CN110431679A - Organic illuminating element - Google Patents
Organic illuminating element Download PDFInfo
- Publication number
- CN110431679A CN110431679A CN201880017338.4A CN201880017338A CN110431679A CN 110431679 A CN110431679 A CN 110431679A CN 201880017338 A CN201880017338 A CN 201880017338A CN 110431679 A CN110431679 A CN 110431679A
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- Prior art keywords
- substituted
- unsubstituted
- chemical formula
- mentioned
- compound
- Prior art date
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- Granted
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- 239000000126 substance Substances 0.000 claims abstract description 352
- 150000001875 compounds Chemical class 0.000 claims abstract description 301
- 230000004888 barrier function Effects 0.000 claims abstract description 37
- -1 nitro, hydroxyl Chemical group 0.000 claims description 120
- 125000003118 aryl group Chemical group 0.000 claims description 90
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 239000001257 hydrogen Substances 0.000 claims description 53
- 125000001072 heteroaryl group Chemical group 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 238000004770 highest occupied molecular orbital Methods 0.000 claims description 37
- 239000005416 organic matter Substances 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 238000006467 substitution reaction Methods 0.000 claims description 28
- 238000002347 injection Methods 0.000 claims description 27
- 239000007924 injection Substances 0.000 claims description 27
- 125000003368 amide group Chemical group 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 230000005540 biological transmission Effects 0.000 claims description 22
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 21
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 20
- 230000003647 oxidation Effects 0.000 claims description 19
- 238000007254 oxidation reaction Methods 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 15
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 15
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 15
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 14
- 125000000707 boryl group Chemical group B* 0.000 claims description 14
- 229910052805 deuterium Inorganic materials 0.000 claims description 14
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 14
- 125000004104 aryloxy group Chemical group 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000003003 spiro group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 7
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 7
- 230000000903 blocking effect Effects 0.000 claims description 7
- 150000002790 naphthalenes Chemical class 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 6
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 6
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
- LJJQENSFXLXPIV-UHFFFAOYSA-N fluorenylidene Chemical group C1=CC=C2[C]C3=CC=CC=C3C2=C1 LJJQENSFXLXPIV-UHFFFAOYSA-N 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 101000869592 Daucus carota Major allergen Dau c 1 Proteins 0.000 claims description 2
- 101000650136 Homo sapiens WAS/WASL-interacting protein family member 3 Proteins 0.000 claims description 2
- 101000585507 Solanum tuberosum Cytochrome b-c1 complex subunit 7 Proteins 0.000 claims description 2
- 102100027539 WAS/WASL-interacting protein family member 3 Human genes 0.000 claims description 2
- 125000004653 anthracenylene group Chemical group 0.000 claims description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
- 125000005562 phenanthrylene group Chemical group 0.000 claims description 2
- 125000000169 tricyclic heterocycle group Chemical group 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 254
- 239000002585 base Substances 0.000 description 108
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 107
- 238000000034 method Methods 0.000 description 99
- 238000004519 manufacturing process Methods 0.000 description 76
- 229910052799 carbon Inorganic materials 0.000 description 46
- 150000001721 carbon Chemical group 0.000 description 43
- 230000015572 biosynthetic process Effects 0.000 description 28
- 230000000052 comparative effect Effects 0.000 description 28
- 238000003786 synthesis reaction Methods 0.000 description 26
- 125000001424 substituent group Chemical group 0.000 description 22
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- 238000002474 experimental method Methods 0.000 description 15
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 13
- 229910052782 aluminium Inorganic materials 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 10
- 238000007738 vacuum evaporation Methods 0.000 description 10
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 9
- 239000002019 doping agent Substances 0.000 description 9
- 238000004020 luminiscence type Methods 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- 239000004411 aluminium Substances 0.000 description 8
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 8
- 125000005264 aryl amine group Chemical group 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 150000004982 aromatic amines Chemical class 0.000 description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 6
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 6
- 229910052737 gold Inorganic materials 0.000 description 6
- 239000010931 gold Substances 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 238000004776 molecular orbital Methods 0.000 description 6
- 238000005424 photoluminescence Methods 0.000 description 6
- 125000003367 polycyclic group Chemical group 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 5
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 5
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 150000004696 coordination complex Chemical class 0.000 description 5
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 5
- 150000002220 fluorenes Chemical class 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- SFMJNHNUOVADRW-UHFFFAOYSA-N n-[5-[9-[4-(methanesulfonamido)phenyl]-2-oxobenzo[h][1,6]naphthyridin-1-yl]-2-methylphenyl]prop-2-enamide Chemical compound C1=C(NC(=O)C=C)C(C)=CC=C1N1C(=O)C=CC2=C1C1=CC(C=3C=CC(NS(C)(=O)=O)=CC=3)=CC=C1N=C2 SFMJNHNUOVADRW-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 239000010405 anode material Substances 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 150000002240 furans Chemical class 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 150000004767 nitrides Chemical class 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 238000001420 photoelectron spectroscopy Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000005580 triphenylene group Chemical group 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 3
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KDOKHBNNNHBVNJ-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12.N1C=CC=CC=C1 Chemical compound C1=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12.N1C=CC=CC=C1 KDOKHBNNNHBVNJ-UHFFFAOYSA-N 0.000 description 3
- SXDPQGRNHSLZPC-ZJNRKIDTSA-N CNC(=O)C[C@@H]1C[C@H]([C@@H](CN1)NC(=O)c1cc(c(Cl)o1)-c1c(Cl)cnn1C)c1ccc(F)c(F)c1 Chemical compound CNC(=O)C[C@@H]1C[C@H]([C@@H](CN1)NC(=O)c1cc(c(Cl)o1)-c1c(Cl)cnn1C)c1ccc(F)c(F)c1 SXDPQGRNHSLZPC-ZJNRKIDTSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229960003540 oxyquinoline Drugs 0.000 description 3
- 125000005561 phenanthryl group Chemical group 0.000 description 3
- 238000005240 physical vapour deposition Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- 150000004325 8-hydroxyquinolines Chemical class 0.000 description 2
- HJCUTNIGJHJGCF-UHFFFAOYSA-N 9,10-dihydroacridine Chemical class C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 229910052688 Gadolinium Inorganic materials 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- 229910052772 Samarium Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
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- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical class C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- YTZKOQUCBOVLHL-UHFFFAOYSA-N p-methylisopropylbenzene Natural products CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [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 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical class CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
- H10K50/181—Electron blocking layers
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
This specification is related to a kind of organic illuminating element, it includes: the luminescent layer of anode, cathode and offer between above-mentioned anode and above-mentioned cathode, above-mentioned organic illuminating element also includes: the electronic barrier layer for providing the electrical adjustment layer between above-mentioned luminescent layer and above-mentioned cathode and containing the compound indicated by chemical formula 1 and providing between above-mentioned luminescent layer and above-mentioned anode and containing the compound indicated by chemical formula 3.
Description
Technical field
The South Korea patent application 10-2017- that this application claims submitted based on 06 08th, 2017 to Koran Office
No. 0071681 priority, entire contents include in the present specification.
This specification is related to organic illuminating element.
Background technique
Under normal conditions, organic light emission phenomenon refers to the phenomenon that making electric energy be converted to luminous energy using organic substance.Using having
The organic illuminating element of machine luminescence phenomenon usually has comprising anode and cathode and between above-mentioned anode and above-mentioned cathode
Organic matter layer structure.Herein, in order to improve the efficiency and stability of organic illuminating element, organic matter layer is in most cases
Formed by being utilized respectively the multilayered structure that different substances is constituted, for example, can by hole injection layer, hole transmission layer, shine
The formation such as layer, electron transfer layer, electron injecting layer.For the structure of such organic illuminating element, if in two electrodes
Between apply voltage, then hole is injected into organic matter layer from anode, and electronics is injected into organic matter layer from cathode, when the sky injected
Cave and electronics will form exciton (exciton) when meeting, and light will be issued when the exciton transits to ground state again.
The lasting new material for requiring exploitation to be used for organic illuminating element as described above.
Summary of the invention
Technical task
This specification provides organic illuminating element.
The method to solve the problem
According to an embodiment of this specification, a kind of organic illuminating element is provided, it includes: anode, cathode, Yi Jiti
For the luminescent layer between above-mentioned anode and above-mentioned cathode, above-mentioned organic illuminating element also includes:
Electrical adjustment layer is provided between above-mentioned luminescent layer and above-mentioned cathode and containing being indicated by following chemical formula 1
Compound, and
Electronic barrier layer is provided between above-mentioned luminescent layer and above-mentioned anode and containing being indicated by following chemical formula 3
Compound,
[chemical formula 1]
In above-mentioned chemical formula 1,
R1 is hydrogen, deuterium, itrile group, nitro, hydroxyl ,-C (=O) NC (=O) R ,-C (=O) R ,-C (=O) NRR' ,-C (=O)
It is OR, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted alkoxy, substituted or unsubstituted
Aryloxy group, substituted or unsubstituted alkyl sulfenyl (Alkyl thioxy), it is substituted or unsubstituted
Artyl sulfo ( Aryl thioxy), substituted or unsubstituted alkyl sulphonyl (Alkyl sulfoxy), substituted or unsubstituted aryl sulfonyl (Aryl
Sulfoxy), substituted or unsubstituted alkenyl, substituted or unsubstituted silicyl, substituted or unsubstituted boryl, substitution or
Unsubstituted amido, substituted or unsubstituted aryl phosphino-, substituted or unsubstituted oxidation phosphino-, substituted or unsubstituted virtue
Base or substituted or unsubstituted heteroaryl, R and R' are same or different to each other, and are each independently alkyl, naphthenic base or virtue
Base,
L1 be Direct Bonding, substituted or unsubstituted arlydene or substituted or unsubstituted inferior heteroaryl,
Ar1 be hydrogen, deuterium, itrile group, nitro, hydroxyl ,-C (=O) NC (=O) R ,-C (=O) R ,-C (=O) NRR' ,-C (=
O it) OR, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted alkoxy, substitution or does not take
The aryloxy group in generation, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted artyl sulfo, substituted or unsubstituted alkyl sulphur
Acyl group, substituted or unsubstituted aryl sulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silicyl, substitution
Or unsubstituted boryl, substituted or unsubstituted amido, substituted or unsubstituted aryl phosphino-, substituted or unsubstituted phosphine oxide
Base, substituted or unsubstituted aryl, the heterocycle of substituted or unsubstituted monocycle, heterocycle more than substituted or unsubstituted tricyclic
Base, it is substituted or unsubstituted include the bicyclic heterocycle of 2 or more N, substituted or unsubstituted isoquinolyl or by following
The structure that chemical formula 2 indicates, R and R' are same or different to each other, and are each independently alkyl, naphthenic base or aryl,
The integer that m is 1 to 4, the integer that n is 0 to 3,1≤n+m≤4,
When m and n is respectively 2 or more integer, the structure in 2 or more brackets is same or different to each other,
[chemical formula 2]
In above-mentioned chemical formula 2,
G1 is hydrogen, deuterium, itrile group, nitro, hydroxyl, C (=O) NC (=O) R ,-C (=O) R ,-C (=O) NRR' ,-C (=O)
It is OR, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted alkoxy, substituted or unsubstituted
Aryloxy group, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted artyl sulfo, substituted or unsubstituted alkyl sulfonyl
Base, substituted or unsubstituted aryl sulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silicyl, substitution or
Unsubstituted boryl, substituted or unsubstituted amido, substituted or unsubstituted aryl phosphino-, substituted or unsubstituted phosphine oxide
Base, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, R and R' are same or different to each other, each independently
For alkyl, naphthenic base or aryl,
The integer that g1 is 1 to 6, when g1 is 2 or more, above-mentioned G1 is same or different to each other,
It * is the position in conjunction with the L1 of above-mentioned chemical formula 1,
[chemical formula 3]
In above-mentioned chemical formula 3,
L'1 to L'3 is same or different to each other, be each independently Direct Bonding, substituted or unsubstituted arlydene or
Substituted or unsubstituted inferior heteroaryl,
N'1 to n'3 is respectively 1 to 4 integer, and when n'1 to n'3 is respectively 2 or more integer, the structure in bracket is each other
It is identical or different,
Ar'1 to Ar'3 is same or different to each other, be each independently hydrogen, substituted or unsubstituted aryl or substitution or
Unsubstituted heteroaryl, or indicated by following chemical formula 4 or 5,
At least one of Ar'1 to Ar'3 indicates by following chemical formula 4,
[chemical formula 4]
[chemical formula 5]
In above-mentioned chemical formula 4 and 5,
Any of R'1 to R'8 and R'9 is the position of a combination with the L'1 of above-mentioned chemical formula 3 into L'3,
Its remaining part other than the part of a combination with the L'1 of above-mentioned chemical formula 3 into L'3 of R'1 into R'9
Point and R'10 to R'21 be same or different to each other, be each independently hydrogen, deuterium, itrile group, nitro, hydroxyl ,-C (=O) NC (=
O) R ,-C (=O) R ,-C (=O) NRR' ,-C (=O) OR, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, take
It is generation or unsubstituted alkoxy, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted
Artyl sulfo, substituted or unsubstituted alkyl sulphonyl, substituted or unsubstituted aryl sulfonyl, substituted or unsubstituted alkene
It is base, substituted or unsubstituted silicyl, substituted or unsubstituted boryl, substituted or unsubstituted amido, substituted or unsubstituted
Aryl phosphino-, substituted or unsubstituted oxidation phosphino-, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl
Base, R and R' are same or different to each other, and are each independently alkyl, naphthenic base or aryl.
Invention effect
The raising of efficiency, low driving voltage may be implemented according to the organic illuminating element of an embodiment of this specification
And/or the raising of life characteristic.
Detailed description of the invention
Fig. 1 illustrates the organic illuminating elements 10 according to the embodiment of this specification.
Fig. 2 illustrates the organic illuminating element 11 of another embodiment according to this specification.
Fig. 3 illustrates the organic illuminating element 12 of another embodiment according to this specification.
Fig. 4, which is illustrated, utilizes photoelectron energy to the compound E1 of the Production Example 1-1 according to the embodiment of this specification
The HOMO energy level of spectral apparatus measurement.
Fig. 5, which is illustrated, utilizes photoelectron energy to the compound E2 of the Production Example 1-2 according to the embodiment of this specification
The HOMO energy level of spectral apparatus measurement.
Fig. 6 illustrates the HOMO energy level that the measurement of photoelectron spectroscopy device is utilized to compound [ET-1-J].
Fig. 7 is illustrated through luminescence generated by light (photoluminescence；PL) to the embodiment party according to this specification
The lumo energy that wavelength value obtained from the compound E1 of the Production Example 1-1 of formula is measured calculates.
Fig. 8 is illustrated through luminescence generated by light (photoluminescence；PL) to the embodiment party according to this specification
The lumo energy that wavelength value obtained from the compound E2 of the Production Example 1-2 of formula is measured calculates.
Fig. 9 is illustrated through luminescence generated by light (photoluminescence；PL) compound [ET-1-J] is measured
Obtained from wavelength value calculate lumo energy.
Figure 10, which is illustrated, utilizes Chem 3D to the compound E9 of the Production Example 1-9 according to the embodiment of this specification
The 3D structure of molecule obtained from Pro.
Figure 11, which is illustrated, utilizes Chem to the compound E18 of the Production Example 1-18 according to the embodiment of this specification
The 3D structure of molecule obtained from 3D Pro.
Figure 12 illustrates the 3D structure to compound [ET-1-E] molecule obtained from Chem 3D Pro.
Figure 13 illustrates the 3D structure to compound [ET-1-I] molecule obtained from Chem 3D Pro.
Figure 14, which is illustrated, utilizes photoelectron energy to the compound F1 of the Production Example 2-1 according to the embodiment of this specification
The HOMO energy level of spectral apparatus measurement.
Figure 15 illustrates the HOMO energy level that the measurement of photoelectron spectroscopy device is utilized to compound [HT-1-B].
Figure 16 is illustrated through luminescence generated by light (photoluminescence；PL) to the implementation according to this specification
The lumo energy that wavelength value obtained from the compound F1 of the Production Example 2-1 of mode is measured calculates.
Figure 17 is illustrated through luminescence generated by light (photoluminescence；PL) compound [HT-1-B] is surveyed
The lumo energy that wavelength value obtained from fixed calculates.
Specific embodiment
In the following, being illustrated in more details to this specification.
This specification provides a kind of organic illuminating element, it includes: anode, cathode and provide above-mentioned anode with it is upper
The luminescent layer between cathode is stated, above-mentioned organic illuminating element also includes:
Electrical adjustment layer is provided between above-mentioned luminescent layer and above-mentioned cathode and containing being indicated by above-mentioned chemical formula 1
Compound, and
Electronic barrier layer is provided between above-mentioned luminescent layer and above-mentioned anode and containing being indicated by above-mentioned chemical formula 3
Compound.
According to the organic illuminating element of an embodiment of this specification by hindering included in electrical adjustment layer and electronics
Substance in barrier is adjusted to adjust the energy level of each interlayer, special so as to improve driving voltage, efficiency and/or service life
Property.
According to an embodiment of this specification, it is included in by the compound that above-mentioned chemical formula 1 indicates with nonlinear organization
In electrical adjustment layer, mentioning for the raising of efficiency, lower driving voltage and life characteristic may be implemented in organic illuminating element
It is high.In addition, substituent A r1 has depleted of electrons structure in the structure of the compound indicated by above-mentioned chemical formula 1Substituent group, therefore the polarity (dipole moment (dipole moment)) of molecule can be designed
It is nonpolarity to approach, thus the organic light emission member in production electrical adjustment layer containing the compound indicated by above-mentioned chemical formula 1
When part, the formation of the layer of amorphous (amorphous) may be implemented.Therefore, according to the organic of an embodiment of this specification
Raising, lower driving voltage and raising of life characteristic of efficiency etc. may be implemented in light-emitting component.
In particular, the compound indicated by above-mentioned chemical formula 1 only has on a benzene in spiro fluorene xanthene (mother nucleus structure)
Substituted base not only has above-mentioned characteristic electron, also has sterically horizontal structure especially in n=0, m=1, because
, when forming organic matter layer by this substance, electron mobility is reinforced for this.On the contrary, in the mother nucleus structure of chemical formula 12 with
On phenyl ring be substituted when, due to that can not have horizontal structure as described above, the electronics compared with the compound of the present invention
Mobility is low.
In this specification, " energy level " indicates energy size.Therefore, energy level is interpreted to indicate the absolute value of the energy value.
For example, energy level it is low or it is deep refer to become larger from vacuum level to negative direction absolute value.
In this specification, HOMO (highest occupied molecular orbital(HOMO), highest occupied molecular orbital)
Refer to molecular orbital (the highest occupied molecular rail that the highest region of energy is in the region that electronics may participate in combination
Road), LUMO (lowest unocccupied molecular orbital, lowest unoccupied molecular orbital) refers to electronics half
In bond area in minimum energy region molecular orbital (lowest unocccupied molecular orbital), HOMO energy level refer to from
Vacuum level to HOMO distance.In addition, lumo energy refers to the distance from vacuum level to LUMO.
In this specification, band gap (bandgap) refers to the energy level difference of HOMO and LUMO, i.e. HOMO-LUMO energy gap
(Gap)。
Under normal circumstances, in the case where the electrical adjustment layer of organic illuminating element, HOMO energy level it is lower (6.0eV with
On), performance is better, the lumo energy of the more adjacent luminescent layer of lumo energy, and performance is better.(under normal circumstances, blue light-emitting layer
Lumo energy is 2.8eV ± 0.2eV) in addition, in the case where electronic barrier layer, lumo energy is higher, and performance is better, HOMO energy
The performance that grade does not only have too many differences that could expect with the HOMO energy level of luminescent layer.(under normal circumstances, blue light-emitting layer
HOMO energy level is 5.7eV~5.9eV)
According to an embodiment of this specification, the HOMO energy level of the compound indicated by above-mentioned chemical formula 1 can be
More than 6.0eV.
According to an embodiment of this specification, by triplet (triplet) energy for the compound that above-mentioned chemical formula 1 indicates
Grade can be 2.5eV or more.
According to an embodiment of this specification, the band gap (bandgap) of the compound indicated by above-mentioned chemical formula 1 can be with
For 3.0eV or more.
In the case that the compound indicated by chemical formula 1 met the above range is used for electrical adjustment layer, electron transfer
Rate is high, and when being used for organic illuminating element, driving voltage is low, the HOMO energy level with 6.0eV or more, since excellent hole hinders
Gear effect and show the characteristic of high efficiency and long-life.
According to an embodiment of this specification, the HOMO energy level of the compound indicated by above-mentioned chemical formula 3 can be
More than 5.5eV.
According to an embodiment of this specification, the band gap (bandgap) of the compound indicated by above-mentioned chemical formula 3 can be with
For 3.0eV or more.
In the case that the compound indicated by chemical formula 3 met the above range is used for electronic barrier layer, there is 5.5eV
Above HOMO energy level, so that the barrier with luminescent layer reduces, electron mobility is high, when being used for organic illuminating element, display
Driving voltage is low out, characteristic of high efficiency and long-life.
In this specification, HOMO energy level can use photoelectron spectroscopy device under atmospheric conditions (RIK EN KEIKI Co.,
Ltd. it manufactures: AC3) being measured, lumo energy can be to pass through luminescence generated by light (photoluminescence) (PL) measurement
Wavelength value is calculated.
In this specification, when pointing out a certain constituent element of certain a part of "comprising", as long as no especially opposite record,
Then mean that other constituent elements can be further included, rather than other constituent elements are excluded.
It not only include a certain component and another when pointing out that a certain component is located at another component "upper" in this specification
The case where one component contacts, include thes case where that there are other components between two components.
In this specification, the illustration of substituent group is described below, and but not limited to this.
Above-mentioned " substitution " this term refers to that the hydrogen atom in conjunction with the carbon atom of compound is substituted by other substituent groups, quilt
As long as the substituted substituted position of position hydrogen atom, that is, the position that substituent group can replace does not limit then, when substitution 2
When a above, 2 or more substituent groups be can be the same or different from each other.
In this specification, " substituted or unsubstituted " this term refers to by selected from deuterium, halogen group, itrile group, nitro ,-C
(=O) NC (=O) R201,-C (=O) R201,-C (=O) NR201R202,-C (=O) OR201, hydroxyl, alkyl, naphthenic base, alcoxyl
Base, aryloxy group, alkyl sulfenyl, artyl sulfo, alkyl sulphonyl, aryl sulfonyl, alkenyl, silicyl, boryl, amido, virtue
1 or 2 or more substituent group in base phosphino-, oxidation phosphino-, aryl and heterocycle replaces, or is taken by foregoing illustrative
The substituent group that 2 or more the substituent groups of Dai Jizhong are formed by connecting replaces, or does not have any substituent group.Herein, R201With
R202It is same or different to each other, is each independently alkyl, naphthenic base or aryl.For example, " more than two substituent groups are connected
Substituent group " can be xenyl.That is, xenyl can be aryl, the substitution that 2 phenyl are formed by connecting can also be construed to
Base.
In this specification, halogen group can be fluorine, chlorine, bromine or iodine.
In this specification, alkyl can be linear chain or branched chain, and carbon atom number is not particularly limited, but preferably 1 to 30.Tool
For body, preferably carbon atom number is 1 to 20.More specifically, preferably carbon atom number is 1 to 10.As specific example, there is first
Base, ethyl, propyl, n-propyl, isopropyl, butyl, normal-butyl, isobutyl group, tert-butyl, sec-butyl, 1- methyl butyl, 1- ethyl
Butyl, amyl, n-pentyl, isopentyl, neopentyl, tertiary pentyl, hexyl, n-hexyl, 1- methyl amyl, 2- methyl amyl, 3,3-
Dimethylbutyl, 2- ethyl-butyl, heptyl, n-heptyl, 1- methylhexyl, octyl, n-octyl, t-octyl, 1- methylheptyl, 2-
Ethylhexyl, 2- propylpentyl, n-nonyl, 2,2- dimethyl heptyl, 1- ethyl propyl, 1,1- dimethyl propyl, isohesyl, 2-
Methyl amyl, 4- methylhexyl, 5- methylhexyl etc., but not limited to this.
In this specification, naphthenic base is not particularly limited, but preferably carbon atom number is 3 to 30, and more preferable carbon atom number is 3
To 20.Specifically, having cyclopropyl, cyclobutyl, cyclopenta, 3- methylcyclopentyl, 2,3- dimethylcyclopentyl, cyclohexyl, 3-
Methylcyclohexyl, 4- methylcyclohexyl, 2,3- Dimethylcyclohexyl, 3,4,5- trimethylcyclohexyl, 4- tert-butylcyclohexyl, ring
Heptyl, cyclooctyl etc., but not limited to this.
In this specification, alkoxy can be straight chain, branch or ring-type.The carbon atom number of alkoxy is not particularly limited,
But it is preferred that carbon atom number is 1 to 30.Specifically, it is preferable that carbon atom number is 1 to 20.More specifically, preferably carbon atom number is 1
To 10.Specifically, can be methoxyl group, ethyoxyl, positive propoxy, isopropoxy, isopropyl oxygroup, n-butoxy, isobutyl
Oxygroup, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyl oxygen, isoamoxy, positive hexyloxy, 3,3- dimethyl butyrate oxygroup,
2- ethyl-butoxy, n-octyloxy, positive nonyl epoxide, n-decyloxy, benzyloxy, to methylbenzyloxy etc., but not limited to this.
In this specification, amido can be selected from-NH2, alkyl amine group, N- alkylaryl amido, arylamine group, N- aryl it is miscellaneous
Arylamine group, N- miscellaneous alkyl aryl amido and heteroaryl amido, carbon atom number are not particularly limited, but preferably 1 to 30.As
The specific example of amido has methylamino, dimethyl amido, ethyl amido, diethyl amido, phenyl amido, naphthalene amido, connection
Phenyl amido, anthryl amido, 9- methylanthryl amido, diphenyl amido, N- phenyl napthyl amido, dimethylbenzene amido, N- phenyl
Toluene amido, triphenyl amido, N- phenylbiphenylyl amido, N- phenyl napthyl amido, N- xenyl naphthalene amido, N- naphthalene fluorenes
Base amido, N- phenyl phenanthryl amido, N- xenyl phenanthryl amido, N- phenylfluorenyl amido, N- phenyl terphenyl amido, N- are luxuriant and rich with fragrance
Base fluorenyl amido, N- xenyl fluorenyl amido etc., but not limited to this.
In this specification, N- alkylaryl amido refers to the amido for replacing on the N of amido and having alkyl and aryl.
In this specification, N- aryl heteroaryl amido refers to the amido for replacing on the N of amido and having aryl and heteroaryl.
In this specification, N- miscellaneous alkyl aryl amido refers to the amido for replacing on the N of amido and having alkyl and heteroaryl.
In this specification, alkyl amine group, N- aryl alkyl amido, alkyl sulfenyl, alkyl sulphonyl, N- miscellaneous alkyl aryl amine
Alkyl in base is identical as the illustration of above-mentioned alkyl.Specifically, having methylsulfany, ethylsulfanyl, uncle as alkyl sulfenyl
Butyl sulfenyl, hexyl sulfenyl, octylthio etc., as alkyl sulphonyl, have mesyl, ethylsulfonyl, sulfonyl propyl base,
Butyl sulfonyl etc., but not limited to this.
In this specification, alkenyl can be linear chain or branched chain, and carbon atom number is not particularly limited, but preferably 2 to 30.Make
For specific example, there are vinyl, 1- acrylic, isopropenyl, 1- cyclobutenyl, 2- cyclobutenyl, 3- cyclobutenyl, 1- pentenyl, 2-
Pentenyl, 3- pentenyl, 3-methyl-1-butene base, 1,3- butadienyl, allyl, 1- phenylethylene -1- base, 2- phenyl second
Alkene -1- base, 2,2- diphenylethlene -1- base, 2- phenyl -2- (naphthalene -1- base) ethylene -1- base, 2,2- bis- (diphenyl -1- bases)
Ethylene -1- base, Stilbene base, styryl etc., but not limited to this.
In this specification, silicyl can be indicated by the chemical formula of-SiRaRbRc, and above-mentioned Ra, Rb and Rc respectively can be with
For hydrogen, substituted or unsubstituted alkyl or substituted or unsubstituted aryl.Above-mentioned silicyl specifically has trimethyl silyl
Base, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyl-dimethyl monosilane
Base, triphenyl-silyl, diphenylsilyl group, phenyl silyl groups etc., but not limited to this.
In this specification, boryl can be-BR100R101, above-mentioned R100And R101It is same or different to each other, each independently may be used
To be selected from hydrogen, deuterium, halogen group, itrile group, the monocycle of substituted or unsubstituted carbon atom number 3 to 30 or polycyclic naphthenic base, take
The monocycle of the alkyl of linear chain or branched chain of generation or unsubstituted carbon atom number 1 to 30, substituted or unsubstituted carbon atom number 6 to 30
Or monocycle or the polycyclic heteroaryl of polycyclic aryl and substituted or unsubstituted carbon atom number 2 to 30.
In this specification, oxidation phosphino- specifically has diphenyl phosphine oxide base, dinaphthyl oxidation phosphino- etc., but is not limited to
This.
In this specification, aryl is not particularly limited, but preferably carbon atom number be 6 to 30, more preferable carbon atom number be 6 to
20.Above-mentioned aryl can be monocycle or polycyclic.
When above-mentioned aryl is monocyclic aryl, carbon atom number is not particularly limited, but preferably carbon atom number is 6 to 30.Specifically
For, it can be phenyl, xenyl, terphenyl etc., but not limited to this as monocyclic aryl.
When above-mentioned aryl is polyaromatic, carbon atom number is not particularly limited, but preferably carbon atom number is 10 to 30.Specifically
For, as polyaromatic, can for naphthalene, anthryl, phenanthryl, triphenyl, pyrenyl, Fu base, base,Base, fluorenyl etc., but
It's not limited to that.
In this specification, above-mentioned fluorenyl can be substituted, and adjacent group can be bonded to each other and form ring.
When above-mentioned fluorenyl is substituted, Ke Yiwei Deng.But not limited to this.
In this specification, " adjacent " group refers to be replaced on the atom that the atom replaced with the substituent group is directly connected to
Substituent group, with the substituent group in stereochemical structure immediate substituent group or the substituent group replace atom on replace
Other substituent groups.For example, with substituted 2 substituent groups in adjacent position (ortho) and same in aliphatic ring in phenyl ring
2 substituent groups replaced on carbon can be construed to " adjacent " group.
In this specification, aryloxy group, artyl sulfo, aryl sulfonyl, N- aryl alkyl amido, N- aryl heteroaryl amido
It is identical as the illustration of above-mentioned aryl with the aryl in aryl phosphino-.Specifically, having phenoxy group, to toluene as aryloxy group
Oxygroup, toloxyl, 3,5- dimethyl phenoxy, 2,4,6- trimethylbenzene oxygroup, to tert-butyl benzene oxygroup, 3- biphenyl oxygen
Base, 4- biphenylyloxy, 1- naphthoxy, 2- naphthoxy, 4- methyl-1-naphthoxy, 5- methyl-2- naphthoxy, 1- anthracene oxygroup, 2- anthracene
Oxygroup, 9- anthracene oxygroup, 1- phenanthrene oxygroup, 3- phenanthrene oxygroup, 9- phenanthrene oxygroup etc., as artyl sulfo, have phenylsulfartyl, 2- aminomethyl phenyl
Sulfenyl, 4- tert-butyl-phenyl sulfenyl etc., as aryl sulfonyl, there is benzenesulfonyl, p-toluenesulfonyl etc., but be not limited to
This.
It is substituted or unsubstituted monoarylamine base, substituted or unsubstituted as the example of arylamine group in this specification
Diaryl amido.Aryl in above-mentioned arylamine group can be monocyclic aryl, can be polyaromatic.Include 2 or more
The arylamine group of above-mentioned aryl may include monocyclic aryl, polyaromatic, or simultaneously include monocyclic aryl and polyaromatic.Example
Such as, the aryl in above-mentioned arylamine group can be selected from the illustration of above-mentioned aryl.
In this specification, heteroaryl includes 1 or more non-carbon, that is, hetero atom, specifically, above-mentioned hetero atom can be with
Include 1 or more the atom in O, N, Se and S etc..Carbon atom number is not particularly limited, but preferably carbon atom number be 2 to
30, more preferable carbon atom number is 2 to 20, and above-mentioned heteroaryl can be monocycle or polycyclic.As the example of heteroaryl, there is thiophene
Base, furyl, pyrrole radicals, imidazole radicals, thiazolyl,Oxazolyl,Di azoly, pyridyl group, bipyridyl, pyrimidine radicals, triazine
Base, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolyl, quinoxalinyl, phthalazinyl, Pyridopyrimidine base,
Pyrido-pyrazine base, pyrazine and pyrazinyl, isoquinolyl, indyl, carbazyl, benzoOxazolyl, benzimidazolyl, benzo
Thiazolyl, benzo carbazole base, benzothienyl, dibenzothiophene, benzofuranyl, phenanthroline
(phenanthroline), differentOxazolyl, thiadiazolyl group, phenothiazinyl and dibenzofuran group etc., but not limited to this.
In this specification, as the example of heteroaryl amido, substituted or unsubstituted single heteroaryl amido replaces or not
Substituted di (hetero) arylamine group or substituted or unsubstituted three heteroaryls amido.Heteroaryl comprising 2 or more above-mentioned heteroaryls
Base amido may include bicyclic heteroaryl, polyheteroaromatic, or simultaneously include bicyclic heteroaryl and polyheteroaromatic.For example,
Heteroaryl in above-mentioned heteroaryl amido can be selected from the example of above-mentioned heteroaryl.
In this specification, the illustration of N- aryl heteroaryl amido and the heteroaryl in N- miscellaneous alkyl aryl amido is such as above-mentioned
The illustration of heteroaryl.
In this specification, arlydene refers to the group on aryl there are two binding site, i.e. divalent group.They are in addition to dividing
The above-mentioned explanation about aryl Wei not can be applicable in other than divalent group.
In this specification, inferior heteroaryl refers to the group on heteroaryl there are two binding site, i.e. divalent group.They are removed
It is respectively that can be applicable in the above-mentioned explanation about heteroaryl other than divalent group.
In this specification, heterocycle can be monocycle or polycyclic, can be aromatic series, aliphatic or aromatic series and fat
The condensed ring of race can be selected from the illustration of above-mentioned heteroaryl.In addition to this, as the example of heterocycle, have comprising hydrogenated acridine base
(for example,) and sulfonyl heterocycle structure, for example,
Deng.
In this specification, adjacent group is bonded to each other in the substituted or unsubstituted ring to be formed, " ring " refer to substitution or
Unsubstituted hydrocarbon ring or substituted or unsubstituted heterocycle.
In this specification, hydrocarbon ring can be aromatic series, aliphatic or aromatic series and aliphatic condensed ring, on not being
It states other than 1 valence, it can the illustration selected from above-mentioned naphthenic base or aryl.
In this specification, aromatic ring can be selected from above-mentioned aryl other than not being 1 valence for monocycle or polycyclic
Illustration.
In this specification, heterocycle includes 1 or more non-carbon, that is, hetero atom, specifically, above-mentioned hetero atom can wrap
Containing 1 or more the atom in O, N, Se and S etc..Above-mentioned heterocycle can be monocycle or polycyclic, can be aromatic series, fat
Race or aromatic series and aliphatic condensed ring can the illustrations selected from above-mentioned heteroaryl or heterocycle other than not being 1 valence.
According to an embodiment of this specification, in above-mentioned chemical formula 1, L1 is Direct Bonding, arlydene or sub- heteroaryl
Base.
According to an embodiment of this specification, in above-mentioned chemical formula 1, L1 is Direct Bonding, substituted or unsubstituted Asia
Phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted sub- terphenyl, replaces substituted or unsubstituted biphenylene
Or it is unsubstituted sub- tetrad phenyl, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted
Sub- triphenylene, substituted or unsubstituted sub- pyrenyl, substituted or unsubstituted fluorenylidene, substituted or unsubstituted spiro cyclopentane are sub-
Fluorenyl, substituted or unsubstituted sub- dibenzofuran group, the dibenzothiophene of substituted or unsubstituted divalent, substitution do not take
Sub- carbazyl, substituted or unsubstituted sub-pyridyl group, the furyl of substituted or unsubstituted divalent or the substitution in generation do not take
The thienyl of the divalent in generation.
According to an embodiment of this specification, in above-mentioned chemical formula 1, L1 be Direct Bonding, phenylene, biphenylene,
Naphthalene, sub- terphenyl, sub- pyrimidine radicals, the furyl of divalent or the thienyl of divalent.
According to an embodiment of this specification, in above-mentioned chemical formula 1, L1 is for Direct Bonding or by being selected from following structures
An expression in formula.
In above structure,It is the position in conjunction with main chain.
According to an embodiment of this specification, in above-mentioned chemical formula 1, Ar1 be itrile group, substituted or unsubstituted alkyl,
It is substituted or unsubstituted naphthenic base, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy group, substituted or unsubstituted
Alkyl sulfenyl, substituted or unsubstituted artyl sulfo, substituted or unsubstituted alkyl sulphonyl, substituted or unsubstituted aryl sulphur
Acyl group, substituted or unsubstituted amido, substituted or unsubstituted aryl phosphino-, substituted or unsubstituted oxidation phosphino-, replace or
Unsubstituted aryl, the heterocycle of substituted or unsubstituted monocycle, heterocycle more than substituted or unsubstituted tricyclic, replace or
Unsubstituted includes the bicyclic heterocycle of 2 or more N, substituted or unsubstituted isoquinolyl or by selected from above-mentioned chemistry
The structure that any of formula 2 and following chemical formula 6 to 15 indicate.
According to an embodiment of this specification, in above-mentioned chemical formula 1, Ar1 is itrile group, substituted or unsubstituted alcoxyl
Base, substituted or unsubstituted oxidation phosphino-, substituted or unsubstituted silicyl, substituted or unsubstituted aryl, substitution or not
More than the heterocycle of substituted monocycle, substituted or unsubstituted tricyclic heterocycle, it is substituted or unsubstituted include 2 or more N
Bicyclic heterocycle, substituted or unsubstituted isoquinolyl or by be selected from above-mentioned chemical formula 2 and following chemical formula 6 to 15
Any of indicate structure.
According to an embodiment of this specification, in above-mentioned chemical formula 1, Ar1 is itrile group, substituted or unsubstituted alcoxyl
Base, substituted or unsubstituted oxidation phosphino-, substituted or unsubstituted aryl or by be selected from above-mentioned chemical formula 2 and following chemical formula 6
The structure indicated to any of 15.
According to an embodiment of this specification, in above-mentioned chemical formula 1, Ar1 is itrile group, is replaced or do not taken by halogen group
The alkoxy in generation, be substituted with aryl or unsubstituted oxidation phosphino-, by the substituted or unsubstituted aryl of itrile group or by selected from above-mentioned
The structure that any of chemical formula 2 and following chemical formula 6 to 15 indicate.
According to an embodiment of this specification, in above-mentioned chemical formula 1, Ar1 is itrile group；By fluorine-based substituted methoxyl group；
By phenyl, terphenyl or naphthyl substituted or unsubstituted oxidation phosphino-；By the substituted or unsubstituted phenyl of itrile group；By itrile group
Substituted or unsubstituted terphenyl；Or the knot by being indicated selected from any of above-mentioned chemical formula 2 and following chemical formula 6 to 15
Structure.
According to an embodiment of this specification, in above-mentioned chemical formula 1, Ar1 can be indicated by following chemical formula 1a.
[chemical formula 1a]
In above-mentioned chemical formula 1a,
G2 to the position that any of G4, R12 and R13 are in conjunction with the L1 of above-mentioned chemical formula 1, remaining it is mutually the same or
Difference is each independently hydrogen, deuterium, itrile group, nitro, hydroxyl ,-C (=O) NC (=O) R ,-C (=O) R ,-C (=O) NRR' ,-C
(=O) OR, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted alkoxy, substitution or not
Substituted aryloxy group, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted artyl sulfo, substituted or unsubstituted alkyl
Sulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silicyl, takes substituted or unsubstituted aryl sulfonyl
Generation or unsubstituted boryl, substituted or unsubstituted amido, substituted or unsubstituted aryl phosphino-, substituted or unsubstituted oxidation
Phosphino-, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, R and R' are same or different to each other, respectively independent
Ground is alkyl, naphthenic base or aryl.
According to an embodiment of this specification, in above-mentioned chemical formula 1, Ar1 is by being selected from above-mentioned chemical formula 2 and following chemistry
Any of formula 6 to 15 indicates.
[chemical formula 6]
[chemical formula 7]
[chemical formula 8]
[chemical formula 9]
[chemical formula 10]
[chemical formula 11]
[chemical formula 12]
[chemical formula 13]
[chemical formula 14]
[chemical formula 15]
In above-mentioned chemical formula 6 to 15,
X1 be N or CR11, X2 be N or CR12, X3 be N or CR13, X4 be N or CR14, X5 be N or CR15, X6 be N or
CR16, X7 are N or CR17, and X8 is N or CR18, and X9 is N or CR19, and X10 is N or CR20,
X1 into X3 at least two be N, at least one of X4 to X7 be N,
Y1 be O, S, NQ1 or CQ2Q3, Y2 O, S, NQ4 or CQ5Q6, Y3 O, S or NQ7,
Any of G2 to G4 and R11 to R13；Any of G5 to G8；Any of G9 to G15；G16 is extremely
Any of G21；Any of G22 to G27；Any of G28 to G33 and R14 to R17；G34 appointing into G42
One；Any of G43 to G47；Any of G48, G49, R18 and R19；And any of G50 to G61 be with
The position that the L1 of above-mentioned chemical formula 1 is combined,
Remaining position other than the position in conjunction with the L1 of above-mentioned chemical formula 1 into R19 G2 to G61 and R11,
R20 and Q1 to Q7 is same or different to each other, and is each independently hydrogen, deuterium, itrile group, nitro, hydroxyl ,-C (=O) NC (=O)
R ,-C (=O) R ,-C (=O) NRR' ,-C (=O) OR, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substitution
Or unsubstituted alkoxy, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted virtue
Base sulfenyl, substituted or unsubstituted alkyl sulphonyl, substituted or unsubstituted aryl sulfonyl, substituted or unsubstituted alkenyl,
Substituted or unsubstituted silicyl, substituted or unsubstituted boryl, substituted or unsubstituted amido, substituted or unsubstituted virtue
Base phosphino-, substituted or unsubstituted oxidation phosphino-, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, R and
R' is same or different to each other, and is each independently alkyl, naphthenic base or aryl.
According to another embodiment of this specification, in above-mentioned chemical formula 2, G1 is hydrogen or aryl.
According to another embodiment of this specification, in above-mentioned chemical formula 2, G1 is hydrogen or phenyl.
According to another embodiment of this specification, above-mentioned chemical formula 2 is by the appointing into 2-4 selected from following chemical formula 2-1
One expression.
[chemical formula 2-1]
[chemical formula 2-2]
[chemical formula 2-3]
[chemical formula 2-4]
For above-mentioned chemical formula 2-1 into 2-4, the definition of G1 and g1 are identical as above-mentioned chemical formula 2, and * is and above-mentioned chemical formula 1
The position that L1 is combined.
According to another embodiment of this specification, in above-mentioned chemical formula 6, any of G2 to G4 and R11 to R13 are
Position in conjunction with the L1 of above-mentioned chemical formula 1, remaining is same or different to each other, and is each independently hydrogen, substituted or unsubstituted
Aryl or substituted or unsubstituted heteroaryl.
According to another embodiment of this specification, in above-mentioned chemical formula 6, any of G2 to G4 and R11 to R13 are
Position in conjunction with the L1 of above-mentioned chemical formula 1, remaining is same or different to each other, and is each independently hydrogen；By by itrile group, aryl,
Alkyl-substituted heterocycle is substituted with aryl or the substituted or unsubstituted aryl of unsubstituted heterocycle；Or heteroaryl.
According to another embodiment of this specification, in above-mentioned chemical formula 6, any of G2 to G4 and R11 to R13 are
Position in conjunction with the L1 of above-mentioned chemical formula 1, remaining is same or different to each other, and is each independently hydrogen；By being taken by aryl, alkyl
The heterocycle in generation is substituted with aryl or the substituted or unsubstituted phenyl of unsubstituted heterocycle；Replaced by itrile group or heterocycle
Or unsubstituted xenyl；Terphenyl；It is optionally substituted aryl or heteroaryl or unsubstituted naphthalene；It is substituted or unsubstituted by alkyl
Fluorenyl；Triphenylene；Phenanthryl；Fu base；Pyridyl group；Dibenzofuran group；Or dibenzothiophene.
According to another embodiment of this specification, in above-mentioned chemical formula 6, any of G2 to G4 and R11 to R13 are
Position in conjunction with the L1 of above-mentioned chemical formula 1, remaining is same or different to each other, and is each independently hydrogen；By phenyl, terphenyl
Base, carbazyl, quinolyl, phenoPiperazine base, phenothiazinyl, triphenylene, fluoranthene base, pyridyl group, dibenzothiophene, hexichol
And furyl, benzo carbazole base, the dihydrophenazine base being substituted by phenyl or is replaced or do not taken by methyl substituted acridan base
The phenyl in generation；Itrile group；Or by the substituted or unsubstituted xenyl of carbazyl；Terphenyl；By phenyl, pyridyl group or dibenzo
The substituted or unsubstituted naphthalene of furyl；By the substituted or unsubstituted fluorenyl of methyl；Triphenylene；Phenanthryl；Fu base；Pyridyl group；
Dibenzofuran group；Or dibenzothiophene.
According to another embodiment of this specification, above-mentioned chemical formula 6 can be indicated by following chemical formula 6a or 6b.
[chemical formula 6a]
[chemical formula 6b]
In above-mentioned chemical formula 6a and 6b, the definition of G2 to G4 and R13 are identical as the definition in above-mentioned chemical formula 6.
According to an embodiment of this specification, in chemical formula 6, X1 into X3 at least two be N when, HOMO energy
It is deep to 6.1eV or more, successfully plays the effect as electrical adjustment layer, electron mobility is high, for organic light emission member
When part, low driving voltage, high efficiency and the element of long-life may be constructed.Specifically, when above-mentioned Ar1 is by chemical formula 6a or change
When formula 6b is indicated, above-mentioned effect is maximized.
In particular, HOMO energy is deep to 6.1eV or more when above-mentioned Ar1 is the triazine radical of chemical formula 6b, smoothly plays and make
For the effect of electrical adjustment layer, electron mobility is high, when for organic illuminating element, shows that driving voltage is low, efficient
The characteristic of rate and long-life.
According to another embodiment of this specification, in above-mentioned chemical formula 7, any of G5 to G8 is and above-mentioned chemistry
The position that the L1 of formula 1 is combined, remaining is same or different to each other, and is each independently hydrogen or substituted or unsubstituted aryl.
According to another embodiment of this specification, in above-mentioned chemical formula 7, any of G5 to G8 is and above-mentioned chemistry
The position that the L1 of formula 1 is combined, remaining is same or different to each other, and is each independently hydrogen or aryl.
According to another embodiment of this specification, in above-mentioned chemical formula 7, any of G5 to G8 is and above-mentioned chemistry
The position that the L1 of formula 1 is combined, remaining is same or different to each other, and is each independently hydrogen, phenyl or naphthalene.
According to another embodiment of this specification, in above-mentioned chemical formula 8, any of G9 to G15 is and above-mentionedization
The position that the L1 of formula 1 is combined, remaining is same or different to each other, and is each independently hydrogen or substituted or unsubstituted aryl.
According to another embodiment of this specification, in above-mentioned chemical formula 8, any of G9 to G15 is and above-mentionedization
The position that the L1 of formula 1 is combined, remaining is same or different to each other, and is each independently hydrogen or aryl.
According to another embodiment of this specification, in above-mentioned chemical formula 8, any of G9 to G15 is and above-mentionedization
The position that the L1 of formula 1 is combined, remaining is same or different to each other, and is each independently hydrogen or phenyl.
According to another embodiment of this specification, in above-mentioned chemical formula 9, any of G16 to G21 is and above-mentionedization
The position that the L1 of formula 1 is combined, remaining is same or different to each other, and is each independently hydrogen or substituted or unsubstituted aryl.
According to another embodiment of this specification, in above-mentioned chemical formula 9, any of G16 to G21 is and above-mentionedization
The position that the L1 of formula 1 is combined, remaining is same or different to each other, and is each independently hydrogen or aryl.
According to another embodiment of this specification, in above-mentioned chemical formula 9, any of G16 to G21 is and above-mentionedization
The position that the L1 of formula 1 is combined, remaining is same or different to each other, and is each independently hydrogen, phenyl, xenyl or naphthalene.
According to another embodiment of this specification, in above-mentioned chemical formula 10, any of G22 to G27 be with it is above-mentioned
The position that the L1 of chemical formula 1 is combined, remaining is same or different to each other, and is each independently hydrogen or aryl.
According to another embodiment of this specification, in above-mentioned chemical formula 10, any of G22 to G27 be with it is above-mentioned
The position that the L1 of chemical formula 1 is combined, remaining is same or different to each other, and is each independently hydrogen or phenyl.
According to another embodiment of this specification, in above-mentioned chemical formula 11, any of G28 to G33 and R14 into R17
A position in conjunction with the L1 of above-mentioned chemical formula 1, remaining is same or different to each other, and is each independently hydrogen.
According to another embodiment of this specification, above-mentioned chemical formula 11 by selected from following chemical formula 11-1 into 11-8
Any one is indicated.
[chemical formula 11-1]
[chemical formula 11-2]
[chemical formula 11-3]
[chemical formula 11-4]
[chemical formula 11-5]
[chemical formula 11-6]
[chemical formula 11-7]
[chemical formula 11-8]
Above-mentioned chemical formula 11-1 is into 11-8, definition and the definition in above-mentioned chemical formula 11 of G28 to G33 and R14 to R17
It is identical.
According to another embodiment of this specification, in above-mentioned chemical formula 12, any of G34 to G42 be with it is above-mentioned
The position that the L1 of chemical formula 1 is combined, remaining and Q1 to Q3 are same or different to each other, and are each independently hydrogen.
According to another embodiment of this specification, in above-mentioned chemical formula 13, any of G43 to G47 be with it is above-mentioned
The position that the L1 of chemical formula 1 is combined, remaining and Q4 to Q6 are same or different to each other, and are each independently hydrogen, replace or do not take
The alkyl in generation or substituted or unsubstituted aryl.
According to another embodiment of this specification, in above-mentioned chemical formula 13, any of G43 to G47 be with it is above-mentioned
The position that the L1 of chemical formula 1 is combined, remaining and Q4 to Q6 are same or different to each other, and are each independently hydrogen, alkyl or virtue
Base.
According to another embodiment of this specification, in above-mentioned chemical formula 13, any of G43 to G47 be with it is above-mentioned
The position that the L1 of chemical formula 1 is combined, remaining and Q4 to Q6 are same or different to each other, and are each independently hydrogen, methyl or benzene
Base.
According to another embodiment of this specification, in above-mentioned chemical formula 13, when Y2 is NQ4, above-mentioned G43 and Q4 are tied each other
Conjunction forms substituted or unsubstituted ring.
According to another embodiment of this specification, in above-mentioned chemical formula 13, when Y2 is NQ4, above-mentioned G43 and Q4 are tied each other
Conjunction forms substituted or unsubstituted heterocycle.
According to another embodiment of this specification, above-mentioned chemical formula 13 by selected from following chemical formula 13-1 into 13-4
Any one is indicated.
[chemical formula 13-1]
[chemical formula 13-2]
[chemical formula 13-3]
[chemical formula 13-4]
For above-mentioned chemical formula 13-1 into 13-4, any of G43 to G47 is the portion in conjunction with the L1 of above-mentioned chemical formula 1
Position, remaining and Q4 to Q6 be same or different to each other, be each independently hydrogen, deuterium, itrile group, nitro, hydroxyl ,-C (=O) NC (=
O) R ,-C (=O) R ,-C (=O) NRR' ,-C (=O) OR, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, take
It is generation or unsubstituted alkoxy, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted
Artyl sulfo, substituted or unsubstituted alkyl sulphonyl, substituted or unsubstituted aryl sulfonyl, substituted or unsubstituted alkene
It is base, substituted or unsubstituted silicyl, substituted or unsubstituted boryl, substituted or unsubstituted amido, substituted or unsubstituted
Aryl phosphino-, substituted or unsubstituted oxidation phosphino-, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl
Base, R and R' are same or different to each other, and are each independently alkyl, naphthenic base or aryl.
According to another embodiment of this specification, in above-mentioned chemical formula 14, any of G48, G49, R18 and R19
For the position in conjunction with the L1 of above-mentioned chemical formula 1, remaining and Q7 are same or different to each other, and are each independently hydrogen or take
Generation or unsubstituted aryl.
According to another embodiment of this specification, in above-mentioned chemical formula 14, any of G48, G49, R18 and R19
For the position in conjunction with the L1 of above-mentioned chemical formula 1, remaining and Q7 are same or different to each other, and are each independently hydrogen or aryl.
According to another embodiment of this specification, in above-mentioned chemical formula 14, any of G48, G49, R18 and R19
For the position in conjunction with the L1 of above-mentioned chemical formula 1, remaining and Q7 are same or different to each other, and are each independently hydrogen or phenyl.
According to another embodiment of this specification, above-mentioned chemical formula 14 by selected from following chemical formula 14-1 into 14-9
Any one is indicated.
[chemical formula 14-1]
[chemical formula 14-2]
[chemical formula 14-3]
[chemical formula 14-4]
[chemical formula 14-5]
[chemical formula 14-6]
[chemical formula 14-7]
[chemical formula 14-8]
[chemical formula 14-9]
Above-mentioned chemical formula 14-1 into 14-9, determine with above-mentioned chemical formula 14 by the definition of G48, G49, R18, R19 and Q7
Justice is identical.
According to an embodiment of this specification, in above-mentioned chemical formula 15, above-mentioned G50 into G61 in addition to above-mentionedization
Remaining position and R20 other than the position that formula 1 combines are same or different to each other, and are each independently hydrogen, replace or do not take
The aryl in generation or substituted or unsubstituted heteroaryl.
According to an embodiment of this specification, in above-mentioned chemical formula 15, above-mentioned G50 into G61 in addition to above-mentionedization
Formula 1 combine position other than remaining position and R20 be same or different to each other, be each independently hydrogen or substitution or
Unsubstituted aryl.
According to an embodiment of this specification, in above-mentioned chemical formula 15, above-mentioned G50 into G61 in addition to above-mentionedization
Remaining position and R20 other than the position that formula 1 combines are same or different to each other, and are each independently hydrogen or phenyl.
In one embodiment of this specification, in above-mentioned chemical formula 15, above-mentioned G50 into G61 in addition to above-mentioned chemistry
Remaining position and R20 other than the position that formula 1 combines are same or different to each other, and are each independently hydrogen.
According to an embodiment of this specification, the integer that above-mentioned m is 1.
According to an embodiment of this specification, above-mentioned chemical formula 1 is by any selected from following chemical formula 1-1 into 1-4
A expression.
[chemical formula 1-1]
[chemical formula 1-2]
[chemical formula 1-3]
[chemical formula 1-4]
Above-mentioned chemical formula 1-1 into 1-4,
The definition of L1, Ar1, R1 and n are identical as above-mentioned chemical formula 1.
According to an embodiment of this specification, above-mentioned R1 is hydrogen.
Under normal circumstances, the electron mobility of compound is according to the orientation (orientation) in the 3D structure of molecule
And it is different, when being more horizontal structure (horizontal structure), electron mobility is reinforced.According to this specification
The substitution of one embodiment has the compound of 1-L1-Ar1 indicated by chemical formula 1 and substitution to have the compound of 2-L1-Ar1
It compares, the horizontal structure tendency of molecule is stronger, has the advantages that electron mobility is got higher.It will indicate miscellaneous by chemical formula 1 as a result,
When cycle compound is used for organic illuminating element, have the effect of low driving voltage, high efficiency and long-life.(referring to APPLIED
PHYSICS LETTERS 95,243303(2009))
It, can be with according to Figure 10 and Figure 11 of the 3D structure of the compound E9 and E18 of the embodiment for showing this specification
Confirm that the molecule of above compound has horizontal structure, according to the compound for showing the comparative example compound as this specification
A axis and B axle can be confirmed almost at vertical in Figure 12 and Figure 13 of the 3D structure of ET-1-E and ET-1-I respectively, and molecule is significantly inclined
From horizontal structure.As a result it is found that according to the compound E9 and E18 of an embodiment of this specification and compound ET-1-E and
ET-1-I is compared, and is had horizontal structure due to the orientation difference in the 3D structure of molecule, will be indicated as a result, by chemical formula 1
Compound be used for organic illuminating element when, have the effect of in driving voltage, efficiency and in terms of the service life excellent.
According to an embodiment of this specification, above-mentioned chemical formula 1 can be by any one table in following compounds
Show.
According to an embodiment of this specification, above-mentioned L'1 to L'3 is same or different to each other, and is each independently directly
The Asia of bonding, the arlydene of substituted or unsubstituted carbon atom number 6 to 30 or substituted or unsubstituted carbon atom number 2 to 30
Heteroaryl.
According to an embodiment of this specification, above-mentioned L'1 to L'3 is same or different to each other, and is each independently directly
The Asia of bonding, the arlydene of substituted or unsubstituted carbon atom number 6 to 20 or substituted or unsubstituted carbon atom number 2 to 20
Heteroaryl,
According to an embodiment of this specification, above-mentioned L'1 to L'3 is same or different to each other, and is each independently directly
Bonding, substituted or unsubstituted sub- terphenyl, takes substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene
Generation or unsubstituted naphthalene or substituted or unsubstituted fluorenylidene.
According to an embodiment of this specification, above-mentioned L'1 to L'3 is same or different to each other, and is each independently directly
Bonding, phenylene, biphenylene, sub- terphenyl, naphthalene or by the substituted or unsubstituted fluorenylidene of methyl.
According to an embodiment of this specification, above-mentioned L'1 to L'3 is same or different to each other, and is each independently directly
Bonding, phenylene, biphenylene or sub- terphenyl.
According to an embodiment of this specification, above-mentioned Ar'1 to Ar'3 is same or different to each other, be each independently hydrogen,
The heteroaryl of the aryl of substituted or unsubstituted carbon atom number 6 to 30 or substituted or unsubstituted carbon atom number 2 to 30, or
Person is indicated that at least one of Ar'1 to Ar'3 is indicated by above-mentioned chemical formula 4 by above-mentioned chemical formula 4 or 5.
According to an embodiment of this specification, above-mentioned Ar'1 to Ar'3 is same or different to each other, be each independently hydrogen,
The heteroaryl of the aryl of substituted or unsubstituted carbon atom number 6 to 20 or substituted or unsubstituted carbon atom number 2 to 20, or
Person is indicated that at least one of Ar'1 to Ar'3 is indicated by above-mentioned chemical formula 4 by above-mentioned chemical formula 4 or 5.
According to an embodiment of this specification, above-mentioned Ar'1 to Ar'3 is same or different to each other, is each independently and takes
The heteroaryl of the aryl or substituted or unsubstituted carbon atom number 2 to 30 of generation or unsubstituted carbon atom number 6 to 30, or
It is indicated by above-mentioned chemical formula 4 or 5, at least one of Ar'1 to Ar'3 is indicated by above-mentioned chemical formula 4.
According to an embodiment of this specification, above-mentioned Ar'1 to Ar'3 is same or different to each other, is each independently and takes
The heteroaryl of the aryl or substituted or unsubstituted carbon atom number 2 to 20 of generation or unsubstituted carbon atom number 6 to 20, or
It is indicated by above-mentioned chemical formula 4 or 5, at least one of Ar'1 to Ar'3 is indicated by above-mentioned chemical formula 4.
According to an embodiment of this specification, above-mentioned Ar'1 to Ar'3 is same or different to each other, be each independently hydrogen,
Substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, or indicate that Ar'1 is extremely by above-mentioned chemical formula 4 or 5
At least one of Ar'3 is indicated that at least one of Ar'1 to Ar'3 is indicated by above-mentioned chemical formula 5 by above-mentioned chemical formula 4.
According to an embodiment of this specification, above-mentioned Ar'1 to Ar'3 is same or different to each other, be each independently hydrogen,
The heteroaryl of the aryl of substituted or unsubstituted carbon atom number 6 to 30 or substituted or unsubstituted carbon atom number 2 to 30, or
Person is indicated that at least one of Ar'1 to Ar'3 indicates that Ar'1 is into Ar'3 by above-mentioned chemical formula 4 by above-mentioned chemical formula 4 or 5
At least one is indicated by above-mentioned chemical formula 5.
According to an embodiment of this specification, above-mentioned Ar'1 to Ar'3 is same or different to each other, be each independently hydrogen,
The heteroaryl of the aryl of substituted or unsubstituted carbon atom number 6 to 20 or substituted or unsubstituted carbon atom number 2 to 20, or
Person is indicated that at least one of Ar'1 to Ar'3 indicates that Ar'1 is into Ar'3 by above-mentioned chemical formula 4 by above-mentioned chemical formula 4 or 5
At least one is indicated by above-mentioned chemical formula 5.
According to an embodiment of this specification, above-mentioned Ar'1 to Ar'3 is same or different to each other, is each independently and takes
Generation or unsubstituted aryl or substituted or unsubstituted heteroaryl, or indicated by above-mentioned chemical formula 4 or 5, Ar'1 to Ar'3
At least one of indicated by above-mentioned chemical formula 4, at least one of Ar'1 to Ar'3 is indicated by above-mentioned chemical formula 5.
According to an embodiment of this specification, at least one of above-mentioned Ar'1 to Ar'3 is indicated by above-mentioned chemical formula 4,
At least one of Ar'1 to Ar'3 is indicated that remaining is substituted or unsubstituted aryl by above-mentioned chemical formula 5.
According to an embodiment of this specification, at least one of above-mentioned Ar'1 to Ar'3 is indicated by above-mentioned chemical formula 4,
At least one of Ar'1 to Ar'3 is indicated that remaining is the virtue of substituted or unsubstituted carbon atom number 6 to 30 by above-mentioned chemical formula 5
Base.
According to an embodiment of this specification, at least one of above-mentioned Ar'1 to Ar'3 is indicated by above-mentioned chemical formula 4,
At least one of Ar'1 to Ar'3 is indicated that remaining is the virtue of substituted or unsubstituted carbon atom number 6 to 20 by above-mentioned chemical formula 5
Base.
According to an embodiment of this specification, at least one of above-mentioned Ar'1 to Ar'3 is indicated by above-mentioned chemical formula 4,
At least one of Ar'1 to Ar'3 indicates that remaining is aryl by above-mentioned chemical formula 5.
According to an embodiment of this specification, at least one of above-mentioned Ar'1 to Ar'3 is indicated by above-mentioned chemical formula 4,
At least one of Ar'1 to Ar'3 indicates by above-mentioned chemical formula 5, remaining is substituted or unsubstituted phenyl, substituted or unsubstituted
Xenyl, substituted or unsubstituted terphenyl or substituted or unsubstituted fluorenyl.
According to an embodiment of this specification, at least one of above-mentioned Ar'1 to Ar'3 is indicated by above-mentioned chemical formula 4,
At least one of Ar'1 to Ar'3 indicates by above-mentioned chemical formula 5, remaining is phenyl, xenyl, terphenyl or by alkyl
Substituted or unsubstituted fluorenyl.
According to an embodiment of this specification, above-mentioned R'1 into R'9 in addition to the L'1 to L'3 with above-mentioned chemical formula 3
In one combination part other than rest part and R'10 to R'21 be each independently hydrogen.
According to an embodiment of this specification, above-mentioned chemical formula 3 can be by any one table in following compounds
Show.
According to an embodiment of this specification, above-mentioned organic matter layer can also be comprising passing selected from hole injection layer, hole
The organic matter layer of one or more of defeated layer, electron transfer layer and electron injecting layer.
In one embodiment of this specification, above-mentioned electron transfer layer, electron injecting layer or carry out simultaneously electron injection and
The layer of electron-transport can also include n-type dopant.
According to the organic illuminating element of an embodiment of this specification, it includes: it anode, cathode and provides upper
The luminescent layer between anode and above-mentioned cathode is stated, also includes: being provided between above-mentioned luminescent layer and above-mentioned cathode and containing by upper
State chemical formula 1 expression compound electrical adjustment layer and provide between above-mentioned luminescent layer and above-mentioned anode and containing by
The electronic barrier layer for the compound that above-mentioned chemical formula 3 indicates in addition to this can also be comprising infusing selected from hole transmission layer, hole
Enter the organic matter layer of one or more of layer, electron transfer layer and electron injecting layer.But the structure of organic illuminating element is not
It is defined in this, can also include less or more layer of organic matter layer.
According to the organic illuminating element of an embodiment of this specification, it includes: it anode, cathode and provides upper
The luminescent layer between anode and above-mentioned cathode is stated, also includes: being provided between above-mentioned luminescent layer and above-mentioned cathode and containing by upper
State chemical formula 1 expression compound electrical adjustment layer and provide between above-mentioned luminescent layer and above-mentioned anode and containing by
The electronic barrier layer for the compound that above-mentioned chemical formula 3 indicates, comprising being passed selected from electronics between above-mentioned luminescent layer and above-mentioned cathode
The organic matter layer of one or more of defeated layer and electron injecting layer can also include choosing between above-mentioned luminescent layer and above-mentioned anode
From the organic matter layer of one or more of hole transmission layer and hole injection layer.But the structure of organic illuminating element does not limit
It can also include less or more layer of organic matter layer in this.
According to the organic illuminating element of an embodiment of this specification, it includes: it anode, cathode and provides upper
The luminescent layer between anode and above-mentioned cathode is stated, also includes: being provided between above-mentioned luminescent layer and above-mentioned cathode and containing by upper
State chemical formula 1 expression compound electrical adjustment layer and provide between above-mentioned luminescent layer and above-mentioned anode and containing by
The electronic barrier layer for the compound that above-mentioned chemical formula 3 indicates, may include offer above-mentioned cathode and above-mentioned electrical adjustment layer it
Between electron transfer layer, above-mentioned electron transfer layer can also include n-type dopant substance, at this moment be used for electron transfer layer substance
Can be 1:100 to 100:1 with the weight ratio of n-type dopant substance, specifically, can be 1:10 to 10:1, it is more specific and
Speech, can be 1:1.At this moment, n-type dopant substance can be LiQ, and but not limited to this.
According to the organic illuminating element of an embodiment of this specification, it includes: it anode, cathode and provides upper
The luminescent layer between anode and above-mentioned cathode is stated, also includes: being provided between above-mentioned luminescent layer and above-mentioned cathode and containing by upper
State chemical formula 1 expression compound electrical adjustment layer and provide between above-mentioned luminescent layer and above-mentioned anode and containing by
The electronic barrier layer for the compound that above-mentioned chemical formula 3 indicates, can also be comprising providing in above-mentioned anode and above-mentioned electronic barrier layer
Between hole transmission layer.But it's not limited to that for the structure of organic illuminating element, may include less or more layer has
Machine nitride layer.
According to the organic illuminating element of an embodiment of this specification, it includes: it anode, cathode and provides upper
The luminescent layer between anode and above-mentioned cathode is stated, also includes: being provided between above-mentioned luminescent layer and above-mentioned cathode and containing by upper
State chemical formula 1 expression compound electrical adjustment layer and provide between above-mentioned luminescent layer and above-mentioned anode and containing by
The electronic barrier layer for the compound that above-mentioned chemical formula 3 indicates, can also be comprising providing in above-mentioned anode and above-mentioned electronic barrier layer
Between hole injection layer.But it's not limited to that for the structure of organic illuminating element, may include less or more layer has
Machine nitride layer.
According to the organic illuminating element of an embodiment of this specification, it includes: it anode, cathode and provides upper
The luminescent layer between anode and above-mentioned cathode is stated, also includes: being provided between above-mentioned luminescent layer and above-mentioned cathode and containing by upper
State chemical formula 1 expression compound electrical adjustment layer and provide between above-mentioned luminescent layer and above-mentioned anode and containing by
The electronic barrier layer for the compound that above-mentioned chemical formula 3 indicates, also comprising providing between above-mentioned anode and above-mentioned electronic barrier layer
Hole transmission layer, can also be comprising providing hole injection layer between above-mentioned anode and above-mentioned hole transmission layer.But have
It's not limited to that for the structure of machine light-emitting component, may include less or more layer of organic matter layer.
According to the organic illuminating element of an embodiment of this specification, it includes: it anode, cathode and provides upper
It states between anode and above-mentioned cathode and the luminescent layer containing main substance and dopant species, also includes: providing and shine above-mentioned
Between layer and above-mentioned cathode and the electrical adjustment layer containing the compound indicated by above-mentioned chemical formula 1 and offer are in above-mentioned hair
Between photosphere and above-mentioned anode and containing the electronic barrier layer of compound indicated by above-mentioned chemical formula 3, also comprising providing upper
It states between cathode and above-mentioned electrical adjustment layer and the electron transfer layer containing n-type dopant substance, also comprising providing in above-mentioned sun
Hole transmission layer between pole and above-mentioned electronic barrier layer, can also comprising provide above-mentioned anode and above-mentioned hole transmission layer it
Between hole injection layer.But it's not limited to that for the structure of organic illuminating element, can also have comprising less or more layer
Machine nitride layer.
According to an embodiment of this specification, the organic matter layer of the organic illuminating element of this specification can be by single layer knot
It is configured to, can also be formed by the multilayered structure for being laminated with two layers or more of organic matter layer.For example, the organic light emission of this specification
The structure of element can have structure as shown in Figure 1 to Figure 3, but be not limited only to this.
Fig. 1 is instantiated is sequentially laminated with having for anode 30, luminescent layer 40, electron transfer layer 80 and cathode 50 on the base plate 20
The structure of machine light-emitting component 10.Above-mentioned Fig. 1 be according to the exemplary configuration of the organic illuminating element of an embodiment of this specification,
It can also include other organic matter layers.
Fig. 2 is instantiated is sequentially laminated with anode 30, hole injection layer 60, hole transmission layer 70, luminescent layer on the base plate 20
40, the structure of the organic illuminating element 11 of electron transfer layer 80, electron injecting layer 90 and cathode 50.Above-mentioned Fig. 2 is according to this theory
The exemplary configuration of the embodiment of bright book can also include other organic matter layers.
Fig. 3 is instantiated is sequentially laminated with anode 30, hole injection layer 60, hole transmission layer 70, electronics resistance on the base plate 20
The organic light emission member of barrier 101, luminescent layer 40, electrical adjustment layer 100, electron transfer layer 80, electron injecting layer 90 and cathode 50
The structure of part 12.Above-mentioned Fig. 3 is according to the exemplary configuration of the embodiment of this specification, can also include other organic matter layers.
In one embodiment of this specification, above-mentioned n-type dopant can be metal complex etc., and alkali gold can be used
Belong to, such as Li, Na, K, Rb, Cs or Fr；Alkaline-earth metal, such as Be, Mg, Ca, Sr, Ba or Ra；Rare earth metal, such as La, Ce,
Pr, Nd, Sm, Eu, Tb, Th, Dy, Ho, Er, Em, Gd, Yb, Lu, Y or Mn；Or the gold comprising one or more of above-mentioned metal
The metallic compound of category, is not limited to above-mentioned substance, and well known substance in the technical field can be used.
The organic illuminating element of this specification is in addition to above-mentionedization that one layer or more in organic matter layer includes by this specification
Other than compound that formula 1 indicates or the compound indicated by above-mentioned chemical formula 3, well known material in the technical field can use
Material and method are manufactured.
When above-mentioned organic illuminating element includes multiple organic matter layers, above-mentioned organic matter layer can by identical substance or not
Same substance is formed.
For example, the organic illuminating element of this specification can be by stacking gradually anode, organic matter layer and yin on substrate
Pole and manufacture.At this moment, it can manufacture as follows: utilize sputtering (sputtering) or electron beam evaporation method (e-beam
) etc evaporation gold is deposited in physical vapor deposition method (PVD:physical Vapor Deposition) on substrate
Belong to or conductive metal oxide or their alloy and form anode, then formed on the anode and infused comprising hole
The organic matter layer for entering layer, hole transmission layer, luminescent layer, electrical adjustment layer and electron transfer layer, later on the organic matter layer
Vapor deposition can be used as the substance of cathode and manufacture.Other than this method, can also on substrate successively evaporation cathode substance, have
Machine nitride layer, anode material and manufacture organic illuminating element.In addition, being made by the compound that above-mentioned chemical formula 1 or chemical formula 3 indicate
It not only can use vacuum vapour deposition when making organic illuminating element, organic matter layer can also be formed using solution coating method.This
In, so-called solution coating method refers to, spin-coating method, dip coating, knife coating, ink jet printing method, silk screen print method, spray-on process, roller coating
Method etc., but it is not limited only to this.
As above-mentioned anode material, generally for enabling hole successfully to inject to organic matter layer, preferably work function
Big substance.As the concrete example of anode material for use in the present invention, there are the metals such as vanadium, chromium, copper, zinc, gold or their conjunction
Gold；The metal oxides such as zinc oxide, indium oxide, tin indium oxide (ITO), indium zinc oxide (IZO)；ZnO:Al or SnO2: the gold such as Sb
Belong to the combination with oxide；Poly- (3 methyl thiophene), poly- [3,4- (ethylidene -1,2- dioxy) thiophene] (PEDOT), polypyrrole and
Electroconductive polymers such as polyaniline etc., but it is not limited only to this.
As above-mentioned cathode substance, generally for electronics is injected easily to organic matter layer, preferably work function is small
Substance.As the concrete example of above-mentioned cathode substance, there are the metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminium, silver, tin and lead
Or their alloy；LiF/Al or LiO2Multilayered structures substance such as/Al, Mg/Ag etc., but it is not limited only to this.
Above-mentioned hole injection layer is the layer in the hole that injection carrys out self-electrode, as hole injecting material, preferably followingization
It closes object: having the ability of transporting holes, there is hole injection effect from anode, for the excellent of luminescent layer or luminescent material
Hole inject effect, prevent in luminescent layer generated exciton to migrate to electron injecting layer or electron injection material, and thin
Film Forming ability is excellent.It is preferred that HOMO (highest occupied molecular orbital(HOMO), the highest occupied of hole injecting material
Molecular orbital) between the work function of anode material and the HOMO of surrounding organic matter layer.As hole infusion
The concrete example of matter has metalloporphyrin (porphyrin), Oligopoly thiophene, aryl amine system organic matter, six nitriles, six azepine benzophenanthrene system to have
It is organic matter, anthraquinone and polyaniline and polythiophene that machine object, quinacridone (quinacridone), which are organic matter, (perylene),
It is electroconductive polymer etc., but is not limited only to this.
Above-mentioned hole transmission layer is to receive the hole from hole injection layer and by the layer of hole transport to luminescent layer, as
Hole transporting material is the substance that can be received the hole from anode or hole injection layer and transfer them to luminescent layer, right
The big substance of the mobility in hole is suitable.As concrete example, there are aryl amine system organic matter, electroconductive polymer, Yi Jitong
When there are conjugate moieties and the block copolymer of non-conjugated portion etc., but be not limited only to this.
Above-mentioned electronic barrier layer is to prevent the layer mobile to hole transmission layer direction by the superfluous electronics of luminescent layer.Make
For above-mentioned electronic blocking substance, it is however preferred to have LUMO (minimum non-occupied orbital, the Lowest lower than hole transmission layer
Unoccupied Molecular Orbital) energy level substance, it may be considered that the energy level of peripheral layer and select substance appropriate.
In one embodiment, as electronic barrier layer, the organic matter of aryl amine system can be used, but not limited to this.One embodiment party
In formula, above-mentioned electronic barrier layer includes the compound indicated by above-mentioned chemical formula 1.
It is that can receive the sky from hole transmission layer and electron transfer layer respectively as the luminescent substance of above-mentioned luminescent layer
Cave and electronics and make they in conjunction with and issue the substance of the light of visible light region, the preferably quantum efficiency for fluorescence or phosphorescence
High substance.As a specific example, there is 8-hydroxyquinoline aluminum complex (Alq3)；Carbazole based compound；Two is polystyrene-based
(dimerized styryl) compound；BAlq；10- hydroxy benzo quinoline metal compound；BenzoAzoles, benzothiazole and
Benzimidazole based compound；Poly- (to phenylene vinylidene) (PPV) is macromolecule；Loop coil (spiro) compound；Polyfluorene；It is red
Glimmering alkene etc., but it is not limited only to this.
Above-mentioned luminescent layer may include material of main part and dopant material.Material of main part has aromatic fused ring derivative or contains
Heterocyclic compound etc..Specifically, having anthracene derivant, pyrene derivatives, naphthalene derivatives and five as aromatic fused ring derivative
Benzene derivative, phenanthrene compound, fluoranthene compound etc. have carbazole derivates, dibenzofurans derivative as nitrogen-containing heterocgcies
Object, ladder type furan compoundPyrimidine derivatives etc., but not limited to this.
As dopant material, have aromatic amine derivative, styrylamine compounds, boron complexes, fluoranthene compound,
Metal complex etc..Specifically, being the aromatic series with substituted or unsubstituted arylamino as aromatic amine derivative
Fused-ring derivatives, have pyrene with arylamino, anthracene,Two indeno pyrenes (Periflanthene) etc., as styryl amine
Compound is to replace to have the compound of at least one aryl vinyl on substituted or unsubstituted arylamine, by selected from aryl,
Substituent group more than one or two of silicyl, alkyl, naphthenic base and arylamino is substituted or unsubstituted.It is specific and
Speech, has styryl amine, styryl diamines, styryl triamine, styryl tetramine etc., but not limited to this.In addition,
As metal complex, there are complex of iridium, platinum complex etc., but not limited to this.
Above-mentioned electrical adjustment layer be stop hole from luminescent layer flow into cathode and adjust flow into luminescent layer electronics and to member
The layer that the performance of part entirety is adjusted.As electrical adjustment substance, preferably having prevents hole from flowing into cathode simultaneously from luminescent layer
To the compound for the ability that the electronics for being injected into luminescent layer or luminescent material is adjusted.As electrical adjustment substance, Ke Yigen
Substance appropriate is used according to the composition of the organic matter layer used in element.Above-mentioned electrical adjustment layer be located at luminescent layer and cathode it
Between, preferably have in a manner of directly connecting with luminescent layer.
Above-mentioned electron transfer layer is from electron injecting layer reception electronics and by the layer of electron-transport to luminescent layer, as electronics
Transport materials are can to receive well electronics from cathode and transfer them to the substance of luminescent layer, big to the mobility of electronics
Substance be suitable.As concrete example, there is the Al complex of 8-hydroxyquinoline, comprising Alq3Complex, organic free radical
Compound, hydroxyl brass-metal complex etc., but it is not limited only to this.Electron transfer layer can be as used in the prior art
It is used together like that with the cathode substance of any desired.In particular, the example of suitable cathode substance be with low work function and
With aluminium layer or the common substance of silver layer.Specially caesium, barium, calcium, ytterbium and samarium, in every case, with aluminium layer or silver layer.
Above-mentioned electron injecting layer is the layer for the electronics that injection carrys out self-electrode, preferably following compound: has transmission electronics
Ability, there is electron injection effect from cathode, for the excellent electron injection effect of luminescent layer or luminescent material, prevent
Only generated exciton is migrated to hole injection layer in luminescent layer, and film Forming ability is excellent.Specifically, have Fluorenone,
Anthraquinone bismethane (Anthraquinodimethane), diphenoquinone, thiopyrandioxide,Azoles,Diazole, triazole, imidazoles,
Tetrabasic carboxylic acid, fluorenylidene-methane, anthrone etc. and their derivative, metal complex and nitrogenous five-membered ring derivative etc., but
It's not limited to that.
Above-mentioned hole blocking layer is the layer for preventing hole from reaching cathode, usually can use item identical with hole injection layer
Part is formed.Specifically, havingOxadiazole derivative or triazole derivative, phenanthroline derivative, BCP, aluminum complex
(aluminum complex) etc., but not limited to this.
As above-mentioned metal complex, there are 8-hydroxyquinoline lithium, bis- (8-hydroxyquinoline) zinc, bis- (8-hydroxyquinolines)
Copper, bis- (8-hydroxyquinoline) manganese, three (8-hydroxyquinoline) aluminium, three (2- methyl -8-hydroxyquinoline) aluminium, three (8-hydroxyquinolines)
Gallium, bis- (10- hydroxy benzo [h] quinoline) berylliums, bis- (10- hydroxy benzo [h] quinoline) zinc, bis- (2- methyl -8- quinoline) gallium chlorides,
Bis- (2- methyl -8- quinoline) (o-cresol) galliums, bis- (2- methyl -8- quinoline) (1- naphthols) aluminium, bis- (2- methyl -8- quinoline) (2-
Naphthols) gallium etc., but not limited to this.
It can be top emission type, bottom-emission according to the organic illuminating element of this specification according to used material
Type or bidirectional luminescence type.
According to an embodiment of this specification, other than organic illuminating element can also in organic solar batteries or
Contain the compound indicated by above-mentioned chemical formula 1 or chemical formula 3 in organic transistor.
The mode to carry out an invention
In the following, enumerating embodiment in order to illustrate this specification and being described in detail.But according to this specification
Embodiment can be deformed into various other forms, the range that should not be construed as this specification is defined in implementation described below
Example.The embodiment of this specification is provided to more completely illustrate this specification to those skilled in the art.
<synthesis example>
The synthesis of<Production Example 1-1>compound E1
By above compound 4,4,5,5- tetramethyl -2- (spiral shell [fluorenes -9,9'- xanthene] -2'- base) -1,3,2- dioxa boron
Heterocycle pentane (10.0g, 21.8mmol) and 2- ([1,1'- xenyl] -4- base) -4- chloro-6-phenyl -1,3,5- triazine (7.5g,
After 21.8mmol) being dissolved completely in tetrahydrofuran (100ml), by potassium carbonate (9.0g, 65.4mmol) be dissolved in 50ml water and
Addition, after tetrakis triphenylphosphine palladium (756mg, 0.65mmol) is added, heating stirring 8 hours.Room temperature is cooled the temperature to, is terminated anti-
Ying Hou removes solution of potassium carbonate, filters above-mentioned white solid.By the solid tetrahydrofuran and ethyl acetate of the white of filtering
It washs 2 times respectively and has manufactured above compound E1 (12.6g, yield 90%).
MS[M+H]+=640
The synthesis of<Production Example 1-2>compound E2
In Production Example 1-1, above compound 2- is replaced using 2- (3- bromophenyl) -4,6- diphenyl -1,3,5-triazines
([1,1'- xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines, in addition to this, by identical as above-mentioned Production Example 1-1
Method manufactured above compound E2.
MS[M+H]+=640
The synthesis of<Production Example 1-3>compound E3
In Production Example 1-1, above compound 2- is replaced using 4- (6- chloropyridine -3- base) -2,6- diphenylpyrimidin
([1,1'- xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines, in addition to this, by identical as above-mentioned Production Example 1-1
Method manufactured above compound E3.
MS[M+H]+=640
The synthesis of<Production Example 1-4>compound E4
In Production Example 1-1, above compound 2- ([1,1'- connection is replaced using 2- (4- chlorphenyl) -4- phenylquinazoline
Phenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines, in addition to this, pass through method identical with above-mentioned Production Example 1-1 manufacture
Above compound E4.
MS[M+H]+=613
The synthesis of<Production Example 1-5>compound E5
In Production Example 1-1,4,4,5,5- tetramethyl -2- (spiral shell [fluorenes -9,9'- xanthene] -3'- base) -1,3,2- bis- are used
Oxa- boron heterocycle pentane replaces above compound 4,4,5,5- tetramethyl -2- (spiral shell [fluorenes -9,9'- xanthene] -2'- base) -1,3,2-
Dioxaborolan alkane uses the chloro- 4- of 2- (4- (dibenzo [b, d] furans -4- base) phenyl) -6- phenyl -1,3,5-triazines
Instead of above compound 2- ([1,1'- xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines, in addition to this, by with it is upper
It states the identical method of Production Example 1-1 and has manufactured above compound E5.
MS[M+H]+=730
The synthesis of<Production Example 1-6>compound E6
In Production Example 1-5, above compound is replaced using 2- (4- chlorphenyl) -4- phenyl -6- (pyridine -2- base) pyrimidine
The chloro- 4- of 2- (4- (dibenzo [b, d] furans -4- base) phenyl) -6- phenyl -1,3,5-triazines, in addition to this, by with above-mentioned system
It makes the identical method of a 1-5 and has manufactured above compound E6.
MS[M+H]+=640
The synthesis of<Production Example 1-7>compound E7
In Production Example 1-5, above compound 2- is replaced using 2- (4- bromophenyl) -1- phenyl -1H- benzo [d] imidazoles
Chloro- 4- (4- (dibenzo [b, d] furans -4- base) phenyl) -6- phenyl -1,3,5-triazines, in addition to this, by with above-mentioned manufacture
The identical method of example 1-5 has manufactured above compound E7.
MS[M+H]+=601
The synthesis of<Production Example 1-8>compound E8
In Production Example 1-1,4,4,5,5- tetramethyl -2- (spiral shell [fluorenes -9,9'- xanthene] -4'- base) -1,3,2- bis- are used
Oxa- boron heterocycle pentane replaces above compound 4,4,5,5- tetramethyl -2- (spiral shell [fluorenes -9,9'- xanthene] -2'- base) -1,3,2-
Dioxaborolan alkane uses 2- ([1,1'- xenyl] -4- base) -4- (4- chlorphenyl) -6- phenyl -1,3,5-triazines generation
For 2- ([1,1'- xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines, in addition to this, by with above-mentioned Production Example 1-1
Identical method has manufactured above compound E8.
MS[M+H]+=716
The synthesis of<Production Example 1-9>compound E9
In Production Example 1-8, above compound 2- ([1,1'- xenyl] -4- is replaced using bromo- 1, the 10- phenanthroline of 2-
Base) -4- (4- chlorphenyl) -6- phenyl -1,3,5-triazines, in addition to this, pass through method identical with above-mentioned Production Example 1-8 manufacture
Above compound E9.
MS[M+H]+=511
The synthesis of<Production Example 1-10>compound E10
In Production Example 1-1, replaced using 9- (4- (4- chloro-6-phenyl -1,3,5-triazines -2- base) phenyl) -9H- carbazole
Above compound 2- ([1,1'- xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines, in addition to this, by with above-mentioned system
It makes the identical method of a 1-1 and has manufactured above compound E10.
MS[M+H]+=729
The synthesis of<Production Example 1-11>compound E11
In Production Example 1-5, the chloro- 4- phenyl -6- of 2- (3- (triphenylene -2- base) phenyl) -1,3,5-triazines generation is used
For the chloro- 4- of above compound 2- (4- (dibenzo [b, d] furans -4- base) phenyl) -6- phenyl -1,3,5-triazines, in addition to this,
Above compound E11 has been manufactured by method identical with above-mentioned Production Example 1-5.
MS[M+H]+=790
The synthesis of<Production Example 1-12>compound E12
In Production Example 1-8, replaced using the chloro- 4- phenyl -6- of 2- (4- (pyridine -2- base) phenyl) -1,3,5-triazines upper
State compound 2- ([1,1'- xenyl] -4- base) -4- (4- chlorphenyl) -6- phenyl -1,3,5-triazines, in addition to this, by with
The identical method of above-mentioned Production Example 1-8 has manufactured above compound E12.
MS[M+H]+=641
The synthesis of<Production Example 1-13>compound E13
In Production Example 1-8, above-mentionedization is replaced using 9- (4- (the chloro- 2- phenylpyridine -4- base of 6-) phenyl) -9H- carbazole
Close object 2- ([1,1'- xenyl] -4- base) -4- (4- chlorphenyl) -6- phenyl -1,3,5-triazines, in addition to this, by with it is above-mentioned
The identical method of Production Example 1-8 has manufactured above compound E13.
MS[M+H]+=728
The synthesis of<Production Example 1-14>compound E14
In Production Example 1-1, the chloro- 4- of 2- (4- (dibenzo [b, d] thiene-3-yl) phenyl) -6- phenyl -1,3,5- are used
Triazine replaces above compound 2- ([1,1'- xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines to pass through in addition to this
Method identical with above-mentioned Production Example 1-1 has manufactured above compound E14.
MS[M+H]+=746
The synthesis of<Production Example 1-15>compound E15
In Production Example 1-8, replaced using 2- ([1,1'- xenyl] -4- base) -4- chloro-6-phenyl -1,3,5-triazines upper
State compound 2- ([1,1'- xenyl] -4- base) -4- (4- chlorphenyl) -6- phenyl -1,3,5-triazines, in addition to this, by with
The identical method of Production Example 1-8 has manufactured above compound E15.
MS[M+H]+=640
The synthesis of<Production Example 1-16>compound E16
Keep each initial substance identical as above-mentioned reaction equation, in addition to this, is manufactured by method identical with Production Example 1-1
Above compound E16.
MS[M+H]+=536
The synthesis of<Production Example 1-17>compound E17
Keep each initial substance identical as above-mentioned reaction equation, in addition to this, is manufactured by method identical with Production Example 1-1
Above compound E17.
MS[M+H]+=477
The synthesis of<Production Example 1-18>compound E18
Keep each initial substance identical as above-mentioned reaction equation, in addition to this, is manufactured by method identical with Production Example 1-1
Above compound E18.
MS[M+H]+=537
The synthesis of<Production Example 1-19>compound E19
Keep each initial substance identical as above-mentioned reaction equation, in addition to this, is manufactured by method identical with Production Example 1-1
Above compound E19.
MS[M+H]+=487
The synthesis of<Production Example 1-20>compound E20
Keep each initial substance identical as above-mentioned reaction equation, in addition to this, is manufactured by method identical with Production Example 1-1
Above compound E20.
MS[M+H]+=460
The synthesis of<Production Example 1-21>compound E21
Keep each initial substance identical as above-mentioned reaction equation, in addition to this, is manufactured by method identical with Production Example 1-1
Above compound E21.
MS[M+H]+=562
The synthesis of<Production Example 1-22>compound E22
Keep each initial substance identical as above-mentioned reaction equation, in addition to this, is manufactured by method identical with Production Example 1-1
Above compound E22.
MS[M+H]+=716
The synthesis of<Production Example 1-23>compound E23
Keep each initial substance identical as above-mentioned reaction equation, in addition to this, is manufactured by method identical with Production Example 1-1
Above compound E23.
MS[M+H]+=716
The synthesis of<Production Example 2-1>compound F1
Keep each initial substance identical as above-mentioned reaction equation, sodium tert-butoxide (1.4eq) be added to dimethylbenzene (Xylene),
[bis- (tri-tert-butylphosphines)] palladium of 2mmol% is added after heating stirring at 80 DEG C.Room temperature is cooled the temperature to, after reaction was completed, benefit
Compound F1 has been manufactured with chloroform and re-crystallizing in ethyl acetate.
MS[M+H]+=729
The synthesis of<Production Example 2-2>compound F2
Keep each initial substance identical as above-mentioned reaction equation, in addition to this, is manufactured by method identical with Production Example 2-1
Above compound F2.
MS[M+H]+=729
<experimental example 1-1>
It will be withThickness thin film be coated with the glass substrate of ITO (tin indium oxide, indium tin oxide) and put
Enter in the distilled water dissolved with detergent, is washed using ultrasonic wave.At this moment, detergent uses Fei Xier company (Fischer
Co.) product, distilled water is used to be filtered twice using the filter (Filter) of Millipore Corp. (Millipore Co.) manufacture
Distilled water.After ITO is washed 30 minutes, it is repeated twice with distilled water and carries out 10 minutes ultrasonic washings.It is washed in distillation
After washing, after being carried out ultrasonic washing with the solvent of isopropanol, acetone, methanol and dried, it is delivered to plasma washing machine.
In addition, after five minutes by aforesaid substrate cleaning, delivering the substrate to vacuum evaporation plating machine using oxygen plasma.
On the ito transparent electrode prepared in this way withThickness by following compounds [HI-A] carry out thermal vacuum steaming
It plates and forms hole injection layer.The successively vacuum evaporation on above-mentioned hole injection layerFollowing chemical formula six nitriles, six nitrogen
Miscellaneous benzophenanthrene (hexaazatriphenylene；) and following compounds [HT-A] HATAnd form hole transmission layer.
Then, on above-mentioned hole transmission layer vacuum evaporation above-mentioned [compound F1] and withThickness form electricity
Sub- barrier layer.
On above-mentioned electronic barrier layer with the weight ratio of 25:1 by following compounds [BH] and [BD] with film thickness
It carries out vacuum evaporation and forms luminescent layer.
The vacuum evaporation above-mentioned [compound E1] on above-mentioned luminescent layer and withThickness form electrical adjustment layer.
With 1:1 weight ratio by following [compound ET-1-J] and following compounds [LiQ] (8-hydroxyquinoline on above-mentioned electrical adjustment layer
Lithium, Lithiumquinolate) carry out vacuum evaporation and withThickness formed electron transfer layer.In above-mentioned electron-transport
On layer successively by lithium fluoride (LiF) withThickness, by aluminium withThickness is deposited, to form cathode.
In above process, organic matter evaporation rate maintain 0.4 toThe lithium fluoride of cathode maintainsEvaporation rate, aluminium maintainEvaporation rate, vapor deposition when, vacuum degree maintain 1 × 10-7To 5 ×
10-8Support, to make organic illuminating element.
<experimental example 1-2>
In above-mentioned experimental example 1-1, using above compound E2 replace compound E1, in addition to this, by with experimental example 1-1
Identical method has made organic illuminating element.
<experimental example 1-3>
In above-mentioned experimental example 1-1, using above compound E3 replace compound E1, in addition to this, by with experimental example 1-1
Identical method has made organic illuminating element.
<experimental example 1-4>
In above-mentioned experimental example 1-1, using above compound E4 replace compound E1, in addition to this, by with experimental example 1-1
Identical method has made organic illuminating element.
<experimental example 1-5>
In above-mentioned experimental example 1-1, using above compound E5 replace compound E1, in addition to this, by with experimental example 1-1
Identical method has made organic illuminating element.
<experimental example 1-6>
In above-mentioned experimental example 1-1, using above compound E6 replace compound E1, in addition to this, by with experimental example 1-1
Identical method has made organic illuminating element.
<experimental example 1-7>
In above-mentioned experimental example 1-1, using above compound E7 replace compound E1, in addition to this, by with experimental example 1-1
Identical method has made organic illuminating element.
<experimental example 1-8>
In above-mentioned experimental example 1-1, using above compound E8 replace compound E1, in addition to this, by with experimental example 1-1
Identical method has made organic illuminating element.
<experimental example 1-9>
In above-mentioned experimental example 1-1, using above compound E9 replace compound E1, in addition to this, by with experimental example 1-1
Identical method has made organic illuminating element.
<experimental example 1-10>
In above-mentioned experimental example 1-1, using above compound E10 replace compound E1, in addition to this, by with experimental example 1-
1 identical method has made organic illuminating element.
<experimental example 1-11>
In above-mentioned experimental example 1-1, using above compound E11 replace compound E1, in addition to this, by with experimental example 1-
1 identical method has made organic illuminating element.
<experimental example 1-12>
In above-mentioned experimental example 1-1, using above compound E12 replace compound E1, in addition to this, by with experimental example 1-
1 identical method has made organic illuminating element.
<experimental example 1-13>
In above-mentioned experimental example 1-1, using above compound E13 replace compound E1, in addition to this, by with experimental example 1-
1 identical method has made organic illuminating element.
<experimental example 1-14>
In above-mentioned experimental example 1-1, using above compound E14 replace compound E1, in addition to this, by with experimental example 1-
1 identical method has made organic illuminating element.
<experimental example 1-15>
In above-mentioned experimental example 1-1, using above compound E15 replace compound E1, in addition to this, by with experimental example 1-
1 identical method has made organic illuminating element.
<experimental example 1-16>
In above-mentioned experimental example 1-1, using above compound E16 replace compound E1, in addition to this, by with experimental example 1-
1 identical method has made organic illuminating element.
<experimental example 1-17>
In above-mentioned experimental example 1-1, using above compound E17 replace compound E1, in addition to this, by with experimental example 1-
1 identical method has made organic illuminating element.
<experimental example 1-18>
In above-mentioned experimental example 1-1, using above compound E18 replace compound E1, in addition to this, by with experimental example 1-
1 identical method has made organic illuminating element.
<experimental example 1-19>
In above-mentioned experimental example 1-1, using above compound E19 replace compound E1, in addition to this, by with experimental example 1-
1 identical method has made organic illuminating element.
<experimental example 1-20>
In above-mentioned experimental example 1-1, using above compound E20 replace compound E1, in addition to this, by with experimental example 1-
1 identical method has made organic illuminating element.
<experimental example 1-21>
In above-mentioned experimental example 1-1, using above compound E21 replace compound E1, in addition to this, by with experimental example 1-
1 identical method has made organic illuminating element.
<experimental example 1-22>
In above-mentioned experimental example 1-1, using above compound E22 replace compound E1, in addition to this, by with experimental example 1-
1 identical method has made organic illuminating element.
<experimental example 1-23>
In above-mentioned experimental example 1-1, using above compound E23 replace compound E1, in addition to this, by with experimental example 1-
1 identical method has made organic illuminating element.
<experimental example 1-24>
In above-mentioned experimental example 1-1, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-1
Identical method has made organic illuminating element.
<experimental example 1-25>
In above-mentioned experimental example 1-2, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-2
Identical method has made organic illuminating element.
<experimental example 1-26>
In above-mentioned experimental example 1-3, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-3
Identical method has made organic illuminating element.
<experimental example 1-27>
In above-mentioned experimental example 1-4, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-4
Identical method has made organic illuminating element.
<experimental example 1-28>
In above-mentioned experimental example 1-5, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-5
Identical method has made organic illuminating element.
<experimental example 1-29>
In above-mentioned experimental example 1-6, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-6
Identical method has made organic illuminating element.
<experimental example 1-30>
In above-mentioned experimental example 1-7, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-7
Identical method has made organic illuminating element.
<experimental example 1-31>
In above-mentioned experimental example 1-8, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-8
Identical method has made organic illuminating element.
<experimental example 1-32>
In above-mentioned experimental example 1-9, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-9
Identical method has made organic illuminating element.
<experimental example 1-33>
In above-mentioned experimental example 1-10, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-
10 identical methods have made organic illuminating element.
<experimental example 1-34>
In above-mentioned experimental example 1-11, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-
11 identical methods have made organic illuminating element.
<experimental example 1-35>
In above-mentioned experimental example 1-12, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-
12 identical methods have made organic illuminating element.
<experimental example 1-36>
In above-mentioned experimental example 1-13, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-
13 identical methods have made organic illuminating element.
<experimental example 1-37>
In above-mentioned experimental example 1-14, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-
14 identical methods have made organic illuminating element.
<experimental example 1-38>
In above-mentioned experimental example 1-15, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-
15 identical methods have made organic illuminating element.
<experimental example 1-39>
In above-mentioned experimental example 1-16, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-
16 identical methods have made organic illuminating element.
<experimental example 1-40>
In above-mentioned experimental example 1-17, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-
17 identical methods have made organic illuminating element.
<experimental example 1-41>
In above-mentioned experimental example 1-18, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-
18 identical methods have made organic illuminating element.
<experimental example 1-42>
In above-mentioned experimental example 1-19, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-
19 identical methods have made organic illuminating element.
<experimental example 1-43>
In above-mentioned experimental example 1-20, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-
20 identical methods have made organic illuminating element.
<experimental example 1-44>
In above-mentioned experimental example 1-21, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-
21 identical methods have made organic illuminating element.
<experimental example 1-45>
In above-mentioned experimental example 1-22, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-
22 identical methods have made organic illuminating element.
<experimental example 1-46>
In above-mentioned experimental example 1-23, using above compound F2 replace compound F1, in addition to this, by with experimental example 1-
23 identical methods have made organic illuminating element.
<comparative example 1-1>
In above-mentioned experimental example 1-1, using above compound ET-1-A replace compound E1, in addition to this, by with experiment
The identical method of example 1-1 has made organic illuminating element.
<comparative example 1-2>
In above-mentioned experimental example 1-1, using above compound ET-1-B replace compound E1, in addition to this, by with experiment
The identical method of example 1-1 has made organic illuminating element.
<comparative example 1-3>
In above-mentioned experimental example 1-1, using above compound ET-1-C replace compound E1, in addition to this, by with experiment
The identical method of example 1-1 has made organic illuminating element.
<comparative example 1-4>
In above-mentioned experimental example 1-1, using above compound ET-1-D replace compound E1, in addition to this, by with experiment
The identical method of example 1-1 has made organic illuminating element.
<comparative example 1-5>
In above-mentioned experimental example 1-1, using above compound ET-1-E replace compound E1, in addition to this, by with experiment
The identical method of example 1-1 has made organic illuminating element.
<comparative example 1-6>
In above-mentioned experimental example 1-1, using above compound ET-1-F replace compound E1, in addition to this, by with experiment
The identical method of example 1-1 has made organic illuminating element.
<comparative example 1-7>
In above-mentioned experimental example 1-1, using above compound ET-1-G replace compound E1, in addition to this, by with experiment
The identical method of example 1-1 has made organic illuminating element.
<comparative example 1-8>
In above-mentioned experimental example 1-1, using above compound ET-1-H replace compound E1, in addition to this, by with experiment
The identical method of example 1-1 has made organic illuminating element.
<comparative example 1-9>
In above-mentioned experimental example 1-1, using above compound ET-1-I replace compound E1, in addition to this, by with experiment
The identical method of example 1-1 has made organic illuminating element.
<comparative example 1-10>
In above-mentioned experimental example 1-1, using above compound ET-1-J replace compound E1, in addition to this, by with experiment
The identical method of example 1-1 has made organic illuminating element.
<comparative example 1-11>
In above-mentioned experimental example 1-1, using above compound ET-1-K replace compound E1, in addition to this, by with experiment
The identical method of example 1-1 has made organic illuminating element.
<comparative example 1-12>
In above-mentioned experimental example 1-2, using above compound HT-1-A replace compound F1, in addition to this, by with experiment
The identical method of example 1-2 has made organic illuminating element.
<comparative example 1-13>
In above-mentioned experimental example 1-2, using above compound HT-1-B replace compound F1, in addition to this, by with experiment
The identical method of example 1-2 has made organic illuminating element.
<comparative example 1-14>
In above-mentioned experimental example 1-2, using above compound HT-1-C replace compound F1, in addition to this, by with experiment
The identical method of example 1-2 has made organic illuminating element.
<comparative example 1-15>
In above-mentioned experimental example 1-2, using above compound HT-1-D replace compound F1, in addition to this, by with experiment
The identical method of example 1-2 has made organic illuminating element.
<comparative example 1-16>
In above-mentioned experimental example 1-1, under conditions of no electrical adjustment layer, with 1:1 weight ratio by above compound ET-1-
J and LiQ carry out vacuum evaporation and withThickness formed electron transfer layer, in addition to this, by identical as experimental example 1-1
Method made organic illuminating element.
<comparative example 1-17>
In above-mentioned experimental example 1-2, under conditions of no electronic barrier layer, successively will on hole injection layerIt is upper
State six nitriles, the six azepine benzophenanthrene (hexaazatriphenylene of chemical formula；) and above compound [HT-A] HAT
It carries out vacuum evaporation and forms hole transmission layer, in addition to this, organic light emission has been made by method identical with experimental example 1-1
Element.
<comparative example 1-18>
In above-mentioned experimental example 1-1, under conditions of no electronic barrier layer, successively will on hole injection layerIt is upper
State six nitriles, the six azepine benzophenanthrene (hexaazatriphenylene of chemical formula；) and above compound [HT-A] HAT
It carries out vacuum evaporation and forms hole transmission layer, under conditions of no electrical adjustment layer, with 1:1 weight ratio by above compound
ET-1-J and LiQ carry out vacuum evaporation and withThickness formed electron transfer layer, in addition to this, by with experimental example 1-
1 identical method has made organic illuminating element.
The organic illuminating element that will be manufactured by the method for above-mentioned experimental example 1-1 to 1-46 and comparative example 1-1 to 1-18
In 10mA/cm2Current density under measure driving voltage and luminous efficiency, in 20mA/cm2Current density under determine it is opposite
Become 90% time (T in original intensity90).It the results are shown in following table 1.
[table 1]
From the result of above-mentioned table 1 it has been confirmed that if to experimental example 1-1 to 1-46 and comparative example 1-1,1-2,1-3,1-5,1-
7,1-8,1-9 are compared, and only replace the compound for having a heteroaryl on spiro fluorene xanthene skeleton as above-mentioned chemical formula 1
Compared with the compound on spiro fluorene xanthene skeleton with more than two substituent groups, in organic illuminating element, in driving electricity
Excellent characteristic is shown in terms of pressure, efficiency and service life.
It, can be with according to Figure 10 and Figure 11 of the 3D structure of the compound E9 and E18 of the embodiment for showing this specification
Confirm that the molecule of above compound has horizontal structure, according to the Figure 12 for the 3D structure for showing compound ET-1-E and ET-1-I and
A axis and B axle can be confirmed almost at vertical in Figure 13 respectively, and molecule substantially deviates from horizontal structure.
As a result it is found that if Figure 10 to the 3D structure of the compound E9 and E18 of the embodiment for showing this specification and
Figure 11 is compared with Figure 12 and Figure 13 of the 3D structure for showing compound ET-1-E and ET-1-I, according in the 3D structure of molecule
Orientation (orientation) difference, according to the heterocyclic compound of an embodiment of this specification indicated by chemical formula 1
With more horizontal structure.Therefore, experimental example 1-1 to 1-46 only takes on spiro fluorene xanthene skeleton as above-mentioned chemical formula 1
The compound of Dai Youyi heteroaryl is compared with the compound on spiro fluorene xanthene skeleton with more than two substituent groups, molecule
Horizontal structure tendency it is stronger, electron mobility is got higher, thus have in organic illuminating element driving voltage is low, high efficiency and
The effect of long-life.
In addition, if being compared to experimental example 1-1 to 1-46 and comparative example 1-4 and 1-6, it has been confirmed that including spiro fluorene Xanthones
The structure of the above-mentioned chemical formula 1 of ton shows excellent characteristic compared with comprising Spirofluorene-based structure in organic illuminating element.
In addition, if being compared to experimental example 1-16,1-39 and comparative example 1-11, it has been confirmed that including spiro fluorene xanthene
The structure of above-mentioned chemical formula 1 is according to the binding site of the quinoline on spiro fluorene xanthene, and the phenyl ring comprising N is not incorporated on spiro fluorene xanthene
Above-mentioned chemical formula 1 structure compared with the compound that the phenyl ring comprising N is incorporated on spiro fluorene xanthene, in organic illuminating element
Show excellent characteristic.
If being compared to experimental example 1-1 to 1-46 and comparative example 1-12,1-13, it has been confirmed that with as electronic blocking
The compound without carbazole substituent group that layer uses is compared, and is made using the compound of the chemical formula 3 with carbazole substituent group
In the case where for electronic barrier layer, excellent efficiency and life characteristic are shown in organic illuminating element.
If being compared to experimental example 1-1 to 1-46 and comparative example 1-12,1-14, it has been confirmed that with as electronic blocking
What layer used compares without the compound that is replaced with dibenzofuran group, using replacing the chemical formula 3 for having dibenzofuran group
Compound as electronic barrier layer in the case where, excellent efficiency and life characteristic are shown in organic illuminating element.
Furthermore it is possible to confirm, with use the carbazole of comparative example 1-14,1-15 to align substituted compound as electronics
The case where barrier layer, is compared, and the case where carbazole is using the compound of the substituted chemical formula 3 of meta position as electronic barrier layer is being used
Under, excellent efficiency and life characteristic are shown in organic illuminating element.
In addition, if being compared to experimental example 1-1 to 1-46 and comparative example 1-16 to 1-18, it has been confirmed that with organic hair
The structure that at least one of electronic barrier layer in optical element and electrical adjustment layer do not form a film is compared, comprising containing chemical formula
It is shown in the organic illuminating element of the electronic barrier layer of the electrical adjustment layer and compound containing chemical formula 3 of 1 compound
Excellent efficiency, life characteristic.
According to the excellent heat stability for the heterocyclic compound of an embodiment of this specification indicated by chemical formula 1, tool
There is deep HOMO energy level, high triplet energy (ET) and the hole stability of 6.0eV or more and can show that excellent spy
Property.
In particular, in experimental example, in the case that Ar1 is triazine radical or pyrimidine radicals in above-mentioned chemical formula 1, HOMO energy
It is deep to 6.1eV or more, especially successfully plays the effect as electrical adjustment layer (hole blocking layer), electron mobility is high, In
When for organic illuminating element, in driving voltage, efficiency and excellent characteristic can be shown in terms of the service life.Specifically, In
Experimental example 1-1 is to 1-3,1-5,1-6,1-8,1-10 to 1-15,1-22 to 1-26,1-28,1-29,1-31,1-33 to 1-38,1-
45, in 1-46, with Ar1 be pyridyl group (1 N) experimental example 1-21,1-44 the case where compared with, driving voltage, efficiency and/or
Excellent characteristic can be shown in terms of service life.
In addition, in the case where constituting electronic barrier layer by chemical formula 3, HOMO energy is formed as 5.5eV or more, to make
It is smooth to the injection of the hole of luminescent layer.(referring to following experimental examples 2)
As a result, according to the heterocyclic compound of an embodiment of this specification indicated by chemical formula 1 and/or chemical formula 3
With low driving voltage and high efficiency, the stability of element can be improved by the hole stability of compound.
<experimental example 2>
It will be according to the following compound E1 for being equivalent to the compound indicated by chemical formula 1 of an embodiment of this specification
With compound E2, the following compound F1 for being equivalent to the compound indicated by chemical formula 3, comparative example compound ET-1-J and HT-
The HOMO energy and LUMO energy value of 1-B is shown in following table 2.
In the embodiment of this specification, above-mentioned HOMO energy level utilizes photoelectron spectroscopy device (RIKEN KEIKI under atmosphere
Co., Ltd. is manufactured: AC3) being measured.
In the embodiment of this specification, in terms of above-mentioned lumo energy is carried out by the wavelength value measured by luminescence generated by light (PL)
It calculates.
[table 2]
| Compound | HOMO(eV) | LUMO(eV) |
| E1 | 6.20 | 2.70 |
| E2 | 6.16 | 2.92 |
| ET-1-J | 5.70 | 2.87 |
| F1 | 5.62 | 2.57 |
| HT-1-B | 5.43 | 2.30 |
The HOMO energy level of above compound E1 and E2 are deep to 6.0eV or more, specifically, being deep to 6.1eV or more.It can be true
The band gap for recognizing above compound E1 and E2 is also 3.0eV or more.Thus, it can be known that the compound indicated by chemical formula 1 is used for electricity
In the case where sub- regulating course (hole blocking layer), electron mobility is high, when being used for organic illuminating element, in driving voltage, effect
Excellent characteristic can be shown in terms of rate and service life.
In addition, compound F1 is formed in such a way that HOMO energy is 5.5eV or more, the case where being configured to electronic barrier layer
Under, it can make to inject to the hole of luminescent layer smooth.
Although by the above content, preferred embodiment of the present invention will be described, the present invention is not limited to this, In
Various forms implementation can be deformed into the range of the scope of protection of present invention and detailed description of the invention, this also belongs to hair
Bright scope.
Symbol description
10,11,12: organic illuminating element
20: substrate
30: anode
40: luminescent layer
50: cathode
60: hole injection layer
70: hole transmission layer
80: electron transfer layer
90: electron injecting layer
100: electrical adjustment layer
101: electronic barrier layer.
Claims (14)
1. a kind of organic illuminating element, includes:
Anode；
Cathode；And
Luminescent layer between the anode and the cathode is provided,
The organic illuminating element also includes:
Electrical adjustment layer is provided between the luminescent layer and the cathode and containing the chemical combination indicated by following chemical formula 1
Object, and
Electronic barrier layer is provided between the luminescent layer and the anode and containing the chemical combination indicated by following chemical formula 3
Object,
Chemical formula 1
In the chemical formula 1,
R1 be hydrogen, deuterium, itrile group, nitro, hydroxyl ,-C (=O) NC (=O) R ,-C (=O) R ,-C (=O) NRR' ,-C (=O) OR,
Substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted alkoxy, substituted or unsubstituted virtue
Oxygroup, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted artyl sulfo, substituted or unsubstituted alkyl sulphonyl,
Substituted or unsubstituted aryl sulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silicyl, substitution do not take
The boryl in generation, substituted or unsubstituted aryl phosphino-, substituted or unsubstituted oxidation phosphino-, takes substituted or unsubstituted amido
Generation or unsubstituted aryl or substituted or unsubstituted heteroaryl, R and R' are same or different to each other, and are each independently alkane
Base, naphthenic base or aryl,
L1 be Direct Bonding, substituted or unsubstituted arlydene or substituted or unsubstituted inferior heteroaryl,
Ar1 be hydrogen, deuterium, itrile group, nitro, hydroxyl ,-C (=O) NC (=O) R ,-C (=O) R ,-C (=O) NRR' ,-C (=O) OR,
Substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted alkoxy, substituted or unsubstituted virtue
Oxygroup, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted artyl sulfo, substituted or unsubstituted alkyl sulphonyl,
Substituted or unsubstituted aryl sulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silicyl, substitution do not take
The boryl in generation, substituted or unsubstituted aryl phosphino-, substituted or unsubstituted oxidation phosphino-, takes substituted or unsubstituted amido
Generation or unsubstituted aryl, heterocycle more than substituted or unsubstituted tricyclic, take the heterocycle of substituted or unsubstituted monocycle
Generation or it is unsubstituted include the bicyclic heterocycle of 2 or more N, substituted or unsubstituted isoquinolyl or by following chemistry
The structure that formula 2 indicates, R and R' are same or different to each other, and are each independently alkyl, naphthenic base or aryl,
The integer that m is 1 to 4, the integer that n is 0 to 3,1≤n+m≤4,
When m and n is respectively 2 or more integer, the structure in 2 or more brackets is same or different to each other,
Chemical formula 2
In the chemical formula 2,
G1 be hydrogen, deuterium, itrile group, nitro, hydroxyl ,-C (=O) NC (=O) R ,-C (=O) R ,-C (=O) NRR' ,-C (=O) OR,
Substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted alkoxy, substituted or unsubstituted virtue
Oxygroup, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted artyl sulfo, substituted or unsubstituted alkyl sulphonyl,
Substituted or unsubstituted aryl sulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silicyl, substitution do not take
The boryl in generation, substituted or unsubstituted aryl phosphino-, substituted or unsubstituted oxidation phosphino-, takes substituted or unsubstituted amido
Generation or unsubstituted aryl or substituted or unsubstituted heteroaryl, R and R' are same or different to each other, and are each independently alkane
Base, naphthenic base or aryl,
The integer that g1 is 1 to 6, when g1 is 2 or more, the G1 is same or different to each other,
It * is the position in conjunction with the L1 of the chemical formula 1,
Chemical formula 3
In the chemical formula 3,
L'1 to L'3 is same or different to each other, and is each independently Direct Bonding, substituted or unsubstituted arlydene or substitution
Or unsubstituted inferior heteroaryl,
N'1 to n'3 is respectively 1 to 4 integer, and when n'1 to n'3 is respectively 2 or more integer, the structure in bracket is mutually the same
Or it is different,
Ar'1 to Ar'3 is same or different to each other, and is each independently hydrogen, substituted or unsubstituted aryl or substitution or does not take
The heteroaryl in generation, or indicated by following chemical formula 4 or 5,
Ar'1 into Ar'3 at least one indicated by following chemical formula 4,
Chemical formula 4
Chemical formula 5
In the chemical formula 4 and 5,
Any of R'1 to R'8 and R'9 is the position of a combination with the L'1 of the chemical formula 3 into L'3,
Rest part in addition to the part of the L'1 of the chemical formula 3 one into L'3 combination other than of the R'1 into R'9 with
And R'10 to R'21 is same or different to each other, be each independently hydrogen, deuterium, itrile group, nitro, hydroxyl ,-C (=O) NC (=O) R ,-
C (=O) R ,-C (=O) NRR' ,-C (=O) OR, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substitution or
Unsubstituted alkoxy, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkyl sulfenyl, substituted or unsubstituted aryl
Sulfenyl, substituted or unsubstituted aryl sulfonyl, substituted or unsubstituted alkenyl, takes substituted or unsubstituted alkyl sulphonyl
Generation or unsubstituted silicyl, substituted or unsubstituted boryl, substituted or unsubstituted amido, substituted or unsubstituted aryl
Phosphino-, substituted or unsubstituted oxidation phosphino-, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, R and R'
It is same or different to each other, is each independently alkyl, naphthenic base or aryl.
2. organic illuminating element according to claim 1, wherein the L1 is Direct Bonding, substituted or unsubstituted Asia
Phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted sub- terphenyl, replaces substituted or unsubstituted biphenylene
Or it is unsubstituted sub- tetrad phenyl, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted
Sub- triphenylene, substituted or unsubstituted sub- pyrenyl, substituted or unsubstituted fluorenylidene, substituted or unsubstituted spiro cyclopentane are sub-
Fluorenyl, substituted or unsubstituted sub- dibenzofuran group, the dibenzothiophene of substituted or unsubstituted divalent, substitution do not take
Sub- carbazyl, substituted or unsubstituted sub-pyridyl group, the furyl of substituted or unsubstituted divalent or the substitution in generation do not take
The thienyl of the divalent in generation.
3. organic illuminating element according to claim 1, wherein the Ar1 is itrile group, substituted or unsubstituted alcoxyl
Base, substituted or unsubstituted oxidation phosphino-, substituted or unsubstituted silicyl, substituted or unsubstituted aryl, substitution or not
More than the heterocycle of substituted monocycle, substituted or unsubstituted tricyclic heterocycle, it is substituted or unsubstituted include 2 or more N
Bicyclic heterocycle, substituted or unsubstituted isoquinolyl or the structure indicated by the chemical formula 2.
4. organic illuminating element according to claim 1, wherein the Ar1 is by being selected from the chemical formula 2 and following chemistry
Any of formula 6 to 15 indicates:
Chemical formula 6
Chemical formula 7
Chemical formula 8
Chemical formula 9
Chemical formula 10
Chemical formula 11
Chemical formula 12
Chemical formula 13
Chemical formula 14
Chemical formula 15
In the chemical formula 6 to 15,
X1 is N or CR11, and X2 is N or CR12, and X3 is N or CR13,
X4 is N or CR14, and X5 is N or CR15, and X6 is N or CR16,
X7 is N or CR17, and X8 is N or CR18, and X9 is N or CR19,
X10 is N or CR20,
X1 into X3 at least two be N, at least one N of X4 into X7,
Y1 be O, S, NQ1 or CQ2Q3, Y2 O, S, NQ4 or CQ5Q6,
Y3 be O, S or NQ7,
Any of G2 to G4 and R11 to R13, G5 are to any of any of G8, G9 to G15, G16 into G21
Either one or two of, any of any of G22 to G27, G28 to G33 and R14 to R17, any of G34 to G42,
Any of any of G43 to G47, G48, G49, R18 and R19 and any of G50 to G61 are and describedization
The position that the L1 of formula 1 is combined, G2 to G61 and R11 into R19 other than the position in conjunction with the L1 of the chemical formula 1
Remaining position, R20 and Q1 be same or different to each other to Q7, be each independently hydrogen, deuterium, itrile group, nitro, hydroxyl ,-C (=
O) NC (=O) R ,-C (=O) R ,-C (=O) NRR' ,-C (=O) OR, substituted or unsubstituted alkyl, substituted or unsubstituted ring
Alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkyl sulfenyl, replace or
Unsubstituted artyl sulfo, substituted or unsubstituted alkyl sulphonyl, substituted or unsubstituted aryl sulfonyl, substitution do not take
The alkenyl in generation, substituted or unsubstituted silicyl, substituted or unsubstituted boryl, substituted or unsubstituted amido, substitution or
Unsubstituted aryl phosphino-, substituted or unsubstituted oxidation phosphino-, substituted or unsubstituted aryl or substituted or unsubstituted
Heteroaryl, R and R' are same or different to each other, and are each independently alkyl, naphthenic base or aryl.
5. organic illuminating element according to claim 1, wherein the chemical formula 1 is by being selected from following chemical formula 1-1 to 1-
Any of 4 indicate:
Chemical formula 1-1
Chemical formula 1-2
Chemical formula 1-3
Chemical formula 1-4
The chemical formula 1-1 into 1-4,
The definition of L1, Ar1, R1 and n are identical as the chemical formula 1.
6. organic illuminating element according to claim 1, wherein at least one of described Ar'1 to Ar'3 is by describedization
Formula 4 indicates that at least one of described Ar'1 to Ar'3 is indicated by the chemical formula 5, remaining is substituted or unsubstituted virtue
Base.
7. organic illuminating element according to claim 1, wherein the L'1 to L'3 is same or different to each other, respectively solely
It is on the spot Direct Bonding, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted sub- three
Xenyl, substituted or unsubstituted naphthalene or substituted or unsubstituted fluorenylidene.
8. organic illuminating element according to claim 1, wherein the R'1 into R'9 in addition to the chemical formula 3
One into L'3 combination of L'1 part other than rest part and R'10 to R'21 be each independently hydrogen.
9. organic illuminating element according to claim 1, wherein the chemical formula 1 is appointing in following compounds
One:
10. organic illuminating element according to claim 1, wherein the chemical formula 3 is appointing in following compounds
One:
11. organic illuminating element according to claim 1, wherein by the HOMO energy for the compound that the chemical formula 1 indicates
Grade is 6.0eV or more, and the HOMO energy level of the compound indicated by the chemical formula 3 is 5.5eV or more.
12. organic illuminating element according to claim 1, wherein by the triplet for the compound that the chemical formula 1 indicates
Energy level is 2.5eV or more.
13. organic illuminating element according to claim 1, wherein the band gap of the compound indicated by the chemical formula 1 is
3.0eV or more, the band gap of the compound indicated by the chemical formula 3 are 3.0eV or more.
14. organic illuminating element according to claim 1, wherein also comprising selected from hole injection layer, hole transmission layer,
The organic matter layer of one or more of electronic barrier layer, hole blocking layer, electron transfer layer and electron injecting layer.
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| PCT/KR2018/006459 WO2018226036A1 (en) | 2017-06-08 | 2018-06-07 | Organic light emitting element |
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| CN113563253A (en) * | 2020-04-28 | 2021-10-29 | 江苏三月科技股份有限公司 | Organic compound with triarylamine as core and application thereof |
| CN113906580A (en) * | 2019-11-29 | 2022-01-07 | 株式会社Lg化学 | Organic light emitting element |
| CN113950754A (en) * | 2020-01-20 | 2022-01-18 | 株式会社Lg化学 | Organic light emitting device |
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| US11479544B2 (en) * | 2017-03-08 | 2022-10-25 | Idemitsu Kosan Co., Ltd. | Compound, material for organic electroluminescence element, organic electroluminescence element, and electronic device |
| WO2020197170A1 (en) * | 2019-03-28 | 2020-10-01 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
| KR20200115159A (en) * | 2019-03-28 | 2020-10-07 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
| KR20210020830A (en) * | 2019-08-14 | 2021-02-24 | 주식회사 엘지화학 | Organic light emitting device |
| KR20210020829A (en) * | 2019-08-14 | 2021-02-24 | 주식회사 엘지화학 | Organic light emitting device |
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| KR20180134160A (en) | 2018-12-18 |
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