And R14When bonded, are linked by a single bond, when R18And R19When bonded, are linked by a single bond, when R20And R21When bonded, are linked by a single bond, when R25And R26When bonding, the two are connected by a single bond;
z is1Is hydrogen or two Z1Bonding to form a single bond;
z is2Is hydrogen or two Z2The bonds form single bonds.
11. The compound of formula (5) according to claim 10, wherein the two Z are1Bonded to form a single bond, Z2Is hydrogen;
or, two Z2Bonded to form a single bond, Z1Is hydrogen;
or, Z1And Z2Are all hydrogen;
or, two Z1Bonding to form a single bond with two Z2The bonds form single bonds.
12. A compound of the formula (6):
in the formula (6), R is1～R26Each independently selected from one of hydrogen, deuterium or halogen, chain alkyl of C1-C36, cycloalkyl of C3-C36, alkoxy of C1-C10, cyano, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl of C6-C60, fused ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60, fused ring heteroaryl of C5-C60 and trimethylsilyl, and R is R1～R26Wherein adjacent two groups are bonded or not bonded to each other, form a single bond when bonded, or form one of a substituted or unsubstituted C5-C30 five-or six-membered aryl ring, a substituted or unsubstituted C5-C30 five-or six-membered heteroaryl ring together with an adjacent benzene ring when bonded, when R is5And R6When bonded, are linked by a single bond, when R10And R11When bonded, are linked by a single bond, when R13And R14When bonded, are linked by a single bond, when R18And R19When they are bonded with each otherIs connected by a single bond, when R20And R21When bonded, are linked by a single bond, when R25And R26When bonding, the two are connected by a single bond;
z is1Is hydrogen or two Z1Bonding to form a single bond;
z is2Is hydrogen or two Z2The bonds form single bonds.
13. The compound of formula (6) according to claim 12, wherein the two Z are1Bonded to form a single bond, Z2Is hydrogen;
or, two Z2Bonded to form a single bond, Z1Is hydrogen;
or, Z1And Z2Are all hydrogen;
or, two Z1Bonding to form a single bond with two Z2The bonds form single bonds.
14. A compound of the formula (7):
in the formula (7), R is1～R26Each independently selected from one of hydrogen, deuterium or halogen, chain alkyl of C1-C36, cycloalkyl of C3-C36, alkoxy of C1-C10, cyano, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl of C6-C60, fused ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60, fused ring heteroaryl of C5-C60 and trimethylsilyl, and R is R1～R26Wherein adjacent two groups are bonded or not bonded to each other, form a single bond when bonded, or form one of a substituted or unsubstituted C5-C30 five-or six-membered aryl ring, a substituted or unsubstituted C5-C30 five-or six-membered heteroaryl ring together with an adjacent benzene ring when bonded, when R is5And R6When bonded, are linked by a single bond, when R10And R11When bonded, are linked by a single bond, when R13And R14When bonded, are linked by a single bond, when R18And R19When bonded, are linked by a single bond, when R20And R21When bonded, are linked by a single bond, when R25And R26When bonding, the two are connected by a single bond;
z is1Is hydrogen or two Z1Bonding to form a single bond;
z is2Is hydrogen or two Z2The bonds form single bonds.
15. The compound of formula (7) according to claim 14, wherein the two Z's are1Bonded to form a single bond, Z2Is hydrogen;
or, two Z2Bonded to form a single bond, Z1Is hydrogen;
or, Z1And Z2Are all hydrogen;
or, two Z1Bonding to form a single bond with two Z2The bonds form single bonds.
16. A compound of the general formula selected from the compounds of the following specific structures:
17. use of a compound as claimed in any one of claims 1 to 16 as a light-emitting layer material in an organic electroluminescent device.
18. An organic electroluminescent device comprising a first electrode, a second electrode and one or more organic layers interposed between said first and second electrodes, characterized in that said organic layers comprise a light-emitting layer comprising at least one compound according to any one of claims 1 to 16.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010017691.1A CN111153919B (en) | 2020-01-08 | 2020-01-08 | Luminescent material, application thereof and organic electroluminescent device comprising luminescent material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010017691.1A CN111153919B (en) | 2020-01-08 | 2020-01-08 | Luminescent material, application thereof and organic electroluminescent device comprising luminescent material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111153919A CN111153919A (en) | 2020-05-15 |
| CN111153919B true CN111153919B (en) | 2021-02-09 |
Family
ID=70561911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010017691.1A Active CN111153919B (en) | 2020-01-08 | 2020-01-08 | Luminescent material, application thereof and organic electroluminescent device comprising luminescent material |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111153919B (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4204424A1 (en) * | 2020-08-27 | 2023-07-05 | Samsung Display Co., Ltd. | Organic molecules for optoelectronic devices |
| JP7556136B2 (en) | 2020-09-04 | 2024-09-25 | エスエフシー カンパニー リミテッド | Polycyclic aromatic derivative compound and organic light-emitting device using the same |
| CN114315876A (en) * | 2020-09-28 | 2022-04-12 | 江苏三月科技股份有限公司 | Boron-containing organic compound as OLED (organic light emitting diode) doping material and organic light emitting device |
| CN112174992B (en) * | 2020-09-30 | 2023-05-02 | 清华大学 | Luminescent material, application thereof and organic electroluminescent device comprising luminescent material |
| CN114369106B (en) * | 2020-10-14 | 2023-11-28 | 广州华睿光电材料有限公司 | Borazine-containing indene compound and application thereof |
| US20230371375A1 (en) * | 2020-10-20 | 2023-11-16 | Nippon Steel Chemical & Material Co., Ltd. | Light-emitting material, and organic electroluminescent element |
| KR20220063724A (en) * | 2020-11-10 | 2022-05-17 | 에스에프씨 주식회사 | Polycyclic compound and organic light emitting device using the same |
| CN114621269B (en) * | 2020-12-09 | 2024-04-09 | 清华大学 | Condensed ring aromatic compound and application thereof in electroluminescent device |
| CN114621270B (en) * | 2020-12-09 | 2024-04-12 | 清华大学 | Condensed ring aromatic compound and application thereof in electroluminescent device |
| CN113173943A (en) * | 2021-05-10 | 2021-07-27 | 清华大学 | Fused ring compound, application thereof and organic electroluminescent device comprising fused ring compound |
| CN113540371B (en) * | 2021-06-07 | 2022-12-09 | 清华大学 | Organic light-emitting device and display device |
| CN114149458B (en) * | 2021-11-29 | 2023-01-06 | 苏州大学 | B/N organic electroluminescent material and preparation method and application thereof |
| CN114044785A (en) * | 2021-12-01 | 2022-02-15 | 上海八亿时空先进材料有限公司 | Boron-containing compound, organic electroluminescent element and organic electroluminescent material |
| CN115050914A (en) * | 2022-05-17 | 2022-09-13 | 苏州大学 | Orange red or red high-brightness organic electroluminescent device |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150033272A (en) * | 2013-09-24 | 2015-04-01 | 최돈수 | Light-emitting material for organic electroluminescent device, organic electroluminescent device using same, and material for organic electroluminescent device |
| CN109192874B (en) * | 2018-08-31 | 2019-09-10 | 昆山国显光电有限公司 | A kind of organic electroluminescence device and display device |
| CN109411634B (en) * | 2018-08-31 | 2019-12-24 | 昆山国显光电有限公司 | Organic electroluminescent device and display device |
| CN111574543A (en) * | 2019-02-18 | 2020-08-25 | 江苏三月科技股份有限公司 | Organic compound containing boron and application thereof in organic electroluminescent device |
| CN111574544A (en) * | 2019-02-18 | 2020-08-25 | 江苏三月科技股份有限公司 | Organic compound containing boron and application thereof in organic electroluminescent device |
| CN110407858B (en) * | 2019-07-18 | 2020-07-14 | 清华大学 | Novel compound, application thereof and organic electroluminescent device using compound |
-
2020
- 2020-01-08 CN CN202010017691.1A patent/CN111153919B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN111153919A (en) | 2020-05-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111153919B (en) | Luminescent material, application thereof and organic electroluminescent device comprising luminescent material | |
| CN110872316B (en) | Novel compound, application thereof and organic electroluminescent device using compound | |
| CN110407859B (en) | Luminescent material, application thereof and organic electroluminescent device comprising luminescent material | |
| CN110407858B (en) | Novel compound, application thereof and organic electroluminescent device using compound | |
| CN112174992B (en) | Luminescent material, application thereof and organic electroluminescent device comprising luminescent material | |
| CN111333671B (en) | Luminescent material, application thereof and organic electroluminescent device comprising luminescent material | |
| WO2022237668A1 (en) | Fused ring compound, application thereof, and organic electroluminescent device containing same | |
| JP7429055B2 (en) | New compounds and their applications, and organic electroluminescent devices using these compounds | |
| CN115448938A (en) | Luminescent material, application thereof and organic electroluminescent device comprising luminescent material | |
| KR102592657B1 (en) | Electroluminescent materials and devices | |
| CN113402537A (en) | Organic compound and application thereof | |
| CN115197252A (en) | Organic compound and application thereof | |
| CN114920758B (en) | Luminescent material, application thereof and organic electroluminescent device comprising luminescent material | |
| CN110615782A (en) | Organic compound and organic electroluminescent device containing the same | |
| CN112409276A (en) | Compound and application thereof | |
| CN114671872A (en) | Organic electroluminescent compound and application thereof | |
| CN112409241A (en) | Organic compound, application thereof and organic electroluminescent device adopting organic compound | |
| CN113444090A (en) | Compound and application thereof | |
| CN114478267A (en) | Organic compound for light emitting device and organic electroluminescent device | |
| CN111909154A (en) | Organic compound, application thereof and organic electroluminescent device comprising organic compound | |
| CN111763208A (en) | Luminescent material and application thereof | |
| CN112661760B (en) | Compound for organic electronic material and organic electroluminescent device containing the same | |
| CN116478191A (en) | Luminescent material, application thereof and organic electroluminescent device comprising luminescent material | |
| CN115304627A (en) | Polar boron-nitrogen luminescent material, application thereof and organic electroluminescent device comprising same | |
| CN116535430A (en) | Luminescent material, application thereof and organic electroluminescent device comprising luminescent material |
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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |