CN118056818A - Compound for organic electronic element, organic electronic element using the same, and electronic device using the same - Google Patents
Compound for organic electronic element, organic electronic element using the same, and electronic device using the same Download PDFInfo
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- CN118056818A CN118056818A CN202311542387.9A CN202311542387A CN118056818A CN 118056818 A CN118056818 A CN 118056818A CN 202311542387 A CN202311542387 A CN 202311542387A CN 118056818 A CN118056818 A CN 118056818A
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- aryl
- organic
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 102
- 125000003118 aryl group Chemical group 0.000 claims description 49
- 239000011368 organic material Substances 0.000 claims description 43
- 125000000623 heterocyclic group Chemical group 0.000 claims description 31
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 18
- 229910052805 deuterium Inorganic materials 0.000 claims description 18
- 230000005525 hole transport Effects 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 229910052698 phosphorus Inorganic materials 0.000 claims description 15
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 14
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000000732 arylene group Chemical group 0.000 claims description 10
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 9
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 230000002708 enhancing effect Effects 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000006761 (C6-C60) arylene group Chemical group 0.000 claims description 6
- 125000005567 fluorenylene group Chemical group 0.000 claims description 6
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 5
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 claims description 2
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 claims description 2
- 125000006744 (C2-C60) alkenyl group Chemical group 0.000 claims description 2
- 125000006745 (C2-C60) alkynyl group Chemical group 0.000 claims description 2
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 2
- -1 fused ring group Chemical group 0.000 claims description 2
- 238000005286 illumination Methods 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 156
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- 238000006243 chemical reaction Methods 0.000 description 57
- 230000015572 biosynthetic process Effects 0.000 description 56
- 238000003786 synthesis reaction Methods 0.000 description 56
- 239000000463 material Substances 0.000 description 45
- 239000000047 product Substances 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 238000002347 injection Methods 0.000 description 24
- 239000007924 injection Substances 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 22
- 229910002027 silica gel Inorganic materials 0.000 description 22
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 17
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 16
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 16
- 238000002955 isolation Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 13
- 239000007810 chemical reaction solvent Substances 0.000 description 12
- NCWDBNBNYVVARF-UHFFFAOYSA-N 1,3,2-dioxaborolane Chemical compound B1OCCO1 NCWDBNBNYVVARF-UHFFFAOYSA-N 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- 239000002019 doping agent Substances 0.000 description 10
- 230000007935 neutral effect Effects 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 235000010290 biphenyl Nutrition 0.000 description 9
- 238000000434 field desorption mass spectrometry Methods 0.000 description 9
- 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 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 8
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 7
- 238000000151 deposition Methods 0.000 description 6
- 239000000872 buffer Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000005381 potential energy Methods 0.000 description 5
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- 239000013598 vector Substances 0.000 description 5
- 125000006757 (C2-C30) heterocyclic group Chemical group 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- ZUMHPFURPMPMSM-UHFFFAOYSA-N 1-phenyl-10h-phenothiazine Chemical compound C=12NC3=CC=CC=C3SC2=CC=CC=1C1=CC=CC=C1 ZUMHPFURPMPMSM-UHFFFAOYSA-N 0.000 description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 4
- DKVDSNMJXDQNCD-UHFFFAOYSA-N 1h-pyrrolo[2,3-f]quinazoline Chemical compound N1=CN=CC2=C(NC=C3)C3=CC=C21 DKVDSNMJXDQNCD-UHFFFAOYSA-N 0.000 description 4
- YQJBZDLEEYCHGU-UHFFFAOYSA-N 5-phenylpyrimido[5,4-b]indole Chemical compound C1(=CC=CC=C1)N1C2=C(C=3C=CC=CC1=3)N=CN=C2 YQJBZDLEEYCHGU-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- ITOKSWHFPQBNSE-UHFFFAOYSA-N [1]benzofuro[3,2-d]pyrimidine Chemical compound N1=CN=C2C3=CC=CC=C3OC2=C1 ITOKSWHFPQBNSE-UHFFFAOYSA-N 0.000 description 4
- OICJTSLHQGDCTQ-UHFFFAOYSA-N [1]benzothiolo[3,2-d]pyrimidine Chemical compound N1=CN=C2C3=CC=CC=C3SC2=C1 OICJTSLHQGDCTQ-UHFFFAOYSA-N 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- PQIUGRLKNKSKTC-UHFFFAOYSA-N benzo[h]quinazoline Chemical compound N1=CN=C2C3=CC=CC=C3C=CC2=C1 PQIUGRLKNKSKTC-UHFFFAOYSA-N 0.000 description 4
- 238000004364 calculation method Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- MCBJUXFCNBVPNF-UHFFFAOYSA-N phenanthro[9,10-d]pyrimidine Chemical compound C1=NC=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 MCBJUXFCNBVPNF-UHFFFAOYSA-N 0.000 description 4
- 229950000688 phenothiazine Drugs 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000005182 potential energy surface Methods 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- 239000004936 P-84 Substances 0.000 description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 150000003413 spiro compounds Chemical class 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 description 1
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 1
- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
- KDOQMLIRFUVJNT-UHFFFAOYSA-N 4-n-naphthalen-2-yl-1-n,1-n-bis[4-(n-naphthalen-2-ylanilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 KDOQMLIRFUVJNT-UHFFFAOYSA-N 0.000 description 1
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 1
- 238000003775 Density Functional Theory Methods 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- 241000282372 Panthera onca Species 0.000 description 1
- 208000006930 Pseudomyxoma Peritonei Diseases 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000005018 aryl alkenyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- JAUCCASEHMVMPM-UHFFFAOYSA-N naphtho[2,1-e][1,3]benzoxazole Chemical group C1=CC2=CC=CC=C2C2=C1C(N=CO1)=C1C=C2 JAUCCASEHMVMPM-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 101150075118 sub1 gene Proteins 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
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- Spectroscopy & Molecular Physics (AREA)
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Abstract
The present invention provides novel compounds capable of improving luminous efficiency, stability and lifetime of a device, organic electronic elements using the same, and electronic devices thereof.
Description
Technical Field
The present invention relates to a compound for an organic electronic element, an organic electronic element using the compound, and an electronic device thereof.
Background
In general, an organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic material. An organic electronic element using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer interposed therebetween. Here, in order to increase efficiency and stability of the organic electronic element, the organic material layer is generally composed of a multi-layer structure composed of different materials, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
Materials used as the organic material layer in the organic electronic element may be classified into a light emitting material and a charge transporting material, such as a hole injecting material, a hole transporting material, an electron injecting material, and the like, according to their functions. Also, the light emitting material may be classified into a high molecular weight type and a low molecular weight type according to molecular weight, and it may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Further, the light emitting material may be classified into a blue light emitting material, a green light emitting material, and a red light emitting material according to the emission color, and a yellow light emitting material and an orange light emitting material necessary for realizing more natural colors.
However, when only one material is used as a light emitting material, the maximum emission wavelength is shifted to a longer wavelength due to intermolecular interaction, and there is a problem in that color purity is lowered or device efficiency is lowered due to an emission attenuation effect, so in order to increase color purity and increase light emitting efficiency by energy transfer, a host/dopant system may be used as a light emitting material. The principle is as follows: when a small amount of dopant having a smaller energy band gap than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transferred to the dopant to efficiently emit light. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, light having a desired wavelength can be obtained according to the type of the dopant used.
Currently, the portable display market is a large display, and its size is increasing, and thus, larger power consumption than that required for the existing portable display is required. Therefore, for portable displays with a limited power supply such as a battery, power consumption becomes a very important factor, and also problems of efficiency and lifetime have to be solved.
The efficiency, the service life, and the driving voltage are related to each other, and as the efficiency increases, the driving voltage relatively decreases, and as the driving voltage decreases, crystallization of the organic material due to joule heat generated during driving decreases, and thus the service life tends to increase. However, efficiency cannot be maximized simply by improving the organic material layer. This is because a long service life and high efficiency can be achieved at the same time when the energy level and T1 value between the organic material layers and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined.
Therefore, although permeation and diffusion of a metal oxide from an anode electrode (ITO) into an organic layer, which is one of the reasons for shortening the service life of an organic electronic element, should have stable characteristics against joule heat generated during device driving, and an OLED device is mainly formed by a deposition method, and it is necessary to develop a material that can withstand long-time deposition, i.e., a material having strong heat resistance.
In other words, in order to fully exhibit excellent characteristics of the organic electronic element, materials such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, and the like, which are superior to materials constituting the organic material layer in the device, should be considered to be superior to materials that are stable and effective. But the development of stable and effective organic material layer materials for organic electronic devices has not been fully achieved. Therefore, development of new materials is continuously required, and development of host materials for light emitting layers is particularly urgently required.
Disclosure of Invention
In order to solve the above-described problems of the background art, the present invention has disclosed a compound having a novel structure, and when the compound is applied to an organic electronic element, it has been found that the luminous efficiency, stability and lifetime of the device can be significantly improved.
It is therefore an object of the present invention to provide novel compounds, organic electronic elements using the same, and electronic devices thereof.
Technical scheme
The present invention provides a compound represented by formula (1).
(1)
In another aspect, the present invention provides an organic electronic element including the compound represented by formula (1) and an electronic device thereof.
[ Effect of the invention ]
By using the compound according to the present invention, high luminous efficiency, low driving voltage and high heat resistance of the device can be achieved, and color purity and service life of the device can be greatly improved.
Drawings
Fig. 1 to 3 are exemplary views of an organic electroluminescent device according to the present invention. In the drawings:
100. 200, 300: organic electronic element 110: first electrode
120: Hole injection layer 130: hole transport layer
140: Light emitting layer 150: electron transport layer
160: Electron injection layer 170: second electrode
180: Light efficiency enhancement layer 210: buffer layer
220: Light emission auxiliary layer 320: first hole injection layer
330: First hole transport layer 340: a first light-emitting layer
350: First electron transport layer 360: a first charge generation layer
361: The second charge generation layer 420: a second hole injection layer
430: Second hole transport layer 440: a second light-emitting layer
450: Second electron transport layer CGL: charge generation layer
ST1: first stacked body ST2: a second stack
Detailed Description
Hereinafter, some embodiments of the present invention will be described in detail. Furthermore, in the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.
Furthermore, when describing the components of the present invention, terms such as first, second, A, B, (a), (b), and the like may be used herein. Each of these terms is not intended to limit the substance, order, or sequence of corresponding components, but is merely intended to distinguish the corresponding components from other components. It should be noted that if a component is described as being "connected," "coupled," or "connected" to another component, the component may be directly connected or connected to the other component, but another component may be "connected," "coupled," or "connected" between the components.
As used in the specification and the appended claims, the following are the meanings of the following terms, unless otherwise indicated.
The term "halo" or "halogen" as used herein includes fluoro, bromo, chloro or iodo unless otherwise indicated.
The term "alkyl" or "alkyl group" as used herein has a single bond of 1 to 60 carbon atoms, unless otherwise specified, and means a saturated aliphatic functionality, including a straight chain alkyl group, a branched alkyl group, a cycloalkyl group (alicyclic), a cycloalkyl group substituted with an alkyl group, or an alkyl group substituted with a cycloalkyl group.
The term "alkenyl" or "alkynyl" as used herein has a double or triple bond of 2 to 60 carbon atoms, unless otherwise specified, but is not limited thereto and includes straight or branched chain groups.
The term "cycloalkyl" as used herein means, unless otherwise specified, an alkyl group forming a ring having 3 to 60 carbon atoms, but is not limited thereto.
The term "alkoxy", "alkoxy group" or "alkyloxy group" as used herein means that an oxy group is attached to an alkyl group, but is not limited thereto, and has from 1 to 60 carbon atoms, unless otherwise specified.
The term "aryloxy group" or "aryloxy group" as used herein means that an oxy group is attached to an aryl group, but is not limited thereto, and has 6 to 60 carbon atoms, unless otherwise specified.
The terms "aryl group" and "arylene group" as used in the present invention have 6 to 60 carbon atoms, respectively, unless otherwise indicated, but are not limited thereto. In the present invention, an aryl group or arylene group means a monocyclic or polycyclic aromatic group and includes an aromatic ring formed by linking or participating in a reaction through adjacent substituents.
For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.
The prefix "aryl" or "aryl" means a group substituted with an aryl group. For example, an arylalkyl group may be an alkyl group substituted with an aryl group, and an arylalkenyl group may be an alkenyl group substituted with an aryl group, with the aryl-substituted group having the number of carbon atoms as defined herein.
Furthermore, when the prefixes are named sequentially, this means that the substituents are listed in the order first described. For example, arylalkoxy means alkoxy substituted with aryl, alkoxycarbonyl means carbonyl substituted with alkoxy, and arylcarbonylalkenyl also means alkenyl substituted with arylcarbonyl, wherein arylcarbonyl may be carbonyl substituted with aryl.
The term "heterocyclic group" as used herein contains one or more heteroatoms, but is not limited thereto, having from 2 to 60 carbon atoms, including any of monocyclic and polycyclic, and may include heteroalicyclic and heteroaromatic rings, unless otherwise specified. In addition, it is also possible to combine with adjacent groups to form heterocyclic groups.
The term "heteroatom" as used herein means at least one of N, O, S, P or Si unless otherwise specified.
Furthermore, the term "heterocyclic group" may include a ring comprising SO 2 instead of the carbon constituting the ring. For example, "heterocyclic group" includes the following compounds.
Unless otherwise indicated, the term "fluorenyl group" or "fluorenylene group" as used herein means a monovalent or divalent functional group in which both R, R ' and R "are hydrogen in the following structure, and the term" substituted fluorenyl group "or" substituted fluorenylene group "means that at least one of the substituents R, R ', R" is a substituent other than hydrogen, and includes those in which R and R ' are bonded to each other to form a spiro compound together with the carbon to which they are bonded.
The term "spiro compound" as used herein has a "spiro" and spiro means a connection in which two rings share only one atom. At this time, the atoms shared in both rings are referred to as "spiro atoms", and these compounds are referred to as "mono-, bi-, and" trispiro- "respectively, depending on the number of spiro atoms in the compound.
The term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the term "aliphatic ring" as used herein means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms, unless otherwise specified.
The term "ring" as used herein means an aliphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6 to 60 carbon atoms, or a heterocyclic ring having 2 to 60 carbon atoms, or a condensed ring formed by a combination thereof, and includes saturated or unsaturated rings, unless otherwise specified.
In addition to the hetero compounds mentioned above, other hetero compounds or groups include, but are not limited to, one or more heteroatoms.
Further, unless specifically stated otherwise, the term "substituted" in "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from deuterium, halogen, amino groups, nitrile groups, nitro groups, C 1-C20 alkyl groups, C 1-C20 alkoxy groups, C 1-C20 alkylamino groups, C 1-C20 alkylthiophene groups, C 6-C20 arylthiophene groups, C 2-C20 alkenyl groups, C 2-C20 alkynyl groups, C 3-C20 cycloalkyl groups, C 6-C20 aryl groups, C 6-C20 aryl groups substituted with deuterium, C 8-C20 arylalkenyl groups, silane groups, boron groups, germanium groups, and C 2-C20 heterocyclic groups, but is not limited to these substituents.
In addition, unless explicitly explained, the formulae used in the present invention are the same as the definition of substituents defined by the indices of the following formulae.
Here, when a is an integer of 0, the substituent R 1 is absent, when a is an integer of 1, the unique substituent R 1 is attached to any one of carbons constituting the benzene ring, when a is an integer of 2 or 3, each of which is combined in such a manner that R 1 may be the same or different from each other, when a is an integer of 4 to 6, it is bonded to a carbon of the benzene ring in a similar manner, but an indication of hydrogen bonded to a carbon forming the benzene ring is omitted.
Hereinafter, a laminated structure of an organic electronic device including the compound of the present invention will be described with reference to fig. 1 to 3.
Where reference numerals are added to elements of each figure, it should be noted that even if identical elements are indicated on different figures, the identical elements should have the same numerals as much as possible.
In addition, in describing the present invention, when it is determined that detailed description of related known configurations or functions may obscure the subject matter of the present invention, detailed description thereof will be omitted.
Fig. 1 to 3 illustrate examples of organic electronic elements according to embodiments of the present invention.
Referring to fig. 1, an organic electronic element (100) according to an embodiment of the present invention includes a first electrode (110) formed on a substrate (not shown), a second electrode (170), and an organic material layer formed between the first electrode (110) and the second electrode (170).
The first electrode (110) may be an anode, the second electrode (170) may be a cathode, and in the case of an inverted type, the first electrode may be a cathode, and the second electrode may be an anode.
The organic material layer may include a hole injection layer (120), a hole transport layer (130), a light emitting layer (140), an electron transport layer (150), and an electron injection layer (160). Specifically, a hole injection layer (120), a hole transport layer (130), a light emitting layer (140), an electron transport layer (150), and an electron injection layer (160) may be sequentially formed on the first electrode (110).
The present invention may further include a light efficiency enhancing layer formed on a side of the first electrode (110) or the second electrode (170) that is not in contact with the organic material layer, and when the light efficiency enhancing layer (180) is formed, the light efficiency of the organic electronic element may be improved.
For example, a light efficiency enhancing layer (180) may be formed on the second electrode (170), and in the case of a top emission organic light emitting device, the light efficiency enhancing layer (180) is formed, thereby reducing light energy loss due to surface plasmons (SPPs) in the second electrode (170), and in the case of a bottom emission organic light emitting device, the light efficiency enhancing layer (180) may serve as a buffer for the second electrode (170).
The buffer layer (210) or the light emitting auxiliary layer (220) may be further formed between the hole transport layer (130) and the light emitting layer (140), which will be described with reference to fig. 2.
Referring to fig. 2, an organic electronic device (200) according to another embodiment of the present invention includes a hole injection layer (120), a hole transport layer (130), a buffer layer (210), a light emitting auxiliary layer (220), a light emitting layer (140), an electron transport layer (150), an electron injection layer (160), a second electrode (170), and a light efficiency enhancing layer (180) formed on the second electrode, which are sequentially formed on the first electrode (110).
Although not shown in fig. 2, an electron transport auxiliary layer may be further formed between the light emitting layer (140) and the electron transport layer (150).
Further, according to another embodiment of the present invention, the organic material layer may have a plurality of stacks including a hole transport layer, a light emitting layer, and an electron transport layer. This will be described with reference to fig. 3.
Referring to fig. 3, in an organic electronic element (300) according to another embodiment of the present invention, 2 or more sets of stacks (ST 1 and ST 2) made of a plurality of organic material layers may be formed between a first electrode (110) and a second electrode (170), and a Charge Generation Layer (CGL) may be formed between the stacks of organic material layers.
Specifically, the organic electronic element according to an embodiment of the present invention includes a first electrode (110), a first stack (ST 1), a Charge Generation Layer (CGL), a second stack (ST 2), and a second electrode (170), and may include a light efficiency enhancement layer (180).
The first stack (ST 1) is an organic material layer formed on the first electrode (110) and may include a first hole injection layer (320), a first hole transport layer (330), a first light emitting layer (340), and a first electron transport layer (350), and the second stack (ST 2) may include a second hole injection layer (420), a second hole transport layer (430), a second light emitting layer (440), and a second electron transport layer (450). As described above, the first stack and the second stack may be organic material layers having the same laminate structure, or may be organic material layers having different laminate structures.
The Charge Generation Layer (CGL) may be formed between the first stack (ST 1) and the second stack (ST 2). The Charge Generation Layer (CGL) may include a first charge generation layer (360) and a second charge generation layer (361). A Charge Generation Layer (CGL) is formed between the first light emitting layer (340) and the second light emitting layer (440) to increase current efficiency generated in each light emitting layer and smoothly distribute charges.
When a plurality of light emitting layers are formed by a multilayer stack structure method as shown in fig. 3, an organic electronic element that emits white light by a mixing effect of light emitted from each light emitting layer, and an organic electronic element that emits light of various colors can be manufactured.
The compounds represented by formula 1 and formula 2 of the present invention may be used as materials of the hole injection layer (120, 320, 420), the hole transport layer (130, 330, 430), the buffer layer (210), the light emission auxiliary layer (220), the electron transport layer (150, 350, 450), the electron injection layer (160), the light emitting layer (140, 340, 440), or the light efficiency enhancing layer (180), but preferably, the compounds represented by formula 1 and formula 2 of the present invention may be used as hosts of the light emitting layer (140, 340, 440).
Otherwise, even if the same or similar cores are used, the band gap, electrical characteristics, interface characteristics, etc. may vary depending on where substituents are bonded, and therefore, the selection of cores and the combination of sub-substituents associated therewith are also very important, and especially when an optimal combination of energy levels and T1 values of the respective organic material layers and unique properties of the materials (mobility, interface characteristics, etc.) is achieved, both a long service life and high efficiency may be achieved.
Organic electronic elements according to embodiments of the present invention may be fabricated using various deposition methods. It may be manufactured using a vapor deposition method such as PVD or CVD. For example, after forming the anode (110) by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate and forming an organic material layer including a hole injection layer (120), a hole transport layer (130), a light emitting layer (140), an electron transport layer (150), and an electron injection layer (160) thereon, an organic electroluminescent device according to an embodiment of the present invention may be manufactured by depositing a material that can be used as the cathode (170) thereon. Further, a light emitting auxiliary layer (220) may be formed between the hole transporting layer (130) and the light emitting layer (140), and an electron transporting auxiliary layer (not shown) may be formed between the light emitting layer (140) and the electron transporting layer (150), and may be formed in a stacked structure as described above.
In addition, the organic material layer may be manufactured with a smaller number of layers by using various polymer materials and not by a deposition method, but by a solution process, a solvent process such as a spin coating process, a nozzle printing process, an inkjet printing process, a slit coating process, a dip coating process, or a roll-to-roll process, a doctor blade process, a screen printing process, or a thermal transfer method. Since the organic material layer according to the present invention may be formed by various methods, the scope of the present invention is not limited by the forming method.
In addition, the organic electronic device according to the embodiment of the present invention may be selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device, and a quantum dot display device.
Another embodiment of the present invention may include an electronic device including a display device including an organic electronic element; and a control unit for driving the display device. At this time, the electronic device may be a current or future wired/wireless communication terminal, and encompasses all kinds of electronic devices including mobile communication terminals such as cellular phones, personal Digital Assistants (PDAs), electronic dictionaries, point-to-multipoint (PMPs), remote controllers, navigation units, game consoles, various kinds of televisions, and various kinds of computers.
Hereinafter, an organic electronic element according to aspects of the present invention will be described.
The present invention provides a compound represented by formula (1).
Wherein:
A is a substituent represented by the formula (A-1); or a substituent represented by the formula (A-2);
r 1、R2、R3、R4 and R 5 are the same or different from each other and each independently represent hydrogen; or deuterium;
a and b are each independently an integer of 0 to 4, c is an integer of 0 to 7, d is an integer of 0 to 6, e is an integer of 0 to 5,
L a is a direct bond; or a C 6-C60 arylene group;
Where L a is an arylene group, it is preferably a C 6-C30 arylene group, more preferably a C 6-C24 arylene group, e.g., it may be phenylene, biphenyl, naphthalene, terphenyl, and the like.
Ar a is a C 6-C60 aryl group, which is preferably a C 6-C30 aryl group, more preferably a C 6-C24 aryl group, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, and the like.
Wherein the aryl group or arylene group may be substituted with one or more substituents selected from deuterium; halogen; a silane group; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; a C 1-C20 alkylthio group; a C 1-C20 alkoxy group; a C 1-C20 alkyl group; a C 2-C20 alkenyl group; a C 2-C20 alkynyl group; a C 6-C20 aryl group; a C 6-C20 aryl group substituted with deuterium; fluorenyl groups; a C 2-C20 heterocyclic group; a C 3-C20 cycloalkyl group; a C 7-C20 arylalkyl group; and a C 8-C20 arylalkenyl group; in addition, substituents may bond to each other to form a saturated or unsaturated ring, wherein the term "ring" means a C 3-C60 aliphatic ring or a C 6-C60 aromatic ring or a C 2-C60 heterocyclic group or a fused ring formed by a combination thereof.
Further, formula (1) is represented by formula (1-1) or formula (1-2)
Wherein:
r 1、R2、R3、R4、R5、a、b、c、d、e、La and Ar a are the same as defined above.
Further, formula (1) is represented by any one of formulas (2-1) to (2-6).
Wherein:
r 1、R2、R3、R4、R5、a、b、c、d、e、La and Ar a are the same as defined above.
In addition, ar a is represented by any one of the formulas (A-1) to (A-3).
Wherein:
* The bonding position is indicated by the number of the bonding sites,
R 6、R7 and R 8 are each the same or different and are each independently hydrogen; deuterium; or a C 6-C36 aryl group;
When R 6、R7 and R 8 are aryl groups, it is preferably a C 6-C30 aryl group, more preferably a C 6-C24 aryl group, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, and the like.
F is an integer of 0 to 5, g is an integer of 0 to 7, and h is an integer of 0 to 9.
In addition, L a is represented by any one of the formulas (L-1) to (L-3)
Wherein:
* The bonding position is indicated by the number of the bonding sites,
R 9、R10、R11 and R 12 are each the same or different and are each independently hydrogen; deuterium; or a C 6-C36 aryl group,
When R 9、R10、R11 and R 12 are aryl groups, it is preferably a C 6-C30 aryl group, more preferably a C 6-C24 aryl group, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, and the like.
I. k and l are each independently integers from 0 to 4, and j is an integer from 0 to 6.
L a is represented by any one of the following formulas (L-1) to (L-14):
Wherein:
* The bonding position is indicated by the number of the bonding sites,
R 9 and R 10 are as defined above,
I is an integer from 0 to 4, and j is an integer from 0 to 6.
Further, the compound represented by formula 1 is represented by any one of the following P-1 to P-98:
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The RE value of the compound represented by formula (1) is preferably 0.21 to 0.298, more preferably 0.22 to 0.293.
Recombination energy refers to energy lost due to a change in the molecular structural arrangement when charges (electrons, holes) move. It depends on the molecular geometry, and the smaller the difference between PES (potential energy surface) in the neutral state and PES in the charge state, the smaller the value becomes. RE value can be obtained by the following formula.
RE The cavity :λ+＝(ENOCE-ECOCE)+(ECONE-ENONE)
RE Electronic device :λ-＝(ENOAE-EAOAE)+(EAONE-ENONE)
Each factor is described as NONE: neutral geometry of neutral molecule (=no opt.), NOAE: anionic geometry of neutral molecule, NOCE: cationic geometry of neutral molecule, AONE: neutral geometry of anionic molecule AOAE: anionic geometry of anionic molecule (=ao opt.), CONE: neutral geometry of the cationic molecule COCE: cationic geometry of cationic molecule (=co opt.)
The recombination energy value and mobility are inversely proportional to each other, and the RE value of each material directly affects mobility under the condition that they have the same r and T values. The relationship between RE value and mobility is expressed as follows.
Each factor is described as λ: recombinant energy/μ: mobility/r: dimer substitution/t: intermolecular charge transfer matrix elements. From the above equation, it can be seen that the lower the RE value, the faster the mobility.
The recombinant energy values require a simulation tool capable of calculating potential energy from molecular structure, we use the Gaussian09 (hereinafter G09) and Jaguar (hereinafter JG) modules of Schrodinger Materials Science (Schrodinger Materials Science). Both G09 and JG are tools for analyzing molecular properties by Quantum Mechanical (QM) calculations and have the function of optimizing molecular structure or calculating energy (single point energy) for a given molecular structure.
The process of performing QM calculations in a molecular architecture requires a large amount of computational resources, and we company use 2 cluster servers to do these calculations. Each cluster server consists of 4 node workstations and 1 master workstation, each node performing molecular QM computations by Symmetric Multiprocessing (SMP) parallel computation using more than 36 cores of CPU.
The potential energy in the neutral/charge state (NONE/COCE) required to optimize the molecular structure and its rearrangement energy was calculated using G09. The charge state potential energy (NOCE) of the structure optimized for the neutral state and the neutral state potential energy (CONE) of the structure optimized for the charge state are calculated by changing the charge to only 2 optimized structures. Then, the rearrangement energy is calculated according to the following relational expression.
RE Electric charge :λ＝(ENOCE-ECOCE)+(ECONE-ENONE)
Since schrodinger provides a function of automatically performing such a calculation process, potential energy according to each state is sequentially calculated through the JG module by providing a molecular structure (NO) of a ground state, and an RE value is calculated.
According to an embodiment of the invention, more electrons are attracted to elements having greater electronegativity in two atoms in one covalent bond. Here, atoms of relatively high electronegativity have δ -charges, and atoms of low electronegativity have δ+ charges. As described above, the difference in polarity of two atoms is referred to as a dipole. At this time, the dipole moment can be calculated as a vector quantity by multiplying the intensities of the two poles by the distance between the two nuclei. In other words, the dipole moment can be calculated by the following equation.
μ＝δ*d
Each factor is the distance μ between: dipole moment/delta: size/d of partial charges δ + and δ –: delta + and delta –.
We used G09 to optimize the molecular structure of B3LYP/6-31G (d). Based on the results, a maliken (Mulliken) charge value for each atom is obtained, and the dipole moment is calculated by multiplying the axial vectors. The dipole moment is the vector sum of the dipole moments of each bond. The dipole moment value means the magnitude of the vector dipole moment, and it can be expressed as a value of the following vector length.
Further, the present invention relates to an organic electronic element including a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, wherein the light emitting layer is a phosphorescent light emitting layer, and provides an organic electronic element including a first host compound represented by formula 1 and a second host compound represented by formula 2 or formula 3.
Wherein:
L 4、L5、L6 and L 7 are each independently selected from single bonds; a C 6-C60 arylene group; fluorenylene groups; a fused ring group of a C 3-C60 aliphatic ring and a C 6-C60 aromatic ring; a C 2-C60 heterocyclic group;
Where L 4、L5、L6 and L 7 are arylene groups, it is preferably a C 6-C30 arylene group, more preferably a C 6-C24 arylene group, e.g., it may be phenylene, biphenyl, naphthalene, terphenyl, and the like.
When L 4、L5、L6 and L 7 are heterocyclic groups, it is preferably a C 2-C30 heterocyclic group, and more preferably a C 2-C24 heterocyclic group, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido [5,4-b ] indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothiophenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine.
When L 4、L5、L6 and L 7 are fused ring groups, it is preferably a fused ring group of a C 3-C30 aliphatic ring and a C 6-C30 aromatic ring, and more preferably a fused ring group of a C 3-C24 aliphatic ring and a C 6-C24 aromatic ring.
Ar 3、Ar4 and Ar 5 are each independently selected from C 6-C60 aryl groups; fluorenyl groups; a C 2-C60 heterocyclic group comprising at least one heteroatom of O, N, S, si or P; and fused ring groups of C 3-C60 aliphatic and C 6-C60 aromatic rings;
Ar 6 is each independently selected from the group consisting of C 6-C60 aryl groups; fluorenyl groups; a C 2-C60 heterocyclic group comprising at least one heteroatom of O, N, S, si or P; a fused ring group of a C 3-C60 aliphatic ring and a C 6-C60 aromatic ring; and-L' -N (R b)(Rc);
When Ar 3、Ar4、Ar5 and Ar 6 are aryl groups, it is preferably a C 6-C30 aryl group, more preferably a C 6-C24 aryl group, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, and the like.
When Ar 3、Ar4、Ar5 and Ar 6 are heterocyclic groups, it is preferably a C 2-C30 heterocyclic group, and more preferably a C 2-C24 heterocyclic group, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido [5,4-b ] indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothiophenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine.
When Ar 3、Ar4、Ar5 and Ar 6 are fused ring groups, it is preferably a fused ring group of a C 3-C30 aliphatic ring and a C 6-C30 aromatic ring, and more preferably a fused ring group of a C 3-C24 aliphatic ring and a C 6-C24 aromatic ring,
Wherein L' is selected from single bonds; a C 6-C60 arylene group; a C 2-C60 heterocyclic group comprising at least one heteroatom of O, N, S, si or P;
Wherein R b and R c are each independently selected from C 6-C60 aryl groups; fluorenyl groups; a fused ring group of a C 3-C60 aliphatic ring and a C 6-C60 aromatic ring; a C 2-C60 heterocyclic group comprising at least one heteroatom of O, N, S, si or P; a C 1-C50 alkyl group; a C 2-C20 alkenyl group; a C 2-C20 alkynyl group; a C 1-C30 alkoxy group; a C 6-C30 aryloxy group;
z is O, S, CR 'R' or NRa,
B is a C 6-C20 aryl group,
R 'and R' are each independently selected from C 6-C60 aryl groups; fluorenyl groups; a C 2-C60 heterocyclic group comprising at least one heteroatom of O, N, S, si or P; a fused ring group of a C 3-C60 aliphatic ring and a C 6-C60 aromatic ring; a C 1-C50 alkyl group; a C 2-C20 alkenyl group; a C 2-C20 alkynyl group; a C 1-C30 alkoxy group; and a C 6-C30 aryloxy group; or may be bonded to each other to form a ring,
R 31 and R 32 are each independently the same or different from each other and are each independently selected from hydrogen; deuterium; halogen; a cyano group; a nitro group; a C 6-C60 aryl group; fluorenyl groups; a C 2-C60 heterocyclic group comprising at least one heteroatom of O, N, S, si or P; a fused ring group of a C 3-C60 aliphatic ring and a C 6-C60 aromatic ring; a C 1-C60 alkyl group; a C 2-C60 alkenyl group; a C 2-C60 alkynyl group; a C 1-C60 alkoxy group; and a C 6-C60 aryloxy group; or a plurality of adjacent R 31 or a plurality of R 32 may be bonded to each other to form a ring,
N and o are each independently integers from 0 to 4,
When R', R ", R 31 and R 32 are aryl groups, it is preferably a C 6-C30 aryl group, more preferably a C 6-C24 aryl group, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, etc.
When R', R ", R 31 and R 32 are heterocyclic groups, it is preferably a C 2-C30 heterocyclic group, and more preferably a C 2-C24 heterocyclic group, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido [5,4-b ] indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothiophenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine.
When R', R ", R 31 and R 32 are fused ring groups, it is preferably a fused ring group of a C 3-C30 aliphatic ring and a C 6-C30 aromatic ring, and more preferably a fused ring group of a C 3-C24 aliphatic ring and a C 6-C24 aromatic ring,
When R', R ", R 31 and R 32 are alkyl groups, it is preferably a C 1-C30 alkyl group, and more preferably a C 1-C24 alkyl group.
When R ', R', R 31 and R 32 are alkoxy groups, it is preferably a C 1-C24 alkoxy group.
When R ', R', R 31 and R 32 are aryloxy groups, it is preferably a C 1-C24 aryloxy group.
Ra is a C 6-C60 aryl group; or a C 2-C60 heterocyclic group comprising at least one heteroatom of O, N, S, si and P;
When Ra is an aryl group, it is preferably a C 6-C30 aryl group, more preferably a C 6-C24 aryl group, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, or the like.
When Ra is a heterocyclic group, it is preferably a C 2-C30 heterocyclic group, and more preferably a C 2-C24 heterocyclic group, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido [5,4-b ] indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, benzothiophenopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine.
Wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, and aryloxy group may be substituted with one or more substituents selected from deuterium; halogen; a silane group; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; a C 1-C20 alkylthio group; a C 1-C20 alkoxy group; a C 1-C20 alkyl group; a C 2-C20 alkenyl group; a C 2-C20 alkynyl group; a C 6-C20 aryl group; a C 6-C20 aryl group substituted with deuterium; fluorenyl groups; a C 2-C20 heterocyclic group; a C 3-C20 cycloalkyl group; a C 7-C20 arylalkyl group; and a C 8-C20 arylalkenyl group; and further, substituents may bond to each other to form a saturated or unsaturated ring, wherein the term "ring" means a C 3-C60 aliphatic ring or a C 6-C60 aromatic ring or a C 2-C60 heterocyclic group or a condensed ring formed by a combination thereof.
Formula 2 is represented by any one of formulas 2-1 to 2-3.
Wherein:
Ar 4、Ar5、L4、L5 and L 6 are the same as defined in formula 2,
X 1、X2 and X 3 are as defined for Z.
R 13、R14、R15、R16、R17 and R 18 are as defined for R 31, or a plurality of adjacent R 13 or R 14 or R 15 or R 16 or R 17 or R 18 may be bonded to each other to form a ring,
P, r and t are integers from 0 to 4, and q, s and u are each independently integers from 0 to 3.
Formula 3 is represented by any one of formulas 3-1 to 3-6.
Wherein:
Z, R 31、R32、Ar6、L7, n, o are as defined in formula 3,
R 19 is as defined for R 31,
V is an integer from 0 to 2.
Formula 3 is represented by any one of formulas 3-7 to 3-9.
Wherein:
Z, B, R 32、o、Ar6 and L 7 are the same as defined in formula 3,
R 20 is as defined above for R 31,
W is an integer of 0 to 6
Formula 3 is represented by any one of formulas 3-10 to 3-12.
Wherein:
z, B, ar 6、L7、R31 and n are the same as defined in formula 3,
R 21 is as defined for R 31,
X is an integer from 0 to 6.
Formula 3 is represented by formula 3-13 to formula 3-18
Wherein:
y, L 7、Ar6、R31、R32, n and o are as defined in formula 3,
R 19、R20 and R 21 are as defined for R 31,
V is an integer from 0 to 2, w and x are each independently an integer from 0 to 6.
Formula 3 is represented by formulas 3-19:
< 3-19>
Wherein:
L 7、Ar6、Ra、R32 and o are as defined in formula 3,
R 19 and R 20 are as defined for R 31,
V is an integer from 0 to 2 and w is an integer from 0 to 6.
Further, the compound represented by formula 2 is any one of the following compounds N-1 to N-96.
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Further, the compound represented by formula 3 is any one of the following compounds S-1 to S-108.
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The present invention may further include a light efficiency enhancing layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer.
Further, the organic material layer may include 2 or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the anode, and the organic material layer may further include a charge generation layer formed between the 2 or more stacks.
In another aspect, the present invention provides an electronic device comprising a display device comprising an organic electronic element; a control unit for driving the display device; the organic electronic component is at least one of an OLED, an organic solar cell, an organic photoconductor, an organic transistor, and a component for monochromatic or white illumination.
Hereinafter, examples of synthesis of the compound represented by formula according to the present invention and examples of manufacture of the organic electronic element according to the present invention will be described in detail by examples, but are not limited to the following examples of the present invention.
Synthesis example
The compound (final product) represented by formula (1) according to the present invention may be synthesized by reacting Sub1 and Sub2 as shown in scheme 1, but is not limited thereto.
< Reaction scheme 1>
Synthesis of sub 1
Sub 1 of reaction scheme 1 may be synthesized through the reaction pathway of reaction scheme 2, but is not limited thereto.
< Reaction scheme 2>
The synthesis of specific compounds belonging to Sub 1 is for example as follows.
Synthesis example of sub1-1
(1) Synthesis of Sub1-1b
Sub1-1a(40.84g,221.49mmol)、Sub2-36(30.00g,73.83mmol)、Pd(PPh3)4(2.56g,2.21mmol)、NaOH(5.91g,147.66mmol) Was placed in a round bottom flask, 246mL of anhydrous THF and 81mL of water were added and dissolved, followed by reflux for 12 hours. When the reaction was complete, the reaction was cooled to room temperature, extracted with CH 2Cl2 and water, and then treated with MgSO 4. The organic solvent was concentrated and the resulting product was recrystallized using a silica gel column to obtain 24.00g (80%) of Sub1-1b.
(2) Synthesis of Sub1-1
The obtained Sub1-1b (23.93 g,55.87 mmol) and Sub2-26 (12.30 g,37.25 mmol), pd (PPh 3)4 (1.29 g,1.12 mmol), naOH (2.98 g,74.49 mmol) were dissolved in 124mL THF and 40mL water and stirred at 60℃for 12 hours in a round bottom flask when the reaction was completed, the reaction was cooled to room temperature, extracted with CH 2Cl2 and water, and then treated with MgSO 4 the organic solvent was concentrated and the resulting product recrystallized using a silica gel column to obtain 16.00g (74%) of Sub1-1.
Synthesis example of sub1-2
The obtained Sub1-1b (23.93 g,55.87 mmol) and Sub2-37 (12.30 g,37.25 mmol), pd (PPh 3)4 (1.29 g,1.12 mmol), naOH (2.98 g,74.49 mmol) were dissolved in 124mL THF and 40mL water and stirred at 60℃for 12 hours in a round bottom flask when the reaction was complete, the reaction was cooled to room temperature, extracted with CH 2Cl2 and water, and then treated with MgSO 4 the organic solvent was concentrated and the resulting product recrystallized using a silica gel column to obtain 14.43g (65%) of Sub1-2.
Synthesis example of sub1-3
The obtained Sub1-1b (23.93 g,55.87 mmol) and Sub2-38 (12.30 g,37.25 mmol), pd (PPh 3)4 (1.29 g,1.12 mmol), naOH (2.98 g,74.49 mmol) were dissolved in 124mL THF and 40mL water and stirred at 60℃for 12 hours in a round bottom flask when the reaction was complete, the reaction was cooled to room temperature, extracted with CH 2Cl2 and water, and then treated with MgSO 4 the organic solvent was concentrated and the resulting product recrystallized using a silica gel column to obtain 8.88g (40%) of Sub1-3.
Synthesis example of sub 1-5
The obtained Sub1-1b (20.95 g,48.92 mmol) and Sub2-44 (11.00 g,32.61 mmol), pd (PPh 3)4 (1.13 g,0.98 mmol), naOH (2.61 g,65.23 mmol) were dissolved in 109mL THF and 35mL water and stirred at 60℃for 12 hours in a round bottom flask when the reaction was completed, the reaction was cooled to room temperature, extracted with CH 2Cl2 and water, and then treated with MgSO 4 the organic solvent was concentrated and the resulting product recrystallized using a silica gel column to obtain 15.74g (80%) of Sub1-5.
Synthesis example of sub1-7
(1) Synthesis of Sub1-2b
Sub1-1a(53.79g,291.72mmol)、Sub2-40(40.00g,97.24mmol)、Pd(PPh3)4(3.37g,2.92mmol)、NaOH(7.78g,194.48mmol) Was placed in a round bottom flask, 324mL of anhydrous THF and 108mL of water were added to dissolve, and refluxed for 12 hours. When the reaction was complete, the reaction was cooled to room temperature, extracted with CH 2Cl2 and water, and then treated with MgSO 4. The organic solvent was concentrated and the resulting product was recrystallized using a silica gel column to obtain 27.39g (64%) of Sub1-2b.
(2) Synthesis of Sub1-7
The obtained Sub1-2b (19.27 g,44.47 mmol) and Sub2-43 (10.00 g,29.65 mmol), pd (PPh 3)4 (1.03 g,0.89 mmol), naOH (2.37 g,59.30 mmol) were dissolved in 99mL THF and 33mL water and stirred at 60℃for 12 hours.
Synthesis example of sub 1-9
The obtained Sub1-2b (25.59 g,59.05 mmol) and Sub2-37 (13.00 g,39.37 mmol), pd (PPh 3)4 (1.37 g,1.18 mmol), naOH (3.15 g,78.73 mmol) were dissolved in 131mL of THF and 41mL of water and stirred at 60℃for 12 hours.
Synthesis example of sub1-11
(1) Synthesis of Sub1-3b
Sub1-1a(47.65g,258.41mmol)、Sub2-46(35.00g,86.14mmol)、Pd(PPh3)4(2.99g,2.58mmol)、NaOH(6.89g,172.27mmol) Was placed in a round bottom flask, 290mL of anhydrous THF and 96mL of water were added to dissolve, and refluxed for 12 hours. When the reaction was complete, the reaction was cooled to room temperature, extracted with CH 2Cl2 and water, and then treated with MgSO 4. The organic solvent was concentrated and the resulting product was recrystallized using a silica gel column to obtain 29.52g (80%) of Sub1-3b
(2) Synthesis of Sub1-11
The obtained Sub1-3b (27.24 g,63.59 mmol) and Sub2-37 (14.00 g,42.39 mmol), pd (PPh 3)4 (1.47 g,1.27 mmol), naOH (3.39 g,84.79 mmol) were dissolved in 141mL THF and 50mL water and stirred at 60℃for 12 hours in a round bottom flask when the reaction was completed, the reaction was cooled to room temperature, extracted with CH 2Cl2 and water, and then treated with MgSO 4 the organic solvent was concentrated and the resulting product recrystallized using a silica gel column to obtain 19.21g (76%) of Sub1-11.
Synthesis example of sub1-13
(1) Synthesis of Sub1-4b
Sub1-1a(40.34g,218.79mmol)、Sub2-47(30.00g,72.93mmol)、Pd(PPh3)4(2.53g,2.19mmol)、NaOH(5.83g,145.86mmol) Was placed in a round bottom flask, 243mL of anhydrous THF and 81mL of water were added to dissolve, and refluxed for 12 hours. When the reaction was complete, the reaction was cooled to room temperature, extracted with CH 2Cl2 and water, and then treated with MgSO 4. The organic solvent was concentrated and the resulting product was recrystallized using a silica gel column to obtain 19.59g (62%) of Sub1-4b
(2) Synthesis of Sub1-13
The obtained Sub1-4b (15.75 g,36.34 mmol) and Sub2-26 (8.00 g,24.23 mmol), pd (PPh 3)4 (0.84 g,0.73 mmol), naOH (1.94 g,48.45 mmol) were dissolved in 80mL THF and 26mL water and stirred at 60℃for 12 hours.
Synthesis example of sub 1-14
The obtained Sub1-3b (26.67 g,62.26 mmol) and Sub2-43 (14.00 g,41.51 mmol), pd (PPh 3)4 (1.44 g,1.25 mmol), naOH (3.32 g,83.02 mmol) were dissolved in 138mL of THF and 46mL of water and stirred at 60℃for 12 hours in a round bottom flask when the reaction was completed, the reaction was cooled to room temperature, extracted with CH 2Cl2 and water, and then treated with MgSO 4 the organic solvent was concentrated and the resulting product recrystallized using a silica gel column to obtain 17.17g (68%) of Sub1-14.
In addition, the compound belonging to Sub 1 may be the following compound, but is not limited thereto, and table 1 shows FD-MS (field desorption-mass spectrometry) values of the compound belonging to Sub 1.
TABLE 1
| Compounds of formula (I) | FD-MS | Compounds of formula (I) | FD-MS |
| Sub1-1 | m/z＝595.18(C41H26ClN3＝596.13) | Sub1-2 | m/z＝595.18(C41H26ClN3＝596.13) |
| Sub1-3 | m/z＝595.18(C41H26ClN3＝596.13) | Sub1-4 | m/z＝601.22(C41H20D6ClN3＝602.17) |
| Sub1-5 | m/z＝602.23(C41H19D7ClN3＝603.17) | Sub1-6 | m/z＝599.21(C41H22D4ClN3＝600.15) |
| Sub1-7 | m/z＝606.25(C41H15D11ClN3＝607.2) | Sub1-8 | m/z＝600.21(C41H21D5ClN3＝601.16) |
| Sub1-9 | m/z＝600.21(C41H21D5ClN3＝601.16) | Sub1-10 | m/z＝595.18(C41H26ClN3＝596.13) |
| Sub1-11 | m/z＝595.18(C41H26ClN3＝596.13) | Sub1-12 | m/z＝595.18(C41H26ClN3＝596.13) |
| Sub1-13 | m/z＝600.21(C41H21D5ClN3＝601.16) | Sub1-14 | m/z＝602.23(C41H19D7ClN3＝603.17) |
| Sub1-15 | m/z＝599.21(C41H22D4ClN3＝600.15) | Sub1-16 | m/z＝599.21(C41H22D4ClN3＝600.15) |
| Sub1-17 | m/z＝605.24(C41H16D10ClN3＝606.19) |
Synthesis of sub 2
Sub 2 of scheme 1 can be synthesized through the pathway of reaction scheme 3, but is not limited thereto. Hal1=cl, br
< Reaction scheme 3>
The synthesis of specific compounds belonging to Sub 2 is for example as follows.
Synthesis example of sub 2-1
Sub2-1a (10.00 g,63.69 mmol), 4', 5',5 '-octamethyl-2, 2' -bis (1, 3, 2-dioxaborolan) (21.03 g,82.80 mmol), pd 2(dba)3 (1.75 g,1.91 mmol), acOK (12.50 g,127.38 mmol) was added to DMF (212 mL) and stirred at 160℃for 4 hours. After the completion of the reaction, the reaction solvent was removed, and the concentrated organic material was passed through a silica gel column or recrystallized to obtain 8.45g (65%) of the product Sub2-1.
Synthesis example of sub 2-2
Sub2-2a (10.00 g,48.29 mmol), 4', 5',5 '-octamethyl-2, 2' -bis (1, 3, 2-dioxaborolan) (15.94 g,62.78 mmol), pd 2(dba)3 (1.33 g,1.45 mmol), acOK (9.48 g,96.59 mmol) was added to DMF (161 mL) and stirred at 160℃for 4 hours. After the completion of the reaction, the reaction solvent was removed, and the concentrated organic material was passed through a silica gel column or recrystallized to obtain 7.36g (60%) of product Sub2-2.
Synthesis example of sub 2-7
Sub2-7a (10.00 g,41.89 mmol), 4', 5',5 '-octamethyl-2, 2' -bis (1, 3, 2-dioxaborolan) (13.83 g,54.46 mmol), pd 2(dba)3 (1.15 g,1.26 mmol), acOK (8.22 g,83.78 mmol) was added to DMF (140 mL) and stirred at 160℃for 4 hours. After the completion of the reaction, the reaction solvent was removed, and the concentrated organic material was passed through a silica gel column or recrystallized to obtain 9.41g (68%) of product Sub2-7.
Synthesis example of sub 2-26
Sub2-26a (10.00 g,35.31 mmol), 4', 5',5 '-octamethyl-2, 2' -bis (1, 3, 2-dioxaborolan) (11.66 g,45.91 mmol), pd2 (dba) 3 (0.97 g,1.06 mmol), acOK (6.93 g,70.63 mmol) was added to DMF (117 mL) and stirred at 160℃for 4 hours. After the completion of the reaction, the reaction solvent was removed, and the concentrated organic material was passed through a silica gel column or recrystallized to obtain 7.35g (63%) of the product Sub2-26.
Synthesis example of sub 2-29
Sub2-29a (10.00 g,34.63 mmol), 4', 5',5 '-octamethyl-2, 2' -bis (1, 3, 2-dioxaborolan) (11.43 g,45.02 mmol), pd 2(dba)3 (0.95 g,1.04 mmol), acOK (6.80 g,69.26 mmol) was added to DMF (115 mL) and stirred at 160℃for 4 hours. After the completion of the reaction, the reaction solvent was removed, and the concentrated organic material was passed through a silica gel column or recrystallized to obtain 10.27g (78%) of the product Sub2-29.
Synthesis example of sub 2-30
Sub2-30a (10.00 g,61.71 mmol), 4', 5',5 '-octamethyl-2, 2' -bis (1, 3, 2-dioxaborolan) (20.37 g,80.23 mmol), pd 2(dba)3 (1.70 g,1.85 mmol), acOK (1.11 g,123.43 mmol) was added to DMF (206 mL) and stirred at 160℃for 4 hours. After the completion of the reaction, the reaction solvent was removed, and the concentrated organic material was passed through a silica gel column or recrystallized to obtain 9.68g (75%) of the product Sub2-30.
Synthesis example of sub 2-36
Sub2-36a (10.00 g,31.77 mmol), 4', 5',5 '-octamethyl-2, 2' -bis (1, 3, 2-dioxaborolan) (10.49 g,41.29 mmol), pd2 (dba) 3 (0.87 g,0.95 mmol), acOK (6.23 g,63.53 mmol) was added to DMF (106 mL) and stirred at 160℃for 4 hours. After the completion of the reaction, the reaction solvent was removed, and the concentrated organic material was passed through a silica gel column or recrystallized to obtain 10.33g (80%) of product Sub2-36.
Synthesis example of sub 2-40
Sub2-40a (10.00 g,31.27 mmol), 4', 5',5 '-octamethyl-2, 2' -bis (1, 3, 2-dioxaborolan) (10.32 g,40.65 mmol), pd 2(dba)3 (0.86 g,0.94 mmol), acOK (6.14 g,62.53 mmol) was added to DMF (105 mL) and stirred at 160℃for 4 hours. After the completion of the reaction, the reaction solvent was removed, and the concentrated organic material was passed through a silica gel column or recrystallized to obtain 9.00g (70%) of product Sub2-40.
Synthesis example of sub 2-43
Sub2-43a (10.00 g,34.46 mmol), 4', 5',5 '-octamethyl-2, 2' -bis (1, 3, 2-dioxaborolan) (11.38 g,44.80 mmol), pd 2(dba)3 (0.95 g,1.03 mmol), acOK (6.76 g,68.92 mmol) was added to DMF (115 mL) and stirred at 160℃for 4 hours. After the completion of the reaction, the reaction solvent was removed, and the concentrated organic material was passed through a silica gel column or recrystallized to obtain 8.60g (74%) of the product Sub2-43.
Synthesis example of sub 2-46
Sub2-46a (10.00 g,31.77 mmol), 4', 5',5 '-octamethyl-2, 2' -bis (1, 3, 2-dioxaborolan) (10.49 g,41.29 mmol), pd 2(dba)3 (0.87 g,0.95 mmol), acOK (6.23 g,63.53 mmol) was added to DMF (106 mL) and stirred at 160℃for 4 hours. After the completion of the reaction, the reaction solvent was removed, and the concentrated organic material was passed through a silica gel column or recrystallized to obtain 9.03g (70%) of the product Sub2-46.
Synthesis example of sub 2-49
Sub2-49a (10.00 g,31.27 mmol), 4', 5',5 '-octamethyl-2, 2' -bis (1, 3, 2-dioxaborolan) (10.32 g,40.65 mmol), pd 2(dba)3 (0.86 g,0.94 mmol), acOK (6.14 g,62.53 mmol) was added to DMF (105 mL) and stirred at 160℃for 4 hours. After the completion of the reaction, the reaction solvent was removed, and the concentrated organic material was passed through a silica gel column or recrystallized to obtain 10.03g (78%) of product Sub2-49.
Meanwhile, the compound belonging to Sub 2 may be, but is not limited to, the following, and table 2 shows FD-MS values of the compound belonging to Sub 2.
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TABLE 2
| Compounds of formula (I) | FD-MS | Compounds of formula (I) | FD-MS |
| Sub2-1 | m/z＝204.13(C12H17BO2＝204.08) | Sub2-2 | m/z＝254.15(C16H19BO2＝254.14) |
| Sub2-3 | m/z＝254.15(C16H19BO2＝254.14) | Sub2-4 | m/z＝280.16(C18H21BO2＝280.17) |
| Sub2-5 | m/z＝280.16(C18H21BO2＝280.17) | Sub2-6 | m/z＝280.16(C18H21BO2＝280.17) |
| Sub2-7 | m/z＝330.18(C22H23BO2＝330.23) | Sub2-8 | m/z＝330.18(C22H23BO2＝330.23) |
| Sub2-9 | m/z＝330.18(C22H23BO2＝330.23) | Sub2-10 | m/z＝330.18(C22H23BO2＝330.23) |
| Sub2-11 | m/z＝330.18(C22H23BO2＝330.23) | Sub2-12 | m/z＝330.18(C22H23BO2＝330.23) |
| Sub2-13 | m/z＝330.18(C22H23BO2＝330.23) | Sub2-14 | m/z＝330.18(C22H23BO2＝330.23) |
| Sub2-15 | m/z＝330.18(C22H23BO2＝330.23) | Sub2-16 | m/z＝330.18(C22H23BO2＝330.23) |
| Sub2-17 | m/z＝330.18(C22H23BO2＝330.23) | Sub2-18 | m/z＝330.18(C22H23BO2＝330.23) |
| Sub2-19 | m/z＝330.18(C22H23BO2＝330.23) | Sub2-20 | m/z＝330.18(C22H23BO2＝330.23) |
| Sub2-21 | m/z＝304.16(C20H21BO2＝304.2) | Sub2-22 | m/z＝304.16(C20H21BO2＝304.2) |
| Sub2-23 | m/z＝304.16(C20H21BO2＝304.2) | Sub2-24 | m/z＝304.16(C20H21BO2＝304.2) |
| Sub2-25 | m/z＝356.19(C24H25BO2＝356.27) | Sub2-26 | m/z＝330.18(C22H23BO2＝330.23) |
| Sub2-27 | m/z＝406.21(C28H27BO2＝406.33) | Sub2-28 | m/z＝406.21(C28H27BO2＝406.33) |
| Sub2-29 | m/z＝380.19(C26H25BO2＝380.29) | Sub2-30 | m/z＝209.16(C12H12D5BO2＝209.11) |
| Sub2-31 | m/z＝406.21(C28H27BO2＝406.33) | Sub2-32 | m/z＝406.21(C28H27BO2＝406.33) |
| Sub2-33 | m/z＝356.19(C24H25BO2＝356.27) | Sub2-34 | m/z＝406.21(C28H27BO2＝406.33) |
| Sub2-35 | m/z＝406.21(C28H27BO2＝406.33) | Sub2-36 | m/z＝406.21(C28H27BO2＝406.33) |
| Sub2-37 | m/z＝330.18(C22H23BO2＝330.23) | Sub2-38 | m/z＝330.18(C22H23BO2＝330.23) |
| Sub2-39 | m/z＝406.21(C28H27BO2＝406.33) | Sub2-40 | m/z＝411.24(C28H22D5BO2＝411.36) |
| Sub2-41 | m/z＝412.25(C28H21D6BO2＝412.37) | Sub2-42 | m/z＝410.24(C28H23D4BO2＝410.36) |
| Sub2-43 | m/z＝337.22(C22H16D7BO2＝337.28) | Sub2-44 | m/z＝337.22(C22H16D7BO2＝337.28) |
| Sub2-45 | m/z＝337.22(C22H16D7BO2＝337.28) | Sub2-46 | m/z＝406.21(C28H27BO2＝406.33) |
| Sub2-47 | m/z＝411.24(C28H22D5BO2＝411.36) | Sub2-48 | m/z＝412.25(C28H21D6BO2＝412.37) |
| Sub2-49 | m/z＝410.24(C28H23D4BO2＝410.36) | Sub2-50 | m/z＝415.27(C28H18D9BO2＝415.39) |
III Synthesis of the end product
1.P-1 Synthesis example
Sub1-1(29.21g,49.00mmol)、Sub2-1(10.00g,49.00mmol)、Pd(PPh3)4(1.70g,1.47mmol)、NaOH(3.92g,98.00mmol)、164mL THF and 53mL of water were added to the round bottom flask and reacted at 75℃for 8 hours. When the reaction was completed, the temperature of the reactant was cooled to room temperature, and the reaction solvent was removed. The concentrated reaction was then passed through a silica gel column and recrystallized to obtain 25.20g (81%) of product P-1.
Synthesis example of P-5
Sub1-2(25.80g,43.28mmol)、Sub2-2(11.00g,43.28mmol)、Pd(PPh3)4(1.50g,1.30mmol)、NaOH(3.46g,86.57mmol)、145mL THF and 46mL of water were added and reacted at 75℃for 8 hours. When the reaction was completed, 22.63g (76%) of product P-5 was obtained by the isolation method using P-1.
3.P-9 Synthesis example
Sub1-3(17.02g,28.55mmol)、Sub2-4(8.00g,28.55mmol)、Pd(PPh3)4(0.99g,0.86mmol)、NaOH(2.28g,57.11mmol)、96mL THF and 32mL of water were added and reacted at 75℃for 8 hours. When the reaction was completed, 17.12g (84%) of the product P-9 was obtained by the isolation method using P-1.
4.P-27 Synthesis example
Sub1-1(15.06g,25.26mmol)、Sub2-25(9.00g,25.26mmol)、Pd(PPh3)4(0.88g,0.76mmol)、NaOH(2.02g,50.52mmol)、84mL THF and 28mL of water were added and reacted at 75℃for 8 hours. When the reaction was complete, 17.56g (88%) of product P-27 was obtained by isolation using P-1.
5.P-57 Synthesis example
Sub1-5(18.99g,31.48mmol)、Sub2-3(8.00g,31.48mmol)、Pd(PPh3)4(1.09g,0.94mmol)、NaOH(2.52g,62.96mmol)、105mL THF and 34mL of water were added and reacted at 75℃for 8 hours. When the reaction was completed 18.36g (84%) of product P-57 were obtained by isolation using P-1.
Synthesis example of P-58
Sub1-3(19.96g,33.48mmol)、Sub2-30(7.00g,33.48mmol)、Pd(PPh3)4(1.16g,1.00mmol)、NaOH(2.68g,66.95mmol)、112mL THF and 37mL of water were added and reacted at 75℃for 8 hours. When the reaction was completed, 16.78g (78%) of the product P-58 was obtained by the isolation method using P-1.
Synthesis example of P-62
Sub1-9(17.67g,29.40mmol)、Sub2-1(6.00g,29.40mmol)、Pd(PPh3)4(1.02g,0.88mmol)、NaOH(2.35g,58.80mmol)、98mL THF and 32mL of water were added and reacted at 75℃for 8 hours. When the reaction was completed, 15.57g (82%) of product P-62 was obtained by the isolation method using P-1.
8.P-63 Synthesis example
Sub1-7(12.89g,21.20mmol)、Sub2-14(7.00g,21.20mmol)、Pd(PPh3)4(0.74g,0.64mmol)、NaOH(1.70g,42.39mmol)、70mL THF and 23mL of water were added and reacted at 75℃for 8 hours. When the reaction was completed, 13.98g (85%) of the product P-63 was obtained by the isolation method using P-1.
9.P-80 Synthesis example
Sub1-11(8.80g,14.77mmol)、Sub2-27(6.00g,14.77mmol)、Pd(PPh3)4(0.51g,0.44mmol)、NaOH(1.18g,29.53mmol)、50mL THF and 16mL of water were added and reacted at 75℃for 8 hours. When the reaction was completed, 8.06g (65%) of product P-80 was obtained by the isolation method using P-1.
Synthesis example of P-84
Sub1-10(12.54g,21.04mmol)、Sub2-29(8.00g,21.04mmol)、Pd(PPh3)4(0.73g,0.63mmol)、NaOH(1.68g,42.07mmol)、70mL THF and 23mL of water were added and reacted at 75℃for 8 hours. When the reaction was complete 11.98g (70%) of product P-84 were obtained by isolation using P-1.
Synthesis example of P-85
Sub1-10(9.03g,15.14mmol)、Sub2-7(5.00g,15.14mmol)、Pd(PPh3)4(0.53g,0.45mmol)、NaOH(1.21g,30.28mmol)、51mL THF and 17mL of water were added and reacted at 75℃for 8 hours. When the reaction was completed, 9.48g (82%) of product P-85 was obtained by the isolation method using P-1.
Synthesis example of P-96
Sub1-15(11.84g,19.72mmol)、Sub2-11(6.00g,19.72mmol)、Pd(PPh3)4(0.68g,0.59mmol)、NaOH(1.58g,39.45mmol)、65mL THF and 22mL of water were added and reacted at 75℃for 8 hours. When the reaction was completed, 11.26g (77%) of product P-96 was obtained by the isolation method using P-1.
Meanwhile, FD-MS values of the inventive compounds P-1 to P-98 prepared according to the above synthesis examples are shown in Table 3.
TABLE 3
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Synthesis example 2
Synthesis example of N-12
N-12a(30g,0.10mol)、N-12b(34.8g,0.08mol)、Pd2(dba)3(2.3g,0.003mol)、NaOt-Bu(24.5g,0.25mol)、P(t-Bu)3(2.1g,0.005mol)、 Toluene (170 mL) was added and reacted at 135℃for 6 hours. When the reaction was completed, 53g (85.8%) of the product N-12 was obtained by the isolation method using P-1.
Synthesis example of N-19
N-19a(50g,0.13mol)、N-19b(35g,0.13mol)、Pd2(dba)3(3.6g,0.004mol)、NaOt-Bu(37.6g,0.40mol)、P(t-Bu)3(3.2g,0.008mol)、 Toluene (260 mL) was added and reacted at 135℃for 6 hours. When the reaction was completed, 67g (83.4%) of product N-19 was obtained by the isolation method using P-1.
3.S-32 Synthesis example
S-32a(10g,0.04mol)、S-32b(15.6g,0.04mol)、Pd2(dba)3(1.1g,0.001mol)、NaOt-Bu(11.7g,0.12mol)、P(t-Bu)3(1.0g,0.002mol)、 Toluene (80 mL) was added and reacted at 135℃for 6 hours. When the reaction was completed, 18g (80.8%) of the product S-32 was obtained by the isolation method using P-1.
Synthesis example of S-74
S-74a(15g,0.06mol)、S-74b(20.9g,0.06mol)、Pd2(dba)3(1.6g,0.002mol)、NaOt-Bu(16.9g,0.18mol)、P(t-Bu)3(1.4g,0.004mol)、 Toluene (120 mL) was added and reacted at 135℃for 6 hours. When the reaction was completed, 27g (86.4%) of product S-74 was obtained by the isolation method using P-1.
5.S-104 Synthesis example
S-104a(30g,0.13mol)、S-104b(48.2.9g,0.13mol)、Pd2(dba)3(3.5g,0.004mol)、NaOt-Bu(36.4g,0.38mol)、P(t-Bu)3(3.1g,0.008mol)、 Toluene (250 mL) was added and reacted at 135℃for 6 hours. When the reaction was completed, 60g (81.5%) of product S-104 was obtained by the isolation method using P-1.
Meanwhile, FD-MS values of the inventive compounds N-1 to N-96 and the inventive compounds S-1 to S-108 prepared according to the above synthesis examples are shown in tables 4 and 5.
TABLE 4
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TABLE 5
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[ Element data ]
Example 1 Red organic light-emitting device (phosphorescent host)
The organic electroluminescent device is manufactured according to a conventional method using a compound obtained by synthesis as a light-emitting host material of a light-emitting layer. First, an N1- (naphthalen-2-yl) -N4, N4-bis (4- (naphthalen-2-yl (phenyl) amino) phenyl) -N1-phenylbenzene-1, 4-diamine (hereinafter, 2-TNATA) film was vacuum deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 60nm, and then 4, 4-bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl (hereinafter, NPB) as a hole transport compound was vacuum deposited on the hole injection layer to a thickness of 50nm to form a hole transport layer. Tris (4- (9H-carbazol-9-yl) phenyl) amine (hereinafter, TCTA) as a material of the light-emitting auxiliary layer was vacuum deposited on the hole transport layer to a thickness of 10nm to form the light-emitting auxiliary layer. After forming the light-emitting auxiliary layer, on the light-emitting auxiliary layer, the compound P-1 of the present invention represented by formula (1) and the compound N-12 of the present invention represented by formula (2) were used as a host in a weight ratio (5:5), and the light-emitting layer was deposited to a thickness of 30nm by doping (piq) 2 Ir (acac) as a dopant material in a weight ratio of 95:5. Then, (1, 1' -biphenyl) -4-bonded) bis (2-methyl-8-quinolinolato) aluminum (hereinafter, BAlq) was vacuum deposited to a thickness of 10nm as a hole blocking layer, and bis (10-hydroxybenzo [ h ] quinoline) beryllium (hereinafter, beBq 2) was deposited to a thickness of 20nm as an electron transport layer. Thereafter, liF as an alkali metal halide was deposited to a thickness of 0.2nm as an electron injection layer, and then Al was deposited to a thickness of 150nm and used as a cathode, thereby manufacturing an organic electroluminescent device.
Examples 2 to 29
An organic electroluminescent device was manufactured in the same manner as in example 1 by using the compound of the present invention shown in table 6 instead of the compound P-1 and the compound N-12 of the present invention as host materials of the light-emitting layer of example 1.
Comparative examples 1 to 2
An organic electroluminescent device was manufactured in the same manner as in example 1, but using comparative compound a or comparative compound B instead of the compound P-1 of the present invention as a host material for a light-emitting layer.
By applying a forward bias DC voltage to the organic electroluminescent devices manufactured by examples 1 to 29, comparative examples 1 and 2, electroluminescent (EL) characteristics were measured from PR-650 of Photoresearch, and T95 service life was measured at 2500cd/m 2 standard luminance using a service life measuring device manufactured by MCSCIENCE, and the measurement results are shown in table 6.
TABLE 6
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As can be seen from table 6, when the compound of the present invention is used as a host material of the light emitting layer, it can be seen that the efficiency is significantly improved as compared with the case of using the comparative compound a or the comparative compound B.
As can be seen from the above, when a plurality of compounds are mixed to form a body of the light emitting layer, characteristics are different according to types of the first compound and the second compound, and when the same compound is applied to the second compound, it can be seen that the characteristic difference is remarkably exhibited according to the type of the first compound. Similarly, according to this type, the second compound exhibits differences in driving voltage, efficiency, and service life.
Comparing compound a with the compounds of the present invention, as can be seen in table 6, it can be confirmed that the compounds of the present invention improve the overall efficiency and service life of the element.
Table 7 shows calculated dipole moments of comparative compounds A and P-2 according to the present invention.
TABLE 7
| Comparative Compound A | P-2 | |
| Dipole moment | 5.5878 | 0.4600 |
Comparison compound a was compared to the compound of the present invention, which had a core in which the cyano group was further substituted with a substituent of-phenyl-naphthyl-phenyl. However, the compounds of the present invention have a core that is not further substituted with a cyano group, and additionally have a substituent of the-phenyl-naphthyl structure as a substituent of the triazine. Due to this structure, the physical properties of the compounds were changed, and in particular, as shown in table 7, there was a large difference in dipole moment in the case of comparing the compounds a and P-2. In other words, since the cyano group has high electronegativity, it is judged to have a high dipole moment.
Due to this high dipole moment, charges in the molecule are biased, and the biased charges may impede the flow of charges. Thus, it appears that a load is generated in charge transfer, and the driving voltage of the element increases rapidly, which greatly affects the efficiency and the service life of the element.
Table 8 shows data measured by DFT method (B3 LYP/6-31g (D)) using Gaussian procedure comparing Compound A and Compound P-1 of the invention
TABLE 8
| Comparative Compound A | P-2 | |
| HOMO(eV) | -5.866 | -5.448 |
| LUMO(eV) | -1.951 | -1.828 |
| Eg(eV) | 3.914 | 3.620 |
| T1(eV) | 2.520 | 2.536 |
| S1(eV) | 3.460 | 3.187 |
As can be seen in table 8, comparing compound a with compound P-2 of the present invention, it can be seen that T1 is similar, but the band gap is reduced, and in particular S1 is reduced. For this reason, the wavelength of energy emitted from the host increases, and the energy is better transferred to the red dopant. In other words, the low S1 of the compound P-2 of the present invention promotes transfer of Foster energy to the dopant, which appears to affect the overall performance improvement of the element.
Further, when comparing compound B with the compound of the present invention, it can be seen that the compound of the present invention improves the overall driving voltage and efficiency of the element, as shown in table 6. The comparative compound B has a structure in which-phenyl-naphthyl is substituted with a substituent of triazine, and the compound of the present invention has a structure of-phenyl-naphthyl-phenyl. That is, it appears that the efficiency of the element is affected depending on the type of substituent.
The calculated recombination energy values for comparative compounds B and P-2 are described in Table 9.
The RE values shown in table 9 mean values calculated by RE elec.
TABLE 9
| Compounds of formula (I) | Recombinant Energy (RE) |
| Comparative Compound B | 0.299 |
| P-2 | 0.231 |
Referring to Table 9, RE values vary depending on the substituents of the triazine, the compound P-2 of the present invention has a lower RE value than the comparative compound B. That is, when having a lower RE value, this means high mobility and fast EOD, and the compound of the present invention having a fast EOD value appears to have a fast driving voltage, high efficiency, and long service life as a whole. Particularly when the light emitting layer is composed of a plurality of mixtures, the driving voltage, efficiency, and lifetime are determined according to the easiness of hole and electron injection into the dopant, and when the hole and electron ratio (charge balance) is properly maintained, the efficiency increases.
In particular, as can be seen from examples 14 to 29, as a plurality of host compounds, characteristics are different depending on the types of the first compound and the second compound, and finally, the performance of the judgment element is determined depending on the injection characteristics of the hole and electron injection dopants. In the present invention, it can be seen that the overall driving voltage lowering effect, efficiency and life increasing effect are brought about by the relationship between the RE value and mobility. Furthermore, the combination of specific substituents that replace triazines has a positive effect on overall mobility and acts as a hole-electron ratio (e.g., energy balance, stability, etc.), showing overall improved results. That is, even within the same skeleton, the RE value is determined according to the type of substituent and the substitution position, and it can be seen that the characteristics are very different. Furthermore, in the case of the compound of the present invention, it can be seen that the value of CIEx slightly increases, which suggests that the compound of the present invention as a host may affect the color of the element. That is, as in the present invention, when phenanthrooxazole structure and phenanthrene structure are simultaneously substituted with a substituent of triazine at a specific position, the effect is considered to be maximized as a synergistic effect.
Although exemplary embodiments of the present invention have been described for illustrative purposes, those skilled in the art will appreciate that various modifications, additions and substitutions are possible, without departing from the scope and spirit of the invention as disclosed in the accompanying claims. Accordingly, the embodiments disclosed in the present invention are intended to exemplify the scope of the technical idea of the present invention, and the scope of the present invention is not limited by the embodiments. The scope of the present invention should be construed based on the appended claims, and should be construed as including all technical ideas within the scope equivalent to the claims.
Claims (12)
1. A compound represented by formula (1):
(1)
Wherein:
A is a substituent represented by the formula (A-1) or the formula (A-2);
R 1、R2、R3、R4 and R 5, equal to or different from each other, are hydrogen or deuterium;
a and b are each independently an integer from 0 to 4, c is an integer from 0 to 7, d is an integer from 0 to 6, and e is an integer from 0 to 5;
L a is a direct bond or a C 6-C60 arylene group;
ar a is a C 6-C60 aryl group;
Wherein the aryl or arylene group may be substituted with one or more substituents selected from deuterium; halogen; a silane group; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; a C 1-C20 alkylthio group; a C 1-C20 alkoxy group; a C 1-C20 alkyl group; a C 2-C20 alkenyl group; a C 2-C20 alkynyl group; a C 6-C20 aryl group; a C 6-C20 aryl group substituted with deuterium; fluorenyl groups; a C 2-C20 heterocyclic group; a C 3-C20 cycloalkyl group; a C 7-C20 arylalkyl group; and a C 8-C20 arylalkenyl group; and the substituents may bond to each other to form a saturated or unsaturated ring, wherein the term "ring" means a C 3-C60 aliphatic ring or a C 6-C60 aromatic ring or a C 2-C60 heterocyclic group or a fused ring formed by a combination thereof.
2. The compound according to claim 1, wherein Ar a is represented by any one of formula (a-1) to formula (a-3):
Wherein:
* The bonding position is indicated by the number of the bonding sites,
R 6、R7 and R 8 are each the same or different and are each independently hydrogen; deuterium; or a C 6-C20 aryl group;
f is an integer of 0 to 5, g is an integer of 0 to 7, and h is an integer of 0 to 9.
3. The compound according to claim 1, wherein L a is represented by any one of formula (L-1) to formula (L-3):
Wherein:
* The bonding position is indicated by the number of the bonding sites,
R 9、R10、R11 and R 12 are each the same or different and are each independently hydrogen; deuterium; or a C 6-C20 aryl group,
I. k and l are each independently integers from 0 to 4, and j is an integer from 0 to 6.
4. The compound according to claim 1, wherein the compound represented by formula 1 is represented by any one of P-1 to P-98:
5. An organic electronic element comprising: a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, wherein the light emitting layer is a phosphorescent light emitting layer and includes a first host compound represented by formula 1 and a second host compound represented by formula 2 or formula 3 described in claim 1:
Wherein:
L 4、L5、L6 and L 7 are each independently selected from single bonds; a C 6-C60 arylene group; fluorenylene groups; a fused ring group of a C 3-C60 aliphatic ring and a C 6-C60 aromatic ring; a C 2-C60 heterocyclic group;
Ar 3、Ar4 and Ar 5 are each independently selected from C 6-C60 aryl groups; fluorenyl groups; a C 2-C60 heterocyclic group comprising at least one heteroatom of O, N, S, si or P; and fused ring groups of C 3-C60 aliphatic and C 6-C60 aromatic rings;
Ar 6 is each independently selected from the group consisting of C 6-C60 aryl groups; fluorenyl groups; a C 2-C60 heterocyclic group comprising at least one heteroatom of O, N, S, si or P; a fused ring group of a C 3-C60 aliphatic ring and a C 6-C60 aromatic ring; -L' -N (R b)(Rc),
L' is selected from single bonds; a C 6-C60 arylene group; a C 2-C60 heterocyclic group comprising at least one heteroatom of O, N, S, si or P;
R b and R c are each independently selected from C 6-C60 aryl groups; fluorenyl groups; a fused ring group of a C 3-C60 aliphatic ring and a C 6-C60 aromatic ring; a C 2-C60 heterocyclic group comprising at least one heteroatom of O, N, S, si or P; a C 1-C50 alkyl group; a C 2-C20 alkenyl group; a C 2-C20 alkynyl group; a C 1-C30 alkoxy group; a C 6-C30 aryloxy group;
z is O, S, CR 'R' or NRa,
B is a C 6-C20 aryl group,
R 'and R' are each independently selected from C 6-C60 aryl groups; fluorenyl groups; a C 2-C60 heterocyclic group comprising at least one heteroatom of O, N, S, si or P; a fused ring group of a C 3-C60 aliphatic ring and a C 6-C60 aromatic ring; a C 1-C50 alkyl group; a C 2-C20 alkenyl group; a C 2-C20 alkynyl group; a C 1-C30 alkoxy group; a C 6-C30 aryloxy group; or may be bonded to each other to form a ring,
R 31 and R 32 are each independently the same or different from each other and are each independently selected from hydrogen; deuterium; halogen; a cyano group; a nitro group; a C 6-C60 aryl group; fluorenyl groups; a C 2-C60 heterocyclic group comprising at least one heteroatom of O, N, S, si or P; a fused ring group of a C 3-C60 aliphatic ring and a C 6-C60 aromatic ring; a C 1-C60 alkyl group; a C 2-C60 alkenyl group; a C 2-C60 alkynyl group; a C 1-C60 alkoxy group; a C 6-C60 aryloxy group; or a plurality of adjacent R 31 or a plurality of R 32 may be bonded to each other to form a ring,
N and o are each independently integers from 0 to 4,
Ra is a C 6-C60 aryl group; or a C 2-C60 heterocyclic group comprising at least one heteroatom of O, N, S, si and P,
Wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, and aryloxy group may be substituted with one or more substituents selected from deuterium; halogen; a silane group; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; a C 1-C20 alkylthio group; a C 1-C20 alkoxy group; a C 1-C20 alkyl group; a C 2-C20 alkenyl group; a C 2-C20 alkynyl group; a C 6-C20 aryl group; a C 6-C20 aryl group substituted with deuterium; fluorenyl groups; a C 2-C20 heterocyclic group; a C 3-C20 cycloalkyl group; a C 7-C20 arylalkyl group; a C 8-C20 arylalkenyl group; and the substituents may bond to each other to form a saturated or unsaturated ring, wherein the term "ring" means a C 3-C60 aliphatic ring or a C 6-C60 aromatic ring or a C 2-C60 heterocyclic group or a fused ring formed by a combination thereof.
6. The organic electronic element according to claim 5, wherein the compound represented by formula 2 is any one of compounds N-1 to N-96:
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7. The organic electronic element according to claim 5, wherein the compound represented by formula 3 is any one of compounds S-1 to S-108:
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8. The organic electronic element of claim 5 wherein the organic electronic element further comprises a light efficiency enhancing layer formed on at least one surface of the first and second electrodes, the surface being opposite the organic material layer.
9. The organic electronic element according to claim 5, wherein the organic material layer includes 2 or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first electrode.
10. The organic electronic element according to claim 9, wherein the organic material layer further comprises a charge generation layer formed between the 2 or more stacks.
11. An electronic device comprising a display device comprising the organic electronic element of claim 5; and a control unit for driving the display device.
12. The electronic device of claim 11, wherein the organic electronic element is at least one of an OLED, an organic solar cell, an Organic Photoconductor (OPC), an organic transistor (organic TFT), and an element for monochromatic or white illumination.
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| US18/057,570 | 2022-11-21 |
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