CN115368390A - Single-boron organic compound as OLED (organic light emitting diode) doping material and organic electroluminescent device comprising same - Google Patents
Single-boron organic compound as OLED (organic light emitting diode) doping material and organic electroluminescent device comprising same Download PDFInfo
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- CN115368390A CN115368390A CN202110556876.4A CN202110556876A CN115368390A CN 115368390 A CN115368390 A CN 115368390A CN 202110556876 A CN202110556876 A CN 202110556876A CN 115368390 A CN115368390 A CN 115368390A
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- 239000000463 material Substances 0.000 title claims abstract description 118
- 229910052796 boron Inorganic materials 0.000 title claims abstract description 20
- -1 boron organic compound Chemical class 0.000 claims abstract description 158
- 125000001424 substituent group Chemical group 0.000 claims abstract description 12
- 239000010410 layer Substances 0.000 claims description 190
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 229910052805 deuterium Inorganic materials 0.000 claims description 27
- 125000004431 deuterium atom Chemical group 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 24
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 239000002019 doping agent Substances 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 13
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 150000005840 aryl radicals Chemical class 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 8
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 7
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 7
- 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 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 125000000468 ketone group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 238000006467 substitution reaction Methods 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 239000002346 layers by function Substances 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000005493 quinolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 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
- 125000006267 biphenyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical class 0.000 claims description 4
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical class C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003914 fluoranthenyl group Chemical class C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 2
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims description 2
- 229960005544 indolocarbazole Drugs 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical class 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical class 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims 7
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 2
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical group C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 claims 1
- 125000005577 anthracene group Chemical class 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical group C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 48
- 238000004770 highest occupied molecular orbital Methods 0.000 abstract description 11
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 abstract description 6
- 230000005855 radiation Effects 0.000 abstract description 6
- 230000007704 transition Effects 0.000 abstract description 6
- 238000006862 quantum yield reaction Methods 0.000 abstract description 4
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 abstract description 3
- 239000004065 semiconductor Substances 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 64
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 238000002347 injection Methods 0.000 description 37
- 239000007924 injection Substances 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000758 substrate Substances 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- 239000010408 film Substances 0.000 description 23
- 230000000903 blocking effect Effects 0.000 description 22
- 239000003480 eluent Substances 0.000 description 21
- 230000005525 hole transport Effects 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000012043 crude product Substances 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 15
- 239000002994 raw material Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000010898 silica gel chromatography Methods 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 238000005259 measurement Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 125000004986 diarylamino group Chemical group 0.000 description 7
- 239000012046 mixed solvent Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMEKEHSRPZAOGO-UHFFFAOYSA-N boron triiodide Chemical compound IB(I)I YMEKEHSRPZAOGO-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 239000012064 sodium phosphate buffer Substances 0.000 description 6
- 238000001771 vacuum deposition Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- 238000007738 vacuum evaporation Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000007772 electrode material Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000010030 laminating Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- GSDQYSSLIKJJOG-UHFFFAOYSA-N 4-chloro-2-(3-chloroanilino)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=CC(Cl)=C1 GSDQYSSLIKJJOG-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 229940125810 compound 20 Drugs 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 3
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical class C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=C1 VOZBMWWMIQGZGM-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- CDEASXIPDPAOGW-UHFFFAOYSA-N bis[4-(9,9-dimethylacridin-10-yl)phenyl]methanone Chemical compound C12=CC=CC=C2N(C2=C(C1(C)C)C=CC=C2)C1=CC=C(C(=O)C2=CC=C(N3C4=CC=CC=C4C(C4=C3C=CC=C4)(C)C)C=C2)C=C1 CDEASXIPDPAOGW-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical group 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 2
- 230000006870 function Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229940058961 hydroxyquinoline derivative for amoebiasis and other protozoal diseases Drugs 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 150000007978 oxazole derivatives Chemical class 0.000 description 2
- 150000005041 phenanthrolines Chemical class 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 239000013598 vector Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- PGJJHMBDWLEWCO-UHFFFAOYSA-N (2-methylpropan-2-yl)oxyboronic acid Chemical compound CC(C)(C)OB(O)O PGJJHMBDWLEWCO-UHFFFAOYSA-N 0.000 description 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical class CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 1
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
- OMDTUSYJJFBYMG-UHFFFAOYSA-N 2,4-bis(9,9-dimethylfluoren-2-yl)-6-naphthalen-2-yl-1,3,5-triazine Chemical compound C1=CC=C2C(C)(C)C3=CC(C=4N=C(N=C(N=4)C=4C=C5C=CC=CC5=CC=4)C4=CC=C5C6=CC=CC=C6C(C5=C4)(C)C)=CC=C3C2=C1 OMDTUSYJJFBYMG-UHFFFAOYSA-N 0.000 description 1
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- SWUBEMMFTUPINB-UHFFFAOYSA-N 9-[3-carbazol-9-yl-5-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]carbazole Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=C(C=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)N2C3=CC=CC=C3C3=CC=CC=C32)=N1 SWUBEMMFTUPINB-UHFFFAOYSA-N 0.000 description 1
- BQFIIADCVFHAKC-UHFFFAOYSA-N 9-[3-carbazol-9-yl-5-[2-phenyl-6-(4-phenylphenyl)pyrimidin-4-yl]phenyl]carbazole Chemical compound C1=CC=CC=C1C1=CC=C(C=2N=C(N=C(C=2)C=2C=C(C=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC=CC=2)C=C1 BQFIIADCVFHAKC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses a single boron organic compound serving as an OLED (organic light emitting diode) doping material and an organic electroluminescent device comprising the same, and belongs to the technical field of semiconductors. The compound provided by the invention has a structure shown in a general formula (1), wherein a substituent group is introduced at a specific position of a boron-nitrogen fused ring parent nucleus, and the spatial position of the compound is limited to torsion of a specific angle, so that the compound has narrow half-peak width, high fluorescence quantum yield, higher radiation transition rate and appropriate HOMO and LUMO energy levels, and can be used as a green light doping material of a light emitting layer of an organic electroluminescent device, thereby improving the light emitting color purity and the service life of the device.
Description
Technical Field
The invention relates to the technical field of semiconductors, in particular to a single boron organic compound serving as an OLED (organic light emitting diode) doping material and an organic electroluminescent device comprising the same.
Background
The traditional fluorescent doping material is limited by the early technology, only 25% singlet excitons formed by electric excitation can emit light, the internal quantum efficiency of the device is low (the highest is 25%), the external quantum efficiency is generally lower than 5%, and the efficiency of the device is far from that of a phosphorescence device. The phosphorescence material enhances intersystem crossing due to strong spin-orbit coupling of heavy atom center, and can effectively utilize singlet excitons and triplet excitons formed by electric excitation to emit light, so that the internal quantum efficiency of the device reaches 100%. However, most phosphorescent materials are limited in application in OLEDs due to problems of high price, poor material stability, poor color purity, severe device efficiency roll-off and the like.
With the advent of the 5G era, higher requirements are put on color development standards, and besides high efficiency and stability, the luminescent material also needs narrower half-peak width to improve the luminescent color purity of the device. The fluorescent doped material can realize high fluorescence quantum and narrow half-peak width through molecular engineering, the blue fluorescent doped material has obtained a staged breakthrough, and the half-peak width of the boron material can be reduced to below 30 nm; the human eye is a more sensitive green light region, and research is mainly focused on phosphorescent doped materials, but the luminescence peak shape of the phosphorescent doped materials is difficult to narrow by a simple method, so that the research on narrow-half-peak-width efficient green fluorescent doped materials has important significance for meeting higher color development standards.
In addition, TADF sensitized fluorescence Technology (TSF) combines TADF material and fluorescent doping material, TADF material is used as exciton sensitization medium, triplet excitons formed by electric excitation are converted into singlet excitons, energy is transferred to the fluorescent doping material through long-range energy transfer of the singlet excitons, and the quantum efficiency in the device can reach 100% as well.
The boron compound with the resonance structure can easily realize narrow half-peak-width luminescence, and the material is applied to the TADF sensitized fluorescence technology and can realize the preparation of devices with high efficiency and narrow half-peak-width emission. As disclosed in CN 107507921A and CN 110492006A, a technique of combining a light-emitting layer using a TADF material having a difference in lowest singlet and lowest triplet levels of 0.2eV or less as a host and a boron-containing material as a dopant; CN110492005A and CN 110492009A disclose a luminescent layer combination scheme using exciplex as a main body and boron-containing material as doping; can realize the efficiency which is comparable with phosphorescence and relatively narrow half-peak width. Therefore, the TADF sensitized fluorescent technology based on the narrow half-peak width boron luminescent material is developed, and has unique advantages and strong potential in the aspect of displaying indexes facing BT.2020.
Disclosure of Invention
In view of the above problems in the prior art, the applicant of the present invention provides a mono-boron organic compound as an OLED doping material, wherein a substituent group is introduced into a specific position of a boron-nitrogen fused ring parent nucleus, and the spatial position of the compound is limited to a twist of a specific angle, so that the compound has a narrow half-peak width, a high fluorescence quantum yield, a high radiation transition rate, and appropriate HOMO and LUMO energy levels, and can be used as a green light doping material of a light emitting layer of an organic electroluminescent device, thereby improving the light emitting color purity and the lifetime of the device.
The technical scheme of the invention is as follows: a monoboron organic compound as a doping material for OLEDs, the monoboron organic compound having the structure of formula (1):
in the general formula (1), R 1 -R 3 Each independently represents cyano, substituted or unsubstituted C 1 -C 10 Chain alkyl group of (1), substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted amino, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 The heteroaryl group of (a);
X 1 -X 3 are each independently represented by C-R 4 ；R 4 Each occurrence being the same or different and being represented by H, deuterium atom, cyano, substituted or unsubstituted C 1 -C 10 Chain alkyl group of (1), substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Alkoxy, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 Heteroaryl, substituted or unsubstituted C 3 -C 30 A ketone group of (a);
R 4 the connection mode with the general formula (1) is single bond substitution or ring combination connection;
the substituents of the above groups which are "substituted or unsubstituted" are optionally selected from deuterium atom, halogen atom, cyano, C 1 ～C 10 Chain alkyl group of (1), C 3 ～C 10 Cycloalkyl of, C 6 ～C 30 Aryl radical, C 2 ～C 30 Any one of heteroaryl;
the hetero atom in the heteroaryl is one or more selected from oxygen, sulfur or nitrogen atoms;
and X 1 、X 2 And X 3 The included angle theta between the plane alpha and the plane beta of the B atom and the two N atoms in the parent nucleus is in the range of 10-40 degrees.
The invention also provides an organic electroluminescent device which comprises a first electrode, a second electrode and an organic luminescent functional layer between the first electrode and the second electrode, wherein the organic luminescent functional layer comprises a luminescent layer, and the luminescent layer contains the single boron organic compound.
The beneficial technical effects of the invention are as follows:
(1) The compound is applied to OLED devices, can be used as a doping material of a luminescent layer material, can emit green fluorescence under the action of an electric field, and can be applied to the field of OLED illumination or OLED display;
(2) The compound has higher fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%;
(3) The compound is used as a doping material, and a TADF sensitizer is introduced as a second main body, so that the efficiency of the device can be effectively improved;
(4) The compound has a narrow spectrum FWHM, and can effectively improve the color gamut of a device and improve the luminous efficiency of the device;
(5) The compound has higher vapor deposition decomposition temperature, can inhibit vapor deposition decomposition of materials, and effectively prolongs the service life of devices.
(6) The compound has higher radiation transition rate and can effectively prolong the service life of a device.
Drawings
FIG. 1 is a schematic structural diagram of an OLED device using the materials listed in the present invention;
wherein, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and features in the embodiments and the embodiments of the present invention may be combined with each other without conflict. The invention is further described with reference to the following drawings and specific examples, which are not intended to be limiting.
In the present invention, HOMO means the highest occupied orbital of a molecule and LUMO means the lowest unoccupied orbital of a molecule, unless otherwise specified. Further, in the present invention, HOMO and LUMO energy levels are expressed in absolute values, and the comparison between the energy levels is also a comparison of the magnitude of the absolute values thereof, and those skilled in the art know that the larger the absolute value of an energy level is, the lower the energy of the energy level is.
In the drawings, the size of layers and regions may be exaggerated for clarity. It will also be understood that when a layer or element is referred to as being "on" another layer or substrate, it can be directly on the other layer or substrate, or intervening layers may also be present. In addition, it will also be understood that when a layer is referred to as being "between" two layers, it can be the only layer between the two layers, or one or more intervening layers may also be present. Like numbers refer to like elements throughout.
In the present invention, when describing electrodes and organic electroluminescent devices, and other structures, terms such as "upper", "lower", "top", and "bottom" used to indicate orientations only indicate orientations in a certain specific state, and do not mean that the related structures can exist only in the orientations; conversely, if the structure is repositioned, e.g., inverted, the orientation of the structure is changed accordingly. Specifically, in the present invention, the "bottom" side of the electrode refers to the side of the electrode that is closer to the substrate during fabrication, while the opposite side away from the substrate is the "top" side.
In the present invention, substituted or unsubstituted C 6 -C 30 Aryl and/or substituted or unsubstituted C 3 -C 30 Heteroaryl means substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted tetracenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenylene, substituted or unsubstituted anthracene, or substituted or unsubstituted phenanthrene
<xnotran> , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , </xnotran>The dibenzothienyl group, the substituted or unsubstituted carbazolyl group, a combination thereof or a fused ring of the combination of the foregoing groups, but is not limited thereto.
C according to the invention 1 -C 10 Chain alkyl (including straight-chain alkyl and branched-chain alkyl) means methyl, ethyl, propyl, isopropyl, butyl, t-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl and the like, but is not limited thereto.
The halogen atom in the present invention refers to a chlorine atom, a fluorine atom, a bromine atom or the like, but is not limited thereto.
C according to the invention 3 -C 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as ring-forming atoms. In this context, preference is given to using C 4 -C 9 Cycloalkyl, more preferably C 5 -C 8 Cycloalkyl, particularly preferably C 5 -C 7 A cycloalkyl group. Non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-dimethylcyclohexyl, adamantyl, cycloheptyl and the like, but are not limited thereto.
A monoboron organic compound represented by general formula (1):
in the general formula (1), R 1 -R 3 Each independently represents cyano, substituted or unsubstituted C 1 -C 10 Chain alkyl group of (1), substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted amino, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 The heteroaryl group of (a);
X 1 -X 3 each independently is represented by C-R 4 ；R 4 Each occurrence being the same or different and being represented by H, deuterium atom, cyano, substituted or unsubstituted C 1 -C 10 Chain alkyl of (2), substituted orUnsubstituted C 1 -C 10 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 Heteroaryl, substituted or unsubstituted C 3 -C 30 A ketone group of (a);
R 4 the connection mode with the general formula (1) is single bond substitution or ring combination connection;
the substituents of the above groups which are "substituted or unsubstituted" are optionally selected from deuterium atom, halogen atom, cyano, C 1 ～C 10 Chain alkyl group of (1), C 3 ～C 10 Cycloalkyl of, C 6 ～C 30 Aryl radical, C 2 ～C 30 Any one of heteroaryl;
the hetero atom in the heteroaryl is one or more selected from oxygen, sulfur or nitrogen atoms;
and X 1 、X 2 And X 3 The included angle theta between the plane alpha and the plane beta of the B atom and the two N atoms in the parent nucleus is in the range of 10-40 degrees.
Preferred embodiment, X 1 、X 2 、X 3 The angle theta between the plane alpha and the plane beta of the parent nucleus in which the B atom and the two N atoms lie is in the range of 20 degrees to 35 degrees, more preferably in the range of 25 degrees to 30 degrees.
Preferably, the structure of the monoboron organic compound is shown in any one of general formula (2) to general formula (5):
in the general formula (2) -the general formula (5), R 1 -R 3 Each independently represents a deuterium atom, a cyano group, a substituted or unsubstituted C 1 -C 10 Chain alkyl group of (1), substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted amino, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 Of (2)A group;
z is independently at each occurrence represented by C-R 5 ；R 5 Each occurrence being the same or different and being represented by H, deuterium atom, cyano, substituted or unsubstituted C 1 -C 10 Chain alkyl group of (1), substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 The heteroaryl group of (a);
the substituent of the above group which is "substituted or unsubstituted" is optionally selected from deuterium atom, halogen atom, cyano group, C 1 ～C 10 Chain alkyl group of (1), C 3 ～C 10 Cycloalkyl of (C) 6 ～C 30 Aryl radical, C 2 ～C 30 Any one of heteroaryl;
the hetero atoms in the heteroaryl group are selected from one or more of oxygen, sulfur or nitrogen atoms.
Preferably, the structure of the monoboron organic compound is shown as the general formula (6):
in the general formula (6), R 1 -R 3 Each independently represents a deuterium atom, a cyano group, a substituted or unsubstituted C 1 -C 10 Chain alkyl group of (1), substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted amino, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 The heteroaryl group of (a);
R 4 represented by H, a deuterium atom, a cyano group, a substituted or unsubstituted C 1 -C 10 Chain alkyl group of (1), substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Alkoxy, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 Heteroaryl, substituted or unsubstituted C 3 -C 30 Ketone group of；
The substituents of the above groups which are "substituted or unsubstituted" are optionally selected from deuterium atom, halogen atom, cyano, C 1 ～C 10 Chain alkyl group of (1), C 3 ～C 10 Cycloalkyl of, C 6 ～C 30 Aryl radical, C 2 ～C 30 Any one of heteroaryl;
the hetero atom in the heteroaryl is one or more selected from oxygen, sulfur or nitrogen atom.
In a preferred embodiment, the R group 1 -R 3 Each independently represents a deuterium atom, a cyano group, an adamantyl group, a methyl group, a trifluoromethyl group, an ethyl group, an isopropyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenylyl group, a deuterated biphenylyl group, a terphenylyl group, a diphenylether group, a methyl-substituted diphenylether group, a naphthyl group, an anthryl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9, 9-dimethylfluorenyl group, a phenyl-substituted amino group, a tert-butyl-substituted dibenzofuryl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenylyl group, an ethyl-substituted biphenylyl group, an isopropyl-substituted biphenylyl group, a tert-butyl-substituted biphenylyl group, a phenyl-substituted tert-butyl group, a xanthenyl group, a phenyl-substituted triazinyl group, a phenyl-substituted boryl group, a methoxy group, a tert-butoxy group;
the R is 4 Represented by H, deuterium atom, cyano group, adamantyl group, methyl group, trifluoromethyl group, ethyl group, isopropyl group, isobutyl group, tert-butyl group, cyclopentyl group, methyl-substituted cyclopentyl group, cyclohexyl group, phenyl group, deuterated phenyl group, phenylbenzofuran pyridine, biphenyl group, deuterated biphenyl group, terphenyl group, diphenyl ether group, methyl-substituted diphenyl ether group, benzophenone group, xanthenone group, naphthyl group, anthryl group, phenanthryl group, indenyl group, pyridazinyl group, pyrazinyl group, pyridyl group, phenyl-substituted pyridyl group, pyrimidinyl group, phenyl-substituted pyrimidinyl group, fluoranthenyl groupDihydroacenaphthenyl, quinolyl, isoquinoline, phenylisoquinolyl, furyl, phenanthridinyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, phenylbenzimidazolyl, benzodioxinyl, phenylphenanthridinyl, benzofuropyrimidinyl, N-phenylcarbazolyl, indolocarbazole, 9-dimethylfluorenyl, spirofluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuryl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenylyl, ethyl-substituted biphenylyl, isopropyl-substituted biphenylyl, tert-butyl-substituted biphenylyl, phenyl-substituted tert-butyl, xanthenone, phenyl-substituted triazinyl, dibenzofuryl-substituted triazinyl, carbazolyl-substituted triazinyl, dibenzofuran-phenyl-triazinyl, indolocarbazole-phenyl-triazinyl, methoxy, tert-butoxy; r 4 The connection mode with the general formula (1) is single bond substitution or ring combination connection.
In a preferred embodiment, the R group 5 Represented by H, deuterium atom, cyano group, adamantyl group, methyl group, trifluoromethyl group, ethyl group, isopropyl group, isobutyl group, tert-butyl group, cyclopentyl group, methyl-substituted cyclopentyl group, cyclohexyl group, phenyl group, deuterated phenyl group, biphenylyl group, deuterated biphenylyl group, terphenylyl group, diphenylether group, methyl-substituted diphenylether group, naphthyl group, anthracenyl group, phenanthryl group, pyridyl group, phenyl-substituted pyridyl group, pyrimidinyl group, phenyl-substituted pyrimidinyl group, quinolyl group, furyl group, thienyl group, benzofuryl group, dibenzofuryl group, dibenzothienyl group, carbazolyl group, N-phenylcarbazolyl group, 9-dimethylfluorenyl group, spirofluorenyl group, phenyl-substituted amino group, tert-butyl-substituted dibenzofuryl group, methyl-substituted phenyl group, ethyl-substituted phenyl group, isopropyl-substituted phenyl group, tert-butyl-substituted phenyl group, methyl-substituted biphenylyl group, ethyl-substituted biphenylyl group, isopropyl-substituted biphenylyl group, tert-butyl-substituted biphenylyl group, phenyl-substituted tert-butyl group, xanthenyl group, phenyl-substituted triazinyl group, phenyl-substituted boryl group, methoxy group, tert-butoxy group.
In a preferred embodiment, the R group 1 And R 2 Each independently represents methyl, isopropyl, tert-butyl or phenyl; r is 3 Represented by phenyl, methyl, isopropyl, tert-butyl, trifluoromethyl or cyano.
In a preferred embodiment, the R 1 And R 2 Identically represented by methyl, isopropyl, tert-butyl or phenyl; r 3 Expressed as phenyl, methyl, isopropyl, tert-butyl, trifluoromethyl or cyano.
In a preferred embodiment, the R group 1 And R 2 Identically expressed as tert-butyl; r 3 Expressed as phenyl, methyl, isopropyl, tert-butyl, trifluoromethyl, cyano.
In a preferred embodiment, the R group 1 And R 2 Each independently represents methyl, isopropyl, tert-butyl or phenyl, R 3 Is represented by phenyl, methyl, isopropyl, tert-butyl, trifluoromethyl or cyano, and R4 is represented by phenyl or tert-butyl substituted phenyl.
Preferably, the structure of the monoboron organic compound is shown as the general formula (7):
in the general formula (7), X 1 -X 3 Are each independently represented by C-R 4 ；R 4 Each occurrence being the same or different and being represented by H, deuterium atom, cyano, substituted or unsubstituted C 1 -C 10 Chain alkyl group of (1), substituted or unsubstituted C 1 -C 10 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 Heteroaryl, substituted or unsubstituted C 3 -C 30 A ketone group of (a);
R 4 the connection mode with the general formula (7) is single bond substitution or ring combination connection;
the substituents of the "substituted or unsubstituted" radicals mentioned above are optionally selected fromDeuterium atom, halogen atom, cyano group, C 1 ～C 10 Chain alkyl group of (1), C 3 ～C 10 Cycloalkyl of, C 6 ～C 30 Aryl radical, C 2 ～C 30 Any one of heteroaryl;
the hetero atom in the heteroaryl is one or more selected from oxygen, sulfur or nitrogen atoms;
and X 1 、X 2 And X 3 The included angle theta between the plane alpha and the plane beta of the B atom and the two N atoms in the mother nucleus is in the range of 10-40 degrees.
Preferably, the structure of the monoboron organic compound is shown as a general formula (8):
in the general formula (8), R 4 Each occurrence being the same or different and being represented by H, deuterium atom, cyano, substituted or unsubstituted C 1 -C 10 Chain alkyl group of (1), substituted or unsubstituted C 1 -C 10 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 Heteroaryl, substituted or unsubstituted C 3 -C 30 A ketone group of (a);
R 4 the connection mode with the general formula (8) is single bond substitution;
the substituent of the above group which is "substituted or unsubstituted" is optionally selected from deuterium atom, halogen atom, cyano group, C 1 ～C 10 Chain alkyl group of (1), C 3 ～C 10 Cycloalkyl of, C 6 ～C 30 Aryl radical, C 2 ～C 30 Any one of heteroaryl;
the hetero atom in the heteroaryl is one or more selected from oxygen, sulfur or nitrogen atom.
Preferably, the specific structural formula of the monoboron organic compound is any one of the following structures:
organic electroluminescent device
The invention provides an organic electroluminescent device, which comprises a first electrode, a second electrode and an organic light-emitting functional layer between the first electrode and the second electrode, wherein the organic light-emitting functional layer comprises a light-emitting layer, and the light-emitting layer contains a single boron organic compound shown in a general formula (1).
In a preferred embodiment of the present invention, the light-emitting layer comprises a host material and a dopant material containing a monoboron organic compound described by general formula (1).
In a preferred embodiment of the present invention, the light-emitting layer includes a first host material, a second host material, and a dopant material, at least one of the first host material and the second host material is a TADF material, and the dopant material is a monoboron organic compound described by general formula (1).
In a preferred embodiment of the present invention, there is provided an organic electroluminescent device comprising a substrate, an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode layer, wherein the anode is on the substrate, the hole injection layer is on the anode, the hole transport layer is on the hole injection layer, the electron blocking layer is on the hole transport layer, the light emitting layer is on the hole transport layer, the electron transport layer is on the light emitting layer, the electron injection layer is on the electron transport layer and the cathode layer is on the electron injection layer.
Fig. 1 is a schematic structural diagram of the compound of the present invention applied to an OLED device, where 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer.
As the substrate of the organic electroluminescent device of the present invention, any substrate commonly used for organic electroluminescent devices can be used. Examples are transparent substrates, such as glass or transparent plastic substrates; opaque substrates, such as silicon substrates; flexible PI film substrate. Different substrates have different mechanical strength, thermal stability, transparency, surface smoothness, water resistance. The direction of use varies depending on the nature of the substrate. In the present invention, a transparent substrate is preferably used. The thickness of the substrate is not particularly limited.
A first electrode is formed on the substrate, and the first electrode and the second electrode may be opposite to each other. The first electrode may be an anode. The first electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode is a transmissive electrode, it may be formed using a transparent metal oxide, such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), zinc oxide (ZnO), indium Tin Zinc Oxide (ITZO), or the like. When the first electrode is a semi-transmissive electrode or a reflective electrode, it may include Ag, mg, al, pt, pd, au, ni, nd, ir, cr, or a metal mixture. The thickness of the first electrode layer depends on the material used and is typically 50-500nm, preferably 70-300nm and more preferably 100-200nm.
The organic functional material layer arranged between the first electrode and the second electrode sequentially comprises a hole transport region, a light emitting layer and an electron transport region from bottom to top.
Herein, the hole transport region constituting the organic electroluminescent device may be exemplified by a hole injection layer, a hole transport layer, an electron blocking layer, and the like.
As the materials of the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be selected from known materials used in OLED devices.
Examples of the above-mentioned materials may be phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridinoline derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quinone derivatives, styrylanthracene derivatives, styrylamine derivatives and like styrene compounds, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline-based copolymers, porphyrin compounds, carbazole derivatives, polyarylalkane derivatives, polyphenylene ethylene and derivatives thereof, polythiophene and derivatives thereof, conductive polymer oligomers such as poly-N-vinylcarbazole derivatives and thiophene oligomers, aromatic tertiary amine compounds, styrene amine compounds, triamines, tetraamines, benzidines, propyne diamine derivatives, p-phenylenediamine derivatives, m-phenylenediamine derivatives, 1 '-bis (4-diarylaminophenyl) cyclohexane, 4' -bis (diarylamine) biphenyls, and the like bis [4- (diarylamino) phenyl ] methanes, 4 '-bis (diarylamino) terphenyls, 4' -bis (diarylamino) quaterphenyls, 4 '-bis (diarylamino) diphenyl ethers, 4' -bis (diarylamino) diphenylsulfanes, bis [4- (diarylamino) phenyl ] dimethylmethanes, bis [4- (diarylamino) phenyl ] -bis (trifluoromethyl) methanes, 2-diphenylethylene compounds, and the like.
Furthermore, according to the matching requirements of the devices, the hole transport film layer between the hole transport auxiliary layer and the hole injection layer of the organic electroluminescent device can be a single film layer or a superposition structure of a plurality of hole transport materials. In this context, the film thickness of the hole carrier conducting film layer having the above-described various functions is not particularly limited.
The hole injection layer comprises a host organic material that conducts holes and also comprises a P-type dopant material with a deep HOMO level (and correspondingly a deep LUMO level). Based on empirical summary, in order to achieve smooth injection of holes from the anode to the organic film layer, the HOMO level of the host organic material used for the anode interface buffer layer to conduct holes must have certain characteristics with the P-doped material, so that the generation of a charge transfer state between the host material and the doped material is expected to be realized, ohmic contact between the buffer layer and the anode is realized, and efficient injection from the electrode to hole injection conduction is realized.
In view of the above empirical summary, for the hole host materials with different HOMO levels, different P-doped materials need to be selected and matched to realize ohmic contact of the interface, so as to improve the hole injection effect.
Thus, in one embodiment of the present invention, for better hole injection, the hole injection layer further comprises a P-type dopant material having charge conductivity selected from the group consisting of: quinone derivatives such as Tetracyanoquinodimethane (TCNQ) and 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives such as 2,3,6,7,10, 11-hexacyano-1, 4,5,8,9, 12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives such as 4,4',4"- ((1E, 1' E) -cyclopropane-1, 2, 3-trimethylenetri (cyanoformylidene)) tris (2, 3,5, 6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.
In the hole injection layer of the present invention, the ratio of the hole transport material to the P-type dopant material used is 99.
The thickness of the hole injection layer of the present invention may be 5 to 100nm, preferably 5 to 50nm and more preferably 5 to 20nm, but the thickness is not limited to this range.
The thickness of the hole transport layer of the present invention may be 5 to 200nm, preferably 10 to 150nm and more preferably 20 to 100nm, but the thickness is not limited to this range.
The thickness of the electron blocking layer of the present invention may be 1 to 20nm, preferably 5 to 10nm, but the thickness is not limited to this range.
After the hole injection layer, the hole transport layer, and the electron blocking layer are formed, a corresponding light emitting layer is formed over the electron blocking layer.
The light emitting layer may include a host material that may use a green host material commonly used in the art and a dopant material that uses a monoboron organic compound represented by the general formula (1) of the present invention.
In the light-emitting layer of the present invention, the ratio of the host material to the dopant material used is 99.
The thickness of the light emitting layer may be adjusted to optimize light emitting efficiency and driving voltage. A preferable range of the thickness is 5nm to 50nm, further preferably 10 to 50nm, and more preferably 15 to 30nm, but the thickness is not limited to this range.
In the present invention, the electron transport region may include, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer disposed over the light emitting layer, in this order, but is not limited thereto.
The hole blocking layer is a layer that blocks holes injected from the anode from passing through the light emitting layer to the cathode, thereby extending the lifetime of the device and improving the performance of the device. The hole blocking layer of the present invention may be disposed over the light emitting layer. As the hole-blocking layer material of the organic electroluminescent device of the present invention, compounds having a hole-blocking effect known in the art, for example, phenanthroline derivatives such as bathocuproine (referred to as BCP), metal complexes of hydroxyquinoline derivatives such as aluminum (III) bis (2-methyl-8-quinoline) -4-phenylphenolate (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, and 9,9'- (5- (6- ([ 1,1' -biphenyl ] derivatives)]-4-yl) -2-phenylpyrimidin-4-yl) -1, 3-phenylene) bis (9H-carbazole) (CAS No.:1345338-69-3) And pyrimidine derivatives. The thickness of the hole blocking layer of the present invention may be 2 to 200nm, preferably 5 to 150nm, and more preferably 10 to 100nm, but the thickness is not limited to this range.
The electron transport layer may be disposed over the light-emitting layer or, if present, the hole blocking layer. The electron transport layer material is a material that easily receives electrons of the cathode and transfers the received electrons to the light emitting layer. Materials with high electron mobility are preferred. As the electron transport layer of the organic electroluminescent device of the present invention, an electron transport layer material for organic electroluminescent devices known in the art, for example, in Alq, can be used 3 Metal complexes of hydroxyquinoline derivatives represented by BAlq and Liq, various rare earth metal complexes, triazole derivatives, triazine derivatives such as 2, 4-bis (9, 9-dimethyl-9H-fluoren-2-yl) -6- (naphthalen-2-yl) -1,3, 5-triazine (CAS No.: 1459162-51-6), 2- (4- (9, 10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [ d]Imidazole derivatives such as imidazole (CAS number: 561064-11-7, commonly known as LG 201), oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silicon-based compound derivatives, and the like. The thickness of the electron transport layer of the present invention may be 10 to 80nm, preferably 20 to 60nm, and more preferably 25 to 45nm, but the thickness is not limited to this range.
The electron injection layer may be disposed over the electron transport layer. The electron injection layer material is generally a material preferably having a low work function so that electrons are easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, electron injection layer materials for organic electroluminescent devices known in the art, for example, lithium; lithium salts such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate or lithium azide; or cesium salts, cesium fluoride, cesium carbonate or cesium azide. The thickness of the electron injection layer of the present invention may be 0.1 to 5nm, preferably 0.5 to 3nm, and more preferably 0.8 to 1.5nm, but the thickness is not limited to this range.
The second electrode may be disposed over the electron transport region. The second electrode may be a cathode. The second electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode may comprise, for example, li, yb, ca, liF/Al, mg, baF, ba, ag, or compounds or mixtures thereof; when the second electrode is a semi-transmissive electrode or a reflective electrode, the second electrode may include Ag, mg, yb, al, pt, pd, au, ni, nd, ir, cr, li, ca, liF/Al, mo, ti, or a compound or mixture thereof, but is not limited thereto. The thickness of the cathode depends on the material used and is generally from 10 to 50nm, preferably from 15 to 20nm.
The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign substances such as moisture and oxygen from entering the organic layers of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass or metal can; or a thin film covering the entire surface of the organic layer.
Preparation method of organic electroluminescent device
The present invention also relates to a method of manufacturing the above organic electroluminescent device, which comprises sequentially laminating a first electrode, a plurality of organic thin film layers, and a second electrode on a substrate. The multilayer organic thin film layer is formed by sequentially laminating a hole transport region, a light emitting layer and an electron transport region from bottom to top on the first electrode, wherein the hole transport region is formed by sequentially laminating a hole injection layer, a hole transport layer and an electron blocking layer from bottom to top on the first electrode, and the electron transport region is formed by sequentially laminating a hole blocking layer, an electron transport layer and an electron injection layer from bottom to top on the light emitting layer. In addition, optionally, a CPL layer may be further laminated on the second electrode to improve the light extraction efficiency of the organic electroluminescent device.
As for the lamination, a method of vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, LITI, or the like may be used, but is not limited thereto. Vacuum evaporation, among others, means heating and plating a material onto a substrate in a vacuum environment.
In the present invention, it is preferable to form the respective layers using a vacuum evaporation method, wherein the temperature of about 100-500 ℃ can be controlled at about 10- 8 -10- 2 Vacuum degree of tray and its combination
Vacuum evaporation at a rate of (2). The degree of vacuum is preferably 10- 6 -10- 2 Torr, more preferably 10- 5 -10- 3 And (5) Torr. The rate is about
More preferably about
The material for forming each layer according to the present invention may be used as a single layer by forming a film alone, may be used as a single layer by forming a film in admixture with another material, or may be used as a laminated structure of layers formed alone, layers formed in admixture with each other, or a laminated structure of layers formed alone and layers formed in admixture with each other.
The following examples are intended to better illustrate the invention, but the scope of the invention is not limited thereto.
The raw materials involved in the synthetic examples of the present invention are either commercially available or prepared by conventional preparation methods in the art;
example 1 synthesis of compound 1:
(1) Preparation of intermediate a-1:
in a three-necked flask, under the protection of argon, 0.893mmol of the starting material A-1,2.239mmol of methyl boric acid, 3.58mmol of potassium phosphate, 0.045mmol of Pd (OAc) 2 0.091mmol Mephos, followed by the addition of 10mL toluene/water solution (toluene: water =3: 1), heated to 100 ℃ for 48 hours; naturally cooled to room temperature, filtered, and the filtrate was subjected to reduced pressure rotary evaporation, and the crude product was purified by silica gel column chromatography (eluent: PE: DCM = 5). LC-MS: measurement value: 294.05 ([ M + H ]] + ) The theoretical value is as follows: 293.21.
(2) Preparation of intermediate b-1:
introducing nitrogen to protect, adding 0.90mmol of raw material B-1,2.70mmol of intermediate a-1,5.20mmol of K 2 CO 3 And 20mL of DMF were added to a three-necked flask, which was then heated to 110 ℃. After stirring for 3 hours, the reaction mixture was cooled to room temperature, the reaction mixture was poured into a large amount of MeOH to give a precipitate, after filtration, the resulting solid was washed with MeOH, and the resulting filtrate was evaporated in vacuo. The obtained residue was purified by silica gel column chromatography (eluent: PE: DCM = 5.LC-MS: measurement value: 661.26 ([ M + H ]] + ) The theoretical value is as follows: 660.44.
(3) Preparation of compound 1:
in a three-necked flask, 2.20mmol of boron triiodide and 1.10mmol of intermediate b-1 were dissolved in 30mL of 1,2, 4-trichlorobenzene under nitrogen protection. After stirring at 180 ℃ for 20 hours, the reaction mixture was diluted with dichloromethane (50 mL) and 100mL of ph =6 sodium phosphate buffer solution was added at 0 ℃, the aqueous layer was separated and dichloromethane (1)00mL, three times). The crude product was chromatographed over a silica gel column (eluent: hexane/CH) 2 Cl 2 = 5/1) purification to give the target compound 1.
Example 2 synthesis of compound 4:
(1) Preparation of intermediate a-2:
in a three-necked flask, under the protection of argon, 0.893mmol of the starting material A-1,2.239mmol of tert-butyl boric acid, 3.58mmol of potassium phosphate, 0.045mmol of Pd (OAc) 2 0.091mmol Mephos, followed by the addition of 10mL toluene/water solution (toluene: water =3: 1), heated to 100 ℃ for 49 hours; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated under reduced pressure, and the crude product was purified by silica gel column chromatography (eluent: PE: DCM = 5) to give an intermediate a-2.LC-MS: measurement value: 336.18 ([ M + H)] + ) The theoretical value is as follows: 335.26.
(2) Preparation of intermediate b-2:
introducing nitrogen to protect, adding 0.90mmol of raw material B-1,2.70mmol of intermediate a-2,5.20mmol of K 2 CO 3 And 20mL of DMF were added to a three-necked flask, which was then heated to 110 ℃. After stirring for 4 hours, the reaction mixture was cooled to room temperature, the reaction mixture was poured into a large amount of MeOH to give a precipitate, after filtration, the resulting solid was washed with MeOH, and the resulting filtrate was evaporated in vacuo. The obtained residue was purified by silica gel column chromatography (eluent: PE: DCM = 5.LC-MS: measurement value: 745.48 ([ M + H)] + ) The theoretical value is as follows: 744.54.
(3) Preparation of compound 4:
in a three-necked flask, 2.20mmol of boron triiodide and 1.10mmol of intermediate b-2 were dissolved in 30mL of 1,2, 4-trichlorobenzene under nitrogen protection. After stirring at 180 ℃ for 22 hours, the reaction mixture was diluted with dichloromethane (50 mL) and 100mL of ph =6 sodium phosphate buffer was added at 0 ℃, the aqueous layer was separated and extracted with dichloromethane (100 mL, three times). The crude product was chromatographed on a silica gel column (eluent: hexane/CH) 2 Cl 2 And (= 5/1) to obtain the target compound 4.
Example 3 synthesis of compound 20:
(1) Preparation of intermediate a-3:
introducing nitrogen gas for protection, adding 10.0mmol of raw material A-2 and 36.0mmol of raw material C-1 into a three-neck bottle, dissolving with mixed solvent (90 ml of toluene and 45ml of ethanol), and adding 0.1mmol of Pd (PPh) 3 ) 4 3mol/L of K 2 CO 3 15mL of the aqueous solution was heated under reflux for 12 hours. The spot plate was sampled to confirm completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a pad of celite, rinsing with chloroform, and the resulting filtrate was evaporated in vacuo. The crude product was purified by silica gel column chromatography (eluent: PE: DCM = 5) to give intermediate a-3.LC-MS: measurement value: 396.20 ([ M + H ]] + ) The theoretical value is as follows: 395.17.
(2) Preparation of intermediate b-3:
introducing nitrogen to protect, adding 0.90mmol of raw material B-1,2.70mmol of intermediate a-3,5.20mmol of K 2 CO 3 And 20mL of DMF were added to a three-necked flask, which was then heated to 110 ℃. After stirring for 6 hours, the reaction mixture was cooled to room temperature, the reaction mixture was poured into a large amount of MeOH to give a precipitate, after filtration, the resulting solid was washed with MeOH, and the resulting filtrate was evaporated in vacuo. Passing the obtained residue through siliconPurification by gel column chromatography (eluent: PE: DCM = 5) gave intermediate b-3.LC-MS: measurement value: 865.19 ([ M + H)] + ) The theoretical value is as follows: 864.35.
(3) Preparation of compound 20:
in a three-necked flask, 2.20mmol of boron triiodide and 1.10mmol of intermediate b-3 were dissolved in 30mL of 1,2, 4-trichlorobenzene under nitrogen protection. After stirring at 180 ℃ for 23 hours, the reaction mixture was diluted with dichloromethane (50 mL) and 100mL of ph =6 sodium phosphate buffer solution was added at 0 ℃, the aqueous layer was separated and extracted with dichloromethane (100 mL, three times). The crude product was chromatographed over a silica gel column (eluent: hexane/CH) 2 Cl 2 = 5/1) purification to give the target compound 20.
Example 4 synthesis of compound 64:
(1) Preparation of intermediate b-4:
introducing nitrogen to protect, adding 0.90mmol of raw material B-2,2.70mmol of intermediate a-1,5.20mmol of K 2 CO 3 And 20mL of DMF were added to a three-necked flask, which was then heated to 110 ℃. After stirring for 3 hours, the reaction mixture was cooled to room temperature, the reaction mixture was poured into a large amount of MeOH to give a precipitate, after filtration, the resulting solid was washed with MeOH, and the resulting filtrate was evaporated in vacuo. The obtained residue was purified by silica gel column chromatography (eluent: PE: DCM = 5) to give intermediate b-4.LC-MS: measurement value: 739.28 ([ M + H)] + ) The theoretical value is as follows: 738.35.
(2) Preparation of intermediate c-1:
in a three-necked bottle, a tubeUnder nitrogen protection, 2.20mmol of boron triiodide and 1.10mmol of intermediate b-4 were dissolved in 30mL of 1,2, 4-trichlorobenzene. After stirring at 180 ℃ for 20 h, the reaction mixture was diluted with dichloromethane (50 mL) and 100mL of ph =6 sodium phosphate buffer solution was added at 0 ℃, the aqueous layer was separated and extracted with dichloromethane (100 mL, three times). The crude product was chromatographed over a silica gel column (eluent: hexane/CH) 2 Cl 2 = 5/1) purification to give intermediate c-1.LC-MS: measurement value: 747.05 ([ M + H)] + ) The theoretical value is as follows: 746.34.
(3) Preparation of compound 64:
introducing nitrogen to protect, adding 10.0mmol of intermediate C-1, 12.0mmol of raw material C-2 into a three-neck flask, dissolving with mixed solvent (90 ml of toluene, 45ml of ethanol), and adding 1 × 10- 4 mol Pd(PPh 3 ) 4 3mol/L of K 2 CO 3 20mL of the aqueous solution was heated to reflux for 18 hours. The spot plate was sampled to confirm completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a pad of celite, rinsing with chloroform, and the resulting filtrate was evaporated in vacuo. The crude product was purified by silica gel column chromatography (eluent: PE: DCM = 5) to give the objective compound 64.
Example 5 synthesis of compound 75:
(1) Preparation of compound 75:
introducing nitrogen to protect, adding 10.0mmol of intermediate C-1, 12.0mmol of raw material C-3 into a three-neck flask, dissolving with mixed solvent (90 ml of toluene, 45ml of ethanol), and adding 1 × 10- 4 mol Pd(PPh 3 ) 4 3mol/L of K 2 CO 3 20mL of the aqueous solution was heated under reflux for 25 hours. The spot plate was sampled to confirm completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a pad of celite,washed with chloroform and the resulting filtrate was evaporated in vacuo. The crude product was purified by silica gel column chromatography (eluent: PE: DCM = 5) to give the target compound 75.
Example 6 synthesis of compound 98:
(1) Preparation of compound 98:
under the protection of nitrogen, 10.0mmol of intermediate C-1 and 12.0mmol of raw material C-4 are added into a three-necked bottle, dissolved by a mixed solvent (90 ml of toluene and 45ml of ethanol), and then added with 1 × 10- 4 mol Pd(PPh 3 ) 4 3mol/L of K 2 CO 3 20mL of the aqueous solution was heated under reflux for 20 hours. The spot plate was sampled to confirm completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a pad of celite, rinsing with chloroform, and the resulting filtrate was evaporated in vacuo. The crude product was purified by silica gel column chromatography (eluent: PE: DCM = 5) to give the target compound 98.
Example 7 synthesis of compound 110:
(1) Preparation of intermediate b-5:
introducing nitrogen to protect, adding 0.90mmol of raw material B-3,2.70mmol of intermediate a-1,5.20mmol of K 2 CO 3 And 20mL of DMF were added to a three-necked flask, which was then heated to 110 ℃. After stirring for 4 hours, the reaction mixture was cooled to room temperature, the reaction mixture was poured into a large amount of MeOH to give a precipitate, after filtration, the resulting solid was washed with MeOH, and the resulting filtrate was evaporated in vacuo. The obtained residue was purified by silica gel column chromatography (eluent: PE: DCM = 5) to give intermediate b-5.LC-MS: measurement value: 711.25 ([ M + H)] + ) The theoretical value is as follows: 710.46.
(2) Preparation of compound 110:
in a three-necked flask, 2.20mmol of boron triiodide and 1.10mmol of intermediate b-5 were dissolved in 30mL of 1,2, 4-trichlorobenzene under nitrogen protection. After stirring at 180 ℃ for 21 hours, the reaction mixture was diluted with dichloromethane (50 mL) and 100mL of ph =6 sodium phosphate buffer solution was added at 0 ℃, the aqueous layer was separated and extracted with dichloromethane (100 mL, three times). The crude product was chromatographed on a silica gel column (eluent: hexane/CH) 2 Cl 2 = 5/1) purification to give the target compound 110.
Example 8 synthesis of compound 114:
(1) Preparation of intermediate b-6:
introducing nitrogen to protect, adding 10.0mmol of raw material B-4, 24.0mmol of intermediate a-1, 150mL of toluene into a three-neck flask, stirring and mixing, and then adding 0.05mmol of Pd 2 (dba) 3 ，0.05mmol P(t-Bu) 3 30.0mmol of sodium tert-butoxide, and the reaction is refluxed at 105 ℃ for 24 hours. The spot plate was sampled to confirm completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a pad of celite, rinsing with chloroform, and the resulting filtrate was evaporated in vacuo. The residue obtained was purified by column chromatography on silica gel using hexane/toluene as eluent to give intermediate b-6, lc-MS: measurement value: 751.37 ([ M + H)] + ) The theoretical value is as follows: 750.45.
(2) Preparation of compound 114:
in a three-necked flask, 2.20mmol of boron triiodide and 1.10mmol of intermediate b-6 were dissolved in 30mL of 1,2, 4-trichlorobenzene under nitrogen protection. After stirring at 180 ℃ for 19 h, the reaction mixture was diluted with dichloromethane (50 mL) and added at 0 ℃Into 100mL of a sodium phosphate buffer solution of ph =6, the aqueous layer was separated and extracted with dichloromethane (100 ml, three times). The crude product was chromatographed on a silica gel column (eluent: hexane/CH) 2 Cl 2 = 5/1) purification to give the target compound 114.
Example 9 synthesis of compound 124:
(1) Preparation of compound 124:
introducing nitrogen to protect, adding 10.0mmol of intermediate C-1, 12.0mmol of raw material C-5 into a three-neck flask, dissolving with mixed solvent (90 ml of toluene, 45ml of ethanol), and adding 1 × 10- 4 mol Pd(PPh 3 ) 4 3mol/L of K 2 CO 3 20mL of the aqueous solution was heated under reflux for 24 hours. The spot plate was sampled to confirm completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a pad of celite, rinsing with chloroform, and the resulting filtrate was evaporated in vacuo. The crude product was purified by silica gel column chromatography (eluent: PE: DCM = 5) to give the target compound 124.
Example 10 synthesis of compound 131:
(1) Preparation of compound 131:
introducing nitrogen to protect, adding 10.0mmol of intermediate C-1, 12.0mmol of raw material C-6 into a three-neck flask, dissolving with mixed solvent (90 ml of toluene, 45ml of ethanol), and adding 1 × 10- 4 mol Pd(PPh 3 ) 4 3mol/L of K 2 CO 3 20mL of the aqueous solution was heated to reflux for 16 hours. The spot plate was sampled to confirm completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a pad of celite, rinsing with chloroform, and the resulting filtrate was evaporated in vacuo. The crude product was purified by silica gel column chromatography (eluent: PE: DCM = 5) to give the objective compound 131.
Example 11 synthesis of compound 140:
(1) Preparation of compound 140:
introducing nitrogen to protect, adding 10.0mmol of intermediate C-1, 12.0mmol of raw material C-7 into a three-neck flask, dissolving with mixed solvent (90 ml of toluene, 45ml of ethanol), and adding 1 × 10- 4 mol Pd(PPh 3 ) 4 3mol/L of K 2 CO 3 20mL of the aqueous solution was heated under reflux for 18 hours. The spot plate was sampled to confirm completion of the reaction. After cooling to room temperature, the reaction mixture was filtered through a pad of celite, rinsing with chloroform, and the resulting filtrate was evaporated in vacuo. The crude product was purified by silica gel column chromatography (eluent: PE: DCM = 5) to give the target compound 140.
The structural characterization of the compounds obtained in each example is shown in Table 1
TABLE 1
In the invention, X in the structure of the general formula (1) is obtained by a quantum chemical calculation method 1 、X 2 And X 3 The included angle theta is formed between the plane alpha and the plane beta of the B atom and the two N atoms in the parent nucleus. Firstly, performing geometric optimization on each structure through Gaussian16, and calculating the level as b3lyp/6-31G (d); after the molecular optimization is completed, X is called 1 、X 2 And X 3 And calculating normal vectors of the coordinates of the B atom and the two N atoms through the coordinates of any three atoms in the plane, and then calculating an included angle of the normal vectors, namely an included angle theta between the two planes, wherein the calculation result is shown in a table 2:
TABLE 2
| Compound (I) | Angle theta (degree) |
| 1 | 27.0840 |
| 4 | 28.9093 |
| 20 | 23.9633 |
| 64 | 28.0722 |
| 75 | 26.4911 |
| 98 | 26.9411 |
| 110 | 33.7122 |
| 114 | 29.8219 |
| 124 | 28.2833 |
| 131 | 27.9964 |
| 140 | 28.0134 |
| ref-1 | 3.5582 |
| ref-2 | 18.4783 |
As can be seen from the data in Table 2 above, the compounds of the present invention represented by general formula (1) have substituent groups introduced at specific positions of the parent nucleus, and the steric position of the compound is limited so that X in the structure of the compound is 1 、X 2 And X 3 The included angle theta between the plane alpha and the plane beta of the B atom and the two N atoms in the mother nucleus is within the range of 20-35 degrees, so that the torsional vibration in a resonance type boron-nitrogen frame structure is inhibited, the molecular rigidity is greatly enhanced, the radiation transition rate of the material is obviously improved, and the service life of a device can be prolonged. In the structure of the compound X 1 、X 2 And X 3 When the included angle theta between the plane alpha and the plane beta of the B atom and the two N atoms in the parent nucleus is more than 40 degrees, the molecules easily form an intramolecular charge transfer state (CT state), so that the fluorescence quantum yield of the material is reduced, and the half-peak width is widened.
The compound of the invention is used in a light-emitting device and can be used as a doping material of a light-emitting layer. The physicochemical properties of the compounds prepared in the above examples of the present invention were measured, and the results are shown in Table 3:
TABLE 3
Note: the glass transition temperature Tg is measured by differential scanning calorimetry (DSC, DSC204F1 differential scanning calorimeter of Germany Titan company), and the heating rate is 10 ℃/min; the thermogravimetric loss temperature Td is a temperature at which 1% of the weight is lost in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, japan, and the nitrogen flow rate is 20mL/min; the highest occupied molecular orbital HOMO energy level is tested by an ionization energy testing system (IPS-3), and the test is a nitrogen environment; eg was measured by a two-beam UV-visible spectrophotometer (model: TU-1901), LUMO = HOMO + Eg; PLQY (fluorescence quantum yield) and FWHM (full width at half maximum) were measured in the thin film state by Fluorolog-3 series fluorescence spectrometer from Horiba. τ (transient) was measured by Fluorolog-3 series fluorescence spectrometer of Horiba in thin film state, kr (radiation transition rate) =1/τ.
As can be seen from the data in Table 3 above, the compounds of the present invention have relatively high glass transition temperature and decomposition temperature. The luminescent layer is used as a doping material of the luminescent layer, and can inhibit the crystallization and the film phase separation of the material; meanwhile, the decomposition of the material under high brightness can be inhibited, and the service life of the device is prolonged. In addition, the compound has a proper HOMO energy level, is doped in a host material as a doping material, is favorable for inhibiting generation of carrier traps, and improves the energy transfer efficiency of a host and an object, so that the luminous efficiency of a device is improved.
The compound has higher fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%; meanwhile, the spectrum FWHM of the material is narrow, so that the color gamut of the device can be effectively improved, and the luminous efficiency of the device is improved; finally, the evaporation decomposition temperature of the material is higher, the evaporation decomposition of the material can be inhibited, the radiation transition rate of the material is higher, and the service life of the device can be effectively prolonged.
The application effect of the synthesized OLED material in the device is explained in detail by device examples 1-11 and device comparative examples 1-2. Compared with the device example 1, the device examples 2 to 11 and the device comparative examples 1 to 2 of the present invention have the same manufacturing process, and adopt the same substrate material and electrode material, and the film thickness of the electrode material is also kept consistent, except that the luminescent layer material in the device is replaced. The layer structures and test results of the device embodiments are shown in tables 4 and 5, respectively.
Device example 1
As shown in FIG. 1, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (having a film thickness of 150 nm) is washed, that is, washed with a cleaning agent (Semiclean M-L20), washed with pure water, dried, and then washed with ultraviolet rays and ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, HT-1 and HI-1 having a film thickness of 10nm were deposited as the hole injection layer 3 by a vacuum deposition apparatus, and the mass ratio of HT-1 to HI-1 was 97. Then, HT-1 was evaporated to a thickness of 60nm as the hole transport layer 4. EB-1 was then evaporated to a thickness of 30nm as an electron blocking layer 5. After the evaporation of the electron blocking material is finished, a light emitting layer 6 of the OLED light emitting device is manufactured, CBP is used as a main material, a compound 1 is used as a doping material, the mass ratio of the CBP to the compound 1 is 97, and the thickness of the light emitting layer is 30nm. After the light-emitting layer 6, HB-1 was continuously vacuum-deposited to a film thickness of 5nm, and this layer was a hole-blocking layer 7. After the hole-blocking layer 7, ET-1 and Liq were continuously vacuum-evaporated, the mass ratio of ET-1 to Liq was 1, the film thickness was 30nm, and this layer was an electron-transporting layer 8. On the electron transport layer 8, a LiF layer having a film thickness of 1nm was formed by a vacuum evaporation apparatus, and this layer was an electron injection layer 9. On the electron injection layer 9, a vacuum deposition apparatus was used to produce an Mg: the Ag electrode layer has a Mg/Ag mass ratio of 1.
The effect of the synthesized OLED materials of the present invention in the application of the device is detailed below by device examples 12-22 and device comparative examples 3-4. Compared with the device example 12, the device examples 13 to 22 and the device comparative examples 3 to 4 of the present invention have the same manufacturing process, and adopt the same substrate material and electrode material, and the film thickness of the electrode material is also kept consistent, except that the material of the light emitting layer in the device is replaced. The layer structures and test results of the device embodiments are shown in tables 4 and 5, respectively.
Device example 12
The transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (with a film thickness of 150 nm) is washed, namely washed by a cleaning agent (Semiclean M-L20), washed by pure water, dried and then washed by ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, HT-1 and HI-1 having a film thickness of 10nm were deposited as the hole injection layer 3 by a vacuum deposition apparatus, and the mass ratio of HT-1 to HI-1 was 97. Then, HT-1 was evaporated to a thickness of 60nm as a hole transport layer 4. EB-1 was then evaporated to a thickness of 30nm as an electron blocking layer 5. After the evaporation of the electron blocking material is finished, a light-emitting layer 6 of the OLED light-emitting device is manufactured, CBP and DMAC-BP are used as double-host materials, a compound 1 is used as a doping material, the mass ratio of CBP to DMAC-BP to the compound 1 is 67. After the light-emitting layer 6, HB-1 was continuously vacuum-deposited to a film thickness of 5nm, and this layer was a hole-blocking layer 7. After the hole-blocking layer 7, ET-1 and Liq were continuously vacuum-evaporated, the mass ratio of ET-1 to Liq was 1, the film thickness was 30nm, and this layer was an electron-transporting layer 8. On the electron transport layer 8, a LiF layer having a film thickness of 1nm was formed by a vacuum evaporation apparatus, and this layer was an electron injection layer 9. On the electron injection layer 9, a vacuum deposition apparatus was used to produce an Mg: the Ag electrode layer has a Mg/Ag mass ratio of 1.
The molecular structural formula of the related material is shown as follows:
after the OLED light emitting device was completed as described above, the anode and cathode were connected using a well-known driving circuit, and the current efficiency, external quantum efficiency, and lifetime of the device were measured. Device examples and comparative examples prepared in the same manner are shown in table 4; the results of the current efficiency, external quantum efficiency and lifetime tests of the resulting devices are shown in table 5.
TABLE 4
TABLE 5
Note: voltage, current efficiency, luminescence peak using IVL (current-voltage-brightness) test system (forskoda scientific instruments, suzhou); the life test system is an EAS-62C type OLED device life tester of Japan System research company; LT95 refers to the time it takes for the device luminance to decay to 95%; all data were at 10mA/cm 2 And (4) testing.
As can be seen from the device data results in table 5, compared with comparative device examples 1-4, the current efficiency, external quantum efficiency, and device lifetime of the organic light emitting device of the present invention are all greatly improved compared to the OLED device of the known material.
In summary, the present invention is only a preferred embodiment, and not intended to limit the present invention, and any modifications, equivalents, improvements, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (14)
1. A monoboron organic compound as a dopant material for OLEDs, characterized in that the monoboron organic compound has the structure shown in formula (1):
in the general formula (1), R 1 -R 3 Each independently represents cyano, substituted or unsubstituted C 1 -C 10 Chain alkyl group of (1), substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted amino, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 The heteroaryl group of (a);
X 1 -X 3 are respectively provided withIndependently represent C-R 4 ；R 4 Each occurrence, which is the same or different, is represented by H, deuterium atom, cyano, substituted or unsubstituted C 1 -C 10 Chain alkyl group of (1), substituted or unsubstituted C 1 -C 10 Alkoxy, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 Heteroaryl, substituted or unsubstituted C 3 -C 30 A ketone group of (a);
R 4 the connection mode with the general formula (1) is single bond substitution or ring combination connection;
the substituents of the above groups which are "substituted or unsubstituted" are optionally selected from deuterium atom, halogen atom, cyano, C 1 ～C 10 Chain alkyl group of (1), C 3 ～C 10 Cycloalkyl of (C) 6 ～C 30 Aryl radical, C 2 ～C 30 Any one of heteroaryl;
the hetero atom in the heteroaryl is one or more selected from oxygen, sulfur or nitrogen atoms;
and X 1 、X 2 And X 3 The included angle theta between the plane alpha and the plane beta of the B atom and the two N atoms in the parent nucleus is in the range of 10-40 degrees.
2. The monoboron organic compound of claim 1 wherein X is 1 、X 2 、X 3 The angle theta between the plane alpha and the plane beta of the parent nucleus in which the B atom and the two N atoms lie is in the range of 20 degrees to 35 degrees, more preferably in the range of 25 degrees to 30 degrees.
3. The monoboron organic compound of claim 1 having a structure according to any one of general formula (2) to general formula (5):
in the general formula (2) -the general formula (5), R 1 -R 3 Each independently represents a deuterium atom, a cyano group, a substituted or unsubstituted C 1 -C 10 Chain alkyl group of (1), substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted amino, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 The heteroaryl group of (a);
z is independently at each occurrence represented by C-R 5 ；R 5 Each occurrence being the same or different and being represented by H, deuterium atom, cyano, substituted or unsubstituted C 1 -C 10 Chain alkyl group of (1), substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 The heteroaryl group of (a);
the substituent of the above group which is "substituted or unsubstituted" is optionally selected from deuterium atom, halogen atom, cyano group, C 1 ～C 10 Chain alkyl group of (1), C 3 ～C 10 Cycloalkyl of, C 6 ～C 30 Aryl radical, C 2 ～C 30 Any one of heteroaryl;
the hetero atom in the heteroaryl is one or more selected from oxygen, sulfur or nitrogen atom.
4. The monoboronic organic compound of claim 1 having the structure of formula (6):
in the general formula (6), R 1 -R 3 Each independently represents a deuterium atom, a cyano group, a substituted or unsubstitutedC of (A) 1 -C 10 Chain alkyl group of (1), substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted amino, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 The heteroaryl group of (a);
R 4 represented by H, deuterium atom, cyano, substituted or unsubstituted C 1 -C 10 Chain alkyl group of (1), substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Alkoxy, substituted or unsubstituted C 6 -C 30 Aryl, substituted or unsubstituted C 3 -C 30 Heteroaryl, substituted or unsubstituted C 3 -C 30 A ketone group of (a);
the substituent of the above group which is "substituted or unsubstituted" is optionally selected from deuterium atom, halogen atom, cyano group, C 1 ～C 10 Chain alkyl group of (1), C 3 ～C 10 Cycloalkyl of, C 6 ～C 30 Aryl radical, C 2 ～C 30 Any one of heteroaryl;
the hetero atom in the heteroaryl is one or more selected from oxygen, sulfur or nitrogen atom.
5. The monoboronic organic compound of claim 1 wherein R is 1 -R 3 Independently represent a deuterium atom, a cyano group, an adamantyl group, a methyl group, a trifluoromethyl group, an ethyl group, an isopropyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenylyl group, a deuterated biphenylyl group, a terphenylyl group, a diphenylether group, a methyl-substituted diphenylether group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a phenyl-substituted pyridyl, quinolyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9-dimethylfluorenyl, phenyl-substituted amino, tert-butylphenyl-substituted amino, tert-butyl-substituted dibenzofuryl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, and the like,Tert-butyl-substituted phenyl, methyl-substituted biphenylyl, ethyl-substituted biphenylyl, isopropyl-substituted biphenylyl, tert-butyl-substituted biphenylyl, phenyl-substituted tert-butyl, xanthenone, phenyl-substituted triazinyl, phenyl-substituted boryl, methoxy, tert-butoxy;
the R is 4 Represented by H, deuterium atom, cyano group, adamantyl group, methyl group, trifluoromethyl group, ethyl group, isopropyl group, isobutyl group, tert-butyl group, cyclopentyl group, methyl-substituted cyclopentyl group, cyclohexyl group, phenyl group, deuterated phenyl group, phenylbenzofuran pyridine, biphenyl group, deuterated biphenyl group, terphenyl group, diphenyl ether group, methyl-substituted diphenyl ether group, benzophenone group, xanthenone group, naphthyl group, anthracene group, phenanthrene group, indenyl group, pyridazinyl group, pyrazinyl group, pyridyl group, phenyl-substituted pyridyl group, pyrimidinyl group, phenyl-substituted pyrimidinyl group, fluoranthenyl group, dihydroacenaphthenyl group, quinolyl group, isoquinoline group, phenylisoquinoline group, furyl group, phenanthridine group, thienyl group, benzofuryl group, dibenzofuryl group, dibenzothienyl group, carbazolyl group, phenylbenzoimidazolyl group benzodioxinyl, phenylphenanthridinyl, benzofuropyrimidinyl, N-phenylcarbazolyl, indolocarbazole, 9-dimethylfluorenyl, spirofluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuranyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenylyl, ethyl-substituted biphenylyl, isopropyl-substituted biphenylyl, tert-butyl-substituted biphenylyl, phenyl-substituted tert-butyl, xanthenoyl, phenyl-substituted triazinyl, dibenzofuranyl-substituted triazinyl, carbazolyl-substituted triazinyl, dibenzofuran-phenyl-triazinyl, indolocarbazole-phenyl-triazinyl, methoxy, tert-butoxy; r 4 The connection mode with the general formula (1) is single bond substitution or ring combination connection.
6. The monoboronic organic compound of claim 3 wherein R is 5 Represented by H, deuterium atom, cyano group, adamantyl group, methyl group, trifluoromethyl group, ethyl groupA phenyl group, an isopropyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenylyl group, a deuterated biphenylyl group, a terphenyl group, a diphenylether group, a methyl-substituted diphenylether group, a naphthyl group, an anthryl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a pyrimidyl group, a phenyl-substituted pyrimidyl group, a quinolyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9, 9-dimethylfluorenyl group, a spirofluorenyl group, a phenyl-substituted amino group, a tert-butyl-substituted dibenzofuryl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenylyl group, an ethyl-substituted biphenylyl group, an isopropyl-substituted biphenylyl group, a tert-butyl-substituted biphenylyl group, a phenyl-substituted tert-butyl group, a xanthenyl group, a phenyl-substituted triazinyl group, a phenyl-substituted boryl group, a methoxy group, and a tert-butoxy group.
7. The monoboronic organic compound of any one of claims 1 to 4, wherein R is 1 And R 2 Each independently represents methyl, isopropyl, tert-butyl or phenyl; r 3 Represented by phenyl, methyl, isopropyl, tert-butyl, trifluoromethyl or cyano.
8. The monoboronic organic compound of any one of claims 1 to 4 wherein R is 1 And R 2 Identically expressed as methyl, isopropyl, tert-butyl or phenyl; r 3 Represented by phenyl, methyl, isopropyl, tert-butyl, trifluoromethyl or cyano.
9. The monoboronic organic compound of any one of claims 1 to 4, characterized in that: the R is 1 And R 2 The same is represented by tert-butyl; r 3 Represented by phenyl, methyl, isopropyl, tert-butyl, trifluoromethyl, cyano.
10.The monoboronic organic compound of claim 4, characterized in that: the R is 1 And R 2 Each independently represents methyl, isopropyl, tert-butyl or phenyl, R 3 Expressed as phenyl, methyl, isopropyl, tertiary butyl, trifluoromethyl or cyano, and R4 is expressed as phenyl or tertiary butyl substituted phenyl.
11. The monoboron organic compound of claim 1 having a specific structural formula of any one of the following structures:
12. an organic electroluminescent device comprising a first electrode and a second electrode with an organic light-emitting functional layer therebetween, the organic light-emitting functional layer comprising a light-emitting layer, characterized in that the light-emitting layer contains a monoboron organic compound according to any one of claims 1 to 11.
13. An organic electroluminescent device according to claim 12, wherein the light-emitting layer comprises a host material and a dopant material, and wherein the dopant material comprises the monoboron organic compound according to any one of claims 1 to 11.
14. The organic light-emitting device according to claim 12, wherein the light-emitting layer comprises a first host material, a second host material, and a dopant material, wherein: at least one of the first host material and the second host material is a TADF material, and the dopant material is the monoboron organic compound according to any one of claims 1 to 11.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116948630A (en) * | 2023-06-05 | 2023-10-27 | 宇瑞(上海)化学有限公司 | OLED luminous composition and electroluminescent device comprising same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116948630A (en) * | 2023-06-05 | 2023-10-27 | 宇瑞(上海)化学有限公司 | OLED luminous composition and electroluminescent device comprising same |
| CN116948630B (en) * | 2023-06-05 | 2024-04-16 | 宇瑞(上海)化学有限公司 | OLED luminous composition and electroluminescent device comprising same |
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