CN116253753A - Luminescent material, application thereof and organic electroluminescent device comprising luminescent material - Google Patents
Luminescent material, application thereof and organic electroluminescent device comprising luminescent material Download PDFInfo
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- CN116253753A CN116253753A CN202211658110.8A CN202211658110A CN116253753A CN 116253753 A CN116253753 A CN 116253753A CN 202211658110 A CN202211658110 A CN 202211658110A CN 116253753 A CN116253753 A CN 116253753A
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- 239000000463 material Substances 0.000 title claims abstract description 46
- 150000001875 compounds Chemical class 0.000 claims abstract description 351
- 239000010410 layer Substances 0.000 claims description 311
- -1 cyano, nitro, hydroxy, amino Chemical group 0.000 claims description 192
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 235000010290 biphenyl Nutrition 0.000 claims description 21
- 239000004305 biphenyl Substances 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 15
- 229910052805 deuterium Inorganic materials 0.000 claims description 15
- 125000001769 aryl amino group Chemical group 0.000 claims description 14
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 14
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004104 aryloxy group Chemical group 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 10
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 8
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 7
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 7
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000005561 phenanthryl group Chemical group 0.000 claims description 7
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 6
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims description 5
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical class C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
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- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
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- 238000005286 illumination Methods 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 239000002346 layers by function Substances 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 5
- 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 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 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 5
- 125000001725 pyrenyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 4
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 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 4
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 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 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N Dibenzofuran Natural products C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 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
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 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
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 2
- 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
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 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
- 150000004826 dibenzofurans Chemical class 0.000 claims description 2
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical class C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 claims description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 2
- 230000003287 optical effect Effects 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
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 2
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- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 2
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- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 claims description 2
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- 229910052710 silicon Inorganic materials 0.000 claims 2
- 239000010703 silicon Substances 0.000 claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- HQDYNFWTFJFEPR-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrene Chemical compound C1=C2CCCC(C=C3)C2=C2C3=CC=CC2=C1 HQDYNFWTFJFEPR-UHFFFAOYSA-N 0.000 claims 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
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- 238000002360 preparation method Methods 0.000 description 136
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- 238000006243 chemical reaction Methods 0.000 description 65
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- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
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- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical group C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
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- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
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- 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
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- KATIRQRAVXTBNY-UHFFFAOYSA-N quinolin-4-ylboronic acid Chemical group C1=CC=C2C(B(O)O)=CC=NC2=C1 KATIRQRAVXTBNY-UHFFFAOYSA-N 0.000 description 1
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- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 description 1
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- 229910052722 tritium Inorganic materials 0.000 description 1
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- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
- C09K2211/107—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with other heteroatoms
-
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Abstract
The invention relates to an organic compound, which has a structure shown in the following formula, belongs to the technical field of organic luminescent materials, and also relates to application of the compound in an organic electroluminescent device. When the compound provided by the invention is used as a luminescent material in an OLED device, the compound shows excellent device performance and stability, and a green OLED device with high efficiency, low roll-off and high color purity can be realized. The invention also protects an organic electroluminescent device adopting the compound of the general formula.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a novel thick and doped boron-nitrogen organic compound and application thereof, and an organic electroluminescent device containing the compound.
Background
An organic electroluminescent device (OLED: organic Light Emitting Diodes) is a device with a sandwich-like structure, comprising positive and negative electrode layers and an organic functional material layer sandwiched between the electrode layers. And applying voltage to the electrode of the OLED device, injecting positive charges from the positive electrode, injecting negative charges from the negative electrode, and transferring and meeting the positive charges and the negative charges in the organic layer to emit light compositely under the action of an electric field. Because the OLED device has the advantages of high brightness, quick response, wide viewing angle, simple process, flexibility and the like, the OLED device has a great deal of attention in the novel display technical field and the novel illumination technical field. At present, the technology is widely applied to display panels of products such as novel illumination lamps, smart phones and tablet computers, and further expands the application field of large-size display products such as televisions, and is a novel display technology with rapid development and high technical requirements.
With the continuous advancement of the OLED in the two fields of illumination and display, the research on the core materials of the OLED is also more focused. This is because an efficient, long-life OLED device is typically the result of an optimized match of device structure and various organic materials. In order to prepare the OLED light-emitting device with lower driving voltage, better light-emitting efficiency and longer service life of the device, the performance of the OLED device is continuously improved, the structure and the manufacturing process of the OLED device are required to be innovated, and the photoelectric functional material in the OLED device is required to be continuously researched and innovated so as to prepare the functional material with higher performance. Based on this, the OLED materials community has been striving to develop new organic electroluminescent materials to achieve low starting voltage, high luminous efficiency and better lifetime of the device.
The TADF material can realize the internal quantum efficiency of 100% in theory by utilizing the up-conversion process from the triplet state to the singlet state, thereby realizing high-efficiency luminescence. The traditional TADF molecule is of a highly distorted electron donor-acceptor structure, and cannot give consideration to both high reverse intersystem channeling rate and high radiation transition rate, so that the efficiency of the TADF is further improved, and the TADF material emits light in a CT state, has a wider spectrum and cannot meet the requirements of BT.2020 on light color, so that the further application of the TADF material in the display field is limited. Boron-nitrogen multi-resonance MR-TAD The F material has the advantages of high color purity and high luminous efficiency, and is widely focused in scientific research and industry. However, due to the peripheral substituent pair S 1 The energy level has little influence, i.e. the light color of the material is difficult to regulate and control, the light color is always limited in the blue-deep blue region, and delta E is caused by the large overlap of HOMO and LUMO ST The rate of reverse intersystem leaping is relatively slow, so that the MR-TADF material is greatly limited to further application in the fields of high-resolution display, full-color display, white light illumination and the like.
Disclosure of Invention
In order to solve the technical problems, the invention provides a compound of a general formula, in particular to a thick and impure boron-nitrogen organic compound, the structure of which is shown as a general formula (I):
in formula (I), ring A 1 Ring A 2 Ring A 3 And ring A 4 Each independently selected from any one of a substituted or unsubstituted C5 to C60 aromatic ring, a substituted or unsubstituted C3 to C60 heteroaromatic ring;
and ring A 1 Ring A 2 Ring A 3 And ring A 4 At least one of which is a substituted or unsubstituted dibenzofive-membered heterocycle, the heteroatom of which is selected from S, O, se or N;
ring A 1 Ring A 2 Ring A 3 And ring A 4 Each of the substituted substituents is independently selected from deuterium, halogen, cyano, nitro, hydroxy, amino, unsubstituted or R 1 Substituted C1-C20 straight or branched alkyl, unsubstituted or R 1 Substituted C3-C20 cycloalkyl, unsubstituted or R 1 Substituted C1-C20 alkoxy, unsubstituted or R 1 Substituted C1-C20 alkylsilyl, unsubstituted or R 1 Substituted C1-C20 alkylamino, unsubstituted or R 1 Substituted C6-C30 arylamino, unsubstituted or R 1 Substituted C3-C30 heteroaryl amino, unsubstituted or R 1 Substituted C6-C30 aryloxyUnsubstituted or R 1 Substituted C3-C30 heteroaryloxy, unsubstituted or R 1 Substituted C6-C60 aryl, unsubstituted or R 1 One of substituted C3-C60 heteroaryl;
and ring A 1 Ring A 2 Ring A 3 And ring A 4 Wherein each of said substituted substituents is independently unconnected, or two adjacent substituents are linked by a chemical bond to form a ring; ring A 1 Ring A 2 Ring A 3 And ring A 4 Wherein each of the substituted substituents is independently unconnected to an adjacent ring structure or is connected to an adjacent ring structure through a chemical bond to form a ring;
the R is 1 Each independently selected from one or a combination of two of halogen, cyano, nitro, hydroxy, amino, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, 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;
The Z is 1 、Z 2 、Z 3 、Z 4 And Z 5 Each independently selected from CR 2 Or N, the R 2 Each independently selected from one or a combination of two of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, 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; and adjacent R 2 Are not connected or are connected into a ring through chemical bonds.
The compound of the invention is characterized in that at least two heteroaromatic rings are fused on a parent nucleus of BN multi-resonance material, at least one of the heteroaromatic rings is heterocycle containing S, O or Se structurally, and the compound maintains a rigid structure of molecules while realizing the red shift of light color by expanding a conjugated plane, has larger vibrator strength and is beneficial to improving the luminous efficiency. And heavy atoms such as S, se are introduced, so that the spin-orbit coupling effect is enhanced, the reverse intersystem jump rate of molecules is improved, the TADF performance is improved, and the light emitting effect of high efficiency and low roll-off is realized. Such a structure is also advantageous in increasing the horizontal orientation of the molecules to increase the light extraction efficiency of the OLED device. When the organic light emitting diode is used as a luminescent material in an OLED device, the organic light emitting diode shows excellent device performance and stability, and can realize a green OLED device with high efficiency, low roll-off and high color purity.
It should be noted that the possible actions of the individual groups/features are described separately in this application for ease of illustration, but this does not mean that the groups/features are acting in isolation. In fact, the reason for achieving good performance is essentially an optimized combination of the whole molecule, as a result of the synergy between the individual groups and structures, rather than the effect of a single group or structure.
In the present invention, unless otherwise specified, the expression of chemical elements includes the concept of isotopes having the same chemical properties, for example, hydrogen (H) includes 1 H (protium), 2 H (deuterium, D), 3 H (tritium, T), etc.; carbon (C) then comprises 12 C、 13 C, etc.
In the present invention, the heteroatom of the heteroaryl group is selected from the group of atoms or groups of atoms in N, O, S, P, B, si or Se, preferably N, O, S.
In the present invention, the expression "ring structure" means that the linking site is located at any position on the ring structure that can be bonded.
In the present invention, the expression of Ca-Cb means that the group has a carbon number of a-b, and generally the carbon number does not include the carbon number of the substituent unless otherwise specified.
In the present specification, "each independently" means that the subject has a plurality of subjects, and the subjects may be the same or different from each other.
In the present invention, the halogen includes fluorine, chlorine, bromine or iodine.
In the present invention, the C6-C30 (e.g., C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28) aromatic rings include mono-aromatic rings and fused aromatic rings; the single aromatic ring includes benzene ring, biphenyl ring or terphenyl ring, the condensed aromatic ring means that at least 2 aromatic rings are contained in the ring,and the aromatic rings share two adjacent carbon atoms fused to each other, exemplary include, but are not limited to: naphthalene ring, anthracene ring, phenanthrene ring, indene ring, fluorene ring and derivatives thereof (9, 9-dimethylfluorene ring, benzofluorene ring, etc.), fluoranthene ring, triphenylene ring, pyrene ring, perylene ring,
Ring or tetracyclic ring, and the like.
The C3-C30 (e.g., C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28) heteroaromatic ring includes a single heteroaromatic ring or a fused heteroaromatic ring. The single heteroaromatic ring illustratively includes, but is not limited to: pyrrole ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, furan ring, thiophene ring, pyrrole ring, and the like. The fused heteroaromatic ring means that the ring structure contains at least one aromatic heterocycle and one aromatic ring (aromatic heterocycle or aromatic ring) and two adjacent atoms are fused together, and exemplary includes but is not limited to: quinoline ring, isoquinoline ring, quinoxaline ring, quinazoline ring, benzofuran ring, benzothiophene ring, isobenzofuran ring, isobenzothiophene ring, indole ring, dibenzofuran ring, dibenzothiophene ring, carbazole ring, and derivatives thereof (N-phenylcarbazole ring, benzocarbazole ring, dibenzocarbazole ring, indolocarbazole ring, azacarbazole ring, etc.), acridine ring, phenothiazine ring, phenoxazine ring, hydrogenated acridine ring, etc.
In the present invention, the C1-C20 straight chain alkyl group or branched alkyl group. For example, a linear or branched alkyl group such as C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, or C18; preferably a C1-C16 linear or branched alkyl group; further preferred are C1-C10 straight or branched alkyl groups; exemplary include, but are 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.
Specific examples of the C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, or C18) alkoxy group according to the present invention include monovalent groups obtained by linking the above-mentioned examples of straight-chain or branched alkyl groups to O.
In the present invention, the C3-C20 cycloalkyl groups may be C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or the like cycloalkyl groups; exemplary include, but are not limited to: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, and the like.
A specific example of the C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, or C18, etc.) alkylsilyl group is-SiH 3 A monovalent group obtained by substituting at least one hydrogen of the above straight-chain or branched alkyl group; specific examples of the C1-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17 or C18, etc.) alkylamino group are-NH 2 A monovalent group obtained by substituting at least one hydrogen of the above-mentioned linear or branched alkyl group.
Specific examples of the C2-C20 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, or C18, etc.) heterocycloalkyl group according to the present invention include monovalent groups obtained by substituting at least one ring C atom of the above cycloalkyl group with a heteroatom (e.g., O, S, N or P, etc.), and exemplary examples include, but are not limited to: epoxy, tetrahydropyrrolyl, tetrahydrofuranyl, tetrahydrothienyl, morpholinyl, piperidinyl, and the like.
In the present invention, the C6-C60 aryl groups may be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56 or C58, etc., and preferably C6-C30 aryl groups, including monocyclic aryl groups or condensed ring aryl groups. By monocyclic aryl is meant that the group contains at least 1 phenyl group and when at least 2 phenyl groups are present, the phenyl groups are linked by single bonds, exemplary including but not limited to: phenyl, biphenyl, terphenyl, and the like; by fused ring aryl is meant a group containing at least 2 aromatic rings in the group and having two adjacent carbon atoms in common between the aromatic rings that are fused to each other, exemplary include, but are not limited to: naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof (9, 9-dimethylfluorenyl, 9-diphenylfluorenyl, 9-dinaphthyl fluorenyl) Spirobifluorenyl, benzofluorenyl, etc.), fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, and the like,
A radical or a tetracenyl radical, etc.; the foregoing list of groups includes all possible linkages thereof.
In the present invention, the C3-C60 heteroaryl groups may be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, or C58, etc., heteroaryl groups, preferably C3-C30 heteroaryl groups, still more preferably C4-C20 heteroaryl groups, including monocyclic heteroaryl groups or fused ring heteroaryl groups. The monocyclic heteroaryl means that at least one heteroaryl group is contained in the molecule, and when a heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.) are contained in the molecule, the heteroaryl group and other groups are linked by a single bond, and exemplary examples include, but are not limited to: furyl, thienyl, pyrrolyl, pyridyl, and the like. By fused ring heteroaryl is meant a group having at least one aromatic heterocycle and one aromatic ring (either aromatic heterocycle or aromatic ring) in the molecule and sharing two adjacent atoms fused to each other, exemplary including but not limited to: benzofuranyl, benzothienyl, isobenzofuranyl, isobenzothienyl, indolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and derivatives thereof (N-phenylcarbazolyl, N-naphthylcarbazolyl, benzocarbazolyl, dibenzocarbazolyl, indolocarbazolyl, azacarbazolyl, etc.), acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, hydrogenated acridinyl, etc.; the foregoing list of groups includes all possible linkages thereof.
Specific examples of the C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28) arylene group of the present invention include divalent groups obtained by removing one hydrogen atom in the above examples of aryl groups; specific examples of the C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28) heteroarylene group include a divalent group obtained by removing one hydrogen atom from the above heteroaryl group.
Specific examples of the C6-C30 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28) aryloxy group according to the present invention include monovalent groups obtained by linking the above-mentioned aryl group to O; specific examples of the C3-C30 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, or C28) heteroaryloxy group include monovalent groups obtained by linking the above heteroaryl group with O.
The C6-C60 (e.g., C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, or C58, etc.) arylamino groups, preferably C6-C30 arylamino groups, of the invention are-NH 2 The monovalent groups to which at least one hydrogen is substituted with the above aryl groups, illustratively include, but are not limited to: phenylamino, methylphenylamino, naphthylamino, anthracenylamino, phenanthrylamino, biphenylamino, and the like.
The C3-C60 (e.g., C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, C50, C52, C54, C56, or C58, etc.) heteroarylamino group, preferably C3-C30 heteroarylamino group, of the present invention is-NH 2 Examples of monovalent groups to which at least one hydrogen is substituted with a heteroaryl group as described above include, but are not limited to: pyridylamino, pyrimidinylamino, dibenzofuranylamino and the like.
Further, the compound of the present invention has a structure as shown in the general formula (1):
ring A 1 Ring A 2 Ring A 3 Ring A 4 、Z 1 、Z 2 、Z 3 、Z 4 And Z 5 The same meaning as expressed in claim 1;
preferably, the ring A 1 Ring A 2 Ring A 3 And ring A 4 One or both of which are substitutedOr an unsubstituted dibenzofive-membered heterocycle, the heteroatom of which is selected from S, O, se or N;
more preferably, the ring A 1 Ring A 2 Ring A 3 And ring A 4 Is a substituted or unsubstituted dibenzofive-membered heterocycle, the heteroatom of which is selected from S, se or N.
Still further, the compound of the present invention has a structure as shown in any one of the formulae (1-1) to (1-4):
in the formulae (1-1) to (1-4), the ring A 1 Ring A 2 Ring A 3 Ring A 4 、Z 1 、Z 2 、Z 3 、Z 4 And Z 5 The same meaning as expressed in claim 1;
Y 1 -Y 14 each independently selected from CR 3 Or N, the R 3 Each independently selected from one or a combination of two of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, 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; and adjacent R 3 Are not connected or are connected into a ring through chemical bonds.
Further, in the general formula of the compound of the present invention, the ring A 1 Ring A 2 Ring A 3 Ring A 4 Each independently selected from one of substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted N-phenylcarbazole, and not both substituted or unsubstituted N-phenylcarbazole;
ring A 1 Ring A 2 Ring A 3 And ring A 4 Wherein each of the substituted substituents is independently selected from deuterium, halogen, cyano, nitro, hydroxy, ammonia A group selected from the group consisting of C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.
Further, the compound of the present invention has a structure as shown in any one of the formulae (2) to (29):
in the general formulae (2) to (29), X 1 And X 2 Each independently selected from S, O, se or N-R c And X is 1 And X 2 Not simultaneously N-R c ，R c Represented as substituted or unsubstituted C 6 -C 30 Aryl or C 3 -C 30 Heteroaryl;
Z 1 、Z 2 、Z 3 、Z 4 and Z 5 The same meaning as expressed in claim 1; y is Y 1 -Y 14 The same meaning as expressed in claim 3;
when R is c When a substituent is present, the substituent groups are each independently selected from one or a combination of two of deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, 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, the compounds of the present invention have a structure as shown in any one of formulas (2), (3), (4), (5), (8), (9), (14), (15), (20), (21), (26) or (28).
Further, in the general formula of the compound of the present invention, R 1 、R 2 、R 3 Each independently selected from hydrogen, deuterium, deuterated or non-deuterated: 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, anthracenyl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, hole, perylene, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, terphenyl, tripolyphenyl, tetrabiphenyl, biphenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl substituted biphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroisopolyl indenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, 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, indazolyl, imidazolyl, benzimidazolyl, naphthyridinyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, benzothiophenyl, naphthyridazolyl, naphthyridin, anthrazolyl, phenanthrazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl 1, 8-diazapyrenyl, 4,5,9, 10-tetraazaperylenyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 1,2, 3-oxadiazolyl, and, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, 9-dimethylacridyl, (poly) halobenzene, (poly) cyanobenzene or (poly) trifluoromethylbenzene;
R c selected from deuterated or non-deuterated groups: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, pyrazinyl, phenazinyl, azacarbazolyl, phenothiazinyl phenanthroline, benzothiadiazolyl, 9-dimethylacridyl, (poly) halobenzene, (poly) cyanobenzene, (poly) trifluoromethylbenzene;
Preferably, R 1 、R 2 、R 3 Each independently selected from hydrogen, deuterium, deuterated or non-deuterated: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl, phenyl, naphthyl, anthryl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, biphenyl, terphenyl, biphenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenylA group, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthalimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, pyrazinyl, phenazinyl, phenothiazinyl, azacarbazolyl, phenanthroline, 1,3, 5-triazinyl, benzothiadiazolyl, 9-dimethylacridyl, (poly) cyano, (poly) fluoro-benzene, or poly (fluoro-benzoyl).
Further, the compounds of the general formula (1) according to the present invention may preferably be represented by the following specific structural compounds, which are merely representative:
the invention also provides application of the compound shown in any one of the general formula (I) and the formula (1) to the formula (29), wherein the application is as a functional material in an organic electronic device, and the organic electronic device comprises: organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information labels, electronic artificial skin sheets, sheet scanners or electronic papers, preferably organic electroluminescent devices.
The invention also provides an organic electroluminescent device comprising a substrate comprising a first electrode, a second electrode and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layers comprise a compound represented by any one of the above general formulae (1) to (29).
Specifically, an embodiment of the present invention provides an organic electroluminescent device including a substrate, and an anode layer, a plurality of light emitting functional layers, and a cathode layer sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole 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; preferably, the light-emitting layer contains the compound of the present invention represented by any one of the above general formulae (1) to (29).
The OLED device prepared by the compound has low starting voltage, high luminous efficiency, high color purity and better service life, and can meet the requirements of current panel manufacturing enterprises on high-performance materials.
The specific reasons for the excellent performance of the above-described compounds of the present invention when used as organic electroluminescent devices are not clear, and the following is an assumption by the inventors, but these predictions do not limit the scope of the present invention:
(1) The general formula compound is characterized in that at least two heteroaromatic rings are fused on a parent nucleus of a BN multi-resonance material, at least one of the heteroaromatic rings is a heterocycle containing S, O or Se structurally, a conjugate plane is expanded to realize light color red shift, and meanwhile, a rigid structure of molecules is maintained, so that the compound has larger vibrator strength and is beneficial to improving luminous efficiency. (2) The general formula compound enhances the spin-orbit coupling effect by introducing S, se and other heavy atoms, is beneficial to improving the reverse intersystem jump rate of molecules so as to improve the TADF performance, effectively realizes high-efficiency low-roll-off luminescence, and reduces the power consumption of the device. (3) The compound of the general formula has higher molecular level orientation, and is beneficial to improving the light extraction efficiency of an OLED device, thereby improving the luminous efficiency of the device. (4) The substituent group connected with the lower surface of the compound of the general formula has larger steric hindrance, and can inhibit the problems of concentration quenching, exciton annihilation, spectrum broadening and the like caused by molecular accumulation, thereby improving the performance of the device. (5) The spectrum of the compound with the general formula is narrower in half-width and higher in light color purity, and the color gamut of the device can be effectively improved, so that the compound is expected to further meet the requirement on ultra-high definition display.
The preparation process of the compound is simple and feasible, raw materials are easy to obtain, and the compound is suitable for mass production and amplification. When the compound provided by the invention is used as a luminescent material in an OLED device, the compound shows excellent device performance and stability, and a green OLED device with high efficiency, low roll-off and high color purity can be realized.
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.
The various chemicals used in the present invention, such as petroleum ether, ethyl acetate, sodium sulfate, toluene, methylene chloride, o-dichlorobenzene, potassium carbonate, 9H-carbazole, cesium carbonate, reaction intermediates, and other basic chemical raw materials, are all purchased from Shanghai Taitan technologies, inc. and Anhuizhen technologies, inc. The mass spectrometer used for determining the following compounds was ZAB-HS type mass spectrometer measurement (manufactured by Micromass Co., UK).
More specifically, the synthetic methods of representative compounds of the present invention are given below.
Synthetic examples:
synthesis of intermediate 1:
2-bromo-1, 3-difluoro-5-iodobenzene (10.74 g,33.67 mmol), phenylboronic acid (4.52 g,37.04 mmol) was dissolved in 150mL toluene, and tetrakis triphenylphosphine palladium (1.95 g,1.68 mmol) and 20mL aqueous potassium carbonate solution (9.31 g,67.34 mmol) were added and heated at reflux for 24h. After cooling, separating, extracting and drying, column chromatography (petroleum ether: dichloromethane=3:1) gave intermediate 1 as a white solid, weighing 6.8g, 75% yield.
Synthesis of intermediate 2-26:
synthesis of intermediate 2: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with (4- (tert-butyl) phenyl) boronic acid, and intermediate 2 was obtained as a white solid in 72% yield.
Synthesis of intermediate 3: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with (3, 5-di-tert-butylphenyl) boronic acid, and intermediate 3 was obtained as a white solid in 68% yield.
Synthesis of intermediate 4: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with [1,1' -biphenyl ] -4-ylboronic acid, and intermediate 4 was obtained as a white solid in 72% yield.
Synthesis of intermediate 5: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with (4 '- (tert-butyl) - [1,1' -biphenyl ] -4-yl) boronic acid, and intermediate 5 was obtained as a white solid in 67% yield.
Synthesis of intermediate 6: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with (3 ',5' -di-tert-butyl- [1,1' -biphenyl ] -4-yl) boronic acid and intermediate 6 was obtained as a white solid in 63% yield.
Synthesis of intermediate 7: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with ((2 r,6 r) -2- (3- (tert-butyl) -6-isopropyl-9H-carbazol-9-yl) -6- (3, 6-di-tert-butyl-9H-carbazol-9-yl) phenyl) boronic acid, affording intermediate 7 as a white solid in 56% yield.
Synthesis of intermediate 8: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with (4- (3, 6-bis (3, 5-di-tert-butylphenyl)) -9H-carbazol-9-yl) phenyl) boronic acid, affording intermediate 8 as a white solid in 57% yield.
Synthesis of intermediate 9: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with (4-benzonitrile) boronic acid, and intermediate 9 was obtained as a white solid in 68% yield.
Synthesis of intermediate 10: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with (3-benzonitrile) boronic acid, and intermediate 10 was obtained as a white solid in 66% yield.
Synthesis of intermediate 11: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with (2-benzonitrile) boronic acid, and intermediate 11 was obtained as a white solid in 51% yield.
Synthesis of intermediate 12: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with (2, 4-dicyanophenyl) boronic acid, and intermediate 12 was obtained as a white solid in 55% yield.
Synthesis of intermediate 13: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with (3, 5-dicyanophenyl) boronic acid, and intermediate 13 was obtained as a white solid in 52% yield.
Synthesis of intermediate 14: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with (4- (trifluoromethyl) phenyl) boronic acid and intermediate 14 was obtained as a white solid in 46% yield.
Synthesis of intermediate 15: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with (3- (trifluoromethyl) phenyl) boronic acid and intermediate 15 was obtained as a white solid in 58% yield.
Synthesis of intermediate 16: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with (2- (trifluoromethyl) phenyl) boronic acid, and intermediate 16 was obtained as a white solid in 47% yield.
Synthesis of intermediate 17: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with pyridin-4-ylboronic acid, and intermediate 17 was obtained as a white solid in 68% yield.
Synthesis of intermediate 18: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with quinolin-4-ylboronic acid, and intermediate 18 was obtained as a white solid in 75% yield.
Synthesis of intermediate 19: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with (4, 6-diphenyl-1, 3, 5-triazin-2-yl) boronic acid and intermediate 19 was obtained as a white solid in 71% yield.
Synthesis of intermediate 20: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with (9-methyl-9H-carbazol-3-yl) boronic acid, yielding intermediate 20 as a white solid in 73% yield.
Synthesis of intermediate 21: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with (9-phenyl-9H-carbazol-3-yl) boronic acid, and intermediate 21 was obtained as a white solid in 56% yield.
Synthesis of intermediate 22: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with (9- (4-tert-butyl) phenyl) -9H-carbazol-3-yl) boronic acid and intermediate 22 was obtained as a white solid in 58% yield.
Synthesis of intermediate 23: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with dibenzo [ b, d ] furan-2-ylboronic acid, yielding intermediate 23 as a white solid in 59% yield.
Synthesis of intermediate 24: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with dibenzo [ b, d ] thiophen-2-ylboronic acid, yielding intermediate 24 as a white solid in 60% yield.
Synthesis of intermediate 25: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with (4- (diphenylamino) phenyl) boronic acid and intermediate 25 was obtained as a white solid in 61% yield.
Synthesis of intermediate 26: the synthesis was similar to intermediate 1, except that phenylboronic acid was replaced with (4- (9H-carbazol-9-yl)) phenyl) boronic acid, and intermediate 26 was obtained as a white solid in 51% yield.
Synthesis example 1: synthesis of Compound 1
1) Synthesis of intermediate compounds 1-2:
in a 100mL dry, two-necked round bottom flask was charged intermediate 1 (3 mmol), 12H-benzo [4,5 ]]Thieno [2,3-a ]]Carbazole (3 mmol), cs 2 CO 3 (3.3 mmol), DMF (100 mL). Under nitrogen atmosphere, the mixture was heated to 150℃and the reaction was refluxed for 24 hours. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel column chromatography (developer: petroleum ether: dichloromethane=3:1) to give intermediate compound 1-1 as a white solid.
Next, in a 100mL dry two-necked round bottom flask, was added intermediate 1-1 (3 mmol), 5-phenyl-5, 11-indolino [3,2-b ]]Carbazole (3 mmol), cs 2 CO 3 (3.3 mmol), DMF (100 mL). Under nitrogen atmosphere, the mixture was heated to 150℃and the reaction was refluxed for 24 hours. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel chromatography (developer: petroleum ether: dichloromethane=4:1) to give intermediate compound 1-2 as a white solid.
2) Synthesis of compound 1:
a solution of tert-butyllithium in pentane (1.60M, 6.6 mmol) was slowly added to a solution of intermediate compounds 1-2 (3 mmol) in tert-butylbenzene (150 mL) at 0deg.C, followed by sequential heating to 60deg.C for 3 hours each. After the reaction was completed, the temperature was lowered to-30℃and boron tribromide (7.5 mmol) was slowly added thereto, followed by stirring at room temperature for 0.5 hour. N, N-diisopropylethylamine (15 mmol) was added at room temperature and the reaction was continued for 5 hours at 145 ℃. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel chromatography (developer: petroleum ether: dichloromethane=15:1) to give the objective compound 1 (0.57 g,25% yield, HPLC analysis purity 99.26%) as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 763.23; elemental analysis experimental values: c,84.92; h,3.97; b,1.40; n,5.52; s,4.18.
Synthesis example 2: synthesis of Compound 2
1) Synthesis of intermediate compound 2-2:
in a 100mL dry, two-necked round bottom flask was charged intermediate 1 (3 mmol), 12H-benzo [4,5 ]]Thieno [3,2-a ]]Carbazole (3 mmol), cs 2 CO 3 (3.3 mmol), DMF (100 mL). Under nitrogen atmosphere, the mixture was heated to 150℃and the reaction was refluxed for 24 hours. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel chromatography (developer: petroleum ether: dichloromethane=3:1) to give intermediate compound 2-1 as a white solid.
Next, in a 100mL dry two-necked round bottom flask, intermediate 2-1 (3 mmol), 5-phenyl-5, 11-indolino [3,2-b ] was added]Carbazole (3 mmol), cs 2 CO 3 (3.3 mmol), DMF (100 mL). Under nitrogen atmosphere, the mixture was heated to 150℃and the reaction was refluxed for 24 hours. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel chromatography (developer: petroleum ether: dichloromethane=4:1) to give intermediate compound 2-2 as a white solid.
2) Synthesis of compound 2:
a solution of tert-butyllithium in pentane (1.60M, 6.6 mmol) was slowly added to a solution of intermediate compound 2-2 (3 mmol) in tert-butylbenzene (150 mL) at 0deg.C, followed by sequential heating to 60deg.C for 3 hours each. After the reaction was completed, the temperature was lowered to-30℃and boron tribromide (7.5 mmol) was slowly added thereto, followed by stirring at room temperature for 0.5 hour. N, N-diisopropylethylamine (15 mmol) was added at room temperature and the reaction was continued for 5 hours at 145 ℃. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel chromatography (developer: petroleum ether: dichloromethane=15:1) to give the objective compound 2 (0.50 g,22% yield, HPLC analysis purity 99.01%) as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 763.23; elemental analysis experimental values: c,84.92; h,3.98; b,1.41; n,5.51; s,4.18.
Synthesis example 3: synthesis of Compound 3
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 2, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 819.29; elemental analysis experimental values: c,84.97; h,4.67; b,1.33; n,5.13; s,3.92.
Synthesis example 4: synthesis of Compound 4
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 2, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 819.29; elemental analysis experimental values: c,84.97; h,4.67; b,1.32; n,5.13; s,3.91.
Synthesis example 5: synthesis of Compound 5
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 3, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 875.35; elemental analysis experimental values: c,85.01; h,5.29; b,1.22; n,4.80; s,3.66.
Synthesis example 6: synthesis of Compound 6
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 3, the product was a yellow solid with 18% yield, MALDI-TOF-MS result: molecular ion peak: 875.35; elemental analysis experimental values: c,85.01; h,5.29; b,1.23; n,4.80; s,3.66.
Synthesis example 7: synthesis of Compound 7
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 4, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 839.26; elemental analysis experimental values: c,85.81; h,4.07; b,1.29; n,5.00; s,3.82.
Synthesis example 8: synthesis of Compound 8
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 4, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 839.26; elemental analysis experimental values: c,85.81; h,4.08; b,1.28; n,5.00; s,3.82.
Synthesis example 9: synthesis of Compound 9
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 5, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 895.32; elemental analysis experimental values: c,85.81; h,4.72; b,1.21; n,4.69; s,3.58.
Synthesis example 10: synthesis of Compound 10
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 5, the product was a yellow solid with 26% yield, MALDI-TOF-MS result: molecular ion peak: 895.32; elemental analysis experimental values: c,85.80; h,4.72; b,1.24; n,4.68; s,3.58.
Synthesis example 11: synthesis of Compound 11
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 6, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 951.38; elemental analysis experimental values: c,85.79; h,5.29; b,1.14; n,4.41; s,3.37.
Synthesis example 12: synthesis of Compound 12
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 6, the product was a yellow solid with a yield of 23%, MALDI-TOF-MS result: molecular ion peak: 951.38; elemental analysis experimental values: c,85.78; h,5.29; b,1.14; n,4.41; s,3.37.
Synthesis example 13: synthesis of Compound 13
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 7, the product was a yellow solid with a yield of 23%, MALDI-TOF-MS results: molecular ion peak: 1303.58; elemental analysis experimental values: c,85.62; h,5.72; b,0.83; n,5.37; s,2.46.
Synthesis example 14: synthesis of Compound 14
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 7, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS result: molecular ion peak: 1303.58; elemental analysis experimental values: c,85.63; h,5.72; b,0.82; n,5.37; s,2.46.
Synthesis example 15: synthesis of Compound 15
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 8, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 1304.60; elemental analysis experimental values: c,86.48; h,5.95; b,0.83; n,4.29; s,2.46.
Synthesis example 16: synthesis of Compound 16
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 8, the product was a yellow solid with 26% yield, MALDI-TOF-MS result: molecular ion peak: 1304.60; elemental analysis experimental values: c,86.48; h,5.95; b,0.83; n,4.29; s,2.46.
Synthesis example 17: synthesis of Compound 17
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 9, the product was a yellow solid with 27% yield, MALDI-TOF-MS result: molecular ion peak: 788.22; elemental analysis experimental values: c,83.77; h,3.71; b,1.37; n,7.10; s,4.06.
Synthesis example 18: synthesis of Compound 18
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 9, the product was a yellow solid with 17% yield, MALDI-TOF-MS result: molecular ion peak: 788.22; elemental analysis experimental values: c,83.76; h,3.71; b,1.37; n,7.10; s,4.06.
Synthesis example 19: synthesis of Compound 19
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 10, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 788.22; elemental analysis experimental values: c,83.76; h,3.71; b,1.37; n,7.10; s,4.08.
Synthesis example 20: synthesis of Compound 20
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 10, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 788.22; elemental analysis experimental values: c,83.77; h,3.71; b,1.37; n,7.10; s,4.06.
Synthesis example 21: synthesis of Compound 21
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 11, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 788.22; elemental analysis experimental values: c,83.76; h,3.71; b,1.37; n,7.10; s,4.06.
Synthesis example 22: synthesis of Compound 22
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 11, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 788.22; elemental analysis experimental values: c,83.76; h,3.72; b,1.37; n,7.10; s,4.06.
Synthesis example 23: synthesis of Compound 23
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 12, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 813.22; elemental analysis experimental values: c,82.66; h,3.47; b,1.32; n,8.61; s,3.94.
Synthesis example 24: synthesis of Compound 24
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 12, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 813.22; elemental analysis experimental values: c,82.66; h,3.47; b,1.33; n,8.61; s,3.94.
Synthesis example 25: synthesis of Compound 25
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 13, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 813.22; elemental analysis experimental values: c,82.65; h,3.47; b,1.33; n,8.61; s,3.94.
Synthesis example 26: synthesis of Compound 26
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 13, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 813.22; elemental analysis experimental values: c,82.66; h,3.47; b,1.33; n,8.61; s,3.94.
Synthesis example 27: synthesis of Compound 27
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 14, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: c,79.43; h,3.51; b,1.32; f,6.83; n,5.05; s,3.85.
Synthesis example 28: synthesis of Compound 28
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 14, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: c,79.43; h,3.51; b,1.30; f,6.84; n,5.05; s,3.85.
Synthesis example 29: synthesis of Compound 29
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 15, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: c,79.43; h,3.51; b,1.30; f,6.85; n,5.05; s,3.85.
Synthesis example 30: synthesis of Compound 30
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 15, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: c,79.43; h,3.51; b,1.30; f,6.85; n,5.05; s,3.85.
Synthesis example 31: synthesis of Compound 31
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 16, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: c,79.43; h,3.52; b,1.30; f,6.85; n,5.05; s,3.85.
Synthesis example 32: synthesis of Compound 32
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 16, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: c,79.43; h,3.51; b,1.31; f,6.85; n,5.05; s,3.85.
Synthesis example 33: synthesis of Compound 33
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 17, the product was a yellow solid with 15% yield, MALDI-TOF-MS result: molecular ion peak: 764.22; elemental analysis experimental values: c,83.25; h,3.82; b,1.41; n,7.33; s,4.19.
Synthesis example 34: synthesis of Compound 34
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 17, the product was a yellow solid with a yield of 28%, MALDI-TOF-MS results: molecular ion peak: 764.22; elemental analysis experimental values: c,83.24; h,3.83; b,1.41; n,7.33; s,4.19.
Synthesis example 35: synthesis of Compound 35
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 18, the product was a yellow solid with a yield of 25%, MALDI-TOF-MS results: molecular ion peak: 814.24; elemental analysis experimental values: c,84.03; h,3.84; b,1.32; n,6.88; s,3.93.
Synthesis example 36: synthesis of Compound 36
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 18, the product was a yellow solid with 27% yield, MALDI-TOF-MS result: molecular ion peak: 814.24; elemental analysis experimental values: c,84.01; h,3.84; b,1.33; n,6.88; s,3.93.
Synthesis example 37: synthesis of Compound 37
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 19, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS results: molecular ion peak: 918.27; elemental analysis experimental values: c,82.35; h,3.84; b,1.18; n,9.17; s,3.49.
Synthesis example 38: synthesis of Compound 38
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 19, the product was a yellow solid with a yield of 23%, MALDI-TOF-MS result: molecular ion peak: 918.27; elemental analysis experimental values: c,82.35; h,3.84; b,1.18; n,9.15; s,3.49.
Synthesis example 39: synthesis of Compound 39
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 20, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 866.27; elemental analysis experimental values: c,84.52; h,4.07; b,1.25; n,6.46; s,3.70.
Synthesis example 40: synthesis of Compound 40
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 20, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 866.27; elemental analysis experimental values: c,84.51; h,4.08; b,1.26; n,6.46; s,3.70.
Synthesis example 41: synthesis of Compound 41
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 21, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 928.28; elemental analysis experimental values: c,85.34; h,4.01; b,1.16; n,6.03; s,3.45.
Synthesis example 42: synthesis of Compound 42
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 21, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 928.28; elemental analysis experimental values: c,85.34; h,4.03; b,1.16; n,6.03; s,3.45.
Synthesis example 43: synthesis of Compound 43
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 22, the product was a yellow solid with 26% yield, MALDI-TOF-MS result: molecular ion peak: 984.35; elemental analysis experimental values: c,85.34; h,4.60; b,1.10; n,5.69; s,3.25.
Synthesis example 44: synthesis of Compound 44
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 22, the product was a yellow solid with 26% yield, MALDI-TOF-MS result: molecular ion peak: 984.35; elemental analysis experimental values: c,85.35; h,4.60; b,1.11; n,5.69; s,3.25.
Synthesis example 45: synthesis of Compound 45
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 23, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 853.24; elemental analysis experimental values: c,84.42; h,3.78; b,1.27; n,4.92; o,1.87; s,3.75.
Synthesis example 46: synthesis of Compound 46
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 23, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 853.24; elemental analysis experimental values: c,84.42; h,3.78; b,1.27; n,4.92; o,1.87; s,3.75.
Synthesis example 47: synthesis of Compound 47
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 24, the product was a yellow solid with 17% yield, MALDI-TOF-MS result: molecular ion peak: 869.21; elemental analysis experimental values: c,82.85; h,3.74; b,1.24; n,4.83; s,7.37.
Synthesis example 48: synthesis of Compound 48
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 24, the product was a yellow solid with 18% yield, MALDI-TOF-MS result: molecular ion peak: 869.21; elemental analysis experimental values: c,82.85; h,3.72; b,1.24; n,4.83; s,7.37.
Synthesis example 49: synthesis of Compound 49
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 25, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 930.30; elemental analysis experimental values: c,85.15; h,4.22; b,1.16; n,6.02; s,3.44.
Synthesis example 50: synthesis of Compound 50
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 25, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS result: molecular ion peak: 930.30; elemental analysis experimental values: c,85.15; h,4.22; b,1.16; n,6.02; s,3.44.
Synthesis example 51: synthesis of Compound 51
The synthesis was similar to compound 1, except that intermediate 1 was exchanged for intermediate 26, the product was a yellow solid with a yield of 25%, MALDI-TOF-MS results: molecular ion peak: 928.28; elemental analysis experimental values: c,85.34; h,4.01; b,1.16; n,6.03; s,3.45.
Synthesis example 52: synthesis of Compound 52
The synthesis was similar to compound 2, except that intermediate 1 was exchanged for intermediate 26, the product was a yellow solid with 29% yield, MALDI-TOF-MS result: molecular ion peak: 928.28; elemental analysis experimental values: c,85.34; h,4.01; b,1.18; n,6.03; s,3.45.
Synthesis example 53: synthesis of Compound 53
1) Synthesis of intermediate compound 53-2:
in a 100mL dry, two-necked round bottom flask was charged intermediate 1 (3 mmol), 12H-benzo [4,5 ]]Thieno [2,3-a ]]Carbazole (3 mmol), cs 2 CO 3 (3.3 mmol), DMF (100 mL). Under nitrogen atmosphere, the mixture was heated to 150℃and the reaction was refluxed for 24 hours. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel chromatography (developer: petroleum ether: dichloromethane=3:1) to give intermediate compound 53-1 as a white solid.
Next, intermediate 53-1 (3 mmol), 5- (4-tert-butyl) phenyl-5, 11-indolino [3,2-b ] was added to a 100mL dry, two neck round bottom flask]Carbazole (3 mmol), cs 2 CO 3 (3.3 mmol), DMF (100 mL). Under nitrogen atmosphere, the mixture was heated to 150℃and the reaction was refluxed for 24 hours. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel chromatography (developer: petroleum ether: dichloromethane=4:1) to give intermediate compound 53-2 as a white solid.
2) Synthesis of compound 53:
a solution of tert-butyllithium in pentane (1.60M, 6.6 mmol) was slowly added to a solution of intermediate compound 53-2 (3 mmol) in tert-butylbenzene (150 mL) at 0deg.C, followed by sequential heating to 60deg.C for 3 hours each. After the reaction was completed, the temperature was lowered to-30℃and boron tribromide (7.5 mmol) was slowly added thereto, followed by stirring at room temperature for 0.5 hour. N, N-diisopropylethylamine (15 mmol) was added at room temperature and the reaction was continued for 5 hours at 145 ℃. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel chromatography (developer: petroleum ether: dichloromethane=15:1) to give the objective compound 53 (27% yield, purity 98.52% by HPLC) as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 819.29; elemental analysis experimental values: c,84.97; h,4.67; b,1.32; n,5.13; s,3.92.
Synthesis example 54: synthesis of Compound 55
The synthesis was similar to compound 53, except that intermediate 1 was exchanged for intermediate 2, the product was a yellow solid with 26% yield, MALDI-TOF-MS result: molecular ion peak: 875.35; elemental analysis experimental values: c,85.02; h,5.28; b,1.23; n,4.80; s,3.66.
Synthesis example 55: synthesis of Compound 57
The synthesis was similar to compound 53, except that intermediate 1 was exchanged for intermediate 3, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 931.41; elemental analysis experimental values: c,85.05; h,5.84; b,1.16; n,4.52; s,3.44.
Synthesis example 56: synthesis of Compound 65
The synthesis was similar to compound 53, except that intermediate 1 was exchanged for intermediate 7, the product was a yellow solid with a yield of 23%, MALDI-TOF-MS results: molecular ion peak: 1359.64; elemental analysis experimental values: c,85.63; h,6.07; b,0.79; n,5.15; s,2.36.
Synthesis example 57: synthesis of Compound 67
The synthesis was similar to compound 53, except that intermediate 1 was exchanged for intermediate 8, the product was a yellow solid with 17% yield, MALDI-TOF-MS result: molecular ion peak: 1360.66; elemental analysis experimental values: c,86.44; h,6.29; b,0.79; n,4.13; s,2.35.
Synthesis example 58: synthesis of Compound 69
The synthesis was similar to compound 53, except that intermediate 1 was exchanged for intermediate 9, the product was a yellow solid with 18% yield, MALDI-TOF-MS result: molecular ion peak: 844.28; elemental analysis experimental values: c,83.88; h,4.41; b,1.27; n,6.63; s,3.79.
Synthesis example 59: synthesis of Compound 79
The synthesis was similar to compound 53, except that intermediate 1 was exchanged for intermediate 14, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 887.28; elemental analysis experimental values: c,79.82; h,4.20; b,1.22; f,6.42; n,4.73; s,3.61.
Synthesis example 60: synthesis of Compound 89
The synthesis was similar to compound 53, except that intermediate 1 was exchanged for intermediate 19, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 974.34; elemental analysis experimental values: c,82.54; h,4.45; b,1.12; n,8.62; s,3.29.
Synthesis example 61: synthesis of Compound 97
The synthesis was similar to compound 53, except that intermediate 1 was exchanged for intermediate 23, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 909.30; elemental analysis experimental values: c,84.48; h,4.43; b,1.19; n,4.62; o,1.76; s,3.52.
Synthesis example 62: synthesis of Compound 99
The synthesis was similar to compound 53, except that intermediate 1 was exchanged for intermediate 24, the product was a yellow solid with a yield of 23%, MALDI-TOF-MS results: molecular ion peak: 925.28; elemental analysis experimental values: c,83.02; h,4.34; b,1.17; n,4.54; s,6.92.
Synthesis example 63: synthesis of Compound 105
1) Synthesis of intermediate compound 105-2:
in a 100mL dry, two-necked round bottom flask was charged intermediate 1 (3 mmol), 12H-benzo [4,5 ]]Thieno [2,3-a ]]Carbazole (3 mmol), cs 2 CO 3 (3.3 mmol), DMF (100 mL). Under nitrogen atmosphere, the mixture was heated to 150℃and the reaction was refluxed for 24 hours. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel column chromatography (developer: petroleum ether: dichloromethane=3:1) to give intermediate compound 105-1 as a white solid.
Next, in a 100mL dry two-necked round bottom flask, intermediate 105-1 (3 mmol), 11H-benzofuro [3,2-b ] was added]Carbazole (3 mmol), cs 2 CO 3 (3.3 mmol), DMF (100 mL). Under nitrogen atmosphere, the mixture was heated to 150℃and the reaction was refluxed for 24 hours. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel chromatography (developer: petroleum ether: dichloromethane=4:1) to give intermediate compound 105-2 as a white solid.
2) Synthesis of compound 105:
a solution of tert-butyllithium in pentane (1.60M, 6.6 mmol) was slowly added to a solution of intermediate compound 105-2 (3 mmol) in tert-butylbenzene (150 mL) at 0deg.C, followed by sequential heating to 60deg.C for 3 hours each. After the reaction was completed, the temperature was lowered to-30℃and boron tribromide (7.5 mmol) was slowly added thereto, followed by stirring at room temperature for 0.5 hour. N, N-diisopropylethylamine (15 mmol) was added at room temperature and the reaction was continued for 5 hours at 145 ℃. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel chromatography (developer: petroleum ether: dichloromethane=15:1) to give the objective compound 105 (23% yield, purity 98.82% by HPLC) as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 688.18; elemental analysis experimental values: c,83.72; h,3.66; b,1.57; n,4.07; o,2.32; s,4.66.
Synthesis example 64: synthesis of Compound 107
The synthesis was similar to compound 105, except that intermediate 1 was exchanged for intermediate 2, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 744.24; elemental analysis experimental values: c,83.87; h,4.47; b,1.45; n,3.76; o,2.15; s,4.30.
Synthesis example 65: synthesis of Compound 109
The synthesis was similar to compound 105, except that intermediate 1 was exchanged for intermediate 3, the product was a yellow solid with 17% yield, MALDI-TOF-MS result: molecular ion peak: 800.30; elemental analysis experimental values: c,83.99; h,5.17; b,1.35; n,3.50; o,2.00; s,4.00.
Synthesis example 66: synthesis of Compound 117
The synthesis was similar to compound 105, except that intermediate 1 was exchanged for intermediate 7, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 1228.53; elemental analysis experimental values: c,85.00; h,5.66; b,0.88; n,4.56; o,1.31; s,2.61.
Synthesis example 67: synthesis of Compound 119
The synthesis was similar to compound 105, except that intermediate 1 was exchanged for intermediate 8, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS result: molecular ion peak: 1229.55; elemental analysis experimental values: c,85.92; h,5.90; b,0.88; n,3.42; o,1.30; s,2.61.
Synthesis example 68: synthesis of Compound 121
The synthesis was similar to compound 105, except that intermediate 1 was exchanged for intermediate 9, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 713.17; elemental analysis experimental values: c,82.47; h,3.39; b,1.51; n,5.89; o,2.24; s,4.49.
Synthesis example 69: synthesis of Compound 131
The synthesis was similar to compound 105, except that intermediate 1 was exchanged for intermediate 14, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 756.17; elemental analysis experimental values: c,77.79; h,3.20; b,1.42; f,7.53; n,3.70; o,2.11; s,4.24.
Synthesis example 70: synthesis of Compound 141
The synthesis was similar to compound 105, except that intermediate 1 was exchanged for intermediate 19, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 843.23; elemental analysis experimental values: c,81.14; h,3.58; b,1.28; n,8.30; o,1.90; s,3.80.
Synthesis example 71: synthesis of Compound 149
The synthesis was similar to compound 105, except that intermediate 1 was exchanged for intermediate 23, the product was a yellow solid with a yield of 23% and MALDI-TOF-MS results: molecular ion peak: 778.19; elemental analysis experimental values: c,83.29; h,3.50; b,1.39; n,3.60; o,4.11; s,4.12.
Synthesis example 72: synthesis of Compound 151
The synthesis was similar to compound 105, except that intermediate 1 was exchanged for intermediate 24, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 794.17; elemental analysis experimental values: c,81.61; h,3.42; b,1.36; n,3.52; o,2.01; s,8.07.
Synthesis example 73: synthesis of Compound 157
1) Synthesis of intermediate compound 157-2:
in a 100mL dry, two-necked round bottom flask was charged intermediate 1 (3 mmol), 12H-benzo [4,5 ]]Thieno [2,3-a ]]Carbazole (3 mmol), cs 2 CO 3 (3.3 mmol), DMF (100 mL). Under nitrogen atmosphere, the mixture was heated to 150℃and the reaction was refluxed for 24 hours. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel column chromatography (developer: petroleum ether: dichloromethane=3:1) to give intermediate compound 157-1 as a white solid.
Next, intermediate 157-1 (3 mmol), 11H-benzo [4,5 ] was added to a 100mL dry, two-necked round bottom flask]Thieno [3,2-b]Carbazole (3 mmol), cs 2 CO 3 (3.3 mmol), DMF (100 mL). Under nitrogen atmosphere, the mixture was heated to 150℃and the reaction was refluxed for 24 hours. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel column chromatography (developer: petroleum ether: dichloromethane=4:1) to give intermediate compound 157-2 as a white solid.
2) Synthesis of compound 157:
a solution of tert-butyllithium in pentane (1.60M, 6.6 mmol) was slowly added to a solution of intermediate compound 157-2 (3 mmol) in tert-butylbenzene (150 mL) at 0deg.C, followed by sequential heating to 60deg.C for 3 hours each. After the reaction was completed, the temperature was lowered to-30℃and boron tribromide (7.5 mmol) was slowly added thereto, followed by stirring at room temperature for 0.5 hour. N, N-diisopropylethylamine (15 mmol) was added at room temperature and the reaction was continued for 5 hours at 145 ℃. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel chromatography (developer: petroleum ether: dichloromethane=15:1) to give the objective compound 157 (22% yield, HPLC analysis purity 97.66%) as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 704.16; elemental analysis experimental values: c,81.82; h,3.58; b,1.53; n,3.98; s,9.10.
Synthesis example 74: synthesis of Compound 159
The synthesis was similar to compound 157, except that intermediate 1 was exchanged for intermediate 2, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 760.22; elemental analysis experimental values: c,82.10; h,4.37; b,1.42; n,3.68; s,8.43.
Synthesis example 75: synthesis of Compound 161
The synthesis was similar to compound 157, except that intermediate 1 was exchanged for intermediate 3, the product was a yellow solid with a yield of 16%, MALDI-TOF-MS results: molecular ion peak: 816.28; elemental analysis experimental values: c,82.34; h,5.06; b,1.33; n,3.43; s,7.85.
Synthesis example 76: synthesis of Compound 169
The synthesis was similar to compound 157, except that intermediate 1 was exchanged for intermediate 7, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 1244.51; elemental analysis experimental values: c,83.90; h,5.58; b,0.87; n,4.50; s,5.15.
Synthesis example 77: synthesis of Compound 171
The synthesis was similar to compound 157, except that intermediate 1 was exchanged for intermediate 8, the product was a yellow solid with 18% yield, MALDI-TOF-MS result: molecular ion peak: 1245.53; elemental analysis experimental values: c,84.81; h,5.82; b,0.87; n,3.37; s,5.14.
Synthesis example 78: synthesis of Compound 173
The synthesis was similar to compound 157, except that intermediate 1 was exchanged for intermediate 9, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 729.15; elemental analysis experimental values: c,80.66; h,3.32; b,1.48; n,5.76; s,8.79.
Synthesis example 79: synthesis of Compound 183
The synthesis was similar to compound 157, except that intermediate 1 was exchanged for intermediate 14, the product was a yellow solid with a yield of 23%, MALDI-TOF-MS results: molecular ion peak: 772.14; elemental analysis experimental values: c,76.17; h,3.13; b,1.41; f,7.36; n,3.63; s,8.30.
Synthesis example 80: synthesis of Compound 193
The synthesis was similar to compound 157, except that intermediate 1 was exchanged for intermediate 19, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 859.20; elemental analysis experimental values: c,79.62; h,3.52; b,1.26; n,8.15; s,7.46.
Synthesis example 81: synthesis of Compound 201
The synthesis was similar to compound 157, except that intermediate 1 was exchanged for intermediate 23, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 794.17; elemental analysis experimental values: c,81.61; h,3.42; b,1.36; n,3.52; o,2.01; s,8.07.
Synthesis example 82: synthesis of Compound 203
The synthesis was similar to compound 157, except that intermediate 1 was exchanged for intermediate 24, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 810.14; elemental analysis experimental values: c,79.99; h,3.36; b,1.32; n,3.46; s,11.86.
Synthesis example 83: synthesis of Compound 209
The synthesis was similar to compound 157, except that 11H-benzo [4,5] thieno [3,2-b ] carbazole was replaced with 11H-benzo [4,5] seleno-benzo [3,2-b ] carbazole, the product was a yellow solid with a yield of 21% MALDI-TOF-MS result: molecular ion peak: 752.10; elemental analysis experimental values: c,76.71; h,3.35; b,1.44; n,3.73; s,4.26; se,10.51.
Synthesis example 84: synthesis of Compound 211
The synthesis was similar to compound 209, except that intermediate 1 was exchanged for intermediate 2, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 808.16; elemental analysis experimental values: c,77.33; h,4.12; b,1.34; n,3.47; s,3.97; se,9.78.
Synthesis example 85: synthesis of Compound 213
The synthesis was similar to compound 209, except that intermediate 1 was exchanged for intermediate 3, the product was a yellow solid with 20% yield, MALDI-TOF-MS result: molecular ion peak: 864.22; elemental analysis experimental values: c,77.87; h,4.78; b,1.25; n,3.24; s,3.71; se,9.14.
Synthesis example 86: synthesis of Compound 221
The synthesis was similar to compound 209, except that intermediate 1 was exchanged for intermediate 7, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 1292.45; elemental analysis experimental values: c,80.86; h,5.38; b,0.84; n,4.34; s,2.48; se,6.11.
Synthesis example 87: synthesis of Compound 223
The synthesis was similar to compound 209, except that intermediate 1 was exchanged for intermediate 8, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 1293.47; elemental analysis experimental values: c,81.72; h,5.61; b,0.86; n,3.25; s,2.48; se,6.11.
Synthesis example 88: synthesis of Compound 225
The synthesis was similar to compound 209, except that intermediate 1 was exchanged for intermediate 9, the product was a yellow solid with 26% yield, MALDI-TOF-MS result: molecular ion peak: 777.09; elemental analysis experimental values: c,75.78; h,3.12; b,1.39; n,5.41; s,4.13; se,10.17.
Synthesis example 89: synthesis of Compound 235
The synthesis was similar to compound 209, except that intermediate 1 was exchanged for intermediate 14, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 820.09; elemental analysis experimental values: c,71.81; h,2.95; b,1.32; f,6.95; n,3.42; s,3.91; se,9.64.
Synthesis example 90: synthesis of Compound 245
The synthesis was similar to compound 209, except that intermediate 1 was exchanged for intermediate 19, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 907.15; elemental analysis experimental values: c,75.51; h,3.35; b,1.16; n,7.72; s,3.54; se,8.71.
Synthesis example 91: synthesis of Compound 253
The synthesis was similar to compound 209, except that intermediate 1 was exchanged for intermediate 23, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 842.11; elemental analysis experimental values: c,77.06; h,3.23; b,1.28; n,3.33; o,1.90; s,3.81; se,9.38.
Synthesis example 92: synthesis of Compound 255
The synthesis was similar to compound 209, except that intermediate 1 was exchanged for intermediate 24, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 858.09; elemental analysis experimental values: c,75.63; h,3.17; b,1.26; n,3.27; s,7.48; se,9.21.
Synthesis example 93: synthesis of Compound 261
1) Synthesis of intermediate compound 261-2:
in a 100mL dry, two-necked round bottom flask was charged intermediate 1 (3 mmol), 12H-benzo [4,5 ] ]Thieno [2,3-a ]]Carbazole (3 mmol), cs 2 CO 3 (3.3 mmol), DMF (100 mL). Under nitrogen atmosphere, the mixture was heated to 150℃and the reaction was refluxed for 24 hours. After the reaction is completed, the reaction mixture is stirred,naturally cooling to room temperature, removing the solvent by rotary evaporation, and purifying the crude product by silica gel chromatography column (developer: petroleum ether: dichloromethane=3:1) to obtain intermediate compound 261-1 as white solid.
Next, in a 100mL dry two-necked round bottom flask, was added intermediate 261-1 (3 mmol), 12-phenyl-5, 12-indolino [3,2-a ]]Carbazole (3 mmol), cs 2 CO 3 (3.3 mmol), DMF (100 mL). Under nitrogen atmosphere, the mixture was heated to 150℃and the reaction was refluxed for 24 hours. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel chromatography (developer: petroleum ether: dichloromethane=4:1) to give intermediate compound 261-2 as a white solid.
2) Synthesis of compound 261:
a solution of tert-butyllithium in pentane (1.60M, 6.6 mmol) was slowly added to a solution of intermediate compound 261-2 (3 mmol) in tert-butylbenzene (150 mL) at 0deg.C, followed by sequential heating to 60deg.C for 3 hours each. After the reaction was completed, the temperature was lowered to-30℃and boron tribromide (7.5 mmol) was slowly added thereto, followed by stirring at room temperature for 0.5 hour. N, N-diisopropylethylamine (15 mmol) was added at room temperature and the reaction was continued for 5 hours at 145 ℃. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel chromatography (developer: petroleum ether: dichloromethane=15:1) to give the objective compound 261 (23% yield, purity 99.21% by HPLC) as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 763.23; elemental analysis experimental values: c,84.93; h,3.98; b,1.40; n,5.53; s,4.18.
Synthesis example 94: synthesis of Compound 263
The synthesis was similar to compound 261, except that intermediate 1 was exchanged for intermediate 2, the product was a yellow solid with a yield of 23%, MALDI-TOF-MS result: molecular ion peak: 819.29; elemental analysis experimental values: c,84.97; h,4.69; b,1.32; n,5.13; s,3.91.
Synthesis example 95: synthesis of Compound 265
The synthesis was similar to compound 261, except that intermediate 1 was exchanged for intermediate 3, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 875.35; elemental analysis experimental values: c,85.02; h,5.29; b,1.23; n,4.81; s,3.66.
Synthesis example 96: synthesis of Compound 273
The synthesis was similar to compound 261, except that intermediate 1 was exchanged for intermediate 7, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 1303.58; elemental analysis experimental values: c,85.63; h,5.72; b,0.83; n,5.37; s,2.46.
Synthesis example 97: synthesis of Compound 275
The synthesis was similar to compound 261, except that intermediate 1 was exchanged for intermediate 8, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS result: molecular ion peak: 1304.60; elemental analysis experimental values: c,86.48; h,5.95; b,0.83; n,4.29; s,2.46.
Synthesis example 98: synthesis of Compound 277
The synthesis was similar to compound 261, except that intermediate 1 was exchanged for intermediate 9, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS result: molecular ion peak: 788.22; elemental analysis experimental values: c,83.76; h,3.72; b,1.38; n,7.10; s,4.06.
Synthesis example 99: synthesis of Compound 287
The synthesis was similar to compound 261, except that intermediate 1 was exchanged for intermediate 14, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS result: molecular ion peak: 831.21; elemental analysis experimental values: c,79.43; h,3.51; b,1.30; f,6.85; n,5.05; s,3.85.
Synthesis example 100: synthesis of Compound 297
The synthesis was similar to compound 261, except that intermediate 1 was exchanged for intermediate 19, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS result: molecular ion peak: 918.27; elemental analysis experimental values: c,82.35; h,3.84; b,1.18; n,9.15; s,3.49.
Synthesis example 101: synthesis of Compound 305
The synthesis was similar to compound 261, except that intermediate 1 was exchanged for intermediate 23, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 853.24; elemental analysis experimental values: c,84.41; h,3.78; b,1.28; n,4.92; o,1.87; s,3.75.
Synthesis example 102: synthesis of Compound 307
The synthesis was similar to compound 261, except that intermediate 1 was exchanged for intermediate 24, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 869.21; elemental analysis experimental values: c,82.85; h,3.71; b,1.24; n,4.83; s,7.37.
Synthesis example 103: synthesis of Compound 313
The synthesis was similar to compound 261, except that 12H-benzo [4,5] thieno [2,3-a ] carbazole was replaced with 3, 6-di-tert-butyl-12H-benzo [4,5] thieno [2,3-a ] carbazole, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 875.35; elemental analysis experimental values: c,85.02; h,5.28; b,1.23; n,4.80; s,3.66.
Synthesis example 104: synthesis of Compound 315
The synthesis was similar to compound 313, except that intermediate 1 was exchanged for intermediate 2, the product was a yellow solid with a yield of 23%, MALDI-TOF-MS result: molecular ion peak: 931.41; elemental analysis experimental values: c,85.07; h,5.84; b,1.16; n,4.51; s,3.44.
Synthesis example 105: synthesis of Compound 317
The synthesis was similar to compound 313, except that intermediate 1 was exchanged for intermediate 3, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 987.48; elemental analysis experimental values: c,85.08; h,6.32; b,1.09; n,4.25; s,3.24.
Synthesis example 106: synthesis of Compound 325
The synthesis was similar to compound 313, except that intermediate 1 was exchanged for intermediate 7, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS result: molecular ion peak: 1415.70; elemental analysis experimental values: c,85.63; h,6.40; b,0.76; n,4.94; s,2.26.
Synthesis example 107: synthesis of Compound 327
The synthesis was similar to compound 313, except that intermediate 1 was exchanged for intermediate 8, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 1416.72; elemental analysis experimental values: c,86.41; h,6.61; b,0.78; n,3.95; s,2.26.
Synthesis example 108: synthesis of Compound 329
The synthesis was similar to compound 313, except that intermediate 1 was exchanged for intermediate 9, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 900.35; elemental analysis experimental values: c,83.99; h,5.03; b,1.20; n,6.22; s,3.56.
Synthesis example 109: synthesis of Compound 339
The synthesis was similar to compound 313, except that intermediate 1 was exchanged for intermediate 14, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS results: molecular ion peak: 943.34; elemental analysis experimental values: c,80.16; h,4.81; b,1.15; f,6.02; n,4.45; s,3.40.
Synthesis example 110: synthesis of Compound 349
The synthesis was similar to compound 313, except that intermediate 1 was exchanged for intermediate 19, the product was a yellow solid with a yield of 23% and MALDI-TOF-MS results: molecular ion peak: 1030.40; elemental analysis experimental values: c,82.72; h,4.99; b,1.05; n,8.15; s,3.11.
Synthesis example 111: synthesis of Compound 357
The synthesis was similar to compound 313, except that intermediate 1 was exchanged for intermediate 23, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 965.36; elemental analysis experimental values: c,84.55; h,5.01; b,1.12; n,4.35; o,1.66; s,3.32.
Synthesis example 112: synthesis of Compound 359
The synthesis was similar to compound 313, except that intermediate 1 was exchanged for intermediate 24, the product was a yellow solid with 26% yield, MALDI-TOF-MS result: molecular ion peak: 981.34; elemental analysis experimental values: c,83.16; h,4.94; b,1.10; n,4.28; s,6.53.
Synthesis example 113: synthesis of Compound 365
The synthesis was similar to compound 1, except that 12H-benzo [4,5] thieno [2,3-a ] carbazole was replaced by 12H-benzofuro [2,3-a ] carbazole, the product was a yellow solid with 24% yield, MALDI-TOF-MS result: molecular ion peak: 747.25; elemental analysis experimental values: c,86.75; h,4.04; b,1.45; n,5.62; o,2.14.
Synthesis example 114: synthesis of Compound 367
The synthesis was similar to compound 365, except that intermediate 1 was exchanged for intermediate 2, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 803.31; elemental analysis experimental values: c,86.67; h,4.77; b,1.34; n,5.23; o,1.99.
Synthesis example 115: synthesis of Compound 369
The synthesis was similar to compound 365, except that intermediate 1 was exchanged for intermediate 3, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 859.37; elemental analysis experimental values: c,86.60; h,5.38; b,1.26; n,4.89; o,1.86.
Synthesis example 116: synthesis of Compound 377
The synthesis was similar to compound 365, except that intermediate 1 was exchanged for intermediate 7, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 1287.60; elemental analysis experimental values: c,86.69; h,5.79; b,0.84; n,5.44; o,1.24.
Synthesis example 117: synthesis of Compound 379
The synthesis was similar to compound 365, except that intermediate 1 was exchanged for intermediate 8, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 1288.62; elemental analysis experimental values: c,87.56; h,6.02; b,0.84; n,4.35; o,1.24.
Synthesis example 118: synthesis of Compound 381
The synthesis was similar to compound 365, except that intermediate 1 was exchanged for intermediate 9, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS result: molecular ion peak: 772.24; elemental analysis experimental values: c,85.51; h,3.78; b,1.40; n,7.25; o,2.07.
Synthesis example 119: synthesis of Compound 391
The synthesis was similar to compound 365, except that intermediate 1 was exchanged for intermediate 14, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS results: molecular ion peak: 815.24; elemental analysis experimental values: c,80.99; h,3.58; b,1.33; f,6.99; n,5.15; o,1.96.
Synthesis example 120: synthesis of Compound 401
The synthesis was similar to compound 365, except that intermediate 1 was exchanged for intermediate 19, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 902.30; elemental analysis experimental values: c,83.81; h,3.91; b,1.20; n,9.31; o,1.77.
Synthesis example 121: synthesis of Compound 409
The synthesis was similar to compound 365, except that intermediate 1 was exchanged for intermediate 23, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 837.26; elemental analysis experimental values: c,86.02; h,3.86; b,1.28; n,5.02; o,3.82.
Synthesis example 122: synthesis of Compound 411
The synthesis was similar to compound 365, except that intermediate 1 was exchanged for intermediate 24, the product was a yellow solid with a yield of 25%, MALDI-TOF-MS results: molecular ion peak: 853.24; elemental analysis experimental values: c,84.41; h,3.78; b,1.27; n,4.92; o,1.87; s,3.75.
Synthesis example 123: synthesis of Compound 417
The synthesis was similar to compound 1, except that 12H-benzo [4,5] thieno [2,3-a ] carbazole was replaced by 12H-benzo [4,5] seleno-benzo [2,3-a ] carbazole, the product was a yellow solid with 26% yield, MALDI-TOF-MS result: molecular ion peak: 811.17; elemental analysis experimental values: c,80.01; h,3.73; b,1.33; n,5.18; se,9.74.
Synthesis example 124: synthesis of Compound 419
The synthesis was similar to compound 417, except intermediate 1 was exchanged for intermediate 2, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 867.23; elemental analysis experimental values: c,80.38; h,4.42; b,1.25; n,4.85; se,9.11.
Synthesis example 125: synthesis of Compound 421
The synthesis was similar to compound 417, except intermediate 1 was exchanged for intermediate 3, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 923.30; elemental analysis experimental values: c,80.69; h,5.02; b,1.17; n,4.56; se,8.56.
Synthesis example 126: synthesis of Compound 429
The synthesis was similar to compound 417, except intermediate 1 was exchanged for intermediate 7, the product was a yellow solid with a yield of 23%, MALDI-TOF-MS result: molecular ion peak: 1351.52; elemental analysis experimental values: c,82.65; h,5.52; b,0.80; n,5.18; se,5.84.
Synthesis example 127: synthesis of Compound 431
The synthesis was similar to compound 417, except intermediate 1 was exchanged for intermediate 8, the product was a yellow solid with 17% yield, MALDI-TOF-MS result: molecular ion peak: 1352.54; elemental analysis experimental values: c,83.48; h,5.74; b,0.80; n,4.14; se,5.84.
Synthesis example 128: synthesis of Compound 433
The synthesis was similar to compound 417, except intermediate 1 was exchanged for intermediate 9, the product was a yellow solid with 27% yield, MALDI-TOF-MS result: molecular ion peak: 836.17; elemental analysis experimental values: c,79.05; h,3.50; b,1.28; n,6.70; se,9.45.
Synthesis example 129: synthesis of Compound 443
The synthesis was similar to compound 417, except intermediate 1 was exchanged for intermediate 14, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS result: molecular ion peak: 879.16; elemental analysis experimental values: c,75.18; h,3.33; b,1.23; f,6.49; n,4.78; se,8.99.
Synthesis example 130: synthesis of Compound 453
The synthesis was similar to compound 417, except intermediate 1 was exchanged for intermediate 19, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS result: molecular ion peak: 966.22; elemental analysis experimental values: c,78.35; h,3.65; b,1.12; n,8.72; se,8.18.
Synthesis example 131: synthesis of Compound 461
The synthesis was similar to compound 417, except intermediate 1 was exchanged for intermediate 23, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS result: molecular ion peak: 901.18; elemental analysis experimental values: c,80.01; h,3.58; b,1.20; n,4.67; o,1.78; se,8.77.
Synthesis example 132: synthesis of Compound 463
The synthesis was similar to compound 417, except intermediate 1 was exchanged for intermediate 24, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS result: molecular ion peak: 917.16; elemental analysis experimental values: c,78.62; h,3.52; b,1.18; n,4.58; s,3.51; se,8.61.
Synthesis example 133: synthesis of Compound 469
1) Synthesis of intermediate compound 469-2:
in a 100mL dry, two-necked round bottom flask was charged intermediate 1 (3 mmol), 12H-benzo [4,5 ] ]Thieno [2,3-a ]]Carbazole (3 mmol), cs 2 CO 3 (3.3 mmol), DMF (100 mL). Under nitrogen atmosphere, the mixture was heated to 150℃and the reaction was refluxed for 24 hours. After the reaction is completed, naturally cooling to room temperature, removing the solvent by rotary evaporation, and passing the crude product through siliconPurification by gel chromatography (developer: petroleum ether: dichloromethane=3:1) afforded intermediate compound 469-1 as a white solid.
Next, intermediate 469-1 (3 mmol), 5-phenyl-5, 8-indolino [2,3-c ] was added to a 100mL dry, two neck round bottom flask]Carbazole (3 mmol), cs 2 CO 3 (3.3 mmol), DMF (100 mL). Under nitrogen atmosphere, the mixture was heated to 150℃and the reaction was refluxed for 24 hours. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel chromatography (developer: petroleum ether: dichloromethane=4:1) to give intermediate compound 469-2 as a white solid.
2) Synthesis of compound 469:
a solution of tert-butyllithium in pentane (1.60M, 6.6 mmol) was slowly added to a solution of intermediate compound 469-2 (3 mmol) in tert-butylbenzene (150 mL) at 0deg.C, followed by sequential heating to 60deg.C for 3 hours each. After the reaction was completed, the temperature was lowered to-30℃and boron tribromide (7.5 mmol) was slowly added thereto, followed by stirring at room temperature for 0.5 hour. N, N-diisopropylethylamine (15 mmol) was added at room temperature and the reaction was continued for 5 hours at 145 ℃. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel chromatography (developer: petroleum ether: dichloromethane=15:1) to give the target compound 469 (24% yield, purity 99.56% by HPLC) as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 763.23; elemental analysis experimental values: c,84.93; h,3.98; b,1.40; n,5.52; s,4.18.
Synthesis example 134: synthesis of Compound 471
The synthesis was similar to compound 469, except that intermediate 1 was exchanged for intermediate 2, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 819.29; elemental analysis experimental values: c,84.97; h,4.67; b,1.32; n,5.13; s,3.91.
Synthesis example 135: synthesis of Compound 473
The synthesis was similar to compound 469, except that intermediate 1 was exchanged for intermediate 3, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS results: molecular ion peak: 875.35; elemental analysis experimental values: c,85.03; h,5.29; b,1.23; n,4.80; s,3.66.
Synthesis example 136: synthesis of Compound 481
The synthesis was similar to compound 469, except that intermediate 1 was exchanged for intermediate 7, the product was a yellow solid in 23% yield, MALDI-TOF-MS result: molecular ion peak: 1303.58; elemental analysis experimental values: c,85.63; h,5.72; b,0.85; n,5.35; s,2.46.
Synthesis example 137: synthesis of Compound 483
The synthesis was similar to compound 469, except that intermediate 1 was exchanged for intermediate 8, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 1304.60; elemental analysis experimental values: c,86.48; h,5.96; b,0.83; n,4.29; s,2.46.
Synthesis example 138: synthesis of Compound 485
The synthesis was similar to compound 469, except that intermediate 1 was exchanged for intermediate 9, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 788.22; elemental analysis experimental values: c,83.76; h,3.72; b,1.37; n,7.10; s,4.06.
Synthesis example 139: synthesis of Compound 495
The synthesis was similar to compound 469, except that intermediate 1 was exchanged for intermediate 14, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: c,79.41; h,3.51; b,1.30; f,6.86; n,5.05; s,3.85.
Synthesis example 140: synthesis of Compound 505
The synthesis was similar to compound 469, except that intermediate 1 was exchanged for intermediate 19, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 918.27; elemental analysis experimental values: c,82.35; h,3.84; b,1.18; n,9.16; s,3.49.
Synthesis example 141: synthesis of Compound 513
The synthesis was similar to compound 469, except that intermediate 1 was exchanged for intermediate 23, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 853.24; elemental analysis experimental values: c,84.41; h,3.78; b,1.27; n,4.92; o,1.87; s,3.75.
Synthesis example 142: synthesis of Compound 515
The synthesis was similar to compound 469, except that intermediate 1 was exchanged for intermediate 24, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 869.21; elemental analysis experimental values: c,82.85; h,3.71; b,1.24; n,4.83; s,7.37.
Synthesis example 143: synthesis of Compound 521
1) Synthesis of intermediate compound 521-2:
in a 100mL dry, two-necked round bottom flask was added intermediate 521 (3 mmol), 7H-benzo [4,5 ]]Thieno [2,3-b ]]Carbazole (3 mmol), cs 2 CO 3 (3.3 mmol), DMF (100 mL). Under nitrogen atmosphere, the mixture was heated to 150℃and the reaction was refluxed for 24 hours. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel column chromatography (developer: petroleum ether: dichloromethane=3:1) to give intermediate compound 521-1 as a white solid.
Next, intermediate 521-1 (3 mmol), 5-phenyl-5, 11-indolino [3,2-b ] was added to a 100mL dry, two neck round bottom flask]Carbazole (3 mmol), cs 2 CO 3 (3.3 mmol), DMF (100 mL). Under nitrogen atmosphere, the mixture was heated to 150℃and the reaction was refluxed for 24 hours. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel column chromatography (developer: petroleum ether: dichloromethane=4:1) to give intermediate compound 521-2 as a white solid.
2) Synthesis of compound 521:
a solution of tert-butyllithium in pentane (1.60M, 6.6 mmol) was slowly added to a solution of intermediate compound 521-2 (3 mmol) in tert-butylbenzene (150 mL) at 0deg.C, followed by sequential heating to 60deg.C for each reaction for 3 hours. After the reaction was completed, the temperature was lowered to-30℃and boron tribromide (7.5 mmol) was slowly added thereto, followed by stirring at room temperature for 0.5 hour. N, N-diisopropylethylamine (15 mmol) was added at room temperature and the reaction was continued for 5 hours at 145 ℃. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel chromatography (developer: petroleum ether: dichloromethane=15:1) to give the objective compound 521 (23% yield, HPLC analysis purity 98.76%) as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 763.23; elemental analysis experimental values: c,84.93; h,3.98; b,1.41; n,5.52; s,4.18.
Synthesis example 144: synthesis of Compound 523
The synthesis was similar to compound 521, except that intermediate 1 was exchanged for intermediate 2, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 819.29; elemental analysis experimental values: c,84.96; h,4.67; b,1.32; n,5.13; s,3.91.
Synthesis example 145: synthesis of Compound 525
The synthesis was similar to compound 521, except that intermediate 1 was exchanged for intermediate 3, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 875.35; elemental analysis experimental values: c,85.02; h,5.29; b,1.23; n,4.80; s,3.66.
Synthesis example 146: synthesis of Compound 533
The synthesis was similar to compound 521, except that intermediate 1 was exchanged for intermediate 7, the product was a yellow solid with 17% yield, MALDI-TOF-MS result: molecular ion peak: 1303.58; elemental analysis experimental values: c,85.64; h,5.72; b,0.82; n,5.37; s,2.46.
Synthesis example 147: synthesis of Compound 535
The synthesis was similar to compound 521, except that intermediate 1 was exchanged for intermediate 8, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 1304.60; elemental analysis experimental values: c,86.48; h,5.95; b,0.83; n,4.29; s,2.46.
Synthesis example 148: synthesis of Compound 537
The synthesis was similar to compound 521, except that intermediate 1 was exchanged for intermediate 9, the product was a yellow solid with a yield of 27%, MALDI-TOF-MS results: molecular ion peak: 788.22; elemental analysis experimental values: c,83.76; h,3.71; b,1.37; n,7.10; s,4.06.
Synthesis example 149: synthesis of Compound 547
The synthesis was similar to compound 521, except that intermediate 1 was exchanged for intermediate 14, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: c,79.43; h,3.51; b,1.31; f,6.86; n,5.06; s,3.86.
Synthesis example 150: synthesis of Compound 557
The synthesis was similar to compound 521, except that intermediate 1 was exchanged for intermediate 19, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS results: molecular ion peak: 918.27; elemental analysis experimental values: c,82.35; h,3.84; b,1.18; n,9.15; s,3.49.
Synthesis example 151: synthesis of Compound 565
The synthesis was similar to compound 521, except that intermediate 1 was exchanged for intermediate 23, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 853.24; elemental analysis experimental values: c,84.41; h,3.78; b,1.27; n,4.92; o,1.87; s,3.75.
Synthesis example 152: synthesis of Compound 567
The synthesis was similar to compound 521, except that intermediate 1 was exchanged for intermediate 24, the product was a yellow solid with 18% yield, MALDI-TOF-MS result: molecular ion peak: 869.21; elemental analysis experimental values: c,82.86; h,3.71; b,1.24; n,4.82; s,7.37.
Synthesis example 153: synthesis of Compound 573
The synthesis was similar to compound 521, except that 5-phenyl-5, 11-indolino [3,2-b ] carbazole was replaced with 12-phenyl-5, 12-indolino [3,2-a ] carbazole, the product was a yellow solid with a yield of 19% MALDI-TOF-MS results: molecular ion peak: 763.23; elemental analysis experimental values: c,84.93; h,3.98; b,1.42; n,5.51; s,4.18.
Synthesis example 154: synthesis of Compound 575
The synthesis was similar to compound 573, except that intermediate 1 was exchanged for intermediate 2, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 819.29; elemental analysis experimental values: c,84.97; h,4.66; b,1.32; n,5.13; s,3.91.
Synthesis example 155: synthesis of Compound 577
The synthesis was similar to compound 573, except that intermediate 1 was exchanged for intermediate 3, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 875.35; elemental analysis experimental values: c,85.02; h,5.29; b,1.23; n,4.80; s,3.66.
Synthesis example 156: synthesis of Compound 585
The synthesis was similar to compound 573, except that intermediate 1 was exchanged for intermediate 7, the product was a yellow solid with a yield of 23%, MALDI-TOF-MS results: molecular ion peak: 1303.58; elemental analysis experimental values: c,85.63; h,5.72; b,0.83; n,5.37; s,2.45.
Synthesis example 157: synthesis of Compound 587
The synthesis was similar to compound 573, except that intermediate 1 was exchanged for intermediate 8, the product was a yellow solid with a yield of 23%, MALDI-TOF-MS results: molecular ion peak: 1304.60; elemental analysis experimental values: c,86.48; h,5.95; b,0.83; n,4.29; s,2.46.
Synthesis example 158: synthesis of Compound 589
The synthesis was similar to compound 573, except that intermediate 1 was exchanged for intermediate 9, the product was a yellow solid with a yield of 23%, MALDI-TOF-MS results: molecular ion peak: 788.22; elemental analysis experimental values: c,83.76; h,3.71; b,1.37; n,7.10; s,4.06.
Synthetic example 159: synthesis of Compound 599
The synthesis was similar to compound 573, except that intermediate 1 was exchanged for intermediate 14, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: c,79.42; h,3.51; b,1.30; f,6.85; n,5.06; s,3.85.
Synthesis example 160: synthesis of Compound 609
The synthesis was similar to compound 573, except intermediate 1 was exchanged for intermediate 19, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 918.27; elemental analysis experimental values: c,82.35; h,3.84; b,1.18; n,9.15; s,3.49.
Synthesis example 161: synthesis of Compound 617
The synthesis was similar to compound 573, except that intermediate 1 was exchanged for intermediate 23, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 853.24; elemental analysis experimental values: c,84.41; h,3.78; b,1.28; n,4.92; o,1.87; s,3.75.
Synthesis example 162: synthesis of Compound 619
The synthesis was similar to compound 573, except that intermediate 1 was exchanged for intermediate 24, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 869.21; elemental analysis experimental values: c,82.87; h,3.71; b,1.24; n,4.83; s,7.36.
Synthesis example 163: synthesis of Compound 625
The synthesis was similar to compound 521, except that 5-phenyl-5, 11-indolino [3,2-b ] carbazole was replaced with 5-phenyl-4 a,5,8,12 d-tetrahydroindolo [2,3-c ] carbazole, the product was a yellow solid with a yield of 22% MALDI-TOF-MS result: molecular ion peak: 763.23; elemental analysis experimental values: c,84.93; h,3.98; b,1.41; n,5.52; s,4.18.
Synthesis example 164: synthesis of Compound 627
The synthesis was similar to compound 625, except that intermediate 1 was exchanged for intermediate 2, the product was a yellow solid with a yield of 23%, MALDI-TOF-MS results: molecular ion peak: 819.29; elemental analysis experimental values: c,84.97; h,4.67; b,1.32; n,5.13; s,3.91.
Synthesis example 165: synthesis of Compound 629
The synthesis was similar to compound 625, except that intermediate 1 was exchanged for intermediate 3, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 875.35; elemental analysis experimental values: c,85.02; h,5.28; b,1.23; n,4.80; s,3.66.
Synthesis example 166: synthesis of Compound 637
The synthesis was similar to compound 625, except that intermediate 1 was exchanged for intermediate 7, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 1303.58; elemental analysis experimental values: c,85.63; h,5.73; b,0.83; n,5.37; s,2.46.
Synthesis example 167: synthesis of Compound 639
The synthesis was similar to compound 625, except that intermediate 1 was exchanged for intermediate 8, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 1304.60; elemental analysis experimental values: c,86.48; h,5.95; b,0.83; n,4.29; s,2.46.
Synthesis example 168: synthesis of Compound 641
The synthesis was similar to compound 625, except that intermediate 1 was exchanged for intermediate 9, the product was a yellow solid with 27% yield, MALDI-TOF-MS result: molecular ion peak: 788.22; elemental analysis experimental values: c,83.76; h,3.71; b,1.38; n,7.10; s,4.06.
Synthesis example 169: synthesis of Compound 651
The synthesis was similar to compound 625, except that intermediate 1 was exchanged for intermediate 14, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: c,79.43; h,3.51; b,1.30; f,6.85; n,5.05; s,3.85.
Synthesis example 170: synthesis of Compound 661
The synthesis was similar to compound 625, except that intermediate 1 was exchanged for intermediate 19, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 918.27; elemental analysis experimental values: c,82.36; h,3.84; b,1.18; n,9.15; s,3.49.
Synthesis example 171: synthesis of Compound 669
The synthesis was similar to compound 625, except that intermediate 1 was exchanged for intermediate 23, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 853.24; elemental analysis experimental values: c,84.41; h,3.78; b,1.27; n,4.93; o,1.88; s,3.75.
Synthesis example 172: synthesis of Compound 671
The synthesis was similar to compound 625, except that intermediate 1 was exchanged for intermediate 24, the product was a yellow solid with a yield of 16%, MALDI-TOF-MS results: molecular ion peak: 869.21; elemental analysis experimental values: c,82.85; h,3.71; b,1.24; n,4.83; s,7.37.
Synthesis example 173: synthesis of Compound 729
1) Synthesis of intermediate compound 729-2:
in a 100mL dry, two-necked round bottom flask was charged intermediate 1 (3 mmol), 7H-benzo [4,5 ]]Thieno [2,3-b ]]Carbazole (3 mmol), cs 2 CO 3 (3.3 mmol), DMF (100 mL). Under nitrogen atmosphere, the mixture was heated to 150℃and the reaction was refluxed for 24 hours. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel column chromatography (developer: petroleum ether: dichloromethane=3:1) to give intermediate compound 729-1 as a white solid.
Next, in a 100mL dry two-necked round bottom flask, was added intermediate 729-1 (3 mmol), 11H-benzo [4,5 ]]The sequence of the thieno [3 ],2-b]carbazole (3 mmol), cs 2 CO 3 (3.3 mmol), DMF (100 mL). Under nitrogen atmosphere, the mixture was heated to 150℃and the reaction was refluxed for 24 hours. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel column chromatography (developer: petroleum ether: dichloromethane=4:1) to give intermediate compound 729-2 as a white solid.
2) Synthesis of compound 729:
a solution of tert-butyllithium in pentane (1.60M, 6.6 mmol) was slowly added to a solution of intermediate compound 729-2 (3 mmol) in tert-butylbenzene (150 mL) at 0deg.C, followed by sequential heating to 60deg.C for 3 hours each. After the reaction was completed, the temperature was lowered to-30℃and boron tribromide (7.5 mmol) was slowly added thereto, followed by stirring at room temperature for 0.5 hour. N, N-diisopropylethylamine (15 mmol) was added at room temperature and the reaction was continued for 5 hours at 145 ℃. After the reaction was completed, naturally cooled to room temperature, the solvent was removed by rotary evaporation, and the crude product was purified by silica gel chromatography (developer: petroleum ether: dichloromethane=15:1) to give the objective compound 729 (22% yield, 99.36% purity by HPLC) as a yellow solid. MALDI-TOF-MS results: molecular ion peak: 704.16; elemental analysis experimental values: c,81.82; h,3.58; b,1.53; n,3.98; s,9.12.
Synthesis example 174: synthesis of Compound 731
The synthesis was similar to that of compound 729, except that intermediate 1 was exchanged for intermediate 2, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 760.22; elemental analysis experimental values: c,82.10; h,4.37; b,1.42; n,3.68; s,8.43.
Synthesis example 175: synthesis of Compound 733
The synthesis was similar to that of compound 729, except that intermediate 1 was exchanged for intermediate 3, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 816.28; elemental analysis experimental values: c,82.33; h,5.06; b,1.32; n,3.42; s,7.85.
Synthesis example 176: synthesis of Compound 741
The synthesis was similar to that of compound 729, except that intermediate 1 was exchanged for intermediate 7, the product was a yellow solid with 20% yield, MALDI-TOF-MS result: molecular ion peak: 1244.51; elemental analysis experimental values: c,83.90; h,5.58; b,0.86; n,4.50; s,5.15.
Synthesis example 177: synthesis of Compound 743
The synthesis was similar to that of compound 729, except that intermediate 1 was exchanged for intermediate 8, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 1245.53; elemental analysis experimental values: c,84.80; h,5.82; b,0.87; n,3.37; s,5.14.
Synthesis example 178: synthesis of Compound 745
The synthesis was similar to that of compound 729, except that intermediate 1 was exchanged for intermediate 9, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 729.15; elemental analysis experimental values: c,80.66; h,3.33; b,1.48; n,5.76; s,8.79.
Synthesis example 179: synthesis of Compound 755
The synthesis was similar to that of compound 729, except that intermediate 1 was exchanged for intermediate 14, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 772.14; elemental analysis experimental values: c,76.17; h,3.13; b,1.40; f,7.38; n,3.65; s,8.30.
Synthesis example 180: synthesis of Compound 765
The synthesis was similar to that of compound 729, except that intermediate 1 was exchanged for intermediate 19, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 859.20; elemental analysis experimental values: c,79.61; h,3.51; b,1.26; n,8.15; s,7.46.
Synthesis example 181: synthesis of Compound 773
The synthesis was similar to that of compound 729, except that intermediate 1 was exchanged for intermediate 23, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS results: molecular ion peak: 794.17; elemental analysis experimental values: c,81.61; h,3.42; b,1.36; n,3.52; o,2.01; s,8.07.
Synthesis example 182: synthesis of Compound 775
The synthesis was similar to that of compound 729, except that intermediate 1 was exchanged for intermediate 24, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 810.14; elemental analysis experimental values: c,79.98; h,3.36; b,1.35; n,3.46; s,11.86.
Synthesis example 183: synthesis of Compound 781
The synthesis was similar to compound 521, except that 7H-benzo [4,5] thieno [2,3-b ] carbazole was replaced with 8H-benzo [4,5] thieno [2,3-c ] carbazole, the product was a yellow solid with a yield of 23% and MALDI-TOF-MS results: molecular ion peak: 763.23; elemental analysis experimental values: c,84.93; h,3.98; b,1.41; n,5.52; s,4.18.
Synthesis example 184: synthesis of Compound 783
The synthesis was similar to compound 781, except that intermediate 1 was exchanged for intermediate 2, the product was a yellow solid with 18% yield, MALDI-TOF-MS result: molecular ion peak: 819.29; elemental analysis experimental values: c,84.96; h,4.67; b,1.32; n,5.13; s,3.91.
Synthesis example 185: synthesis of Compound 785
The synthesis was similar to compound 781, except intermediate 1 was exchanged for intermediate 3, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 875.35; elemental analysis experimental values: c,85.02; h,5.29; b,1.23; n,4.81; s,3.66.
Synthesis example 186: synthesis of Compound 793
The synthesis was similar to compound 781, except intermediate 1 was exchanged for intermediate 7, the product was a yellow solid in 23% yield, MALDI-TOF-MS result: molecular ion peak: 1303.58; elemental analysis experimental values: c,85.63; h,5.73; b,0.83; n,5.37; s,2.46.
Synthesis example 187: synthesis of Compound 795
The synthesis was similar to compound 781, except intermediate 1 was exchanged for intermediate 8, the product was a yellow solid in 23% yield, MALDI-TOF-MS result: molecular ion peak: 1304.60; elemental analysis experimental values: c,86.48; h,5.95; b,0.83; n,4.29; s,2.46.
Synthesis example 188: synthesis of Compound 797
The synthesis was similar to compound 781, except intermediate 1 was exchanged for intermediate 9, the product was a yellow solid with 27% yield, MALDI-TOF-MS result: molecular ion peak: 788.22; elemental analysis experimental values: c,83.76; h,3.72; b,1.37; n,7.10; s,4.06.
Synthesis example 189: synthesis of Compound 807
The synthesis was similar to compound 781, except intermediate 1 was exchanged for intermediate 14, the product was a yellow solid in 25% yield, MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: c,79.43; h,3.51; b,1.31; f,6.85; n,5.05; s,3.85.
Synthesis example 190: synthesis of compound 817
The synthesis was similar to compound 781, except intermediate 1 was exchanged for intermediate 19, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS results: molecular ion peak: 918.27; elemental analysis experimental values: c,82.36; h,3.84; b,1.18; n,9.15; s,3.49.
Synthesis example 191: synthesis of Compound 825
The synthesis was similar to compound 781, except intermediate 1 was exchanged for intermediate 23, the product was a yellow solid with 26% yield, MALDI-TOF-MS result: molecular ion peak: 853.24; elemental analysis experimental values: c,84.41; h,3.78; b,1.28; n,4.93; o,1.87; s,3.75.
Synthesis example 192: synthesis of Compound 827
The synthesis was similar to compound 781, except intermediate 1 was exchanged for intermediate 24, the product was a yellow solid with 18% yield, MALDI-TOF-MS result: molecular ion peak: 869.21; elemental analysis experimental values: c,82.86; h,3.71; b,1.24; n,4.83; s,7.38.
Synthesis example 193: synthesis of Compound 833
The synthesis was similar to compound 781, except that 5-phenyl-5, 11-indolino [3,2-b ] carbazole was replaced with 12-phenyl-5, 12-indolino [3,2-a ] carbazole, the product was a yellow solid with a yield of 22% MALDI-TOF-MS result: molecular ion peak: 763.23; elemental analysis experimental values: c,84.93; h,3.99; b,1.42; n,5.51; s,4.18.
Synthesis example 194: synthesis of Compound 835
The synthesis was similar to compound 833, except that intermediate 1 was exchanged for intermediate 2, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 819.29; elemental analysis experimental values: c,84.97; h,4.67; b,1.31; n,5.13; s,3.91.
Synthesis example 195: synthesis of Compound 837
The synthesis was similar to compound 833, except that intermediate 1 was exchanged for intermediate 3, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 875.35; elemental analysis experimental values: c,85.01; h,5.29; b,1.23; n,4.80; s,3.66.
Synthesis example 196: synthesis of Compound 845
The synthesis was similar to compound 833, except that intermediate 1 was exchanged for intermediate 7, the product was a yellow solid with 22% yield, MALDI-TOF-MS result: molecular ion peak: 1303.58; elemental analysis experimental values: c,85.63; h,5.72; b,0.83; n,5.37; s,2.46.
Synthetic example 197: synthesis of Compound 847
The synthesis was similar to compound 833, except that intermediate 1 was exchanged for intermediate 8, the product was a yellow solid with a yield of 21%, MALDI-TOF-MS results: molecular ion peak: 1304.60; elemental analysis experimental values: c,86.48; h,5.95; b,0.82; n,4.29; s,2.46.
Synthesis example 198: synthesis of Compound 849
The synthesis was similar to compound 833, except that intermediate 1 was exchanged for intermediate 9, the product was a yellow solid with 26% yield, MALDI-TOF-MS result: molecular ion peak: 788.22; elemental analysis experimental values: c,83.76; h,3.71; b,1.38; n,7.10; s,4.06.
Synthesis example 199: synthesis of Compound 859
The synthesis was similar to compound 833, except that intermediate 1 was exchanged for intermediate 14, the product was a yellow solid with a yield of 24%, MALDI-TOF-MS results: molecular ion peak: 831.21; elemental analysis experimental values: c,79.43; h,3.51; b,1.30; f,6.85; n,5.05; s,3.85.
Synthesis example 200: synthesis of Compound 869
The synthesis was similar to compound 833, except intermediate 1 was exchanged for intermediate 19, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 918.27; elemental analysis experimental values: c,82.36; h,3.86; b,1.17; n,9.15; s,3.49.
Synthesis example 201: synthesis of Compound 877
The synthesis was similar to compound 833, except that intermediate 1 was exchanged for intermediate 23, the product was a yellow solid with a yield of 25% and MALDI-TOF-MS results: molecular ion peak: 853.24; elemental analysis experimental values: c,84.41; h,3.78; b,1.27; n,4.92; o,1.87; s,3.75.
Synthesis example 202: synthesis of Compound 879
The synthesis was similar to compound 833, except that intermediate 1 was exchanged for intermediate 24, the product was a yellow solid with a yield of 19%, MALDI-TOF-MS results: molecular ion peak: 869.21; elemental analysis experimental values: c,82.85; h,3.71; b,1.24; n,4.83; s,7.37.
The technical effects and advantages of the present invention are demonstrated and verified by testing practical use properties in the organic electroluminescent device by applying the compounds of the present invention specifically to the organic electroluminescent device.
The organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer between the two electrodes. The organic material may be divided into a plurality of regions, for example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
The material of the anode may be an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), zinc oxide (ZnO), or any combination thereof. The cathode may be made of metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag), or any combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer 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).
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, and the like.
Among them, aromatic amine derivatives are compounds shown as HT-1 to HT-34 below. If the material of the hole transport region 3 is an aromatic amine derivative, it may be one or more of the compounds shown as HT-1 through HT-34.
The hole injection layer is located between the anode 2 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-34 described above, or one or more of the compounds HI1 through HI3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI1 to HI3 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.
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 the present invention, the electron transport layer material may be selected from, but is not limited to, combinations of one or more of ET-1 to ET-57 listed below.
The light emitting device may further include an electron injection layer between the electron transport layer and the cathode 6, the electron injection layer material including, but not limited to, one or more combinations of the following: liQ, liF, naCl, csF Li2O, cs2CO3, baO, na, li, ca.
The preparation process of the organic electroluminescent device is described as follows: an anode 2, a hole transport layer 3, an organic light emitting layer 4, an electron transport layer 5, and a cathode 6 are sequentially deposited on a substrate 1, and then encapsulated. Wherein, in preparing the organic light emitting layer 4, the organic light emitting layer 4 is formed by co-evaporation of a wide band gap material source, an electron donor material source, an electron acceptor material source and a resonant TADF material source.
Specifically, the preparation method of the organic electroluminescent device comprises the following steps:
1. The anode material coated glass plate was sonicated in 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;
2. placing the glass plate with the anode in a vacuum cavity, vacuumizing to 1X 10 < -5 > -9X 10 < -3 > Pa, and vacuum evaporating a hole injection layer on the anode layer film, wherein the evaporation rate is 0.1-0.5nm/s;
3. vacuum evaporating a hole transport layer on the hole injection layer at an evaporation rate of 0.1-0.5nm/s,
4. vacuum evaporating a luminescent layer of the device on the hole transport layer, wherein the luminescent layer comprises a main body material and TADF dye, and the evaporation rate of the main body material, the evaporation rate of a sensitizer material and the evaporation rate of the dye are regulated by utilizing a multi-source co-evaporation method so that the dye reaches a preset doping proportion;
5. vacuum evaporating electron transport layer material of the device on the organic light emitting layer, wherein the evaporation rate is 0.1-0.5nm/s;
6. and (3) vacuum evaporation LiF with the concentration of 0.1-0.5nm/s is used as an electron injection layer on the electron transport layer, and vacuum evaporation Al with the concentration of 0.5-1nm/s is used as a cathode of the device.
The embodiment of the invention also provides a display device which comprises the organic electroluminescent device. The display device can be a display device such as an OLED display, and any product or component with a display function such as a television, a digital camera, a mobile phone, a tablet personal computer and the like comprising the display device. The display device has the same advantages as the organic electroluminescent device described above with respect to the prior art, and will not be described in detail herein.
The organic electroluminescent device according to the present invention will be further described by way of specific examples.
Example 1
The organic electroluminescent device structure prepared in this example is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％1(30nm)/HBL(10nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer material is HI, the general total thickness is 5-30nm, the embodiment is 10nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, and the thickness is 30nm in the embodiment; an electron blocking layer EBL (10 nm), host is a main material with wide band gap of an organic light emitting layer, the compound 1 is dye, the doping concentration is 3wt%, the thickness of the organic light emitting layer is generally 1-200nm, and the embodiment is 30nm; the hole blocking layer HBL (10 nm), the electron transport layer is made of ET, the thickness is generally 5-300nm, the embodiment is 30nm; the electron injection layer and the cathode material are LiF (0.5 nm) and metallic aluminum (150 nm).
Example 2
The same preparation method as in example 1 is distinguished in that the wide bandgap Host material Host used in the light emitting layer is replaced with a TADF Host TD, and the specific device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％1(30nm)/HBL(10nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
example 3
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 1 to 2. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％2(30nm)/HBL(10nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
example 4
The same preparation method as in example 2 was used, except that the dye used in the light-emitting layer was replaced with 1 to 2. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%2 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 5
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 1 to 3. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%3 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 6
The same preparation method as in example 2 was used, except that the dye used in the light-emitting layer was replaced with 1 to 3. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%3 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 7
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 1 to 4. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%4 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 8
The same preparation method as in example 2 was used, except that the dye used in the light-emitting layer was replaced with 4 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%4 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 9
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 1 to 5. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%5 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 10
The same preparation method as in example 2 was used, except that the dye used in the light-emitting layer was replaced with 1 to 5. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%5 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 11
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 1 to 6. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%6 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 12
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 6. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%6 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 13
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 7 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%7 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 14
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 7. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%7 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 15
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 1 to 8. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%8 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 16
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 8. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%8 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 17
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 9 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%9 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 18
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 9. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%9 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 19
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 1 to 10. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%10 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 20
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 10. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%10 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 21
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 11 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%11 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 22
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 11 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%11 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 23
The same preparation method as in example 1 was used except that the dye used in the light-emitting layer was replaced with 12 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%12 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 24
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 12. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%12 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 25
The same preparation method as in example 1 was used except that the dye used in the light-emitting layer was replaced with 13 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%13 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 26
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 13. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%13 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 27
The same preparation method as in example 1 was used except that the dye used in the light-emitting layer was replaced with 14 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%14 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 28
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 14. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3wt%14 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 29
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 15 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%15 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 30
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 15. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%15 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 31
The same preparation method as in example 1 was used except that the dye used in the light-emitting layer was replaced with 16 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%16 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 32
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 16. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%16 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 33
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 17 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%17 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 34
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 17 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%17 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 35
The same preparation method as in example 1 was used except that the dye used in the light-emitting layer was replaced with 18 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%18 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 36
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 18. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%18 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 37
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 1 to 19. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%19 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 38
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 19. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%19 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 39
The same preparation method as in example 1 was used except that the dye used in the light-emitting layer was replaced with 20 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%20 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 40
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 20. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%20 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 41
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 21 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%21 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 42
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 21. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%21 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 43
The same preparation method as in example 1 was used except that the dye used in the light-emitting layer was replaced with 22 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%22 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 44
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 22. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3wt%22 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 45
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 23 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%23 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 46
The same preparation method as in example 2 was used, except that the dye used in the light-emitting layer was replaced with 23 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%23 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 47
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 24 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%24 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 48
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 24. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%24 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 49
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 25 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%25 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 50
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 25. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%25 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 51
The same preparation method as in example 1 was used except that the dye used in the light-emitting layer was replaced with 26 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%26 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 52
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 26. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3wt%26 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 53
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 27 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%27 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 54
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 27 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3wt%27 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 55
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 28 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%28 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 56
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 28. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3wt%28 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 57
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 29 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%29 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 58
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 29 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%29 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 59
The same preparation method as in example 1 was used except that the dye used in the light-emitting layer was replaced with 1 to 30. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%30 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 60
The same preparation method as in example 2 was used except that the dye used in the light-emitting layer was replaced with 30 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%30 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 61
The same preparation method as in example 1 was used except that the dye used in the light-emitting layer was replaced with 31 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%31 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 62
The same preparation method as in example 2 was used except that the dye used in the light-emitting layer was replaced with 31 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%31 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 63
The same preparation method as in example 1 was used except that the dye used in the light-emitting layer was replaced with 32 by 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%32 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 64
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 32 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%32 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 65
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 33 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%33 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 66
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 33. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%33 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 67
The same preparation method as in example 1 was used except that the dye used in the light-emitting layer was replaced with 34 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%34 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 68
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 34 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%34 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 69
The same preparation method as in example 1 was used except that the dye used in the light-emitting layer was replaced with 35 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%35 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 70
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 35. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%35 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 71
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 36 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%36 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 72
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 36 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%36 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 73
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 37 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%37 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 74
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 37 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%37 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 75
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 38 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%38 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 76
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 38 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%38 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 77
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 39 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%39 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 78
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 39 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3wt%39 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 79
The same preparation method as in example 1 was used except that the dye used in the light-emitting layer was replaced with 40 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%40 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 80
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 40. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3wt%40 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 81
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 41 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%41 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 82
The same preparation method as in example 2 was used, except that the dye used in the light-emitting layer was replaced with 41 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3wt%41 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 83
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 42 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%42 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 84
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 42 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%42 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 85
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 43 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%43 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 86
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 43 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%43 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 87
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 44 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%44 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 88
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 44 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%44 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 89
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 45 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%45 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 90
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 45 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%45 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 91
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 1 to 46. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%46 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 92
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 46 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3wt%46 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 93
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 1 to 47. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%47 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 94
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 47. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%47 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 95
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 1 to 48. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%48 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 96
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 48 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3wt%48 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 97
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 49 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%49 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 98
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 49 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%49 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 99
The same preparation method as in example 1 was used except that the dye used in the light-emitting layer was replaced with 50 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%50 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 100
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 50. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%50 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 101
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 51 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%51 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 102
The same preparation method as in example 2 was used except that the dye used in the light-emitting layer was replaced with 51 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%51 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 103
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 52 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%52 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 104
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 52 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%52 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 105
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 105 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%105 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 106
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 105 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%105 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 107
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 109 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%109 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 108
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 109. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3wt%109 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 109
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 117 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%117 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 110
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 117 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%117 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 111
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 121 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%121 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 112
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 121 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%121 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 113
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 141 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%141 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 114
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 141 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3wt%141 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 115
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 151 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%151 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 116
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 151 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%151 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 117
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 1 to 157. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%157 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 118
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 157. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%157 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 119
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 161 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%161 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 120
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 161 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3wt%161 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 121
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 169 by 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%169 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 122
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 169 by 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%169 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 123
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 173 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%173 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 124
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 173 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%173 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 125
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 193 by 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%193 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 126
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 193 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%193 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 127
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 203 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%203 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 128
The same preparation method as in example 2 was used, except that the dye used in the light-emitting layer was replaced with 203 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%203 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 129
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 209 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%209 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 130
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 209 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%209 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 131
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 213 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%213 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 132
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 213 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%213 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 133
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 1 to 221. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%221 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 134
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 1 to 221. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%221 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 135
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 225 by 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%225 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 136
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 225 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3wt%225 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 137
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 245 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%245 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 138
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 245 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%245 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 139
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 255 by 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%255 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 140
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 255 instead of 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%255 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 141
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 261 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%261 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 142
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 261 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%261 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 143
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 265 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%265 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 144
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 265 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3wt%265 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 145
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 273 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%273 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 146
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 273 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%273 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 147
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 277 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%277 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 148
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 277 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%277 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 149
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 297 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%297 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 150
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 297 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%297 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 151
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 307 by 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%307 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 152
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 307 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%307 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 153
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 417 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%417 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 154
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 417 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%417 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 155
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 1 to 421. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%421 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 156
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 1 to 421. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%421 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 157
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 429 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%429 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 158
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 429 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD: 3wt%429 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 159
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 433 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%433 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 160
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 433 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%433 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 161
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 453 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%453 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 162
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 453 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%453 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 163
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 1 to 463. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%463 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 164
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 463 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%463 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 165
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 469 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%469 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 166
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 469 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%469 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 167
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 473 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%473 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 168
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 473 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%473 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 169
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 481 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%481 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 170
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 481 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%481 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 171
The same preparation method as in example 1 was used except that the dye used in the light-emitting layer was replaced with 485 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%485 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 172
The same preparation method as in example 2 was carried out except that the dye used in the light-emitting layer was replaced with 485 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%485 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 173
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 1 to 505. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%505 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 174
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 505. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%505 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 175
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 1 to 515. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%515 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 176
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 515. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%515 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 177
The same preparation method as in example 1 was used, except that the dye used in the light-emitting layer was replaced with 521 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%521 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 178
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 521. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%521 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 179
The same preparation method as in example 1 was used except that the dye used in the light-emitting layer was replaced with 525 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%525 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 180
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 525 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%525 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 181
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 533 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%533 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 182
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 533 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%533 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 183
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 537 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%537 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 184
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 537 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%537 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 185
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 557 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%557 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 186
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 557 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%557 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 187A
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 567 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%567 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 188
The same preparation method as in example 2 was used except that the dye used in the light-emitting layer was replaced with 567 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%567 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 189
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 729 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%729 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 190
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 729 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%729 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 191
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 733 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%733 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 192
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 733 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%733 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 193
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 741 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%741 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 194
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 741 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%741 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 195
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 745 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%745 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 196
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 745 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%745 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 197
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 765 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%765 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 198
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 765 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%765 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 199
The same procedure as in example 1 was followed except that the dye used in the light-emitting layer was replaced with 1 to 775. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%775 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 200
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 775. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%775 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 201
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 781. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%781 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 202
The same preparation method as in example 2 was used, except that the dye used in the light-emitting layer was replaced with 781. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%781 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 203
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 785 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%785 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 204
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 785 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%785 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 205
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 793 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%793 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 206
The same preparation method as in example 2 was conducted except that the dye used in the light-emitting layer was replaced with 793 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%793 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
EXAMPLE 207
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 797 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host: 3wt%797 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 208
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 797 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%797 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
EXAMPLE 209
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 817 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%817 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 210
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 817 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%817 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 211
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 827 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%827 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 212
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 827 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%827 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 213
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 1 to 833. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%833 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 214
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 1 to 833. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%833 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 215
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 837 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%837 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 216
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 837 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%837 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 217
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 845 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%845 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 218
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 845 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%845 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 219
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 849 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%849 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 220
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 849 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/TD 3wt%849 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 221
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 869 from 1. The device structure is as follows: ITO/HI (10 nm)/HT (30 nm)/EBL (10 nm)/Host 3wt%869 (30 nm)/HBL (10 nm)/ET (30 nm)/LiF (0.5 nm)/Al (150 nm)
Example 222
The same preparation method as in example 2 was repeated except that the dye used in the light-emitting layer was replaced with 869 from 1. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％869(30nm)/HBL(10nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
Example 223
The same preparation method as in example 1 was repeated except that the dye used in the light-emitting layer was replaced with 879 from 1. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％879(30nm)/HBL(10nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
example 224
The same procedure as in example 2 was followed except that the dye used in the light-emitting layer was replaced with 879 from 1. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％879(30nm)/HBL(10nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
comparative device example 1
The same preparation method as device example 1 was carried out, except that compound 1 of the present invention employed in the light-emitting layer was replaced with compound P1 of the prior art, and the specific device structure was as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％P1(30nm)/HBL(10nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
comparative device example 2
The same preparation method as device example 2 was carried out, except that compound 1 of the present invention employed in the light-emitting layer was replaced with compound P1 of the prior art, and the specific device structure was as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％P1(30nm)/HBL(10nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
comparative device example 3
The same preparation method as device example 1 was carried out, except that compound 1 of the present invention employed in the light-emitting layer was replaced with compound P2 of the prior art, and the specific device structure was as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％P2(30nm)/HBL(10nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
comparative device example 4
The same preparation method as device example 2 was carried out, except that compound 1 of the present invention employed in the light-emitting layer was replaced with compound P2 of the prior art, and the specific device structure was as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％P2(30nm)/HBL(10nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
Comparative device example 5
The same preparation method as device example 1 was carried out, except that compound 1 of the present invention employed in the light-emitting layer was replaced with compound P3 of the prior art, and the specific device structure was as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％P3(30nm)/HBL(10nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
comparative device example 6
The same preparation method as device example 2 was carried out, except that compound 1 of the present invention employed in the light-emitting layer was replaced with compound P3 of the prior art, and the specific device structure was as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％P3(30nm)/HBL(10nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
the structural formula of each organic material used in each of the above embodiments is as follows:
specific performance data of the organic electroluminescent devices D1 to D224 and the devices DD1 to DD6 prepared in the above respective examples are shown in table 1.
Table 1:
as can be seen from Table 1 above, when the compound of the present invention is used for a luminescent dye in a luminescent layer of an organic electroluminescent device, the turn-on voltage is less than 3V, the maximum external quantum efficiency is higher than 25%, and the luminance is 1000cd/m 2 When the efficiency roll-off is small, the half-peak width is less than 30nm, and the service life of the LT90 is more than 300h.
Comparative examples 1 and 2 have only one fused carbazole group, and the other carbazole has two benzene rings attached thereto, which reduces structural rigidity, exacerbates non-radiative transition processes due to vibration and rotation, and thus reduces device efficiency and significantly increases half-width. Comparative examples 3 and 4 also have only one fused carbazole group and no sulfur atom is introduced, resulting in slower reverse intersystem leap of the material and slower kinetics of excitons, thus making the device more severely roll-off and reduced device lifetime. But also lack sufficiently large steric hindrance groups to inhibit luminescence quenching due to intermolecular packing, exciton annihilation, and spectral broadening problems, resulting in poor device performance. Comparative examples 5 and 6, which also lack steric hindrance groups, have strong planarity of molecular structure and severe intermolecular packing, resulting in luminescence quenching, exciton annihilation, and spectral broadening. In addition, in the molecular structure, one donor is a condensed heteroaromatic ring derived from diphenylamine, and the structural rigidity is relatively weak, so that the efficiency of the device is reduced, and the half-peak width is increased.
The experimental data show that the general formula compound has the advantages that at least two heteroaromatic rings are fused on the parent nucleus of the BN-type multiple resonance material, at least one of the heteroaromatic rings is a heterocycle containing S, O or Se structurally, the conjugate plane is expanded to realize the red shift of light color, meanwhile, the rigid structure of molecules is maintained, and the strong vibrator strength is favorable for improving the luminous efficiency. And the enhancement of spin-rail coupling effect by introducing S, se heavy atoms is helpful for improving the reverse intersystem jump rate of the MR-TADF, and has smaller efficiency roll-off under high brightness. From half-peak width of electroluminescent spectrum, the embodiment confirms that the material has effective multiple resonance effect, thus greatly enriching the material system and luminescent color range of multiple resonance-thermal activation delayed fluorescence, and having good application prospect.
While the invention has been described in connection with the embodiments, it is not limited to the above embodiments, but it should be understood that various modifications and improvements can be made by those skilled in the art under the guidance of the inventive concept, and the scope of the invention is outlined in the appended claims.
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. While still being apparent from variations or modifications that may be made by those skilled in the art are within the scope of the invention.
Claims (10)
1. A compound of the general formula having the structure shown in formula (i):
in formula (I), ring A 1 Ring A 2 Ring A 3 And ring A 4 Each independently selected from any one of a substituted or unsubstituted C5 to C60 aromatic ring, a substituted or unsubstituted C3 to C60 heteroaromatic ring;
and ring A 1 Ring A 2 Ring A 3 And ring A 4 At least one of which is a substituted or unsubstituted dibenzofive-membered heterocycle, the heteroatom in the five-membered heterocycle being selected from S, O, se or N;
ring A 1 Ring A 2 Ring A 3 And ring A 4 Each of the substituted substituents is independently selected from deuterium, halogen, cyano, nitro, hydroxy, amino, unsubstituted or R 1 Substituted C1-C20 straight or branched alkyl, unsubstituted or R 1 Substituted C3-C20 cycloalkyl, unsubstituted or R 1 Substituted C1-C20 alkoxy, unsubstituted or R 1 Substituted C1-C20 alkylsilyl, unsubstituted or R 1 Substituted C1-C20 alkylamino, unsubstituted or R 1 Substituted C6-C30 arylamino, unsubstituted or R 1 Substituted C3-C30 heteroaryl amino, unsubstituted or R 1 Substituted C6-C30 aryloxy, unsubstituted or R 1 Substituted C3-C30 heteroaryloxy, unsubstituted or R 1 Substituted C6-C60 aryl, unsubstituted or R 1 One of substituted C3-C60 heteroaryl;
and ring A 1 Ring A 2 Ring A 3 And ring A 4 Wherein each of the substituted substituents is independently unconnected, or two adjacent substituents are connected through chemical bonds to form a ring; ring A 1 Ring A 2 Ring A 3 And ring A 4 Wherein each of the substituted substituents is independently unconnected to an adjacent ring structure or is connected to an adjacent ring structure through a chemical bond to form a ring;
the R is 1 Each independently selected from one or a combination of two of halogen, cyano, nitro, hydroxy, amino, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, 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;
the Z is 1 、Z 2 、Z 3 、Z 4 And Z 5 Each independently selected from CR 2 Or N, the R 2 Each independently selected from one or a combination of two of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, 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; and two adjacent R 2 Not connected or by chemical meansThe bonds are connected in a ring.
2. The compound of claim 1, having a structure as shown in formula (1):
ring A 1 Ring A 2 Ring A 3 Ring A 4 、Z 1 、Z 2 、Z 3 、Z 4 And Z 5 The same meaning as expressed in claim 1;
preferably, the ring A 1 Ring A 2 Ring A 3 And ring A 4 One or two of the five-membered heterocyclic rings are substituted or unsubstituted dibenzofive-membered heterocyclic rings, and hetero atoms of the five-membered heterocyclic rings are selected from S, O, se or N;
more preferably, the ring A 1 Ring A 2 Ring A 3 And ring A 4 Is a substituted or unsubstituted dibenzofive-membered heterocycle, the heteroatom of which is selected from S, se or N.
3. The compound of claim 1, having a structure as shown in any one of formulas (1-1) to (1-4):
in the formulae (1-1) to (1-4), the ring A 1 Ring A 2 Ring A 3 Ring A 4 、Z 1 、Z 2 、Z 3 、Z 4 And Z 5 The same meaning as expressed in claim 1;
Y 1 -Y 14 each independently selected from CR 3 Or N, the R 3 Each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, hydroxy, amino, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-toOne or two of C20 alkoxy, C1-C20 alkyl silicon, C1-C20 alkyl amino, C6-C30 aryl amino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl oxy, C6-C60 aryl or C3-C60 heteroaryl; and two adjacent R 3 Are not connected or are connected into a ring through chemical bonds.
4. A compound of formula (la) according to any one of claims 1 to 3, wherein ring a 1 Ring A 2 Ring A 3 Ring A 4 Each independently selected from one of substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzoselenophene, substituted or unsubstituted N-phenylcarbazole, and not both substituted or unsubstituted N-phenylcarbazole;
ring A 1 Ring A 2 Ring A 3 And ring A 4 The substituent groups of the substituent groups are independently selected from deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkyl silicon, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl oxy, C6-C60 aryl and C3-C60 heteroaryl.
5. A compound of the general formula according to any one of claims 1 to 3, having a structure as shown in any one of formulas (2) to (29):
in the general formulae (2) to (29), X 1 And X 2 Each independently selected from S, O, se or N-R c And X is 1 And X 2 Not simultaneously N-R c ，R c Represented as substituted or substituted C 6 -C 30 Aryl or C 3 -C 30 Heteroaryl;
Z 1 、Z 2 、Z 3 、Z 4 and Z 5 The same meaning as expressed in claim 1; y is Y 1 -Y 14 The same meaning as expressed in claim 3;
when R is c When a substituent is present, the substituent groups are each independently selected from one or a combination of two of deuterium, halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, 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, it has a structure as shown in any one of formulas (2), (3), (4), (5), (8), (9), (14), (15), (20), (21), (26) or (28).
6. A compound of formula (la) according to any one of claims 1 to 5, wherein R 1 、R 2 、R 3 Each independently selected from hydrogen, deuterium, deuterated or non-deuterated: 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, anthracenyl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, hole-yl, perylene, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, terphenyl, tripolyphenyl, tetraphenyl, biphenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl Substituted phenyl, tert-butyl substituted phenyl, methyl substituted biphenyl, ethyl substituted biphenyl, isopropyl substituted biphenyl, tert-butyl substituted biphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trildanyl, isothiandenyl, spiroisothiandenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, benzoimidazolyl, and benzoimidazolyl benzimidazolyl, naphthylimidazolyl, phenanthroimidazolyl, pyridmethylimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, benzoxazolyl, naphthyridonezolyl, anthracenooxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetrazolyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, 1, 3-diazolyl, 1,2, 3-diazolyl, 2-diazolyl, 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, (poly) halobenzene, (poly) cyanobenzene or (poly) trifluoromethylbenzene;
R c Selected from deuterated or non-deuterated groups: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyridyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-takenSubstituted biphenyl, ethyl substituted biphenyl, isopropyl substituted biphenyl, tert-butyl substituted biphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridinyl, quinolinyl, isoquinolinyl, acridinyl, pyrazinyl, phenazinyl, azacarbazolyl, phenothiazinyl phenanthrolinyl, benzothiadiazolyl, 9-dimethylacridyl, (poly) halobenzene, (poly) cyanobenzene, (poly) trifluoromethylbenzene;
preferably, R 1 、R 2 、R 3 Each independently selected from hydrogen, deuterium, deuterated or non-deuterated: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl, phenyl, naphthyl, anthryl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, biphenyl, terphenyl, biphenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl Tetrahydropyrene, cis-or trans-indenofluorenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, napthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, enozolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, pyrazinyl, phenazinyl, Phenothiazinyl, azacarbazolyl, phenanthroline, 1,3, 5-triazinyl, benzothiadiazolyl, 9-dimethylacridyl, (poly) halobenzene, (poly) cyanobenzene or (poly) trifluoromethylbenzene.
7. A compound of the general formula according to claim 1, selected from the following specific structural compounds:
8. use of a compound of the general formula according to any one of claims 1 to 7 as a functional material in an organic electronic device comprising an organic electroluminescent device, an optical sensor, a solar cell, an illumination element, an organic thin film transistor, an organic field effect transistor, an information tag, an electronic artificial skin sheet, a sheet scanner or an electronic paper;
preferably, the compounds of the general formula are used as light-emitting layer materials in organic electroluminescent devices.
9. 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, characterized in that at least one compound according to any one of claims 1 to 7 is included in the light-emitting functional layers.
10. The organic electroluminescent device according to claim 9, wherein the light-emitting functional layer comprises a hole-transporting region, a light-emitting layer, and an electron-transporting region, the hole-transporting region is formed on the anode layer, the cathode layer is formed on the electron-transporting region, and the light-emitting layer is formed between the hole-transporting region and the electron-transporting region, wherein the light-emitting layer contains the compound according to any one of claims 1 to 5.
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| CN202211658110.8A CN116253753A (en) | 2022-12-22 | 2022-12-22 | Luminescent material, application thereof and organic electroluminescent device comprising luminescent material |
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