KR20190080063A - Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof - Google Patents
Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof Download PDFInfo
- Publication number
- KR20190080063A KR20190080063A KR1020170182251A KR20170182251A KR20190080063A KR 20190080063 A KR20190080063 A KR 20190080063A KR 1020170182251 A KR1020170182251 A KR 1020170182251A KR 20170182251 A KR20170182251 A KR 20170182251A KR 20190080063 A KR20190080063 A KR 20190080063A
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- South Korea
- Prior art keywords
- group
- ring
- layer
- formula
- heterocyclic
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 57
- 239000012044 organic layer Substances 0.000 claims abstract description 30
- 239000000126 substance Substances 0.000 claims abstract 4
- 239000010410 layer Substances 0.000 claims description 90
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 125000000623 heterocyclic group Chemical group 0.000 claims description 43
- 125000005842 heteroatom Chemical group 0.000 claims description 32
- 229910052717 sulfur Inorganic materials 0.000 claims description 32
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 229910052710 silicon Inorganic materials 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 125000001931 aliphatic group Chemical group 0.000 claims description 25
- 229910052698 phosphorus Inorganic materials 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 239000011368 organic material Substances 0.000 claims description 20
- 125000004122 cyclic group Chemical group 0.000 claims description 17
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 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 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 125000005567 fluorenylene group Chemical group 0.000 claims description 6
- -1 aryl alkene Chemical class 0.000 claims description 5
- 239000002096 quantum dot Substances 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 238000003618 dip coating Methods 0.000 claims description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
- 238000005286 illumination Methods 0.000 claims description 2
- 230000008676 import Effects 0.000 claims description 2
- 238000007641 inkjet printing Methods 0.000 claims description 2
- 238000007639 printing Methods 0.000 claims description 2
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 2
- 238000004528 spin coating Methods 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 37
- 239000000463 material Substances 0.000 description 35
- 230000015572 biosynthetic process Effects 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- 239000000741 silica gel Substances 0.000 description 26
- 229910002027 silica gel Inorganic materials 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000012141 concentrate Substances 0.000 description 22
- 239000000203 mixture Substances 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 18
- 0 C*c(cccc1*C)c1NC Chemical compound C*c(cccc1*C)c1NC 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 5
- 238000005401 electroluminescence Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 238000000434 field desorption mass spectrometry Methods 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 3
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
- 101150003085 Pdcl gene Proteins 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical compound C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 description 2
- QTPLEVOKSWEYAC-UHFFFAOYSA-N 1,2-diphenyl-9h-fluorene Chemical compound C=1C=CC=CC=1C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC=CC=C1 QTPLEVOKSWEYAC-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- 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 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- PQIUGRLKNKSKTC-UHFFFAOYSA-N benzo[h]quinazoline Chemical compound N1=CN=C2C3=CC=CC=C3C=CC2=C1 PQIUGRLKNKSKTC-UHFFFAOYSA-N 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 2
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 2
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 125000005580 triphenylene group Chemical group 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- NRESDXFFSNBDGP-UHFFFAOYSA-N (4-bromophenyl)hydrazine Chemical compound NNC1=CC=C(Br)C=C1 NRESDXFFSNBDGP-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 1
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 1
- HPJCIBVGJBEJPU-UHFFFAOYSA-N 1-fluoro-9h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1C(F)=CC=C2 HPJCIBVGJBEJPU-UHFFFAOYSA-N 0.000 description 1
- UZUCMBNQFISSPB-UHFFFAOYSA-N 1-fluoronaphthalen-2-ol Chemical compound C1=CC=CC2=C(F)C(O)=CC=C21 UZUCMBNQFISSPB-UHFFFAOYSA-N 0.000 description 1
- FBTOLQFRGURPJH-UHFFFAOYSA-N 1-phenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 FBTOLQFRGURPJH-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- QZOCQWGVJOPBDK-UHFFFAOYSA-N 2-iodobenzenethiol Chemical compound SC1=CC=CC=C1I QZOCQWGVJOPBDK-UHFFFAOYSA-N 0.000 description 1
- KQDJTBPASNJQFQ-UHFFFAOYSA-N 2-iodophenol Chemical compound OC1=CC=CC=C1I KQDJTBPASNJQFQ-UHFFFAOYSA-N 0.000 description 1
- AZFABGHLDGJASW-UHFFFAOYSA-N 3-bromodibenzofuran Chemical compound C1=CC=C2C3=CC=C(Br)C=C3OC2=C1 AZFABGHLDGJASW-UHFFFAOYSA-N 0.000 description 1
- QLILRKBRWXALIE-UHFFFAOYSA-N 3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1 QLILRKBRWXALIE-UHFFFAOYSA-N 0.000 description 1
- WOFZZXBUBNFNOC-UHFFFAOYSA-N 4-(4-anilinophenyl)-2,3-dinaphthalen-1-yl-n-phenylaniline Chemical compound C=1C=C(C=2C(=C(C(NC=3C=CC=CC=3)=CC=2)C=2C3=CC=CC=C3C=CC=2)C=2C3=CC=CC=C3C=CC=2)C=CC=1NC1=CC=CC=C1 WOFZZXBUBNFNOC-UHFFFAOYSA-N 0.000 description 1
- NJBMMMJOXRZENQ-UHFFFAOYSA-N 6H-pyrrolo[2,3-f]quinoline Chemical compound c1cc2ccc3[nH]cccc3c2n1 NJBMMMJOXRZENQ-UHFFFAOYSA-N 0.000 description 1
- LKCRSRNEAPLOOP-UHFFFAOYSA-N C1(=CC=CC=C1)C1=NC(=CC2=CC=CC=C12)[Ir+2] Chemical compound C1(=CC=CC=C1)C1=NC(=CC2=CC=CC=C12)[Ir+2] LKCRSRNEAPLOOP-UHFFFAOYSA-N 0.000 description 1
- XHOCITIFDXZHAT-UHFFFAOYSA-N C1=CC2=C(C=CC(=C2O)I)C=C1Br Chemical compound C1=CC2=C(C=CC(=C2O)I)C=C1Br XHOCITIFDXZHAT-UHFFFAOYSA-N 0.000 description 1
- NGYSLRRBPCPOFG-UHFFFAOYSA-N C1=CC=C2C(=C1)C3=C(N2)C(=C4C=CC(=CC4=C3)Br)F Chemical compound C1=CC=C2C(=C1)C3=C(N2)C(=C4C=CC(=CC4=C3)Br)F NGYSLRRBPCPOFG-UHFFFAOYSA-N 0.000 description 1
- RXZNMYYAPCPQHI-UHFFFAOYSA-N CC(C)(c(cccc1)c1-c1c2)c1c1Oc(c(cccc3)c3cc3)c3-[n]3c1c2c1c3cc(c2ccccc2[s]2)c2c1 Chemical compound CC(C)(c(cccc1)c1-c1c2)c1c1Oc(c(cccc3)c3cc3)c3-[n]3c1c2c1c3cc(c2ccccc2[s]2)c2c1 RXZNMYYAPCPQHI-UHFFFAOYSA-N 0.000 description 1
- KTKQWYCUDKUGOR-UHFFFAOYSA-N CC(C)(c(cccc1)c1-c1c2)c1c1Oc3c(cccc4)c4ccc3-[n]3c1c2c1c3cccc1 Chemical compound CC(C)(c(cccc1)c1-c1c2)c1c1Oc3c(cccc4)c4ccc3-[n]3c1c2c1c3cccc1 KTKQWYCUDKUGOR-UHFFFAOYSA-N 0.000 description 1
- YTWSEOAIOWDIIW-UHFFFAOYSA-N CC(C)(c1ccccc1-1)c2c-1c(c1c3cc4[s]c5ccccc5c4c1)c1[n]3-c(c(cccc3)c3cc3)c3Sc1c2 Chemical compound CC(C)(c1ccccc1-1)c2c-1c(c1c3cc4[s]c5ccccc5c4c1)c1[n]3-c(c(cccc3)c3cc3)c3Sc1c2 YTWSEOAIOWDIIW-UHFFFAOYSA-N 0.000 description 1
- PFFCMNJSSGORRO-UHFFFAOYSA-N CC(C)(c1ccccc1-c1c2)c1cc1c2[n]2-c(cc(cccc3)c3c3)c3Sc3cc([s]c4ccccc44)c4c1c23 Chemical compound CC(C)(c1ccccc1-c1c2)c1cc1c2[n]2-c(cc(cccc3)c3c3)c3Sc3cc([s]c4ccccc44)c4c1c23 PFFCMNJSSGORRO-UHFFFAOYSA-N 0.000 description 1
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- HEGGDANXMNZJDD-UHFFFAOYSA-N CC(C)(c1ccccc1-c1ccc23)c1c2c1c(cccc2)c2cc2c1[n]3-c(ccc1c3N(c4ccccc4)c4ccccc4S1)c3S2 Chemical compound CC(C)(c1ccccc1-c1ccc23)c1c2c1c(cccc2)c2cc2c1[n]3-c(ccc1c3N(c4ccccc4)c4ccccc4S1)c3S2 HEGGDANXMNZJDD-UHFFFAOYSA-N 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/14—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H01L51/0003—
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- H01L51/0069—
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- H01L51/0071—
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- H01L51/5012—
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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Abstract
Description
본 발명은 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치에 관한 것이다.TECHNICAL FIELD The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device therefor.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛 에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기전기소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물 층은 유기전기소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 등으로 이루어질 수 있다.In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic electric device using an organic light emitting phenomenon generally has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic electronic device, the organic material layer is often formed of a multilayer structure composed of different materials, and may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
유기전기소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하수송 재료, 예컨대 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다. 그리고, 상기 발광 재료는 분자량에 따라 고분자형과 저분자형으로 분류될 수 있고, 발광 메커니즘에 따라 전자의 일중항 여기상태로부터 유래되는 형광 재료와 전자의 삼중항 여기상태로부터 유래되는 인광 재료로 분류될 수 있다. 또한, 발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료로 구분될 수 있다.A material used as an organic material layer in an organic electric device 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 transporting material, and an electron injecting material depending on functions. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight, and may be classified into a phosphorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons . Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.
한편, 발광 재료로서 하나의 물질만 사용하는 경우 분자간 상호 작용에 의하여 최대 발광 파장이 장파장으로 이동하고 색순도가 떨어지거나 발광 감쇄 효과로 소자의 효율이 감소되는 문제가 발생하므로, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여 발광 재료로서 호스트/도판트계를 사용할 수 있다. 그 원리는 발광층을 형성하는 호스트보다 에너지 대역 간극이 작은 도판트를 발광층에 소량 혼합하면, 발광층에서 발생한 엑시톤이 도판트로 수송되어 효율이 높은 빛을 내는 것이다. 이때 호스트의 파장이 도판트의 파장대로 이동하므로, 이용하는 도판트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다.On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system may be used as a light emitting material in order to increase the light emitting efficiency through the light emitting layer. When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.
현재 휴대용 디스플레이 시장은 대면적 디스플레이로 그 크기가 증가하고 있는 추세이며, 이로 인해 기존 휴대용 디스플레이에서 요구되던 소비적력보다 더 큰 소비전력이 요구되고 있다. 따라서, 배터리라는 제한적인 전력 공급원을 가지고 있는 휴대용 디스플레이 입장에서는 소비전력이 매우 중요한 요소가 되었고, 효율과 수명 문제 또한 반드시 해결해야 하는 상황이다.Currently, the portable display market is growing in size as a large-area display, which requires more power than the power consumption required by existing portable displays. Therefore, power consumption becomes a very important factor for portable displays, which have a limited power source, such as a battery, and efficiency and lifetime issues must be solved.
효율과 수명, 구동전압 등은 서로 연관이 있으며, 효율이 증가되면 상대적으로 구동전압이 떨어지고, 구동전압이 떨어지면서 구동 시 발생하는 주울열(Joule heating)에 의한 유기물질의 결정화가 적어져 결과적으로 수명이 높아지는 경향을 나타낸다. 하지만 상기 유기물층을 단순히 개선한다고 하여 효율을 극대화시킬 수는 없다. 왜냐하면, 각 유기물층 간의 에너지 준위(energy level) 및 T1 값, 물질의 고유특성(이동도, 계면특성 등) 등이 최적의 조합을 이루었을 때 긴 수명과 높은 효율을 동시에 달성할 수 있기 때문이다.The efficiency, lifetime, and driving voltage are related to each other. As the efficiency increases, the driving voltage decreases. As the driving voltage decreases, the crystallization of the organic material due to Joule heating, which occurs during driving, And the lifetime tends to increase. However, simply improving the organic material layer can not maximize the efficiency. This is because, when the optimum combination of the energy level and the T 1 value and the intrinsic properties (mobility, interfacial characteristics, etc.) of the materials are achieved, long life and high efficiency can be achieved at the same time .
따라서 높은 열적 안정성을 가지며 발광층 내에서 효율적으로 전하 균형(charge balance)을 이룰 수 있는 발광 재료의 개발이 필요한 실정이다. 즉, 유기전기소자가 갖는 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨대 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지 안정하고 효율적인 유기전기소자용 유기물층 재료의 개발이 충분히 이루어지지 않은 상태이며, 그 중에서도 특히 발광층의 호스트 물질에 대한 개발이 절실히 요구되고 있다.Therefore, it is necessary to develop a light emitting material having high thermal stability and achieving a charge balance in the light emitting layer efficiently. That is, in order to sufficiently exhibit the excellent characteristics of the organic electronic device, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material and an electron injecting material is supported by a stable and efficient material However, development of a stable and efficient organic material layer for an organic electric device has not yet been sufficiently developed. Particularly, development of a host material for a light emitting layer is urgently required.
본 발명은 소자의 구동전압을 낮추고, 소자의 발광효율 및 수명을 향상시킬 수 있는 화합물, 이를 이용한 유기전기소자 및 그 전자장치를 제공하는 것을 목적으로 한다.Disclosure of the Invention An object of the present invention is to provide a compound capable of lowering the driving voltage of a device and improving the luminous efficiency and lifetime of the device, an organic electric device using the same, and an electronic device therefor.
일 측면에서, 본 발명은 하기 화학식으로 표시되는 화합물을 제공한다.In one aspect, the invention provides compounds represented by the formula:
다른 측면에서, 본 발명은 상기 화학식으로 표시되는 화합물을 이용한 유기전기소자 및 그 전자장치를 제공한다.In another aspect, the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device thereof.
본 발명의 실시예에 따른 화합물을 이용함으로써 소자의 구동전압을 낮출 수 있고, 소자의 발광효율 및 수명을 현저히 향상시킬 수 있다.By using the compound according to an embodiment of the present invention, the driving voltage of the device can be lowered, and the luminous efficiency and lifetime of the device can be remarkably improved.
도 1은 본 발명의 일실시예 따른 유기전기발광소자의 예시도이다. 1 is an exemplary view of an organic electroluminescent device according to an embodiment of the present invention.
본 명세서에서 각 기호 및 그 치환기의 예로 예시되는 아릴기, 아릴렌기, 헤테로고리기 등에 해당하는 '기 이름'은 '가수를 반영한 기의 이름'을 기재할 수도 있지만, '모체화합물 명칭'으로 기재할 수도 있다. 예컨대, 아릴기의 일종인 '페난트렌'의 경우, 1가의 '기'는 '페난트릴'로 2가의 기는 '페난트릴렌' 등과 같이 가수를 구분하여 기의 이름을 기재할 수도 있지만, 가수와 상관없이 모체 화합물 명칭인 '페난트렌'으로 기재할 수도 있다. 유사하게, 피리미딘의 경우에도, 가수와 상관없이 '피리미딘'으로 기재하거나, 1가인 경우에는 피리미딘일기, 2가의 경우에는 피리미딘일렌 등과 같이 해당 가수의 '기의 이름'으로 기재할 수도 있다. In the present specification, the 'group name' corresponding to the aryl group, the arylene group, the heterocyclic group and the like exemplified as the examples of the respective symbols and substituents thereof may be described as 'the name of the group reflecting the singer' You may. For example, in the case of phenanthrene, which is a kind of aryl group, a monovalent 'group' may be named 'phenanthryl' and a bivalent group may be named 'phenanthrylene' It may be described as "phenanthrene" which is the name of the parent compound. Similarly, in the case of pyrimidine, it may also be described as 'pyrimidine' irrespective of the valence number, or may be described as the 'name of the group' of the corresponding singer, such as pyrimidine di have.
본 발명에 사용된 용어 "플루오렌일기" 또는 "플루오렌일렌기"는 다른 설명이 없는 한 각각 하기 구조에서 R, R' 및 R"이 모두 수소인 1가 또는 2가 작용기를 의미하며, "치환된 플루오렌일기" 또는 "치환된 플루오렌일렌기"는 치환기 R, R', R" 중 적어도 하나가 수소 이외의 치환기인 것을 의미하며, R과 R'이 서로 결합되어 이들이 결합된 탄소와 함께 스파이로 화합물을 형성한 경우를 포함한다.The term "fluorenyl group" or "fluorenylene group" used in the present invention means a monovalent or divalent functional group in which R, R 'and R & Substituted fluorenyl group "or" substituted fluorenylene group "means that at least one of the substituents R, R 'and R" is a substituent other than hydrogen, and R and R' Together with a spy compound.
본 발명에서 사용된 용어 "스파이로 화합물"은 '스파이로 연결(spiro union)'을 가지며, 스파이로 연결은 2개의 고리가 오로지 1개의 원자를 공유함으로써 이루어지는 연결을 의미한다. 이때, 두 고리에 공유된 원자를 '스파이로 원자'라 하며, 한 화합물에 들어 있는 스파이로 원자의 수에 따라 이들을 각각 '모노스파이로-', '다이스파이로-', '트라이스파이로-' 화합물이라 한다. The term "spiro compound" used in the present invention has a 'spiro union', and a spiro connection means a connection in which two rings share only one atom. At this time, atoms shared in two rings are called 'spyro atoms', and they are referred to as 'monospyros,' 'di spyroses,' and 'tri-spyros', depending on the number of spyro atoms contained in a compound. 'Compounds.
본 발명에 사용된 용어 "헤테로고리기"는, 고리를 형성하는 탄소 대신 N, O, S, P 또는 Si 등과 같은 헤테로원자가 포함된 고리를 의미하며, "헤테로아릴기" 또는 "헤테로아릴렌기"와 같은 방향족 고리뿐만 아니라 비방향족 고리도 포함하며, 고리를 형성하는 탄소 대신 하기 화합물과 같이 SO2, P=O 등과 같은 헤테로원자단을 포함하는 화합물도 포함될 수 있다.The term "heterocyclic group" used in the present invention means a ring containing a hetero atom such as N, O, S, P or Si instead of carbon forming a ring, and the term "heteroaryl group" or "heteroarylene group" As well as non-aromatic rings, and compounds containing hetero atoms such as SO 2 , P═O, etc., such as the following compounds, instead of ring-forming carbon, may also be included.
또한, 명시적인 설명이 없는 한, 본 발명에서 사용되는 화학식은 하기 화학식의 지수 정의에 의한 치환기 정의와 동일하게 적용된다.Unless otherwise expressly stated, the formula used in the present invention is applied in the same manner as the definition of the substituent by the definition of the index of the following formula.
여기서, a가 0의 정수인 경우 치환기 R1은 부존재하며, a가 1의 정수인 경우 하나의 치환기 R1은 벤젠 고리를 형성하는 탄소 중 어느 하나의 탄소에 결합하며, a가 2 또는 3의 정수인 경우 각각 아래와 같이 결합하며 이때 R1은 서로 동일하거나 다를 수 있으며, a가 4 내지 6의 정수인 경우 이와 유사한 방식으로 벤젠 고리의 탄소에 결합하며, 한편 벤젠 고리를 형성하는 탄소에 결합된 수소의 표시는 생략한다.When a is an integer of 0, substituent R 1 is absent. When a is an integer of 1, one substituent R 1 is bonded to any one of carbon atoms forming a benzene ring, and when a is an integer of 2 or 3 each coupled as shown below, and wherein R 1 may be the same or different from each other, a is and bonded to the carbon of the benzene ring in the similar manner in this case from 4 to 6 integer, while the display of the hydrogen bonded to the carbon to form a benzene ring It is omitted.
이하, 본 발명의 화합물이 포함된 유기전기소자의 적층구조에 대하여 도 1을 참조하여 설명한다.Hereinafter, a lamination structure of an organic electronic device including a compound of the present invention will be described with reference to FIG.
도 1은 본 발명에 일 실시예에 따른 유기전기소자의 적층 구조를 예시한 도면이다.1 is a view illustrating a stacked structure of organic electroluminescent devices according to an embodiment of the present invention.
도 1을 참조하면, 본 발명에 따른 유기전기소자(100)는 기판(110) 상에 형성된 제 1전극(120), 제 2전극(180) 및 제 1전극(110)과 제 2전극(180) 사이에 본 발명에 따른 화합물을 포함하는 유기물층을 구비한다. 이때, 제 1전극(120)은 애노드(양극)이고, 제 2전극(180)은 캐소드(음극)일 수 있으며, 인버트형의 경우에는 제 1전극이 캐소드이고 제 2전극이 애노드일 수 있다.1, an organic
유기물층은 제 1전극(120) 상에 순차적으로 정공주입층(130), 정공수송층(140), 발광층(150), 전자수송층(160) 및 전자주입층(170)을 포함할 수 있다. 이때, 이들 층 중 적어도 하나가 생략되거나, 정공저지층, 전자저지층, 발광보조층(151), 버퍼층(141) 등이 더 포함될 수도 있으며, 전자수송층(160) 등이 정공저지층의 역할을 할 수도 있을 것이다.The organic material layer may include a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, an electron transporting layer 160, and an electron injecting layer 170 sequentially on the first electrode 120. At this time, at least one of these layers may be omitted, or a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151 and a buffer layer 141 may be further included, and the electron transporting layer 160 may serve as a hole blocking layer You can do it.
또한, 미도시하였지만, 본 발명에 따른 유기전기소자는 제 1전극과 제 2전극 중 적어도 일면 중 상기 유기물층과 반대되는 일면에 형성된 보호층 또는 광효율 개선층(Capping layer)을 더 포함할 수 있다.Also, although not shown, the organic electroluminescent device according to the present invention may further include a protective layer or a light-efficiency-improving layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer.
상기 유기물층에 적용되는 본 발명에 따른 화합물은 정공주입층(130), 정공수송층(140), 전자수송층(160), 전자주입층(170), 발광층(150), 광효율 개선층, 발광보조층 등의 재료로 사용될 수 있을 것이다. 일례로, 본 발명의 화합물은 발광층(150)의 재료, 바람직하게는 발광층의 호스트 재료로 사용될 수 있다.The compound according to the present invention applied to the organic material layer includes a hole injecting layer 130, a hole transporting layer 140, an electron transporting layer 160, an electron injecting layer 170, a light emitting layer 150, a light efficiency improving layer, And the like. In one example, the compound of the present invention can be used as a material of the light emitting layer 150, preferably as a host material of the light emitting layer.
본 발명의 일 실시예에 따른 유기전기발광소자는 다양한 증착법(deposition)을 이용하여 제조될 수 있을 것이다. PVD나 CVD 등의 증착 방법을 사용하여 제조될 수 있는데, 예컨대, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극(120)을 형성하고, 그 위에 정공주입층(130), 정공수송층(140), 발광층(150), 전자수송층(160) 및 전자주입층(170)을 포함하는 유기물층을 형성한 후, 그 위에 음극(180)으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 또한, 정공수송층(140)과 발광층(150) 사이에 발광보조층(151)이 추가로 형성될 수 있다.An organic electroluminescent device according to an embodiment of the present invention may be manufactured using various deposition methods. For example, a metal or a metal oxide having conductivity or an alloy thereof may be deposited on a substrate to form a cathode 120, and a hole injection layer 130 may be formed thereon. A hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170, and then depositing a material that can be used as a cathode 180 on the organic layer. have. Further, a light emitting auxiliary layer 151 may be additionally formed between the hole transport layer 140 and the light emitting layer 150.
또한, 유기물층은 다양한 고분자 소재를 사용하여 용액 공정 또는 솔벤트 프로세스(solvent process), 예컨대 스핀코팅 공정, 노즐 프린팅 공정, 잉크젯 프린팅 공정, 슬롯코팅 공정, 딥코팅 공정, 롤투롤 공정, 닥터 블레이딩 공정, 스크린 프린팅 공정, 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조될 수 있다. 본 발명에 따른 유기물층은 다양한 방법으로 형성될 수 있으므로, 그 형성방법에 의해 본 발명의 권리범위가 제한되는 것은 아니다.In addition, the organic material layer may be formed by using various polymer materials in a solution process or a solvent process such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll- A screen printing process, a thermal transfer process, or the like. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the forming method.
본 발명에 따른 유기전기소자는 유기전기발광소자(OLED), 유기태양전지, 유기감광체(OPC), 유기트랜지스터(유기 TFT), 단색 또는 백색 조명용 소자, 퀀텀닷 디스플레이용 소자 중 하나일 수 있다.The organic electroluminescent device according to the present invention can be one of an organic electroluminescent (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device, or a device for a quantum dot display.
본 발명의 다른 실시예는 상술한 본 발명의 유기전기소자를 포함하는 디스플레이장치와, 이 디스플레이장치를 제어하는 제어부를 포함하는 전자장치를 포함할 수 있다. 이때, 전자장치는 현재 또는 장래의 유무선 통신단말일 수 있으며, 휴대폰 등의 이동 통신 단말기, PDA, 전자사전, PMP, 리모콘, 네비게이션, 게임기, 각종 TV, 각종 컴퓨터 등 모든 전자장치를 포함하며, 상기 디스플레이장치는 유기전기발광 디스플레이, 퀀텀닷 디스플레이 등을 포함할 수 있다.Another embodiment of the present invention can include an electronic device including a display device including the above-described organic electronic device of the present invention and a control unit for controlling the display device. At this time, the electronic device may be a current or future wired or wireless communication terminal and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, The display device may include an organic electroluminescent display, a quantum dot display, and the like.
이하, 본 발명의 일 측면에 따른 화합물에 대하여 설명한다.Hereinafter, the compound according to one aspect of the present invention will be described.
본 발명의 일측면에 따른 화합물은 하기 화학식 1로 표시된다.A compound according to one aspect of the present invention is represented by the following formula (1).
<화학식 1>≪ Formula 1 >
상기 화학식 1에서, 각 기호는 아래와 같이 정의될 수 있다.In the above formula (1), each symbol may be defined as follows.
A환, B환 및 C환은 서로 독립적으로 C6~C24의 방향족고리; 또는 O, N, S, Si, P 중 적어도 하나의 헤테로원자를 포함하는 C2~C20의 헤테로고리이다. 단, A환, B환 및 C환 중 적어도 하나는 C10~C24의 방향족고리이거나, 또는 O, N, S, Si, P 중 적어도 하나의 헤테로원자를 포함하는 C8~C20의 헤테로고리인 것이 바람직하다.A ring, B ring and C ring are independently of each other a C 6 -C 24 aromatic ring; Or O, a heterocyclic group of N, S, Si, C 2 ~ containing at least one hetero atom in the P C 20. Provided that at least one of A ring, B ring and C ring is an aromatic ring of C 10 to C 24 or a C 8 to C 20 hetero ring containing at least one hetero atom of O, N, S, Si and P Ring.
A환, B환 및 C환이 방향족고리인 경우, 바람직하게는 C6~C20의 방향족고리, 더욱 바람직하게는 C6~C10의 방향족고리, 예컨대 벤젠, 나프탈렌 등일 수 있다. A환, B환 및 C환이 헤테로고리인 경우, 바람직하게는 C5~C24의 헤테로고리, 더욱 바람직하게는 C5~C9의 헤테로고리, 예컨대 퀴놀린, 퀴나졸린 등일 수 있다.When the A ring, the B ring and the C ring are aromatic rings, it is preferably a C 6 to C 20 aromatic ring, more preferably a C 6 to C 10 aromatic ring, such as benzene, naphthalene, and the like. When A ring, B ring and C ring are heterocycles, it is preferably a C 5 to C 24 heterocycle, more preferably a C 5 to C 9 heterocycle, such as quinoline, quinazoline, and the like.
A환, B환 및 C환 중 적어도 하나에 하기 화학식 1-1이 결합된다.The following Formula 1-1 is bonded to at least one of the A ring, the B ring, and the C ring.
<화학식 1-1>≪ Formula 1-1 >
R1 내지 R4는 서로 독립적으로 수소; 중수소; 할로겐; 시아노기; 니트로기; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-N(Ra)(Rb)로 이루어진 군에서 선택될 수 있다.R 1 to R 4 independently of one another are hydrogen; heavy hydrogen; halogen; Cyano; A nitro group; A C 6 to C 60 aryl group; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 to C 60 aliphatic cyclic group; A fused ring group of an aliphatic ring of C 3 to C 60 and an aromatic ring of C 6 to C 60 ; A C 1 to C 50 alkyl group; An alkenyl group having 2 to 20 carbon atoms; An alkynyl group having 2 to 20 carbon atoms; A C 1 to C 30 alkoxyl group; An aryloxy group of C 6 to C 30 ; And -L'-N (R a ) (R b ).
또한, 이웃한 R4끼리 서로 결합하여 고리를 형성할 수 있다. 이때, 고리는 C6~C60의 방향족고리; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; 및 이들의 조합에서 선택될 수 있다.Further, the adjacent R < 4 > may be bonded to each other to form a ring. Wherein the ring is a C 6 to C 60 aromatic ring; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 to C 60 aliphatic cyclic group; And combinations thereof.
l, m 및 n은 각각 0~6의 정수이며, 이들 각각이 2 이상의 정수인 경우, 각각의 R1, 각각의 R2, 각각의 R3, 각각의 R4는 서로 동일하거나 상이하다. o는 0~4의 정수이고, o가 2 이상의 정수인 경우, 각각의 R4는 서로 동일하거나 상이하다.each of R 1 , R 2 , R 3 , and R 4 is the same as or different from each other when l, m and n are integers of 0 to 6, respectively. o is an integer of 0 to 4, and when o is an integer of 2 or more, each R 4 is the same or different from each other.
R1 내지 R4가 아릴기인 경우, 바람직하게는 C6~C30의 아릴기, 더욱 바람직하게는 C6~C18의 아릴기, 예컨대 페닐, 바이페닐, 터페닐, 나프틸 등일 수 있다. R1 내지 R4가 헤테로고리기인 경우, 바람직하게는 C2~C30의 헤테로고리기, 더욱 바람직하게는 C2~C18의 헤테로고리기, 예컨대, 피리미딘, 카바졸, 페닐카바졸, 다이벤조싸이오펜, 다이퓨란, 피리도인돌 등일 수 있다. R1 내지 R4가 플루오렌일기인 경우, 다이메틸플루오렌, 다이페닐플루오렌 등일 수 있다.When R 1 to R 4 are aryl groups, they may preferably be C 6 to C 30 aryl groups, more preferably C 6 to C 18 aryl groups such as phenyl, biphenyl, terphenyl, naphthyl and the like. When R 1 to R 4 are heterocyclic groups, preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 18 heterocyclic group such as pyrimidine, carbazole, phenylcarbazole, Dibenzothiophene, difuran, pyridoindole, and the like. When R 1 to R 4 are fluorenyl groups, they may be dimethylfluorene, diphenylfluorene and the like.
X1는 O 또는 S이고, X2 및 X3은 서로 독립적으로 단일결합, N(-L1-Ar1), O, S 또는 C(R')(R'')이고, X2 및 X3 중 적어도 하나는 단일결합이 아니다.And X 1 is O or S, X 2 and X 3 each is a single bond, independently, N (-L 1 -Ar 1) , O, S or C (R ') (R''), X 2 and X At least one of the three is not a single bond.
상기 L1은 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; C3~C60의 지방족고리기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 이들의 조합으로 이루어진 군에서 선택될 수 있다.L < 1 > is a single bond; An arylene group having 6 to 60 carbon atoms; A fluorenylene group; A C 3 to C 60 aliphatic cyclic group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; And combinations thereof.
상기 L1이 아릴렌기인 경우, 바람직하게는 C6~C30의 아릴렌기, 더욱 바람직하게는 C6~C12의 아릴기, 예컨대 페닐, 나프탈렌, 바이페닐 등일 수 있다. L1이 헤테로고리기인 경우, 바람직하게는 C2~C30의 헤테로고리, 더욱 바람직하게는 C2~C12의 헤테로고리, 예컨대 트리아진, 피리미딘, 피리딘, 퀴나졸린, 퀴녹살린, 벤조싸이에노피리미딘, 벤조퀴나졸린, 퀴놀린, 프탈라진, 피리도피리미딘 등일 수 있다.When L 1 is an arylene group, it may preferably be an arylene group having 6 to 30 carbon atoms, more preferably a C 6 to C 12 aryl group such as phenyl, naphthalene, biphenyl, and the like. When L 1 is a heterocyclic group, preferably a C 2 to C 30 heterocyclic ring, more preferably a C 2 to C 12 heterocyclic ring such as triazine, pyrimidine, pyridine, quinazoline, quinoxaline, Benzoquinazoline, quinoline, phthalazine, pyridopyrimidine, and the like.
상기 Ar1은 C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-N(Ra)(Rb);로 이루어진 군에서 선택될 수 있다.Ar 1 is a C 6 to C 60 aryl group; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 to C 60 aliphatic cyclic group; A fused ring group of an aliphatic ring of C 3 to C 60 and an aromatic ring of C 6 to C 60 ; A C 1 to C 50 alkyl group; An alkenyl group having 2 to 20 carbon atoms; An alkynyl group having 2 to 20 carbon atoms; A C 1 to C 30 alkoxyl group; An aryloxy group of C 6 to C 30 ; And -L'-N (R a ) (R b );
Ar1이 아릴기인 경우, 바람직하게는 C6~C30의 아릴기, 더욱 바람직하게는 C6~C18의 아릴기, 예컨대 페닐, 바이페닐, 나프틸, 트리페닐렌 등일 수 있다. Ar1이 헤테로고리기인 경우, 바람직하게는 C2~C30의 헤테로고리기, 더욱 바람직하게는 C2~C12의 헤테로고리기, 예컨대 트리아진, 피리미딘, 피리딘, 퀴놀린, 벤조퀴놀린, 퀴나졸린, 퀴녹살린, 프탈라진, 피리도피리미딘, 벤조싸이에노피리미딘, 벤조퓨로피리미딘, 벤조퀴나졸린 등일 수 있다.When Ar 1 is an aryl group, it may preferably be an aryl group of C 6 to C 30 , more preferably a C 6 to C 18 aryl group such as phenyl, biphenyl, naphthyl, triphenylene, and the like. When Ar 1 is a heterocyclic group, preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 12 heterocyclic group such as triazine, pyrimidine, pyridine, quinoline, benzoquinoline, quinine Quinoxaline, phthalazine, pyridopyrimidine, benzothienopyrimidine, benzopuropyrimidine, benzoquinazoline, and the like.
상기 R' 및 R"은 수소; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C1~C50의 알킬기; 및 -L'-N(Ra)(Rb)로 이루어진 군에서 선택되고, R', R"은 서로 결합하여 고리를 형성할 수 있다. 이때, 고리는 C6~C60의 방향족고리; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; 및 이들의 조합에서 선택될 수 있다. 바람직하게는, R', R"가 서로 결합하여 고리를 형성하면, 스파이로 화합물이 형성될 수 있다.Wherein R 'and R "is hydrogen; C 6 ~ C aryl group of 60; fluorene group; O, N, S, a heterocyclic of C 2 ~ containing at least one hetero atom of Si and P C 60 group; A C 1 to C 50 alkyl group, and -L'-N (R a ) (R b ), and R 'and R "may combine with each other to form a ring. Wherein the ring is a C 6 to C 60 aromatic ring; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 to C 60 aliphatic cyclic group; And combinations thereof. Preferably, when R 'and R "are bonded to each other to form a ring, a compound can be formed as a spy.
상기 L'은 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; C3~C60의 지방족고리기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 이들의 조합으로 이루어진 군에서 선택될 수 있다.L 'is a single bond; An arylene group having 6 to 60 carbon atoms; A fluorenylene group; A C 3 to C 60 aliphatic cyclic group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; And combinations thereof.
상기 Ra 및 Rb는 서로 독립적으로 C6~C60의 아릴기; 플루오렌일기; C3~C60의 지방족고리기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 이들의 조합으로 이루어진 군에서 선택될 수 있다.R a and R b are each independently a C 6 to C 60 aryl group; A fluorenyl group; A C 3 to C 60 aliphatic cyclic group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; And combinations thereof.
Ra 및 Rb가 아릴기인 경우, 바람직하게는 C6~C30의 아릴기, 더욱 바람직하게는 C6~C18의 아릴기, 예컨대 페닐, 바이페닐, 나프틸, 트리페닐렌 등일 수 있다. Ra 및 Rb가 헤테로고리기인 경우, 바람직하게는 C2~C30의 헤테로고리, 더욱 바람직하게는 C2~C12의 헤테로고리, 예컨대 트리아진, 다이벤조싸이오펜, 다이벤조퓨란 등일 수 있다. Ra 및 Rb가 플루오렌일기인 경우, 다이메틸플루오렌, 다이페닐플루오렌 등일 수 있다.When R a and R b are aryl groups, it is preferably a C 6 to C 30 aryl group, more preferably a C 6 to C 18 aryl group such as phenyl, biphenyl, naphthyl, triphenylene, and the like . When R a and R b are a heterocyclic group, preferably a C 2 to C 30 hetero ring, more preferably a C 2 to C 12 hetero ring such as triazine, dibenzothiophene, dibenzofurane, etc. have. When R a and R b are fluorenyl groups, they may be dimethylfluorene, diphenylfluorene, and the like.
상기 R1 내지 R4, Ar1, L1, R', R", L', Ra, Rb, 및 이웃한 R4끼리 서로 결합하여 형성한 고리는 각각 중수소; 할로겐; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 실란기; 실록산기; 붕소기; 게르마늄기; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕실기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 중수소로 치환된 C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 시클로알킬기; C7-C20의 아릴알킬기; C8-C20의 아릴알켄일기; 및 이들의 조합으로 이루어진 군에서 선택된 하나 이상의 치환기로 더 치환될 수 있다.Wherein R 1 to R 4, Ar 1, L 1 , R ', R ", L', R a, R b, R 4 and the adjacent ring formed by binding to each other, are each heavy hydrogen; halogen; C 1 -C alkyl group or a C 6 aryl group a substituted or unsubstituted silane group of 20 -C 20; siloxane group; a boron group; germanium group; cyano group; nitro group; an alkylthio import of C 1 -C 20; C 1 -C 20 of an alkoxyl group; an alkyl group of C 1 -C 20; an aryl of C 6 -C 20 substituted with heavy hydrogen; C 2 -C 20 alkynyl of;; C 6 aryl group of C 2 -C 20 alkenyl group 20 -C of A C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C 3 -C 20 cycloalkyl group, a C 7 -C 20 heterocyclic group, aryl alkene of C 8 -C 20 group;; C 20 arylalkyl groups and with one or more substituents selected from the group consisting of may be further substituted.
바람직하게는, 상기 화학식 1은 하기 화학식 2 내지 화학식 7 중에서 하나로 표시될 수 있다.Preferably, the formula (1) may be represented by one of the following formulas (2) to (7).
<화학식 2> <화학식 3> <화학식 4>≪ Formula 2 > < EMI ID =
<화학식 5> <화학식 6> <화학식 7>≪ Formula 5 > < EMI ID =
상기 화학식 2 내지 화학식 7에서, R1 내지 R3, l, m, n은 화학식 1에서 정의된 것과 같고, A환, B환 및 C환은 C10~C24의 아릴기이거나, 또는 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C8~C24의 헤테로고리기이다.R 1 to R 3 , l, m and n are as defined in formula (1), A ring, B ring and C ring are C 10 -C 24 aryl groups, or O, N , A C 8 to C 24 heterocyclic group containing at least one hetero atom selected from S, Si and P.
V1 내지 V11은 CH, CR 또는 N이며, 여기서 R은 서로 독립적으로 수소; 중수소; 할로겐; 시아노기; 니트로기; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-N(Ra)(Rb)로 이루어진 군에서 선택되며, L', Ra 및 Rb는 상기에서 정의된 것과 같다.V 1 to V 11 are CH, CR, or N, wherein R is independently from each other hydrogen; heavy hydrogen; halogen; Cyano; A nitro group; A C 6 to C 60 aryl group; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 to C 60 aliphatic cyclic group; A fused ring group of an aliphatic ring of C 3 to C 60 and an aromatic ring of C 6 to C 60 ; A C 1 to C 50 alkyl group; An alkenyl group having 2 to 20 carbon atoms; An alkynyl group having 2 to 20 carbon atoms; A C 1 to C 30 alkoxyl group; An aryloxy group of C 6 to C 30 ; And -L'-N (R a ) (R b ), wherein L ', R a and R b are as defined above.
바람직하게는, A환, B환 및 C환은 하기 화학식 B-1 내지 화학식 B-7로 이루어진 군에서 선택될 수 있다.Preferably, the A ring, B ring and C ring may be selected from the group consisting of the following formulas B-1 to B-7.
상기 화학식 B-1 내지 화학식 B-7에 있어서, "*"표시는 축합되는 위치를 나타내며, Z4 내지 Z50은 CR0 또는 N이다. 이때, R0는 수소; 중수소; 할로겐; 시아노기; 니트로기; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-N(Ra)(Rb)로 이루어진 군에서 선택되고, L', Ra 및 Rb는 상기에서 정의된 것과 같다.In the above formulas (B-1) to (B-7), the symbol "* " indicates the position to be condensed and Z 4 to Z 50 are CR 0 or N. Wherein R < 0 > is hydrogen; heavy hydrogen; halogen; Cyano; A nitro group; A C 6 to C 60 aryl group; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 to C 60 aliphatic cyclic group; A fused ring group of an aliphatic ring of C 3 to C 60 and an aromatic ring of C 6 to C 60 ; A C 1 to C 50 alkyl group; An alkenyl group having 2 to 20 carbon atoms; An alkynyl group having 2 to 20 carbon atoms; A C 1 to C 30 alkoxyl group; An aryloxy group of C 6 to C 30 ; And -L'-N (R a ) (R b ), and L ', R a and R b are as defined above.
또한, 바람직하게는 상기 화학식 1은 하기 화학식 8 내지 화학식 16 중에서 하나로 표시될 수 있다.Preferably, the formula (1) may be represented by one of the following formulas (8) to (16).
<화학식 8> <화학식 9> <화학식 10> ≪ Formula 8 > < EMI ID =
<화학식 11> <화학식 12> <화학식 13> ≪ Formula 11 > < EMI ID =
<화학식 14> <화학식 15> <화학식 16> ≪ Formula 14 > < EMI ID =
상기 화학식 8 내지 화학식 16에서, A환, B환, C환, R1 내지 R4, X1 내지 X3, l, m, n, o는 화학식 1에서 정의된 것과 같고, l'은 0~1의 정수, l"은 0~3의 정수, m'은 0~2의 정수이다.In Formula 8 to Formula 16, A ring, B ring, C ring, R 1 to R 4 , X 1 to X 3 , l, m, n and o are as defined in Formula 1, 1 "is an integer of 0 to 3, and m 'is an integer of 0 to 2.
구체적으로, 상기 화학식 1로 표시되는 화합물은 하기 화합물 중 하나일 수 있다.Specifically, the compound represented by Formula 1 may be one of the following compounds.
본 발명의 다른 실시예로, 제 1전극, 제 2 전극, 및 상기 제 1전극과 상기 제 2전극 사이에 형성된 유기물층을 포함하는 유기전기소자를 제공하며, 이때 유기물층은 화학식 1로 표시되는 단독 화합물 또는 2종 이상의 화합물을 포함하며, 유기물층은 정공주입층, 정공 수송층, 발광보조층, 발광층, 전자수송보조충, 전자 수송층 및 전자 주입층 중 적어도 하나의 층을 포함한다. 바람직하게는, 화학식 1로 표시되는 화합물은 발광층에 포함될 수 있다.According to another embodiment of the present invention, there is provided an organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, wherein the organic layer comprises a single compound Or at least two compounds, and the organic material layer includes at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting auxiliary charge, an electron transporting layer and an electron injection layer. Preferably, the compound represented by the general formula (1) may be contained in the light emitting layer.
이하에서, 본 발명에 따른 화학식으로 표시되는 화합물의 합성예 및 유기전기소자의 제조예에 관하여 실시예를 들어 구체적으로 설명하지만, 본 발명이 하기의 실시예로 한정되는 것은 아니다.Hereinafter, the synthesis examples of the compound represented by the formula according to the present invention and the production example of the organic electric device will be concretely described by way of examples, but the present invention is not limited to the following examples.
합성예Synthetic example
본 발명에 따른 화학식 1로 표시되는 화합물(Final Products)은 하기 반응식 1과 같이 Sub 1 내지 Sub 3을 이용하여 합성될 수 있다.The compound represented by formula (1) according to the present invention can be synthesized using Sub 1 to Sub 3 as shown in Reaction Scheme 1 below.
<반응식 1> (여기서, R5는 H 또는 Br임)(Reaction Scheme 1) (wherein R 5 is H or Br)
I. Sub 1 내지 Sub 3의 I. Sub 1 to Sub 3 합성예Synthetic example
Sub 1의 Sub 1's 합성예Synthetic example
Sub 1(47)의 Sub 1 (47) 합성예Synthetic example
(1) Sub 1-47A의 합성(1) Synthesis of Sub 1-47A
1-fluoro-9H-carbazole ( 20 g, 107.9 mmol)을 톨루엔에 녹인 후에, 6-bromo-2-iodonaphthalen-1-ol ( 45 g, 129.48 mmol)을 넣고 NaOt-Bu ( 31.1 g, 323.7 mmol), Pd2(dba)3 (3 g, 3.24 mmol), P(t-Bu)3 (1.2 g, 1.08 mmol), toluene (300 mL)을 첨가한 뒤, 100℃에서 20시간 교반환류시킨다. 반응이 종료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축시킨다. 이후, 농축물을 실리카겔 칼럼에 통과시킨 후 재결정하여 Sub 1-47A를 27.36 g (수율: 65.6%)을 얻었다.1-fluoro-9H-carbazole (20 g, 107.9 mmol) was dissolved in toluene and then 6-bromo-2-iodonaphthalen-1-ol (45 g, 129.48 mmol) was added. NaO t- Bu (31.1 g, 323.7 mmol ), Pd 2 (dba) 3 (3 g, 3.24 mmol), P (t-Bu) 3 (1.2 g, 1.08 mmol) and toluene (300 mL) And the mixture is refluxed at 100 ° C for 20 hours. After completion of the reaction, the reaction mixture is extracted with ether and water, and the organic layer is dried with MgSO 4 and concentrated. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain 27.36 g of Sub 1-47A (yield: 65.6%).
(2) Sub 1-47의 합성(2) Synthesis of Sub 1-47
Sub 1-47A ( 5 g, 12.30 mmol)을 DMF에 녹인 후에, 60% NaH ( 0.5 g, 12.5 mmol)을 0℃에서 나누어서 첨가한 뒤, 5시간 교반환류시킨다. 반응이 종료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축시킨다. 이후, 농축물을 실리카겔 칼럼에 통과시킨 후 재결정하여 Sub-1-47을 3.36 g (수율: 70.9%) 얻었다.Sub 1-47A (5 g, 12.30 mmol) was dissolved in DMF, and then 60% NaH (0.5 g, 12.5 mmol) was added at 0 ° C and the mixture was refluxed for 5 hours. After completion of the reaction, the reaction mixture is extracted with ether and water, and the organic layer is dried with MgSO 4 and concentrated. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain 3.36 g of Sub-1-47 (yield: 70.9%).
Sub 2의 Sub 2 합성예Synthetic example
Sub 2(20)의 Sub 2 (20) 합성예Synthetic example
(1) Sub 2-20A의 합성(1) Synthesis of Sub 2-20A
9-bromo-6-fluoro-5H-benzo[b]carbazole ( 10 g, 31.83 mmol)을 톨루엔에 녹인 후에, 2-iodobenzenethiol ( 8.2 g, 35.01 mmol)을 넣고 NaOt-Bu ( 9.1 g, 95.49 mmol), Pd2(dba)3 (1.46 g, 1.59 mmol), P(t-Bu)3 (0.64 g, 3.18 mmol), toluene (200 mL)을 각각 첨가한 뒤, 100℃에서 20시간 교반환류시킨다. 반응이 종료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축시킨다. 이후, 농축물을 실리카겔 칼럼에 통과시킨 후 재결정하여 Sub 2-20A를 9.9 g (수율: 73.6%)을 얻었다.After dissolving 9-bromo-6-fluoro-5H-benzo [b] carbazole (10 g, 31.83 mmol) in toluene, 2-iodobenzenethiol (8.2 g, 35.01 mmol) was added and NaO t- ), Pd 2 (dba) 3 (1.46 g, 1.59 mmol), P (t-Bu) 3 (0.64 g, 3.18 mmol) and toluene (200 mL) And the mixture is refluxed at 100 ° C for 20 hours. After completion of the reaction, the reaction mixture is extracted with ether and water, and the organic layer is dried with MgSO 4 and concentrated. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain 9.9 g of Sub 2-20A (yield: 73.6%).
(2) Sub 2-20의 합성(2) Synthesis of Sub 2-20
Sub 2-20A ( 5 g, 11.84 mmol)을 DMF에 녹인 후에, 60% NaH ( 0.5 g, 12.5 mmol)을 0℃에서 나누어서 첨가한 뒤, 5시간 교반 환류시킨다. 반응이 종료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축시킨다. 이후, 농축물을 실리카겔 칼럼에 통과시킨 후 재결정하여 Sub-2-20을 2.3 g (수율: 48.3%) 얻었다.Sub 2-2OA (5 g, 11.84 mmol) was dissolved in DMF, and 60% NaH (0.5 g, 12.5 mmol) was added at 0 ° C in portions while the mixture was refluxed for 5 hours. After completion of the reaction, the reaction mixture is extracted with ether and water, and the organic layer is dried with MgSO 4 and concentrated. Subsequently, the concentrate was passed through a silica gel column and then recrystallized to obtain 2.3 g (yield: 48.3%) of Sub-2-20.
Sub 2(39)의 Sub 2 (39) 합성예Synthetic example
(1) Sub 2-39A의 합성(1) Synthesis of Sub 2-39A
12H-benzo[b]phenoxazine ( 10 g, 42.87 mmol)을 톨루엔에 녹인 후에, 1-bromo-2-iodobenzene ( 13.3 g, 47.16 mmol)을 넣고 NaOt-Bu ( 12.3 g, 128.61 mmol), Pd2(dba)3 (1.96 g, 2.14 mmol), P(t-Bu)3 (0.87 g, 4.29 mmol), toluene (300 mL)을 각각 첨가한 뒤, 100℃에서 20시간 교반환류시킨다. 반응이 종료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축시킨다. 이후, 농축물을 실리카겔 칼럼에 통과시킨 후 재결정하여 Sub 2-39A를 11.8 g (수율: 70.9%)을 얻었다.Bromo-2-iodobenzene (13.3 g, 47.16 mmol) was added to the solution, and NaO t- Bu (12.3 g, 128.61 mmol) and Pd 2 (dba) 3 (1.96 g, 2.14 mmol), P (t-Bu) 3 (0.87 g, 4.29 mmol) and toluene (300 mL) And the mixture is refluxed at 100 ° C for 20 hours. After completion of the reaction, the reaction mixture is extracted with ether and water, and the organic layer is dried with MgSO 4 and concentrated. Thereafter, the concentrate was passed through a silica gel column and then recrystallized to obtain 11.8 g of Sub 2-39A (yield: 70.9%).
(2) Sub 2-39B의 합성(2) Synthesis of Sub 2-39B
Sub 2-39A ( 8 g, 20.60 mmol)을 DMA에 녹인 후에, Pd(OAc)2 ( 0.46 g, 2.06 mmol) 을 넣고, PCy3HBF4 ( 1.5 g, 4.12 mmol), K2CO3 ( 5.7 g, 41.2 mmol), DME (100 mL)을 각각 첨가한 뒤, 4시간 교반환류시킨다. 반응이 종료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축시킨다. 이후, 농축물을 실리카겔 칼럼에 통과시킨 후 재결정하여 Sub 2-39B를 3.8 g (수율: 60%)을 얻었다.Pd (OAc) 2 (0.46 g, 2.06 mmol) was added to the reaction solution and then PCy 3 HBF 4 (1.5 g, 4.12 mmol) and K 2 CO 3 (5.7 g, 41.2 mmol) and DME (100 mL) were added, and the mixture was refluxed for 4 hours. After completion of the reaction, the reaction mixture is extracted with ether and water, and the organic layer is dried with MgSO 4 and concentrated. Thereafter, the concentrate was passed through a silica gel column and then recrystallized to obtain 3.8 g (yield: 60%) of Sub 2-39B.
(3) Sub 2-39의 합성(3) Synthesis of Sub 2-39
Sub 2-39B ( 3 g, 9.76 mmol)을 MC에 녹인 후, 0℃에서 NBS ( 1.56 g, 8.8 mmol) 을 천천히 넣고 상온에서 5시간 동안 교반시킨다. 반응이 종료되면 물을 넣고 생성된 유기물을 필터링한 후, 실리카겔 칼럼에 통과시킨 후 재결정하여 Sub 2-39를 2.9 g (수율: 76.9%)을 얻었다.Sub 2-39B (3 g, 9.76 mmol) was dissolved in MC, NBS (1.56 g, 8.8 mmol) was slowly added at 0 ° C, and the mixture was stirred at room temperature for 5 hours. After the completion of the reaction, water was added thereto, and the resulting organic material was filtered. The filtrate was passed through a silica gel column and recrystallized to obtain 2.9 g (Yield: 76.9%) of Sub 2-39.
Sub 3의 Sub 3 합성예Synthetic example
Sub 3(40)의 Sub 3 (40) 합성예Synthetic example
(1) Sub 3-40A의 합성(1) Synthesis of Sub 3-40A
1-fluoronaphthalen-2-ol ( 20 g, 123.33 mmol), NaHSO3 ( 25.67 g, 246.66 mmol), (4-bromophenyl)hydrazine ( 27.7 g, 147.99 mmol)을 증류수 160 mL에 넣고 100℃ 에서 14시간 동안 교반환류시킨다. 염산 수용액을 넣고 100℃에서 1시간 교반시킨다. 반응이 종료되면 MC로 추출한 후 유기층을 MgSO4로 건조하고 농축시킨다. 이후, 농축물을 실리카겔 칼럼에 통과시킨 후 재결정하여 Sub 3-40A를 7.40 g (수율: 19.1%)을 얻었다.1-fluoronaphthalen-2-ol ( 20 g, 123.33 mmol), NaHSO 3 (25.77 g, 246.66 mmol) and (4-bromophenyl) hydrazine (27.7 g, 147.99 mmol) were added to 160 mL of distilled water and the mixture was refluxed at 100 ° C for 14 hours. Hydrochloric acid aqueous solution, and the mixture is stirred at 100 占 폚 for 1 hour. After the reaction is completed, the reaction mixture is extracted with MC, and the organic layer is dried with MgSO 4 and concentrated. Thereafter, the concentrate was passed through a silica gel column and then recrystallized to obtain 7.40 g of Sub 3-40A (yield: 19.1%).
(2) Sub 3-40B의 합성(2) Synthesis of Sub 3-40B
Sub 3-40A ( 10 g, 31.83 mmol)을 톨루엔에 녹인 후에, 2-iodophenol ( 7.7 g, 35.01 mmol)을 넣고 NaOt-Bu( 9.2 g, 95.49 mmol), Pd2(dba)3 ( 1.4 g 1.6 mmol), P(t-Bu)3 ( 0.56 g, 3.2 mmol), toluene (200 mL)을 각각 첨가한 뒤, 100℃ 에서 20시간 교반환류시킨다. 반응이 종료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축시킨다. 이후, 농축물을 실리카겔 칼럼에 통과시킨 후 재결정하여 Sub 3-40B를 7.4 g (수율: 57.2%)을 얻었다.Sub 3-40A (10 g, 31.83 mmol ) was dissolved in toluene, into a 2-iodophenol (7.7 g, 35.01 mmol) NaO t -Bu (9.2 g, 95.49 mmol), Pd 2 (dba) 3 (1.4 g 1.6 mmol), P (t-Bu) 3 (0.56 g, 3.2 mmol) and toluene (200 mL) And the mixture is refluxed at 100 ° C for 20 hours. After completion of the reaction, the reaction mixture is extracted with ether and water, and the organic layer is dried with MgSO 4 and concentrated. Subsequently, the concentrate was passed through a silica gel column and recrystallized to obtain 7.4 g (yield: 57.2%) of Sub 3-40B.
(3) Sub 3-40의 합성(3) Synthesis of Sub 3-40
Sub 3-40B ( 5 g, 12.31 mmol)을 DMF에 녹인 후에, 60% NaH ( 0.52 g, 13.17 mmol)을 0℃ 에서 나누어서 첨가한 뒤, 5시간 교반환류시킨다. 반응이 종료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축시킨다. 이후, 농축물을 실리카겔 칼럼에 통과시킨 후 재결정하여 Sub 3-40을 2.3 g (수율: 48.4%) 얻었다.After sub-3-40B (5 g, 12.31 mmol) was dissolved in DMF, 60% NaH (0.52 g, 13.17 mmol) was added at 0 ° C and the mixture was refluxed for 5 hours. After completion of the reaction, the reaction mixture is extracted with ether and water, and the organic layer is dried with MgSO 4 and concentrated. Subsequently, the concentrate was passed through a silica gel column and then recrystallized to obtain 2.3 g (yield: 48.4%) of Sub 3-40.
Sub 1-1-A의 Sub 1-1-A 합성예Synthetic example
반응식 1의 Sub 1 내지 Sub 3에서 L1이 단일결합이 아닐 경우, 하기 반응식 2의 반응경로에 의해 합성될 수 있으나, 이에 한정된 것은 아니다. In Sub 1 to Sub 3 of Reaction Scheme 1, when L 1 is not a single bond, it may be synthesized by the reaction path of the following reaction scheme 2, but is not limited thereto.
<반응식 2><Reaction Scheme 2>
Sub 1 내지 Sub 3에 속하는 화합물은 다음과 같으나, 이에 한정되는 것은 아니며, 하기 화합물에 대한 FD-MS 값은 하기 표 1과 같다.The compounds belonging to Sub 1 to Sub 3 are as follows, but the present invention is not limited thereto. FD-MS values for the following compounds are shown in Table 1 below.
[표 1][Table 1]
Ⅱ. Sub-4의 Ⅱ. Sub-4's 합성예Synthetic example
Sub 4-1의 Sub 4-1 합성예Synthetic example
둥근바닥플라스크에 bromobenzene (37.1 g, 236.2 mmol)을 넣고 toluene (2200 mL)으로 녹인 후 aniline (20 g, 214.8 mmol), Pd2(dba)3 (9.83 g, 10.7 mmol), P(t-Bu)3 (4.34 g, 21.5 mmol), NaOt-Bu (62 g, 644.3 mmol)을 순서대로 첨가하고 100℃에서 교반하였다. 반응이 완료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축시켰다. 이후, 농축물을 실리카겔 칼럼에 통과시킨 후 재결정하여 생성물 28 g (수율: 77%)를 얻었다.Then put the bromobenzene (37.1 g, 236.2 mmol) in a round bottom flask was dissolved in toluene (2200 mL) aniline (20 g, 214.8 mmol), Pd 2 (dba) 3 (9.83 g, 10.7 mmol), P (t -Bu ) 3 (4.34 g, 21.5 mmol) and NaO t- Bu (62 g, 644.3 mmol) were added in this order and stirred at 100 ° C. After completion of the reaction, the reaction mixture was extracted with ether and water, and the organic layer was dried with MgSO 4 and concentrated. Thereafter, the concentrate was passed through a silica gel column and then recrystallized to obtain 28 g of a product (yield: 77%).
Sub 4-14의 Sub 4-14 합성예Synthetic example
3-bromodibenzo[b,d]furan (40.2 g, 162.5 mmol), toluene(1550 mL), [1,1'-biphenyl]-4-amine (25 g, 147.7 mmol), Pd2(dba)3 (6.76 g, 7.4 mmol), P(t-Bu)3 (3 g, 14.8 mmol), NaOt-Bu (42.6 g, 443.2 mmol)을 사용하여 상기 Sub 4-1의 합성법과 같은 방법으로 생성물 36.8 g (수율: 71%)를 얻었다.4-amine (25 g, 147.7 mmol), Pd 2 (dba) 3 ( 1 H), 3-bromodibenzo [b, d] furan (40.2 g, 162.5 mmol) (42.6 g, 443.2 mmol), P ( t- Bu) 3 (3 g, 14.8 mmol) and NaO t- Bu (6.76 g, 7.4 mmol) (Yield: 71%).
Sub 4의 예시적 화합물은 다음과 같으나, 이에 한정되는 것은 아니며, 하기 화합물에 대한 FD-MS 값은 하기 표 2와 같다.Exemplary compounds of Sub 4 include, but are not limited to, FD-MS values for the following compounds are shown in Table 2 below.
[표 2] [Table 2]
Ⅲ. Sub 5의 예시Ⅲ. Example of Sub 5
Sub 5에 속하는 화합물은 아래와 같은 화합물일 수 있으나, 이에 한정되는 것은 아니며, 하기 표 3은 Sub 5에 속하는 화합물의 FD-MS 값을 나타낸 것이다.The compounds belonging to Sub 5 may be, but not limited to, the following compounds, and Table 3 below shows the FD-MS values of Sub 5 compounds.
[표 3][Table 3]
Ⅳ. 최종화합물의 IV. Of the final compound 합성예Synthetic example
1. 1-60의 합성 예시1. Synthetic examples of 1-60
(( 1)Sub1) Sub 1-12-A의 합성 Synthesis of 1-12-A
Sub 1-12 ( 10 g, 24.9 mmol)을 톨루엔에 녹인 후에, 2-chloroaniline (3.65 g, 28.6 mmol)을 넣고 NaOt-Bu (7.17 g, 74.6 mmol), Pd2(dba)3 (1.14 g, 1.24 mmol), P(t-Bu)3 (0.6 g, 2.49 mmol), toluene (300 mL)을 각각 첨가한 뒤, 100℃ 에서 24시간 교반환류시켰다. 반응이 종료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축시켰다. 이후, 농축물을 실리카겔 칼럼에 통과시킨 후 재결정하여 Sub 1-12-A을 7.92 g (수율: 71%)을 얻었다.Sub 1-12 (10 g, 24.9 mmol ) was dissolved in toluene, 2-chloroaniline put (3.65 g, 28.6 mmol) NaO t -Bu (7.17 g, 74.6 mmol), Pd 2 (dba) 3 (1.14 g , 1.24 mmol), P (t-Bu) 3 (0.6 g, 2.49 mmol) and toluene (300 mL) And the mixture was stirred and refluxed at 100 ° C for 24 hours. After the reaction was completed, the reaction mixture was extracted with ether and water, and the organic layer was dried with MgSO 4 and concentrated. Thereafter, the concentrate was passed through a silica gel column and then recrystallized to obtain 7.92 g of Sub 1-12-A (yield: 71%).
(2) Sub 1-12-B의 합성(2) Synthesis of Sub 1-12-B
Sub 1-12-A (3.5 g, 7.8 mmol)에 Pd(OAc)2 (0.09 g, 0.39 mmol), P(t-Bu)3 (0.16 g, 0.78 mmol), K2CO3 (3.23 g, 23.39 mmol), DMA (50 ml)을 넣고 170℃에서 12시간 환류시킨다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, MC로 추출하고 물로 닦아준 후, 유기층을 MgSO4로 건조하고 농축시켰다. 이후, 농축물을 실리카겔 칼럼에 통과시킨 후 재결정하여 Sub 1-7B 2.53 g (수율: 79%)을 얻었다.P (t-Bu) 3 (0.16 g, 0.78 mmol), K 2 CO 3 (3.23 g, 0.39 mmol), Pd (OAc) 2 (0.09 g, 23.39 mmol) and DMA (50 ml), and the mixture was refluxed at 170 ° C for 12 hours. After the completion of the reaction, the temperature of the reaction mixture was cooled to room temperature, extracted with MC, wiped with water, and then the organic layer was dried with MgSO 4 and concentrated. Thereafter, the concentrate was passed through a silica gel column and then recrystallized to obtain 2.53 g of Sub 1-7B (yield: 79%).
(3) 1-60의 합성(3) Synthesis of 1-60
Sub 1-12-B (5 g, 12.61 mmol)을 톨루엔에 녹인 후에, Sub 5-3 ( 4.99 g, 14.5 mmol)을 넣고 NaOt-Bu (3.64 g, 37.84 mmol), Pd2(dba)3 (0.58 g, 0.63 mmol), P(t-Bu)3 (0.31 g, 1.26 mmol), toluene (100 mL)을 각각 첨가한 뒤, 100℃에서 24시간 교반환류시킨다. 반응이 종료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축시켰다. 이후, 농축물을 실리카겔 칼럼에 통과시킨 후 재결정하여 화합물 1-60을 5.50 g (수율: 63%) 얻었다.After the Sub 1-12-B (5 g, 12.61 mmol) was dissolved in toluene, Sub 5-3 (4.99 g, 14.5 mmol) into a NaO t -Bu (3.64 g, 37.84 mmol), Pd 2 (dba) 3 (0.58 g, 0.63 mmol), P (t-Bu) 3 (0.31 g, 1.26 mmol) and toluene (100 mL) And the mixture is refluxed with stirring at 100 ° C for 24 hours. After the reaction was completed, the reaction mixture was extracted with ether and water, and the organic layer was dried with MgSO 4 and concentrated. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain 5.50 g (yield: 63%) of Compound 1-60.
2. 1-39의 합성 예시2. Synthetic examples of 1-39
(1) Sub 3-14-A의 합성(1) Synthesis of Sub 3-14-A
Sub 3-14 (6 g, 15.53 mmol)에 bis(pinacolato)diboron (5.13 g, 20.19 mmol), PdCl2(dppf)2 (0.57 g, 0.78 mmol), KOAc (4.57 g, 46.6 mmol), DMF (120 ml)을 넣고 120℃에서 7시간 환류시킨다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, MC로 추출하고 물로 닦아준 후, 유기층을 MgSO4로 건조하고 농축시킨다. 이후, 농축물을 실리카겔 칼럼을 이용하여 분리하여 Sub 3-14A를 5.32 g (수율: 79%)을 얻었다.To a solution of Sub3-14 (6 g, 15.53 mmol) was added bis (pinacolato) diboron (5.13 g, 20.19 mmol), PdCl 2 (dppf) 2 (0.57 g, 0.78 mmol), KOAc (4.57 g, 46.6 mmol) 120 ml) was added, and the mixture was refluxed at 120 ° C for 7 hours. When the reaction is completed, the temperature of the reaction is cooled to room temperature, extracted with MC, wiped with water, and the organic layer is dried with MgSO 4 and concentrated. Thereafter, the concentrate was separated using a silica gel column to obtain 5.32 g of Sub 3-14A (yield: 79%).
(2) Sub 3-14-B의 합성(2) Synthesis of Sub 3-14-B
Sub 3-14-A (5 g, 11.54 mmol)에 1-bromo-2-nitrobenzene (3.03 g, 15 mmol), Pd(PPh3)4 (0.67 g, 0.58 mmol), K2CO3 (4.78 g, 34.62 mmol), THF (100 ml), EtOH (50 ml), H2O (50 ml)을 넣고 90℃에서 12시간 환류시킨다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, MC로 추출하고 물로 닦아준 후, 유기층을 MgSO4로 건조하고 농축시킨다. 이후, 농축물을 실리카겔 칼럼을 이용하여 분리하여 Sub 1-14B를 2.82 g (수율: 0.57%)을 얻었다.Sub 3-14-A (5 g, 11.54 mmol) in 1-bromo-2-nitrobenzene ( 3.03 g, 15 mmol), Pd (PPh 3) 4 (0.67 g, 0.58 mmol), K 2 CO 3 (4.78 g , 34.62 mmol), THF (100 ml), EtOH (50 ml) and H 2 O (50 ml) were added and refluxed at 90 ° C for 12 hours. When the reaction is completed, the temperature of the reaction is cooled to room temperature, extracted with MC, wiped with water, and the organic layer is dried with MgSO 4 and concentrated. Thereafter, the concentrate was separated using a silica gel column to obtain 2.82 g of Sub 1-14B (yield: 0.57%).
(3) Sub 3-14-C의 합성(3) Synthesis of Sub 3-14-C
Sub 3-14-B (10 g, 23.34 mol)와 triphenylphosphine (0.7 mol)을 o-dichlorobenzene에 녹이고, 24시간 동안 환류시켰다. 반응이 종결되면 감압 증류를 이용하여 용매를 제거한 후, 농축된 생성물을 실리카겔 칼럼에 통과시킨 후 재결정하여 Sub 3-14-C를 4.2g (수율: 44.2%) 얻었다.Sub 3-14-B (10 g, 23.34 mol) and triphenylphosphine (0.7 mol) were dissolved in o- dichlorobenzene and refluxed for 24 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and the concentrated product was passed through a silica gel column and recrystallized to obtain 4.2 g (yield: 44.2%) of Sub 3-14-C.
(4) 1-51의 합성(4) Synthesis of 1-51
Sub 3-14-C (4 g, 10.09 mmol)을 톨루엔에 녹인 후에, Sub 5-74 (3.37 g, 11.6 mmol)을 넣고 NaOt-Bu (2.91 g, 30.27 mmol), Pd2(dba)3 (0.46 g, 0.5 mmol), P(t-Bu)3 (0.2 g, 1.01 mmol), toluene (100 mL)을 각각 첨가한 뒤, 100℃에서 24시간 교반환류시킨다. 반응이 종료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼에 통과시킨 후 재결정하여 최종화합물 3.18 g (수율: 52%)을 얻었다.After the Sub 3-14-C (4 g, 10.09 mmol) was dissolved in toluene, into the Sub 5-74 (3.37 g, 11.6 mmol) NaO t -Bu (2.91 g, 30.27 mmol), Pd 2 (dba) 3 (0.46 g, 0.5 mmol), P (t-Bu) 3 (0.2 g, 1.01 mmol) and toluene (100 mL) And the mixture is refluxed with stirring at 100 ° C for 24 hours. After completion of the reaction, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was passed through a silica gel column and then recrystallized to obtain 3.18 g (yield: 52%) of the final compound.
3. 2-42의 3. In 2-42 합성예Synthetic example
(1) Sub 2-24-A의 합성(1) Synthesis of Sub 2-24-A
Sub 2-24 (4 g, 10.36 mmol)에 bis(pinacolato)diboron (3.42 g, 13.46 mmol), PdCl2(dppf)2 (0.38 g, 0.52 mmol), KOAc (3.05 g, 31.07 mmol), DMF (100 ml)을 넣고 120℃에서 7시간 환류시킨다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, MC로 추출하고 물로 닦아준 후 유기층을 MgSO4로 건조하고 농축한다. 이후, 농축물을 실리카겔 칼럼을 이용하여 분리하여 Sub 2-24-A를 3.28 g (수율: 73%)을 얻었다.(3.38 g, 13.46 mmol), PdCl 2 (dppf) 2 (0.38 g, 0.52 mmol), KOAc (3.05 g, 31.07 mmol),
(2) Sub 2-24-B의 합성(2) Synthesis of Sub 2-24-B
Sub 2-24-A (7g, 16.15 mmol)에 2-bromophenol (3.63 g, 21 mmol), Pd(PPh3)4 (0.93 g, 0.81 mmol), K2CO3 (6.7 g, 48.46 mmol), THF (140 ml), EtOH (70 ml), H2O (70 ml)을 넣고 90℃에서 12시간 환류시킨다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, MC로 추출하고 물로 닦아준 후 유기층을 MgSO4로 건조하고 농축한다. 이후, 농축물을 실리카겔 칼럼을 이용하여 분리하여 Sub 2-24-B를 3.94 g (수율: 61%)을 얻었다.Sub 2-24-A (7g, 16.15 mmol) 2-bromophenol (3.63 g, 21 mmol), Pd (PPh 3) 4 (0.93 g, 0.81 mmol), K 2 CO 3 (6.7 g, 48.46 mmol) in, THF (140 ml), EtOH (70 ml) and H 2 O (70 ml) were added, and the mixture was refluxed at 90 ° C for 12 hours. After the completion of the reaction, the reaction mixture is cooled to room temperature, extracted with MC, wiped with water, and the organic layer is dried with MgSO 4 and concentrated. Thereafter, the concentrate was separated using a silica gel column to obtain 3.94 g (yield: 61%) of Sub 2-24-B.
(3) 2-42의 합성(3) Synthesis of 2-42
Sub 2-24-B (3.5 g, 8.76 mmol), Pd(OAc)2 (0.1 g, 0.44 mmol), 3-nitropyridine (0.06 g, 0.44 mmol), BzOOtBu (tert-butyl peroxybenzoate) (3.4 g, 17.52 mmol), C6F6 (hexafluorobenzene) (100 ml), DMI (N,N'-dimethylimidazolidinone) (65 ml)을 넣고 90℃에서 3시간 환류시킨다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, EA로 추출하고 물로 닦아준 후 유기층을 MgSO4로 건조하고 농축시킨다. 이후, 농축물을 실리카겔 칼럼을 이용하여 분리하여 생성물 1.4 g (수율: 40%)을 얻었다.3-nitropyridine (0.06 g, 0.44 mmol), BzOOtBu (tert-butyl peroxybenzoate) (3.4 g, 17.52 mmol), Pd (OAc) 2 (0.1 g, 0.44 mmol) mmol), C 6 F 6 (hexafluorobenzene) (100 ml) and DMI (N, N'-dimethylimidazolidinone) (65 ml) were added and refluxed at 90 ° C for 3 hours. At the end of the reaction, the reaction mixture is cooled to room temperature, extracted with EA, wiped with water, and the organic layer is dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated using a silica gel column to obtain 1.4 g (yield: 40%) of the product.
4. 3-45의 4. 3-45 합성예Synthetic example
(1) Sub 2-30-A의 합성(1) Synthesis of Sub 2-30-A
Sub 2-30 (8 g, 20.71 mmol)에 bis(pinacolato)diboron (6.84 g, 26.93 mmol), PdCl2(dppf)2 (0.76 g, 1.04 mmol), KOAc (6.1 g, 62.14 mmol), DMF (250 ml)을 넣고 120℃에서 7시간 환류시킨다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, MC로 추출하고 물로 닦아준 후, 유기층을 MgSO4로 건조하고 농축시킨다. 이후, 농축물을 실리카겔 칼럼을 이용하여 분리하여 Sub 2-30-A를 7.18 g (수율: 80%)을 얻었다.To a solution of bis (pinacolato) diboron (6.84 g, 26.93 mmol), PdCl 2 (dppf) 2 (0.76 g, 1.04 mmol), KOAc (6.1 g, 62.14 mmol), DMF 250 ml), and the mixture is refluxed at 120 ° C for 7 hours. When the reaction is completed, the temperature of the reaction is cooled to room temperature, extracted with MC, wiped with water, and the organic layer is dried with MgSO 4 and concentrated. Thereafter, the concentrate was separated using a silica gel column to obtain 7.18 g (yield: 80%) of Sub 2-30-A.
(2) Sub 2-30-B의 합성(2) Synthesis of Sub 2-30-B
Sub 2-30-A (6 g, 13.85 mmol)에 methyl 5-bromo-2-iodobenzoate (6.14 g, 18 mmol), Pd(PPh3)4 (0.8 g, 0.69 mmol), K2CO3 (5.74 g, 41.54 mmol), THF (90 ml), EtOH (45 ml), H2O (45 ml)을 넣고 90℃에서 14시간 환류시킨다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, MC로 추출하고 물로 닦아준 후, 유기층을 MgSO4로 건조하고 농축시킨다. 이후, 농축물을 실리카겔 칼럼을 이용하여 분리하여 Sub 2-30-B를 3.96 g (수율: 55%)을 얻었다.Sub 2-30-A in (6 g, 13.85 mmol) methyl 5-bromo-2-iodobenzoate (6.14 g, 18 mmol), Pd (PPh 3) 4 (0.8 g, 0.69 mmol), K 2 CO 3 (5.74 g, 41.54 mmol), THF (90 ml), EtOH (45 ml) and H 2 O (45 ml) were added and refluxed at 90 ° C for 14 hours. When the reaction is completed, the temperature of the reaction is cooled to room temperature, extracted with MC, wiped with water, and the organic layer is dried with MgSO 4 and concentrated. Thereafter, the concentrate was separated using a silica gel column to obtain 3.96 g of Sub 2-30-B (yield: 55%).
(3) Sub 2-30-C의 합성(3) Synthesis of Sub 2-30-C
Sub 2-30-B (3.9 g, 7.5 mmol), THF (70 ml)을 넣고 0℃에서 1.6M methylmagnesium bromide (11.7 ml)을 넣고 상온에서 24시간 교반한다. 반응이 종료되면 1N HCl을 넣고 10분간 교반한 뒤, EA로 추출하고 물로 닦아준다. 이후, 유기층을 MgSO4로 건조하고 농축한 후 생성된 유기물을 실리카겔 칼럼을 이용하여 분리하여 Sub 2-30-C를 2.6 g (수율: 66%)을 얻었다.Add Sub-2-30-B (3.9 g, 7.5 mmol) and THF (70 ml), add 1.6 M methylmagnesium bromide (11.7 ml) at 0 ° C and stir at room temperature for 24 hours. When the reaction is complete, add 1 N HCl and stir for 10 minutes, then extract with EA and wipe with water. Subsequently, the organic layer was dried over MgSO 4 and concentrated. The resulting organic material was separated using a silica gel column to obtain 2.6 g (yield: 66%) of Sub 2-30-C.
(4) Sub 2-30-D의 합성(4) Synthesis of Sub 2-30-D
Sub 2-30-B (2.4 g, 4.6 mmol)를 THF (70 ml)에 녹인 뒤, 0℃에서 2ml의 methanesulfonic acid를 천천히 넣고 상온에서 1시간 교반한다. 반응이 종료되면 sodium carbonate 수용액 (50 ml)을 넣어 10분간 교반한 뒤, MC로 추출하고 물로 닦아준다. 이후, 유기층을 MgSO4로 건조하고 농축한 후 생성된 유기물을 실리카겔 칼럼을 이용하여 분리하여 Sub 2-30-D를 1.1 g (수율: 47%)을 얻었다.Sub 2-30-B (2.4 g, 4.6 mmol) was dissolved in THF (70 ml), and 2 ml of methanesulfonic acid was slowly added at 0 ° C and stirred at room temperature for 1 hour. After the reaction is completed, add sodium carbonate aqueous solution (50 ml), stir for 10 minutes, extract with MC and wipe with water. Thereafter, the organic layer was dried over MgSO 4 and concentrated. The resulting organic material was separated using a silica gel column to obtain 1.1 g (yield: 47%) of Sub 2-30-D.
(5) 3-45의 합성(5) Synthesis of 3-45
Sub 2-30-D (3 g, 5.97 mmol)을 톨루엔에 녹인 후에, Sub 4-9 (2.8 g, 6.87 mmol)을 넣고 NaOt-Bu (1.72 g, 17.91 mmol), Pd2(dba)3 (0.27 g, 0.3 mmol), P(t-Bu)3 (0.12 g, 0.6 mmol), toluene (70 mL)을 각각 첨가한 뒤, 100℃에서 24시간 교반환류시킨다. 반응이 종료되면 ether와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축시킨다. 이후, 농축물을 실리카겔 칼럼에 통과시킨 후 재결정하여 최종화합물 2.06 g (수율: 49%)을 얻었다.After the Sub 2-30-D (3 g, 5.97 mmol) was dissolved in toluene, into the Sub 4-9 (2.8 g, 6.87 mmol) NaO t -Bu (1.72 g, 17.91 mmol), Pd 2 (dba) 3 (0.27 g, 0.3 mmol), P (t-Bu) 3 (0.12 g, 0.6 mmol) and toluene (70 mL) And the mixture is refluxed with stirring at 100 ° C for 24 hours. After completion of the reaction, the reaction mixture is extracted with ether and water, and the organic layer is dried with MgSO 4 and concentrated. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain 2.06 g (yield: 49%) of the final compound.
한편, 상기와 같은 합성예에 따라 제조된 본 발명의 화합물 1-1 내지 3-56의 FD-MS 값은 하기 표 4와 같다.The FD-MS values of the compounds 1-1 to 3-56 of the present invention prepared according to the above Synthesis Examples are shown in Table 4 below.
[표 4] [Table 4]
유기전기소자의 제조평가Evaluation of manufacturing of organic electric device
[실시예 1] 레드유기전기 발광소자[Example 1] Red organic electroluminescence device
유리 기판에 형성된 ITO층(양극) 상에 N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (이하 "2-TNATA"로 약기함) 막을 진공증착하여 60 nm 두께의 정공주입층을 형성하였다. 상기정공주입층 상에 Bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (이하 "NPB"로 약기함)을 60 nm 두께로 진공증착하여 정공수송층을 형성한 이후, 호스트로 본 발명의 화합물 1-3을, 도판트로 bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate (이하, "(piq)2Ir(acac) "라 약기함)을 95:5 중량비로 사용하여 상기 정공수송층 상에 30nm 두께의 발광층을 증착하였다. 다음으로, 상기 발광층 상에 (1,1'-비스페닐)-4-올레이토)비스(2-메틸-8-퀴놀린올레이토)알루미늄(이하 "BAlq"로 약기함)을 10 nm 두께로 진공증착하여 정공저지층을 형성하고, 상기 정공수송층 상에 트리스(8-퀴놀리놀)알루미늄(이하 "Alq3"로 약칭함)을 40 nm 두께로 성막하여 전자수송층을 형성하였다. 이후, 상기 전자수송층 상에 LiF를 0.2 nm 두께로 증착하여 전자주입층을 형성한 이후, 전자주입층 상에 Al을 150 nm의 두께로 증착하여 음극을 형성하였다.N 1 on the ITO layer (anode) formed on the glass substrate - (naphthalen-2-yl) -N 4, N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl) -N 1 -phenylbenzene -1,4-diamine (hereinafter abbreviated as "2-TNATA") was vacuum-deposited to form a hole injection layer having a thickness of 60 nm. Bis (1-naphthalenyl) -N, N'-bis-phenyl- (1,1'-biphenyl) -4,4'-diamine (hereinafter abbreviated as NPB) was deposited on the hole injection layer to a thickness of 60 nm (1-phenylisoquinolyl) iridium (III) acetylacetonate (hereinafter referred to as "(piq) 2 Ir (acac)") as a host. A light emitting layer with a thickness of 30 nm was deposited on the hole transporting layer at a weight ratio of 95: 5. Next, aluminum (1,1'-biphenyl) -4-oleato) bis (2-methyl-8-quinolinolato) aluminum Tris (8-quinolinol) aluminum (hereinafter abbreviated as "Alq 3 ") was deposited on the hole transport layer to a thickness of 40 nm to form an electron transport layer. Thereafter, LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and then Al was deposited to a thickness of 150 nm on the electron injection layer to form a cathode.
[[ 실시예Example 2] 내지 [ 2] to [ 실시예Example 36] 36]
발광층의 호스트 물질로 본 발명의 화합물 1-3 대신 하기 표 4에 기재된 본 발명의 화합물을 사용한 점을 제외하고는 상시 실시예 1과 동일한 방법으로 유기전기발광소자를 제조하였다.An organic electroluminescent device was prepared in the same manner as in Example 1 except that the compound of the present invention described in Table 4 was used instead of the compound 1-3 of the present invention as a host material of the light emitting layer.
[[ 비교예Comparative Example 1] 및 [ 1] and [ 비교예Comparative Example 2] 2]
발광층의 호스트 물질로 본 발명의 화합물 1-1 대신 하기 비교화합물 A 및 비교화합물 B를 사용한 점을 제외하고는 상기 실시예 1과 동일한 방법으로 유기전기발광소자를 제작하였다.An organic electroluminescence device was prepared in the same manner as in Example 1, except that the following Comparative Compound A and Comparative Compound B were used instead of the compound 1-1 of the present invention as a host material in the light emitting layer.
<비교화합물 A> <비교화합물 B>≪ Comparative Compound A > < Comparative Compound B >
이와 같이 제조된 실시예 및 비교예 유기전기발광소자들에 순바이어스 직류전압을 가하여 포토리서치(photoresearch)사의 PR-650으로 전기발광(EL) 특성을 측정하였으며, 그 측정 결과 2500cd/m2 기준 휘도에서 맥사이언스사에서 제조된 수명 측정 장비를 통해 T95 수명을 측정하였으며, 그 결과는 하기 표 5와 같다. Electroluminescence (EL) characteristics were measured with PR-650 manufactured by photoresearch by applying a forward bias DC voltage to the organic electroluminescent devices thus manufactured and the comparative organic electroluminescence devices, and the measured luminance was 2500 cd / m 2 standard luminance The T95 lifetime was measured by a life measuring apparatus manufactured by Mac Science Inc. The results are shown in Table 5 below.
[표 5][Table 5]
상기 표 5의 결과로부터 알 수 있듯이, 본 발명의 화합물을 인광호스트로 사용할 경우, 유기전기발광소자의 구동전압을 낮출 수 있고, 효율 및 수명을 현저히 개선시킬 수 있다.As can be seen from the results of Table 5, when the compound of the present invention is used as a phosphorescent host, the driving voltage of the organic electroluminescent device can be lowered, and the efficiency and lifetime can be remarkably improved.
보다 상세히 살펴보면, 일반적으로 호스트 물질로 사용되는 CBP인 비교화합물 A보다 메인 골격으로 인돌이 축합된 페녹사진을 포함하는 비교화합물 B를 호스트 재료로 사용한 경우 소자의 결과가 더 우수하였고, 비교화합물 B에 벤젠고리 또는 피리딘이나 피리미딘 고리가 하나 이상 더 축합되거나 인돌이 축합된 페녹씨아진을 메인 골격으로 가지는 본 발명의 화합물을 호스트 재료로 사용할 경우 소자의 결과가 가장 우수하였다.In more detail, the comparative compound B, which is a CBP used as a host material, and the comparative compound B containing phenoxylated indole-condensed in its main skeleton were used as a host material, When the compound of the present invention having a benzene ring or a phenocyazine in which at least one of pyridine and pyrimidine rings are condensed or indole-condensed is used as a host material, the result of the device is the most excellent.
본 발명의 화합물의 경우, 비교화합물 B의 메인 골격에 벤젠고리가 하나 이상 축합되면서 HOMO 레벨이 낮아지게 되는데, 이로 인해 정공의 수송 측면 및 열적 안정성과 같은 물성 측면에서 유리한 점을 가지게 된다. 이러한 장점은 소자 제작시 화합물을 증착하는 과정에서 소자 성능 향상에 주요한 역할을 하게 되므로 소자의 성능이 향상되는 것으로 보인다.In the case of the compound of the present invention, the HOMO level is lowered by condensing at least one benzene ring on the main skeleton of the comparative compound B, which is advantageous in terms of physical properties such as transporting side of holes and thermal stability. These advantages are expected to improve the performance of the device because it plays a major role in improving the performance of the device during the deposition of the compound during the fabrication of the device.
이상의 설명은 본 발명을 예시적으로 설명한 것에 불과한 것으로, 본 발명에 속하는 기술분야에서 통상의 지식을 가지는 자라면 본 발명의 본질적인 특성에서 벗어나지 않는 범위에서 다양한 변형이 가능할 것이다. 따라서, 본 명세서에 개시된 실시예들은 본 발명을 한정하기 위한 것이 아니라 설명하기 위한 것이고, 이러한 실시예에 의하여 본 발명의 사상과 범위가 한정되는 것은 아니다. 본 발명의 보호범위는 아래의 청구범위에 의하여 해석되어야 하며, 그와 동등한 범위 내의 모든 기술은 본 발명의 권리범위에 포함하는 것으로 해석되어야 할 것이다.The foregoing description is merely illustrative of the present invention, and various modifications may be made without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed herein are intended to be illustrative rather than limiting, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be construed according to the following claims, and all the techniques within the scope of the claims should be construed as being included in the scope of the present invention.
100: 유기전기소자
110: 기판
120: 제 1전극
130: 정공주입층
140: 정공수송층
141: 버퍼층
150: 발광층
151: 발광보조층
160: 전자수송층
170: 전자주입층
180: 제 2전극100: organic electric element 110: substrate
120: first electrode 130: hole injection layer
140: Hole transport layer 141: Buffer layer
150: light emitting layer 151: light emitting auxiliary layer
160: electron transport layer 170: electron injection layer
180: second electrode
Claims (11)
<화학식 1>
상기 화학식 1에서,
A환, B환 및 C환은 서로 독립적으로 C6~C24의 방향족고리; 또는 O, N, S, Si, P 중 적어도 하나의 헤테로원자를 포함하는 C2~C20의 헤테로고리이며, 단, A환, B환 및 C환 중 적어도 하나는 C10~C24의 방향족고리이거나, 또는 O, N, S, Si, P 중 적어도 하나의 헤테로원자를 포함하는 C8~C20의 헤테로고리이며,
A환, B환 및 C환 중 적어도 하나에 하기 화학식 1-1이 결합되며,
<화학식 1-1>
R1 내지 R4는 서로 독립적으로 수소; 중수소; 할로겐; 시아노기; 니트로기; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-N(Ra)(Rb)로 이루어진 군에서 선택되며, 이웃한 R4끼리 서로 결합하여 고리를 형성할 수 있고, 이때 고리는 C6~C60의 방향족고리; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; 및 이들의 조합에서 선택되며,
l, m 및 n은 각각 0~6의 정수이며, 이들 각각이 2 이상의 정수인 경우, 각각의 R1, 각각의 R2, 각각의 R3, 각각의 R4는 서로 동일하거나 상이하며,
o는 0~4의 정수이고, o가 2 이상의 정수인 경우, 각각의 R4은 서로 동일하거나 상이하며,
X1는 O 또는 S이고,
X2 및 X3은 서로 독립적으로 단일결합, N(-L1-Ar1), O, S 또는 C(R')(R'')이고, X2 및 X3 중 적어도 하나는 단일결합이 아니며,
상기 L1은 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; C3~C60의 지방족고리기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 이들의 조합으로 이루어진 군에서 선택되며,
상기 Ar1은 C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-N(Ra)(Rb);로 이루어진 군에서 선택되며,
상기 R' 및 R"은 수소; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C1~C50의 알킬기; 및 -L'-N(Ra)(Rb)로 이루어진 군에서 선택되고, R', R"은 서로 결합하여 고리를 형성할 수 있으며,
상기 L'은 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; C3~C60의 지방족고리기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 이들의 조합으로 이루어진 군에서 선택되며,
상기 Ra 및 Rb는 서로 독립적으로 C6~C60의 아릴기; 플루오렌일기; C3~C60의 지방족고리기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 이들의 조합으로 이루어진 군에서 선택되며,
상기 R1 내지 R4, Ar1, L1, R', R", L', Ra, Rb, 및 이웃한 R4끼리 서로 결합하여 형성한 고리는 각각 중수소; 할로겐; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 실란기; 실록산기; 붕소기; 게르마늄기; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕실기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 중수소로 치환된 C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 시클로알킬기; C7-C20의 아릴알킬기; C8-C20의 아릴알켄일기; 및 이들의 조합으로 이루어진 군에서 선택된 하나 이상의 치환기로 더 치환될 수 있다.A compound represented by the following formula (1):
≪ Formula 1 >
In Formula 1,
A ring, B ring and C ring are independently of each other a C 6 -C 24 aromatic ring; Or a C 2 to C 20 heterocyclic ring containing at least one hetero atom selected from the group consisting of O, N, S, Si and P, provided that at least one of the A ring, the B ring and the C ring is a C 10 -C 24 aromatic a ring, or is O, a heterocyclic N, S, Si, C ~ 8, comprising at least one hetero atom in the P C 20,
(1) is bonded to at least one of A ring, B ring and C ring,
≪ Formula 1-1 >
R 1 to R 4 independently of one another are hydrogen; heavy hydrogen; halogen; Cyano; A nitro group; A C 6 to C 60 aryl group; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 to C 60 aliphatic cyclic group; A fused ring group of an aliphatic ring of C 3 to C 60 and an aromatic ring of C 6 to C 60 ; A C 1 to C 50 alkyl group; An alkenyl group having 2 to 20 carbon atoms; An alkynyl group having 2 to 20 carbon atoms; A C 1 to C 30 alkoxyl group; An aryloxy group of C 6 to C 30 ; And -L'-N (R a) is selected from the group consisting of (R b), and between the adjacent R 4 can bond to one another to form a ring, wherein the ring is an aromatic ring of C 6 ~ C 60; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 to C 60 aliphatic cyclic group; And combinations thereof,
each of R 1 , R 2 , R 3 , and R 4 is the same or different from each other, and each of R 1 , R 2 , R 3 , and R 4 is the same or different from each other,
o is an integer of 0 to 4, and when o is an integer of 2 or more, each R 4 is the same as or different from each other,
X < 1 > is O or S,
X 2 and X 3 are independently a single bond, N (-L 1 -Ar 1 ), O, S or C (R ') (R ") and at least one of X 2 and X 3 is a single bond No,
L < 1 > is a single bond; An arylene group having 6 to 60 carbon atoms; A fluorenylene group; A C 3 to C 60 aliphatic cyclic group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; And combinations thereof,
Ar 1 is a C 6 to C 60 aryl group; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 to C 60 aliphatic cyclic group; A fused ring group of an aliphatic ring of C 3 to C 60 and an aromatic ring of C 6 to C 60 ; A C 1 to C 50 alkyl group; An alkenyl group having 2 to 20 carbon atoms; An alkynyl group having 2 to 20 carbon atoms; A C 1 to C 30 alkoxyl group; An aryloxy group of C 6 to C 30 ; And -L'-N (R a ) (R b );
Wherein R 'and R "is hydrogen; C 6 ~ C aryl group of 60; fluorene group; O, N, S, a heterocyclic of C 2 ~ containing at least one hetero atom of Si and P C 60 group; alkyl group of C 1 ~ C 50; is selected from the group consisting of and -L'-N (R a) ( R b), R ', R " may bond to one another to form a ring,
L 'is a single bond; An arylene group having 6 to 60 carbon atoms; A fluorenylene group; A C 3 to C 60 aliphatic cyclic group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; And combinations thereof,
R a and R b are each independently a C 6 to C 60 aryl group; A fluorenyl group; A C 3 to C 60 aliphatic cyclic group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; And combinations thereof,
Wherein R 1 to R 4, Ar 1, L 1 , R ', R ", L', R a, R b, R 4 and the adjacent ring formed by binding to each other, are each heavy hydrogen; halogen; C 1 -C alkyl group or a C 6 aryl group a substituted or unsubstituted silane group of 20 -C 20; siloxane group; a boron group; germanium group; cyano group; nitro group; an alkylthio import of C 1 -C 20; C 1 -C 20 of an alkoxyl group; an alkyl group of C 1 -C 20; an aryl of C 6 -C 20 substituted with heavy hydrogen; C 2 -C 20 alkynyl of;; C 6 aryl group of C 2 -C 20 alkenyl group 20 -C of A C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C 3 -C 20 cycloalkyl group, a C 7 -C 20 heterocyclic group, aryl alkene of C 8 -C 20 group;; C 20 arylalkyl groups and with one or more substituents selected from the group consisting of may be further substituted.
상기 화학식 1은 하기 화학식 2 내지 화학식 7 중에서 하나로 표시되는 것을 특징으로 하는 화합물:
<화학식 2> <화학식 3> <화학식 4>
<화학식 5> <화학식 6> <화학식 7>
상기 화학식 2 내지 화학식 7에서,
R1 내지 R3, l, m, n은 제1항에서 정의된 것과 같고,
A환, B환 및 C환은 C10~C24의 아릴기이거나, 또는 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C8~C24의 헤테로고리기이며,
V1 내지 V11은 CH, CR 또는 N이며, 여기서 R은 서로 독립적으로 수소; 중수소; 할로겐; 시아노기; 니트로기; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-N(Ra)(Rb)로 이루어진 군에서 선택되며, L', Ra 및 Rb는 제1항에서 정의된 것과 같다.The method according to claim 1,
(1) is represented by one of the following formulas (2) to (7):
≪ Formula 2 >< EMI ID =
≪ Formula 5 >< EMI ID =
In the above Chemical Formulas 2 to 7,
R 1 to R 3 , l, m and n are the same as defined in claim 1,
A ring, B ring and C ring are C 10 -C 24 aryl groups or C 8 -C 24 heterocyclic groups containing at least one hetero atom selected from O, N, S, Si and P,
V 1 to V 11 are CH, CR, or N, wherein R is independently from each other hydrogen; heavy hydrogen; halogen; Cyano; A nitro group; A C 6 to C 60 aryl group; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 to C 60 aliphatic cyclic group; A fused ring group of an aliphatic ring of C 3 to C 60 and an aromatic ring of C 6 to C 60 ; A C 1 to C 50 alkyl group; An alkenyl group having 2 to 20 carbon atoms; An alkynyl group having 2 to 20 carbon atoms; A C 1 to C 30 alkoxyl group; An aryloxy group of C 6 to C 30 ; And -L'-N (R a ) (R b ), wherein L ', R a and R b are as defined in claim 1.
A환, B환 및 C환은 하기 화학식 B-1 내지 화학식 B-7로 이루어진 군에서 선택되는 것을 특징으로 하는 화합물:
상기 화학식 B-1 내지 화학식 B-7에 있어서,
"*"표시는 축합되는 위치를 나타내며,
Z4 내지 Z50은 CR0 또는 N이며, 여기서 R0는 수소; 중수소; 할로겐; 시아노기; 니트로기; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; C3~C60의 지방족고리와 C6~C60의 방향족고리의 융합고리기; C1~C50의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L'-N(Ra)(Rb)로 이루어진 군에서 선택되고, L', Ra 및 Rb는 제1항에서 정의된 것과 같다.The method according to claim 1,
A ring, B ring and C ring are selected from the group consisting of the following formulas B-1 to B-7:
In the formulas (B-1) to (B-7)
The symbol "*" indicates the position to be condensed,
Z 4 to Z 50 are CR 0 or N, wherein R 0 is hydrogen; heavy hydrogen; halogen; Cyano; A nitro group; A C 6 to C 60 aryl group; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A C 3 to C 60 aliphatic cyclic group; A fused ring group of an aliphatic ring of C 3 to C 60 and an aromatic ring of C 6 to C 60 ; A C 1 to C 50 alkyl group; An alkenyl group having 2 to 20 carbon atoms; An alkynyl group having 2 to 20 carbon atoms; A C 1 to C 30 alkoxyl group; An aryloxy group of C 6 to C 30 ; And -L'-N (R a ) (R b ), and L ', R a and R b are as defined in claim 1.
상기 화학식 1은 하기 화학식 8 내지 화학식 16 중에서 하나로 표시되는 것을 특징으로 하는 화합물:
<화학식 8> <화학식 9> <화학식 10>
<화학식 11> <화학식 12> <화학식 13>
<화학식 14> <화학식 15> <화학식 16>
상기 화학식 8 내지 화학식 16에서,
A환, B환, C환, R1 내지 R4, X1 내지 X3, l, m, n, o는 제1항에서 정의된 것과 같고, l'은 0~1의 정수, l"은 0~3의 정수, m'은 0~2의 정수이다.The method according to claim 1,
The compound of formula (I) is represented by one of the following formulas (8) to (16):
≪ Formula 8 >< EMI ID =
≪ Formula 11 >< EMI ID =
≪ Formula 14 >< EMI ID =
In the above Chemical Formulas 8 to 16,
A ring, B ring, C ring, R 1 to R 4, X 1 to X 3, l, m, n , o are the same as defined in claim 1, l 'is an integer of 0 ~ 1, l "is An integer of 0 to 3, and m 'is an integer of 0 to 2.
상기 화학식 1로 표시되는 화합물은 하기 화합물 중 하나인 것을 특징으로 하는 화합물:
Wherein the compound represented by Formula 1 is one of the following compounds:
상기 유기물층은 제1항의 화학식 1로 표시되는 단독 화합물 또는 2종 이상의 화합물을 포함하는 것을 특징으로 하는 유기전기소자.An organic electroluminescent device comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode,
Wherein the organic material layer comprises a single compound represented by the general formula (1) of claim 1 or two or more compounds.
상기 유기물층은 정공주입층, 정공 수송층, 발광보조층, 발광층, 전자수송보조층, 전자 수송층 및 전자 주입층 중 적어도 하나의 층을 포함하는 것을 특징으로 하는 유기전기소자.The method according to claim 6,
Wherein the organic material layer includes at least one of a hole injection layer, a hole transporting layer, a light emitting auxiliary layer, a light emitting layer, an electron transporting auxiliary layer, an electron transporting layer, and an electron injecting layer.
상기 화합물은 상기 발광층에 포함된 것을 특징으로 하는 유기전기소자.8. The method of claim 7,
Wherein the compound is included in the light emitting layer.
상기 유기물층은 스핀코팅 공정, 노즐 프린팅 공정, 잉크젯 프린팅 공정, 슬롯코팅 공정, 딥코팅 공정 또는 롤투롤 공정에 의해 형성되는 것을 특징으로 하는 유기전계소자.The method according to claim 6,
Wherein the organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process.
상기 디스플레이장치를 구동하는 제어부;를 포함하는 전자장치.A display device including the organic electroluminescent device of claim 6; And
And a control unit for driving the display device.
상기 유기전기소자는 유기전기발광소자, 유기태양전지, 유기감광체, 유기트랜지스터, 단색 조명용 소자 및 퀀텀닷 디스플레이용 소자로 이루어진 군에서 선택되는 것을 특징으로 하는 전자장치.11. The method of claim 10,
Wherein the organic electroluminescent device is selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, a monochromatic illumination device, and a quantum dot display device.
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| KR20140064612A (en) * | 2012-11-20 | 2014-05-28 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
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| KR20170126811A (en) * | 2016-05-10 | 2017-11-20 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting device comprising the same |
| KR20170139350A (en) * | 2016-06-09 | 2017-12-19 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting device comprising the same |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200112091A (en) * | 2019-03-20 | 2020-10-05 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| CN113024560A (en) * | 2019-12-09 | 2021-06-25 | 北京鼎材科技有限公司 | Organic electroluminescent material and device |
| KR20210106733A (en) * | 2020-02-21 | 2021-08-31 | 성균관대학교산학협력단 | Organic light-emitting material and organic electroluminescence device having the organic light-emitting material |
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| KR102469688B1 (en) | 2022-11-23 |
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