CN110963904A - Compound with ketone and fluorene as cores, preparation method and application thereof - Google Patents
Compound with ketone and fluorene as cores, preparation method and application thereof Download PDFInfo
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- CN110963904A CN110963904A CN201811161092.6A CN201811161092A CN110963904A CN 110963904 A CN110963904 A CN 110963904A CN 201811161092 A CN201811161092 A CN 201811161092A CN 110963904 A CN110963904 A CN 110963904A
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- unsubstituted
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- compound
- ketone
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 83
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- 150000002576 ketones Chemical class 0.000 title claims abstract description 26
- 239000010410 layer Substances 0.000 claims description 76
- 230000000903 blocking effect Effects 0.000 claims description 18
- -1 dimethylfluorenyl group Chemical group 0.000 claims description 15
- 239000002994 raw material Substances 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 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 6
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 6
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- 239000000741 silica gel Substances 0.000 claims description 5
- 229910002027 silica gel Inorganic materials 0.000 claims description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000002346 layers by function Substances 0.000 claims description 4
- 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 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- 238000002390 rotary evaporation Methods 0.000 claims description 3
- 238000005303 weighing Methods 0.000 claims description 3
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000005551 pyridylene group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 12
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 7
- 230000009477 glass transition Effects 0.000 abstract description 6
- 230000002035 prolonged effect Effects 0.000 abstract description 5
- 238000009826 distribution Methods 0.000 abstract description 2
- 239000004065 semiconductor Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 description 86
- 239000007858 starting material Substances 0.000 description 28
- 238000012360 testing method Methods 0.000 description 22
- 238000000921 elemental analysis Methods 0.000 description 21
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 20
- 238000002347 injection Methods 0.000 description 18
- 239000007924 injection Substances 0.000 description 18
- 230000005540 biological transmission Effects 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 239000008204 material by function Substances 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 3
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 3
- 239000007772 electrode material Substances 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000005457 optimization Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- OIIOPWHTJZYKIL-PMACEKPBSA-N (5S)-5-[[[5-[2-chloro-3-[2-chloro-3-[6-methoxy-5-[[[(2S)-5-oxopyrrolidin-2-yl]methylamino]methyl]pyrazin-2-yl]phenyl]phenyl]-3-methoxypyrazin-2-yl]methylamino]methyl]pyrrolidin-2-one Chemical compound C1(=C(N=C(C2=C(C(C3=CC=CC(=C3Cl)C3=NC(OC)=C(N=C3)CNC[C@H]3NC(=O)CC3)=CC=C2)Cl)C=N1)OC)CNC[C@H]1NC(=O)CC1 OIIOPWHTJZYKIL-PMACEKPBSA-N 0.000 description 2
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 2
- NJIAKNWTIVDSDA-FQEVSTJZSA-N 7-[4-(1-methylsulfonylpiperidin-4-yl)phenyl]-n-[[(2s)-morpholin-2-yl]methyl]pyrido[3,4-b]pyrazin-5-amine Chemical compound C1CN(S(=O)(=O)C)CCC1C1=CC=C(C=2N=C(NC[C@H]3OCCNC3)C3=NC=CN=C3C=2)C=C1 NJIAKNWTIVDSDA-FQEVSTJZSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 2
- LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 description 2
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 229940125833 compound 23 Drugs 0.000 description 2
- 229940126545 compound 53 Drugs 0.000 description 2
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- FDBYIYFVSAHJLY-UHFFFAOYSA-N resmetirom Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(=CC=2Cl)N2C(NC(=O)C(C#N)=N2)=O)Cl)=N1 FDBYIYFVSAHJLY-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000009456 molecular mechanism Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
- C07C49/675—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having three rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/06—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D335/16—Oxygen atoms, e.g. thioxanthones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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Abstract
Disclosure of the inventionA compound with ketone and fluorene as cores, a preparation method and application thereof belong to the technical field of semiconductors. The structure of the compound provided by the invention is shown as a general formula (I):
the invention also discloses a preparation method and application of the compound. The structure of the compound is connected with a structure of ketone and fluorene, and the compound has a high triplet state energy level (T1); the chemical stability is improved, and the compound has higher glass transition temperature and molecular thermal stability. In addition, the HOMO and LUMO distribution positions of the compounds of the present invention are separated from each other, so that the compounds have appropriate HOMO and LUMO energy levels. Therefore, after the compound is applied to an OLED device, the luminous efficiency of the device can be effectively improved, and the service life of the device can be effectively prolonged.
Description
Technical Field
The invention relates to a compound taking ketone and fluorene as cores, a preparation method and application thereof, belonging to the technical field of semiconductors.
Background
The Organic Light Emission Diodes (OLED) device technology can be used for manufacturing novel display products and novel lighting products, is expected to replace the existing liquid crystal display and fluorescent lamp lighting, and has a very wide application prospect. The OLED light-emitting device is like a sandwich structure and comprises electrode material film layers and organic functional materials clamped between different electrode film layers, and various different functional materials are mutually overlapped together according to purposes to form the OLED light-emitting device. When voltage is applied to electrodes at two ends of the OLED light-emitting device and positive and negative charges in the organic layer functional material film layer are acted through an electric field, the positive and negative charges are further compounded in the light-emitting layer, and OLED electroluminescence is generated.
Currently, the OLED display technology is already applied in the fields of smart phones, tablet computers, and the like, and is further expanded to the large-size application field of televisions, and the like, but compared with the actual product application requirements, the performance of the OLED device, such as light emitting efficiency, service life, and the like, needs to be further improved. Current research into improving the performance of OLED light emitting devices includes: the driving voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, and the like. In order to realize the continuous improvement of the performance of the OLED device, not only the innovation of the structure and the manufacturing process of the OLED device but also the continuous research and innovation of the photoelectric functional material of the OLED are required to create the functional material of the OLED with higher performance.
The photoelectric functional materials of the OLED applied to the OLED device can be divided into two categories from the aspect of application, namely charge injection transmission materials and luminescent materials. Further, the charge injection transport material may be classified into an electron injection transport material, an electron blocking material, a hole injection transport material, and a hole blocking material, and the light emitting material may be classified into a host light emitting material and a doping material.
In order to fabricate a high-performance OLED light-emitting device, various organic functional materials are required to have good photoelectric properties, for example, as a charge transport material, good carrier mobility, high glass transition temperature, etc. are required, as a host material of a light-emitting layer, good bipolar, appropriate HOMO/LUMO energy level, etc. are required.
The OLED photoelectric functional material film layer for forming the OLED device at least comprises more than two layers of structures, the OLED device structure applied in industry comprises a hole injection layer, a hole transmission layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transmission layer, an electron injection layer and other various film layers, namely the photoelectric functional material applied to the OLED device at least comprises a hole injection material, a hole transmission material, a light emitting material, an electron transmission material and the like, and the material type and the matching form have the characteristics of richness and diversity. In addition, for the collocation of OLED devices with different structures, the used photoelectric functional material has stronger selectivity, and the performance of the same material in the devices with different structures can be completely different.
Therefore, aiming at the industrial application requirements of the current OLED device and the requirements of different functional film layers and photoelectric characteristics of the OLED device, a more suitable OLED functional material or material combination with higher performance needs to be selected to realize the comprehensive characteristics of high efficiency, long service life and low voltage of the device. In terms of the actual demand of the current OLED display lighting industry, the development of the current OLED material is far from enough, and lags behind the requirements of panel manufacturing enterprises, and it is very important to develop a higher-performance organic functional material as a material enterprise.
Disclosure of Invention
An object of the present invention is to provide a compound having a ketone and a fluorene as a core. The compound contains a ketone and fluorene structure, has higher glass transition temperature and molecular thermal stability, proper HOMO and LUMO energy levels and higher Eg, and can effectively improve the photoelectric property of an OLED device and the service life of the OLED device through device structure optimization.
The technical scheme for solving the technical problems is as follows: a compound with ketone and fluorene as core has a structure shown in general formula (1)
A and b are respectively and independently represented as a number 0, 1 or 2;
z is C (R); r represents a hydrogen atom, a cyano group, C1-C10Alkyl of (C)1-C10Alkenyl group of (C)6-C30One of aryl, 5-30 membered heteroaryl containing one or more heteroatoms; and two or more adjacent R's may be bonded to each other to form a ring;
in the general formula (1), X represents-O-, -S-, -C (R)4)(R5) -, or-N (R)6) -one of (a);
l represents a single bond, substituted or unsubstituted C6-C30One of an arylene group of (a), a substituted or unsubstituted 5-30 membered heteroarylene group containing one or more heteroatoms;
R1、R2each independently represents cyano, halogen, C1-C10Alkyl, substituted or unsubstituted C6-C30One of an aryl group, a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms;
R3is represented as C1-C10Alkyl, substituted or unsubstituted C6-C30OfOne of a group, a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms;
R4-R6are each independently represented by C1-C10Alkyl, substituted or unsubstituted C6-C30One of an aryl group, a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms;
the substituent of the substitutable group is selected from cyano, halogen and C1-C10Alkyl of (C)6-C30One or more of aryl and 5-30 membered heteroaryl containing one or more heteroatoms;
the heteroatom is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
The compound of the invention takes ketone as a framework and is connected with a fluorene structure, and the structure is a conjugated rigid structure and has large steric hindrance, so that the compound of the invention has more stable three-dimensional structure. When the compound is used as a hole blocking layer or an electron transport layer material of an OLED, the proper HOMO energy level can effectively realize electron transport; under a proper LUMO energy level, the organic electroluminescent material plays a role in blocking holes, improves the recombination efficiency of excitons in the luminescent layer, reduces energy loss, and enables the energy of the main material of the luminescent layer to be fully transferred to the doped material, thereby improving the luminous efficiency of the material after being applied to a device.
On the basis of the technical scheme, the invention can be further improved as follows.
Further, the L represents one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted naphthyridine group and a substituted or unsubstituted pyridylene group;
r represents one of a hydrogen atom, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a biphenyl group, a furyl group, a thienyl group, a dibenzofuryl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a dibenzothienyl group or a pyridyl group;
the R is1、R2Each independently represents one of a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a biphenyl group, a furyl group, a thienyl group, a dibenzofuryl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a dibenzothienyl group or a pyridyl group;
the R is3Represents one of methyl, ethyl, propyl, isopropyl, tert-butyl, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothienyl and substituted or unsubstituted pyridyl;
the R is4-R6Each independently represents one of methyl, ethyl, propyl, isopropyl, tertiary butyl, amyl, phenyl, naphthyl, biphenyl, terphenyl, naphthyridinyl or pyridyl;
the substituent of the substitutable group is one or more selected from cyano, halogen, methyl, ethyl, propyl, isopropyl, tertiary butyl, amyl, phenyl, naphthyl, biphenyl, terphenyl, naphthyridinyl or pyridyl.
Further, the structure of the compound is shown in any one of general formulas (II-1) to (II-3):
wherein the symbols and indices used have the meanings given above.
Further, the structure of the compound is shown in any one of general formulas (III-1) to (III-17):
wherein the symbols and indices used have the meanings given above.
Further, the structure of the compound is shown as any one of general formulas (IV-1) to (IV-6):
wherein the symbols and indices used have the meanings given above.
Further, when X in the general formula (1) is represented by O, the specific structural formula of the compound is:
When X in the formula (1) represents S, the compound 230-439 is structurally represented by the compounds 1-209, except that X in the formula (1) is changed from O to S;
when X in the formula (1) represents-C (CH)3)(CH3) When-is-the compound 440-649 has a structure as shown in the compounds 1-209 except that X in the formula (1) is changed from O to-C (CH)3)(CH3)-；
When X in the formula (1) represents
When the compound 650-859 has a structure represented by the compounds 1 to 209, except that X in the formula (1) is changed from O to
The second object of the present invention is to provide a method for producing the above-mentioned compound having a ketone and fluorene as cores. The preparation method is simple, has wide market prospect and is suitable for large-scale popularization and application.
The technical scheme for solving the technical problems is as follows: the preparation method of the compound taking the ketone and the fluorene as cores relates to the following reaction equation:
the method comprises the following steps:
weighing raw materials and an intermediate A, and dissolving the raw materials and the intermediate A in a mixed solvent of toluene and ethanol with a volume ratio of 2: 1; adding Na under inert atmosphere2CO3Aqueous solution, Pd (PPh)3)4(ii) a Reacting the mixed solution of the reactants for 10 to 24 hours at the reaction temperature of 95 to 110 ℃, cooling and filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain a product; the molar ratio of the raw material to the intermediate A is 1 (1.0-2.0); na in aqueous solution2CO3The molar ratio of the raw material to the raw material is (1.0-3.0): 1; pd (PPh)3)4The molar ratio to the raw material is (0.006-0.02): 1.
It is a further object of the present invention to provide an organic electroluminescent device. When the compound is applied to an OLED device, high film stability can be kept through device structure optimization, the photoelectric performance of the OLED device and the service life of the OLED device can be effectively improved, and the compound has good application effect and industrialization prospect.
The technical scheme for solving the technical problems is as follows: at least one functional layer of the organic electroluminescent device contains the compound taking the ketone and the fluorene as the core.
On the basis of the technical scheme, the invention can be further improved as follows.
Further, the organic electroluminescent device comprises a hole transport layer or an electron transport layer, and the hole transport layer or the electron transport layer contains the compound with the ketone and the fluorene as the core.
Further, the light-emitting layer contains the compound having the ketone and the fluorene as the core.
The fourth objective of the present invention is to provide an illumination or display device. The organic electroluminescent device can be applied to lighting or display elements, so that the current efficiency, the power efficiency and the external quantum efficiency of the device are greatly improved; meanwhile, the service life of the device is obviously prolonged, and the OLED luminescent device has a good application effect and a good industrialization prospect.
The technical scheme for solving the technical problems is as follows: a lighting or display element includes the above organic electroluminescent device.
The invention has the beneficial effects that:
1. the compound of the invention takes ketone as a framework and is connected with a fluorene structure, and the structure is a conjugated rigid structure and has large steric hindrance, so that the compound of the invention has more stable three-dimensional structure. When the compound is used as a hole blocking layer or an electron transport layer material of an OLED, the proper HOMO energy level can effectively realize electron transport; under a proper LUMO energy level, the organic electroluminescent material plays a role in blocking holes, improves the recombination efficiency of excitons in the luminescent layer, reduces energy loss, and enables the energy of the main material of the luminescent layer to be fully transferred to the doped material, thereby improving the luminous efficiency of the material after being applied to a device.
2. The structure of the compound enables the distribution of electrons and holes in the luminescent layer to be more balanced, and under the proper HOMO energy level, the injection and transmission performance of the electrons is improved; when the material is used as a light-emitting functional layer material of an OLED light-emitting device, the structure matched with the ketone and the fluorene has a higher T1 energy level, so that the exciton utilization rate and the high fluorescence radiation efficiency can be effectively improved, the efficiency roll-off under high current density is reduced, the voltage of the device is reduced, the current efficiency of the device is improved, and the service life of the device is prolonged.
3. The compound has proper evaporation temperature, can keep high film stability through device structure optimization when being applied to an OLED device, can effectively improve the photoelectric property of the OLED device and the service life of the OLED device, and has good application effect and industrialization prospect.
Drawings
FIG. 1 is a schematic structural diagram of the compound of the present invention applied to an OLED device, wherein the components represented by the respective reference numerals are as follows:
1 is a transparent substrate layer, 2 is an ITO anode layer, 3 is a hole injection layer, 4 is a hole transmission or electron blocking layer, 5 is a light-emitting layer, 6 is an electron transmission or hole blocking layer, 7 is an electron injection layer, and 8 is a cathode reflection electrode layer.
FIG. 2 is a graph of current efficiency measured at different temperatures for OLED devices prepared with the compounds of the present invention.
Detailed Description
The principles and features of this invention are described below in conjunction with the following drawings, which are set forth by way of illustration only and are not intended to limit the scope of the invention.
Preparation of intermediate A
Weighing raw material B and dissolving in Tetrahydrofuran (THF) under nitrogen atmosphere, adding bis (pinacolato) diboron, (1, 1' -bis (diphenylphosphino) ferrocene) dichloropalladium (II) and potassium acetate, stirring the mixture, and heating and refluxing the mixed solution of the reactants at the reaction temperature of 70-90 ℃ for 5-10 hours; after the reaction was complete, water was added to cool, and the mixture was filtered and dried in a vacuum oven. Separating and purifying the obtained residue by a silica gel column to obtain an intermediate A;
synthesis of intermediate a1 as an example:
introducing nitrogen into a 250mL three-neck flask, adding 0.02mol of raw material B1 to dissolve in 150mL of tetrahydrofuran, adding 0.024mol of bis (pinacolato) diboron, 0.0002mol of (1, 1' -bis (diphenylphosphino) ferrocene) dichloropalladium (II) and 0.05mol of potassium acetate, stirring the mixture, and heating and refluxing the mixed solution of the reactants at the reaction temperature of 80 ℃ for 5 hours; after the reaction was finished, it was cooled and 100ml of water was added, and the mixture was filtered and dried in a vacuum oven. Separating and purifying the obtained residue by a silica gel column to obtain an intermediate A1; HPLC purity 99.4%, yield 90.3%. Elemental analysis Structure (molecular formula C)37H33BO2): theoretical value: c, 85.38; h, 6.39; b, 2.08; o, 6.15; test values are: c, 85.39; h, 6.40; b, 2.07; and O, 6.14. ESI-MS (M/z) (M)+): theoretical value is 520.48, found 520.46.
Intermediate a was prepared by the synthetic method of intermediate a1, the specific structure is shown in table 1.
TABLE 1
Example 1: preparation of Compound 1
Adding 0.01mol of raw material 1 and 0.015mol of intermediate A1 into a 250ml three-necked bottle, and dissolving the mixture by using a mixed solvent of toluene, ethanol and water in a volume ratio of 2:1: 1; under inert atmosphere, 0.02mol of Na is added2CO3Aqueous solution (2M), 0.0001mol Pd (PPh)3)4(ii) a And (3) reacting the mixed solution of the reactants for 15 hours at the reaction temperature of 100 ℃, cooling and filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain the target product with the HPLC purity of 99.90% and the yield of 76.8%. Elemental analysis Structure (molecular formula C)44H28O2): theoretical value: c, 89.77; h, 4.79; o, 5.44; test values are: c, 89.77; h, 4.78; and O, 5.43. HPLC-MS: the molecular weight of the material is 588.71, and the measured molecular weight is 588.70.
Example 2: preparation of Compound 11
Compound 11 was prepared as in example 1, except starting material 2 was used instead of starting material 1 and intermediate a2 was used instead of intermediate a 1. Elemental analysis Structure (molecular formula C)44H28O2): theoretical value: c, 89.77; h, 4.79; o, 5.44; test values are: c, 89.78; h, 4.77; and O, 5.43. HPLC-MS: the molecular weight of the material is 588.71, and the measured molecular weight is 588.74.
Example 3: preparation of Compound 23
Compound 23 was prepared as in example 1, except starting material 3 was used instead of starting material 1 and intermediate A3 was used instead of intermediate a 1. Elemental analysis Structure (molecular formula C)48H36O2): theoretical value: c, 89.41; h, 5.63; o, 4.96; test values are: c, 89.40; h, 5.63; and O, 4.97. HPLC-MS: the molecular weight of the material is 644.81, and the measured molecular weight is 644.85.
Example 4: preparation of Compound 32
Compound 32 was prepared as in example 1, except starting material 4 was used instead of starting material 1 and intermediate a4 was used instead of intermediate a 1. Elemental analysis Structure (molecular formula C)52H44O2): theoretical value: c, 89.11; h, 6.33; o, 4.57; test values are: c, 89.10; h, 6.34; and O, 4.57. HPLC-MS: the molecular weight of the material is 700.92, and the measured molecular weight is 700.90.
Example 5: preparation of Compound 53
Compound 53 was prepared as in example 1, except starting material 5 was used instead of starting material 1 and intermediate A3 was used instead of intermediate a 1. Elemental analysis Structure (molecular formula C)50H32O2): theoretical value: c, 90.33; h, 4.85; o, 4.81; test values are: c, 90.32; h, 4.85; and O, 4.82. HPLC-MS: the molecular weight of the material is 664.80, and the measured molecular weight is 664.85.
Example 6: preparation of Compound 64
Compound 64 was prepared as in example 1, except starting material 6 was used instead of starting material 1 and intermediate a5 was used instead of intermediate a 1. Elemental analysis Structure (molecular formula C)50H32O2): theoretical value: c, 90.33; h, 4.85; o, 4.81; test values are: c, 90.32; h, 4.85; and O, 4.82. HPLC-MS: the molecular weight of the material is 664.80, and the measured molecular weight is 664.83.
Example 7: preparation of Compound 75
Compound 75 was prepared as in example 1, except starting material 2 was used instead of starting material 1 and intermediate a6 was used instead of intermediate a 1. Elemental analysis Structure (molecular formula C)50H32O2): theoretical value: c, 90.33; h, 4.85; o, 4.81; test values are: c, 90.31; h, 4.86; and O, 4.82. HPLC-MS: the molecular weight of the material is 664.80, and the measured molecular weight is 664.82.
Example 8: preparation of Compound 90
Example 9: preparation of Compound 103
Preparation of Compound 103 is carried outExample 1 except that feed 5 was used instead of feed 1 and intermediate A8 was used instead of intermediate a 1. Elemental analysis Structure (molecular formula C)50H30O2S): theoretical value: c, 86.43; h, 4.35; o, 4.61; s, 4.61; test values are: c, 86.44; h, 4.36; o, 4.60; and S, 4.60. HPLC-MS: the molecular weight of the material is 694.85, and the measured molecular weight is 694.80.
Example 10: preparation of Compound 126
Compound 126 was prepared as in example 1, except intermediate a9 was used in place of intermediate a 1. Elemental analysis Structure (molecular formula C)56H35NO2): theoretical value: c, 89.22; h, 4.68; n, 1.86; o, 4.24; test values are: c, 89.24; h, 4.67; n, 1.85; and O, 4.24. HPLC-MS: the molecular weight of the material is 753.90, and the measured molecular weight is 753.91.
Example 11: preparation of Compound 139
Compound 139 was prepared as in example 1, except starting material 5 was used instead of starting material 1 and intermediate a10 was used instead of intermediate a 1. Elemental analysis Structure (molecular formula C)48H30O2): theoretical value: c, 90.26; h, 4.73; o, 5.01; test values are: c, 90.27; h, 4.73; and O, 5.00. HPLC-MS: the molecular weight of the material is 638.77, and the measured molecular weight is 638.74.
Example 12: preparation of Compound 150
Compound 150 was prepared as in example 1, except starting material 8 was used instead of starting material 1 and intermediate a11 was used instead of intermediate a 1. Elemental analysis Structure (molecular formula C)48H34O4): theoretical value: c, 85.44; h, 5.08; o,948; test values are: c, 85.43; h, 5.08; and O, 9.49. HPLC-MS: the molecular weight of the material is 674.80, and the measured molecular weight is 674.83.
Example 13: preparation of Compound 164
Compound 164 was prepared as in example 1, except starting material 9 was used instead of starting material 1 and intermediate a12 was used instead of intermediate a 1. Elemental analysis Structure (molecular formula C)50H32O2): theoretical value: c, 90.33; h, 4.85; o, 4.81; test values are: c, 90.34; h, 4.84; and O, 4.81. HPLC-MS: the molecular weight of the material is 664.80, and the measured molecular weight is 664.78.
Example 14: preparation of Compound 175
Compound 175 was prepared as in example 1, except intermediate a13 was used instead of intermediate a 1. Elemental analysis Structure (molecular formula C)50H30O3): theoretical value: c, 88.47; h, 4.46; o, 7.07; test values are: c, 88.48; h, 4.46; and O, 7.06. HPLC-MS: the molecular weight of the material is 678.79, and the measured molecular weight is 678.76.
Example 15: preparation of Compound 191
Compound 191 was prepared as in example 1, except starting material 2 was used instead of starting material 1 and intermediate a14 was used instead of intermediate a 1. Elemental analysis Structure (molecular formula C)53H36O2): theoretical value: c, 90.31; h, 5.15; o, 4.54; test values are: c, 90.30; h, 5.15; and O, 4.55. HPLC-MS: the molecular weight of the material is 704.87, and the measured molecular weight is 704.89.
Example 16: preparation of Compound 203
Compound 203 was prepared as in example 1, except intermediate a15 was used in place of intermediate a 1. Elemental analysis Structure (molecular formula C)50H32O2): theoretical value: c, 90.33; h, 4.85; o, 4.81; test values are: c, 90.32; h, 4.86; and O, 4.81. HPLC-MS: the molecular weight of the material is 664.80, and the measured molecular weight is 664.81.
Example 17: preparation of Compound 210
Compound 210 was prepared as in example 1, except starting material 10 was used instead of starting material 1 and intermediate A3 was used instead of intermediate a 1. Elemental analysis Structure (molecular formula C)44H28OS): theoretical value: c, 87.39; h, 4.67; o, 2.65; s, 5.30; test values are: c, 87.40; h, 4.67; o, 2.64; and S, 5.30. HPLC-MS: the molecular weight of the material was 604.77, the measured molecular weight was 604.73.
Example 18: preparation of Compound 223
Compound 223 was prepared as in example 1, except starting material 11 was used instead of starting material 1 and intermediate a2 was used instead of intermediate a 1. Elemental analysis Structure (molecular formula C)50H32OS): theoretical value: c, 88.20; h, 4.74; o, 2.35; s, 4.71; test values are: c, 88.20; h, 4.73; o, 2.35; and S, 4.72. HPLC-MS: the molecular weight of the material is 680.87, and the measured molecular weight is 680.89.
Example 19: preparation of Compound 224
Compound 224 can be prepared as in example 1, except thatFeed 12 replaced feed 1 and intermediate a1 replaced intermediate a 16. Elemental analysis Structure (molecular formula C)53H36O2): theoretical value: c, 90.31; h, 5.15; o, 4.54; test values are: c, 90.32; h, 5.16; and O, 4.52. HPLC-MS: the molecular weight of the material is 704.87, and the measured molecular weight is 704.84.
Example 20: preparation of Compound 225
Compound 225 was prepared as in example 1, except starting material 13 was used instead of starting material 1 and intermediate a4 was used instead of intermediate a 1. Elemental analysis Structure (molecular formula C)50H33NO): theoretical value: c, 90.47; h, 5.01; n, 2.11; o, 2.41; test values are: c, 90.45; h, 5.02; n, 2.12; o, 2.41. HPLC-MS: the molecular weight of the material is 663.82, and the measured molecular weight is 663.85.
The organic compound is used in a light-emitting device, has high Tg (glass transition temperature) temperature and triplet state energy level (T1), and suitable HOMO and LUMO energy levels, and can be used as a hole blocking/electron transporting material and a light-emitting layer material. The thermal performance, T1 energy level and HOMO energy level of the compound of the present invention and the existing material were measured, respectively, and the results are shown in table 2.
TABLE 2
Note: the triplet energy level T1 was measured by Hitachi F-4600 fluorescence spectrometer under the conditions of 2X 10-5A toluene solution of (4); the glass transition temperature Tg is measured by differential scanning calorimetry (DSC, DSC204F1 DSC, Germany Nachi company), the heating rate is 10 ℃/min, and the nitrogen flow is 20 mL/min; the evaporation temperature is reached when the material is evaporated
Temperature at rate; the highest occupied molecular orbital HOMO energy level was tested by the ionization energy test system (IPS-3), which is an atmospheric environment.
The data in the table show that the organic compound has high glass transition temperature and low evaporation temperature, can improve the phase stability of the material film, and further prolongs the service life of the device; the material has high triplet state energy level, and can block energy loss of a light-emitting layer, so that the light-emitting efficiency of the device is improved. Meanwhile, the material and the application material have similar HOMO energy levels. Therefore, after the organic material containing the ketone and the fluorene is applied to different functional layers of an OLED device, the luminous efficiency of the device can be effectively improved, and the service life of the device can be effectively prolonged.
The effect of the compounds of the present invention in the application of OLED devices will now be illustrated by the device examples. Device examples 1 to 20 and device comparative example 1, device examples 2 to 20, and device comparative example 1 were completely the same as device example 1 in terms of the manufacturing process, and the same substrate material and electrode material were used, and the film thickness of the electrode material was also kept the same, except that the hole-blocking, electron-transporting layer material or light-emitting layer material in the device was changed, the composition of each layer of each device is shown in table 3, and the performance test results of each device are shown in tables 4 and 5.
Device example 1
As shown in fig. 1, an electroluminescent device is prepared by the steps of:
a) cleaning the ITO anode layer 2 on the transparent substrate layer 1, respectively ultrasonically cleaning the ITO anode layer 2 with deionized water, acetone and ethanol for 15 minutes, and then treating the ITO anode layer 2 in a plasma cleaner for 2 minutes;
b) evaporating a hole injection layer material HAT-CN on the ITO anode layer 2 in a vacuum evaporation mode, wherein the thickness of the hole injection layer material HAT-CN is 10nm, and the hole injection layer material HAT-CN is used as a hole injection layer 3;
c) evaporating a hole transport material HT-1 with the thickness of 60nm on the hole injection layer 3 in a vacuum evaporation mode, wherein the layer is a hole transport layer 4;
d) on the hole transmission layer 4, an electron blocking layer material EB-1 is evaporated in vacuum, the thickness is 20nm, and the layer is an electron blocking layer 5;
e) a luminescent layer 6 is evaporated on the electron blocking layer 5, the main materials are the compound 1 and the compound GH-1, the doping material is GD-1, the mass ratio of the compound 1 to the GH-1 to the GD-1 is 50:50:10, and the thickness is 30 nm;
f) evaporating electron transport materials ET-1 and Liq on the light emitting layer 6 in a vacuum evaporation mode, wherein the mass ratio of the electron transport materials ET-1 to Liq is 1:1, the thickness of the electron transport materials is 40nm, and the organic material of the layer is used as a hole blocking/electron transport material 7;
g) vacuum evaporating an electron injection layer LiF with the thickness of 1nm on the hole blocking/electron transport layer 7, wherein the layer is an electron injection layer 8;
h) on the electron injection layer 8, cathode Al (100nm) was vacuum-evaporated, and this layer was a cathode reflective electrode layer 9.
After the electroluminescent device was fabricated according to the above procedure, the driving voltage and current efficiency of the device were measured, and the results are shown in table 4. The molecular mechanism formula of the related material is as follows:
TABLE 3
TABLE 4
From the results in table 4, it can be seen that the compound prepared by the present invention and using ketone and fluorene as core can be applied to the fabrication of OLED light emitting device, and compared with the comparative device, the efficiency, voltage and lifetime of the compound are greatly improved compared with the known OLED material, especially the lifetime decay of the device is greatly improved.
In order to compare the efficiency attenuation conditions of different devices under high current density, the efficiency attenuation coefficient phi of each device is defined, wherein phi represents that the driving current is 100mA/cm2The larger the phi value is, the more serious the efficiency roll-off of the device is, and otherwise, the problem of rapid attenuation of the device under high current density is controlled. The efficiency attenuation coefficient phi of the devices obtained in examples 1-20 and comparative example 1 of the device is measured, and the result is shown in table 5:
TABLE 5
| Device embodiments | Coefficient of attenuation of efficiency phi | Device embodiments | Coefficient of attenuation of |
| 1 | 0.21 | 12 | 0.25 |
| 2 | 0.23 | 13 | 0.24 |
| 3 | 0.21 | 14 | 0.26 |
| 4 | 0.22 | 15 | 0.23 |
| 5 | 0.26 | 16 | 0.24 |
| 6 | 0.25 | 17 | 0.20 |
| 7 | 0.23 | 18 | 0.23 |
| 8 | 0.24 | 19 | 0.24 |
| 9 | 0.25 | 20 | 0.23 |
| 10 | 0.23 | 21 | 0.21 |
| 11 | 0.20 | Comparative example 1 | 0.40 |
As can be seen from the data in table 5, the organic light emitting device prepared by using the compound of the present invention has a smaller efficiency decay coefficient, which indicates that the organic light emitting device prepared by using the compound of the present invention can effectively reduce the efficiency roll-off.
The efficiency of the OLED device prepared by the compound is stable when the OLED device works at low temperature, the efficiency of the devices obtained in device examples 1, 12 and 17 and the device comparative example 1 is tested at the temperature of-10-80 ℃, and the obtained results are shown in Table 6 and FIG. 2.
TABLE 6
As can be seen from the data of table 6 and fig. 2, device examples 1, 12 and 17 are device structures in which the compound of the present invention and known materials are combined, and compared to device comparative example 1, not only the low temperature efficiency is high, but also the efficiency is smoothly increased during the temperature increase.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. A compound with ketone and fluorene as cores is characterized in that the structure of the compound is shown as a general formula (1):
a and b are respectively and independently represented as a number 0, 1 or 2;
z representsIs C (R); r represents a hydrogen atom, a cyano group, C1-C10Alkyl of (C)1-C10Alkenyl group of (C)6-C30One of aryl, 5-30 membered heteroaryl containing one or more heteroatoms; and two or more adjacent R's may be bonded to each other to form a ring;
in the general formula (1), X represents-O-, -S-, -C (R)4)(R5) -, or-N (R)6) -one of (a);
l represents a single bond, substituted or unsubstituted C6-C30One of an arylene group of (a), a substituted or unsubstituted 5-30 membered heteroarylene group containing one or more heteroatoms;
R1、R2each independently represents cyano, halogen, C1-C10Alkyl, substituted or unsubstituted C6-C30One of an aryl group, a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms;
R3is represented as C1-C10Alkyl, substituted or unsubstituted C6-C30One of an aryl group, a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms;
R4-R6are each independently represented by C1-C10Alkyl, substituted or unsubstituted C6-C30One of an aryl group, a substituted or unsubstituted 5-30 membered heteroaryl group containing one or more heteroatoms;
the substituent of the substitutable group is selected from cyano, halogen and C1-C10Alkyl of (C)6-C30One or more of aryl and 5-30 membered heteroaryl containing one or more heteroatoms;
the heteroatom is one or more selected from oxygen atom, sulfur atom or nitrogen atom.
2. A ketone and fluorene based compound according to claim 1, wherein L represents one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted naphthyridine group, and a substituted or unsubstituted pyridylene group;
r represents one of a hydrogen atom, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a biphenyl group, a furyl group, a thienyl group, a dibenzofuryl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a dibenzothienyl group or a pyridyl group;
the R is1、R2Each independently represents one of a fluorine atom, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a cyclohexyl group, a phenyl group, a naphthyl group, a biphenyl group, a furyl group, a thienyl group, a dibenzofuryl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a dibenzothienyl group or a pyridyl group;
the R is3Represents one of methyl, ethyl, propyl, isopropyl, tert-butyl, cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothienyl and substituted or unsubstituted pyridyl;
the R is4-R6Each independently represents one of methyl, ethyl, propyl, isopropyl, tertiary butyl, amyl, phenyl, naphthyl, biphenyl, terphenyl, naphthyridinyl or pyridyl;
the substituent of the substitutable group is one or more selected from cyano, halogen, methyl, ethyl, propyl, isopropyl, tertiary butyl, amyl, phenyl, naphthyl, biphenyl, terphenyl, naphthyridinyl or pyridyl.
3. The compound having a ketone and a fluorene as cores according to claim 1, wherein the structure of the compound is represented by any one of general formulae (ii-1) to (ii-3):
wherein the symbols and indices used have the meanings given in claim 1.
4. The compound having a ketone and fluorene as a core according to claim 1, wherein the structure of the compound is represented by any one of general formulae (iii-1) to (iii-17):
wherein the symbols and indices used have the meanings given in claim 1.
5. The compound having a ketone and fluorene as a core according to claim 1, wherein the structure of the compound is represented by any one of general formulae (iv-1) to (iv-6):
wherein the symbols and indices used have the meanings given in claim 1.
6. A ketone and fluorene core compound according to any one of claims 1 to 5, wherein the specific structural formula of the compound is:
7. A process for the preparation of a ketone and fluorene core compound according to any one of claims 1 to 6, wherein the process involves the following reaction equation:
the method comprises the following steps:
weighing raw materials and an intermediate A, and dissolving the raw materials and the intermediate A in a mixed solvent of toluene and ethanol with a volume ratio of 2: 1; adding Na under inert atmosphere2CO3Aqueous solution, Pd (PPh)3)4(ii) a Reacting the mixed solution of the reactants for 10 to 24 hours at the reaction temperature of 95 to 110 ℃, cooling and filtering the reaction solution, carrying out rotary evaporation on the filtrate, and passing through a silica gel column to obtain a product; the molar ratio of the raw material to the intermediate A is 1: 1.0-2.0; na in aqueous solution2CO3The molar ratio of the raw material to the raw material is (1.0-3.0): 1; pd (PPh)3)4The molar ratio to the raw material is (0.006-0.02): 1.
8. An organic electroluminescent device, characterized in that at least one functional layer contains a ketone-and fluorene-based compound according to any one of claims 1 to 6.
9. An organic electroluminescent device according to claim 8, comprising a hole blocking layer, an electron transporting layer or a light-emitting layer, wherein the hole blocking layer, the electron transporting layer or the light-emitting layer contains the ketone and fluorene core compound according to any one of claims 1 to 6.
10. A lighting or display element comprising an organic electroluminescent device as claimed in any one of claims 8 to 9.
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| CN110964021A (en) * | 2018-09-30 | 2020-04-07 | 江苏三月光电科技有限公司 | Compound with fluorene as core, preparation method and application thereof |
| CN111499557A (en) * | 2020-04-23 | 2020-08-07 | 深圳大学 | Organic main body material and electroluminescent device |
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| CN106986814A (en) * | 2017-03-29 | 2017-07-28 | 江苏三月光电科技有限公司 | A kind of compound as core using dimethyl anthrone and its application on organic electroluminescence device |
| CN110386923A (en) * | 2018-04-19 | 2019-10-29 | 北京鼎材科技有限公司 | Carbazole compound and its application and organic electroluminescence device |
| CN110396081A (en) * | 2018-04-24 | 2019-11-01 | 北京鼎材科技有限公司 | Heterocyclic compound and its application and organic electroluminescence device based on carbazole and fluorenes |
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| CN106986814A (en) * | 2017-03-29 | 2017-07-28 | 江苏三月光电科技有限公司 | A kind of compound as core using dimethyl anthrone and its application on organic electroluminescence device |
| CN110386923A (en) * | 2018-04-19 | 2019-10-29 | 北京鼎材科技有限公司 | Carbazole compound and its application and organic electroluminescence device |
| CN110396081A (en) * | 2018-04-24 | 2019-11-01 | 北京鼎材科技有限公司 | Heterocyclic compound and its application and organic electroluminescence device based on carbazole and fluorenes |
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| CN110551135A (en) * | 2018-05-31 | 2019-12-10 | 江苏三月光电科技有限公司 | Compound containing aza five-membered fused ring and application thereof in organic electroluminescent device |
| CN110964021A (en) * | 2018-09-30 | 2020-04-07 | 江苏三月光电科技有限公司 | Compound with fluorene as core, preparation method and application thereof |
| CN111499557A (en) * | 2020-04-23 | 2020-08-07 | 深圳大学 | Organic main body material and electroluminescent device |
| CN111499557B (en) * | 2020-04-23 | 2022-05-31 | 深圳大学 | Organic main body material and electroluminescent device |
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