CN112151682B - Organic electroluminescent device comprising hole blocking layer and electron transport layer - Google Patents
Organic electroluminescent device comprising hole blocking layer and electron transport layer Download PDFInfo
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- CN112151682B CN112151682B CN201910547378.6A CN201910547378A CN112151682B CN 112151682 B CN112151682 B CN 112151682B CN 201910547378 A CN201910547378 A CN 201910547378A CN 112151682 B CN112151682 B CN 112151682B
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- 230000000903 blocking effect Effects 0.000 title abstract description 54
- 239000010410 layer Substances 0.000 claims abstract description 160
- 239000000463 material Substances 0.000 claims abstract description 88
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 239000012044 organic layer Substances 0.000 claims abstract description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims description 264
- -1 amino, silyl Chemical group 0.000 claims description 68
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 50
- 125000001424 substituent group Chemical group 0.000 claims description 29
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 229910052805 deuterium Inorganic materials 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
- 125000004122 cyclic group Chemical group 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 19
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 19
- 125000002252 acyl group Chemical group 0.000 claims description 18
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 18
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 18
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 17
- 125000005104 aryl silyl group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 238000006467 substitution reaction Methods 0.000 claims description 16
- 125000004149 thio group Chemical group *S* 0.000 claims description 16
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 14
- 125000004185 ester group Chemical group 0.000 claims description 14
- 150000002527 isonitriles Chemical class 0.000 claims description 13
- 150000002825 nitriles Chemical class 0.000 claims description 12
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 12
- 125000000732 arylene group Chemical group 0.000 claims description 11
- 125000005549 heteroarylene group Chemical group 0.000 claims description 11
- 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 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000006413 ring segment Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 239000003446 ligand Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 230000002950 deficient Effects 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 150000004696 coordination complex Chemical class 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 229910052711 selenium Inorganic materials 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 229960003540 oxyquinoline Drugs 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([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
- 125000005580 triphenylene group Chemical group 0.000 claims description 4
- 239000002019 doping agent Substances 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 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
- 229910052796 boron Inorganic materials 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
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical group [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 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
- 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
- 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
- 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
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 239000000969 carrier Substances 0.000 abstract description 2
- 230000001105 regulatory effect Effects 0.000 abstract description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 12
- 239000007924 injection Substances 0.000 description 10
- 238000002347 injection Methods 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 230000003111 delayed effect Effects 0.000 description 9
- 230000005525 hole transport Effects 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
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-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
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 238000005538 encapsulation Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 230000000670 limiting effect Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
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- 150000002894 organic compounds Chemical class 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
- 229910000085 borane Inorganic materials 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N isonitrile group Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-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
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 2
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical compound C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-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
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-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
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 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 compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 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
- 150000001716 carbazoles Chemical class 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000010586 diagram Methods 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000005281 excited state Effects 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
- 238000010348 incorporation Methods 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
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000002346 layers by function 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 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
- 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
- 230000036961 partial effect Effects 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical group C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000002210 silicon-based material Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- HMLURENDJQQGCM-UHFFFAOYSA-N 1-benzothiophene;pyridine Chemical compound C1=CC=NC=C1.C1=CC=C2SC=CC2=C1 HMLURENDJQQGCM-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004134 1-norbornyl group Chemical group [H]C1([H])C([H])([H])C2(*)C([H])([H])C([H])([H])C1([H])C2([H])[H] 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- IEBQZJXMAOMNBO-UHFFFAOYSA-N 1h-indole;pyridine Chemical compound C1=CC=NC=C1.C1=CC=C2NC=CC2=C1 IEBQZJXMAOMNBO-UHFFFAOYSA-N 0.000 description 1
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- 125000005810 2,5-xylyl group Chemical group [H]C1=C([H])C(=C(*)C([H])=C1C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- SFFSGPCYJCMDJM-UHFFFAOYSA-N 2-[2-(3-oxo-1,2-benzoselenazol-2-yl)ethyl]-1,2-benzoselenazol-3-one Chemical compound [se]1C2=CC=CC=C2C(=O)N1CCN1C(=O)C(C=CC=C2)=C2[se]1 SFFSGPCYJCMDJM-UHFFFAOYSA-N 0.000 description 1
- 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006481 2-iodobenzyl group Chemical group [H]C1=C([H])C(I)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical group C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
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- 108091008695 photoreceptors Proteins 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
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- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Engineering & Computer Science (AREA)
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- Spectroscopy & Molecular Physics (AREA)
- Inorganic Chemistry (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
An organic electroluminescent device comprising a hole blocking layer and an electron transport layer is disclosed. The device comprises an anode, a cathode and an organic layer arranged between the anode and the cathode, wherein the organic layer at least comprises a first organic layer and a second organic layer, and the first organic layer and the second organic layer both comprise compounds with specific structures. By selecting the special combination of the hole blocking layer and the electron transport layer containing the specific structural materials, the concentration of carriers in the light-emitting layer is effectively regulated and controlled to reach the expected balance, and compared with the prior art, the comprehensive performance of the organic electroluminescent device is obviously improved. A display assembly is also disclosed.
Description
Technical Field
The present invention relates to an organic electronic device. And more particularly, to an organic electroluminescent device including a hole blocking layer and an electron transport layer.
Background
Organic electronic devices include, but are not limited to, the following: organic Light Emitting Devices (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLEDs), organic photovoltaic devices (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 electroluminescent devices.
The organic light emitting device has advantages of wide-angle, high contrast, and faster response time. An organic light emitting device, an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as electron transport and light emitting layers were reported by Tang and Van Slyke, islamic in 1987 (Applied Physics Letters,1987,51 (12): 913-915). Once biased into the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). Because OLEDs are self-emitting solid state devices, they offer 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 flexible substrate fabrication.
The organic electroluminescent device converts electric energy into light by applying a voltage across the device. In general, an organic electroluminescent device includes an anode, a cathode, and an organic layer between the anode and the cathode. The organic layer of the organic electroluminescent device may include a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like. The materials constituting the organic layer may be classified into a hole injecting material, a hole transporting material, an electron blocking material, a light emitting material, an electron buffering material, a hole blocking material, an electron transporting material, a hole blocking material, and the like according to the functions of the materials. When a bias is applied to the device, holes are injected from the anode to the light emitting layer and electrons are injected from the cathode to the light emitting layer. The holes and electrons meet to form excitons, which recombine to emit light.
The hole blocking layer and the electron transport layer are important functional layers affecting the performance of the organic electroluminescent device, and the selection and collocation of materials seriously affect the driving voltage, efficiency and service life of the organic electroluminescent device. It is commercially desirable to obtain an organic electroluminescent device with characteristics of low driving voltage, high efficiency, long service life, etc., and it is important to develop a novel material for a hole blocking layer and an electron transport layer, and to select a suitable combination of the hole blocking layer and the electron transport layer for achieving the above-mentioned objects.
The US patent application US20190067591A1 discloses a series of compounds having an azacyclic structure such as triazine as a basic skeleton as a hole blocking material, and the inventors of this application noted matching of these hole blocking materials with specific electron transporting materials having an azacyclic structure such as triazine as a basic skeleton as well, but did not study the matching of such compounds as hole blocking materials with other specific structural types, particularly electron transporting materials containing silicon heterocycles.
Chinese patent application CN 109671851A discloses a series of carbazole compounds that can be used as hole blocking materials, but the application only researches the combination of such compounds with three common electron transport materials, and does not study the coordination of carbazole compounds as hole blocking materials with electron transport materials of specific structures.
U.S. patent No. 9960363B2 discloses compounds which can be used as hole blocking materials, the basic backbone of which is formed by the attachment of a fluorene moiety to a six-membered aza-aromatic ring, either directly or via a linking group, but this application does not contemplate the coordination of such compounds as hole blocking materials to electron transport materials of specific structure.
Chinese patent application CN201811235650.9 is a patent application prior to the present inventors, the entire contents of which are incorporated herein by reference. Although this application discloses a series of silicon-containing compounds as electron transport layer materials, this application does not contemplate the incorporation of the silicon-containing compound as an electron transport layer material with a hole blocking layer material of a particular structure.
Chinese patent application CN201910149767.3 is a patent application prior to the present inventors, the entire contents of which are incorporated herein by reference. Although this application discloses a series of organic compounds that can be used as hole blocking layer materials, the application does not contemplate the incorporation of an organic compound as a hole blocking layer material with an electron transport layer material of a particular structure.
Through intensive researches, the inventor discovers that the compound with the structure of the formula 1 is used as a hole blocking layer material and the compound with the structure of the formula 2 is used as an electron transport layer material, and the two materials are matched and jointly applied to the organic electroluminescent device, so that the comprehensive performance of the organic electroluminescent device can be obviously improved.
Disclosure of Invention
One of the objects of the present invention is to provide an organic electroluminescent device comprising: the anode, the cathode and the organic layer arranged between the anode and the cathode, wherein the organic layer at least comprises an organic layer I and an organic layer II;
wherein the organic layer comprises a compound having a structure represented by formula 1:
in the formula 1, the components are mixed,
wherein X is independently selected from NR ', CR ' R ', O, S or Se;
wherein R ', R "and R'" are each independently 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 arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amine having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid groups, ester groups, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof;
When X is CR "R '", R "and R'" can optionally be linked to form a ring;
wherein X is a1 To X a8 Each independently is CR 1 Or N; wherein X is a1 -X a8 At least one of them is CR 1 And R is 1 Is a structure represented by formula 1A:
in formula 1A, the CR is represented by 1 R is described in the structure 1 A position connected to C;
wherein L' is a single bond, or is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or is a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;
wherein Ar is 1 And Ar is a group 2 Each independently selected from the group consisting of: substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, and combinations thereof;
wherein X is a1 To X a8 The remainder of R present in 1 Each independently 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 arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amine having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid groups, ester groups, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Two adjacent substituents R 1 Can optionally be linked to form a ring;
wherein the second organic layer comprises a compound having a structure represented by formula 2:
in the formula 2, the components are mixed,
wherein n is 1,2,3 or 4; when n is 2 or more, each group L and B may be the same or different;
wherein L is a single bond, or is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or is a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;
wherein B is a substituted or unsubstituted electron-deficient heteroaryl group having 2 to 60 carbon atoms;
wherein a is a structure represented by formula 2A:
in the formula (2A),
wherein ring D and ring E each independently represent a substituted or unsubstituted aryl group having 5 to 50 ring atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;
wherein at least one of ring D and ring E is a fused ring system;
wherein R is 2 And R is 2A Each independently 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 arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amine having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid groups, ester groups, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof;
R 2 And R is 2A Can optionally be linked to form a ring.
The second object of the present invention is to provide a display device, which includes the organic electroluminescent device.
In the organic electroluminescent device disclosed in the present invention, an organic compound having a structure of formula 2 is used in combination as an electron transport layer and an organic compound having a structure of formula 1 is used as a hole blocking layer. By selecting a specific combination of the hole blocking layer and the electron transport layer containing specific structural materials, the concentration of carriers in the light-emitting layer is effectively regulated to achieve the desired balance, and compared with the prior art, the organic electroluminescent device has the advantages of obviously improving the comprehensive performance of the organic electroluminescent device, and being particularly more advantageous in the field of commercial application.
Drawings
Fig. 1 is a schematic view of a conventional organic light emitting device.
Fig. 2 is a schematic diagram of a conventional tandem organic light emitting device.
Fig. 3 is a schematic diagram of another conventional tandem organic light emitting device.
Detailed Description
OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically illustrates, without limitation, an organic light-emitting device 100. The drawings are not necessarily to scale, and some of the layer structures in the drawings 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, a light emitting 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 layers described. The nature and function of the layers and exemplary materials are described in more detail in U.S. patent US7,279,704B2, columns 6-10, the entire contents of which are incorporated herein by reference.
There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. patent 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 in a 50:1 molar ratio 4 m-MTDATA of TCNQ 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. Pat. 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 in 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. Examples of cathodes are disclosed in U.S. Pat. nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, including composite cathodes having a thin layer of metal, such as Mg: ag, with an overlying transparent, electrically conductive, sputter deposited ITO layer. 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 implant layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.
The above-described hierarchical structure is provided by way of non-limiting example. The function of the OLED may be achieved by combining the various layers described above, or some of the 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 sublayers. 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.
In one embodiment, two or more OLED cells can be connected in series to form a tandem OLED, as schematically illustrated, but not limited to, in FIG. 2, a tandem organic light-emitting device 500. The device 500 may include a substrate 101, an anode 110, a first unit organic light emitting device 100, a charge generation layer 300, a second unit organic light emitting device 200, and a cathode 290. The first unit 100 includes a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light emitting layer 150, a hole blocking layer 160, and an electron transport layer 170, the second unit 200 includes a hole injection layer 220, a hole transport layer 230, an electron blocking layer 240, a light emitting layer 250, a hole blocking layer 260, an electron transport layer 270, and an electron injection layer 280, and the charge generation layer 300 includes an N-type charge generation layer 310 and a P-type charge generation layer 320. The device 500 may be fabricated by sequentially depositing the layers described.
The OLED may also be provided with an encapsulation layer, such as schematically, non-limitingly, an organic light emitting device 600 is shown in fig. 3, which, unlike fig. 2, may further comprise an encapsulation layer 102 over the cathode 290 to prevent 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 an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film packages are 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 a variety of 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 or signaling, heads-up displays, displays that are fully or partially transparent, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smartwatches, laptops, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and taillights.
The materials and structures described herein may also be used in other organic electronic devices as listed above.
As used herein, "top" means furthest from the substrate and "bottom" means closest to the substrate. In the case where the first layer is described as being "disposed" on "the second layer, the first layer is disposed farther from the substrate. Unless a first layer is "in contact with" a second layer, other layers may be present between the first and second layers. For example, a cathode may be described as "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 "photosensitive" when it is believed that the ligand directly contributes to the photosensitive properties of the emissive material. When it is believed that the ligand does not contribute to the photosensitive properties of the emissive material, the ligand may be referred to as "ancillary," but ancillary ligands may alter the properties of the photosensitive ligand.
It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by spin statistics that delay fluorescence by more than 25%. Delayed fluorescence can be generally classified into two types, i.e., P-type delayed fluorescence and E-type delayed fluorescence. The P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).
On the other hand, the E-type delayed fluorescence does not depend on the collision of two triplet states, but on the transition between the triplet states and the singlet excited state. Compounds capable of generating E-type delayed fluorescence need to have very small mono-triplet gaps in order for the conversion between the energy states. The thermal energy may activate a 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 delay component increases with increasing temperature. The fraction of backfill singlet excited states may reach 75% if the reverse intersystem crossing (iric) rate is sufficiently fast to minimize non-radiative decay from the triplet states. The total singlet fraction may be 100%, well in excess of 25% of the spin statistics of the electrically generated excitons.
Type E delayed fluorescence features can be found in excitation complex systems or in single compounds. Without being bound by theory, it is believed that E-delayed fluorescence requires a luminescent material with a small mono-triplet energy gap (Δe S-T ). Organic non-metal containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor Charge Transfer (CT) type emission. The spatial separation of HOMO from LUMO in these donor-acceptor compounds generally results in a small Δe S-T . These states may include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) to an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).
Definition of terms for substituents
Halogen or halide-as used herein, includes fluorine, chlorine, bromine and iodine.
Alkyl-includes straight and branched 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 carbon 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 preferred.
Cycloalkyl-as used herein, includes cyclic alkyl. Preferred cycloalkyl groups are cycloalkyl groups containing 4 to 10 ring carbon atoms, including cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. In addition, cycloalkyl groups may be optionally substituted. The carbon in the ring may be substituted with other heteroatoms.
Alkenyl-as used herein, covers both straight chain and branched alkene groups. Preferred alkenyl groups are alkenyl groups containing 2 to 15 carbon atoms. Examples of alkenyl groups include vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, 1-methylvinyl, styryl, 2-diphenylvinyl, 1-methallyl, 1-dimethylallyl, 2-methallyl, 1-phenylallyl, 2-phenylallyl, 3-diphenylallyl, 1, 2-dimethylallyl, 1-phenyl-1-butenyl and 3-phenyl-1-butenyl. In addition, alkenyl groups may be optionally substituted.
Alkynyl-as used herein, covers both straight and branched chain alkynyl groups. 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, encompass both non-fused and fused systems. 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, chicory, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, aryl groups may be optionally substituted. Examples of non-condensed aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-3-yl, p-triphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p- (2-phenylpropyl) phenyl, 4 '-methylbiphenyl-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-tetrabiphenyl.
Heterocyclyl or heterocycle-as used herein, encompasses both aromatic and non-aromatic cyclic groups. 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 the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom and a selenium atom.
Heteroaryl-as used herein, encompasses non-fused and fused heteroaromatic groups that may contain 1 to 5 heteroatoms. Preferred heteroaryl groups are those containing 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms, and even more preferably 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, oxazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzothiophene pyridine, thienodipyridine, benzothiophene bipyridine, benzoselenophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-aza-1, 3-aza-borane, 1-borane, 4-borane, and the like. In addition, heteroaryl groups may be optionally substituted.
Alkoxy-is represented by-O-alkyl. Examples of alkyl groups and preferred examples are the same as described above. Examples of the alkoxy group having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms include methoxy, ethoxy, propoxy, butoxy, pentoxy and hexoxy groups. 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 phenoxy and diphenoxy.
Aralkyl-as used herein, an alkyl group having an aryl substituent. In addition, aralkyl groups may be optionally substituted. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α -naphthylmethyl, 1- α -naphthyl-ethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthyl-ethyl, 2- β -naphthyl-ethyl, 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-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-chlorophenyl, 1-isopropyl and 1-isopropyl. Among the above, preferred are benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl.
The term "aza" in aza-dibenzofurans, aza-dibenzothiophenes and the like means that one or more C-H groups in the corresponding aromatic fragment are replaced by nitrogen atoms. 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 will be readily apparent to those of ordinary skill in the art, and all such analogs are intended to be included in the terms described herein.
In the present disclosure, when any one of the terms from 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 amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, refers to any one of alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino groups, which may be substituted with one or more groups selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted aralkyl having 7 to 30 carbon atoms, unsubstituted aralkyl having 1 to 20 carbon atoms, unsubstituted alkoxy having 6 to 20 carbon atoms, unsubstituted alkenyl having 3 to 30 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted alkenyl having 3 to 30 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 30 carbon atoms, and substituted aryl having 3 to 30 carbon atoms, and the carbonyl having 3 carbon atoms.
It will be appreciated that when a fragment of a molecule is described as a substituent or otherwise attached to another moiety, its name may be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to 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 equivalent.
In the compounds mentioned in this disclosure, the hydrogen atoms 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 of their enhanced efficiency and stability of the device.
In the compounds mentioned in this disclosure, polysubstituted means inclusive of disubstituted up to the maximum available substitution range. When a substituent in a compound mentioned in this disclosure means multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), it means that the substituent may be present at a plurality of available substitution positions on its linking structure, and the substituent present at each of the plurality of available substitution positions may be of the same structure or of different structures.
In the compounds mentioned in this disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless explicitly defined, for example, adjacent substituents can optionally be linked to form a ring. In the compounds mentioned in this disclosure, where adjacent substituents can optionally be joined to form a ring, the ring formed may be monocyclic or polycyclic, as well as alicyclic, heteroalicyclic, aromatic or heteroaromatic. 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 further distant carbon atoms. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and 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 be taken 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:
Furthermore, the expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that, in the case where one of the two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:
according to an embodiment of the present invention, an organic electroluminescent device is disclosed, comprising:
an anode is provided with a cathode,
a cathode electrode, which is arranged on the surface of the cathode,
and an organic layer disposed between the anode and the cathode, the organic layer comprising at least a first organic layer and a second organic layer;
wherein the organic layer comprises a compound having a structure represented by formula 1:
in the formula 1, the components are mixed,
wherein X is independently selected from NR ', CR ' R ', O, S or Se;
wherein R ', R "and R'" are each independently 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 arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amine having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid groups, ester groups, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof;
When X is CR "R '", R "and R'" can optionally be linked to form a ring;
wherein X is a1 To X a8 Each independently is CR 1 Or N;
wherein X is a1 -X a8 At least one of them is CR 1 And said R is 1 Is a structure represented by formula 1A:
in formula 1A, the CR is represented by 1 R is described in the structure 1 A position connected to C;
wherein L' is a single bond, or is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or is a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;
wherein Ar is 1 And Ar is a group 2 Each independently selected from the group consisting of: substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, and combinations thereof;
wherein X is a1 -X a8 The remainder of R present in 1 (i.e., R other than the structure represented by formula 1A 1 ) Each independently 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 having 1 to 20 carbon atomsSubstituted or unsubstituted aryloxy groups having from 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having from 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having from 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having from 6 to 20 carbon atoms, substituted or unsubstituted amine groups having from 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;
Two adjacent substituents R 1 Can optionally be linked to form a ring;
wherein the second organic layer comprises a compound having a structure represented by formula 2:
in the formula 2, the components are mixed,
wherein n is 1,2,3 or 4; when n is 2 or more, each group L and B may be the same or different;
wherein L is a single bond, or is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or is a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;
wherein B is a substituted or unsubstituted electron-deficient heteroaryl group having 2 to 60 carbon atoms;
wherein a is a structure represented by formula 2A:
in the formula (2A),
wherein ring D and ring E each independently represent a substituted or unsubstituted aryl group having 5 to 50 ring atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;
wherein at least one of ring D and ring E is a fused ring system;
wherein R is 2 And R is 2A Each independently 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 arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amine having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid groups, ester groups, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof;
R 2 And R is 2A Can optionally be linked to form a ring;
in this embodiment, X in formula 1 a1 -X a8 At least one (or more) of them is CR 1 And X is a1 -X a8 R present in (a) 1 It is satisfied that at least one (or one) is a structure represented by formula 1A. X is X a1 -X a8 The remainder of R present in 1 It is not required to have the structure represented by formula 1A, and may be each independently 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 atomsArylsilane groups of 6 to 20 carbon atoms, substituted or 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, phosphine groups, and combinations thereof.
According to one embodiment of the invention, the organic layer arranged between the anode and the cathode further comprises at least one light emitting layer.
According to one embodiment of the invention, the light emitting layer comprises at least one host material and at least one doping material.
According to one embodiment of the invention, the doping material is selected from a fluorescent light emitting material, a phosphorescent light emitting material or a thermally excited time lapse fluorescent material.
According to one embodiment of the invention, the emission wavelength of the device is between 300nm and 1200 nm.
According to one embodiment of the invention, the organic layer is further from the anode than the light emitting layer, and the second organic layer is further from the anode than the first organic layer.
According to one embodiment of the invention, the thickness of the first organic layer is between 0.1nm and 40nm and/or the thickness of the second organic layer is between 0.1nm and 50 nm.
According to one embodiment of the invention, the second organic layer further comprises at least one further material.
According to one embodiment of the present invention, wherein the second organic layer further comprises at least another material, the another material is a metal complex, and the metal complex comprises a compound represented by formula L q Represented ligand L q ：
L (L) q In (1), Y 1 ，Y 2 ，Y 3 ，Y 4 ，Y 5 And Y 6 Each independently selected from CR Y Or N; wherein each R is Y Each independently selected from hydrogen, deuterium, alkyl, alkoxy, amino, silyl, cyano, halogenAryl and heteroaryl;
wherein Z is NH, O, S or Se;
according to one embodiment of the invention, wherein the organic layer two further comprises at least one metal complex 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, or tris (8-hydroxyquinoline) -gallium.
According to one embodiment of the invention, wherein R ', R "and R'" in formula 1 are each independently selected from substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms.
According to one embodiment of the invention, wherein R ', R "and R'" in formula 1 are each independently selected from the group consisting of: biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, dibenzofuranyl.
According to one embodiment of the present invention, in the formula 1, the X a1 -X a8 The remainder of R present in 1 (i.e., R other than the structure represented by formula 1A 1 ) Each independently selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.
According to one embodiment of the present invention, in the formula 1, the X a1 -X a8 The remainder of R present in 1 (i.e., R other than the structure represented by formula 1A 1 ) Each independently selected from the group consisting of: hydrogen, deuterium, phenyl, biphenyl and terphenyl.
According to one embodiment of the present invention, X in formula 1 a7 Is CR (CR) 1 And said R is 1 Is a structure represented by formula 1A.
According to one embodiment of the present invention, in formula 1, ar 1 And Ar is a group 2 Each independently selected from phenyl, biphenyl or terphenyl.
According to one embodiment of the present invention, in the formula 1, ar is 1 And Ar is a group 2 Middle toAt least one is biphenyl or terphenyl.
According to an embodiment of the present invention, the compound of the structure represented by formula 1 is selected from the group consisting of:
in this embodiment of the present invention, in one embodiment,respectively represent-> The same is true of the representation of other structures in this embodiment.
According to an embodiment of the invention, wherein the hydrogen in all specific compounds shown in the previous embodiment can be partially or completely replaced by deuterium.
According to one embodiment of the invention, in formula 1, L' is a single bond, or is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or is a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.
According to one embodiment of the invention, at least one of ring D and ring E in formula 2A is a fused ring system, and the fused ring system is at least two aryl and/or heteroaryl rings fused together to form a fused ring system comprising at least 10 carbon atoms, or a fused ring system comprising at least 10 in total of both carbon and nitrogen atoms.
According to one embodiment of the invention, at least one of ring D and ring E in formula 2A is a fused ring system, and the fused ring system is at least three aryl and/or heteroaryl rings fused together to form a fused ring system comprising at least 14 carbon atoms, or a fused ring system comprising at least 14 in total of both carbon and nitrogen atoms.
According to one embodiment of the present invention, a in the formula 2 is selected from the group consisting of formula 3 to formula 33:
wherein T is 1 To T 22 Each independently selected from CR T C, or N;
wherein each R is T Each independently 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 Substituted 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 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;
in formulas 3 to 33, adjacent substituents can optionally be linked to form a ring.
In this embodiment, when T 1 To T 22 When C is selected, it means that L in formula 2 is linked to A through this position.
According to one embodiment of the present invention, A in formula 2 is independently selected from the group consisting of A 1 To A 298 And (3) a group consisting of:
according to one embodiment of the invention, L in formula 2 is independently selected from the group consisting of a single bond, and formulas 34-58:
wherein R is 3 ,R 4 ,R 5 And R is 6 Each independently represents mono-substituted, poly-substituted or unsubstituted; when they represent multiple substitutions, adjacent substitutions can optionally be joined to form a ring;
wherein R is 3 ,R 4 ,R 5 And R is 6 Each independently 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 aryl having 7 to 30 carbon atoms Alkyl, 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 arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amine having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.
According to one embodiment of the invention, L in formula 2 is independently selected from the group consisting of single bonds L 0 L is as follows 1 -L 58 A group of groups. Wherein L is 1 -L 58 The specific structure of (2) is as follows:
according to one embodiment of the present invention, B in formula 2 is independently selected from the group consisting of formulas 59 to 63:
wherein X is 1 To X 6 Each independently selected from CR x C, O, S, N or NR x ’，
Wherein X is 1 To X i At least one of which is N, or wherein X 1 To X i At least two of which are N, or X 1 To X i At least three of which are N; the X is i Corresponds to the X 1 To X 6 The largest sequence number exists in the formulas 59 to 63; for example, for formula 59, the X i Corresponds to the X 1 To X 6 The number X with the largest number in formula 59 3 . Namely, X in formula 59 1 To X 3 At least one of which is N, or X in formula 59 1 To X 3 At least two of which are N, or X in formula 59 1 To X 3 Three of which are N.
Wherein R is 7 Each independently represents mono-substituted, poly-substituted or unsubstituted; when they represent multiple substitutions, adjacent substitutions can optionally be joined to form a ring;
wherein R is 7 ,R x, And R is x ' each independently 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 arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amine having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid groups, ester groups, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.
According to one embodiment of the invention, B in formula 2 is independently selected from the group consisting of B1-B105:
according to one embodiment of the invention, the compound has the structure of formula 2, wherein A is selected from the group consisting of A 1 -A 298 The B's are each independently selected from the group consisting of B 1 -B 105 The L is each independently selected from the group consisting of L 0 -L 58 A group of groups. A is that 1 -A 298 ，B 1 -B 91 ，L 0 -L 58 See the previous embodiments for specific configurations.
According to one embodiment of the invention, in formula 2, wherein ring D and ring E each independently represent a substituted or unsubstituted aryl or heteroaryl group having 5 to 40 ring atoms, or wherein ring D and ring E each independently represent a substituted or unsubstituted aryl or heteroaryl group having 5 to 30 ring atoms, or wherein ring D and ring E each independently represent a substituted or unsubstituted aryl or heteroaryl group having 5 to 20 ring atoms.
According to one embodiment of the invention, in formula 2, wherein each L is independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms, a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms; or each L is independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 40 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms; each L is independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms; l is each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.
According to one embodiment of the invention, in formula 2, B is each independently selected from a substituted or unsubstituted electron-deficient heteroaryl group having 2 to 50 carbon atoms, or B is each independently selected from a substituted or unsubstituted electron-deficient heteroaryl group having 2 to 40 carbon atoms, B is each independently selected from a substituted or unsubstituted electron-deficient heteroaryl group having 2 to 30 carbon atoms, and B is each independently selected from a substituted or unsubstituted electron-deficient heteroaryl group having 2 to 20 carbon atoms.
According to one embodiment of the invention, the substituent R in formula 2A 2 And R is 2A Are not connected to form a ring.
According to one embodiment of the present invention, in the structures represented by formulas 3 to 33, T 5 And T 6 Are not connected to form a ring.
According to another embodiment of the present invention, a display assembly is also disclosed, which includes an organic electroluminescent device. The specific structure of the organic electroluminescent device is described in any of the above embodiments.
Combined with other materials
The materials described herein for specific 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 2016/0359122A1, paragraphs 0132-0161, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that may be used in combination with the materials 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 useful for specific layers in an organic light emitting device may be used in combination with a variety of other materials present in the device. For example, the electron transport layers and hole blocking layers disclosed herein are used in combination with other various transport layers, light emitting layers, blocking 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. 2015/0349273A1, paragraphs 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that may be used in combination with the materials disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
The method of manufacturing the organic electroluminescent device is not limited, and the method of manufacturing the following examples is only one example and should not be construed as limiting. Those skilled in the art will be able to make reasonable modifications to the preparation methods of the following examples in light of the prior art. The proportions of the various materials in the organic layers in the organic electroluminescent device are not particularly limited, and those skilled in the art can reasonably select a certain range according to the prior art, for example, taking an electron transport layer as an example, and taking the total weight of the materials in the layer as a reference, the compound with the structure represented by formula 2 can occupy 10% -100%; alternatively, the compound having the structure represented by formula 2 may account for 20% to 70%; alternatively, the compound having the structure represented by formula 2 may account for 30% -50%. The thickness of each organic layer in the organic electroluminescent device is not particularly limited, and may be reasonably selected within a certain range by those skilled in the art according to the prior art, for example, the hole blocking layer thickness may be between 0.1nm and 40nm, or may be between 1nm and 30nm, or may be between 2nm and 20 nm. For another example, the electron transport layer thickness may be between 0.1nm and 50nm, or may be between 1nm and 45nm, or may be between 5nm and 40 nm. The characteristics of the light emitting device prepared in the examples were tested using equipment conventional in the art, in a manner well known to those skilled in the art. Since those skilled in the art are aware of the relevant contents of the device usage and the testing method, and can obtain the intrinsic data of the sample certainly and uninfluenced, the relevant contents are not further described in this patent.
Example 1-1: an organic electroluminescent device comprising the material combination of the invention was prepared.
First, a glass substrate having an 80nm thick Indium Tin Oxide (ITO) anode was cleaned, and then treated with UV ozone and oxygen plasma. After the treatment, the substrate was baked in a glove box filled with nitrogen gas to remove moisture, and then mounted on a substrate holder and loadedIn the vacuum chamber. The organic layer specified below was at a vacuum level of about 10 -8 In the case of Torr Is evaporated on the ITO anode in sequence by thermal vacuum. The compound HI was used as a Hole Injection Layer (HIL) with a thickness ofThe compound HT is used as a Hole Transport Layer (HTL) with a thickness of +.>Compound EB is used as Electron Blocking Layer (EBL) with thickness +.>Compound Host1 as Host material, compound D1 as dopant, both co-deposited for use as light emitting layer (EML), dopant D1 accounting for 4% of the total weight of the light emitting layer material, thickness +.>Above EML, compound 2-2-2 is used as Hole Blocking Layer (HBL) with thickness +.>On HBL, compound A 30 L 0 B 52 And a compound EI is co-deposited as an Electron Transport Layer (ETL), wherein the compound EI accounts for 60% of the total weight of the electron transport layer material, and the ETL has a thickness of +.>Finally, vapor deposition->Thickness of the compound EI as Electron Injection Layer (EIL) and evaporation +. >Is used as a cathode. The device was then transferred back to the glove box and packaged with a glass lid to complete the device.
Comparative example 1-1: an organic electroluminescent device comprising only the hole blocking layer compound of the present invention as a hole blocking layer and simultaneously comprising an electron transport layer compound not falling within the specific range of the present invention co-deposited with the compound EI as an electron transport layer was produced by a method differing from that of example 1-1 only in the electron transport layer: the Electron Transport Layer (ETL) was formed by co-deposition of compound ET with compound EI, wherein the compound EI accounts for 60% of the total weight of the electron transport layer material, and the ETL has a thickness of
Comparative examples 1-2: an organic electroluminescent device comprising a hole blocking layer compound not falling within the specific range of the present invention as a hole blocking layer and simultaneously comprising an electron transporting layer compound of the present invention co-deposited with a compound EI as an electron transporting layer was produced, and the production method thereof was different from that of example 1-1 only in that the hole blocking layer: using compound HB as a Hole Blocking Layer (HBL) with a thickness of
Comparative examples 1-3: an organic electroluminescent device comprising a hole blocking layer compound not falling within the specific range of the present invention as a hole blocking layer and an electron transporting layer compound not falling within the specific range of the present invention co-deposited with the compound EI as an electron transporting layer was manufactured, and the manufacturing method thereof was different from that of example 1-1 only in that the hole blocking layer and the electron transporting layer: using compound HB as a Hole Blocking Layer (HBL) with a thickness of Use of a compound ET co-deposited with a compound EI as an Electron Transport Layer (ETL), wherein the compound EI occupies the electron transport layer60% of the total weight of the material, ETL thickness is +.>
The partial material structure used in the device is as follows:
the detailed partial device layer structure and the device data of examples and comparative examples are shown in table 1. The layers of more than one of the materials used are obtained by doping different compounds in the weight proportions indicated.
TABLE 1
Table 1 shows electroluminescent devices comprising different hole blocking layers in combination with electron transport layers at a current density of 10mA/cm 2 Is a test result of (a).
From the color coordinates and half-width data of examples 1-1 and comparative examples 1-1 to comparative examples 1-3, it is understood that the use of the hole blocking layer compound of the present invention and the electron transport layer compound of the present invention has little influence on the color change of the device.
As is clear from the comparison results of example 1-1 and comparative example 1-3, the voltage of example 1-1 was substantially equivalent, and the external quantum efficiency was reduced by 1.1%, but the device lifetime LT95 was greatly increased from 292 hours of comparative example 1-3 to 663 hours of example 1-1, and the lifetime was increased by 127%.
As is clear from the comparison results of example 1-1 and comparative example 1-2, the voltage of example 1-1 was slightly higher, the external quantum efficiency was reduced by 1.3%, but the device lifetime LT95 was greatly increased from 429 hours of comparative example 1-2 to 663 hours of example 1-1, and the lifetime was increased by 55%.
As is clear from the comparison results of example 1-1 and comparative example 1-1, the voltage of example 1-1 was substantially equivalent, and the external quantum efficiency was slightly reduced by 0.2%, but the device lifetime LT95 was greatly increased from 600 hours of comparative example 1-1 to 663 hours of example 1-1, and the lifetime was increased by 11%.
Therefore, when the hole blocking layer compound of the present invention and the electron transport layer compound of the present invention are used in combination, the device lifetime is significantly improved although the external quantum efficiency of the device is slightly reduced, which prominently shows the advantage of improving the device lifetime when the hole blocking layer compound of the structure of the present invention of formula 1 and the electron transport layer compound of the structure of the present invention of formula 2 are used in combination, compared to the case where the two compounds are used alone, and the case where the hole blocking layer compound and the electron transport layer compound are used in combination, which are conventional in the art. The device structure using the hole blocking layer compound of the present invention and the electron transport layer compound of the present invention in combination is very advantageous for OLED devices where a long lifetime is desired.
In summary, the organic electroluminescent device disclosed in the present invention comprises a hole blocking layer of the compound of formula 1 and an electron transport layer of formula 2. The specific compound combination can greatly improve the service life of the device, better compromise voltage and efficiency, obtain obviously improved comprehensive performance of the device, and has more advantages in the field of commercial application.
It should be understood that the various embodiments described herein are by way of example only and are not intended to limit the scope of the invention. Thus, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific and preferred embodiments described herein. Many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the invention. It is to be understood that the various theories as to why the present invention works are not intended to be limiting.
Claims (27)
1. An organic electroluminescent device comprising:
an anode is provided with a cathode,
a cathode electrode, which is arranged on the surface of the cathode,
and an organic layer disposed between the anode and the cathode, the organic layer comprising at least a first organic layer and a second organic layer;
wherein the organic layer comprises a compound having a structure represented by formula 1:
in the formula 1, the components are mixed,
wherein X is independently selected from NR ', CR ' R ', O, S or Se;
wherein R ', R "and R'" are each independently 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 arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amine having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid groups, ester groups, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof;
When X is selected from CR < lambda > R ' R ' and R ' can optionally be linked to form a ring;
wherein X is a1 To X a8 Each independently selected from CR 1 Or N; wherein X is a1 -X a8 At least one of them is CR 1 And R is 1 Is a structure represented by formula 1A:
in formula 1A, the CR is represented by 1 R is described in the structure 1 A position connected to C;
wherein L' is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;
wherein Ar is 1 And Ar is a group 2 Each independently selected from the group consisting of: substituted or unsubstituted aryl groups having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having from 3 to 30 carbon atoms, and combinations thereof;
wherein X is a1 -X a8 The remainder of R present in 1 Each independently 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 arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amine having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid groups, ester groups, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Two adjacent substituents R 1 Can optionally be linked to form a ring;
wherein the second organic layer comprises a compound having a structure represented by formula 2:
in the formula 2, the components are mixed,
wherein n is selected from 1,2,3 or 4; when n is 2 or more, each group L and B may be the same or different;
wherein L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;
wherein B is a substituted or unsubstituted electron-deficient heteroaryl group having 2 to 60 carbon atoms;
wherein a has a structure represented by formula 2A:
in the formula (2A),
wherein ring D and ring E each independently represent a substituted or unsubstituted aryl group having 5 to 50 ring atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms;
wherein at least one of ring D and ring E is a fused ring system;
wherein R is 2 And R is 2A Each independently 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 arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, Sulfinyl, sulfonyl, phosphino, and combinations thereof;
R 2 and R is 2A Can optionally be linked to form a ring.
2. The device of claim 1, wherein the organic layer disposed between the anode and the cathode further comprises at least one light emitting layer.
3. The device of claim 2, the light emitting layer comprising at least one host material and at least one dopant material.
4. The device of claim 3, wherein the organic layer is farther from the anode than the light-emitting layer, and the second organic layer is farther from the anode than the first organic layer.
5. The device of claim 1, wherein the device has an emission wavelength between 300nm and 1200 nm.
6. The device of claim 1, wherein the thickness of the first organic layer is between 0.1nm and 40nm, and/or the thickness of the second organic layer is between 0.1nm and 50 nm.
7. The device of claim 1, wherein the second organic layer further comprises at least another material.
8. The device of claim 7, wherein the other material is a metal complex, and the metal complex comprises a metal represented by formula L q Represented ligand L q ：
L (L) q In (1), Y 1 ，Y 2 ，Y 3 ，Y 4 ，Y 5 And Y 6 Each independently selected from CR Y Or N; wherein each R is Y Each of which is a single pieceIndependently selected from the group consisting of hydrogen, deuterium, alkyl, alkoxy, amino, silyl, cyano, halogen, aryl, and heteroaryl;
Wherein Z is selected from N, O, S or Se.
9. The device of claim 8, wherein the metal complex is 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.
10. The device of claim 1, wherein R ', R ", and R'" in formula 1 are each independently selected from substituted or unsubstituted aryl groups having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms.
11. The device of claim 10, wherein R ', R ", and R'" in formula 1 are each independently selected from the group consisting of: biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, dibenzofuranyl.
12. The device of claim 1, X in formula 1 a1 -X a8 The remainder of R present in 1 Each independently selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms.
13. The device of claim 12, X in formula 1 a1 -X a8 The remainder of R present in 1 Each independently selected from the group consisting of: hydrogen, deuterium, phenyl, biphenyl and terphenyl.
14. The device of claim 1, X in formula 1 a7 Is CR (CR) 1 And said R is 1 Is a structure represented by formula 1A.
15. The device of claim 1 or 14, ar in formula 1 1 And Ar is a group 2 Each independently selected from phenyl, biphenyl or terphenyl.
16. The device of claim 15, ar in formula 1 1 And Ar is a group 2 At least one of which is biphenyl or terphenyl.
17. The device of claim 1, wherein the compound of the structure of formula 1 is selected from the group consisting of:
18. the device as recited in claim 17, wherein hydrogen in all specific compounds from compounds 1-1-1 through compounds 20-10-4 can be partially or fully substituted with deuterium.
19. The device of claim 1, at least one of ring D and ring E in formula 2A is a fused ring system, and the fused ring system is at least two aryl and/or heteroaryl rings fused together to form a fused ring system comprising at least 10 carbon atoms, or a fused ring system comprising at least 10 total of both carbon and nitrogen atoms;
alternatively, at least one of ring D and ring E in formula 2A is a fused ring system, and the fused ring system is at least three aryl and/or heteroaryl rings fused together to form a fused ring system comprising at least 14 carbon atoms, or a fused ring system comprising at least 14 total of both carbon and nitrogen atoms.
20. The device of claim 1, a in formula 2 being selected from the group consisting of formulas 3 to 33:
wherein T is 1 To T 22 Each independently selected from CR T C, or N;
wherein each R is T Each independently 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 atomsA group, a substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, a substituted or unsubstituted aralkyl having 7-30 carbon atoms, a substituted or unsubstituted alkoxy having 1-20 carbon atoms, a substituted or unsubstituted aryloxy having 6-30 carbon atoms, a substituted or unsubstituted alkenyl having 2-20 carbon atoms, a substituted or unsubstituted aryl having 6-30 carbon atoms, a substituted or unsubstituted heteroaryl having 3-30 carbon atoms, a substituted or unsubstituted silyl having 3-20 carbon atoms, a substituted or unsubstituted arylsilane having 6-20 carbon atoms, a substituted or unsubstituted amine group having 0-20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile, a thio group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
In formulas 3 to 33, adjacent substituents can optionally be linked to form a ring.
21. The device of claim 20, wherein a in formula 2 is independently selected from the group consisting of a 1 -A 298 And (3) a group consisting of:
22. the device of claim 1, wherein L in formula 2 is selected from the group consisting of a single bond and formulas 34 to 58:
wherein R is 3 ,R 4 ,R 5 And R is 6 Each independently represents mono-substituted, poly-substituted or unsubstituted; when they represent multiple substitutions, adjacent substitutions can optionally be joined to form a ring;
wherein R is 3 ,R 4 ,R 5 And R is 6 Each independently 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 cycloalkyl havingAn 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 nitrile, an isonitrile, a thio group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.
23. The device of claim 21, wherein each L in formula 2 is independently selected from the group consisting of a single bond L 0 L is as follows 1 To L 58 And (3) a group consisting of:
24. the device of claim 1, B in formula 2 being selected from the group consisting of formulas 59 to 63:
wherein X is 1 To X 6 Each independently selected from CR x C, O, S, N or NR x ’，
Wherein X is 1 To X i At least one of which is N, or wherein X 1 To X i At least two of which are N, or X 1 To X i At least three of which are N; the X is i Corresponds to the X 1 To X 6 The largest sequence number exists in formulas 59 to 63;
wherein R is 7 Each independently represents mono-substituted, poly-substituted or unsubstituted; when they represent multiple substitutions, adjacent substitutions can optionally be joined to form a ring;
wherein R is 7 ,R x, And R is x ' each independently 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 arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amine having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid groups, ester groups, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof.
25. The device of claim 23, wherein B in formula 2 is each independently selected from the group consisting of B1 to B105:
26. the device of claim 25, wherein said compound of the structure of formula 2, wherein said a is selected from the group consisting of a 1 -A 298 The B's are each independently selected from the group consisting of B 1 -B 105 The L is each independently selected from the group consisting of L 0 -L 58 A group of groups.
27. A display assembly comprising the organic electroluminescent device of any one of claims 1-26.
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| CN109836435A (en) * | 2017-11-27 | 2019-06-04 | 北京夏禾科技有限公司 | Triarylamine compounds containing thiophene |
| CN109912619A (en) * | 2017-12-13 | 2019-06-21 | 北京夏禾科技有限公司 | Electroluminescent organic material and device |
| CN109928885A (en) * | 2017-12-19 | 2019-06-25 | 北京夏禾科技有限公司 | Neighbours Asia benzene triarylamine compounds |
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| CN101128559A (en) * | 2004-12-17 | 2008-02-20 | 伊斯曼柯达公司 | Phosphorescent OLEDs with exciton blocking layer |
| CN104904032A (en) * | 2012-11-06 | 2015-09-09 | 巴斯夫欧洲公司 | Phenoxasiline compounds for electronic applications |
| CN109836435A (en) * | 2017-11-27 | 2019-06-04 | 北京夏禾科技有限公司 | Triarylamine compounds containing thiophene |
| CN109912619A (en) * | 2017-12-13 | 2019-06-21 | 北京夏禾科技有限公司 | Electroluminescent organic material and device |
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