CN113620885A - Electronic transmission material containing deuterium atom and its application - Google Patents
Electronic transmission material containing deuterium atom and its application Download PDFInfo
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- CN113620885A CN113620885A CN202010381531.5A CN202010381531A CN113620885A CN 113620885 A CN113620885 A CN 113620885A CN 202010381531 A CN202010381531 A CN 202010381531A CN 113620885 A CN113620885 A CN 113620885A
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- substituted
- carbon atoms
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- 239000000463 material Substances 0.000 title claims abstract description 51
- 229910052805 deuterium Inorganic materials 0.000 title claims description 26
- 125000004431 deuterium atom Chemical group 0.000 title abstract description 5
- 230000005540 biological transmission Effects 0.000 title description 2
- -1 benzimidazole compound Chemical class 0.000 claims abstract description 91
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 125000001424 substituent group Chemical group 0.000 claims abstract description 55
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 238000009472 formulation Methods 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 247
- 239000010410 layer Substances 0.000 claims description 77
- 125000001072 heteroaryl group Chemical group 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000006413 ring segment Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 238000006467 substitution reaction Methods 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 239000012044 organic layer Substances 0.000 claims description 14
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 125000005104 aryl silyl group Chemical group 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 13
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 13
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000004185 ester group Chemical group 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 10
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 10
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 239000003446 ligand Substances 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- 150000001975 deuterium Chemical group 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 150000004696 coordination complex Chemical class 0.000 claims description 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 6
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 4
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical group [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 claims description 4
- 229960003540 oxyquinoline Drugs 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052711 selenium Inorganic materials 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- URZSYMJOMDCRMX-UHFFFAOYSA-N [B].OC=1C=CC=C2C=CC=NC12.OC=1C=CC=C2C=CC=NC12.OC=1C=CC=C2C=CC=NC12 Chemical compound [B].OC=1C=CC=C2C=CC=NC12.OC=1C=CC=C2C=CC=NC12.OC=1C=CC=C2C=CC=NC12 URZSYMJOMDCRMX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052790 beryllium Inorganic materials 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- RTYLNZJDTYKYFY-UHFFFAOYSA-N calcium;quinolin-8-ol Chemical compound [Ca].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 RTYLNZJDTYKYFY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 229940125904 compound 1 Drugs 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- MOOHXQFFIPDLNX-UHFFFAOYSA-N magnesium;quinolin-8-ol Chemical compound [Mg].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 MOOHXQFFIPDLNX-UHFFFAOYSA-N 0.000 claims description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- WLZQSQUYKYQKKY-UHFFFAOYSA-N potassium;quinolin-8-ol Chemical compound [K].C1=CN=C2C(O)=CC=CC2=C1 WLZQSQUYKYQKKY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000001725 pyrenyl group Chemical group 0.000 claims description 2
- ZVJDFJRDKIADMB-UHFFFAOYSA-N quinolin-8-ol;sodium Chemical compound [Na].C1=CN=C2C(O)=CC=CC2=C1 ZVJDFJRDKIADMB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 14
- 230000003111 delayed effect Effects 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 150000003384 small molecules Chemical class 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical class C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- 238000005538 encapsulation Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000000477 aza group Chemical group 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 229920001621 AMOLED Polymers 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical group C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 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 description 2
- 229960005544 indolocarbazole Drugs 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000006504 o-cyanobenzyl group Chemical group [H]C1=C([H])C(C#N)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 238000013086 organic photovoltaic Methods 0.000 description 2
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 2
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
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Abstract
Electronic transport materials containing deuterium atoms and uses thereof are disclosed. The electron transport material containing deuterium atoms is a benzimidazole compound having a deuterated substituent, and can be used as an electron transport material in an electroluminescent device. The novel compounds can improve the efficiency of the organic electroluminescent device, simultaneously obtain longer device life and provide better device performance. An electroluminescent device and compound formulation are also disclosed.
Description
Technical Field
The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. More particularly, it relates to a benzimidazole compound having a deuterated substituent, and an organic electroluminescent device and a compound formulation comprising the same.
Background
Organic electronic devices include, but are not limited to, the following classes: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), Organic Light Emitting Transistors (OLETs), Organic Photovoltaics (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light emitting devices.
In 1987, Tang and Van Slyke of Islamic Kodak reported a two-layer organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987,51(12): 913-915). Upon biasing the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). The most advanced OLEDs may comprise multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between the cathode and anode. Since OLEDs are a self-emissive solid state device, it offers great potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications, such as in the fabrication of flexible substrates.
OLEDs can be classified into three different types according to their light emitting mechanisms. The OLEDs invented by Tang and van Slyke are fluorescent OLEDs. It uses only singlet luminescence. The triplet states generated in the device are wasted through the non-radiative decay channel. Therefore, the Internal Quantum Efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hinders the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complex-containing heavy metals as emitters. Thus, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributes to the commercialization of active matrix OLEDs (amoleds). Recently, Adachi has achieved high efficiency through Thermally Activated Delayed Fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons are able to generate singlet excitons through reverse intersystem crossing, resulting in high IQE.
OLEDs can also be classified into small molecule and polymer OLEDs depending on the form of the material used. Small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of small molecules can be large, as long as they have a precise structure. Dendrimers with well-defined structures are considered small molecules. The polymeric OLED comprises a conjugated polymer and a non-conjugated polymer having a pendant light-emitting group. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the fabrication process.
Various OLED manufacturing methods exist. Small molecule OLEDs are typically fabricated by vacuum thermal evaporation. Polymer OLEDs are fabricated by solution processes such as spin coating, ink jet printing and nozzle printing. Small molecule OLEDs can also be made by solution processes if the material can be dissolved or dispersed in a solvent.
In general, an organic electroluminescent device has a structure including an anode, a cathode, and an organic material layer interposed therebetween. Electric charges are injected into an organic layer formed between an anode and a cathode to form electron and hole pairs, causing an organic compound having fluorescent or phosphorescent characteristics to generate light emission. The organic layers may be formed of a multilayer structure composed of different substances due to the difference in the moving speed of holes and electrons, such as a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
To achieve better device performance, such as higher device efficiency, longer device lifetime, etc., it is a solution to develop new electron transport materials.
A series of compounds having a benzimidazole structure are disclosed in KR20170107140 (a):
wherein R is1Is imidazolyl, phenyl or pyridyl, R2Deuterated alkyl or aryl, specific examples are:
the compounds disclosed in this application must have a structure in which the benzimidazole is linked to the anthracene at the 2-position via a phenylene group, which does not disclose or teach the use of benzimidazole to link to other sites of anthracene or other fused structures.
KR101460365(B1) discloses a series of compounds having phenanthro [9,10 ]]Compound of imidazole structure:
specific examples are
The compounds disclosed in this patent must have phenanthro [9,10 ]]Imidazole structures, and does not disclose or teach the use of benzimidazole structures with deuterated substituents to link fused structures.
In order to obtain better performance of the organic light emitting device, one idea is to develop a more excellent electron transport material to improve electron transport efficiency, so that holes and electrons in the device reach a more balanced state, thereby improving light emitting efficiency and/or lifetime. Although there have been many studies on electron transport materials, the properties of the materials have shortcomings, and the development of new high-performance electron transport materials is still in need.
Disclosure of Invention
The present invention aims to solve at least part of the above problems by providing a series of benzimidazole compounds having deuterated substituents. The compounds are useful as electron transport materials in organic electroluminescent devices. The novel compounds can improve the efficiency of the organic electroluminescent device, simultaneously obtain longer device life and provide better device performance.
According to one embodiment of the present invention, a compound having a structure represented by formula 1 is disclosed:
wherein the content of the first and second substances,
ring X and ring Y are each independently selected from an aromatic ring having 5 to 30 ring atoms or a heteroaromatic ring having 5 to 30 ring atoms;
Z1-Z4each independently selected from CRzOr N;
Rxand RyThe same or different at each occurrence denotes mono-, poly-or no-substitution;
Rx、Ryand RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents Rx，RyCan optionally be linked to form a ring;
L1and L2Each occurrence, the same or different, is selected from the group consisting of: a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and combinations thereof;
ar is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;
r is selected from substituted alkyl having 1 to 20 carbon atoms, substituted cycloalkyl having 3 to 20 carbon atoms, substituted aryl having 6 to 30 carbon atoms, substituted heteroaryl having 3 to 30 carbon atoms, or combinations thereof; and said R contains at least one deuterium atom.
According to another embodiment of the present invention, there is also disclosed an electroluminescent device including an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer including a compound having a structure represented by formula 1:
wherein the content of the first and second substances,
ring X and ring Y are each independently selected from an aromatic ring having 5 to 30 ring atoms or a heteroaromatic ring having 5 to 30 ring atoms;
Z1-Z4each independently selected from CRzOr N;
Rxand RyThe same or different at each occurrence denotes mono-, poly-or no-substitution;
Rx、Ryand RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilicon having 3 to 20 carbon atomsA group, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents Rx，RyCan optionally be linked to form a ring;
L1and L2Each occurrence, the same or different, is selected from the group consisting of: a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and combinations thereof;
ar is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;
r is selected from substituted alkyl having 1 to 20 carbon atoms, substituted cycloalkyl having 3 to 20 carbon atoms, substituted aryl having 6 to 30 carbon atoms, substituted heteroaryl having 3 to 30 carbon atoms, or combinations thereof; and said R contains at least one deuterium atom.
According to another embodiment of the present invention, there is also disclosed a compound formulation comprising the compound having the structure represented by formula 1.
The novel benzimidazole compound with the deuterated substituent can be used as an electron transport material in an electroluminescent device. The novel compounds can improve the efficiency of the organic electroluminescent device, simultaneously obtain longer device life and provide better device performance.
Drawings
FIG. 1 is a schematic representation of an organic light emitting device that can contain the compounds and compound formulations disclosed herein.
Fig. 2 is a schematic view of another organic light emitting device that can contain compounds and compound formulations disclosed herein.
Figure 3 is structural formula 1 showing compounds as disclosed herein.
Detailed Description
OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically, but without limitation, illustrates an organic light emitting device 100. The figures are not necessarily to scale, and some of the layer structures in the figures may be omitted as desired. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, an emissive layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 may be fabricated by sequentially depositing the described layers. The nature and function of the layers, as well as exemplary materials, are described in more detail in U.S. patent US7,279,704B2, columns 6-10, which is incorporated herein by reference in its entirety.
There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F at a molar ratio of 50:14TCNQ m-MTDATA as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. patent No. 6,303,238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of a metal such as Mg: Ag and an overlying layer of transparent, conductive, sputter-deposited ITO. The principles and use of barrier layers are described in more detail in U.S. patent No. 6,097,147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. Which can be incorporated by reference in its entiretyA description of protective layers is found in U.S. patent application publication No. 2004/0174116.
The above-described hierarchical structure is provided via non-limiting embodiments. The function of the OLED may be achieved by combining the various layers described above, or some layers may be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of materials may be used to achieve optimal performance. Any functional layer may comprise several sub-layers. For example, the light emitting layer may have two layers of different light emitting materials to achieve a desired light emission spectrum.
In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.
The OLED also requires an encapsulation layer, as shown in fig. 2, which is an exemplary, non-limiting illustration of an organic light emitting device 200, which differs from fig. 1 in that an encapsulation layer 102 may also be included over the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function may be used as the encapsulation layer, such as glass or a hybrid organic-inorganic layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film encapsulation is described in U.S. patent US7,968,146B2, the entire contents of which are incorporated herein by reference.
Devices manufactured according to embodiments of the present invention may be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and/or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet handsets, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and tail lights.
The materials and structures described herein may also be used in other organic electronic devices as previously listed.
As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. Where a first layer is described as being "disposed on" a second layer, the first layer is disposed farther from the substrate. Other layers may be present between the first and second layers, unless it is specified that the first layer is "in contact with" the second layer. For example, a cathode can be described as being "disposed on" an anode even though various organic layers are present between the cathode and the anode.
As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and/or deposited from a liquid medium in the form of a solution or suspension.
A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive properties of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.
It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by delaying fluorescence beyond 25% spin statistics. Delayed fluorescence can generally be divided into two types, i.e., P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence results from triplet-triplet annihilation (TTA).
On the other hand, E-type delayed fluorescence does not depend on collision of two triplet states, but on conversion between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small mono-triplet gap in order to switch between energy states. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as Thermally Activated Delayed Fluorescence (TADF). A significant feature of TADF is that the retardation component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize non-radiative decay from the triplet state, then the fraction of backfill singlet excited states may reach 75%. The total singlet fraction may be 100%, far exceeding 25% of the spin statistics of the electrogenerated excitons.
The delayed fluorescence of type E can be characterized by excitation of complex systems or single compoundsIn (1). Without being bound by theory, it is believed that E-type delayed fluorescence requires the light emitting material to have a small mono-triplet energy gap (Δ Ε)S-T). Organic non-metal containing donor-acceptor emissive materials may be able to achieve this. The emission of these materials is generally characterized as donor-acceptor Charge Transfer (CT) type emission. Spatial separation of HOMO from LUMO in these donor-acceptor type compounds generally results in small Δ ES-T. These states may include CT states. Generally, donor-acceptor light emitting materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) to an electron acceptor moiety (e.g., a six-membered, N-containing, aromatic ring).
Definitions for substituent terms
Halogen or halide-as used herein, includes fluorine, chlorine, bromine and iodine.
Alkyl-comprises both straight and branched chain alkyl groups. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. In addition, the alkyl group may be optionally substituted. The carbons in the alkyl chain may be substituted with other heteroatoms. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl and neopentyl are preferable.
Cycloalkyl-as used herein, comprises a cyclic alkyl group. Preferred cycloalkyl groups are those containing 4 to 10 ring carbon atoms and include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4, 4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. In addition, the cycloalkyl group may be optionally substituted. The carbon in the ring may be substituted with other heteroatoms.
Alkenyl-as used herein, encompasses both straight and branched chain olefinic groups. Preferred alkenyl groups are those containing 2 to 15 carbon atoms. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a1, 3-butadienyl group, a 1-methylvinyl group, a styryl group, a 2, 2-diphenylvinyl group, a 1-methylallyl group, a1, 1-dimethylallyl group, a 2-methylallyl group, a 1-phenylallyl group, a 3, 3-diphenylallyl group, a1, 2-dimethylallyl group, a 1-phenyl-1-butenyl group and a 3-phenyl-1-butenyl group. In addition, alkenyl groups may be optionally substituted.
Alkynyl-as used herein, straight and branched alkynyl groups are contemplated. Preferred alkynyl groups are those containing 2 to 15 carbon atoms. In addition, alkynyl groups may be optionally substituted.
Aryl or aromatic-as used herein, non-fused and fused systems are contemplated. Preferred aryl groups are those containing from 6 to 60 carbon atoms, more preferably from 6 to 20 carbon atoms, and even more preferably from 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene,
perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, the aryl group may be optionally substituted. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p- (2-phenylpropyl) phenyl, 4 '-methyldiphenyl, 4' -tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesityl and m-quaterphenyl.
Heterocyclyl or heterocyclic-as used herein, aromatic and non-aromatic cyclic groups are contemplated. Heteroaryl also refers to heteroaryl. Preferred non-aromatic heterocyclic groups are those containing 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen and sulfur. The heterocyclic group may also be an aromatic heterocyclic group having at least one hetero atom selected from a nitrogen atom, an oxygen atom, a sulfur atom and a selenium atom.
Heteroaryl-as used herein, non-fused and fused heteroaromatic groups are contemplated which may contain 1 to 5 heteroatoms. Preferred heteroaryl groups are those containing from 3 to 30 carbon atoms, more preferably from 3 to 20 carbon atoms, more preferably from 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridine indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, bisoxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indoline, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuropyridine, furobipyridine, benzothienopyridine, thienobipyridine, cinnolino, benzoselenophenopyridine, selenobenzene, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-azaborine, 1, 3-azaborine, 1, 4-azaborine, borazole, and aza analogues thereof. In addition, the heteroaryl group may be optionally substituted.
Alkoxy-is represented by-O-alkyl. Examples and preferred examples of the alkyl group are the same as those described above. Examples of the alkoxy group having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms include methoxy, ethoxy, propoxy, butoxy, pentyloxy and hexyloxy. The alkoxy group having 3 or more carbon atoms may be linear, cyclic or branched.
Aryloxy-is represented by-O-aryl or-O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. Examples of the aryloxy group having 6 to 40 carbon atoms include a phenoxy group and a biphenyloxy group.
Aralkyl-as used herein, an alkyl group having an aryl substituent. In addition, the aralkyl group may be optionally substituted. Examples of the aralkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α -naphthylmethyl, 1- α -naphthylethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthylethyl, 2- β -naphthylethyl, 1- β -naphthylisopropyl, 2- β -naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferable.
The term "aza" in aza-dibenzofuran, aza-dibenzothiophene, etc., means that one or more C-H groups in the corresponding aromatic moiety are replaced by a nitrogen atom. For example, azatriphenylenes include dibenzo [ f, h ] quinoxalines, dibenzo [ f, h ] quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-described aza derivatives may be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be encompassed within the terms described herein.
In this disclosure, unless otherwise defined, when any one of the terms in the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amine, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, meaning alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amine, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino, any of which groups may be substituted with one or more moieties selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, unsubstituted aralkyl groups having 7 to 30 carbon atoms, unsubstituted alkoxy groups having 1 to 20 carbon atoms, unsubstituted aryloxy groups having 6 to 30 carbon atoms, unsubstituted alkenyl groups having 2 to 20 carbon atoms, unsubstituted aryl groups having 6 to 30 carbon atoms, unsubstituted heteroaryl groups having 3 to 30 carbon atoms, unsubstituted silyl groups having 3 to 20 carbon atoms, unsubstituted arylsilyl groups having 6 to 20 carbon atoms, unsubstituted amine groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, nitrile groups, isonitrile groups, thio groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
It will be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name may be written depending on whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or depending on whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or linking fragments are considered to be equivalent.
In the compounds mentioned in the present disclosure, a hydrogen atom may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. Substitution of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.
In the compounds mentioned in the present disclosure, multiple substitution means that a double substitution is included up to the range of the maximum available substitutions. When a substituent in a compound mentioned in the present disclosure represents multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), that is, it means that the substituent may exist at a plurality of available substitution positions on its connecting structure, and the substituent existing at each of the plurality of available substitution positions may be the same structure or different structures.
In the compounds mentioned in the present disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless specifically defined, for example, adjacent substituents can be optionally linked to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally linked to form a ring, including both the case where adjacent substituents may be linked to form a ring and the case where adjacent substituents are not linked to form a ring. When adjacent substituents can optionally be joined to form a ring, the ring formed can be monocyclic or polycyclic, as well as alicyclic, heteroalicyclic, aromatic or heteroaromatic rings. In this expression, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom as well as substituents bonded to carbon atoms directly bonded to each other.
The expression that adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
the expression that adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
further, the expression that adjacent substituents can be optionally connected to form a ring is also intended to be taken to mean that, in the case where one of two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded at a position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following equation:
according to one embodiment of the present invention, a compound having a structure represented by formula 1 is disclosed:
wherein the content of the first and second substances,
ring X and ring Y are each independently selected from an aromatic ring having 5 to 30 ring atoms or a heteroaromatic ring having 5 to 30 ring atoms;
Z1-Z4each independently selected from CRzOr N;
Rxand RyThe same or different at each occurrence denotes mono-, poly-or no-substitution;
Rx、Ryand RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents Rx，RyCan optionally be linked to form a ring;
L1and L2Identical or different at each occurrenceSelected from the group consisting of: a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and combinations thereof;
ar is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;
r is selected from substituted alkyl having 1 to 20 carbon atoms, substituted cycloalkyl having 3 to 20 carbon atoms, substituted aryl having 6 to 30 carbon atoms, substituted heteroaryl having 3 to 30 carbon atoms, or combinations thereof; and said R contains at least one deuterium atom.
As used herein, the adjacent substituent Rx，RyCan optionally be linked to form a ring, intended to denote when a plurality of substituents R are presentxWhen adjacent substituent RxCan optionally be linked to form a ring, when a plurality of substituents R are presentyWhen adjacent substituent RyCan optionally be linked to form a ring. Obviously, when a plurality of substituents R are presentxA plurality of substituents RyWhen adjacent substituent Rx，RyOr may be both unconnected to form a ring.
According to one embodiment of the invention, wherein ring X and ring Y are each independently selected from an aromatic ring having 6 to 18 ring atoms or a heteroaromatic ring having 5 to 18 ring atoms.
According to one embodiment of the invention, wherein ring X and ring Y are each independently selected from a benzene ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, a fluoranthene ring, a pyridine ring or a pyrazine ring.
According to one embodiment of the invention, ring X and ring Y are each independently selected from benzene rings.
According to an embodiment of the present invention, wherein in the formula 1, Ar is selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms.
According to an embodiment of the present invention, wherein in formula 1, Ar is selected from the group consisting of: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, pyrenyl, fluoranthenyl, 9, 9-dimethylfluorenyl, spirobifluorenyl, pyridyl, quinolinyl, phenanthrolinyl, 9, 9-dimethylazafluorenyl, dibenzofuranyl, dibenzothiophenyl, and combinations thereof.
According to an embodiment of the present invention, wherein in formula 1, Ar is selected from any one of the group consisting of the following structures:
in this embodiment, the dotted bond represents the structure and L in formula 11The location of the connection.
According to an embodiment of the present invention, wherein in said formula 1, L1And L2Each independently selected from a single bond or any of the group consisting of:
wherein R isaThe same or different at each occurrence denotes mono-, poly-or unsubstituted;
Raeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkyl having 6 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, or substituted or unsubstituted cycloalkyl having 3 to 20 carbon atomsAn arylsilyl group of carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile, an isonitrile, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents RaCan optionally be linked to form a ring.
In this embodiment, the dotted bond represents the position where the structures are connected in equation 1.
In this example, the adjacent substituents RaCan optionally be linked to form a ring, intended to denote when a plurality of substituents R are presentaWhen there is any adjacent RaCan be linked to form a ring. Obviously, when a plurality of substituents R are presentaWhen the substituents R areaOr may be both unconnected to form a ring.
According to an embodiment of the present invention, wherein in said formula 1, L1And L2Each independently selected from a single bond or phenylene.
According to an embodiment of the present invention, wherein in the formula 1, R is selected from a substituted alkyl group having 1 to 20 carbon atoms, a substituted cycloalkyl group having 3 to 20 carbon atoms, a substituted aryl group having 6 to 25 carbon atoms, a substituted heteroaryl group having 3 to 25 carbon atoms, or a combination thereof; and said R comprises at least one of D, CD2Or CD3。
According to an embodiment of the present invention, wherein in formula 1, R is selected from the group consisting of: deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated butyl, deuterated isobutyl, deuterated tert-butyl, deuterated pentyl, deuterated hexyl, deuterated heptyl, deuterated octyl, deuterated nonyl, deuterated cyclopropyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated phenyl, deuterated naphthyl, deuterated pyridyl, deuterated fluorenyl, deuterated spirobifluorenyl, deuterated dibenzofuranyl, deuterated dibenzothiophenyl, deuterated carbazolyl, and combinations thereof.
In this example, R is selected from the group of deuterated substituents, which is intended to mean that the deuterated substituents can be partially deuterated substituted substituents or completely deuterated substituted substituents. For example, when R is selected from deuterated methyl, it means that R can be selected from partially deuterated substituted methyl (mono-deuterated methyl or di-deuterated methyl), and R can also be selected from fully deuterated substituted methyl (tri-deuterated methyl). The same is true when R is selected from other deuterated groups.
According to an embodiment of the present invention, wherein in formula 1, R is selected from any one of the group consisting of R1 to R100 below:
in this example, the dotted bonds represent the positions where the R1 to R100 are attached to the imidazole ring in formula 1.
According to an embodiment of the present invention, wherein in said formula 1, Z1-Z4Each independently selected from CRz，RzEach occurrence, identically or differently, is selected from: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, or combinations thereof.
According to an embodiment of the present invention, wherein in said formula 1, Z1-Z4Each independently selected from CRz，RzSelected from hydrogen or deuterium, the same or different at each occurrence.
According to an embodiment of the present invention, wherein the compound is selected from the group consisting of compound 1 to compound 217:
according to an embodiment of the present invention, there is also disclosed an electroluminescent device, including:
an anode, a cathode, a anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having a structure represented by formula 1:
wherein the content of the first and second substances,
ring X and ring Y are each independently selected from an aromatic ring having 5 to 30 ring atoms or a heteroaromatic ring having 5 to 30 ring atoms;
Z1-Z4each independently selected from CRzOr N;
Rxand RyThe same or different at each occurrence denotes mono-, poly-or no-substitution;
Rx、Ryand RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, getSubstituted or unsubstituted amine groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents Rx，RyCan optionally be linked to form a ring;
L1and L2Each occurrence, the same or different, is selected from the group consisting of: a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and combinations thereof;
ar is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;
r is selected from substituted alkyl having 1 to 20 carbon atoms, substituted cycloalkyl having 3 to 20 carbon atoms, substituted aryl having 6 to 30 carbon atoms, substituted heteroaryl having 3 to 30 carbon atoms, or combinations thereof; and said R contains at least one deuterium atom.
According to one embodiment of the invention, in the device, the organic layer is an electron transport layer and the compound is an electron transport material.
According to an embodiment of the invention, in the device, the electron transport layer further comprises at least one material.
According to one embodiment of the invention, in the device, the electron transport layer further comprises at least one metal complex.
According to one embodiment of the present invention, in the device, the metal complex includes a ligand L represented by formula 2a：
Wherein Q1To Q6Each independently selected from CRqOr N; rqEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, substituted or unsubstituted silyl having 3 to 20 carbon atoms, cyano, substituted or unsubstituted aryl having 6 to 30 carbon atoms and substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;
wherein W is selected from NRNO, S or Se;
RNeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
According to one embodiment of the invention, the device wherein the metal complex is selected from the group consisting of 8-hydroxyquinoline-lithium, 8-hydroxyquinoline-sodium, 8-hydroxyquinoline-potassium, bis (8-hydroxyquinoline) -beryllium, bis (8-hydroxyquinoline) -magnesium, bis (8-hydroxyquinoline) -calcium, tris (8-hydroxyquinoline) -boron, tris (8-hydroxyquinoline) -aluminum, and tris (8-hydroxyquinoline) -gallium.
According to another embodiment of the present invention, there is also disclosed a compound formulation comprising a compound having a structure represented by formula 1. The specific structure of the compound is shown in any one of the embodiments.
In combination with other materials
The materials described herein for use in particular layers in an organic light emitting device may be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. patent application Ser. No. 0132-0161 of U.S. 2016/0359122A1, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
Materials described herein as being useful for particular layers in an organic light emitting device can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein may be used in conjunction with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application Ser. No. US2015/0349273A1, paragraph 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
In the examples of material synthesis, all reactions were carried out under nitrogen unless otherwise stated. All reaction solvents were anhydrous and used as received from commercial sources. The synthesis product is subjected to structural validation and characterization using one or more equipment conventional in the art (including, but not limited to, Bruker's nuclear magnetic resonance apparatus, Shimadzu's liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, Shanghai prism-based fluorescence spectrophotometer, Wuhan Corset's electrochemical workstation, Anhui Beidek's sublimator, etc.) in a manner well known to those skilled in the art. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, an evaporator manufactured by Angstrom Engineering, an optical test system manufactured by Fushida, Suzhou, an ellipsometer manufactured by Beijing Mass., etc.) in a manner well known to those skilled in the art. Since the relevant contents of the above-mentioned device usage, testing method, etc. are known to those skilled in the art, the inherent data of the sample can be obtained with certainty and without being affected, and therefore, the relevant contents are not described in detail in this patent.
Materials synthesis example:
the preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limited to, and the synthetic route and the preparation method thereof are as follows:
synthesis example 1: synthesis of Compound 2
Step 1. Synthesis of [ intermediate 1-a ]
1-fluoro-2-nitrobenzene (10.0g, 71mmol), 4-bromoaniline (24.2g, 142mmol) were charged to a 100mL two-necked round bottom flask, followed by 30mL of dimethyl sulfoxide. The reaction flask was warmed to 100 ℃ and stirred under nitrogen for 48 hours. After the reaction is finished, the reaction system is cooled to room temperature, 200mL of water is added, dichloromethane is used for extraction for three times, and the organic phase is dried and concentrated to obtain a brownish red solid. The resulting solid was added to 500mL of ethanol and stirred under nitrogen for 2 hours, cooled and filtered to give a red solid [ intermediate 1-a ] (17.3g,59.0mmol, 83.2%).
Step 2. Synthesis of [ intermediate 1-b ]
[ intermediate 1-a ] (15g, 51mmol), stannous chloride (48.5g, 255.0mmol) were charged into a 500mL three-necked round-bottomed flask, followed by 150mL of anhydrous ethanol. The reaction flask was heated to 75 ℃ and refluxed, and stirred under nitrogen atmosphere for 4 hours, and the reaction solution turned from red suspension to colorless and clear. After the reaction is finished, cooling the reaction system to room temperature, removing the solvent under reduced pressure, dissolving the ethyl acetate, and then dropwise adding a potassium hydroxide aqueous solution (2M) to adjust the pH to 8-9. After three extractions with ethyl acetate, the organic phase was concentrated by drying to give a pale yellow solid. The resulting solid was added to 500mL of n-hexane and stirred under nitrogen for 2 hours, cooled and filtered to give a white solid [ intermediate 1-b ] (10.5g, 39.8mmol, 78%).
Step 3. Synthesis of [ intermediate 1-c ]
[ intermediate 1-b ] (7.0g, 26.6mmol) was charged into a 250mL three-necked round-bottomed flask, 60mL of tetrahydrofuran was added to dissolve the intermediate, and then deuterated acetyl chloride (2.2g, 26.6mmol) and N, N-diisopropylethylamine (3mL) were sequentially added to the mixture, so that the reaction solution became red, the reaction flask was stirred under nitrogen atmosphere at room temperature for 24 hours, and then 150mL of water was added to stop the reaction, and the reaction was further stirred to precipitate a solid. The solid was filtered, dissolved in 60mL of glacial acetic acid, heated to 140 ℃ under reflux, and stirred under nitrogen for 24 hours, with the reaction solution being wine-red. After the reaction was completed, it was cooled to room temperature, the pH was adjusted to 6-8 with an aqueous solution of sodium hydroxide (2M) at 0 ℃ in ice bath, and extracted with ethyl acetate, and the organic phase was concentrated by dryness and then isolated by column chromatography to give a purple solid [ intermediate 1-c ] (5.0g, 17.3mmol, 65.0%).
Step 4. Synthesis of Compound 2
[ intermediate 1-c ] (2.5g, 8.6mmol), 10- ([1,1' -biphenyl ] -4-yl) anthracen-9-ylboronic acid (3.24g, 8.6mmol), palladium tetratriphenylphosphine (520mg, 0.46mmol), and potassium carbonate (2.50g, 18.7mmol) were charged into a 250mL three-necked round-bottomed flask, followed by 45mL of tetrahydrofuran and 5mL of water. The reaction flask was warmed to 85 ℃ under reflux and stirred under nitrogen for 10 hours. After completion of the reaction, the reaction system was cooled to room temperature and extracted with dichloromethane, and the organic phase was concentrated by drying and then isolated by column chromatography to obtain Compound 2(1.7g,3.2mmol, 37.2%) as a pale yellow solid. The product was identified as the target product, molecular weight 539.2.
It will be appreciated by those skilled in the art that the above preparation method is only an illustrative example, and that those skilled in the art can modify it to obtain other structures of the compounds of the present invention.
Device example 1
First, a glass substrate, having an Indium Tin Oxide (ITO) anode 80nm thick, was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate is then mounted on a substrate holder and loaded into a vacuum chamber. The organic layer specified below was in a vacuum of about 10 degrees-8In the case of torr, the evaporation was performed by thermal vacuum evaporation at a rate of 0.2 to 2 angstroms/second in turn on an ITO anode. Compound HI
Used as a Hole Injection Layer (HIL). Compound HT
Used as a Hole Transport Layer (HTL). Compound EB
Used as an Electron Blocking Layer (EBL). The compound GD was then doped in the compound EB and the compound HB as a light emitting layer (EML,
compound EB compound HB: compound GD ═ 46:46: 8). On the light-emitting layer, a compound HB
The Hole Blocking Layer (HBL) was formed by evaporation. Compound 2 of the present invention and 8-hydroxyquinoline-lithium (Liq) were then co-evaporated as an Electron Transport Layer (ETL). Finally, Liq of 10 angstroms in thickness was evaporated as an electron injection layer, and 1200 angstroms of aluminum was evaporated as a cathode. The device was then transferred back to the glove box and encapsulated with a glass lid and moisture absorber to complete the device.
Device comparative example 1
Device comparative example 1 was prepared in the same manner as device example 1 except that comparative compound ET1 was used in place of compound 2 of the present invention in the Electron Transport Layer (ETL).
Device comparative example 2
Device comparative example 2 was prepared in the same manner as device example 1 except that the inventive compound 2 was replaced by comparative compound ET2 in the Electron Transport Layer (ETL).
The detailed device layer structure and thickness are shown in the table below. Wherein more than one layer of the materials used is obtained by doping different compounds in the stated weight ratios.
TABLE 1 Electron transport layer structures of device examples and comparative examples
The material structure used in the device is as follows:
for the organic light emitting devices manufactured using the methods of the above examples and comparative examples, at 10mA/cm2The maximum wavelength λ max and the External Quantum Efficiency (EQE) were measured at a current density of 80mA/cm2The lifetime was measured at the current density of (LT 97). To more clearly show the comparison of the data, the EQE data and LT97 data of comparative example 1 were set to 100%, while the EQE and LT97 data of examples 1 and 2 were scaled with respect to the corresponding data of comparative example 1, and the related data and scaling results are shown in table 2.
TABLE 2 device data
Discussion:
as can be seen from the data in table 2, the examples exhibited improved efficiency and life as compared with comparative example 1 and comparative example 2, and particularly exhibited excellent characteristics in terms of life, which were 12.3% higher than comparative example 1 and 9.1% higher than comparative example 2. The above data demonstrate the advantages of the disclosed compounds containing deuterium atoms having the structure of formula 1 compared to compounds that do not contain deuterium atoms for use in the electron transport layer of an organic light emitting device.
It should be understood that the various embodiments described herein are illustrative only and are not intended to limit the scope of the invention. Thus, the invention as claimed may include variations from the specific embodiments and preferred embodiments described herein, as will be apparent to those skilled in the art. Many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the present invention. It should be understood that various theories as to why the invention works are not intended to be limiting.
Claims (13)
1. A compound having a structure represented by formula 1:
wherein the content of the first and second substances,
ring X and ring Y are each independently selected from an aromatic ring having 5 to 30 ring atoms or a heteroaromatic ring having 5 to 30 ring atoms;
Z1-Z4each independently selected from CRzOr N;
Rxand RyThe same or different at each occurrence denotes mono-, poly-or no-substitution;
Rx、Ryand RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aralkyl, or aralkyl, and others, aralkyl, and others, aralkyl, and othersAn alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents Rx，RyCan optionally be linked to form a ring;
L1and L2Each occurrence, the same or different, is selected from the group consisting of: a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and combinations thereof;
ar is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;
r is selected from substituted alkyl having 1 to 20 carbon atoms, substituted cycloalkyl having 3 to 20 carbon atoms, substituted aryl having 6 to 30 carbon atoms, substituted heteroaryl having 3 to 30 carbon atoms, or combinations thereof; and said R contains at least one deuterium atom.
2. The compound of claim 1, wherein ring X and ring Y are each independently selected from an aromatic ring having 6-18 ring atoms or a heteroaromatic ring having 5-18 ring atoms;
preferably, ring X and ring Y are each independently selected from a benzene, naphthalene, phenanthrene, anthracene, fluoranthene, pyridine or pyrazine ring;
more preferably, ring X and ring Y are each independently selected from benzene rings.
3. The compound of claim 1 or 2, wherein Ar is selected from substituted or unsubstituted aryl having 6 to 18 carbon atoms, or substituted or unsubstituted heteroaryl having 3 to 18 carbon atoms;
preferably, Ar is selected from the group consisting of: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, pyrenyl, fluoranthenyl, 9, 9-dimethylfluorenyl, spirobifluorenyl, pyridyl, quinolinyl, phenanthrolinyl, 9, 9-dimethylazafluorenyl, dibenzofuranyl, dibenzothiophenyl, and combinations thereof.
4. The compound of claim 3, wherein Ar is selected from any one of the group consisting of the following structures:
5. the compound of any one of claims 1-4, wherein L1And L2Each independently selected from a single bond or any of the group consisting of:
wherein R isaThe same or different at each occurrence denotes mono-, poly-or unsubstituted;
Raeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted cycloalkyl having 1 to 20 carbon atomsA heteroalkyl group of a subgroup, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent substituents RaCan optionally be linked to form a ring;
preferably, L1And L2Each independently selected from a single bond or phenylene.
6. The compound of any one of claims 1-5, wherein R is selected from substituted alkyl having 1-20 carbon atoms, substituted cycloalkyl having 3-20 carbon atoms, substituted aryl having 6-25 carbon atoms, substituted heteroaryl having 3-25 carbon atoms, or a combination thereof; and said R comprises at least one of D, CD2Or CD3；
Preferably, R is selected from the group consisting of: deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated butyl, deuterated isobutyl, deuterated tert-butyl, deuterated pentyl, deuterated hexyl, deuterated heptyl, deuterated octyl, deuterated nonyl, deuterated cyclopropyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated phenyl, deuterated naphthyl, deuterated pyridyl, deuterated fluorenyl, deuterated spirobifluorenyl, deuterated dibenzofuranyl, deuterated dibenzothiophenyl, deuterated carbazolyl, and combinations thereof.
7. The compound of claim 6, wherein R is selected from any one of the group consisting of R1 through R100:
8. the compound of any one of claims 1-7, wherein Z is1-Z4Each independently selected from CRz，RzEach occurrence, identically or differently, is selected from: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, or a combination thereof;
preferably, RzSelected from hydrogen or deuterium, the same or different at each occurrence.
9. The compound of claim 1, wherein the compound is selected from the group consisting of compound 1 to compound 217:
10. an electroluminescent device, comprising:
an anode, a cathode, a anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having a structure represented by formula 1:
wherein the content of the first and second substances,
ring X and ring Y are each independently selected from an aromatic ring having 5 to 30 ring atoms or a heteroaromatic ring having 5 to 30 ring atoms;
Z1-Z4each independently selected from CRzOr the number of N is greater than the number of N,
Rxand RyThe same or different at each occurrence denotes mono-, poly-or no-substitution;
Rx、Ryand RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent substituents Rx，RyCan optionally be linked to form a ring;
L1and L2Each occurrence, the same or different, is selected from the group consisting of: single bond, substituted or unsubstituted alkylene having 1 to 20 carbon atomsA substituted or unsubstituted cycloalkylene group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and combinations thereof;
ar is selected from substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms;
r is selected from substituted alkyl having 1 to 20 carbon atoms, substituted cycloalkyl having 3 to 20 carbon atoms, substituted aryl having 6 to 30 carbon atoms, substituted heteroaryl having 3 to 30 carbon atoms, or combinations thereof; and said R contains at least one deuterium atom.
11. The device of claim 10, wherein the organic layer is an electron transport layer and the compound is an electron transport material.
12. The device of claim 11, wherein the electron transport layer further comprises at least one material;
preferably, wherein the electron transport layer further comprises at least one metal complex;
more preferably, wherein the metal complex comprises a ligand L represented by formula 2a：
Wherein Q1To Q6Each independently selected from CRqOr N; rqEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, substituted or unsubstituted silyl having 3 to 20 carbon atoms, cyano, substituted or unsubstituted aryl having 6 to 30 carbon atoms and substituted or unsubstitutedSubstituted heteroaryl having 3 to 30 carbon atoms;
wherein W is selected from NRNO, S or Se;
RNeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
most preferably wherein the metal complex is selected from 8-hydroxyquinoline-lithium, 8-hydroxyquinoline-sodium, 8-hydroxyquinoline-potassium, bis (8-hydroxyquinoline) -beryllium, bis (8-hydroxyquinoline) -magnesium, bis (8-hydroxyquinoline) -calcium, tris (8-hydroxyquinoline) -boron, tris (8-hydroxyquinoline) -aluminum, or tris (8-hydroxyquinoline) -gallium.
13. A compound formulation comprising a compound of any one of claims 1-9.
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