CN115710290A - Organic electroluminescent material and device thereof - Google Patents
Organic electroluminescent material and device thereof Download PDFInfo
- Publication number
- CN115710290A CN115710290A CN202210747647.5A CN202210747647A CN115710290A CN 115710290 A CN115710290 A CN 115710290A CN 202210747647 A CN202210747647 A CN 202210747647A CN 115710290 A CN115710290 A CN 115710290A
- Authority
- CN
- China
- Prior art keywords
- group
- carbon atoms
- substituted
- unsubstituted
- ring
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000463 material Substances 0.000 title abstract description 59
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- 229910052751 metal Inorganic materials 0.000 claims abstract description 53
- 239000002184 metal Substances 0.000 claims abstract description 53
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 455
- 150000004696 coordination complex Chemical class 0.000 claims description 170
- -1 phosphino group Chemical group 0.000 claims description 154
- 239000010410 layer Substances 0.000 claims description 109
- 125000001424 substituent group Chemical group 0.000 claims description 104
- 125000003118 aryl group Chemical group 0.000 claims description 61
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 59
- 229910052805 deuterium Inorganic materials 0.000 claims description 59
- 125000006413 ring segment Chemical group 0.000 claims description 58
- 125000001072 heteroaryl group Chemical group 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 52
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 49
- 229910052757 nitrogen Inorganic materials 0.000 claims description 48
- 239000003446 ligand Substances 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 39
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 36
- 125000000623 heterocyclic group Chemical group 0.000 claims description 35
- 150000002431 hydrogen Chemical class 0.000 claims description 34
- 229910052799 carbon Inorganic materials 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 33
- 229910052717 sulfur Inorganic materials 0.000 claims description 32
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 27
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 26
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 26
- 238000006467 substitution reaction Methods 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000004104 aryloxy group Chemical group 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000005104 aryl silyl group Chemical group 0.000 claims description 20
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 239000011737 fluorine Substances 0.000 claims description 18
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000000732 arylene group Chemical group 0.000 claims description 15
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 15
- 125000005549 heteroarylene group Chemical group 0.000 claims description 15
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 13
- 125000004185 ester group Chemical group 0.000 claims description 13
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 13
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 12
- 229910052796 boron Inorganic materials 0.000 claims description 12
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 12
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 239000012044 organic layer Substances 0.000 claims description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims description 11
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 11
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- 229910005965 SO 2 Inorganic materials 0.000 claims description 10
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 7
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 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
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 claims description 4
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 claims description 4
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims description 4
- 229960005544 indolocarbazole Drugs 0.000 claims description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000005580 triphenylene group Chemical group 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 150000002739 metals Chemical group 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 3
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 3
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- HCAUQPZEWLULFJ-UHFFFAOYSA-N benzo[f]quinoline Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=N1 HCAUQPZEWLULFJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003636 chemical group Chemical group 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- UTUZBCDXWYMYGA-UHFFFAOYSA-N silafluorene Chemical compound C12=CC=CC=C2CC2=C1C=CC=[Si]2 UTUZBCDXWYMYGA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 229910052737 gold Inorganic materials 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- WLKSSWJSFRCZKL-UHFFFAOYSA-N trimethylgermanium Chemical group C[Ge](C)C WLKSSWJSFRCZKL-UHFFFAOYSA-N 0.000 claims 1
- 230000006872 improvement Effects 0.000 abstract description 10
- 230000009467 reduction Effects 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- 238000006243 chemical reaction Methods 0.000 description 51
- 230000000052 comparative effect Effects 0.000 description 46
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- 230000002829 reductive effect Effects 0.000 description 31
- 230000015572 biosynthetic process Effects 0.000 description 28
- 238000003786 synthesis reaction Methods 0.000 description 28
- 239000000243 solution Substances 0.000 description 25
- 238000004440 column chromatography Methods 0.000 description 22
- 239000003208 petroleum Substances 0.000 description 22
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 20
- 229940093475 2-ethoxyethanol Drugs 0.000 description 20
- 239000012046 mixed solvent Substances 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 11
- 230000003111 delayed effect Effects 0.000 description 11
- 239000000758 substrate Substances 0.000 description 10
- 239000007924 injection Substances 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 7
- 230000036961 partial effect Effects 0.000 description 7
- 150000003384 small molecules Chemical class 0.000 description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000005538 encapsulation Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 230000000670 limiting effect Effects 0.000 description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 229910052732 germanium Inorganic materials 0.000 description 3
- 239000002346 layers by function Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 125000004437 phosphorous atom Chemical group 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 125000003003 spiro group Chemical group 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 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 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 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
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
- 229920001621 AMOLED Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-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
- 125000002723 alicyclic group Chemical group 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 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 group 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000003800 germyl group Chemical class [H][Ge]([H])([H])[*] 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000006504 o-cyanobenzyl group Chemical group [H]C1=C([H])C(C#N)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000013086 organic photovoltaic Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 230000002441 reversible effect Effects 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
- 239000010703 silicon Chemical group 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- HWIATMHDQVGMFQ-UHFFFAOYSA-N 1,3-azaborinine Chemical compound B1=CC=CN=C1 HWIATMHDQVGMFQ-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
- OBUDOIAYABJUHQ-UHFFFAOYSA-N 1,4-azaborinine Chemical compound B1=CC=NC=C1 OBUDOIAYABJUHQ-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
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical compound C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-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
- FBTOLQFRGURPJH-UHFFFAOYSA-N 1-phenyl-9h-carbazole Chemical group C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 FBTOLQFRGURPJH-UHFFFAOYSA-N 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
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 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
- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 description 1
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical class C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 1
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 description 1
- 125000006482 3-iodobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(I)=C1[H])C([H])([H])* 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical group C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 1
- 125000006483 4-iodobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1I)C([H])([H])* 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- XFVCIUGEAOQLBW-UHFFFAOYSA-N 7-selenabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2[Se]C2=C1 XFVCIUGEAOQLBW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ASDMIVKXUPKEQA-UHFFFAOYSA-N C1(=CC=CC=C1)C(C[Ge])C1=CC=CC=C1 Chemical group C1(=CC=CC=C1)C(C[Ge])C1=CC=CC=C1 ASDMIVKXUPKEQA-UHFFFAOYSA-N 0.000 description 1
- YMXBTVMTFUVNSZ-UHFFFAOYSA-N CC(C)(C)[Ge](c1ccccc1)c1ccccc1 Chemical group CC(C)(C)[Ge](c1ccccc1)c1ccccc1 YMXBTVMTFUVNSZ-UHFFFAOYSA-N 0.000 description 1
- SMCGOEXATRUDNQ-UHFFFAOYSA-N CC(C)C[Ge](C1=CC=CC=C1)C1=CC=CC=C1 Chemical group CC(C)C[Ge](C1=CC=CC=C1)C1=CC=CC=C1 SMCGOEXATRUDNQ-UHFFFAOYSA-N 0.000 description 1
- TXDQUYVYDVCKGS-UHFFFAOYSA-N CC(C)[Ge](C(C)C)C1=CC=CC=C1 Chemical group CC(C)[Ge](C(C)C)C1=CC=CC=C1 TXDQUYVYDVCKGS-UHFFFAOYSA-N 0.000 description 1
- FPEQOYNVLZOSNS-UHFFFAOYSA-N CC[Ge](CC)C1=CC=CC=C1 Chemical group CC[Ge](CC)C1=CC=CC=C1 FPEQOYNVLZOSNS-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- FBVBNCGJVKIEHH-UHFFFAOYSA-N [1]benzofuro[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3OC2=C1 FBVBNCGJVKIEHH-UHFFFAOYSA-N 0.000 description 1
- XFBBQEOMCCAUNY-UHFFFAOYSA-N [Ge]C(c1ccccc1)c1ccccc1 Chemical group [Ge]C(c1ccccc1)c1ccccc1 XFBBQEOMCCAUNY-UHFFFAOYSA-N 0.000 description 1
- CVVOWTWCWHITLU-UHFFFAOYSA-N [Ge]CCCC(C1=CC=CC=C1)C1=CC=CC=C1 Chemical group [Ge]CCCC(C1=CC=CC=C1)C1=CC=CC=C1 CVVOWTWCWHITLU-UHFFFAOYSA-N 0.000 description 1
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- KCQLSIKUOYWBAO-UHFFFAOYSA-N azaborinine Chemical compound B1=NC=CC=C1 KCQLSIKUOYWBAO-UHFFFAOYSA-N 0.000 description 1
- 125000002785 azepinyl group Chemical group 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002188 cycloheptatrienyl group Chemical group C1(=CC=CC=CC1)* 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- LUGNZBKOLRFNPT-UHFFFAOYSA-N dimethyl(phenyl)germanium Chemical group C[Ge](C)C1=CC=CC=C1 LUGNZBKOLRFNPT-UHFFFAOYSA-N 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- YVCGDHWZULOHFR-UHFFFAOYSA-N diphenyl(propan-2-yl)germanium Chemical group C=1C=CC=CC=1[Ge](C(C)C)C1=CC=CC=C1 YVCGDHWZULOHFR-UHFFFAOYSA-N 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- AZHVQJLDOFKHPZ-UHFFFAOYSA-N oxathiazine Chemical compound O1SN=CC=C1 AZHVQJLDOFKHPZ-UHFFFAOYSA-N 0.000 description 1
- CQDAMYNQINDRQC-UHFFFAOYSA-N oxatriazole Chemical compound C1=NN=NO1 CQDAMYNQINDRQC-UHFFFAOYSA-N 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000003585 oxepinyl group Chemical group 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical compound C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000011574 phosphorus Chemical group 0.000 description 1
- 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
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 239000011669 selenium Chemical group 0.000 description 1
- 125000003748 selenium group Chemical group *[Se]* 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003554 tetrahydropyrrolyl group Chemical group 0.000 description 1
- 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
- 238000002207 thermal evaporation Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000003777 thiepinyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- SLAJUCLVZORTHN-UHFFFAOYSA-N triphenylgermanium Chemical group C1=CC=CC=C1[Ge](C=1C=CC=CC=1)C1=CC=CC=C1 SLAJUCLVZORTHN-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000010200 validation analysis Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Images
Classifications
-
- 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
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
Organic electroluminescent materials and devices thereof are disclosed. The organic electroluminescent material is L containing a structure of formula 1 a The novel compounds are applied to electroluminescent devices, so that excellent device performance can be obtained, such as reduction of device voltage, improvement of current efficiency, power efficiency and external quantum efficiency, comprehensive improvement of device performance in all aspects can be achieved, and finally, the comprehensive performance of the device is greatly improved. Also disclosed are organic electroluminescent devices comprising the metal complexes and compositions comprising the metal complexes.
Description
Technical Field
The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. More particularly, it relates to an L comprising the structure of formula 1 a A metal complex of a ligand, and an organic electroluminescent device comprising the metal complex and a composition comprising the metal complex.
Background
Organic electronic devices include, but are not limited to, the following classes: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), organic Light Emitting Transistors (OLETs), organic Photovoltaics (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light emitting devices.
In 1987, tang and Van Slyke, by Isman Kodak, reported a two-layer organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters,1987,51 (12): 913-915). Upon biasing the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). State-of-the-art OLEDs may include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between the cathode and anode. Since OLEDs are a self-emissive solid state device, it offers great potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications, such as in the fabrication of flexible substrates.
OLEDs can be classified into three different types according to their light emitting mechanism. The OLEDs of the invention by Tang and van Slyke are fluorescent OLEDs. It uses only singlet luminescence. The triplet states generated in the device are wasted through the non-radiative decay channel. Therefore, the Internal Quantum Efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hinders the commercialization of OLEDs. In 1997, forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complex-containing heavy metals as emitters. Thus, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributes to the commercialization of Active Matrix OLEDs (AMOLEDs). Recently, adachi achieved high efficiency through Thermally Activated Delayed Fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible to return excitons from the triplet state to the singlet state. In TADF devices, triplet excitons are able to generate singlet excitons through reverse intersystem crossing, resulting in high IQE.
OLEDs can also be classified into small molecule and polymer OLEDs depending on the form of the material used. Small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of small molecules can be large, as long as they have a precise structure. Dendrimers with well-defined structures are considered small molecules. The polymeric OLED comprises a conjugated polymer and a non-conjugated polymer having a pendant light-emitting group. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the fabrication process.
Various OLED fabrication methods exist. Small molecule OLEDs are typically fabricated by vacuum thermal evaporation. Polymer OLEDs are fabricated by solution processes such as spin coating, ink jet printing, and nozzle printing. Small molecule OLEDs can also be fabricated by solution methods if the materials can be dissolved or dispersed in a solvent.
The light emitting color of the OLED can be realized by the structural design of the light emitting material. An OLED may comprise one light emitting layer or a plurality of light emitting layers to achieve a desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have the problems of blue unsaturation, short device lifetime, high operating voltage, and the like. Commercial full-color OLED displays typically employ a hybrid strategy, using either blue fluorescence and phosphorescent yellow, or red and green. At present, the rapid decrease in efficiency of phosphorescent OLEDs at high luminance is still a problem. In addition, it is desirable to have a more saturated emission spectrum, higher efficiency and longer device lifetime.
US2013119354A1 discloses a metal complex having the following general structure:
wherein R is 1 -R 4 Selected from the group consisting of hydrogen, deuterium, alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof. In this application only R is disclosed 1 Metal complexes of aryl substituents that are phenyl groups and their use in devices, metal complexes having substituents as specified herein and their effect on device performance are not disclosed and taught.
CN107236006A discloses a red light metal complex with the following general structure:
metal complexes of arylamine substituted fluorene ligands and their use in devices are disclosed in this application. This application discloses the use of fluorenyl ligands with polyarylamine substitution in metal complexes. No metal complexes containing specific skeletal structure ligands with specific substituents as in the present application and their effect on device performance are disclosed and taught.
CN101108964A discloses a red light metal complex having the following general structure:
red light emitting metal complexes containing diketo ligands with carbazole substituents and their use in organic electroluminescent devices are disclosed in this application. This application discloses metal complexes having carbazole substituents on phenylquinolines and coordinated with diketone ligands. No metal complexes containing specific skeletal structure ligands with specific substituents as in the present application and their impact on device performance are disclosed and taught.
Disclosure of Invention
Hair brushIt is intended to provide a series of L's comprising the structure of formula 1 a Metal complexes of ligands to solve at least part of the above problems. The novel compounds can obtain excellent device performance when applied to electroluminescent devices, such as reduction of device voltage, improvement of current efficiency, power efficiency and external quantum efficiency, comprehensive improvement of device performance in all aspects, and finally great improvement of device comprehensive performance.
According to one embodiment of the present invention, a metal complex is disclosed that comprises a metal M, and a ligand L coordinated to the metal M a Wherein L is a Has a structure represented by formula 1:
in the case of the formula 1, the compound,
the metal M is selected from metals having a relative atomic mass greater than 40;
ring Cy is selected, identically or differently on each occurrence, from a substituted or unsubstituted aromatic ring having 6-24 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5-24 ring atoms, or a combination thereof; and the ring Cy comprises at least 3 carbon atoms;
cy is linked to the metal M through a metal-carbon or metal-nitrogen bond;
x is selected, identically or differently at each occurrence, from the group consisting of O, S, se, NR ', siR ' R ' and GeR ' R '; when two R 'are present at the same time, the two R's are the same or different;
X 1 -X 8 is selected, identically or differently on each occurrence, from C, CR x ，CR x1 Or N; x 1 -X 4 At least one of which is C and is connected to the ring Cy;
X 1 、X 2 、X 3 or X 4 Is linked to the metal M by a metal-carbon or metal-nitrogen bond;
X 1 -X 8 at least one of them is selected from CR x1 And R is x1 Has a structure shown in formula 2:
wherein, in the formula 2,
R A and R B The same or different at each occurrence denotes mono-, poly-or no-substitution;
ring a and ring B are selected, identically or differently, from carbocycles having 3-30 ring atoms, heterocycles having 3-30 ring atoms, or combinations thereof;
n is 0 or 1;
A 1 ，A 2 ，B 1 ，B 2 e, identically or differently at each occurrence, is selected from C, N, B, P, CR "', siR" ' or GeR "';
l is selected from single bond, O, S, SO 2 Se, NR ", CR" R ", siR" R ", geR" R ", BR", PR ", P (O) R", R "C = CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, an arylene group having 6-30 carbon atoms, a heteroarylene group having 3-30 carbon atoms, and combinations thereof;
R’，R”，R”’，R x ，R A ，R B each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring 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 alkynyl 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 alkylsilyl having 6 to 20 carbon atomsAn arylsilyl group of carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
"Tn" indicates the attachment position of said formula 2;
adjacent R', R x Optionally linked to form a ring;
adjacent R ', R', R A ，R B Can be optionally connected to form a ring.
According to another embodiment of the present invention, there is also disclosed an electroluminescent device, including: an anode, a cathode, and an organic layer disposed between the anode and the cathode, at least one of the organic layers comprising the metal complex of the above embodiments.
According to another embodiment of the present invention, a combination of compounds is also disclosed, comprising the metal complex of the above embodiment.
The invention discloses a series of L containing a structure of a formula 1 a The novel compounds are applied to electroluminescent devices, so that excellent device performance can be obtained, such as reduction of device voltage, improvement of current efficiency, power efficiency and external quantum efficiency, comprehensive improvement of device performance in all aspects can be achieved, and finally, the comprehensive performance of the device is greatly improved.
Drawings
FIG. 1 is a schematic representation of an organic light-emitting device that can contain the metal complexes disclosed herein and compositions comprising the metal complexes.
FIG. 2 is a schematic representation of another organic light emitting device that can contain the metal complexes disclosed herein and compositions comprising the metal complexes.
Detailed Description
OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically, but without limitation, illustrates an organic light emitting device 100. The figures are not necessarily to scale, and some of the layer structures in the figures may be omitted as desired. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, an emissive layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 may be fabricated by sequentially depositing the described layers. The nature and function of the various layers and exemplary materials are described in more detail in U.S. Pat. No. 7,279,704B2 at columns 6-10, which is incorporated herein by reference in its entirety.
There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F at a molar ratio of 50 4 -TCNQ m-MTDATA as disclosed in U.S. patent application publication No. 2003/0230980, incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. patent No. 6,303,238 to Thompson (Thompson) et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including a composite cathode having a thin layer of a metal such as Mg: ag with an overlying transparent, 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 a protective layer 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 via non-limiting embodiments. The function of the OLED may be achieved by combining the various layers described above, or some layers may be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of materials may be used to achieve optimal performance. Any functional layer may comprise several sub-layers. For example, the light emitting layer may have two layers of different light emitting materials to achieve a desired light emission spectrum.
In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.
The OLED also requires an encapsulation layer, as shown in fig. 2, which is an exemplary, non-limiting illustration of an organic light emitting device 200, which differs from fig. 1 in that an encapsulation layer 102 may also be included over the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function may be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film encapsulation is described in U.S. Pat. No. 7,968,146b2, the entire contents of which are incorporated herein by reference.
Devices manufactured according to embodiments of the present invention may be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, microdisplays, 3-D displays, vehicle displays, and taillights.
The materials and structures described herein may also be used in the other organic electronic devices listed previously.
As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. Where a first layer is described as being "disposed on" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that a first layer is "in contact with" a second layer, there may be other layers 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 "photoactive" when it is believed that the ligand directly contributes to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive properties of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.
It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by delaying fluorescence beyond 25% spin statistics. Delayed fluorescence can generally be divided into two types, i.e., P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence results from triplet-triplet annihilation (TTA).
On the other hand, E-type delayed fluorescence does not depend on collision of two triplet states, but on conversion between a triplet state and a singlet excited state. Compounds capable of producing E-type delayed fluorescence need to have a very small singlet-triplet gap in order to switch between energy states. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as Thermally Activated Delayed Fluorescence (TADF). A significant feature of TADF is that the retardation component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize non-radiative decay from the triplet state, then the fraction of backfill singlet excited states may reach 75%. The total singlet fraction may be 100%, far exceeding 25% of the spin statistics of the electrogenerated excitons.
The delayed fluorescence characteristic of type E can be found in excited complex systems or in single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the light emitting material to have a small mono-triplet energy gap (Δ Ε) S-T ). Organic non-metal containing donor-acceptor emissive materials may be able to achieve this. The emission of these materials is generally characterized as donor-acceptor Charge Transfer (CT) type emission. These donor-acceptor typesSpatial separation of HOMO from LUMO in a compound typically results in a small Δ E S-T . These states may include CT states. Generally, donor-acceptor light emitting materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) to an electron acceptor moiety (e.g., a six-membered, N-containing, aromatic ring).
Definitions for substituent terms
Halogen or halide-as used herein, includes fluorine, chlorine, bromine and iodine.
Alkyl-as used herein, includes both straight and branched chain alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms. 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. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, the alkyl group may be optionally substituted.
Cycloalkyl-as used herein, includes cyclic alkyl. The cycloalkyl group may be a cycloalkyl group having 3 to 20 ring carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4-dimethylcyclohexyl are preferred. In addition, cycloalkyl groups may be optionally substituted.
Heteroalkyl-as used herein, heteroalkyl comprises a alkyl chain wherein one or more carbons are substituted with a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium and boron atoms. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxyethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, trimethylgermylisopropyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, tert-butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl. In addition, heteroalkyl groups may be optionally substituted.
Alkenyl-as used herein, encompasses straight chain, branched chain, and cyclic olefin groups. The alkenyl group may be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of the alkenyl group include a vinyl group, a propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a1, 3-butadienyl group, a 1-methylvinyl group, a styryl group, a 2, 2-diphenylvinyl group, a 1-methylallyl group, a1, 1-dimethylallyl group, a 2-phenylallyl group, a 3, 3-diphenylallyl group, a1, 2-dimethylallyl group, a 1-phenyl-1-butenyl group, a 3-phenyl-1-butenyl group, a cyclopentenyl group, a cyclopentadienyl group, a cyclohexenyl group, a cycloheptenyl group, a cycloheptatrienyl group, a cyclooctenyl group, a cyclooctatetraenyl group and a norbornenyl group. In addition, alkenyl groups may be optionally substituted.
Alkynyl-as used herein, straight chain alkynyl groups are contemplated. The alkynyl group may be an alkynyl group containing 2 to 20 carbon atoms, preferably an alkynyl group having 2 to 10 carbon atoms. Examples of alkynyl include ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, and the like. Among the above, preferred are ethynyl, propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl and phenylethynyl. In addition, alkynyl groups may be optionally substituted.
Aryl or aromatic-as used herein, non-fused and fused systems are contemplated. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene,
perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p- (2-phenylpropyl) phenyl, 4 '-methyldiphenyl, 4' -t-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesitylphenyl and m-tetrabiphenyl. In addition, the aryl group may be optionally substituted.
Heterocyclyl or heterocyclic-as used herein, non-aromatic cyclic groups are contemplated. The non-aromatic heterocyclic group includes a saturated heterocyclic group having 3 to 20 ring atoms, at least one of which is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom and a boron atom, and an unsaturated non-aromatic heterocyclic group having 3 to 20 ring atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, which include at least one hetero atom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuryl, tetrahydropyranyl, dioxolanyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiepinyl, azepinyl, and tetrahydrosilolyl. In addition, the heterocyclic group may be optionally substituted.
Heteroaryl-as used herein, non-fused and fused heteroaromatic groups that may contain 1 to 5 heteroatoms, at least one of which is selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, a phosphorus atom, a germanium atom and a boron atom. Heteroaryl also refers to heteroaryl. The heteroaryl group may be a heteroaryl group having 3 to 30 carbon atoms, preferably a heteroaryl group having 3 to 20 carbon atoms, more preferably a heteroaryl group having 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, oxatriazole, bisoxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, quinoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuropyridine, furobipyridine, benzothienopyridine, thienobipyridine, benzothienobipyridine, cinnoline, selenobenzene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-azaborine, 1, 3-azaborine, 1, 4-azaborine, azaborizole and analogs thereof. In addition, heteroaryl groups may be optionally substituted.
Alkoxy-as used herein, is represented by-O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or-O-heterocyclyl. Examples and preferred examples of the alkyl group, cycloalkyl group, heteroalkyl group and heterocyclic group are the same as those described above. The alkoxy group may be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of the alkoxy group include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuryloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, alkoxy groups may be optionally substituted.
Aryloxy-as used herein, is represented by-O-aryl or-O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group may be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of the aryloxy group include a phenoxy group and a biphenyloxy group. In addition, the aryloxy group may be optionally substituted.
Aralkyl-as used herein, encompasses aryl-substituted alkyl groups. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of the aralkyl group include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl tert-butyl group, an α -naphthylmethyl group, a 1- α -naphthyl-ethyl group, a 2- α -naphthylethyl group, a 1- α -naphthylisopropyl group, a 2- α -naphthylisopropyl group, a β -naphthylmethyl group, a 1- β -naphthylethyl group, a 2- β -naphthylethyl group, a 1- β -naphthylisopropyl group, a 2- β -naphthylisopropyl group, a p-methylbenzyl group, a m-methylbenzyl group, an o-methylbenzyl group, a p-chlorobenzyl group, a m-chlorobenzyl group, a p-chlorobenzyl group, a m-bromobenzyl group, an o-bromobenzyl group, a p-iodobenzyl group, a m-iodobenzyl group, a p-hydroxybenzyl group, a m-hydroxybenzyl group, an o-hydroxybenzyl group, a p-aminobenzyl group, an m-aminobenzyl group, a p-nitrobenzyl group, a m-nitrobenzyl group, an o-cyanobenzyl group, a 1-hydroxy-2-phenylisopropyl group and a 1-chloro-2-isopropylyl group. Among the above, preferred are benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl. In addition, the aralkyl group may be optionally substituted.
Alkylsilyl-as used herein, alkyl substituted silyl is contemplated. The alkylsilyl group may be an alkylsilyl group of 3-20 carbon atoms, preferably an alkylsilyl group of 3-10 carbon atoms. Examples of the alkylsilyl group include trimethylsilyl group, triethylsilyl group, methyldiethylsilyl group, ethyldimethylsilyl group, tripropylsilyl group, tributylsilyl group, triisopropylsilyl group, methyldiisopropylsilyl group, dimethylisopropylsilyl group, tri-tert-butylsilyl group, triisobutylsilyl group, dimethyl-tert-butylsilyl group, and methyl-di-tert-butylsilyl group. Additionally, the alkylsilyl group may be optionally substituted.
Arylsilyl-as used herein, encompasses at least one aryl-substituted silicon group. The arylsilane group may be an arylsilane group having 6 to 30 carbon atoms, preferably an arylsilane group having 8 to 20 carbon atoms. Examples of the arylsilyl group include triphenylsilyl group, phenylbiphenylsilyl group, diphenylbiphenylsilyl group, phenyldiethylsilyl group, diphenylethylsilyl group, phenyldimethylsilyl group, diphenylmethylsilyl group, phenyldiisopropylsilyl group, diphenylisopropylsilyl group, diphenylbutylsilyl group, diphenylisobutylsilyl group, and diphenyltert-butylsilyl group. In addition, the arylsilyl group may be optionally substituted.
Alkylgermyl-as used herein, alkyl-substituted germyl is contemplated. The alkylgermyl group may be an alkylgermyl group having 3 to 20 carbon atoms, preferably an alkylgermyl group having 3 to 10 carbon atoms. Examples of the alkylgermyl group include a trimethylgermyl group, a triethylgermyl group, a methyldiethylgermyl group, an ethyldimethylgermyl group, a tripropylgermyl group, a tributylgermyl group, a triisopropylgermyl group, a methyldiisopropylgermyl group, a dimethylisopropylgermyl group, a tri-tert-butylgermyl group, a triisobutylgermyl group, a dimethyl-tert-butylgermyl group, and a methyl-di-tert-butylgermyl group. In addition, the alkylgermyl group may be optionally substituted.
Arylgermyl-as used herein, encompasses at least one aryl or heteroaryl substituted germyl. The arylgermanium group may be an arylgermanium group having 6 to 30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of the arylgermanium group include a triphenylgermanium group, a phenylbiphenylgermanium group, a diphenylbiphenylgermanium group, a phenyldiethylgermanium group, a diphenylethylgermanium group, a phenyldimethylgermanium group, a diphenylmethylgermanium group, a phenyldiisopropylgermanium group, a diphenylisopropylgermanium group, a diphenylbutylgermanium group, a diphenylisobutylgermanium group, a diphenylt-butylgermanium group. In addition, the arylgermyl group may be optionally substituted.
The term "aza" in aza-dibenzofuran, aza-dibenzothiophene, etc., means that one or at least two C-H groups in the corresponding aromatic moiety are replaced by a nitrogen atom. For example, azatriphenylenes include dibenzo [ f, h ] quinoxalines, dibenzo [ f, h ] quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the aza derivatives described above will be readily apparent to one of ordinary skill in the art, and all such analogs are intended to be encompassed by the term as described herein.
In this disclosure, unless otherwise defined, when any one of the terms in the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermyl, substituted arylgermyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, meaning alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermyl, arylgermyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl, and phosphino groups, any of which may be substituted with one or more substituents selected from deuterium, halogen, unsubstituted alkyl having from 1 to 20 carbon atoms, unsubstituted cycloalkyl having from 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having from 1 to 20 carbon atoms, unsubstituted heteroaryl having from 3 to 20 carbon atoms, unsubstituted aryl having from 1 to 20 carbon atoms, unsubstituted aryl having from 2 to 6 carbon atoms, unsubstituted aryl having from 3 to 20 carbon atoms, unsubstituted aryl having from 2 to 6 carbon atoms, unsubstituted alkylgermyl groups having 3 to 20 carbon atoms, unsubstituted arylgermyl groups having 6 to 20 carbon atoms, unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
It will be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name may be written depending on whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or depending on whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or linking fragments are considered to be equivalent.
In the compounds mentioned in the present disclosure, a hydrogen atom may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. Substitution of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.
In the compounds mentioned in the present disclosure, multiple substitutions are meant to include within the scope of double substitutions up to the maximum available substitutions. When a substituent in a compound mentioned in the present disclosure represents multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), that is, it means that the substituent may exist at a plurality of available substitution positions on its connecting structure, and the substituent existing at each of the plurality of available substitution positions may be the same structure or different structures.
In the compounds mentioned in the present disclosure, adjacent substituents in the compound cannot be linked to form a ring unless specifically defined, for example, adjacent substituents can be optionally linked to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can optionally be linked to form a ring, both in the case where adjacent substituents may be linked to form a ring and in the case where adjacent substituents are not linked to form a ring. When adjacent substituents can optionally be joined to form a ring, the ring formed can be monocyclic or polycyclic (including spiro, bridged, fused, etc.), as well as alicyclic, heteroalicyclic, aromatic, or heteroaromatic rings. In this expression, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom as well as substituents bonded to carbon atoms directly bonded to each other.
The expression that adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
the expression that adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
the expression that adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to further away carbon atoms are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
further, the expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that, in the case where one of the adjacent two substituents 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 equation:
according to one embodiment of the present invention, a metal complex is disclosed comprising a metal M, and a ligand L coordinated to the metal M a Wherein L is a Has a structure represented by formula 1:
in the formula 1, the first and second groups,
the metal M is selected from metals having a relative atomic mass greater than 40;
ring Cy, identically or differently on each occurrence, is selected from a substituted or unsubstituted aromatic ring having 6 to 24 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5 to 24 ring atoms, or a combination thereof; and the ring Cy comprises at least 3 carbon atoms;
cy is linked to the metal M through a metal-carbon bond or a metal-nitrogen bond;
x is selected, identically or differently at each occurrence, from the group consisting of O, S, se, NR ', siR ' R ' and GeR ' R '; when two R 'are present at the same time, the two R's are the same or different;
X 1 -X 8 selected, identically or differently at each occurrence, from C, CR x ，CR x1 Or N; x 1 -X 4 At least one of which is C and is connected to the ring Cy;
X 1 、X 2 、X 3 or X 4 Is linked to the metal M by a metal-carbon or metal-nitrogen bond;
when X is 1 、X 2 、X 3 Or X 4 When linked to said metal M by a metal-carbon bond, X 1 、X 2 、X 3 Or X 4 Is selected from C;
X 1 -X 8 at least one of them is selected from CR x1 And R is x1 Has a structure shown in formula 2:
wherein, in the formula 2,
R A and R B The same or different at each occurrence indicates mono-, poly-or no-substitution;
ring a and ring B are selected, identically or differently, from carbocycles having 3-30 ring atoms, heterocycles having 3-30 ring atoms, or combinations thereof;
n is 0 or 1;
A 1 ，A 2 ，B 1 ，B 2 e, identically or differently at each occurrence, is selected from C, N, B, P, CR "', siR" ' or GeR "';
l is selected from single bond, O, S, SO 2 Se, NR ", CR" R ", siR" R ", geR" R ", BR", PR ", P (O) R", R "C = CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, an arylene group having 6-30 carbon atoms, a heteroarylene group having 3-30 carbon atoms, and combinations thereof;
R’，R”，R”’，R x ，R A ，R B each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl 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 alkylgermyl group having 3 to 20 carbon atoms,substituted or unsubstituted arylgermanyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
"" indicates the attachment position of said formula 2;
adjacent R', R x Can be optionally connected to form a ring;
adjacent R ', R', R A ，R B Can optionally be connected to form a ring.
As used herein, "R', R x Can optionally be linked to form a ring ", is intended to denote a group in which adjacent substituents are present, for example, between two substituents R', two substituents R x In the general formula (III) and the substituents R' and R x And any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
Herein, "R", R' ", R A ，R B Can optionally be linked to form a ring ", is intended to mean a group in which adjacent substituents are present, for example, between two substituents R', two substituents R A In between, two substituents R B Of a substituent R A And R', substituent R B And R', substituent R A And R' ", substituent R B And R '", and between substituents R" and R' ", any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
In this embodiment, L has the structure of formula 1 a The ligand being a bidentate ligand, i.e. L a The metal is coordinated only by the virtual bond shown in formula 1. No other means or sites for coordination to the metal are present in formula 1, e.g. R x1 Not coordinated to the metal M.
As used herein, "carbocyclic" means that the ring atoms comprising the cyclic group contain only carbon atoms and no heteroatoms. The cyclic group includes monocyclic rings, polycyclic rings (including spiro rings, bridged rings, fused rings, etc.). "carbocycle" includes saturated or unsaturated carbocycles such as alicyclic (e.g., cycloalkyl, cycloalkenyl, cycloalkynyl, etc.) and aromatic rings are both carbocycles.
As used herein, "heterocycle" means that the ring atoms constituting the cyclic group contain one or more heteroatoms which may be selected from nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, phosphorus atoms, silicon atoms, germanium atoms, boron atoms, and the like. The cyclic group includes monocyclic rings, polycyclic rings (including spiro rings, bridged rings, fused rings, etc.). "heterocyclic" includes saturated or unsaturated carbocyclic rings, e.g., both heteroaromatic and heteroaromatic rings are heterocyclic.
Herein, when n is 0, it indicates that L is absent in formula 2, i.e., formula 2 has the following structure:
when n is 1 and L is selected from a single bond, i.e., formula 2 has the following structure:
according to one embodiment of the invention, wherein the ring Cy, at each occurrence, is selected, identically or differently, in any one of the structures selected from the group consisting of:
wherein,
r represents, identically or differently on each occurrence, mono-, polysubstituted or unsubstituted; when multiple R are present in any structure, the R are the same or different;
r is selected, identically or differently on each occurrence, 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 heterocyclic group having 3 to 20 ring 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 alkynyl 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 alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
adjacent substituents R can optionally be linked to form a ring;
wherein, "#" indicates a position to which the metal M is attached,
is represented by the formula X 1 ，X 2 ，X 3 Or X 4 The location of the connection.
Herein, "adjacent substituents R can optionally be linked to form a ring", is intended to mean wherein any one or more of the group consisting between any two adjacent substituents R can be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
According to one embodiment of the invention, wherein the metal complex has M (L) a ) m (L b ) n (L c ) q A general formula (II) of (I);
wherein M is selected from the group consisting of Cu, ag, au, ru, rh, pd, os, ir, and Pt, the same or different at each occurrence; preferably, M is selected, identically or differently on each occurrence, from Pt or Ir;
L a 、L b and L c Are respectively a first, a second and a third ligand coordinated to the metal M, and L c And said L a Or L b Are the same or different; wherein L is a 、L b And L c Optionally linked to form a multidentate ligand;
m is selected from 1,2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2,m + n + q is equal to the oxidation state of metal M; when m is 2 or more, a plurality of L a The same or different; when n is equal to 2, two L b The same or different; when q is equal to 2, two of L c The same or different;
L a each occurrence, the same or different, is selected from the group consisting of:
x is selected from the group consisting of O, S, se, NR ', siR ' R ' and GeR ' R '; when two R 'are present at the same time, the two R's are the same or different;
R、R x and R x1 The same or different at each occurrence denotes mono-, poly-or no-substitution;
R x1 has a structure shown in formula 2:
R A and R B The same or different at each occurrence denotes mono-, poly-or no-substitution;
ring a and ring B are selected, identically or differently, from carbocycles having 3-30 ring atoms, heterocycles having 3-30 ring atoms, or combinations thereof;
A 1 ，A 2 ，B 1 ，B 2 e, identically or differently at each occurrence, is selected from C, N, B, P, CR "', siR" ' or GeR "';
n is 0 or 1;
l is selected from single bond, O, S, SO 2 Se, NR ", CR" R ", siR" R ", geR" R ", BR", PR ", P (O) R", R "C = CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, an arylene group having 6-30 carbon atoms, a heteroarylene group having 3-30 carbon atoms, and combinations thereof;
"Tn" indicates the attachment position of said formula 2;
adjacent R', R x Optionally linked to form a ring;
adjacent R can be optionally connected to form a ring;
adjacent R ', R', R A ，R B Optionally linked to form a ring;
L b and L c A structure, which is the same or different at each occurrence, selected from any one of the group consisting of:
wherein,
X b each occurrence, the same or different, is selected from the group consisting of: o, S, se, NR N1 ，CR C1 R C2 ；
R a And R b The same or different at each occurrence indicates mono-, poly-, or no substitution;
adjacent substituents R a ，R b ，R c ，R N1 ，R C1 And R C2 Can optionally be linked to form a ring;
R’，R”，R”’，R，R x ，R A ，R B ，R a ，R b ，R c ，R N1 ，R C1 and R C2 Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring 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 alkynyl 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 arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted germanyl having 0 to 20 carbon atoms, substituted or unsubstituted amino, cyano, mercapto, and combinations thereof.
As used herein, the "adjacent substituent R a ，R b ，R c ，R N1 ，R C1 And R C2 Can optionally be linked to form a ring ", is intended to denote a group of adjacent substituents therein, e.g. two substituents R a In between, two substituents R b Of a substituent R a And R b Of a substituent R a And R c Of R is a substituent b And R c Of a substituent R a And R N1 Of a substituent R b And R N1 Of R is a substituent a And R C1 Of a substituent R a And R C2 Of R is a substituent b And R C1 Of a substituent R b And R C2 And R is C1 And R C2 And any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be linked to each other to form a ring. For example, in the case of a liquid,
in (C) adjacent substituent R a ，R b Can optionally be linked to form a ring when R a When optionally joined to form a ring,
can form
The structure of (1).
According to one embodiment of the invention, the metal complex has Ir (L) a ) m (L b ) 3-m And is represented by formula 3:
wherein,
m is selected from 1,2 or 3; when m is selected from 1, two of L b The same or different; when m is selected from 2 or 3, a plurality of L a The same or different;
x is selected from the group consisting of O, S, se, NR ', siR ' R ' and GeR ' R '; when two R 'are present at the same time, the two R's are the same or different;
Y 1 -Y 4 is selected, identically or differently on each occurrence, from CR or N;
X 3 -X 8 selected from CR, identically or differently at each occurrence x ，CR x1 Or N;
X 3 -X 8 at least one of them is selected from CR x1 And R is x1 Has a structure shown in formula 2:
R A and R B The same or different at each occurrence denotes mono-, poly-or no-substitution;
ring a and ring B are selected, identically or differently, from carbocycles having 3 to 30 ring atoms, heterocycles having 3 to 30 ring atoms, or combinations thereof;
A 1 ，A 2 ，B 1 ，B 2 e, equal or different at each occurrence, is selected from C, N, B, P, CR "', siR" ' or GeR "';
n is 0 or 1;
l is selected from single bond, O, S, SO 2 Se, NR ", CR" R ", siR" R ", geR" R ", BR", PR ", P (O) R", R "C = CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, an arylene group having 6-30 carbon atoms, a heteroarylene group having 3-30 carbon atoms, and combinations thereof;
R’，R”，R”’，R，R x ，R A ，R B ，R 1 -R 8 each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring 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 alkynyl 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 unsubstitutedUnsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted alkylgermyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
adjacent R 1 -R 8 Optionally linked to form a ring;
adjacent R', R x Can be optionally connected to form a ring;
adjacent R can be optionally connected to form a ring;
adjacent R ', R', R A ，R B Can be optionally connected to form a ring.
As used herein, "adjacent R 1 -R 8 Can be optionally linked to form a ring "is intended to mean R 1 -R 8 Any one or more groups of any two adjacent substituents may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
According to an embodiment of the invention, wherein X 1 -X 8 Is selected, identically or differently on each occurrence, from CR x Or CR x1 。
According to an embodiment of the invention, wherein X 1 -X 8 Selected from CR, identically or differently at each occurrence x Or CR x1 And X 1 -X 8 Only one of which is selected from CR x1 。
According to an embodiment of the invention, wherein X 3 -X 8 Selected from CR, identically or differently at each occurrence x Or CR x1 。
According to an embodiment of the invention, wherein X 3 -X 8 Is selected, identically or differently on each occurrence, from CR x Or CR x1 And X 3 -X 8 Only one of which is selected from CR x1 。
In accordance with one embodiment of the present invention,wherein Y is 1 -Y 4 Each occurrence is selected, identically or differently, from CR.
According to an embodiment of the invention, wherein X 3 -X 8 At least one of which is N. For example X 3 -X 8 One of them is selected from N, or X 3 -X 8 Two of which are selected from N.
According to an embodiment of the invention, wherein X 1 -X 8 At least one of which is N. Such as X 1 -X 8 One of them is selected from N, or X 1 -X 8 Two of which are selected from N.
According to one embodiment of the present invention, wherein Y 1 -Y 4 At least one of which is N. For example Y 1 -Y 4 One of them is selected from N, or Y 1 -Y 4 Two of which are selected from N.
According to one embodiment of the invention, the metal complex has Ir (L) a ) m (L b ) 3-m And is represented by formula 3A:
wherein,
m is selected from 1,2 or 3; when m is selected from 1, two of L b The same or different; when m is selected from 2 or 3, a plurality of L a The same or different;
x is selected from the group consisting of O, S, se, NR ', siR ' R ' and GeR ' R '; when two R 'are present at the same time, the two R' are the same or different;
R、R x and R x1 The same or different at each occurrence indicates mono-, poly-or no-substitution;
R x1 has a structure shown in formula 2:
R A and R B At each occurrenceIdentically or differently, denotes mono-, poly-or unsubstituted;
ring a and ring B are selected, identically or differently, from carbocycles having 3-30 ring atoms, heterocycles having 3-30 ring atoms, or combinations thereof;
A 1 ，A 2 ，B 1 ，B 2 e, identically or differently at each occurrence, is selected from C, N, B, P, CR "', siR" ' or GeR "';
n is 0 or 1;
l is selected from single bond, O, S, SO 2 Se, NR ", CR" R ", siR" R ", geR" R ", BR", PR ", P (O) R", R "C = CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, an arylene group having 6-30 carbon atoms, a heteroarylene group having 3-30 carbon atoms, and combinations thereof;
R’，R”，R”’，R，R x ，R A ，R B ，R 1 -R 8 each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring 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 alkynyl 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 alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyA group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent R 1 -R 8 Can be optionally connected to form a ring;
adjacent R', R x Optionally linked to form a ring;
adjacent R can be optionally connected to form a ring;
adjacent R ', R', R A ，R B Can be optionally connected to form a ring.
According to one embodiment of the invention, wherein X is selected from O or S.
According to one embodiment of the invention, wherein X is selected from O.
According to one embodiment of the present invention, wherein A 1 、A 2 、B 1 And B 2 Selected from C, identically or differently at each occurrence.
According to one embodiment of the invention, wherein E is selected from N, identically or differently on each occurrence.
According to one embodiment of the invention, wherein R x Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted 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 alkylgermanyl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.
According to one embodiment of the invention, wherein R x Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 6 carbon atoms, substituted or unsubstituted alkylgermyl having 3 to 6 carbon atomsCyano, and combinations thereof.
According to one embodiment of the invention, wherein R x Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermyl, and combinations thereof.
According to one embodiment of the invention, wherein ring a and ring B, on each occurrence, are selected, identically or differently, from carbocycles having 5 to 12 ring atoms, heterocycles having 5 to 12 ring atoms, or combinations thereof.
According to one embodiment of the invention, wherein ring a and ring B are selected, identically or differently on each occurrence, from carbocyclic rings having 5 to 6 ring atoms, heterocyclic rings having 5 to 6 ring atoms, or combinations thereof.
According to one embodiment of the invention, wherein R x1 Has a structure represented by formula 4:
A 3 -A 6 selected from CR, identically or differently at each occurrence A Or N;
B 3 -B 6 selected from CR, identically or differently at each occurrence B Or N;
n is 0 or 1;
l is selected from single bond, O, S, SO 2 Se, NR ", CR" R ", siR" R ", geR" R ", BR", PR ", P (O) R", R "C = CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, an arylene group having 6-30 carbon atoms, a heteroarylene group having 3-30 carbon atoms, and combinations thereof;
R A 、R B and R' is the same or different at each occurrenceIs selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, a carbonyl group, an ester group, a cyano group, an isonicoyl group, a hydroxyl group, a mercapto group, a sulfonyl group, a mercapto group, and combinations thereof;
adjacent R', R A ，R B Optionally linked to form a ring;
"+" indicates the attachment position of said formula 4.
In this example, when n is 0, it indicates that L is absent in formula 4, i.e., formula 4 has the following structure:
when n is 1 and L is selected from a single bond, i.e., formula 4 has the following structure:
according to one embodiment of the present invention, wherein A 3 -A 6 Selected from CR, identically or differently at each occurrence A 。
According to an embodiment of the invention, wherein B 3 -B 6 Is selected, identically or differently on each occurrence, from CR B
According to one embodiment of the present invention, wherein A 3 -A 6 At least one of which is selected from N. For example A 3 -A 6 One of them is selected from N, or A 3 -A 6 Two of which are selected from N.
According to one embodiment of the invention, wherein B 3 -B 6 At least one of which is selected from N. Such as B 3 -B 6 One of them is selected from N, or B 3 -B 6 Two of which are selected from N.
According to one embodiment of the invention, wherein R A And R B Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted 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 alkylgermanyl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.
According to one embodiment of the invention, wherein R A And R B At least one selected from the group consisting of: hydrogen, deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 6 carbon atoms, a cyano group, and combinations thereof.
According to one embodiment of the invention, wherein R A And R B Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilicon having 3 to 6 carbon atomsA substituted or unsubstituted alkylgermyl group having 3 to 6 carbon atoms, a cyano group, and combinations thereof.
According to one embodiment of the invention, wherein R A And R B Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermyl, and combinations thereof.
According to an embodiment of the invention, wherein L is selected from the group consisting of a single bond, O, S, se, NR ", CR" R ", siR" R ", geR" R ", BR", PR ", P (O) R", R "C = CR", a heteroalkylene group having 1-10 carbon atoms, a cycloalkylene group having 3-10 carbon atoms, a heterocyclylene group having 3-10 ring atoms, an arylene group having 6-10 carbon atoms, a heteroarylene group having 3-10 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein L is selected from the group consisting of a single bond, O, S, NR ", R" C = CR ", phenylene.
According to one embodiment of the invention, wherein L is selected from single bonds.
According to one embodiment of the invention, wherein R "is selected, identically or differently on each occurrence, from the group consisting of: hydrogen, deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 6 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein R "is selected, identically or differently at each occurrence, from the group consisting of: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermyl, and combinations thereof.
According to one embodiment of the present invention, wherein X 3 -X 8 At least one of CR is selected from x1 。
According to an embodiment of the invention, wherein X 4 -X 8 At least one of CR is selected from x1 。
According to one embodiment of the present invention, wherein X 4 Selected from the group consisting of CR x1 。
According to one embodiment of the present invention, wherein X 5 -X 8 At least one of which is selected from CR x1 。
According to one embodiment of the present invention, wherein X 7 Or X 8 Selected from the group consisting of CR x1 。
According to one embodiment of the present invention, wherein X 8 Selected from the group consisting of CR x1 。
According to an embodiment of the invention, wherein X 1 -X 8 At least one of them is selected from CR x And said R is x Selected from cyano or fluorine, X 5 -X 8 At least one further one of (A) is selected from CR x1 。
According to an embodiment of the invention, wherein X 3 -X 8 At least one of them is selected from CR x And said R is x Selected from cyano or fluorine, X 5 -X 8 At least one further one of (A) is selected from CR x1 。
According to an embodiment of the invention, wherein X 5 -X 8 At least one of them is selected from CR x And said R is x Selected from cyano or fluoro, X 5 -X 8 At least one further one of (A) is selected from CR x1 。
According to one embodiment of the present invention, wherein X 7 Selected from the group consisting of CR x Said R is x Is cyano or fluorine, X 8 Selected from the group consisting of CR x1 。
According to one embodiment of the present invention, wherein X 8 Selected from the group consisting of CR x Said R is x Is cyano or fluorine, X 7 Selected from the group consisting of CR x1 。
According to one embodiment of the invention, wherein R x1 Each occurrence, identically or differently, is selected from the group consisting of:
according to An embodiment of the invention, wherein An 1 To An 118 The hydrogen in (b) can be partially or completely substituted with deuterium.
According to An embodiment of the invention, wherein An 1 To An 135 The hydrogen in (b) can be partially or completely substituted with deuterium.
According to one embodiment of the invention, wherein R is selected, identically or differently on each occurrence, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 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 amino groups having 6 to 20 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein R is selected, identically or differently on each occurrence, from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein at least one R is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 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 amino groups having 6 to 20 carbon atoms, and combinations thereof.
According to an embodiment of the invention, wherein at least one R is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein R 1 -R 8 Wherein at least one or at least two are selected from substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups of 3 to 20 ring carbon atoms, or combinations thereof, and all of said R' s 1 -R 4 And/or R 5 -R 8 The sum of the number of carbon atoms of (a) is at least 4.
According to one embodiment of the invention, wherein R 1 -R 4 In which at least one or at least two are selected from substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, and substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atomsOr a combination thereof, and all of said R 1 -R 4 And/or R 5 -R 8 The sum of the number of carbon atoms of (a) is at least 4.
According to one embodiment of the invention, wherein R 5 -R 8 Wherein at least one or at least two are selected from substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups of 3 to 20 ring carbon atoms, or combinations thereof, and all of said R' s 1 -R 4 And/or R 5 -R 8 The sum of the number of carbon atoms of (a) is at least 4.
According to one embodiment of the invention, wherein R 2 ，R 3 ，R 6 ，R 7 At least one or at least two or at least three or all are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein R 2 ，R 3 ，R 6 ，R 7 At least one or at least two or at least three or all of which are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein R 2 ，R 3 ，R 6 ，R 7 At least one or at least two or at least three or all are selected from the group consisting of: methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, tert-pentyl, any of the foregoing groups partially or totally deuterated, and deuterium.
According to one embodiment of the present invention, wherein L a Each occurrence being selected identically or differently from L a1 To L a1832 Group of (I), wherein L a1 To L a1832 The specific structure of (a) is shown in claim 18.
According to an embodiment of the invention, wherein L a1 To L a1832 The hydrogen atoms in (a) can be partially or completely replaced by deuterium.
According to one embodiment of the present invention, wherein L b Each occurrence, identically or differently, of a group selected from L b1 To L b334 Group of wherein L b1 To L b334 The specific structure of (A) is shown in claim 19.
According to one embodiment of the present invention, wherein L b1 To L b334 In which the hydrogen atoms can be partially or completely replaced by deuterium
According to one embodiment of the present invention, wherein L c Each occurrence being selected identically or differently from L c1 To L c360 Group of (I), wherein L c1 To L c360 The concrete structure of (3) is shown in claim 20.
According to one embodiment of the invention, the metal complex has Ir (L) a ) 3 Or Ir (L) a ) 2 L b Or IrL a (L b ) 2 Or Ir (L) a ) 2 L c Or IrL a (L c ) 2 Or Ir (L) a )(L b )(L c ) In which L is a Each occurrence being selected identically or differently from L a1 To L a1832 Group of (I) L b Each occurrence, identically or differently, of a group selected from L b1 To L b334 Group of (I), L c Each occurrence being selected identically or differently from L c1 To L c360 Group (i) of (ii); wherein L is a1 To L a1832 The specific structure of (A) is shown in claim 18, L b1 To L b334 Is defined in claim 19, L c1 To L c360 The specific structure of (A) is shown in claim 20.
According to one embodiment of the present invention, the metal complex has a group consisting of metal complex 1 to metal complex 1576, wherein the specific structures of metal complex 1 to metal complex 1576 are shown in claim 21.
According to one embodiment of the invention, wherein the metal complex has hydrogen energy in metal complex 1 through metal complex 1576 partially or completely substituted with deuterium.
According to one embodiment of the present invention, wherein L a Each occurrence being selected identically or differently from L a1 To L a1891 Group of wherein L a1 To L a1891 The specific structure of (a) is shown in claim 18.
According to an embodiment of the invention, wherein L a1 To L a1891 The hydrogen atoms in (a) can be partially or completely replaced by deuterium.
According to one embodiment of the present invention, wherein L b Each occurrence being selected identically or differently from L b1 To L b341 Group of wherein L b1 To L b341 The specific structure of (A) is shown in claim 19.
According to an embodiment of the invention, wherein L b1 To L b341 In which the hydrogen atoms can be partially or completely replaced by deuterium
According to an embodiment of the invention, wherein L c Each occurrence being selected identically or differently from L c1 To L c360 Group of wherein L c1 To L c360 The concrete structure of (3) is shown in claim 20.
According to one embodiment of the invention, the metal complex has Ir (L) a ) 3 Or Ir (L) a ) 2 L b Or IrL a (L b ) 2 Or Ir (L) a ) 2 L c Or IrL a (L c ) 2 Or Ir (L) a )(L b )(L c ) Structure of (1), wherein L a Each occurrence, identically or differently, of a group selected from L a1 To L a1891 Group of (I), L b Each occurrence being selected identically or differently from L b1 To L b341 Group of (I) L c Each occurrence, identically or differently, of a group selected from L c1 To L c360 Group (i) of (ii); wherein L is a1 To L a1891 Is defined in claim 18, L b1 To L b341 The specific structure of (A) is shown in claim 19, L c1 To L c360 The specific structure of (A) is shown in claim 20.
According to one embodiment of the present invention, wherein the metal complex has the group consisting of metal complex 1 through metal complex 1646, wherein the specific structures of metal complex 1 through metal complex 1646 are shown in claim 21.
According to one embodiment of the invention, wherein the metal complex has hydrogen energy in metal complex 1 through metal complex 1646 partially or fully substituted with deuterium.
There is also disclosed, in accordance with an embodiment of the present invention, an electroluminescent device, including: an anode, a cathode, and an organic layer disposed between the anode and the cathode, at least one of the organic layers comprising a metal complex as in any of the preceding embodiments.
According to an embodiment of the present invention, wherein the organic layer including the metal complex in the electroluminescent device is a light emitting layer.
According to one embodiment of the present invention, wherein the light emitting layer in the electroluminescent device emits green light.
According to one embodiment of the present invention, wherein the light emitting layer of the electroluminescent device comprises a host compound comprising one or more species; when the host compound is a combination of a plurality of compounds, at least one n-type host compound and at least one p-type host compound are included.
According to one embodiment of the present invention, the light-emitting layer of the electroluminescent device further comprises a first host compound.
According to one embodiment of the present invention, the light-emitting layer of the electroluminescent device further comprises a first host compound and a second host compound.
According to an embodiment of the present invention, wherein at least one of the host compounds in the electroluminescent device comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.
According to one embodiment of the invention, wherein the first host compound has a structure represented by formula X:
wherein,
L x each occurrence identically or differently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
v is selected, identically or differently on each occurrence, from C, CR v Or N, and at least one of V is C, and with L x Connecting;
t is selected, identically or differently on each occurrence, from C, CR t Or N, and at least one of T is C, and with L x Connecting;
R v and R t Each occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring 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 atomsSubstituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
Ar 1 each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
adjacent substituents R v And R t Can optionally be linked to form a ring.
In this example, the "adjacent substituents R v And R t Can optionally be linked to form a ring ", is intended to denote a group of adjacent substituents therein, e.g. two substituents R v In between, two substituents R t In between, two substituents R v And R t And any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
According to one embodiment of the invention, wherein the first host compound has a structure represented by one of formula X-a to formula X-j:
wherein,
L x each occurrence, which is the same or different, is selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
v is selected, identically or differently on each occurrence, from CR v Or N;
t is selected, identically or differently on each occurrence, from CR t Or N;
R v and R t Identical in each occurrence orVariously selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
Ar 1 each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
adjacent substituents R v And R t Can optionally be linked to form a ring.
According to one embodiment of the present invention, wherein the second host compound has a structure represented by formula 5:
wherein,
E 1 -E 6 selected, identically or differently at each occurrence, from C, CR e Or N, and E 1 -E 6 At least two of which are N, E 1 -E 6 At least one of which is C and is linked to formula A;
wherein,
q is the same or different at each occurrence and is selected from the group consisting of O, S, se, N, NR Q ，CR Q R Q ，SiR Q R Q ，GeR Q R Q And R Q C＝CR Q Group (i) of (ii); when two R are simultaneously present Q When two R are present Q May be the same or different;
p is 0 or 1; r is 0 or 1;
when Q is selected from N, p is 0, r is 1;
when Q is selected from the group consisting of O, S, se, NR Q ，CR Q R Q ，SiR Q R Q ，GeR Q R Q And R Q C＝CR Q When group (b) is formed, p is 1, r is 0;
l is selected, identically or differently on each occurrence, from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof;
Q 1 -Q 8 selected, identically or differently at each occurrence, from C, CR q Or N;
R e ，R Q and R q Each occurrence, identically or differently, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring 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 alkynyl 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 atomsAn alkylsilyl group of 3-20 carbon atoms, a substituted or unsubstituted arylsilyl group of 6-20 carbon atoms, a substituted or unsubstituted alkylgermyl group of 3-20 carbon atoms, a substituted or unsubstituted arylgermyl group of 6-20 carbon atoms, a substituted or unsubstituted amino group of 0-20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
"+" represents the connection position of formula A and formula 5;
adjacent substituents R e ，R Q ，R q Can optionally be joined to form a ring.
As used herein, the "adjacent substituents R e ，R Q ，R q Can optionally be linked to form a ring ", is intended to denote a group of adjacent substituents therein, e.g. two substituents R e In between, two substituents R Q In between, two substituents R q In between, two substituents R Q And R q And any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
According to one embodiment of the invention, the metal complex in the electroluminescent device is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 1-30% of the total weight of the light-emitting layer.
According to one embodiment of the invention, the metal complex in the electroluminescent device is doped in the first host compound and the second host compound, and the weight of the metal complex accounts for 3% -13% of the total weight of the light-emitting layer.
According to an embodiment of the present invention, the organic electroluminescent device further comprises a hole injection layer, and the hole injection layer may be a single material functional layer or a functional layer comprising multiple materials, wherein the multiple materials contained in the hole injection layer are most commonly a hole transport material doped with a p-type conductive doping material in a certain proportion. Common p-type doped materials are:
according to another embodiment of the invention, a composition is also disclosed, which comprises a metal complex, wherein the specific structure of the metal complex is shown in any one of the previous embodiments.
In combination with other materials
The materials described herein for use in particular layers in an organic light emitting device may be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. patent application Ser. No. 0132-0161, paragraphs 2016/0359122A1, which is hereby incorporated by reference in its entirety. The materials described or referenced therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that can be used in combination.
Materials described herein as useful for particular layers in organic light emitting devices can be used in combination with a variety of other materials present in the device. For example, the light emitting dopants disclosed herein may be used in conjunction with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application US2015/0349273A1, paragraphs 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
In the examples of material synthesis, all reactions were carried out under nitrogen unless otherwise stated. All reaction solvents were anhydrous and used as received from commercial sources. The synthesis product is subjected to structural validation and characterization using one or more equipment conventional in the art (including, but not limited to, bruker's nuclear magnetic resonance apparatus, shimadzu's liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, shanghai prism-based fluorescence spectrophotometer, wuhan Corset's electrochemical workstation, anhui Beidek's sublimator, etc.) in a manner well known to those skilled in the art. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, an evaporator manufactured by Angstrom Engineering, an optical test system manufactured by Fushida, suzhou, an ellipsometer manufactured by Beijing Mass., etc.) in a manner well known to those skilled in the art. Since the relevant contents of the above-mentioned device usage, testing method, etc. are known to those skilled in the art, the inherent data of the sample can be obtained with certainty and without being affected, and therefore, the relevant contents are not described in detail in this patent.
Examples of Material Synthesis
Synthesis example 1: synthesis of Metal Complex 765
Under the protection of nitrogen gas at room temperature, the intermediate 1 (2.0 g,2.2 mmol) and the intermediate 2 (1.2 g,2.7 mmol) are sequentially added into a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL), and the temperature is raised to 100 ℃ for reaction for 120h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain metal complex 765 (1.0 g,0.9mmol, 40%) as a yellow solid. The product was identified as the target product and had a molecular weight of 1047.3.
Synthesis example 2: synthesis of Metal Complex 785
Under the protection of nitrogen gas at room temperature, the intermediate 1 (2.0g, 2.2mmol) and the intermediate 3 (1.3g, 2.7mmol) are sequentially added into a mixed solvent of 2-ethoxyethanol (20.0 ml) and DMF (20.0 ml), and the temperature is increased to 100 ℃ for reaction for 120 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain metal complex 785 (1.0 g,0.8mmol, 36%) as a yellow solid. The product was identified as the target product and had a molecular weight of 1159.5.
Synthetic example 3: synthesis of Metal Complex 773
Intermediate 1 (2.1g, 2.5mmol) and intermediate 4 (1.3g, 2.8mmol) were added in this order to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL) at room temperature under nitrogen atmosphere, and the temperature was raised to 100 ℃ to react for 120 hours. After the reaction was cooled, the reaction liquid was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain metal complex 773 (0.5g, 0.5mmol, 20%) as a yellow solid. The product was identified as the target product and had a molecular weight of 1075.4.
Synthetic example 4: synthesis of Metal Complex 697
Intermediate 1 (2.5g, 3.0 mmol) and intermediate 5 (1.6g, 4.0 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL) at room temperature under nitrogen protection, and the mixture was heated to 100 ℃ for 120 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain metal complex 697 (1.0 g,1.0mmol, 33%) as a yellow solid. The product was identified as the target product and had a molecular weight of 1022.3.
Synthesis example 5: synthesis of Metal Complex 778
Under the protection of nitrogen gas at room temperature, the intermediate 1 (3.0g, 3.7mmol) and the intermediate 6 (2.8g, 5.7mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL), and the temperature was raised to 100 ℃ to react for 120 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain metal complex 778 (1.5g, 1.4mmol, 38%) as a yellow solid. The product was identified as the target product and had a molecular weight of 1103.4.
Synthetic example 6: synthesis of Metal Complex 782
Intermediate 1 (1.4 g,1.7 mmol) and intermediate 7 (1.1 g,2.0 mmol) were added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL) in this order at room temperature under nitrogen protection, and the temperature was raised to 100 ℃ for 120 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain metal complex 782 (0.5g, 0.4mmol, 24%) as a yellow solid. The product was identified as the target product and had a molecular weight of 1159.5.
Synthetic example 7: synthesis of Metal Complex 777
Under the protection of nitrogen gas at room temperature, the intermediate 1 (1.0g, 1.2mmol) and the intermediate 8 (0.7g, 1.5mmol) are sequentially added into a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL) and heated to 100 ℃ for reaction for 120 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain metal complex 777 (0.3g, 0.3mmol, 25%) as a yellow solid. The product was identified as the target product and had a molecular weight of 1103.4.
Synthetic example 8: synthesis of Metal Complex 867
Intermediate 1 (1.7 g, 2.1mmol) and intermediate 9 (1.2g, 2.7 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL) at room temperature under nitrogen protection, and the temperature was raised to 100 ℃ for reaction for 120 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain 867 (1.0 g,0.9mmol, 43%) as a yellow solid. The product was identified as the target product and had a molecular weight of 1049.4.
Synthetic example 9: synthesis of Metal Complex 799
Intermediate 1 (1.9g, 2.3mmol) and intermediate 10 (1.5g, 3.5mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL) at room temperature under nitrogen, and the mixture was heated to 100 ℃ for 96h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain metal complex 799 (1.55g, 1.48mmol, 64%) as a yellow solid. The product was identified as the target product and had a molecular weight of 1047.3.
Synthetic example 10: synthesis of Metal Complex 839
Intermediate 1 (1.9g, 2.3mmol) and intermediate 11 (1.3g, 3.1mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL) at room temperature under nitrogen, and the mixture was warmed to 100 ℃ for 120h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain metal complex 839 (1.3g, 1.27mmol, 55%) as a yellow solid. The product was identified as the target product and had a molecular weight of 1040.3.
Synthetic example 11: synthesis of Metal Complex 1577
Intermediate 25 (3.7g, 5.1mmol) and intermediate 13 (2.0g, 7.6mmol) were sequentially added to 290ml of ethanol at room temperature under nitrogen protection, and the temperature was raised to 80 ℃ to react for 24 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain intermediate 14 (1.75g, 2.3mmol, 45%).
At room temperature, under the protection of nitrogen, the intermediate 14 (0.6 g,0.7 mmol) and carbazole (0.33g, 2.0 mmol) are sequentially added into 30ml of DMF solvent, and the temperature is raised to 100 ℃ for reaction for 24h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain 1577 (0.45g, 0.42mmol, 60%). The product was identified as the target product and had a molecular weight of 911.2.
Synthetic example 12: metal complex 789
Intermediate 1 (2.5g, 3.0 mmol) and intermediate 15 (1.6g, 3.6 mmol) were added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL) in this order at room temperature under nitrogen protection, and the temperature was raised to 100 ℃ to react for 120 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain 789 (1.66g, 1.6mmol, 52%) of the metal complex. The product was identified as the target product and had a molecular weight of 1055.4.
Synthetic example 13: synthesis of Metal Complex 725
Intermediate 1 (2.5g, 3.0mmol) and intermediate 16 (1.7g, 4.1mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (50.0 mL) and DMF (50.0 mL) at room temperature under nitrogen protection, and the temperature was raised to 100 ℃ to react for 72 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain metal complex 725 (0.9 g,0.88mmol, 29%) as a yellow solid. The product was identified as the target product and had a molecular weight of 1022.4.
Synthesis example 14: synthesis of Metal Complex 797
Intermediate 1 (0.88g, 1.1mmol) and intermediate 17 (0.6g, 1.2mmol) were added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL) in this order at room temperature under nitrogen, and the temperature was raised to 100 ℃ for 120 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain metal complex 797 (0.36g, 0.32mmol, 29%) as a yellow solid. The product was identified as the target product and had a molecular weight of 1123.4.
Synthetic example 15: synthesis of metal complex 1584
Intermediate 1 (2.1g, 2.5mmol) and intermediate 18 (1.3g, 2.8mmol) were added in this order to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL) at room temperature under nitrogen atmosphere, and the temperature was raised to 100 ℃ to react for 120 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain 1584 (0.54g, 0.50mmol, 20%) as a yellow solid. The product was identified as the target product and had a molecular weight of 1083.3.
Synthetic example 16: synthesis of Metal Complex 1606
Intermediate 1 (2.0g, 2.5mmol) and intermediate 19 (1.8g, 3.3mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL) at room temperature under nitrogen protection, and the temperature was raised to 100 ℃ to react for 120 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain metal complex 1606 (1.0 g,0.85mmol, 34%) as a yellow solid. The product was identified as the target product and had a molecular weight of 1163.4.
Synthetic example 17: synthesis of Metal Complex 1598
Intermediate 1 (0.5g, 0.6mmol) and intermediate 20 (0.3g, 0.7mmol) were added to a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL) in this order at room temperature under nitrogen, and the temperature was raised to 100 ℃ to react for 120 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain metal complex 1598 (0.3g, 0.28mmol, 47%) as a yellow solid. The product was identified as the target product and had a molecular weight of 1065.3.
Synthetic example 18: synthesis of Metal complexes 959
Under the protection of nitrogen at room temperature, sequentially adding the intermediate 21 (1.5g, 1.61mmol) and the intermediate 22 (1.05g, 1.93mmol) into a mixed solvent of 2-ethoxyethanol (20.0 mL) and DMF (20.0 mL), and heating to 100 ℃ for reaction for 120h. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain metal complex 959 (0.61g, 0.54mmol, 33%) as a yellow solid. The product was identified as the target product and had a molecular weight of 1271.6.
Synthetic example 19: synthesis of Metal Complex 1612
Intermediate 21 (2.0 g,2.2 mmol) and intermediate 23 (1.3 g, 2.8mmol) were added in this order to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL) at room temperature under nitrogen, and the temperature was raised to 100 ℃ to react for 120 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain metal complex 1612 (0.47g, 0.45mmol, 20%) as a yellow solid. The product was identified as the target product and had a molecular weight of 1184.5.
Synthesis example 20: synthesis of Metal Complex 1643
Intermediate 24 (2.0 g,2.2 mmol) and intermediate 26 (1.3 g,2.6 mmol) were added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL) in this order at room temperature under nitrogen, and the temperature was raised to 100 ℃ for 120 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain metal complex 1643 (0.75g, 0.4mmol, 28%) as a yellow solid. The product was identified as the target product and had a molecular weight of 1216.6.
Synthetic example 21: synthesis of Metal Complex 1645
Intermediate 27 (2.0 g,2.5 mmol) and intermediate 28 (1.6 g,3.6 mmol) were sequentially added to a mixed solvent of 2-ethoxyethanol (30.0 mL) and DMF (30.0 mL) at room temperature under nitrogen protection, and the temperature was raised to 100 ℃ to react for 120 hours. After the reaction was cooled, the reaction solution was concentrated under reduced pressure and purified by column chromatography (dichloromethane/petroleum ether = 1/1) to obtain metal complex 1645 (0.75g, 0.4mmol, 28%) as a yellow solid. The product was identified as the target product and had a molecular weight of 1013.3.
Device embodiments
Device example 1
First, a glass substrate, having an Indium Tin Oxide (ITO) anode 80nm thick, was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate is then mounted on a substrate holder and loaded into a vacuum chamber. Organic layers specified below, in a vacuum of about 10 degrees -8 In the case of torr, the evaporation was carried out on the ITO anode in turn by thermal vacuum evaporation at a rate of 0.2-2 a/s. Compound HI was used as Hole Injection Layer (HIL). The compound HT is used as a Hole Transport Layer (HTL). The compound H1 is used as an Electron Blocking Layer (EBL). The metal complex 697 of the present invention is then a dopant and co-deposited with compound H1 and compound H2 to serve as an emissive layer (EML). On the EML, compound HB acts as a Hole Blocking Layer (HBL). On HBL, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited as an Electron Transport Layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) was evaporated to a thickness of 1nm as an electron injection layer, and 120nm of aluminum as a cathode. The device was then transferred back to the glove box and encapsulated with a glass lid to complete the device.
Device comparative example 1
Device comparative example 1 was the same as device example 1 except that the compound GD1 was used in the light-emitting layer (EML) instead of the metal complex 697 of the present invention.
The detailed device layer structure and thickness are shown in the table below. Wherein more than one layer of the materials used is obtained by doping different compounds in the stated weight ratios.
Table 1 partial device structures of example 1 and comparative example 1
The material structure used in the device is as follows:
the IVL characteristics of the device were measured. At a current density of 15mA/cm 2 The CIE data of the device is measured, the maximum emission wavelength lambda max Full width at half maximum (FWHM), device voltage (V), current Efficiency (CE), power Efficiency (PE) and External Quantum Efficiency (EQE). These data are recorded and presented in table 2.
Table 2 device data for example 1 and comparative example 1
As can be seen from the data of example 1 versus comparative example 1 of table 2: the metal complex 697 of the invention differs from the comparative compound GD1 only in the ligand L a The carbazole substituent group is replaced by phenyl, and the carbazole substituent group is applied to the same organic electroluminescent device, so that the voltage is reduced by 0.26V, the CE is improved by 8.4%, the PE is improved by 16.1%, and the EQE is improved by 9.7%. This demonstrates that the inclusion of a compound having R provided by the present invention x1 L of a substituent a The metal complex of the ligand can obtain a device with more excellent performance, can comprehensively improve the performance of each aspect of the device, and finally greatly improves the comprehensive performance of the device.
Device example 2
Device example 2 was implemented in the same manner as device example 1 except that the metal complex 867 was used in the light emitting layer (EML) instead of the metal complex 697 of the present invention.
Device comparative example 2
Device comparative example 2 was implemented in the same manner as in device example 1 except that the compound GD2 was used in the light-emitting layer (EML) instead of the metal complex 697 of the present invention.
The detailed device layer structure and thickness are shown in table 3. In which more than one layer of the materials used is obtained by doping different compounds in the stated weight ratios.
Table 3 partial device structures of example 2 and comparative example 2
The structure of the material used in the device is as follows:
the IVL characteristics of the device were measured. At a current density of 15mA/cm 2 The CIE data of the devices, the maximum emission wavelength lambda, were measured max Full width at half maximum (FWHM), device voltage (V), current Efficiency (CE), power Efficiency (PE) and External Quantum Efficiency (EQE). These data are recorded and presented in table 4.
Table 4 device data of example 2 and comparative example 2
As can be seen from the data of example 2 versus comparative example 2 of table 4: the metal complexes 867 according to the invention and the comparative compounds GD2 differ only by the ligand L a The substituted group of the diphenyl amino group is replaced by deuterium, and the deuterium is applied to the same organic electroluminescent device, so that the voltage is reduced by 0.2V, the CE is improved by 6.7 percent, the PE is improved by 10.7 percent, and the EQE is improved by 8.2 percent. This demonstrates that the inclusion of a compound having R provided by the present invention x1 L of a substituent a The metal complex of the ligand can obtain a device with more excellent performance, can comprehensively improve the performance of each aspect of the device, and finally greatly improves the comprehensive performance of the device.
Device example 3
Device example 3 is implemented in the same manner as device example 1 except that a metal complex 765 is used in the light-emitting layer (EML) instead of the metal complex 697 of the present invention.
Device example 4
Device example 4 was implemented in the same manner as device example 1 except that a metal complex 785 was used in place of the metal complex 697 of the present invention in the light-emitting layer (EML).
Device comparative example 4
Device comparative example 4 was implemented in the same manner as in device example 1 except that the compound GD3 was used in the light-emitting layer (EML) instead of the metal complex 697 of the present invention.
The detailed device layer structure and thickness are shown in table 5. Wherein more than one layer of the materials used is obtained by doping different compounds in the stated weight ratios.
Table 5 partial device structures of example 3, example 4 and comparative example 3
The material structure used in the device is as follows:
the IVL characteristics of the device were measured. At a current density of 15mA/cm 2 The CIE data of the devices, the maximum emission wavelength lambda, were measured max Full width at half maximum (FWHM), device voltage (V), current Efficiency (CE), power Efficiency (PE) and External Quantum Efficiency (EQE). These data are recorded and presented in table 6.
Table 6 device data for example 3, example 4 and comparative example 3
Table 6 data for example 3, example 4 versus comparative example 3 show that: at L a Based on the ligands having cyano substituents, metal complexes 765, 785 and GD3 of the comparative example differ only in ligand L a The substituted or unsubstituted carbazole substituent at (a) is replaced with a phenyl group, and this is applied to the same organic compoundIn the electroluminescent device, the voltage is respectively reduced by 0.29V and 0.35V, the CE is respectively improved by 5.3 percent and 10.6 percent, the PE is respectively improved by 10.4 percent and 22.1 percent, and the EQE is respectively improved by 5.8 percent and 10.8 percent. Meanwhile, in examples 3 and 4, the half-peak widths were narrowed by 1.4nm and 0.5nm, respectively, without variation in the maximum emission wavelength, as compared with comparative example 3, indicating that more saturated green emission was obtained. It was demonstrated above that the compounds provided by the present invention comprise compounds having R x1 L of a substituent a The metal complex of the ligand can obtain a device with more excellent performance, can comprehensively improve the performance of each aspect of the device, and finally greatly improves the comprehensive performance of the device.
In summary, the invention provides compositions comprising compounds having R x1 L of a substituent a The metal complex of the ligand can obtain devices with more excellent performance, such as reduction of device voltage, improvement of CE, PE and EQE, comprehensive improvement of various aspects of device performance, and finally great improvement of device comprehensive performance.
Device example 5
Device example 5 was implemented in the same manner as device example 1 except that a metal complex 725 was used in the light-emitting layer (EML) instead of the metal complex 697 of the present invention.
Device comparative example 4
Device comparative example 4 was implemented in the same manner as in device example 1 except that the compound GD4 was used in the light-emitting layer (EML) instead of the metal complex 697 of the present invention.
Device example 6
Device example 6 is the same as device example 1 except that in the light emitting layer (EML) a metal complex 1577 is used instead of the metal complex 697 of the present invention, wherein the ratio of compound H1: compound H2: metal complex 1577= 56.
Device comparative example 5
Device comparative example 5 was implemented in the same manner as in device example 6, except that the compound GD5 was used in the light emitting layer (EML) instead of the metal complex 1577 of the present invention.
The detailed device layer structure and thickness are shown in table 7. Wherein more than one layer of the materials used is obtained by doping different compounds in the stated weight ratios.
Table 7 partial device structures of example 5 and example 6 and comparative examples 4 and 5
The structure of the material used newly in the device is as follows:
the IVL characteristics of the device were measured. At a current density of 15mA/cm 2 The CIE data of the device is measured, the maximum emission wavelength lambda max Full width at half maximum (FWHM), device voltage (V), current Efficiency (CE), power Efficiency (PE) and External Quantum Efficiency (EQE). These data are recorded and presented in table 8.
TABLE 8 device data for example 5, example 6 and comparative examples 4, 5
As can be seen from the data in table 8: example 5 compared to comparative example 4, the metal complex 725 of the invention and the comparative example compound GD4 differ only in the ligand L a The carbazole substituent group is replaced by biphenyl, and the carbazole substituent group is applied to the same organic electroluminescent device, compared with comparative example 4, in example 5, the voltage is reduced by 0.30V, the CE is improved by 2.5%, the PE is improved by 10.5%, and the EQE is improved by 3.6%.
Example 6 compared to comparative example 5, the metal complex 1577 according to the invention differs from the comparative compound GD5 only in the ligand L a The carbazole substituent is replaced by a deuterated methyl group, and the substituted carbazole substituent is applied to the same compoundIn the organic electroluminescent device, in example 6, the voltage was reduced by 0.10V, the CE was improved by 13.0%, the PE was improved by 17.5%, and the EQE was improved by 11.8% as compared with comparative example 5.
This demonstrates that inclusion of a compound having R provided by the present invention x1 L of a substituent a The metal complex of the ligand can obtain a device with more excellent performance, can comprehensively improve the performance of each aspect of the device, and finally greatly improves the comprehensive performance of the device.
Device example 7
Device example 7 was carried out in the same manner as in device example 1 except that the metal complex 789 was used in place of the metal complex 697 of the present invention in the light-emitting layer (EML).
Device example 8
Device example 8 was conducted in the same manner as in device example 1 except that the metal complex 1584 was used in place of the metal complex 697 of the present invention in the light-emitting layer (EML).
Device example 9
Device example 9 was carried out in the same manner as in device example 1 except that the metal complex 797 was used in the light-emitting layer (EML) in place of the metal complex 697 of the present invention.
Device example 10
Device example 10 was implemented in the same manner as in device example 1 except that the metal complex 1606 was used in place of the metal complex 697 of the present invention in the light-emitting layer (EML).
Device example 11
Device example 11 was carried out in the same manner as in device example 1 except that the metal complex 959 was used in the light-emitting layer (EML) in place of the metal complex 697 of the present invention.
Device example 12
Device example 12 was implemented in the same manner as in device example 1, except that a metal complex 1643 was used in the light-emitting layer (EML) instead of the metal complex 697 of the present invention, in which the compound H1: compound H2: metal complex 1643= 71.
The detailed device layer structure and thickness are shown in table 9. Wherein more than one layer of the materials used is obtained by doping different compounds in the stated weight ratios.
Table 9 partial device structures of examples 7 to 12
The structure of the material used in the device is as follows:
the IVL characteristics of the device were measured. At a current density of 15mA/cm 2 The CIE data of the devices, the maximum emission wavelength lambda, were measured max Full width at half maximum (FWHM), device voltage (V), current Efficiency (CE), power Efficiency (PE) and External Quantum Efficiency (EQE). These data are recorded and shown in table 10.
TABLE 10 device data for examples 7 to 12 and comparative example 3
From the data in Table 10, it can be seen that examples 7 through 10 compare comparative example 3, at L a Based on the ligands having cyano substituents, the metal complexes 789, 1584, 797, 1606 of the invention and the comparative compound GD3 differ only in the ligand L a The differently substituted carbazolyl is replaced by phenyl, and the phenyl is applied to the same organic electroluminescent device, the half-peak widths are respectively narrowed by 0.5nm, 2.1nm, 1.0nm and 2.3nm, the voltages are respectively reduced by 0.40V, 0.46V, 0.26V and 0.29V, the CE is respectively improved by 4.3%, 7.4%, 4.3% and 3.2%, the PE is respectively improved by 15.6%, 22.1%, 11.7% and 11.7%, and the EQE is respectively improved by 3.7%, 6.5%, 5.0% and 3.9%. This demonstrates that the inclusion of a compound having R provided by the present invention x1 L of a substituent a The metal complex of the ligand can obtain a device with more excellent performance, can comprehensively improve the performance of each aspect of the device, and finally greatly improves the comprehensive performance of the device.
The data for example 11 and example 12 show that: the metal complexes 959 and 1643 of the invention have R at both x1 L of a substituent a In the case of ligands, each at L a Ligand and L b The ligands have different substituents. The EQE of the device is above 25%, the CE is about 100cd/A, and the EQE of the embodiment 11 is more than 26.55%. Meanwhile, the PE and the voltage of the composite material are also at higher levels, and the composite material shows high comprehensive performance of the device.
All the above show that the compound containing the compound with R provided by the invention x1 L of a substituent a The metal complex of the ligand can obtain a device with more excellent performance, can comprehensively improve the performance of each aspect of the device, and finally greatly improves the comprehensive performance of the device.
Device example 13
Device example 13 was implemented in the same manner as device example 1 except that metal complex 799 was used in place of metal complex 697 of the present invention in the light-emitting layer (EML).
Device comparative example 6
Device comparative example 6 was the same as device example 1 except that the compound GD6 was used in the light emitting layer (EML) instead of the metal complex 697 of the present invention.
The detailed device layer structure and thickness are shown in table 11. Wherein more than one layer of the materials used is obtained by doping different compounds in the stated weight ratios.
Table 11 partial device structures of example 13 and comparative example 6
The structure of the material used in the device is as follows:
the IVL characteristics of the device were measured. In thatThe current density is 15mA/cm 2 The CIE data of the device is measured, the maximum emission wavelength lambda max Full width at half maximum (FWHM), device voltage (V), current Efficiency (CE), power Efficiency (PE) and External Quantum Efficiency (EQE). These data are recorded and shown in table 12.
TABLE 12 device data for examples 7 to 14 and comparative examples 3 and 6
Example 13 as seen by comparison to comparative example 6: the metal complex 799 of the invention differs from the comparative compound GD6 only in the ligand L a The carbazole substituent group is replaced by phenyl, and the carbazole substituent group and the phenyl are all applied to the same organic electroluminescent device, so that the half-peak width of the organic electroluminescent device in example 15 is narrowed by 2.0nm, the voltage is reduced by 0.11V, the CE is improved by 5.8%, the PE is improved by 9.5%, and the EQE is improved by 6.5%.
The above shows that the compound provided by the invention contains the compound having R x1 L of a substituent a The metal complex of the ligand can obtain a device with more excellent performance, can comprehensively improve the performance of each aspect of the device, and finally greatly improves the comprehensive performance of the device.
Device example 14
Device example 14 was implemented in the same manner as device example 1 except that a metal complex 839 was used in place of the metal complex 697 of the present invention in the light-emitting layer (EML), wherein the ratio of the compound H1: compound H2: metal complex 839= 71.
Device comparative example 7
Device comparative example 7 was implemented in the same manner as in device example 14 except that the present metal complex 839 was replaced with the compound GD7 in the light-emitting layer (EML).
The detailed device layer structure and thickness are shown in table 13. Wherein more than one layer of the materials used is obtained by doping different compounds in the stated weight ratios.
Table 13 partial device structures of example 14 and comparative example 7
The structure of the material used newly in the device is as follows:
the IVL characteristics of the device were measured. At a current density of 15mA/cm 2 The CIE data of the devices, the maximum emission wavelength lambda, were measured max Full width at half maximum (FWHM), device voltage (V), current Efficiency (CE), power Efficiency (PE) and External Quantum Efficiency (EQE). These data are recorded and shown in table 14.
TABLE 14 device data for example 14 and comparative example 7
From the device data in Table 14, it can be seen that example 14 compares to comparative example 7 at L a The metal complex 839 of the invention differs from the comparative compound GD7 only in the ligand L on the basis that the ligand has a fluorine substituent a The carbazole substituent group is replaced by phenyl, and the phenyl carbazole substituent group is applied to the same organic electroluminescent device, the voltage is reduced by 0.66V, the CE is improved by 4.6%, the PE is improved by 23.3%, and the EQE is improved by 5.5%. It was demonstrated above that the compounds provided by the present invention comprise compounds having R x1 L of a substituent a The metal complex of the ligand can obtain a device with more excellent performance, can comprehensively improve the performance of each aspect of the device, and finally greatly improves the comprehensive performance of the device.
In summary, the invention provides compositions comprising compounds having R x1 L of a substituent a The metal complex of the ligand can obtain a device with more excellent performanceFor example, the voltage of the device is reduced, and the CE, PE and EQE are improved, so that the performance of the device in all aspects can be comprehensively improved, and the comprehensive performance of the device is greatly improved finally.
It should be understood that the various embodiments described herein are illustrative only and are not intended to limit the scope of the invention. Thus, the invention as claimed may include variations from the specific embodiments and preferred embodiments described herein, as will be apparent to those skilled in the art. Many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the present invention. It should be understood that various theories as to why the present invention works are not intended to be limiting.
Claims (26)
1. A metal complex comprising a metal M, and a ligand L coordinated to the metal M a Wherein L is a Has a structure represented by formula 1:
in the case of the formula 1, the compound,
the metal M is selected from metals having a relative atomic mass greater than 40;
ring Cy is selected, identically or differently on each occurrence, from a substituted or unsubstituted aromatic ring having 6-24 ring atoms, a substituted or unsubstituted heteroaromatic ring having 5-24 ring atoms, or a combination thereof; and the ring Cy comprises at least 3 carbon atoms;
cy is linked to the metal M through a metal-carbon or metal-nitrogen bond;
x is selected, identically or differently on each occurrence, from the group consisting of O, S, se, NR ', siR ' R ' and GeR ' R '; when two R 'are present at the same time, the two R' are the same or different;
X 1 -X 8 is selected, identically or differently on each occurrence, from C, CR x ，CR x1 Or N; x 1 -X 4 At least one of which is C and is connected to the ring Cy;
X 1 、X 2 、X 3 or X 4 Is linked to the metal M by a metal-carbon or metal-nitrogen bond;
X 1 -X 8 at least one of them is selected from CR x1 And R is x1 Has a structure shown in formula 2:
wherein, in the formula 2,
R A and R B The same or different at each occurrence indicates mono-, poly-or no-substitution;
ring a and ring B are selected, identically or differently, from carbocycles having 3 to 30 ring atoms, heterocycles having 3 to 30 ring atoms, or combinations thereof;
n is 0 or 1;
A 1 ，A 2 ，B 1 ，B 2 e, identically or differently at each occurrence, is selected from C, N, B, P, CR "', siR" ' or GeR "';
l is selected from single bond, O, S, SO 2 Se, NR ", CR" R ", siR" R ", geR" R ", BR", PR ", P (O) R", R "C = CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, an arylene group having 6-30 carbon atoms, a heteroarylene group having 3-30 carbon atoms, and combinations thereof;
R’，R”，R”’，R x ，R A ，R B each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclic group having 3 to 20 ring 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 alkene having 2 to 20 carbon atomsA group, a substituted or unsubstituted alkynyl 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 alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
"Tn" indicates the attachment position of said formula 2;
adjacent R', R x Optionally linked to form a ring;
adjacent R ', R', R A ，R B Can be optionally connected to form a ring.
2. The metal complex according to claim 1, wherein the ring Cy, at each occurrence, is selected from any one of the structures of the group consisting of:
wherein,
r represents, identically or differently on each occurrence, mono-, poly-or unsubstituted; when multiple R are present in any structure, the R are the same or different;
r is selected, identically or differently on each occurrence, 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 heterocyclic group having 3 to 20 ring 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 alkynyl 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 alkylgermyl having 3 to 20 carbon atoms, substituted or unsubstituted arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
adjacent substituents R can optionally be linked to form a ring;
wherein, "#" indicates a position to which the metal M is attached,
is represented by the formula X 1 ，X 2 ，X 3 Or X 4 The location of the connection.
3. The metal complex of claim 1, wherein the metal complex has M (L) a ) m (L b ) n (L c ) q A general formula (I);
wherein M is selected from the group consisting of Cu, ag, au, ru, rh, pd, os, ir, and Pt, the same or different at each occurrence; preferably, M is selected, identically or differently on each occurrence, from Pt or Ir;
L a 、L b and L c Are respectively a first, a second and a third ligand coordinated to the metal M, and L c And said L a Or L b Are the same or different; wherein L is a 、L b And L c Optionally linked to form a multidentate ligand;
m is selected from 1,2 or 3, n is selected from 0, 1 or 2, q is selected from 0, 1 or 2, M + n + q is equal to the oxidation state of metal M; when m is 2 or more, a plurality of L a The same or different; when n is equal toAt 2, two L b The same or different; when q is equal to 2, two L c The same or different;
L a each occurrence, the same or different, is selected from the group consisting of:
x is selected from the group consisting of O, S, se, NR ', siR ' R ' and GeR ' R '; when two R 'are present at the same time, the two R' are the same or different;
R，R x and R x1 The same or different at each occurrence denotes mono-, poly-or no-substitution;
R x1 has a structure shown in formula 2:
R A and R B The same or different at each occurrence indicates mono-, poly-or no-substitution;
ring a and ring B are selected, identically or differently, from carbocycles having 3-30 ring atoms, heterocycles having 3-30 ring atoms, or combinations thereof;
A 1 ，A 2 ，B 1 ，B 2 e, identically or differently at each occurrence, is selected from C, N, B, P, CR "', siR" ' or GeR "';
n is 0 or 1;
l is selected from single bond, O, S, SO 2 Se, NR ", CR" R ", siR" R ", geR" R ", BR", PR ", P (O) R", R "C = CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, an arylene group having 6-30 carbon atoms, a heteroarylene group having 3-30 carbon atoms, and combinations thereof;
"Tn" indicates the attachment position of said formula 2;
adjacent R', R x Optionally linked to form a ring;
adjacent R can be optionally connected to form a ring;
adjacent R ', R', R A ，R B Optionally linked to form a ring;
L b and L c A structure, which is the same or different at each occurrence, selected from any one of the group consisting of:
wherein,
X b each occurrence, the same or different, is selected from the group consisting of: o, S, se, NR N1 ，CR C1 R C2 ；
R a And R b The same or different at each occurrence indicates mono-, poly-, or no substitution;
adjacent substituents R a ，R b ，R c ，R N1 ，R C1 And R C2 Can optionally be linked to form a ring;
R’，R”，R”’，R，R x ，R A ，R B ，R a ，R b ，R c ，R N1 ，R C1 and R C2 Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring 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 alkynyl 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 arylgermyl having 6 to 20 carbon atoms, substituted or unsubstituted germanyl having 0 to 20 carbon atoms, substituted or unsubstituted amino, cyano, mercapto, and combinations thereof.
4. The metal complex of claim 1, wherein the metal complex has Ir (L) a ) m (L b ) 3-m And is represented by formula 3:
wherein,
m is selected from 1,2 or 3; when m is selected from 1, two of L b The same or different; when m is selected from 2 or 3, a plurality of L a The same or different;
x is selected from the group consisting of O, S, se, NR ', siR ' R ' and GeR ' R '; when two R 'are present at the same time, the two R' are the same or different;
Y 1 -Y 4 selected, identically or differently at each occurrence, from CR or N;
X 3 -X 8 selected from CR, identically or differently at each occurrence x ，CR x1 Or N;
X 3 -X 8 at least one of them is selected from CR x1 And R is x1 Has a structure shown in formula 2:
R A and R B The same or different at each occurrence denotes mono-, poly-or no-substitution;
ring a and ring B are selected, identically or differently, from carbocycles having 3 to 30 ring atoms, heterocycles having 3 to 30 ring atoms, or combinations thereof;
A 1 ，A 2 ，B 1 ，B 2 e, equal or different at each occurrence, is selected from C, N, B, P, CR "', siR" ' or GeR "';
n is 0 or 1;
l is selected from single bond, O, S, SO 2 Se, NR ", CR" R ", siR" R ", geR" R ", BR", PR ", P (O) R", R "C = CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, an arylene group having 6-30 carbon atoms, a heteroarylene group having 3-30 carbon atoms, and combinations thereof;
R’，R”，R”’，R，R x ，R A ，R B ，R 1 -R 8 each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocyclyl having 3 to 20 ring atoms, substituted or unsubstituted heterocyclyl having 7 to 30 carbon atomsA substituted or unsubstituted aralkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl 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 alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
adjacent R 1 -R 8 Can be optionally connected to form a ring;
adjacent R', R x Can be optionally connected to form a ring;
adjacent R can be optionally connected to form a ring;
adjacent R ', R', R A ，R B Can optionally be connected to form a ring.
5. A metal complex according to claim 4, wherein X 3 -X 8 Is selected, identically or differently on each occurrence, from CR x And CR x1 And/or Y 1 -Y 4 Each occurrence is selected, identically or differently, from CR.
6. A metal complex according to claim 4, wherein X is 3 -X 8 At least one of which is N, and/or Y 1 -Y 4 At least one of which is N.
7. The metal complex of any one of claims 1 to 6, X being selected from O or S.
8. Gold according to any one of claims 1 to 7A complex of formula (I), wherein R x Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted 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 alkylgermanyl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof;
preferably, R x Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 6 carbon atoms, a cyano group, and combinations thereof;
more preferably, R x Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, cyano, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclohexyl, phenyl, pyridyl, trimethylsilyl, trimethylgermyl, and combinations thereof.
9. A metal complex as claimed in any one of claims 1 to 8, wherein R x1 Has a structure represented by formula 4:
A 3 -A 6 selected from CR, identically or differently at each occurrence A Or N;
B 3 -B 6 selected from CR, identically or differently at each occurrence B Or N;
n is 0 or 1;
l is selected from single bond, O, S, SO 2 Se, NR ", CR" R ", siR" R ", geR" R ", BR", PR ", P (O) R", R "C = CR", a heteroalkylene group having 1-20 carbon atoms, a cycloalkylene group having 3-20 carbon atoms, a heterocyclylene group having 3-20 ring atoms, an arylene group having 6-30 carbon atoms, a heteroarylene group having 3-30 carbon atoms, and combinations thereof;
R A 、R B and R "is selected, identically or differently on each occurrence, from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylgermyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, a carbonyl group, an ester group, a cyano group, an isonicoyl group, a hydroxyl group, a mercapto group, a sulfonyl group, a mercapto group, and combinations thereof;
adjacent R', R A ，R B Optionally linked to form a ring;
"Tn" indicates the attachment position of said formula 4.
10. A metal complex according to claim 9, wherein a is 3 -A 6 Selected identically or differently at each occurrenceself-CR A And/or B 3 -B 6 Selected from CR, identically or differently at each occurrence B ；R A And R B Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted 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 alkylgermanyl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof;
preferably, R A And R B Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 6 carbon atoms, a cyano group, and combinations thereof;
more preferably, R A And R B At least one selected from the group consisting of: deuterium, fluorine, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms, a substituted or unsubstituted alkylgermyl group having 3 to 6 carbon atoms, a cyano group, and combinations thereof.
11. The metal complex of claim 1 or 9, wherein L is selected from the group consisting of a single bond, O, S, se, NR ", CR" R ", siR" R ", geR" R ", BR", PR ", P (O) R", R "C = CR", a heteroalkylene group having 1-10 carbon atoms, a cycloalkylene group having 3-10 carbon atoms, a heterocyclylene group having 3-10 ring atoms, an arylene group having 6-10 carbon atoms, a heteroarylene group having 3-10 carbon atoms, and combinations thereof;
preferably, L is selected from a single bond, O, S, NR ", R" C = CR ", phenylene;
more preferably, L is selected from single bonds.
12. A metal complex according to claim 1 or 4, wherein X 5 -X 8 At least one of which is selected from CR x1 ；
Preferably, X 7 Or X 8 At least one of which is selected from CR x1 ；
More preferably, X 8 Selected from the group consisting of CR x1 。
13. The metal complex of claim 1 or 4, wherein X 5 -X 8 At least one of them is selected from CR x And said R is x Selected from cyano or fluoro, X 5 -X 8 At least one further one of (A) is selected from CR x1 ；
Preferably, X 7 Selected from the group consisting of CR x Said R is x Is cyano or fluorine, X 8 Selected from the group consisting of CR x1 (ii) a And/or X 8 Selected from the group consisting of CR x Said R is x Is cyano or fluorine, X 7 Selected from the group consisting of CR x1 。
14. A metal complex according to claim 1, wherein R is x1 Is selected from An, identically or differently on each occurrence 1 To An 118 Group consisting of:
optionally, said An 1 To An 135 The hydrogen in (a) can be partially or fully substituted with deuterium.
15. The metal complex of any one of claims 1-14, wherein R, on each occurrence, is selected, identically or differently, from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 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 amino groups having 6 to 20 carbon atoms, and combinations thereof;
preferably, at least one R is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof.
16. A metal complex as claimed in claim 4, R 1 -R 8 Wherein at least one or at least two are selected from substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups of 3 to 20 ring carbon atoms, or combinations thereof, and all of said R' s 1 -R 4 And/or R 5 -R 8 The sum of the number of carbon atoms of (a) is at least 4;
R 1 -R 4 in which at least one or at least two groups selected from substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted orUnsubstituted cycloalkyl having 3 to 20 ring carbon atoms, or a combination thereof, and all of said R 1 -R 4 The sum of the number of carbon atoms of (a) is at least 4; and/or R 5 -R 8 Wherein at least one or at least two are selected from substituted or unsubstituted alkyl groups of 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups of 3 to 20 ring carbon atoms, or combinations thereof, and all of said R' s 5 -R 8 The sum of the number of carbon atoms of (a) is at least 4.
17. A metal complex according to claim 4, wherein R 2 ，R 3 ，R 6 ，R 7 At least one or at least two or at least three or all are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof;
preferably, R 2 ，R 3 ，R 6 ，R 7 At least one or at least two or at least three or all are selected from the group consisting of: deuterium, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof;
more preferably, R 2 ，R 3 ，R 6 ，R 7 At least one or at least two or at least three or all are selected from the group consisting of: methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, neopentyl, tert-pentyl, any of the foregoing radicals partially or fully deuterated, and deuterium.
18. A metal complex according to claim 1 or 14, wherein L a Each occurrence being selected identically or differently from L a1 To L a1832 Group of (I), L a1 To L a1832 The specific structure of (a) is as follows:
l is as follows a1 To L a1440 Has the following structure:
wherein X, cy, R X4 -R X8 An atom or group selected from the following table:
l is as follows a1441 To L a1514 Has the following structure:
wherein X, cy, R X4 -R X8 An atom or group selected from the following table:
l is as follows a1515 To L a1588 Has the advantages ofThe structure is as follows:
wherein X, cy, R X4 -R X8 An atom or group selected from the following table:
l is as follows a1589 To L a1662 Has the following structure:
wherein X, cy, R X4 -R X8 An atom or group selected from the following table:
l is as follows a1663 To L a1736 Has the following structure:
wherein X, cy, R X4 -R X8 An atom or group selected from the following table:
l is as follows a1737 To L a1760 Has the following structure:
wherein Cy, R X4 -R X7 An atom or group selected from the following table:
l is as follows a1761 To L a1784 Has the following structure:
wherein X, cy, R X4 -R X6 、R X8 An atom or group selected from the following table:
l is as follows a1785 To L a1808 Has the following structure:
wherein Cy and R X4 -R X5 、R X7 -R X8 An atom or group selected from the following table:
l is as follows a1809 To L a1832 Has the following structure:
wherein Cy and R X4 、R X6 -R X8 An atom or group selected from the following table:
in the above table, cy1 to Cy9 have the following structures:
in Cy1 to Cy9, "#" indicates linkage to the metal MIn the position of (a) or (b),
is represented by the formula X 1 ，X 2 ，X 3 Or X 4 The location of the connection;
TMS in the above table represents trimethylsilyl; TMG represents trimethylgermanium group;
optionally, said L a1 To L a1891 The hydrogen atoms in (a) can be partially or fully substituted by deuterium.
19. The metal complex of claim 1,4 or 18, wherein L b Each occurrence, the same or different, is selected from the group consisting of:
optionally, said L b1 To L b341 The hydrogen atoms in (a) can be partially or fully substituted by deuterium.
20. A metal complex according to claim 1 or 19, wherein L c Each occurrence, the same or different, is selected from the group consisting of:
21. the metal complex of claim 20, wherein the metal complex is selected from the group consisting of metal complex 1 through metal complex 1646;
wherein the metal complex 1 to the metal complex 1364 have IrL a (L b ) 2 Structure of (1), two L b Identical or different, L a And L b Respectively corresponding to the structures indicated in the following table:
wherein metal complex 1365 to metal complex 1382 have Ir (L) a ) 2 L b Structure of (2), two L a Identical or different, L a And L b Respectively corresponding to the structures indicated in the following table:
wherein metal complex 1383 to metal complex 1562 have Ir (L) a ) 2 L c Structure of (1), two L a Identical or different, L a And L c Respectively corresponding to the structures indicated in the following table:
wherein metal complexes 1563 to 1568 have Ir (L) a ) 3 Structure of (1), three L a Identical or different, three L a Respectively corresponding to the structures indicated in the following table:
of these, metal complexes 1569 to 1576 have Ir (L) a )(L b )(L c ) Structure of (1), L a 、L b And L c Respectively corresponding to the structures indicated in the following table:
wherein metal complex 1577 through metal complex 1646 have IrL a (L b ) 2 Structure of (1), two L b Same, L a And L b Respectively corresponding to the structures indicated in the following table:
optionally, the hydrogens in the above metal complex 1 through metal complex 1646 can be partially or fully substituted with deuterium.
22. An electroluminescent device, comprising:
an anode, a cathode, an anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, at least one of the organic layers comprising the metal complex of any one of claims 1-21.
23. The electroluminescent device of claim 22, wherein the organic layer comprising the metal complex is a light emitting layer.
24. The electroluminescent device of claim 23, wherein the light-emitting layer further comprises a first host compound;
preferably, the light-emitting layer further comprises a second host compound;
more preferably, at least one of the host compounds comprises at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.
25. The electroluminescent device of claim 24, wherein the metal complex is doped in the first host compound and the second host compound, and the weight of the metal complex is 1-30% of the total weight of the light-emitting layer;
preferably, the weight of the metal complex accounts for 3% -13% of the total weight of the light-emitting layer.
26. A composition comprising the metal complex of any one of claims 1-21.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17/889,980 US20230189629A1 (en) | 2021-08-20 | 2022-08-17 | Organic electroluminescent material and device thereof |
| JP2022131274A JP2023029324A (en) | 2021-08-20 | 2022-08-19 | Organic electroluminescent material and device thereof |
| EP22191270.2A EP4137551A1 (en) | 2021-08-20 | 2022-08-19 | Organic electroluminescent material and device thereof |
| KR1020220104888A KR20230028190A (en) | 2021-08-20 | 2022-08-22 | Organic electroluminescent material and device thereof |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2021109405041 | 2021-08-20 | ||
| CN202110940504 | 2021-08-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN115710290A true CN115710290A (en) | 2023-02-24 |
Family
ID=85230487
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210747647.5A Pending CN115710290A (en) | 2021-08-20 | 2022-06-29 | Organic electroluminescent material and device thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN115710290A (en) |
-
2022
- 2022-06-29 CN CN202210747647.5A patent/CN115710290A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN113816996A (en) | Phosphorescent organic metal complex and application thereof | |
| CN114907412A (en) | Organic electroluminescent material and device thereof | |
| CN114621199A (en) | Organic electroluminescent material and device thereof | |
| CN113816997B (en) | Phosphorescent organometallic complex and application thereof | |
| CN114605473A (en) | Phosphorescent organic metal complex and device thereof | |
| CN114621198A (en) | Organic electroluminescent material and device thereof | |
| CN115215906A (en) | Organic electroluminescent material and device thereof | |
| KR20220115780A (en) | Organic electroluminescent material and device thereof | |
| CN117624142A (en) | Organic electroluminescent material and device thereof | |
| CN113968873A (en) | Organic electroluminescent material and device thereof | |
| CN114516890B (en) | Organic electroluminescent material and device thereof | |
| CN109575085B (en) | Organic luminescent material containing tetra-ortho-phenylene ligand | |
| CN114181235B (en) | Polycyclic compound and device thereof | |
| CN115215905A (en) | Organic electroluminescent material and device thereof | |
| CN114256430A (en) | Electroluminescent device | |
| CN116836204A (en) | Organic electroluminescent material and device thereof | |
| CN118344350A (en) | Organic electroluminescent material and device thereof | |
| KR20230028190A (en) | Organic electroluminescent material and device thereof | |
| CN116813600A (en) | Organic electroluminescent material and device thereof | |
| CN114524850A (en) | Organic electroluminescent material and device thereof | |
| CN115403628A (en) | Organic electroluminescent material and device thereof | |
| CN115232170A (en) | Organic electroluminescent material and device thereof | |
| CN113735911A (en) | Metal complex, electroluminescent device and application thereof | |
| CN115710290A (en) | Organic electroluminescent material and device thereof | |
| CN115700256A (en) | Organic electroluminescent material and device thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |