CN116178404A - Boron-containing organic compound and application thereof - Google Patents
Boron-containing organic compound and application thereof Download PDFInfo
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- CN116178404A CN116178404A CN202111423180.0A CN202111423180A CN116178404A CN 116178404 A CN116178404 A CN 116178404A CN 202111423180 A CN202111423180 A CN 202111423180A CN 116178404 A CN116178404 A CN 116178404A
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- Prior art keywords
- substituted
- unsubstituted
- formula
- heteroaryl
- ring
- Prior art date
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 229910052796 boron Inorganic materials 0.000 title claims abstract description 25
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 81
- 239000000463 material Substances 0.000 claims abstract description 25
- -1 cyano, nitro, hydroxy, amino Chemical group 0.000 claims description 155
- 239000010410 layer Substances 0.000 claims description 88
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 33
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 24
- 125000001769 aryl amino group Chemical group 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000004104 aryloxy group Chemical group 0.000 claims description 21
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 230000005525 hole transport Effects 0.000 claims description 13
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 230000000903 blocking effect Effects 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 8
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000002346 layers by function Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 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 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 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
- 125000001725 pyrenyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 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 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 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 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 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 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 3
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000003554 tetrahydropyrrolyl group Chemical group 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 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
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=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
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 2
- 150000001555 benzenes Chemical group 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=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
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 2
- 239000012964 benzotriazole Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004802 cyanophenyl group Chemical group 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
- 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
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 2
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 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
- 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
- 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
- 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
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 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
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims 1
- 230000005669 field effect Effects 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 claims 1
- 239000011368 organic material Substances 0.000 abstract description 9
- 230000005540 biological transmission Effects 0.000 abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 5
- 239000000969 carrier Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 133
- 238000003786 synthesis reaction Methods 0.000 description 133
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 114
- 239000007787 solid Substances 0.000 description 69
- 239000000543 intermediate Substances 0.000 description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 62
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
- 238000001953 recrystallisation Methods 0.000 description 29
- 239000012043 crude product Substances 0.000 description 28
- 238000004440 column chromatography Methods 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 20
- 150000001793 charged compounds Chemical class 0.000 description 18
- 238000004949 mass spectrometry Methods 0.000 description 18
- 238000000034 method Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000975 dye Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 11
- 229910000024 caesium carbonate Inorganic materials 0.000 description 11
- 238000010992 reflux Methods 0.000 description 8
- 239000000758 substrate Substances 0.000 description 7
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000001046 green dye Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000001044 red dye Substances 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
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000006616 biphenylamine group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
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- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- 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
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 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
- 241000235648 Pichia Species 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 241000720974 Protium Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 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
- 230000002411 adverse Effects 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 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 description 1
- 150000004982 aromatic amines Chemical class 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
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005872 benzooxazolyl group Chemical group 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning 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
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000005238 degreasing Methods 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
- 238000012938 design process Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 239000012761 high-performance material Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 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
- 125000005592 polycycloalkyl group Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 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
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
- C07F5/027—Organoboranes and organoborohydrides
-
- 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
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/104—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with other heteroatoms
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- 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
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Abstract
The invention relates to a boron-containing organic material, belongs to the technical field of organic luminescent materials, and also relates to application of the compound in an organic electroluminescent device. The organic compound of the present invention has a structure represented by the following formula. The compound of the invention has simple preparation, and can improve and balance the organic electroluminescent device after being applied to the organic electroluminescent deviceAnd the transmission of carriers improves the luminous efficiency.
Description
Technical Field
The invention relates to a boron-containing organic material, belongs to the technical field of organic luminescent materials, and also relates to application of the compound in an organic electroluminescent device.
Background
The main way people acquire information is through vision, so that a display device is important in the process of human interaction with information. Organic Light Emitting Diodes (OLEDs) have many advantages of flexibility, self-luminescence, high contrast, large size, low power consumption, etc., and become one of the currently mainstream display devices.
The red dye and the green dye which are three primary colors can theoretically realize 100% internal quantum efficiency due to the fact that the red dye and the green dye generally contain heavy atoms such as Ir, pt and the like, and are high in electroluminescent efficiency and low in power consumption, so that the red dye and the green dye become the main stream of the current commercial display equipment. However, the chromaticity and lifetime of blue phosphorescent materials are not as good as the current commercial display requirements. Currently, blue light devices still employ conventional fluorescent materials to achieve high color purity and long device lifetime.
Recently, researchers of Japanese Takuji Hatakeyama and Junji Kido et al report a series of organic materials DABA-1 (adv. Mater.2016,28,2777-2781J. Mater. Chem. C,2019,7, 3082-3089) based on TADF (Thermally Activated Delayed Fluorescence ) of boron-containing resonance type, boron atoms, nitrogen atoms and phenyl groups of the compounds constitute a rigid polycyclic aromatic skeleton, and thus have high fluorescence quantum yield. Compared with the traditional blue fluorescent dye, the compound has narrower spectrum and high color purity. However, the rigid planar structure also causes the energy level difference between the singlet state and the triplet state to be larger, the transition between the triplet state and the singlet state is slower, the exciton is compounded on the dye to cause serious efficiency roll-off, and the service life of the device is shorter.
In addition, too planar a rigid structure often results in an adverse effect such as broadening of the spectrum and red shifting due to too high doping concentrations.
There is still a great room for improvement in the light emitting performance of the existing organic electroluminescent materials, and there is a need in the industry to develop new luminescent material systems to meet the commercial demands. Boron-containing resonant materials have the advantages of high color purity and high luminous efficiency, and are attracting wide attention in the scientific research and industry. However, the resonant dye is more planar in structural characteristics, so that molecular aggregation is very easy to occur, the color purity is reduced, and the device performance is reduced.
Disclosure of Invention
The present invention has been made to solve the above-mentioned problems occurring in the prior art, and an object of the present invention is to provide a boron-containing organic compound.
The invention provides a boron-containing organic compound, which has a structure shown as a formula (1):
in the formula (1), the ring X, the ring Y and the ring Z are respectively and independently selected from any one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
the substituents in ring X, ring Y and ring Z are each independently selected from at least one of halogen, unsubstituted or R ' substituted C1-C20 straight or branched alkyl, unsubstituted or R ' substituted C3-C20 cycloalkyl, unsubstituted or R ' substituted C1-C20 alkoxy, unsubstituted or R ' substituted C1-C20 alkylsilyl, unsubstituted or R ' substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R ' substituted C6-C30 arylamino, unsubstituted or R ' substituted C3-C30 heteroarylamino, unsubstituted or R ' substituted C6-C30 aryloxy, unsubstituted or R ' substituted C3-C30 heteroaryloxy, unsubstituted or R ' substituted C6-C60 aryl, unsubstituted or R ' substituted C3-C60 heteroaryl;
in the formula (1), ar 1 、Ar 2 Each independently selected from any one of substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; the Ar is as follows 1 、Ar 2 Each independently being unconnected to an adjacent ring structure or connected to form a ring by a chemical bond;
in the formula (1), R a 、R b Representing monosubstituted to maximum permissibleA number of substituents, and R a 、R b Each independently selected from any of hydrogen, halogen, substituted or unsubstituted C1-C36 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C1-C20 alkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; r is R a 、R b Each independently linked to a linked ring structure to form a ring or not, R a 、R b Are connected or not connected;
in the formula (1), ar is 1 、Ar 2 、R a 、R b Wherein each R' is independently selected from one or a combination of at least two of halogen, C1-C36 straight or branched chain alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl;
In the formula (1), G has a structure as shown in the formula (G):
in the formula (G), R c 、R d Each independently selected from one of hydrogen, substituted or unsubstituted C3-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 silyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, and R c 、R d At least one of the substituted or unsubstituted C3-C20 chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
in the formula (G), X 1 -X 6 Each independently selected from CR 1 Or N, the R 1 Any one selected from hydrogen, halogen, substituted or unsubstituted C1-C36 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C1-C20 alkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; adjacent R 1 Are not connected or are connected into a ring;
in the formula (G), E is selected from single bond, CR 2 R 3 、NR 4 O, S or SiR 5 R 6 Any one of, wherein R 2 、R 3 、R 4 、R 5 And R is 6 Each independently selected from any of hydrogen, halogen, substituted or unsubstituted C1-C36 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C1-C20 alkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; r is R 2 、R 3 、R 4 、R 5 And R is 6 Each independently of the other being unconnected to, or passing through, adjacent ring structuresThe chemical bonds are connected into a ring.
The R is c 、R d 、R 1 、R 2 、R 3 、R 4 、R 5 And R is 6 Each of the substituted substituents is independently selected from one or a combination of at least two of halogen, C1-C36 straight or branched chain alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl.
Further, in the general formula (G) of the present invention, preferably, R c 、R d At least one of which is a substituted or unsubstituted C3-C20 chain or branched alkyl, a substituted or unsubstituted C3-C20 cycloalkyl, a substituted or unsubstituted C6-C60 aryl, a substituted or unsubstituted C3-C60 heteroaryl, each of which is independently selected from one or a combination of at least two of halogen, C1-C10 straight or branched alkyl, C3-C10 cycloalkyl, C6-C60 aryl, or C3-C60 heteroaryl;
preferably, R c 、R d Each independently selected from one or two of C3-C20 chain or branched alkyl, C3-C20 cycloalkyl, C6-C60 aryl and C3-C60 heteroaryl.
Still more preferably, R c 、R d At least one of which is selected from a substituted or unsubstituted C6-C60 aryl, a substituted or unsubstituted C3-C60 heteroaryl;
more preferably, R c 、R d Are each a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group.
Still further, in the formula (1) of the present invention, the G is selected from structures shown in any one of the formulas (G-1) to (G-6):
in the formulae (2-1) to (2-6), the X 1 -X 6 、R c 、R d 、R 1 、R 2 、R 3 、R 4 、R 5 And R is 6 Is the same as that in formula (2).
In the present specification, the "substituted or unsubstituted" group may be substituted with one substituent or may be substituted with a plurality of substituents, and when the number of substituents is plural, the substituents may be selected from different substituents, and the same meaning is given when the same expression mode is involved in the present invention, and the selection ranges of the substituents are all shown above and are not repeated.
In the present specification, the expression of Ca to Cb means that the group has a carbon number of a to b, and unless otherwise specified, in general, in the present specification, "each independently" means that the subject has a plurality of subjects, and they may be the same or different from each other.
Heteroatoms in the present specification generally refer to atoms or groups of atoms selected from N, O, S, P, si and Se, preferably N, O, S.
In the present specification, unless otherwise specified, the expression of a chemical element generally includes the concept of isotopes having the same chemical properties, for example, the expression of "hydrogen (H)", and also includes the expression of isotopes having the same chemical properties 1 H (protium or H), 2 The concept of H (deuterium or D); carbon (C) then comprises 12 C、 13 C, etc., and are not described in detail.
In the present specification, examples of halogen include: fluorine, chlorine, bromine, iodine, and the like.
In the present specification, unless otherwise specified, both aryl and heteroaryl include cases of single rings and condensed rings.
In the present specification, the substituted or unsubstituted C6-C60 aryl group includes monocyclic aryl groups and condensed ring aryl groups, preferably C6-C30 aryl groups, and further preferably C6-C20 aryl groups. By monocyclic aryl is meant that the molecule contains at least one phenyl group, and when the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and are linked by a single bond, such as, for example: phenyl, biphenyl, terphenyl, and the like. Specifically, the biphenyl group includes 2-biphenyl group, 3-biphenyl group and 4-biphenyl group A base; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl. Condensed ring aryl refers to a group in which at least two aromatic rings are contained in the molecule, and the aromatic rings are not independent of each other but share two adjacent carbon atoms condensed with each other. Exemplary are as follows: naphthyl, anthryl, phenanthryl, indenyl, fluorenyl, fluoranthryl, triphenylenyl, pyrenyl, perylenyl,
And a radical, a tetracenyl radical, a derivative thereof, and the like. The naphthyl comprises 1-naphthyl or 2-naphthyl; the anthracenyl is selected from 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracenyl is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl. The derivative group of the fluorene is selected from 9, 9-dimethylfluorenyl, 9-diethyl fluorenyl, 9-dipropyl fluorenyl, 9-dibutyl fluorenyl 9, 9-dipentylfluorenyl, 9-dihexylfluorenyl, 9-diphenylfluorenyl, 9-dinaphthylfluorenyl, 9' -spirobifluorene, and benzofluorenyl.
The C3-C60 heteroaryl group mentioned in the present specification includes monocyclic heteroaryl groups and condensed ring heteroaryl groups, preferably C3-C30 heteroaryl groups, further preferably C4-C20 heteroaryl groups, and further preferably C5-C12 heteroaryl groups. Monocyclic heteroaryl means that the molecule contains at least one heteroaryl group, and when the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and are linked by a single bond, and examples of the monocyclic heteroaryl group include: furyl, thienyl, pyrrolyl, pyridyl, and the like. Condensed ring heteroaryl means a group in which at least one aromatic heterocyclic ring and one aromatic ring (aromatic heterocyclic ring or aromatic ring) are contained in a molecule and two adjacent atoms are fused together without being independent of each other. Examples of fused ring heteroaryl groups include: benzofuranyl, benzothienyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, acridinyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazolyl, azacarbazolyl, phenothiazinyl, phenazinyl, 9-phenylcarbazolyl, 9-naphthylcarbazolyl, dibenzocarbazolyl, indolocarbazolyl, and the like.
Examples of the C6-C30 arylamino group mentioned in the present specification include: phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrylamino, biphenylamino, and the like.
Examples of the C3-C30 heteroarylamino group mentioned in the present specification include: pyridylamino, pyrimidinylamino, dibenzofuranylamino and the like.
In the present specification, the C1 to C36 linear or branched alkyl group, preferably C1 to C20 linear or branched alkyl group, more preferably C1 to C16 linear or branched alkyl group, still more preferably C1 to C10 linear or branched alkyl group, exemplarily includes but is not limited to: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, n-heptyl, n-nonyl, n-decyl and the like.
In the present specification, the C3-C20 cycloalkyl group includes a monocycloalkyl group and a multicycloalkyl group; wherein, monocycloalkyl refers to an alkyl group having a single cyclic structure; polycycloalkyl refers to a structure in which two or more cycloalkyl groups are formed by sharing one or more ring carbon atoms; examples of the C3-C20 cycloalkyl group include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, and the like.
In the present specification, the C3 to C20 heterocycloalkyl group, further preferably a C3 to C10 heterocycloalkyl group, i.e., a group in which at least 1 carbon atom in the cycloalkyl group listed above is replaced with a heteroatom (e.g., O, S or N, etc.), illustratively includes but is not limited to: tetrahydropyrrolyl, tetrahydrofuranyl, tetrahydrothienyl, piperidinyl, dioxane, and the like.
In the present specification, examples of the C1-C10 alkoxy group which is preferably substituted or unsubstituted C1-C20 alkoxy group, and which is preferably substituted or unsubstituted C1-C10 alkoxy group, may be given as follows: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like are preferred, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy are more preferred.
In the present specification, the aryloxy group is a monovalent group composed of the above aryl group and oxygen, and the heteroaryloxy group is a monovalent group composed of the above heteroaryl group and oxygen. The C6-C30 arylamino groups illustratively include, but are not limited to: phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrylamino, biphenylamino, and the like. The C3-C30 heteroarylamino groups illustratively include, but are not limited to: pyridylamino, pyrimidinylamino, dibenzofuranylamino and the like.
Still further, in the general formula (1) of the present invention, preferably, the ring Z is a substituted or unsubstituted benzene ring, and the substituted substituent is selected from one of halogen, C1 to C10 linear or branched alkyl, C3 to C10 cycloalkyl, C6 to C60 aryl, or C3 to C60 heteroaryl; more preferably, the ring Z is a benzene ring.
Still further, in the general formula (1) of the present invention, preferably, the rings X, Y each independently have a structure as shown in formula a:
in formula A, the dotted line represents a fused bond of the group;
in the formula A, Y 1 、Y 2 、Y 3 、Y 4 Each independently is CR 7 Or N, the R 7 Each independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C1-C36 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C1-C20 alkylamino, substituted or unsubstituted C6-C30 arylamineAny one of a group, a substituted or unsubstituted C3 to C30 heteroarylamino group, a substituted or unsubstituted C6 to C30 aryloxy group, a substituted or unsubstituted C3 to C30 heteroaryloxy group, a substituted or unsubstituted C6 to C60 aryl group, and a substituted or unsubstituted C3 to C60 heteroaryl group; adjacent R 7 Are not connected or are connected into a ring;
R 7 each of the substituted substituents is independently selected from any one or a combination of at least two of halogen, C1-C36 straight or branched chain alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl.
Preferably, said Y 1 、Y 2 、Y 3 、Y 4 Each independently is CR 7 Said R is 7 The same or different.
Preferably, the ring X and the ring Y have the same structure and the same structure of the formula A, wherein Y 1 、Y 2 、Y 3 、Y 4 Each independently is CR 7 Said R is 7 The same or different.
The boron-containing organic compound of the present invention has a structure represented by the formula (2):
ar in formula (2) 1 、Ar 2 、R a 、R b Both of G and G have the same defined ranges as those in formula (1).
Still further preferably, in the above formula (1) or formula (2), the Ar 1 、Ar 2 Each independently selected from structures represented by formula B:
in formula B, represents the attachment site of the group;
in formula B, Z 1 、Z 2 、Z 3 、Z 4 、Z 5 Each independently is CR 8 Or N, the R 8 Each independently selected from any one or a combination of at least two of hydrogen, halogen, C1-C36 straight or branched chain alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; adjacent R 8 Are not connected or are connected into a ring;
preferably, said Z 1 、Z 2 、Z 3 、Z 4 、Z 5 Each independently is CR 8 Said R is 8 The same or different.
The boron-containing organic compound of the present invention has a structure represented by the formula (3):
in formula (3), the dotted line represents a bond or a bond not, R a 、R b G has the same defined range as in formula (1); r is R a 、R b Each independently linked to a linked ring structure to form a ring or not, R a 、R b Are connected or not connected;
R e 、R f each independently represents a substituent group monosubstituted to a maximum permissible number, R e 、R f Each independently selected from the group consisting of hydrogen, halogen, C1-C36 straight or branched alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, or C3-C60 heteroarylOne or a combination of at least two of the groups.
Further preferably, the R e 、R f Each independently selected from hydrogen or from one of the following groups: halogen, cyano, methyl, trifluoromethyl, methoxy, isopropyl, tert-butyl, trimethylsilyl, dimethylamino, cyclohexyl, 
Wherein represents the attachment site of the group.
Further preferably, the R a 、R b Each independently selected from hydrogen, halogen, cyano or from 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-trifluoroethyl, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthracenyl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, hole, perylenyl, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, terphenyl, trimeric indenyl, isotrimeric indenyl, spirotrimeric indenyl, spiroiso-trimeric indenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, pyrazolyl, indolyl, imidazolyl, benzimidazolyl, naphthyridoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, enozolyl, enoxazolyl, Benzooxazolyl, naphthooxazolyl, anthracenooxazolyl, phenanthroxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 4,5,9, 10-tetraazapyrenyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 4-naphthyridinyl, benzotriazolyl, and the like 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-dimethylacridyl, triarylamino, adamantyl, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, t-butylphenyl, isopropylphenyl, tetrahydropyrrolyl, piperidinyl, methoxy, phenylisopropyl, trimethylsilyl or dimethylamino;
The R is a 、R b Each of the substituents independently selected from any one or a combination of at least two of halogen, hydroxy, mercapto, C1-C12 straight or branched chain alkyl, C3-C12 cycloalkyl, C1-C6 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, C3-C30 heteroaryl.
Still further preferably, the R a 、R b Each independently selected from hydrogen or from one of the following groups: halogen, cyano, methyl, trifluoromethyl, methoxy, isopropyl, tert-butyl, trimethylsilyl, dimethylamino, cyclohexyl,
Wherein represents the attachment site of the group.
The specific reason why the boron-containing organic compound of the present invention is suitably used as a luminescent dye in a luminescent layer in an organic electroluminescent device is not clear, and it is presumed that the reason for the excellent performance of such a compound is probably:
1. the boron atoms contained in the compound structure and the nitrogen atoms in the same ring have resonance effect, and a stronger central rigid structure is formed, so that the stokes shift of molecules is reduced, the series of materials have the characteristic of narrow spectrum emission, and when the compound is applied to an OLED device, the luminous efficiency in the device is improved;
2. In the design process of the compound molecule, a class of heterocyclic substituent groups are introduced into the boron-containing compound, and the specific structural groups are particularly shown in a formula G, so that the hole transmission capacity of the compound molecule is improved, the carrier balance of the compound after being applied to a device is enhanced, and the voltage of the device is reduced;
3. the invention introduces a class of large steric hindrance groups R at the ortho-position of N atoms in heterocyclic substituent groups shown in the formula G in the structure of the compound c 、R d Because of a certain steric hindrance effect in the molecule, when the compound is applied to a device as a luminescent dye, the interaction between dye molecules can be reduced, so that the problems of concentration aggregation and quenching of the dye molecules can be solved, and finally the efficiency roll-off of the organic electroluminescent device can be inhibited, and the efficiency of the device can be improved.
In addition, the preparation process of the compound is simple and easy to implement, raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
As preferable structures of the present invention related compounds, the following specific compounds M1 to M216 may be mentioned, but are not limited to these compounds:
in another aspect of the invention, there is also provided the use of a compound as described above in an organic electroluminescent device. In particular, the use as a material for a light-emitting layer in an organic electroluminescent device is preferred, more preferably as a material in a light-emitting layer in an organic electroluminescent device, and in particular as a luminescent dye can be applied.
As still another aspect of the present invention, there is also provided an organic electroluminescent device 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 contains the compound of formula (1) as described above or the compound of structures M1 to M216 as described above.
Specifically, an embodiment of the present invention provides an organic electroluminescent device including a substrate, and a first electrode, a plurality of light emitting functional layers, and a second electrode sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole transmission layer, a light-emitting layer and an electron transmission layer, wherein the hole injection layer is formed on the anode layer, the hole transmission layer is formed on the hole injection layer, the cathode layer is formed on the electron transmission layer, and the light-emitting layer is arranged between the hole transmission layer and the electron transmission layer; wherein the light-emitting layer contains the compound of the general formula (1) or the compound of the structures M1 to M216.
The invention also discloses a display screen or a display panel, wherein the display screen or the display panel adopts the organic electroluminescent device; preferably, the display screen or display panel is an OLED display.
The invention also discloses electronic equipment, wherein the electronic equipment is provided with a display screen or a display panel, and the display screen or the display panel adopts the organic electroluminescent device.
The OLED device prepared by the compound has low starting voltage and better service life, and can meet the requirements of current panel manufacturing enterprises on high-performance materials.
Detailed Description
Specific methods for preparing the above novel compounds of the present invention will be described below by way of example with reference to a plurality of synthesis examples, but the preparation method of the present invention is not limited to these synthesis examples.
It should be noted that, the method for obtaining the compound is not limited to the synthetic method and raw materials used in the present invention, and those skilled in the art may select other methods or routes to obtain the compound proposed in the present invention. All compounds of the synthesis process not mentioned in the present invention are commercially available starting products or are prepared by these starting products according to known methods.
The solvents and reagents used in the present invention, such as methylene chloride, petroleum ether, ethanol, t-butylbenzene, boron tribromide, carbazole, diphenylamine, etc., may be purchased from domestic chemical product markets, such as from the national pharmaceutical group reagent company, TCI company, shanghai pichia pharmaceutical company, carboline reagent company, etc.
The method for synthesizing the compound of the present invention will be briefly described.
Synthetic examples
Representative synthetic routes are as follows:
specific methods for preparing the above novel compounds of the present invention will be described below by way of example with reference to a plurality of synthesis examples, but the preparation method of the present invention is not limited to these synthesis examples. Analytical detection of intermediates and compounds in the present invention uses an absiex mass spectrometer (4000 QTRAP).
Synthesis example 1
Synthesis of compound M1:
synthesis of intermediate M1-1:
SM1 (13.5 g,46.82 mmol), SM2 (17.95 g,56.18 mmol), cesium carbonate (22.88 g,70.23 mmol), DMF (300 mL) were placed in a 2L three-necked flask, purged with nitrogen 3 times, and heated to 125℃for 3 hours.
The system was cooled to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the filter cake was recrystallized from ethanol to give intermediate M1-1.7 g of a white solid.
Synthesis of intermediate M1-2:
m1-1 (18.0 g,30.63 mmol), SM3 (11.4 g,67.38 mmol), pd132 (1.08 g,1.53 mmol), sodium t-butoxide (11.77 g,122.5 mmol) and toluene (200 mL) were placed in a 500mL three-necked flask, purged with nitrogen 3 times, and the temperature was raised to reflux for 12 hours.
The system is cooled to room temperature, 18.2g of crude product is obtained by column chromatography purification, and intermediate M1-2 17g of white solid is obtained by recrystallization with toluene/isopropanol.
Synthesis of product M1:
intermediate M1-2 (17 g,22.24 mmol) was added to a 500ml three-necked flask, xylene (170 ml) was added, the reaction system was cooled to-60℃and tert-butyllithium (27.8 mL,44.48 mmol) was added dropwise thereto, and stirring was continued for 30 minutes while maintaining a low temperature. Then the temperature is raised to 60 ℃ for reaction for 2 hours. The reaction system temperature was again lowered to-40℃and boron tribromide (11.14 g,44.48 mmol) was added thereto, followed by stirring at room temperature for 20 minutes. The temperature of the system was again lowered to-40℃and diisopropylethylamine (8.62 g,66.72 mmol) was added. Finally, the reaction system is heated to 120 ℃ for reaction for 12 hours.
After the reaction was cooled to room temperature, the organic phase was dried under reduced pressure. Column chromatography gives 7g crude product, toluene/ethanol recrystallization gives 5.2g yellowish green solid with purity of 99.17%. Mass spectrometry determines molecular ion mass: 737.45 (theory: 737.30).
Synthesis example 2
Synthesis of compound M4:
synthesis of intermediate M4-1:
synthesis of M4-1.3 g of white solid was obtained after recrystallization as in the case of M1-1.
Synthesis of intermediate M4-2:
m4-1 (19.5 g,33.18 mmol), SM3 (20.54 g,72.99 mmol), pd132 (1.17 g,1.66 mmol), sodium tert-butoxide (12.75 g,132.71 mmol) and toluene (200 mL) were placed in a 500mL three-necked flask, purged with nitrogen 3 times, and the temperature was raised to reflux for 12 hours.
The system was cooled to room temperature, purified by column chromatography to give crude product 20.1g, and recrystallized from toluene/isopropanol to give intermediate M4-2.2 g as a white solid.
Synthesis of product M4:
intermediate M4-2 (17.5 g,17.7 mmol) was added to a 500ml three-necked flask, xylene (170 ml) was added, nitrogen was substituted 3 times, the reaction system was cooled to-60℃and tert-butyllithium (22.12 mL,35.14 mmol) was added dropwise to the system, and stirring was continued for 30 minutes while maintaining the low temperature. Then the temperature is raised to 60 ℃ for reaction for 2 hours. The reaction system temperature was again lowered to-40℃and boron tribromide (8.87 g,35.14 mmol) was added thereto, followed by stirring at room temperature for 20 minutes. The temperature of the system was again lowered to-40℃and diisopropylethylamine (6.86 g,53.09 mmol) was added. Finally, the reaction system is heated to 120 ℃ for reaction for 12 hours.
After the reaction was cooled to room temperature, the organic phase was dried under reduced pressure. Column chromatography gives 6.7g crude product, toluene/ethanol recrystallization gives 4.6g yellowish green solid with 99.36% purity. Mass spectrometry determines molecular ion mass: 961.39 (theory: 961.55).
Synthesis example 3
Synthesis of compound M11:
synthesis of intermediate M11-1:
synthesis of M11-1 was performed in the same manner as in M1-1, and after recrystallization, 21.5g of a white solid was obtained.
Synthesis of intermediate M11-2:
m11-1 (19.6 g,33.35 mmol), SM3 (20.50 g,73.37 mmol), pd132 (1.18 g,1.67 mmol), sodium tert-butoxide (12.82 g,132.71 mmol) and toluene (200 mL) were placed in a 500mL three-necked flask, purged with nitrogen 3 times, and heated to reflux for 12 hours.
The system was cooled to room temperature, purified by column chromatography to give 17.2g of crude product, and recrystallized from toluene/isopropanol to give intermediate M11-2.6 g of white solid.
Synthesis of product M11:
the synthesis scheme is the same as that of M1, column chromatography is carried out to obtain 5.2g of crude product, toluene/ethanol is recrystallized to obtain 3.3g of yellow-green solid, and the purity is 99.36%. Mass spectrometry determines molecular ion mass: 957.68 (theory: 957.52).
Synthesis example 4
Synthesis of Compound M19:
synthesis of intermediate M19-1:
synthesis of M19-1.6 g of white solid was obtained after recrystallization as in the case of M1-1.
Synthesis of intermediate M19-2:
m19-1 (23.2 g,39.47 mmol), SM3 (12.22 g,43.42 mmol), pd2 (dba) 3 (323 mg,0.79 mmol), P (t-Bu) 3HBF4 (0.57 g,1.97 mmol), sodium t-butoxide (7.59 g,78.95 mmol), toluene (200 mL) were placed in a 500mL three-necked flask, nitrogen was replaced three times, and reacted at 100℃for 12 hours.
The system was cooled to room temperature, purified by column chromatography to give 23.5g of crude product, and recrystallized from toluene/isopropanol to give intermediate M19-2.1 g of white solid.
Synthesis of intermediate M19-3:
m19-2 (21 g,26.64 mmol), SM4 (10.28 g,31.97 mmol), pd132 (0.94 g,1.33 mmol), sodium tert-butoxide (5.12 g,53.28 mmol) and toluene (200 mL) were placed in a 500mL three-necked flask, nitrogen was replaced 3 times, and the temperature was raised to reflux for 12 hours.
The system was cooled to room temperature and purified by column chromatography to give 19.2g of crude product, which was recrystallized from toluene/isopropanol to give intermediate M19-3.3 g of white solid.
Synthesis of product M19:
the synthesis scheme is the same as that of M1, and the chromatography is performed to obtain 6.2g of crude product, and toluene/ethanol recrystallization is performed to obtain 3.5g of yellow-green solid with the purity of 99.46%. Mass spectrometry determines molecular ion mass: 1001.65 (theory: 1001.49).
Synthesis example 5
Synthesis of Compound M20:
synthesis of intermediate M20-1:
synthesis of M20-1.6 g of white solid was obtained after recrystallization as in the case of M1-1.
Synthesis of intermediate M20-2:
m20-1 (24 g,40.83 mmol), SM3 (12.64 g,44.92 mmol), pd2 (dba) 3 (745 mg,0.82 mmol), P (t-Bu) 3HBF4 (0.59 g,2.04 mmol), sodium t-butoxide (7.85 g,81.67 mmol), toluene (200 mL) were placed in a 500mL three-necked flask, nitrogen was replaced three times, and reacted at 100℃for 12 hours.
The system is cooled to room temperature, the crude product is purified by column chromatography to obtain 24g, and toluene/isopropanol is used for recrystallization to obtain an intermediate M20-2 23g white solid.
Synthesis of intermediate M20-3:
synthesis of M19-3 followed by recrystallization gave M20-3.18.1 g of a white solid.
Synthesis of product M20:
the synthesis scheme is the same as that of M1, 7.5g of crude product is obtained by chromatography, 4.2g of yellowish green solid is obtained by toluene/ethanol recrystallization, and the purity is 99.46%. Mass spectrometry determines molecular ion mass: 1001.72 (theory: 1001.49).
Synthesis example 6
Synthesis of compound M27:
synthesis of intermediate M27-1:
synthesis of M27-1.3 g of white solid was obtained after recrystallization as in the case of M1-1.
Synthesis of intermediate M27-2:
synthesis of M27-2.3 g of white solid was obtained after recrystallization as in the case of M20-2.
Synthesis of intermediate M27-3:
synthesis of M27-3.2 g of white solid was obtained after recrystallization as in the case of M11-2.
Synthesis of product M27:
the synthesis scheme is the same as that of M1, and the chromatography is performed to obtain 6.9g of crude product, and toluene/ethanol recrystallization is performed to obtain 3.8g of yellow-green solid with the purity of 99.34%. Mass spectrometry determines molecular ion mass: 959.32 (theory: 959.53).
Synthesis example 7
Synthesis of compound M32:
synthesis of intermediate M32-1:
SM1 (13 g,45 mmol), SM2 (23.35 g,54.10 mmol), cesium carbonate (22.03 g,67.63 mmol), DMF (300 mL) were placed in a 2L three-necked flask, nitrogen was replaced 3 times, and the temperature was raised to 125℃for 3 hours.
The system was cooled to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the cake was recrystallized from ethanol to give intermediate M32-123.2g of a white solid.
Synthesis of intermediate M32-2:
synthesis of M32-2.3 g of white solid was obtained after recrystallization as in the case of M4-2.
Synthesis of product M32:
the synthesis scheme is the same as that of M1, 7.3g of crude product is obtained by chromatography, 5.1g of yellowish green solid is obtained by toluene/ethanol recrystallization, and the purity is 99.52%. Mass spectrometry determines molecular ion mass: 1073.48 (theory: 1073.68).
Synthesis example 8
Synthesis of Compound M56:
synthesis of intermediate M56-1:
SM1 (14 g,48.55 mmol), SM2 (16.28 g,58.26 mmol), cesium carbonate (23.73 g,72.83 mmol) and DMF (300 mL) were placed in a 2L three-necked flask, purged with nitrogen 3 times, and heated to 125℃for 3 hours.
The system was cooled to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the cake was recrystallized from ethanol to give intermediate M56-118.7g of a white solid.
Synthesis of intermediate M56-2:
synthesis of M56-2 15.7g of white solid was obtained after recrystallization as in the case of M4-2.
Synthesis of product M56:
the synthesis scheme is the same as that of M1, column chromatography is carried out to obtain 5.6g of crude product, toluene/ethanol is recrystallized to obtain 3.2g of yellow-green solid, and the purity is 99.48%. Mass spectrometry determines molecular ion mass: 921.23 (theory: 921.61).
Synthesis example 9
Synthesis of compound M91:
synthesis of intermediate M91-1:
SM1 (14.5 g,50.29 mmol), SM2 (20 g,60.35 mmol), cesium carbonate (24.58 g,75.43 mmol), DMF (300 mL) were placed in a 2L three-necked flask, purged with nitrogen 3 times, and heated to 125℃for 3 hours.
The system was cooled to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the cake was recrystallized from ethanol to give intermediate M91-118.9g of a white solid.
Synthesis of intermediate M91-2:
m91-1 (18.5 g,30.84 mmol), SM3 (27.52 g,67.85 mmol), pd132 (1.09 g,1.54 mmol), sodium tert-butoxide (11.86 g,123.37 mmol) and toluene (200 mL) were placed in a 500mL three-necked flask, purged with nitrogen 3 times, and the temperature was raised to reflux for 12 hours.
The system was cooled to room temperature, purified by column chromatography to give 22.3g of crude product, and recrystallized from toluene/isopropanol to give intermediate M91-2.2 g of white solid.
Synthesis of product M91:
the synthesis scheme is the same as that of M1, column chromatography is carried out to obtain 4.8g of crude product, toluene/ethanol is recrystallized to obtain 3.9g of yellow-green solid, and the purity is 99.62%. Mass spectrometry determines molecular ion mass: 1221.56 (theory: 1221.71).
Synthesis example 10
Synthesis of Compound M116:
synthesis of intermediate M116-1:
SM1 (14.8 g,51.33 mmol), SM2 (29.05 g,61.59 mmol), cesium carbonate (25.09 g,76.99 mmol), DMF (300 mL) were put into a 2L three-necked flask, purged with nitrogen 3 times, and heated to 125℃for 3 hours.
The system is cooled to room temperature, water (500 ml) is added dropwise into the system to precipitate solid, the solid is filtered, and the filter cake is recrystallized by ethanol to obtain intermediate M116-122.3g of white solid.
Synthesis of intermediate M116-2:
synthesis of M116-2.3 g of a white solid was obtained after recrystallization as in the case of M4-2.
Synthesis of product M116:
the synthesis scheme is the same as that of M1, column chromatography is carried out to obtain 5.6g of crude product, toluene/ethanol is recrystallized to obtain 4.3g of yellow-green solid, and the purity is 99.33%. Mass spectrometry determines molecular ion mass: 1113.83 (theory: 1113.61).
Synthesis example 11
Synthesis of Compound M140:
synthesis of intermediate M140-1:
SM1 (15.5 g,53.76 mmol), SM2 (15.7 g,64.51 mmol), cesium carbonate (26.27 g,80.63 mmol), DMF (300 mL) were placed in a 2L three-necked flask, purged with nitrogen 3 times, and heated to 125℃for 3 hours.
The system was cooled to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the cake was recrystallized from ethanol to give intermediate M140-119.6g of a white solid.
Synthesis of intermediate M140-2:
synthesis of M140-2 and recrystallization gave M4-2.3 g of a white solid.
Synthesis of product M140:
the synthesis scheme is the same as that of M1, column chromatography is carried out to obtain 4.3g of crude product, toluene/ethanol is recrystallized to obtain 3.2g of yellow-green solid, and the purity is 99.43%. Mass spectrometry determines molecular ion mass: 885.36 (theory: 885.52).
Synthesis example 12
Synthesis of Compound M144:
synthesis of intermediate M144-1:
synthesis of M144-1.6 g of a white solid was obtained after recrystallization as in the case of M140-1.
Synthesis of intermediate M144-2:
m144-1 (18.5 g,36.16 mmol), SM3 (13.3 g,79.55 mmol), pd132 (1.25 g,1.81 mmol), sodium tert-butoxide (13.9 g,144.63 mmol) and toluene (200 mL) were placed in a 500mL three-necked flask, purged with nitrogen 3 times, and the temperature was raised to reflux for 12 hours.
The system was cooled to room temperature, purified by column chromatography to give 16.8g of crude product, and recrystallized from toluene/isopropanol to give intermediate M144-2.3 g of white solid.
Synthesis of product M144:
the synthesis scheme is the same as that of M1, column chromatography is carried out to obtain 4.6g of crude product, toluene/ethanol is recrystallized to obtain 3.6g of yellow-green solid, and the purity is 99.13%. Mass spectrometry determines molecular ion mass: 657.36 (theory: 657.24).
Synthesis example 13
Synthesis of Compound M147:
synthesis of intermediate M147-1:
synthesis of M147-1 and M140-1 gave, after recrystallization, 22.5g of a white solid.
Synthesis of intermediate M147-2:
m147-1 (19 g,37.14 mmol), SM3 (22.83 g,81.70 mmol), pd132 (1.31 g,1.86 mmol), sodium tert-butoxide (14.28 g,148.54 mmol) and toluene (200 mL) were placed in a 500mL three-necked flask, nitrogen was replaced 3 times, and the temperature was raised to reflux for 12 hours.
The system was cooled to room temperature, purified by column chromatography to give 22.6g of crude product, and recrystallized from toluene/isopropanol to give intermediate M147-2.3 g of white solid.
Synthesis of product M147:
the synthesis scheme is the same as that of M1, column chromatography is carried out to obtain 5.9g of crude product, toluene/ethanol is recrystallized to obtain 4.2g of yellow-green solid, and the purity is 99.23%. Mass spectrometry determines molecular ion mass: 881.65 (theory: 881.49).
Synthesis example 14
Synthesis of Compound M169:
synthesis of intermediate M169-1:
SM1 (18 g,62.43 mmol), SM2 (21.38 g,74.91 mmol), cesium carbonate (30.51 g,93.64 mmol), DMF (300 mL) were placed in a 2L three-necked flask, purged with nitrogen 3 times, and heated to 125℃for 3 hours.
The system was cooled to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the cake was recrystallized from ethanol to give intermediate M169-1.6 g of a white solid.
Synthesis of intermediate M169-2:
synthesis of M169-2 was repeated as illustrated in the previous example to obtain 20.9g of a white solid.
Synthesis of product M169:
the synthesis scheme is the same as that of M1, column chromatography is carried out to obtain 6.2g of crude product, toluene/ethanol recrystallization is carried out to obtain 4.9g of yellow-green solid, and the purity is 99.13%. Mass spectrometry determines molecular ion mass: 703.56 (theory: 703.32).
Synthesis example 15
Synthesis of compound M173:
synthesis of intermediate M173-1:
SM1 (20 g,69.36 mmol), SM2 (24.92 g,83.24 mmol), cesium carbonate (33.9 g,104.04 mmol) and DMF (300 mL) were put into a 2L three-necked flask, nitrogen was replaced 3 times, and the temperature was raised to 125℃for 3 hours.
The system was cooled to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the cake was recrystallized from ethanol to give intermediate M173-1.6 g of a white solid.
Synthesis of intermediate M173-2:
synthesis of M173-2 and recrystallization gave M173-2.6 g of a white solid.
Synthesis of product M173:
the synthesis scheme is the same as that of M1, and the chromatography is carried out to obtain 5.8g of crude product, and toluene/ethanol recrystallization is carried out to obtain 4.3g of yellow-green solid with the purity of 99.45%. Mass spectrometry determines molecular ion mass: 717.65 (theory: 717.33).
Synthesis example 16
Synthesis of Compound M176:
synthesis of intermediate M176-1:
SM1 (19.6 g,67.98 mmol), SM2 (23.28 g,81.57 mmol), cesium carbonate (33.22 g,101.96 mmol), DMF (300 mL) were placed in a 2L three-necked flask, purged with nitrogen 3 times, and heated to 125℃for 3 hours.
The system was cooled to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the cake was recrystallized from ethanol to give intermediate M176-1.2 g of a white solid.
Synthesis of intermediate M176-2:
synthesis of M176-2 and recrystallization gave M4-2.3 g of a white solid.
Synthesis of product M176:
the synthesis scheme is the same as that of M1, column chromatography is carried out to obtain 5.6g of crude product, toluene/ethanol recrystallization is carried out to obtain 4.3g of yellow-green solid, and the purity is 99.45%. Mass spectrometry determines molecular ion mass: 927.68 (theory: 927.57).
Synthesis example 17
Synthesis of Compound M197:
synthesis of intermediate M197-1:
SM1 (18.5 g,64.16 mmol), SM2 (18.81 g,76.99 mmol), cesium carbonate (31.36 g,96.24 mmol), DMF (300 mL) were put into a 2L three-necked flask, purged with nitrogen 3 times, and heated to 125℃for 3 hours.
The system was cooled to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the filter cake was recrystallized from ethanol to give intermediate M197-1.3 g as a white solid.
Synthesis of intermediate M197-2:
synthesis of M197-2 gave, after recrystallization, 21.0g of a white solid as in the case of M1-2.
Synthesis of product M197:
the synthesis scheme is the same as that of M1, column chromatography is carried out to obtain 5.2g of crude product, toluene/ethanol is recrystallized to obtain 3.9g of yellow-green solid, and the purity is 99.33%. Mass spectrometry determines molecular ion mass: 662.37 (theory: 662.26).
Synthesis example 18
Synthesis of Compound M210:
synthesis of intermediate M210-1:
SM1 (19.5 g,67.63 mmol), SM2 (28.2 g,81.15 mmol), cesium carbonate (33.05 g,101.44 mmol), DMF (300 mL) were placed in a 2L three-necked flask, purged with nitrogen 3 times, and heated to 125℃for 3 hours.
The system was cooled to room temperature, water (500 ml) was added dropwise to the system to precipitate a solid, which was filtered, and the cake was recrystallized from ethanol to give intermediate M210-1.3 g of a white solid.
Synthesis of intermediate M210-2:
m210-1 (22.5 g,36.54 mmol), SM3 (26.81 g,80.38 mmol), pd132 (1.29 g,1.83 mmol), sodium tert-butoxide (14.05 g,146.14 mmol) and toluene (200 mL) were placed in a 500mL three-necked flask, purged with nitrogen 3 times, and heated to reflux for 12 hours.
The system was cooled to room temperature, purified by column chromatography to give 26.3g of crude product, and recrystallized from toluene/isopropanol to give intermediate M210-2.2 g of white solid.
Synthesis of product M210:
the synthesis scheme is the same as that of M1, column chromatography is carried out to obtain 6.8g of crude product, toluene/ethanol recrystallization is carried out to obtain 5.1g of yellow-green solid, and the purity is 99.63%. Mass spectrometry determines molecular ion mass: 1093.53 (theory: 1093.70).
Device embodiment
The OLED prepared by the invention comprises a first electrode, a second electrode and an organic material layer positioned between the electrodes. The organic material may in turn 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.
In particular embodiments, a substrate may be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. A Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material serving as the first electrode on the substrate. When the first electrode is used as the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), zinc oxide (ZnO), or the like, and any combination thereof may be used. When the first electrode is used as the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combinations thereof may be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the organic material layer may be small organic molecules, large organic molecules and polymers, and combinations 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 hole transport layer containing only one compound and a single layer hole transport layer containing a plurality of compounds. The hole transport region may have a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL); wherein the HIL is located between the anode and the HTL and the EBL is located between the HTL and the light emitting layer.
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant-containing polymers such as polystyrene, 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 such as the compounds shown below HT-1 to HT-51; or any combination thereof.
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more of the compounds HT-1 through HT-51 described above, or one or more of the compounds HI-1-HI-3 described below; one or more compounds from HT-1 to HT-51 may also be used to dope one or more of HI-1-HI-3 described below.
The luminescent layer comprises luminescent dyes (i.e. dopants) that can emit different wavelength spectra, and may also comprise Host materials (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 plurality of monochromatic light emitting layers with different colors can be arranged in a plane according to the pixel pattern, or can be stacked together 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 simultaneously emitting different colors such as red, green, and blue.
According to different technologies, the luminescent layer material can be made of different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescence luminescent material and the like. In an OLED device, a single light emitting technology may be used, or a combination of different light emitting technologies may be used. The different luminescent materials classified by the technology can emit light of the same color, and can also emit light of different colors.
In the organic electroluminescent device provided in one aspect of the present invention, the luminescent layer adopts a fluorescent electroluminescence technique. The luminescent dye in the luminescent layer using the boron-containing organic compound of the present invention, the fluorescent host material in the luminescent layer may be selected from, but is not limited to, one or more combinations of BFH-1 through BFH-17 listed below.
In one aspect of the invention, the barrier layer surrounding the light emitting layer may be selected from, but is not limited to, one or more combinations of PH-1 to PH-85.
In one aspect of the invention, an Electron Blocking Layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may employ, but is not limited to, one or more compounds of HT-1 through HT-51 described above, or one or more compounds of PH-47 through PH-77 described above; mixtures of one or more compounds of HT-1 through HT-51 and one or more compounds of PH-47 through PH-77 may also be employed, but are not limited thereto.
The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. 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).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, combinations of one or more of ET-1 through ET-73 listed below.
In one aspect of the invention, a Hole Blocking Layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may employ, but is not limited to, one or more of the compounds ET-1 to ET-73 described above, or one or more of the compounds PH-1 to PH-46; mixtures of one or more compounds of ET-1 to ET-73 with one or more compounds of PH-1 to PH-46 may also be employed, but are not limited to.
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following.
LiQ,LiF,NaCl,CsF,Li 2 O,Cs 2 CO 3 ,BaO,Na,Li,Ca，Yb、Mg。
Device example 1
The preparation process of the organic electroluminescent device in this embodiment is as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam;
placing the glass substrate with anode in vacuum chamber, vacuumizing to<1×10 -5 Pa, vacuum thermal evaporation is carried out on the anode layer film in sequence, wherein 10nm of HT-4:HI-3 (97/3,w/w) mixture is used as a hole injection layer, 60nm of compound HT-4 is used as a hole transport layer, and 5nm of compound HT-14 is used as an electron blocking layer; a binary mixture of 20nm compound BFH-4:M1 (100:3, w/w) as the light-emitting layer, wherein the doping concentration of the compound M1 of the invention is 3wt%;5nm ET-23 as hole blocking layer, 25nm compound ET-69:ET-57 (50/50, w/w) mixture as electron transport layer, 1nm LiF as electron injection layer, 150nm metallic aluminum as cathode. The total evaporation rate of all organic layers and LiF was controlled at 0.1 nm/sec, and the evaporation rate of the metal electrode was controlled at 1 nm/sec.
Device examples 2 to 26 were fabricated in the same manner as in device example 1, except that the dye in the light-emitting layer was replaced with another representative compound of the present invention in the following table 1 from the compound M1 of the present invention, and the doping concentration of the dye in the light-emitting layer was as detailed in table 1.
Device comparative examples 1 to 9 were produced in the same manner as in device example 1 except that the luminescent dye in the light-emitting layer was replaced with the compounds Ref-1, ref-2, ref-3, ref-4, ref-5 and Ref-6 of the prior art described in Table 1 below, respectively, from the compound M1 of the present invention, and the structural formulae of these 6 compounds were as follows:
wherein Ref-1 and Ref-5 refer to CN112679310A synthesis; the method for obtaining Ref-2 refers to the method in the prior art WO2021014001A1, and is not described here again; ref-3 refers to the method described in WO2021187507A1 and is not described in detail herein; ref-4 and Ref-6 refer to the methods in WO2021014001A1 and CN110719914A, respectively, and are not described in detail herein.
The testing method of the device comprises the following steps:
the organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
the driving voltage and current efficiency and the lifetime of the devices of the organic electroluminescent devices prepared in examples 1 to 26 and comparative examples 1 to 9 were measured using a digital source meter and PR650 at the same brightness. Specifically, the luminance of the organic electroluminescent device was measured to reach 1000cd/m by increasing the voltage at a rate of 0.1V per second 2 The voltage at the time is the driving voltage under the corresponding brightness, and meanwhile, the external quantum efficiency (EQE%) of the device can be obtained through direct test on PR 650;
The comparative performance of the organic electroluminescent devices prepared in the device examples 2 to 26 and the device comparative examples 1 to 9 are shown in Table 1 below.
Table 1:
as can be seen from the data in Table 1, the organic electroluminescent devices prepared in device examples 1 to 26 can effectively reduce the driving voltage of the device, and at the same time, the device exhibits better efficiency performance with less variation in device performance with the doping concentration of dye, compared with the devices prepared in comparative examples 1 to 9.
The present invention is described in detail by the above examples, but the present invention is not limited to the above detailed methods, i.e., it does not mean that the present invention must be practiced depending on the above detailed methods. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.
Claims (14)
1. A boron-containing organic compound having a structure represented by the formula (1):
in the formula (1), the ring X, the ring Y and the ring Z are respectively and independently selected from any one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
The substituents in ring X, ring Y and ring Z are each independently selected from at least one of halogen, unsubstituted or R ' substituted C1-C20 straight or branched alkyl, unsubstituted or R ' substituted C3-C20 cycloalkyl, unsubstituted or R ' substituted C1-C20 alkoxy, unsubstituted or R ' substituted C1-C20 alkylsilyl, unsubstituted or R ' substituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, unsubstituted or R ' substituted C6-C30 arylamino, unsubstituted or R ' substituted C3-C30 heteroarylamino, unsubstituted or R ' substituted C6-C30 aryloxy, unsubstituted or R ' substituted C3-C30 heteroaryloxy, unsubstituted or R ' substituted C6-C60 aryl, unsubstituted or R ' substituted C3-C60 heteroaryl;
in the formula (1), ar 1 、Ar 2 Each independently selected from any one of substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; the Ar is as follows 1 、Ar 2 Each independently being unconnected to an adjacent ring structure or connected to form a ring by a chemical bond;
in the formula (1), R a 、R b Represents a substituent of up to a maximum allowable number of monosubstituted groups, and R a 、R b Each independently selected from any of hydrogen, halogen, substituted or unsubstituted C1-C36 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C1-C20 alkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; r is R a 、R b Each independently linked to a linked ring structure to form a ring or not, R a 、R b Are connected or not connected;
in the formula (1), ar is 1 、Ar 2 、R a 、R b Wherein each R' is independently selected from one or a combination of at least two of halogen, C1-C36 straight or branched chain alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl;
in the formula (1), G has a structure as shown in the formula (G):
in the formula (G), R c 、R d Each independently selected from hydrogen, substituted or unsubstituted C3-C20 straight or branched alkyl, substituted or unsubstituted C3-C20 ringAlkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 silyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, and R c 、R d At least one of the substituted or unsubstituted C3-C20 chain or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
In the formula (G), X 1 -X 6 Each independently selected from CR 1 Or N, the R 1 Any one selected from hydrogen, halogen, substituted or unsubstituted C1-C36 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C1-C20 alkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; adjacent R 1 Are not connected or are connected into a ring;
in the formula (G), E is selected from single bond, CR 2 R 3 、NR 4 O, S or SiR 5 R 6 Any one of, wherein R 2 、R 3 、R 4 、R 5 And R is 6 Each independently selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C1-C36 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkyl, substituted or unsubstituted C1-C10 alkoxy, carboxy, nitro, cyano, amino, hydroxy, mercapto, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C1-C20 alkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl Any one of substituted or unsubstituted C3 to C60 heteroaryl; r is R 2 、R 3 、R 4 、R 5 And R is 6 Each independently being unconnected to an adjacent ring structure or connected to form a ring by a chemical bond;
the R is c 、R d 、R 1 、R 2 、R 3 、R 4 、R 5 And R is 6 Each of the substituted substituents is independently selected from one or a combination of at least two of halogen, C1-C36 straight or branched chain alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl.
2. The boron-containing organic compound according to claim 1, wherein the ring Z is a substituted or unsubstituted benzene ring, and the substituted substituent is selected from one of halogen, C1-C10 linear or branched alkyl, C3-C10 cycloalkyl, C6-C60 aryl, or C3-C60 heteroaryl;
preferably, the ring Z is a benzene ring.
3. The boron-containing organic compound according to claim 1 or 2, wherein the rings X, Y each independently have a structure as shown in formula a:
in formula A, the dotted line represents a fused bond of the group;
In the formula A, Y 1 、Y 2 、Y 3 、Y 4 Each independently is CR 7 Or N, the R 7 Each independently selected from hydrogen, halogen, substituted or unsubstituted C1-C36 straight or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 heterocycloalkylAny one of substituted or unsubstituted C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C1-C20 alkylamino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; adjacent R 7 Are not connected or are connected into a ring;
R 7 each of the substituted substituents is independently selected from any one or a combination of at least two of halogen, C1-C36 straight or branched chain alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl.
4. A boron-containing organic compound according to claim 3, wherein Y 1 、Y 2 、Y 3 、Y 4 Each independently is CR 7 The R is 7 The same or different;
or the ring X and the ring Y have the same structure and are the same structure of a formula A, wherein Y in the formula A 1 、Y 2 、Y 3 、Y 4 Each independently is CR 7 The R is 7 The same or different.
5. The boron-containing organic compound according to claim 1, having a structure represented by formula (2):
ar in formula (2) 1 、Ar 2 、R a 、R b G has the formula(1) The same defined ranges in (a).
6. The boron-containing organic compound according to claim 1 or 5, wherein the Ar 1 、Ar 2 Each independently selected from structures represented by formula B:
in formula B, represents the attachment site of the group;
in formula B, Z 1 、Z 2 、Z 3 、Z 4 、Z 5 Each independently is CR 8 Or N, the R 8 Each independently selected from any one or a combination of at least two of hydrogen, halogen, C1-C36 straight or branched chain alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; adjacent R 8 Are not connected or are connected into a ring;
preferably, said Z 1 、Z 2 、Z 3 、Z 4 、Z 5 Each independently is CR 8 The R is 8 The same or different.
7. The boron-containing organic compound according to claim 1, having a structure represented by formula (3):
in formula (3), the dotted line represents a bond or a bond not, R a 、R b G has the same defined range as in formula (1); r is R a 、R b Each independently connected to a connected ring structure in a ring or notForming a ring, R a 、R b Are connected or not connected;
R e 、R f each independently represents a substituent group monosubstituted to a maximum permissible number, R e 、R f Each independently selected from one or a combination of at least two of hydrogen, halogen, C1-C36 straight or branched chain alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl.
8. The boron-containing organic compound according to claim 7, wherein said R e 、R f Each independently selected from hydrogen or one of the following groups: halogen, cyano, methyl, trifluoromethyl, methoxy, isopropyl, tert-butyl, trimethylsilyl, dimethylamino, cyclohexyl, 
Wherein represents the attachment site of the group.
9. The boron-containing organic compound according to claim 7, wherein said R a 、R b Each independently selected from hydrogen, halogen, cyano or from 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-trifluoroethyl, phenyl, naphthyl, fluorenyl, spirobifluorenyl, anthracenyl, benzanthrenyl, phenanthryl, benzophenanthryl, pyrenyl, grottoyl, peryleneAlkenyl, fluororenyl, naphthacene, pentacenyl, benzopyrene, biphenyl, terphenyl, trimeric indenyl, heterotrimeric indenyl, spirotetraindenyl, spiroheterotrimeric indenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridinyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, pyrazolyl, indolyl, imidazolyl, benzimidazolyl, naphthizolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, benzoxazolyl, naphthyridoizolyl, phenanthroimidazolyl anthracenyl, phenanthrenyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 4,5,9, 10-tetrazolyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazolyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 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-triazinyl, 1,2, 3-triazinyl, 1, 4-tetrazolyl, 1,2, 3-tetrazolyl, 4-tetrazolyl 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, 9-dimethylacridyl, triarylamino, adamantyl, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, t-butylphenyl, isopropylphenyl, tetrahydropyrrolyl, piperidinyl, methoxy, phenylisopropyl, trimethylsilyl or dimethylamino;
The R is a 、R b Each of the substituents independently selected from any one of halogen, hydroxy, mercapto, C1-C12 straight or branched alkyl, C3-C12 cycloalkyl, C1-C6 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, C3-C30 heteroaryl, or at leastA combination of the two;
preferably, said R a 、R b Each independently selected from hydrogen or from one of the following groups: halogen, cyano, methyl, trifluoromethyl, methoxy, isopropyl, tert-butyl, trimethylsilyl, dimethylamino, cyclohexyl,
Wherein represents the attachment site of the group.
10. The boron-containing organic compound according to any one of claims 1, 5 or 7, wherein in the formula (G), R c 、R d At least one of which is a substituted or unsubstituted C3-C20 linear or branched alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, each of which is independently selected from one or a combination of at least two of halogen, C1-C10 linear or branched alkyl group, C3-C10 cycloalkyl group, C6-C60 aryl group, or C3-C60 heteroaryl group;
preferably, R c 、R d Each independently selected from one or two of C3-C20 chain or branched alkyl, C3-C20 cycloalkyl, C6-C60 aryl and C3-C60 heteroaryl.
Still more preferably, R c 、R d At least one of which is selected from a substituted or unsubstituted C6-C60 aryl, a substituted or unsubstituted C3-C60 heteroaryl;
more preferably, R c 、R d Are each a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group.
11. The boron-containing organic compound according to any one of claims 1, 5 or 7, wherein G is selected from the structures shown in any one of formulae (G-1) to (G-6):
in the formulae (2-1) to (2-6), the X 1 -X 6 、R c 、R d 、R 1 、R 2 、R 3 、R 4 、R 5 And R is 6 Is the same as that in formula (2).
12. The boron-containing organic compound according to claim 1, wherein the compound has the structure shown below:
13. use of a compound of the general formula according to any one of claims 1 to 12 as a functional material in an organic electronic device comprising an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet scanner or an electronic paper;
Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device, more preferably as a light-emitting dye in a light-emitting layer.
14. An organic electroluminescent device comprising a first electrode, a second electrode, and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layers contain the organic compound according to any one of claims 1 to 12;
preferably, the light-emitting functional layer comprises an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, and the light-emitting layer contains the organic compound according to any one of claims 1 to 12.
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