CN117986238A - Organic electroluminescent material and device thereof - Google Patents
Organic electroluminescent material and device thereof Download PDFInfo
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- CN117986238A CN117986238A CN202211333457.5A CN202211333457A CN117986238A CN 117986238 A CN117986238 A CN 117986238A CN 202211333457 A CN202211333457 A CN 202211333457A CN 117986238 A CN117986238 A CN 117986238A
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- 239000000463 material Substances 0.000 title abstract description 72
- 150000001875 compounds Chemical class 0.000 claims abstract description 185
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 230000000903 blocking effect Effects 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 331
- -1 alkyl germanium Chemical compound 0.000 claims description 165
- 125000001424 substituent group Chemical group 0.000 claims description 113
- 239000010410 layer Substances 0.000 claims description 100
- 125000003118 aryl group Chemical group 0.000 claims description 67
- 125000001072 heteroaryl group Chemical group 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 32
- 229910052805 deuterium Inorganic materials 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 239000003446 ligand Substances 0.000 claims description 26
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 125000004104 aryloxy group Chemical group 0.000 claims description 21
- 239000012044 organic layer Substances 0.000 claims description 21
- 125000006413 ring segment Chemical group 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 17
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 229910052732 germanium Inorganic materials 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 13
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 12
- 125000005580 triphenylene group Chemical group 0.000 claims description 12
- 125000000732 arylene group Chemical group 0.000 claims description 11
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 10
- 229910052799 carbon 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
- 125000005549 heteroarylene group Chemical group 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 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
- UTUZBCDXWYMYGA-UHFFFAOYSA-N silafluorene Chemical compound C12=CC=CC=C2CC2=C1C=CC=[Si]2 UTUZBCDXWYMYGA-UHFFFAOYSA-N 0.000 claims description 7
- 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 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 6
- 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 6
- 229960005544 indolocarbazole Drugs 0.000 claims description 6
- 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
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 150000004696 coordination complex Chemical class 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000003636 chemical group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 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
- 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 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims description 2
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 2
- 150000002739 metals Chemical group 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 125000005551 pyridylene group Chemical group 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 39
- 230000015572 biosynthetic process Effects 0.000 description 32
- 238000003786 synthesis reaction Methods 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000007787 solid Substances 0.000 description 25
- 239000012043 crude product Substances 0.000 description 22
- 230000002829 reductive effect Effects 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000010438 heat treatment Methods 0.000 description 20
- 238000010992 reflux Methods 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- 239000008346 aqueous phase Substances 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 230000003111 delayed effect Effects 0.000 description 10
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 10
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 150000003384 small molecules Chemical class 0.000 description 7
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 238000005538 encapsulation Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
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- 230000000670 limiting effect Effects 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- 229910052796 boron Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000005104 aryl silyl group Chemical group 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 230000036961 partial effect Effects 0.000 description 3
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KOFLVDBWRHFSAB-UHFFFAOYSA-N 1,2,4,5-tetrahydro-1-(phenylmethyl)-5,9b(1',2')-benzeno-9bh-benz(g)indol-3(3ah)-one Chemical compound C1C(C=2C3=CC=CC=2)C2=CC=CC=C2C23C1C(=O)CN2CC1=CC=CC=C1 KOFLVDBWRHFSAB-UHFFFAOYSA-N 0.000 description 2
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical compound C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-UHFFFAOYSA-N 0.000 description 2
- 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
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([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
- 229920001621 AMOLED Polymers 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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-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
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-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
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-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
- 125000004429 atom Chemical group 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 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
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
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- 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
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 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
- 239000004033 plastic Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 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
- 230000002468 redox effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- DWRSCILTXDLQBG-UHFFFAOYSA-N silolane Chemical compound C1CC[SiH2]C1 DWRSCILTXDLQBG-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 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
- DBVXXBTUAZSUAY-UHFFFAOYSA-N tert-butyl(dimethyl)germanium Chemical group C[Ge](C)C(C)(C)C DBVXXBTUAZSUAY-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 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
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ZGYICYBLPGRURT-UHFFFAOYSA-N tri(propan-2-yl)silicon Chemical group CC(C)[Si](C(C)C)C(C)C ZGYICYBLPGRURT-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- UMRPCNGKANTZSN-UHFFFAOYSA-N tributylgermanium Chemical group CCCC[Ge](CCCC)CCCC UMRPCNGKANTZSN-UHFFFAOYSA-N 0.000 description 1
- ISEIIPDWJVGTQS-UHFFFAOYSA-N tributylsilicon Chemical group CCCC[Si](CCCC)CCCC ISEIIPDWJVGTQS-UHFFFAOYSA-N 0.000 description 1
- YMSWJBZPRYKQHJ-UHFFFAOYSA-N triethylgermanium Chemical group CC[Ge](CC)CC YMSWJBZPRYKQHJ-UHFFFAOYSA-N 0.000 description 1
- QXTIBZLKQPJVII-UHFFFAOYSA-N triethylsilicon Chemical group CC[Si](CC)CC QXTIBZLKQPJVII-UHFFFAOYSA-N 0.000 description 1
- WLKSSWJSFRCZKL-UHFFFAOYSA-N trimethylgermanium Chemical group C[Ge](C)C WLKSSWJSFRCZKL-UHFFFAOYSA-N 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
- VCQDQISTTHQOPS-UHFFFAOYSA-N tripropylgermanium Chemical group CCC[Ge](CCC)CCC VCQDQISTTHQOPS-UHFFFAOYSA-N 0.000 description 1
- MMYRBBZVCDXGHG-UHFFFAOYSA-N tripropylsilicon Chemical group CCC[Si](CCC)CCC MMYRBBZVCDXGHG-UHFFFAOYSA-N 0.000 description 1
- TYCHBGWSCCIDHZ-UHFFFAOYSA-N tritert-butylgermanium Chemical group CC(C)(C)[Ge](C(C)(C)C)C(C)(C)C TYCHBGWSCCIDHZ-UHFFFAOYSA-N 0.000 description 1
- STDLEZMOAXZZNH-UHFFFAOYSA-N tritert-butylsilicon Chemical group CC(C)(C)[Si](C(C)(C)C)C(C)(C)C STDLEZMOAXZZNH-UHFFFAOYSA-N 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
Classifications
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- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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Abstract
An organic electroluminescent material and a device thereof are disclosed. The organic electroluminescent material is a compound with a structure of formula 1, and the compound can be used as a main body material, an electron transport material, a hole blocking material or the like in an organic electroluminescent device, and can greatly improve the comprehensive performance of the device, such as high device efficiency, low driving voltage and/or greatly prolong the service life of the device. Also disclosed is a compound composition comprising the structure of formula 1.
Description
Technical Field
The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. And more particularly, to a compound having a structure of formula 1, and an organic electroluminescent device and a compound composition including the compound.
Background
Organic electronic devices include, but are not limited to, the following: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), organic Light Emitting Transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic electroluminescent devices.
In 1987, tang and Van Slyke of Isomangan reported a double-layered 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). Once biased into the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). Most advanced 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. Because OLEDs are self-emitting solid state devices, they offer great potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications, such as in flexible substrate fabrication.
OLEDs can be divided into three different types according to their light emission mechanism. The OLED of Tang and van Slyke invention is a fluorescent OLED. It uses only singlet light emission. The triplet states generated in the device are wasted through non-radiative decay channels. Thus, the Internal Quantum Efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation prevents commercialization of OLEDs. In 1997, forrest and Thompson reported phosphorescent OLEDs using triplet emission from heavy metals containing complexes as emitters. Thus, both singlet and triplet states can be harvested, achieving a 100% IQE. Because of its high efficiency, the discovery and development of phosphorescent OLEDs has contributed directly to the commercialization of Active Matrix OLEDs (AMOLEDs). Recently, adachi achieved high efficiency by Thermally Activated Delayed Fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons by reverse intersystem crossing, resulting in high IQE.
OLEDs can also be classified into small molecule and polymeric OLEDs depending on the form of the materials used. Small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of the small molecules can be large as long as they have a precise structure. Dendrimers with a defined structure are considered small molecules. Polymeric OLEDs include conjugated polymers and non-conjugated polymers having pendant luminescent groups. Small molecule OLEDs can become polymeric OLEDs if post-polymerization occurs during fabrication.
Various methods of OLED fabrication exist. Small molecule OLEDs are typically fabricated by vacuum thermal evaporation. Polymeric OLEDs are manufactured by solution processes such as spin coating, inkjet printing and nozzle printing. Small molecule OLEDs can also be fabricated by solution processes if the material can be dissolved or dispersed in a solvent.
The emission color of an OLED can be achieved by the structural design of the luminescent material. The OLED may include a light emitting layer or layers to achieve a desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems of blue unsaturation, short device lifetime, high operating voltage, and the like. Commercial full color OLED displays typically employ a mixing strategy using blue fluorescent and phosphorescent yellow, or red and green. Currently, a rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. In addition, it is desirable to have a more saturated emission spectrum, higher efficiency and longer device lifetime. Triazine organic semiconductor materials are widely used in OLEDs because of their excellent photoelectric properties, redox properties, stability, and the like.
US20190214570A1 discloses an organic compound having the following formula and an organic light-emitting device comprising the compound: Wherein Ar 1 is selected from/> Ar 2 is selected from/> Wherein E 1 is selected from C (R 21)(R22),Si(R23)(R24),N(R25), O, or S. The specific compounds disclosed in this application relate to the structures Ar 1 and Ar 2 wherein E 1 is selected from N (R 25) and wherein each specific compound comprises at least two carbazole groups. Furthermore, this application discloses the following specific compounds containing fluorenyl groups: /(I)But the compound also contains two carbazole groups, and the triazine fragment is connected with the 2-position of fluorene through phenylene. Thus, the application is directed to compounds in which the triazine is linked to a plurality of carbazole fragments, and does not focus on compounds in which the triazine is linked to a fluorenyl fragment (or via a linker), and does not teach compounds in which the triazine is linked to a fluorenyl group at a specific position (or via a linker).
WO2021040467A1 discloses organic compounds having the following formula and organic light-emitting devices comprising said compounds: Wherein Ar is a substituted or unsubstituted aryl group of C 6-60. The application discloses in specific structures the following compounds: /(I) The compounds disclosed in this application must have at least two carbazolyl groups on the triazine-linked phenylene group, and do not disclose or teach compounds having only one carbazolyl group on the triazine-linked phenylene group and their use in organic electroluminescent devices.
WO2020262861A1 discloses organic compounds having the following formula and organic light-emitting devices comprising said compounds: Wherein L is attached to carbon number 1, carbon number 2 or carbon number 3, L is a single bond, or a substituted or unsubstituted C 6-60 arylene group; ar 1 and Ar 2 are each independently substituted or unsubstituted C 6-60 aryl, or substituted or unsubstituted C 2-60 heteroaryl comprising any one or more selected from N, O and S; r 2 is each independently selected from substituted or unsubstituted aryl, benzoxazolyl, benzothiazolyl, dibenzofuranyl or phenyl substituted benzothiazolyl of C 6-60; q is an integer of 1 to 8. The application discloses the following compounds in specific structure Etc., there is no disclosure of any fluorene/silafluorene containing compound. The application therefore does not disclose or teach compounds in which triazine moieties are attached to fluorene/silafluorene, and does not teach compounds in which triazines are attached (or via a linker) to fluorene/silafluorene at specific positions.
However, the triazine organic semiconductor materials reported at present have certain limitations on the carrier transmission capability and service life of the photoelectric device. Therefore, the application potential of the material is worth continuing to be deeply researched and developed.
Disclosure of Invention
The present invention aims to provide a series of compounds having the structure of formula 1 to solve at least part of the above problems. The compound can be applied to an organic electroluminescent device, and can greatly improve the comprehensive performance of the device, such as high device efficiency, low driving voltage and/or greatly prolong the service life of the device.
According to one embodiment of the present invention, a compound having the structure of formula 1 is disclosed:
In the formula (1) of the present invention,
One of X 1 and X 2 is selected from C, and the other is selected from CR x or N;
y 1 and Y 2 are, identically or differently, selected for each occurrence from CR y or N;
z 1-Z5 is selected identically or differently on each occurrence from CR z or N;
U 1-U4 is selected identically or differently on each occurrence from CR u or N;
V 1-V4 is selected identically or differently on each occurrence from CR v or N;
E is selected identically or differently on each occurrence from CRR or SiRR;
One of E 1,E3 and E 4 is selected from C and is linked to L in formula 1, and the remaining two are selected, identically or differently, from CR e or N at each occurrence;
E 2 and E 5-E8 are selected identically or differently on each occurrence from CR e or N;
Ar is selected, identically or differently, for each occurrence, from a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, or a combination thereof;
l is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
R x,Rz,Ru,Rv,Re and R are 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 heteroaryl having 3 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 alkyl 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 atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
R y 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 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 alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium having 6 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 6 to 20 carbon atoms, carbonyl, isocyanate, sulfonyl, and combinations thereof;
Adjacent substituents R y can optionally be linked to form a ring; adjacent substituents R z can optionally be linked to form a ring; adjacent substituents R u can optionally be linked to form a ring; adjacent substituents R v can optionally be linked to form a ring; adjacent substituents R e can optionally be linked to form a ring; adjacent substituents R can optionally be joined to form a ring.
According to another embodiment of the present invention, there is also disclosed an electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, the organic layer comprising the compound of formula 1 according to the previous embodiment.
According to another embodiment of the present invention, there is also disclosed a compound composition comprising the compound of formula 1 as described in the previous embodiment.
The invention discloses a series of compounds with a structure shown in a formula 1. The compound can be used as a main body material, an electron transport material or a hole blocking material in an organic electroluminescent device, and the like, and can greatly improve the comprehensive performance of the device, such as high device efficiency, low driving voltage and/or greatly prolong the service life of the device.
Drawings
Fig. 1 is a schematic diagram of an organic light emitting device that may contain the compounds and compound compositions disclosed herein.
Fig. 2 is a schematic view of another organic light emitting device that may contain the compounds and compound compositions disclosed herein.
Detailed Description
OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically illustrates, without limitation, an organic light-emitting device 100. The drawings are not necessarily to scale, and some of the layer structures in the drawings may be omitted as desired. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 may be fabricated by sequentially depositing the layers described. The nature and function of the various layers and exemplary materials are described in more detail in U.S. patent US7,279,704B2 at columns 6-10, the entire contents of which are incorporated herein by reference.
There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F 4 -TCNQ at a molar ratio of 50:1, as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. Pat. No. 6,303,238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li in a molar ratio of 1:1 as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of cathodes are disclosed in U.S. Pat. nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, including composite cathodes having a thin layer of metal, such as Mg: ag, with an overlying transparent, electrically conductive, sputter deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. patent No. 6,097,147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of implant layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.
The above-described hierarchical structure is provided by way of non-limiting example. The function of the OLED may be achieved by combining the various layers described above, or some of the layers may be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of materials may be used to achieve optimal performance. Any functional layer may comprise several sublayers. For example, the light emitting layer may have two layers of different light emitting materials to achieve a desired light emission spectrum.
In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.
The OLED also requires an encapsulation layer, such as the organic light emitting device 200 shown schematically and without limitation in fig. 2, which differs from fig. 1 in that an encapsulation layer 102 may also be included over the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function may be used as the encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film packages are described in U.S. patent US7,968,146B2, the entire contents of which are incorporated herein by reference.
Devices manufactured according to embodiments of the present invention may be incorporated into a variety of consumer products having one or more electronic component modules (or units) of the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and/or signaling, heads-up displays, displays that are fully or partially transparent, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptops, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and taillights.
The materials and structures described herein may also be used in other organic electronic devices as listed above.
As used herein, "top" means furthest from the substrate and "bottom" means closest to the substrate. In the case where the first layer is described as being "disposed" on "the second layer, the first layer is disposed farther from the substrate. Unless a first layer is "in contact with" a second layer, other layers may be present between the first and second layers. For example, a cathode may be described as "disposed on" an anode even though various organic layers are present between the cathode and the anode.
As used herein, "solution processable" means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium in the form of a solution or suspension.
A ligand may be referred to as "photosensitive" when it is believed that the ligand directly contributes to the photosensitive properties of the emissive material. When it is believed that the ligand does not contribute to the photosensitive properties of the emissive material, the ligand may be referred to as "ancillary," but ancillary ligands may alter the properties of the photosensitive ligand.
It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by spin statistics that delay fluorescence by more than 25%. Delayed fluorescence can be generally classified into two types, i.e., P-type delayed fluorescence and E-type delayed fluorescence. The P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).
On the other hand, the E-type delayed fluorescence does not depend on the collision of two triplet states, but on the transition between the triplet states and the singlet excited state. Compounds capable of generating E-type delayed fluorescence need to have very small mono-triplet gaps in order for the conversion between the energy states. The thermal energy may activate a transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as Thermally Activated Delayed Fluorescence (TADF). A significant feature of TADF is that the delay component increases with increasing temperature. The fraction of backfill singlet excited states may reach 75% if the reverse intersystem crossing (RISC) rate is fast enough to minimize non-radiative decay from the triplet states. The total singlet fraction may be 100%, well in excess of 25% of the spin statistics of the electrically generated excitons.
Type E delayed fluorescence features can be found in excitation complex systems or in single compounds. Without being bound by theory, it is believed that E-delayed fluorescence requires a luminescent material with a small mono-triplet energy gap (Δe S-T). Organic non-metal containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is typically characterized as donor-acceptor Charge Transfer (CT) type emission. The spatial separation of HOMO from LUMO in these donor-acceptor compounds generally yields a small Δe S-T. These states may include CT states. Typically, donor-acceptor luminescent materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) to an electron acceptor moiety (e.g., an N-containing six-membered aromatic ring).
Definition of terms for substituents
Halogen or halide-as used herein, includes fluorine, chlorine, bromine and iodine.
Alkyl-as used herein, includes 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. Cycloalkyl groups may be cycloalkyl groups having 3 to 20 ring carbon atoms, preferably 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, a heteroalkyl comprises an alkyl chain in which one or more carbons is replaced by a heteroatom selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron. The heteroalkyl group may be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermylmethyl, trimethylgermylethyl, dimethylethylgermylmethyl, dimethylisopropylgermylmethyl, t-butyldimethylgermylmethyl, triethylgermylmethyl, triethylgermylethyl, triisopropylgermylmethyl, triisopropylgermylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl. In addition, heteroalkyl groups may be optionally substituted.
Alkenyl-as used herein, covers straight chain, branched chain, and cyclic alkylene groups. Alkenyl groups may be alkenyl groups containing 2 to 20 carbon atoms, preferably alkenyl groups having 2 to 10 carbon atoms. Examples of alkenyl groups include ethenyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, 1-methylvinyl, styryl, 2-diphenylvinyl, 1-methallyl, 1-dimethylallyl, 2-methallyl, 1-phenylallyl, 2-phenylallyl, 3-diphenylallyl, 1, 2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cycloheptatrienyl, cyclooctenyl, cyclooctatetraenyl and norbornenyl. In addition, alkenyl groups may be optionally substituted.
Alkynyl-as used herein, straight chain alkynyl is 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 groups 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 the aryl group 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-condensed 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 '-methylbiphenyl-4' -tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesityl and m-tetrabiphenyl. In addition, aryl groups may be optionally substituted.
Heterocyclyl or heterocycle-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 and an unsaturated non-aromatic heterocyclic group having 3 to 20 ring atoms, at least one of which is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms including at least one hetero atom such as nitrogen, oxygen, silicon or sulfur. Examples of non-aromatic heterocyclic groups include oxiranyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxacycloheptatrienyl, thietaneyl, azepanyl and tetrahydrosilol. 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 nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms, and boron atoms. 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, oxazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indenoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furodipyridine, benzothiophene, thienodipyridine, benzoselenophene, selenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-aza-boron, 1, 3-aza-boron, 1-aza-boron-4-aza, boron-doped compounds, and the like. 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 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 alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, the alkoxy group 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 aryloxy groups include phenoxy and biphenoxy. In addition, the aryloxy group may be optionally substituted.
Aralkyl-as used herein, encompasses aryl-substituted alkyl. 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 aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α -naphthylmethyl, 1- α -naphthyl-ethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthyl-ethyl, 2- β -naphthyl-ethyl, 1- β -naphthylisopropyl, 2- β -naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, cyano, o-cyanobenzyl, o-chlorobenzyl, 1-chlorophenyl and 1-isopropyl. Among the above, preferred are benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl. In addition, aralkyl groups may be optionally substituted.
Alkyl-as used herein, alkyl-substituted silicon groups are contemplated. The silyl group may be a silyl group having 3 to 20 carbon atoms, preferably a silyl group having 3 to 10 carbon atoms. Examples of the alkyl silicon group include trimethyl silicon group, triethyl silicon group, methyldiethyl silicon group, ethyldimethyl silicon group, tripropyl silicon group, tributyl silicon group, triisopropyl silicon group, methyldiisopropyl silicon group, dimethylisopropyl silicon group, tri-t-butyl silicon group, triisobutyl silicon group, dimethyl-t-butyl silicon group, and methyldi-t-butyl silicon group. In addition, the alkyl silicon group may be optionally substituted.
Arylsilane-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 arylsilyl groups include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenyl silyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, diphenyltert-butylsilyl. In addition, arylsilane groups may be optionally substituted.
Alkyl germanium group-as used herein, alkyl substituted germanium groups are contemplated. The alkylgermanium group may be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkyl germanium groups include trimethyl germanium group, triethyl germanium group, methyl diethyl germanium group, ethyl dimethyl germanium group, tripropyl germanium group, tributyl germanium group, triisopropyl germanium group, methyl diisopropyl germanium group, dimethyl isopropyl germanium group, tri-t-butyl germanium group, triisobutyl germanium group, dimethyl-t-butyl germanium group, methyl-di-t-butyl germanium group. In addition, alkyl germanium groups may be optionally substituted.
Arylgermanium group-as used herein, encompasses at least one aryl or heteroaryl substituted germanium group. The arylgermanium group may be an arylgermanium group having 6-30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of aryl germanium groups include triphenylgermanium group, phenylbiphenyl germanium group, diphenylbiphenyl germanium group, phenyldiethyl germanium group, diphenylethyl germanium group, phenyldimethyl germanium group, diphenylmethyl germanium group, phenyldiisopropylgermanium group, diphenylisopropylgermanium group, diphenylbutylgermanium group, diphenylisobutylglycol group, and diphenyltert-butylgermanium group. In addition, the arylgermanium group may be optionally substituted.
The term "aza" in azadibenzofurans, azadibenzothiophenes and the like means that one or more C-H groups in the corresponding aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylenes include dibenzo [ f, h ] quinoxalines, dibenzo [ f, h ] quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-described aza derivatives will be readily apparent to those of ordinary skill in the art, and all such analogs are intended to be included in the terms described herein.
In the present disclosure, when any one of the terms from the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanium, substituted arylgermanium, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, alkyl, cycloalkyl, heteroalkyl, heterocyclyl, aralkyl, alkoxy, aryloxy, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino groups, which may be substituted with one or more groups selected from the group consisting of deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted cycloalkyl having 1 to 20 carbon atoms, unsubstituted alkenyl having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted alkenyl having 3 to 30 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted alkenyl having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 30 carbon atoms, unsubstituted aryl having 3 to 20 carbon atoms, unsubstituted aryl having 3 to 30 carbon atoms, unsubstituted alkylgermanium groups having 3 to 20 carbon atoms, unsubstituted arylgermanium 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, hydroxyl groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphine groups, and combinations thereof.
It will be appreciated that when a fragment of a molecule is described as a substituent or otherwise attached to another moiety, its name may be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or linking fragments are considered equivalent.
In the compounds mentioned in this disclosure, the hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. Substitution of other stable isotopes in the compounds may be preferred because of their enhanced efficiency and stability of the device.
In the compounds mentioned in this disclosure, polysubstituted means inclusive of disubstituted up to the maximum available substitution range. When a substituent in a compound mentioned in this disclosure means multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), it means that the substituent may be present at a plurality of available substitution positions on its linking structure, and the substituent present at each of the plurality of available substitution positions may be of the same structure or of different structures.
In the compounds mentioned in this disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless explicitly defined, for example, adjacent substituents can optionally be linked to form a ring. In the compounds mentioned in this disclosure, adjacent substituents can optionally be linked to form a ring, both in the case where adjacent substituents can be linked to form a ring and in the case where adjacent substituents are not linked to form a ring. Where 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. In this expression, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to further distant carbon atoms. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.
The expression that adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
The expression that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
the expression that adjacent substituents can optionally be linked to form a ring is also intended to be taken to mean that the two substituents bound to further distant carbon atoms are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
furthermore, the expression that adjacent substituents can optionally be 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 formula:
according to one embodiment of the present invention, a compound having the structure of formula 1 is disclosed:
In the formula (1) of the present invention,
One of X 1 and X 2 is selected from C, and the other is selected from CR x or N;
y 1 and Y 2 are, identically or differently, selected for each occurrence from CR y or N;
z 1-Z5 is selected identically or differently on each occurrence from CR z or N;
U 1-U4 is selected identically or differently on each occurrence from CR u or N;
V 1-V4 is selected identically or differently on each occurrence from CR v or N;
E is selected identically or differently on each occurrence from CRR or SiRR;
One of E 1,E3 and E 4 is selected from C and is linked to L in formula 1, and the remaining two are selected, identically or differently, from CR e or N at each occurrence;
E 2 and E 5-E8 are selected identically or differently on each occurrence from CR e or N;
Ar is selected, identically or differently, for each occurrence, from a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, or a combination thereof;
l is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
R x,Rz,Ru,Rv,Re and R are 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 heteroaryl having 3 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 alkyl 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 atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
R y 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 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 alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium having 6 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 6 to 20 carbon atoms, carbonyl, isocyanate, sulfonyl, and combinations thereof;
Adjacent substituents R y can optionally be linked to form a ring; adjacent substituents R z can optionally be linked to form a ring; adjacent substituents R u can optionally be linked to form a ring; adjacent substituents R v can optionally be linked to form a ring; adjacent substituents R e can optionally be linked to form a ring; adjacent substituents R can optionally be joined to form a ring.
Herein, "one of X 1 and X 2 is selected from C, the other is selected from CR x or N" is intended to mean one of X 1 and X 2 is selected from C, and is structurally related to the structureThe other is selected from CR x or N. There are two cases: when X 1 is selected from C, it is related to structure/>To (wherein ":" represents the position of attachment of the structure to X 1), then X 2 is selected from CR x or N; when X 2 is selected from C, it is related to structure/>And X 1 is selected from CR x or N.
Herein, "adjacent substituents R y can optionally be linked to form a ring" is intended to mean that any two of the adjacent substituents R y can be linked to form a ring. Obviously, any adjacent R y may not be connected to form a ring.
Herein, "adjacent substituents R z can optionally be linked to form a ring" is intended to mean that any two of the adjacent substituents R z can be linked to form a ring. Obviously, any adjacent R z may not be connected to form a ring.
Herein, "adjacent substituents R u can optionally be linked to form a ring" is intended to mean that any two of the adjacent substituents R u can be linked to form a ring. Obviously, any adjacent R u may not be connected to form a ring.
Herein, "adjacent substituents R v can optionally be linked to form a ring" is intended to mean that any two of the adjacent substituents R v can be linked to form a ring. Obviously, any adjacent R v may not be connected to form a ring.
Herein, "adjacent substituents R e can optionally be linked to form a ring" is intended to mean that any two of the adjacent substituents R e can be linked to form a ring. Obviously, any adjacent R e may not be connected to form a ring.
Herein, "adjacent substituents R can optionally be linked to form a ring" is intended to mean that any two of the adjacent substituents R can be linked to form a ring. Obviously, any adjacent R may not be connected to form a ring.
According to one embodiment of the present invention, the adjacent substituents R y and R z in the compound of formula 1 are not linked to form a ring.
According to one embodiment of the present invention, the compound of formula 1 contains only one carbazole structure or an azacarbazole structure or a carbazole condensed ring structure or an azacarbazole condensed ring structure. The carbazole structure or the azacarbazole structure or the carbazole condensed ring structure or the azacarbazole condensed ring structure has been shown in the structure of formula 1, i.e., includes the condensed ring structure where U 1-U4 and V 1-V4 are located.
According to one embodiment of the invention, wherein said E is selected from CRR.
According to one embodiment of the invention, wherein said 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 alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.
According to one embodiment of the invention, wherein said R is chosen identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted neopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and combinations thereof.
According to one embodiment of the present invention, wherein one of X 1 and X 2 is selected from C, and is structurally related toThe other is selected from CR x.
According to one embodiment of the invention, wherein said Y 1 and Y 2 are chosen identically or differently for each occurrence from CR y.
According to one embodiment of the invention, wherein said Z 1-Z5 is selected identically or differently on each occurrence from CR z.
According to one embodiment of the invention, wherein said U 1-U4 is selected identically or differently on each occurrence from CR u.
According to one embodiment of the invention, wherein said V 1-V4 is selected identically or differently on each occurrence from CR v.
According to one embodiment of the invention, wherein one of E 1,E3 and E 4 is selected from C and is linked to L in formula 1, the remaining two are selected from CR e,E2 and E 5-E8, identically or differently, at each occurrence, from CR e.
According to one embodiment of the invention, wherein E 3 is selected from C and is linked to L in formula 1, E 1 and E 4 are selected from CR e.
According to one embodiment of the invention, wherein E 4 is selected from C and is linked to L in formula 1, E 1 and E 3 are selected from CR e.
According to one embodiment of the invention, wherein Ar is selected, identically or differently, for each occurrence, from a substituted or unsubstituted aryl group having from 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 20 carbon atoms, or a combination thereof.
According to one embodiment of the invention, wherein said Ar is selected, identically or differently, at each occurrence, from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and combinations thereof.
According to one embodiment of the invention, wherein said L is, identically or differently, selected from a single bond, 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.
According to one embodiment of the present invention, wherein the L is selected, identically or differently, for each occurrence, from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted pyridylene group, or a combination thereof.
According to one embodiment of the invention, wherein said L is chosen, identically or differently, for each occurrence, from a single bond, or a substituted or unsubstituted phenylene group.
According to one embodiment of the invention, wherein each occurrence of said R x,Rz,Ru,Rv and R e is identically or differently 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 alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof.
According to one embodiment of the invention, wherein each occurrence of said R x,Rz,Ru,Rv and R e is the same or different selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and combinations thereof.
According to one embodiment of the invention, wherein said R y 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 alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, cyano groups, and combinations thereof.
According to one embodiment of the invention, wherein said R y is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, and combinations thereof.
According to an embodiment of the invention, wherein the compound is selected from the group consisting of compound a-1 to compound a-460, the specific structure of the compound a-1 to compound a-460 is given in claim 9.
According to one embodiment of the invention, the hydrogen energy in the compounds a-1 to a-460 is partially or fully substituted by deuterium.
According to an embodiment of the present invention, there is also disclosed an organic electroluminescent device including:
an anode is provided with a cathode,
A cathode electrode, which is arranged on the surface of the cathode,
And an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having a structure of formula 1, the compound having a structure of formula 1 being any one of the embodiments described above.
According to one embodiment of the invention, wherein the organic layer is a light emitting layer and the compound is a host compound.
According to one embodiment of the invention, wherein the organic layer is an electron transporting layer and the compound is an electron transporting compound.
According to one embodiment of the invention, wherein the organic layer is a hole blocking layer and the compound is a hole blocking compound.
According to one embodiment of the invention, wherein the organic layer is a light-emitting layer, and the compound is a host compound; the light emitting layer comprises a first metal complex having the general formula of M (L a)m(Lb)n(Lc)q;
the metal M is selected from metals with relative atomic mass of more than 40;
L a、Lb、Lc is a first ligand, a second ligand and a third ligand, respectively, which are coordinated to the metal M, and the ligands L a、Lb、Lc may be the same or different;
Ligand L a、Lb、Lc can optionally be linked to form a multidentate ligand;
m is 1, 2 or 3; n is 0, 1 or 2; q is 0, 1 or 2; the sum of M, n, q is equal to the oxidation state of the metal M; when m is 2 or more, the plurality of L a may be the same or different; when n is 2, two L b may be the same or different; when q is 2, two L c may be the same or different;
ligand L a has a structure as shown in formula 2:
Ring C 1 and ring C 2 are, identically or differently, selected from aromatic rings having 5 to 30 ring atoms, heteroaromatic rings having 5 to 30 ring atoms, or combinations thereof;
Q 1 and Q 2 are selected identically or differently on each occurrence from C or N;
Each occurrence of A 1 and A 2 is identically or differently selected from single bonds, O or S;
L 1 is selected identically or differently on each occurrence from the group consisting of: a single bond, BR ', CR ' R ', NR ', O, siR ' R ', PR ', S, geR ' R ', se, a substituted or unsubstituted vinylidene group, an ethynylene group, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms, and combinations thereof; when two R's are present at the same time, the two R's are the same or different;
R 11 and R 12, which are identical or different for each occurrence, represent mono-substituted, polysubstituted or unsubstituted;
R', R 11 and R 12 are 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 heteroaryl having 3 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 alkyl 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 atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
adjacent substituents R', R 11 and R 12 can optionally be linked to form a ring;
The ligands L b and L c are, identically or differently, selected from monoanionic bidentate ligands at each occurrence.
In this embodiment, "adjacent substituents R ', R 11, and R 12 can optionally be joined to form a ring" is intended to mean wherein any one or more of the groups of substituents can be joined to form a ring, for example, between adjacent substituents R', between adjacent substituents R 11, between adjacent substituents R 12, and between adjacent substituents R 11 and R 12. Obviously, these substituents may not all be linked to form a ring.
According to one embodiment of the invention, the ligands L b and L c are, for each occurrence, identically or differently selected from the group consisting of the following structures:
Wherein,
R a and R b, which are identical or different at each occurrence, represent monosubstituted, polysubstituted or unsubstituted;
X b is selected identically or differently on each occurrence from the group consisting of: o, S, se, NR N1 and CR C1RC2;
X c and X d are selected identically or differently on each occurrence from the group consisting of: o, S, se and NR N2;
R a,Rb,Rc,RN1,RN2,RC1 and R C2 are 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 heteroaryl having 3 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 alkyl 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 atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
Adjacent substituents R a,Rb,Rc,RN1,RN2,RC1 and R C2 can optionally be linked to form a ring.
In this embodiment, adjacent substituents R a,Rb,Rc,RN1,RN2,RC1 and R C2 can optionally be joined to form a ring, which is intended to mean groups of substituents wherein adjacent substituents, for example, between two substituents R a, between two substituents R b, between two substituents R c, between substituents R a and R b, between substituents R a and R c, between substituents R b and R c, between substituents R a and R N1, between substituents R b and R N1, between substituents R a and R C1, between substituents R a and R C2, between substituents R b and R C1, between substituents R b and R C2, between substituents R a and R N2, between substituents R b and R N2, and between R C1 and R C2, any one or more of these groups of substituents can be joined to form a ring. For example, the number of the cells to be processed,Optionally, adjacent substituents R a,Rb can be joined to form a ring, which can form one or more of the following structures including, but not limited to:
Wherein W is selected from O, S, se, NR w or CR wRw; wherein the definition of R w,Ra',Rb' is the same as R a. Obviously, these substituents may not all be linked to form a ring.
According to one embodiment of the present invention, wherein the first metal complex has the general structure of Ir (L a)m(Lb)3-m, and the structure represented by formula 2-1:
Wherein,
M is 0, 1,2 or 3; when m is 2 or 3, a plurality of L a are the same or different; when m is 0 or 1, a plurality of L b are the same or different;
T 1-T6 is selected identically or differently from CR T or N;
R a、Rb and R d, which are identical or different at each occurrence, represent monosubstituted, polysubstituted or unsubstituted;
R a、Rb、Rd and R T are 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 heteroaryl having 3 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 alkyl 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 atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
adjacent substituents R a,Rb can optionally be linked to form a ring;
adjacent substituents R d,RT can optionally be linked to form a ring.
In this embodiment, "adjacent substituents R a,Rb can optionally be linked to form a ring" is intended to mean wherein adjacent groups of substituents, for example, between two substituents R a, between two substituents R b, and between substituents R a and R b, any one or more of which may be linked to form a ring. Obviously, these substituents may not all be linked to form a ring.
In this embodiment, "adjacent substituents R d,RT can optionally be linked to form a ring" is intended to mean wherein adjacent groups of substituents, for example, between two substituents R T, between two substituents R d, any one or more of these groups of substituents can be linked to form a ring. Obviously, these substituents may not all be linked to form a ring.
According to one embodiment of the invention, wherein at least one of T 1-T6 is selected from CR T and R T is selected from substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, or substituted or unsubstituted heteroaryl having 3-30 carbon atoms.
According to one embodiment of the invention, wherein at least one of T 1-T6 is selected from CR T and R T is selected from fluorine or cyano.
According to one embodiment of the invention, wherein at least two of T 1-T6 are selected from CR T and wherein one R T is selected from fluorine or cyano and the other R T is selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, or substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms.
According to one embodiment of the invention, the T 1-T6 is selected identically or differently from CR T for each occurrence.
According to one embodiment of the invention, wherein T 1-T6 is selected identically or differently on each occurrence from CR T or N, and at least one of T 1-T6 is selected from N, for example one or two of T 1-T6 are selected from N.
According to an embodiment of the present invention, wherein the first metal complex is selected from the group consisting of compounds GD1 to GD76, the specific structure of compounds GD1 to GD76 is as defined in claim 13.
According to one embodiment of the invention, the hydrogen energy in the compounds GD 1-GD 76 is partially or fully replaced by deuterium.
According to one embodiment of the invention, wherein the organic layer is a light emitting layer, the compound is a host compound, and a second host compound is further included in the light emitting layer, the second host compound including 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 second host compound comprises at least one chemical group selected from the group consisting of: benzene, carbazole, indolocarbazole, fluorene, silafluorene, and combinations thereof.
According to one embodiment of the invention, wherein the second host compound has a structure represented by formula 3 or formula 4:
Wherein,
G is selected identically or differently for each occurrence from C (R g)2、NRg, O or S;
L T is selected, identically or differently, 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;
t is selected identically or differently on each occurrence from C, CR t or N;
R t,Rg 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 heteroaryl having 3 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 alkyl 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 atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
Ar 1 and Ar 2 are, identically or differently, selected from the group consisting of 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;
Adjacent substituents R t、Rg can optionally be linked to form a ring.
Herein, "adjacent substituents R t、Rg can optionally be linked to form a ring" is intended to mean wherein adjacent groups of substituents, for example, between two substituents R t, between two substituents R g, between substituents R t and R g, any one or more of which may be linked to form a ring. Obviously, none of these substituents may be linked to form a ring.
According to one embodiment of the present invention, wherein the second host compound has a structure represented by one of formulas 3-a to 3-j, formula 4-a to 4-f:
/>
Wherein,
L T is selected, identically or differently, 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;
t is selected identically or differently on each occurrence from CR t or N;
G is selected identically or differently for each occurrence from C (R g)2、NRg, O or S;
Ar 1、Ar2 is selected, identically or differently, on each occurrence, from a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, or a combination thereof;
r t、Rg is selected identically or differently on each occurrence from the group consisting of: r t,Rg 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 heteroaryl having 3 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 alkyl 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 atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
Adjacent substituents R t and R g can optionally be linked to form a ring.
According to one embodiment of the invention, wherein, in formulae 3-a to 3-j, formulae 4-a to 4-f, T is selected identically or differently for each occurrence from CR t.
According to one embodiment of the invention, wherein in formulae 3-a to 3-j, formulae 4-a to 4-f, T is selected identically or differently for each occurrence from CR t or N, and wherein at least one T is selected from N, for example one T or two T are selected from N.
According to an embodiment of the invention, the second host compound is selected from the group consisting of compounds PH-1 to PH-50, the specific structure of which compounds PH-1 to PH-50 is given in claim 16.
According to one embodiment of the invention, the organic electroluminescent device emits green light.
According to one embodiment of the invention, the organic electroluminescent device emits white light.
According to an embodiment of the present invention, there is also disclosed a compound composition comprising a compound represented by formula 1; the compounds are shown in any of the previous examples.
Combined with other materials
The materials described herein for specific layers in an organic light emitting device may be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. patent application 2016/0359122A1, paragraphs 0132-0161, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
Materials described herein as useful for specific layers in an organic light emitting device may be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein may be used in combination with a variety of light-emitting dopants, hosts, transport layers, barrier layers, implant layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application Ser. No. 2015/0349273A1, paragraphs 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that may be used in combination with the 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 protection, unless otherwise indicated. All reaction solvents were anhydrous and used as received from commercial sources. The synthetic products were subjected to structural confirmation and characterization testing using one or more equipment conventional in the art (including, but not limited to, bruker's nuclear magnetic resonance apparatus, shimadzu's liquid chromatograph, liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, shanghai's optical technique fluorescence spectrophotometer, wuhan Koste's electrochemical workstation, anhui Bei Yi g 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, the evaporator manufactured by Angstrom Engineering, the optical test system manufactured by Frieda, st. O. F. And the lifetime test system, ellipsometer manufactured by Beijing, etc.), in a manner well known to those skilled in the art. Since those skilled in the art are aware of the relevant contents of the device usage and the testing method, and can obtain the intrinsic data of the sample certainly and uninfluenced, the relevant contents are not further described in this patent.
Material synthesis examples:
the preparation method of the compound of the present invention is not limited, and is typically, but not limited to, exemplified by the following compounds, the synthetic routes and preparation methods thereof are as follows:
Synthesis example 1: synthesis of Compound A-2
Step 1: synthesis of intermediate C
In a three neck round bottom flask, intermediate A (22.2 g,106.0 mmol), intermediate B (17.7 g,106.0 mmol), cesium carbonate (Cs 2CO3, 69.1g,212.0 mmol) and 200mL of N, N-Dimethylformamide (DMF) were added sequentially. Under protection of N 2, the mixture was heated to reflux overnight. The reaction was completed by TLC, heating was stopped, and cooled to room temperature. Pouring the reaction liquid into a large amount of water, adding ethyl acetate for extraction, collecting an organic phase, and concentrating under reduced pressure to obtain a crude product. The crude product was slurried with absolute ethanol to give intermediate C (26.7 g,74.9 mmol) as a white solid in 70.7% yield.
Step 2: synthesis of intermediate E
In a three neck round bottom flask, intermediate C (18.9 g,53.0 mmol), intermediate D(9.5g,77.9mmol),Pd(PPh3)4(2.4g,2.1mmol),K2CO3(14.6g,106.0mmol),160mL toluene, 40mL EtOH and 40mL H 2 O were added sequentially. Under protection of N 2, the mixture was heated to reflux overnight. The reaction was completed by TLC, heating was stopped, and cooled to room temperature. The reaction was separated, the aqueous phase extracted with DCM and the organic phases combined. The organic phase was dried over anhydrous Na 2SO4, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (PE/dcm=10:1 to 8:1) to give intermediate E (16.8 g,47.5 mmol) as a white solid in 89.6% yield.
Step 3: synthesis of intermediate F
In a three neck round bottom flask, intermediate E (16.8 g,47.5 mmol), pinacol biborate (18.1 g,71.3 mmol), pd 2(dba)3 (0.87 g,0.95 mmol), tricyclohexylphosphine tetrafluoroborate (PCy 3·HBF4, 0.87g,0.95 mmol), KOAc (9.3 g,95.0 mmol) and 150mL 1, 4-Dioxane (Dioxane) were added sequentially. Under protection of N 2, the mixture was heated to reflux overnight. The reaction was completed by TLC, heating was stopped, and cooled to room temperature. The reaction system was filtered through celite, and the filtrate was concentrated under reduced pressure to give a crude product. The crude product was purified by silica gel column chromatography (PE/dcm=5:1 to 2:1) to give intermediate F (18.0 g,40.4 mmol) as a white solid in 85.0% yield.
Step 4: synthesis of intermediate H
In a three neck round bottom flask, intermediate G (27.3G, 100.0 mmol), pinacol biborate (33.0G, 130 mmol), pd (dppf) Cl 2 (1.46G, 2.0 mmol), KOAc (19.6G, 200.0 mmol) was added to 1, 4-dioxane (500 mL) and heated to reflux overnight under N 2. TLC confirmed the end of the reaction, stopped heating, and cooled to room temperature. The reaction was filtered through celite and the filtrate concentrated under reduced pressure, and the crude product was chromatographed on silica gel (PE/dcm=10:1 to 1:1) to give intermediate H (27.0 g,84.3 mmol) as a white solid in 84.3% yield.
Step 5: synthesis of intermediate J
In a three port round bottom flask, intermediate H (6.4 g,20.0 mmol), intermediate I (6.78 g,30.0 mmol), pd (PPh 3)4(0.69g,0.60mmol),Na2CO3 (6.24 g,40.0 mmol) was added to THF (96 mL), H 2 O (24 mL) under N 2 protection, heated reflux overnight, TLC confirmed the end of the reaction, stopped heating, cooled to room temperature, the separated aqueous phase was extracted with DCM, the combined organic phases, dried over anhydrous Na 2SO4, filtered, concentrated under reduced pressure, crude product was chromatographed over silica gel column (PE/DCM=5:1 to 2:1) to give intermediate J (3.9 g,10.1 mmol) as a white solid in 50.5% yield.
Step 6: synthesis of Compound A-2
In a three port round bottom flask, intermediate F (3.56 g,8.0 mmol), intermediate J (3.07 g,8.0 mmol) and Pd (PPh 3)4(0.28g,0.24mmol),K2CO3 (2.21 g,16.0 mmol) were added to toluene (40 mL), etOH (10 mL), H 2 O (10 mL) under N 2 and heated to reflux overnight. TLC confirmed the end of the reaction, stopped heating, cooled to room temperature, separated, the aqueous phase extracted with DCM, the combined organic phases dried over anhydrous Na 2SO4, filtered and concentrated under reduced pressure. Crude product was chromatographed over silica gel (PE/DCM=5:1 to 3:1) to give a white solid (4.2 g,6.3 mmol) in 78.7% yield as the target product A-2, molecular weight 666.3.
Synthesis example 2: synthesis of Compound A-3
Step 1: synthesis of intermediate L
In a three neck round bottom flask, intermediate K (27.3 g,100.0 mmol), pinacol biborate (50.8 g,200.0 mmol), pd (dppf) Cl 2 (1.46 g,2.0 mmol), KOAc (19.6 g,200.0 mmol) and 200mL 1, 4-dioxane were added sequentially. Under protection of N 2, the mixture was heated to reflux overnight. TLC confirmed the end of the reaction, stopped heating, and cooled to room temperature. The reaction was filtered through celite and the filtrate concentrated under reduced pressure, and the crude product was chromatographed on silica gel (PE/dcm=5:1 to 2:1) to give intermediate L (28.0 g,87.4 mmol) as a white solid in 87.4% yield.
Step 2: synthesis of intermediate M
In a three neck round bottom flask, intermediate L (10.0 g,31.2 mmol), intermediate I(8.5g,37.5mmol),Pd(PPh3)4(1.1g,0.98mmol),Na2CO3(6.6g,62.4mmol),240mL THF, and 60mL H 2 O were added sequentially. Under protection of N 2, the mixture was heated to reflux overnight. TLC confirmed the end of the reaction, stopped heating, cooled to room temperature, separated, the aqueous phase extracted with DCM, the combined organic phases dried over anhydrous Na 2SO4, filtered and concentrated under reduced pressure. The crude product was chromatographed on a column of silica gel (PE/dcm=8:1 to 4:1) to give intermediate M (6.9 g,18.0 mmol) as a white solid in 57.7% yield.
Step 3: synthesis of Compound A-3
In a three port round bottom flask, intermediate F (3.50 g,7.87 mmol), intermediate M (3.02 g,7.87 mmol) and Pd (PPh 3)4(0.28g,0.24mmol),K2CO3 (2.18 g,15.74 mmol) were added to toluene (40 mL), etOH (10 mL), H 2 O (10 mL) under N 2 and heated under reflux overnight. TLC confirmed the end of the reaction, cooled to room temperature, the separated aqueous phase was extracted with DCM, the combined organic phases dried over anhydrous Na 2SO4, filtered and concentrated under reduced pressure. The crude product was chromatographed over silica gel (PE/DCM=5:1 to 3:1) to give a white solid (4.2 g,6.3 mmol) in 80.0% yield as the target product A-3, molecular weight 666.3.
Synthesis example 3: synthesis of Compound A-11
Step 1: synthesis of intermediate O
In a three neck round bottom flask, intermediate H (9.6 g,30.0 mmol), intermediate N(11.8g,39.0mmol),Pd(PPh3)4(0.69g,0.60mmol),Na2CO3(6.36g,60.0mmol),240mL THF, and 60mL H 2 O were added sequentially. Under protection of N 2, the mixture was heated to reflux overnight. TLC confirmed the end of the reaction, stopped heating, cooled to room temperature, separated, the aqueous phase extracted with DCM, the combined organic phases dried over anhydrous Na 2SO4, filtered and concentrated under reduced pressure. The crude product was chromatographed on a column of silica gel (PE/dcm=8:1 to 3:1) to give intermediate O (8.3 g,18.0 mmol) as a white solid in 60.0% yield.
Step 2: synthesis of intermediate Q
In a three neck round bottom flask, intermediate P (30.0 g,99.7 mmol), intermediate D(13.4g,109.7mmol),Pd(PPh3)4(1.2g,1.0mmol),K2CO3(27.5g,199.4mmol),320mL toluene, 80mL EtOH and 80mL H 2 O were added sequentially. Under protection of N 2, the mixture was heated to reflux overnight. The reaction was completed by TLC, heating was stopped, and cooled to room temperature. The reaction was separated, the aqueous phase extracted with DCM and the organic phases combined. The organic phase was dried over anhydrous Na 2SO4, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (PE) to give intermediate Q (22.6 g,90.0 mmol) as a white solid in 90.3% yield.
Step 3: synthesis of intermediate R
In a three neck round bottom flask, intermediate Q (14.5 g,57.7 mmol), pinacol biborate (22.0 g,86.6 mmol), pd (dppf) Cl 2 (0.84 g,1.15 mmol), KOAc (11.3 g,115.4 mmol) and 300mL 1, 4-dioxane were added sequentially. Under protection of N 2, the mixture was heated to reflux overnight. The reaction was completed by TLC, heating was stopped, and cooled to room temperature. The reaction was filtered through celite and the filtrate concentrated under reduced pressure to give the crude product which was purified by silica gel column chromatography (PE/dcm=10:1 to 2:1) to give intermediate R (15.0 g,50.3 mmol) as a white solid in 87.2% yield.
Step 4: synthesis of intermediate S
In a three port round bottom flask, intermediate R (5.4 g,18.0 mmol), intermediate O (8.3 g,18.0 mmol), pd (PPh 3)4(0.42g,0.36mmol),K2CO3 (5.0 g,36.0 mmol) was added to toluene (60 mL), etOH (15 mL), H 2 O (15 mL) under N 2 protection and heated to reflux overnight.TLC confirmed the end of the reaction, stopped heating, cooled to room temperature, separated, the aqueous phase extracted with DCM, the combined organic phases dried over anhydrous Na 2SO4, filtered, concentrated under reduced pressure, crude product was chromatographed over silica gel column (PE/DCM=6:1 to 3:1) to afford intermediate S (10.4 g,17.46 mmol) as a white solid in 97.0% yield.
Step 5: synthesis of Compound A-11
In a three neck round bottom flask, intermediate S (5.5 g,9.2 mmol), intermediate B (1.7 g,10.1 mmol), cs 2CO3 (6.0 g,18.4 mmol) and 45mL of N, N-dimethylacetamide (DMAc) were added sequentially. Under protection of N 2, the mixture was heated to reflux overnight. The reaction was completed by TLC, heating was stopped, and cooled to room temperature. The reaction solution was poured into a large amount of water, and the solid was precipitated, suction-filtered under reduced pressure, and the obtained solid was purified by silica gel column chromatography (PE/dcm=10:1 to 3:1) to give a pale yellow solid (2.6 g,3.5 mmol) with a yield of 38.0%. The product was identified as target product A-11, having a molecular weight of 742.3.
Synthesis example 4: synthesis of Compound A-12
Step 1: synthesis of intermediate T
In a three neck round bottom flask, intermediate L (9.6 g,30.0 mmol), intermediate N(13.6g,45.0mmol),Pd(PPh3)4(1.04g,0.90mmol),Na2CO3(6.36g,60.0mmol),200mL THF, and 50mL H 2 O were added sequentially. Under protection of N 2, the mixture was heated to reflux overnight. TLC confirmed the end of the reaction, stopped heating, cooled to room temperature, separated, the aqueous phase extracted with DCM, the combined organic phases dried over anhydrous Na 2SO4, filtered and concentrated under reduced pressure. The crude product was chromatographed on silica gel (PE/dcm=8:1 to 3:1) to give intermediate T (8.8 g,19.13 mmol) as a white solid in 63.8% yield.
Step 2: synthesis of intermediate U
In a three port round bottom flask, intermediate R (3.63 g,12.17 mmol), intermediate T (5.6 g,12.17 mmol), pd (PPh 3)4(0.42g,0.36mmol),K2CO3 (3.36 g,24.34 mmol) was added to toluene (48 mL), etOH (12 mL), H 2 O (12 mL) under N 2 protection and heated to reflux overnight.TLC confirmed the end of the reaction, stopped heating, cooled to room temperature, separated, the aqueous phase extracted with DCM, the combined organic phases dried over anhydrous Na 2SO4, filtered, concentrated under reduced pressure, crude product was chromatographed over silica gel column (PE/DCM=6:1 to 2:1) to give intermediate U (6.6 g,11.08 mmol) as a white solid in 91.0% yield.
Step 3: synthesis of Compound A-12
In a three neck round bottom flask, intermediate U (4.2 g,7.05 mmol), intermediate B (1.3 g,7.76 mmol), cs 2CO3 (4.6 g,14.1 mmol) and 50mL DMF were added sequentially. Under protection of N 2, the mixture was heated to reflux overnight. The reaction was completed by TLC, heating was stopped, and cooled to room temperature. The reaction solution was poured into a large amount of water, and the solid was precipitated, suction-filtered under reduced pressure, and the obtained solid was purified by silica gel column chromatography (PE/dcm=6:1 to 2:1) to give a yellow solid (4.5 g,6.06 mmol) in 85.9% yield. The product was identified as target product A-12, having a molecular weight of 742.3.
Synthesis example 5: synthesis of Compound A-301
Step 1: synthesis of intermediate V
In a three neck round bottom flask, intermediate F (15.6 g,35.0 mmol), intermediate I(10.3g,45.5mmol),Pd(PPh3)4(0.81g,0.70mmol),Na2CO3(7.4g,70.0mmol),280mL THF, and 70mL H 2 O were added sequentially. And heating and refluxing under the protection of N 2. After 7h TLC confirmed the end of the reaction, stopped heating, cooled to room temperature, separated, the aqueous phase extracted with DCM, the combined organic phases dried over anhydrous Na 2SO4, filtered and concentrated under reduced pressure. The crude product was chromatographed on silica gel (PE/dcm=8:1 to 3:1) to give intermediate V (10.5 g,20.6 mmol) as a pale yellow solid in 58.9% yield.
Step 2: synthesis of intermediate X
In a three neck round bottom flask, intermediate W (9.9 g,25.0 mmol), pinacol biborate (9.5 g,37.5 mmol), pd (dppf) Cl 2 (0.55 g,0.75 mmol), KOAc (4.9 g,50.0 mmol) were added to 1, 4-dioxane (80 mL) and heated to reflux overnight under N 2. TLC confirmed the end of the reaction, stopped heating, and cooled to room temperature. The reaction was filtered through celite and the filtrate concentrated under reduced pressure, and the crude product was chromatographed on silica gel (PE/dcm=5:1 to 4:1) to give intermediate X (8.1 g,18.2 mmol) as a white solid in 72.9% yield.
Step 3: synthesis of Compound A-301
In a three port round bottom flask, intermediate V (3.0 g,5.9 mmol), intermediate X (2.6 g,5.9 mmol) and Pd (PPh 3)4(0.14g,0.12mmol),K2CO3 (1.6 g,11.8 mmol) were added to toluene (40 mL), etOH (10 mL), H 2 O (10 mL) under protection of N 2, heated reflux overnight.tlc confirmed the end of the reaction, stopped heating, cooled to room temperature, separated, aqueous phase extracted with DCM, combined organic phases, dried over anhydrous Na 2SO4, filtered, concentrated under reduced pressure the crude product was chromatographed over silica gel column (PE/dcm=5:1 to 3:1) to give a white solid (3.0 g,3.8 mmol) in 64.3% yield confirming the target product a-301, molecular weight 790.3.
Those skilled in the art will recognize that the above preparation method is only an illustrative example, and that those skilled in the art can modify it to obtain other compound structures of the present invention.
The method of manufacturing the electroluminescent device is not limited, and the following examples are only examples and should not be construed as limiting. Those skilled in the art will be able to make reasonable modifications to the preparation methods of the following examples in light of the prior art. The proportion of the various materials in the luminescent layer is not particularly limited, and a person skilled in the art can reasonably select the materials within a certain range according to the prior art, for example, the main material can occupy 80% -99% and the luminescent material can occupy 1% -20% based on the total weight of the luminescent layer; or the main material can account for 90% -99%, and the luminescent material can account for 1% -10%; or the main material may occupy 95% -99% and the luminescent material may occupy 1% -5%. In addition, the main material may be one or two materials, wherein the ratio of the two main materials to the main material may be 100:0 to 1:99, a step of; or the ratio may be 80:20 to 20:80; or the ratio may be 60:40 to 40:60. in an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, the evaporator manufactured by Angstrom Engineering, the optical test system manufactured by Frieda, st. O. F. And the lifetime test system, ellipsometer manufactured by Beijing, etc.), in a manner well known to those skilled in the art.
Device embodiment
Device example 1
First, a glass substrate having an 80nm thick Indium Tin Oxide (ITO) anode was cleaned, and then treated with oxygen plasma and UV ozone. After the treatment, the substrate was baked in a glove box to remove moisture. The substrate is then mounted on a substrate support and loaded into a vacuum chamber. The organic layer designated below was sequentially evaporated on the ITO anode by thermal vacuum evaporation at a rate of 0.2 to 2 Angstrom/second under a vacuum of about 10 -8 Torr. The compound HI was used as a hole injection layer (HIL, thickness of). The compound HT is used as hole transport layer (HTL, thickness/>). Compound PH-23 is used as an electron blocking layer (EBL, thickness is). Then, the compound GD23 was doped in the compound PH-23 and the compound A-2 of the present invention, and co-evaporation was used as a light emitting layer (EML, thickness is/>The weight ratio is 8:64:28). The compound HB was used as a hole blocking layer (HBL, thickness/>). On the hole blocking layer, a compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an electron transport layer (ETL, thicknessThe weight ratio is 40:60). Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1nm was evaporated as an electron injection layer, and 120nm of aluminum was evaporated as a cathode. The device was then transferred back to the glove box and packaged with a glass lid to complete the device.
Device example 2
Device example 2 was prepared in the same manner as device example 1 except that the compound A-3 of the present invention was used in place of the compound A-2 of the present invention in the light-emitting layer (EML).
Device example 3
Device example 3 was prepared in the same manner as device example 1 except that the compound A-11 of the present invention was used in place of the compound A-2 of the present invention in the light-emitting layer (EML).
Device comparative example 1
Device comparative example 1 was prepared in the same manner as device example 1 except that compound C-1 was used in place of the inventive compound a-2 in the light-emitting layer (EML).
Device comparative example 2
Device comparative example 2 was prepared in the same manner as device example 1 except that compound C-2 was used in place of the compound a-2 of the present invention in the light-emitting layer (EML).
Device comparative example 3
Device comparative example 3 was prepared in the same manner as device example 1 except that compound C-3 was used in place of the compound a-2 of the present invention in the light-emitting layer (EML).
The detailed device layer structure and thickness are shown in the following table. Wherein more than one layer of the material used is doped with different compounds in the weight proportions described.
Table 1 partial device structures of device examples 1 to 3 and comparative examples 1 to 3
The material structure used in the device is as follows:
/>
Table 2 shows CIE data, driving voltage, external Quantum Efficiency (EQE) and Current Efficiency (CE) measured at 15mA/cm 2 constant current; and device lifetime (LT 95) measured at a constant current of 80mA/cm 2.
Table 2 device data for examples 1 to 3 and comparative examples 1 to 3
/>
Discussion:
As can be seen from table 2, the voltage of comparative example 1 is at a low voltage level, although the voltages of examples 1-2 are slightly higher than comparative example 1, but still at a low voltage level. The External Quantum Efficiency (EQE) and the Current Efficiency (CE) of comparative example 1 have reached very high levels, whereas examples 1-2 maintain very high levels of efficiency or achieve further improvement of comparative example 1 compared to comparative example 1. More importantly, the device lifetime of example 1 was greatly improved by 1.64 times as compared to comparative example 1, the device lifetime of example 2 was greatly improved by 1.25 times, and the devices of example 1, example 2 and comparative example 1 were only different in that triazine was attached to different positions of fluorenyl group in the host compound, since the specific structure of the compound of formula 1 of the present invention enabled the great improvement of device lifetime, which was unexpected, demonstrating the superiority of the compound of the present invention having the structure of formula 1.
Likewise, the voltage of comparative example 2 is at a low voltage level, while the voltage of example 1 is also at a low voltage level substantially equivalent thereto. The External Quantum Efficiency (EQE) and the Current Efficiency (CE) of comparative example 2 have reached very high levels, whereas example 1 can achieve further improvement over comparative example 2 in the very high efficiency level. More importantly, the device lifetime of example 1 was greatly improved by 76.2% as compared to comparative example 2, whereas the device of example 1 and comparative example 2 only differed in the presence or absence of a phenyl substituent on the phenylene group of the bridging group in which carbazole and triazine are linked in the host compound, which was unexpected because the specific structure of the compound of formula 1 of the present invention enabled a great improvement in device lifetime, demonstrating the superiority of the compound of the present invention having the structure of formula 1.
Similarly, the voltage of example 1 was at a low voltage level and was slightly reduced relative to the voltage of comparative example 3. The External Quantum Efficiency (EQE) and the Current Efficiency (CE) of comparative example 3 have reached very high levels, whereas example 1 can maintain very high efficiency levels of comparative example 3 as compared to comparative example 3. More importantly, the device lifetime of example 1 was greatly improved by 12.7 times as compared to comparative example 3, whereas the device of example 1 and comparative example 3 were only different in that the host compound replaced dimethylfluorenyl group with dibenzofuranyl group, which was unexpected because the specific structure of the compound of formula 1 of the present invention enabled the great improvement in device lifetime, demonstrating the superiority of the compound of formula 1 of the present invention.
In addition, example 3, which uses a compound having a different carbazole linkage site and a different Ar structure than example 1, also obtained a low voltage, high efficiency and long life comparable to example 1, further demonstrated the superiority of the compound having the structure of formula 1 of the present invention.
Device example 4
Device example 4 was prepared in the same manner as device example 1 except that compound A-301 according to the present invention was used in place of compound A-2 according to the present invention in the light-emitting layer (EML).
Device comparative example 4
Device comparative example 4 was prepared in the same manner as in device example 1 except that compound C-4 was used in place of the compound A-2 of the present invention in the light-emitting layer (EML).
The detailed device layer structure and thickness are shown in the following table. Wherein more than one layer of the material used is doped with different compounds in the weight proportions described.
Table 3 partial device structures of device example 4 and comparative example 4
The structure of the materials newly used in the device is as follows:
table 4 shows CIE data, driving voltage, external Quantum Efficiency (EQE) and Current Efficiency (CE) measured at 15mA/cm 2 constant current.
Table 4 device data for example 4 and comparative example 4
The device of example 4 and comparative example 4 only differs in whether heteroaryl substituent is further on the bridging group phenylene in which carbazole and triazine are linked in the host compound, and it can be seen from table 4 that the voltage of example 4 is at a low voltage level and is reduced by 0.28v, eqe is improved by 17.9%, CE is improved by 19.1%, and the overall performance of the device is further improved, demonstrating the superiority of the compound having the structure of formula 1 of the present invention.
In summary, when the compound of the present invention is used as a host material of a light emitting layer, the electron and hole transport balance of the material is improved, and the comprehensive performance of the device can be greatly improved, for example, the device efficiency (EQE and CE) is high, the driving voltage is low, and/or the lifetime of the device is greatly improved, compared to when the compound of the present invention is not used as a host material of a light emitting layer. This is an important aid to the industry.
Device example 5
First, a glass substrate having an 80nm thick Indium Tin Oxide (ITO) anode was cleaned, and then treated with oxygen plasma and UV ozone. After the treatment, the substrate was baked in a glove box to remove moisture. The substrate is then mounted on a substrate support and loaded into a vacuum chamber. The organic layer designated below was sequentially evaporated on the ITO anode by thermal vacuum evaporation at a rate of 0.2 to 2 Angstrom/second under a vacuum of about 10 -8 Torr. The compound HI was used as a hole injection layer (HIL, thickness of). The compound HT is used as hole transport layer (HTL, thickness/>). Compound PH-23 is used as an electron blocking layer (EBL, thickness/>). Then, the compound GD23 was doped in the compound PH-23 and the compound NH-1, and co-evaporation was used as a light emitting layer (EML, thickness is/>The weight ratio is 8:46:46). The compound HB was used as a hole blocking layer (HBL, thickness/>). On the hole blocking layer, the compound A-2 and 8-hydroxyquinoline-lithium (Liq) of the invention are co-evaporated as an electron transport layer (ETL, thickness isThe weight ratio is 40:60). Finally, 8-hydroxyquinoline-lithium (Liq) with a thickness of 1nm was evaporated as an electron injection layer, and 120nm of aluminum was evaporated as a cathode. The device was then transferred back to the glove box and packaged with a glass lid to complete the device.
Device example 6
Device example 6 was prepared in the same manner as device example 5, except that the compound A-3 of the present invention was used in place of the compound A-2 of the present invention in the Electron Transport Layer (ETL).
Device comparative example 5
Device comparative example 5 was prepared in the same manner as device example 5 except that compound ET was used in place of the inventive compound a-2 in the Electron Transport Layer (ETL).
The detailed device layer structure and thickness are shown in the following table. Wherein more than one layer of the material used is doped with different compounds in the weight proportions described.
Table 5 partial device structures of device example 5, example 6 and comparative example 5
The structure of the materials newly used in the device is as follows:
Table 6 shows CIE data and External Quantum Efficiencies (EQEs) measured at 15mA/cm 2 constant current; and device lifetime (LT 95) measured at a constant current of 80mA/cm 2.
Table 6 device data for example 5, example 6 and comparative example 6
| Device ID | CIE(x,y) | EQE(％) | LT95(h) |
| Example 5 | (0.356,0.619) | 21.25 | 85 |
| Example 6 | (0.355,0.620) | 21.11 | 79 |
| Comparative example 5 | (0.354,0.621) | 20.96 | 78 |
Discussion:
In example 5, example 6 and comparative example 5, the compounds A-2, A-3 and the comparative compound ET of the present invention were used as electron transport materials, respectively. Both the EQE and device lifetime of example 5 and example 6 are improved compared to comparative example 5. It should be noted that the compound ET is a commercial electron transport material at present, and compared with the compound ET, the application of the compound of the present invention to an electroluminescent device can obtain a further improved device level, which is very difficult to obtain, and it can be seen that the compound of the present invention is also a very excellent electron transport material with commercial potential.
In summary, the compound disclosed by the invention is applied to an organic electroluminescent device, can improve the comprehensive performance of the device, for example, has high device efficiency and low driving voltage, and/or greatly prolongs the service life of the device, and has a wider application prospect.
It should be understood that the various embodiments described herein are by way of example only and are not intended to limit the scope of the invention. Thus, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific and preferred embodiments described herein. Many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the invention. It is to be understood that the various theories as to why the present invention works are not intended to be limiting.
Claims (17)
1. A compound having the structure of formula 1:
In the formula (1) of the present invention,
One of X 1 and X 2 is selected from C, and the other is selected from CR x or N;
y 1 and Y 2 are, identically or differently, selected for each occurrence from CR y or N;
z 1-Z5 is selected identically or differently on each occurrence from CR z or N;
U 1-U4 is selected identically or differently on each occurrence from CR u or N;
V 1-V4 is selected identically or differently on each occurrence from CR v or N;
E is selected identically or differently on each occurrence from CRR or SiRR;
One of E 1,E3 and E 4 is selected from C and is linked to L in formula 1, and the remaining two are selected, identically or differently, from CR e or N at each occurrence;
E 2 and E 5-E8 are selected identically or differently on each occurrence from CR e or N;
Ar is selected, identically or differently, for each occurrence, from a substituted or unsubstituted aryl group having from 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having from 3 to 30 carbon atoms, or a combination thereof;
l is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
R x,Rz,Ru,Rv,Re and R are 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 heteroaryl having 3 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 alkyl 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 atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
R y 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 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 alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkylgermanium having 6 to 20 carbon atoms, substituted or unsubstituted arylgermanium having 6 to 20 carbon atoms, carbonyl, isocyanate, sulfonyl, and combinations thereof;
Adjacent substituents R y can optionally be linked to form a ring; adjacent substituents R z can optionally be linked to form a ring; adjacent substituents R u can optionally be linked to form a ring; adjacent substituents R v can optionally be linked to form a ring; adjacent substituents R e can optionally be linked to form a ring; adjacent substituents R can optionally be joined to form a ring.
2. The compound of claim 1, wherein E is selected from CRR;
preferably, each occurrence of said R 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 alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof;
More preferably, each occurrence of said R is the same or different selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted n-propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted n-butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted neopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and combinations thereof.
3. The compound of claim 1 or 2, wherein one of X 1 and X 2 is selected from C and the other is selected from CR x; and/or Y 1 and Y 2 are, identically or differently, selected from CR y at each occurrence; and/or Z 1-Z5 is selected identically or differently on each occurrence from CR z.
4. A compound as claimed in claims 1-3 wherein said U 1-U4 is selected identically or differently on each occurrence from CR u; and/or V 1-V4 is selected identically or differently on each occurrence from CR v; and/or one of E 1,E3 and E 4 is selected from C and is linked to L in formula 1, the remaining two are selected from CR e,E2 and E 5-E8, identically or differently, at each occurrence, from CR e.
5. The compound of any one of claims 1-4, wherein said Ar is, identically or differently, selected from a substituted or unsubstituted aryl group having 6-20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3-20 carbon atoms, or a combination thereof;
Preferably, ar is selected identically or differently on each occurrence from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and combinations thereof.
6. The compound of any one of claims 1-5, wherein the L is, identically or differently, selected from a single bond, a substituted or unsubstituted arylene group having 6-20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3-20 carbon atoms, or a combination thereof;
Preferably, L is selected, identically or differently, for each occurrence, from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted pyridylene group, or a combination thereof;
more preferably, L is, identically or differently, selected for each occurrence from a single bond, or a substituted or unsubstituted phenylene group.
7. The compound of any one of claims 1-6, wherein each occurrence of R x,Rz,Ru,Rv and R e is identically or differently 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 alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 20 carbon atoms, cyano groups, and combinations thereof;
Preferably, R x,Rz,Ru,Rv and R e are, identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and combinations thereof.
8. The compound of any one of claims 1-7, wherein the R y 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 alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, cyano groups, and combinations thereof;
Preferably, R y is selected identically or differently on each occurrence from the group consisting of: hydrogen, deuterium, fluorine, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, and combinations thereof.
9. The compound of claim 1, wherein the compound is selected from the group consisting of:
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Wherein, optionally, hydrogen in the above compounds A-1 to A-460 can be partially or completely substituted with deuterium.
10. An organic electroluminescent device, comprising:
an anode is provided with a cathode,
A cathode electrode, which is arranged on the surface of the cathode,
And an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the compound of any one of claims 1-9.
11. The organic electroluminescent device according to claim 10, wherein the organic layer is a light-emitting layer, and the compound is a host compound; or the organic layer is an electron transport layer, and the compound is an electron transport compound; or the organic layer is a hole blocking layer and the compound is a hole blocking compound.
12. The organic electroluminescent device according to claim 10, wherein the organic layer is a light-emitting layer, and the compound is a host compound; the light emitting layer comprises a first metal complex having the general formula of M (L a)m(Lb)n(Lc)q;
the metal M is selected from metals with relative atomic mass of more than 40;
L a,Lb,Lc is a first ligand, a second ligand and a third ligand, respectively, which are coordinated to the metal M, and the ligands L a,Lb,Lc may be the same or different;
ligand L a,Lb,Lc can optionally be linked to form a multidentate ligand;
m is 1,2 or 3; n is 0,1 or 2; q is 0,1 or 2; the sum of M, n, q is equal to the oxidation state of the metal M; when m is 2 or more, the plurality of L a may be the same or different; when n is 2, two L b may be the same or different; when q is 2, two L c may be the same or different;
ligand L a has a structure as shown in formula 2:
Ring C 1 and ring C 2 are, identically or differently, selected from aromatic rings having 5 to 30 ring atoms, heteroaromatic rings having 5 to 30 ring atoms, or combinations thereof;
Q 1 and Q 2 are selected identically or differently on each occurrence from C or N;
Each occurrence of A 1 and A 2 is identically or differently selected from single bonds, O or S;
L 1 is selected identically or differently on each occurrence from the group consisting of: a single bond, BR ', CR ' R ', NR ', O, siR ' R ', PR ', S, geR ' R ', se, a substituted or unsubstituted vinylidene group, an ethynylene group, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms, and combinations thereof; when two R's are present at the same time, the two R's are the same or different;
R 11 and R 12, which are identical or different for each occurrence, represent mono-substituted, polysubstituted or unsubstituted;
R', R 11 and R 12 are 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 heteroaryl having 3 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 alkyl 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 atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
adjacent substituents R', R 11 and R 12 can optionally be linked to form a ring;
The ligands L b and L c are, identically or differently, selected from monoanionic bidentate ligands at each occurrence;
Preferably, the ligand L b,Lc is selected identically or differently on each occurrence from either or both of the following structures:
Wherein,
R a,Rb and R c, which are identical or different at each occurrence, represent monosubstituted, polysubstituted or unsubstituted;
X b is selected identically or differently on each occurrence from the group consisting of: o, S, se, NR N1 and CR C1RC2;
X c and X d are selected identically or differently on each occurrence from the group consisting of: o, S, se and NR N2;
R a,Rb,Rc,RN1,RN2,RC1 and R C2 are 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 heteroaryl having 3 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 alkyl 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 atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
Adjacent substituents R a,Rb,Rc,RN1,RN2,RC1 and R C2 can optionally be linked to form a ring.
13. The organic electroluminescent device of claim 12, wherein the first metal complex is selected from the group consisting of:
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wherein, optionally, hydrogen in the above-mentioned compounds GD1 to GD76 can be partially or entirely substituted with deuterium.
14. The organic electroluminescent device of claim 11 or 12, wherein the organic layer is a light-emitting layer, the compound is a host compound, and a second host compound is further included in the light-emitting layer, the second host compound comprising 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;
Preferably, the second host compound comprises at least one chemical group selected from the group consisting of: benzene, carbazole, indolocarbazole, fluorene, silafluorene, and combinations thereof.
15. The organic electroluminescent device of claim 14, wherein the second host compound has a structure represented by formula 3 or formula 4:
Wherein,
G is selected identically or differently for each occurrence from C (R g)2,NRg, O or S;
L T is selected, identically or differently, 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;
t is selected identically or differently on each occurrence from C, CR t or N;
R t,Rg 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 heteroaryl having 3 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 alkyl 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 atoms, substituted or unsubstituted alkyl germanium having 3 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, carbonyl having 0 to 20 carbon atoms, cyano, sulfonyl, cyano, carbonyl, cyano, sulfonyl, cyano, or the like;
Ar 1 and Ar 2 are, identically or differently, selected from the group consisting of 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;
Adjacent substituents R t,Rg can optionally be linked to form a ring.
16. The organic electroluminescent device of claim 14, wherein the second host compound is selected from the group consisting of:
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17. A compound composition comprising a compound according to any one of claims 1-9.
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| KR1020230144812A KR20240063775A (en) | 2022-10-31 | 2023-10-26 | Organic electroluminescent material and device thereof |
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