TW202110846A - Organic compound for capping layer and organic electroluminescent device including the same - Google Patents
Organic compound for capping layer and organic electroluminescent device including the same Download PDFInfo
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- TW202110846A TW202110846A TW109117304A TW109117304A TW202110846A TW 202110846 A TW202110846 A TW 202110846A TW 109117304 A TW109117304 A TW 109117304A TW 109117304 A TW109117304 A TW 109117304A TW 202110846 A TW202110846 A TW 202110846A
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- 150000002894 organic compounds Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 93
- 239000010410 layer Substances 0.000 claims description 163
- 239000000126 substance Substances 0.000 claims description 58
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 239000011247 coating layer Substances 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 239000012044 organic layer Substances 0.000 claims description 20
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 125000005561 phenanthryl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims 1
- 125000005493 quinolyl group Chemical group 0.000 claims 1
- 238000002347 injection Methods 0.000 description 38
- 239000007924 injection Substances 0.000 description 38
- 230000015572 biosynthetic process Effects 0.000 description 28
- 238000000034 method Methods 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 25
- 239000000463 material Substances 0.000 description 24
- 230000005525 hole transport Effects 0.000 description 22
- 238000010521 absorption reaction Methods 0.000 description 19
- 239000000758 substrate Substances 0.000 description 13
- 238000001771 vacuum deposition Methods 0.000 description 12
- 239000010408 film Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- -1 benzofluorenyl Chemical group 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- 230000008021 deposition Effects 0.000 description 7
- 238000004528 spin coating Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 238000005266 casting Methods 0.000 description 4
- 229920000609 methyl cellulose Polymers 0.000 description 4
- 239000001923 methylcellulose Substances 0.000 description 4
- 235000010981 methylcellulose Nutrition 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 3
- 230000005281 excited state Effects 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 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
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 150000002987 phenanthrenes Chemical group 0.000 description 2
- 150000005041 phenanthrolines Chemical class 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000012780 transparent material Substances 0.000 description 2
- 125000005580 triphenylene group Chemical group 0.000 description 2
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- ZOVCCWLRACPTOO-UHFFFAOYSA-N 2-bromotriphenylene Chemical compound BrC1=CC=2C3=CC=CC=C3C3=CC=CC=C3C2C=C1.BrC1=CC=2C3=CC=CC=C3C3=CC=CC=C3C2C=C1 ZOVCCWLRACPTOO-UHFFFAOYSA-N 0.000 description 1
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- QGFYFOHMBDMGBZ-UHFFFAOYSA-N 5-[(7-chloroquinolin-4-yl)amino]-2-(diethylaminomethyl)phenol Chemical compound C1=C(O)C(CN(CC)CC)=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 QGFYFOHMBDMGBZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RAASUWZPTOJQAY-UHFFFAOYSA-N Dibenz[a,c]anthracene Chemical group C1=CC=C2C3=CC4=CC=CC=C4C=C3C3=CC=CC=C3C2=C1 RAASUWZPTOJQAY-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004982 aromatic amines Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 238000000572 ellipsometry Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229920002457 flexible plastic Polymers 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- UPYVSYVLGOADDG-UHFFFAOYSA-N phenanthren-3-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3C=CC2=C1 UPYVSYVLGOADDG-UHFFFAOYSA-N 0.000 description 1
- JCDAUYWOHOLVMH-UHFFFAOYSA-N phenanthren-9-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC3=CC=CC=C3C2=C1 JCDAUYWOHOLVMH-UHFFFAOYSA-N 0.000 description 1
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
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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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- 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
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
-
- 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
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/844—Encapsulations
-
- 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
- H10K50/80—Constructional details
- H10K50/85—Arrangements for extracting light from the devices
- H10K50/858—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
本發明係有關於覆蓋層用有機化合物及包含其的有機發光裝置。The present invention relates to an organic compound for a cover layer and an organic light-emitting device containing the organic compound.
在有機發光裝置中,用作有機物層的材料可根據功能大致分類為發光材料、電洞注入材料、電洞輸送材料、電子輸送材料、電子注入材料等。並且,上述發光材料可根據發光機理分類為來源於電子的單態激發狀態的螢光材料和來源於電子的三重態激發狀態的磷光材料。進而,可根據發光色分類為藍色、綠色、紅色發光材料。In organic light-emitting devices, materials used as the organic layer can be roughly classified into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like according to their functions. In addition, the above-mentioned light-emitting materials can be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to the light-emitting mechanism. Furthermore, it can be classified into blue, green, and red light-emitting materials according to the light-emitting color.
一般的有機發光裝置可具有如下結構,在基板上部形成陽極,在該陽極上部依次形成電洞輸送層、發光層、電子輸送層及陰極。其中,上述電洞輸送層、發光層及電子輸送層為由有機化合物形成的有機薄膜。A general organic light-emitting device may have a structure in which an anode is formed on the upper part of a substrate, and a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode are sequentially formed on the upper part of the anode. Among them, the hole transport layer, the light emitting layer, and the electron transport layer are organic thin films formed of organic compounds.
具有如上所述的結構的有機發光裝置的驅動原理如下。若向上述陽極及陰極之間施加電壓,則從陽極注入的電洞經由電洞輸送層而移動至發光層的同時從陰極注入的電子經由電子輸送層而移動至發光層。移動至發光層的上述電洞及電子再結合而生成激子(exciton)。上述激子從激發狀態轉換為基態而生成光。The driving principle of the organic light emitting device having the structure as described above is as follows. When a voltage is applied between the anode and the cathode, the holes injected from the anode move to the light emitting layer via the hole transport layer, and the electrons injected from the cathode move to the light emitting layer via the electron transport layer. The above-mentioned holes and electrons that have moved to the light-emitting layer recombine to generate excitons. The above-mentioned excitons convert from an excited state to a ground state to generate light.
有機發光裝置的效率通常可分為內部發光效率和外部發光效率。上述內部發光效率與如電洞輸送層、發光層及電子輸送層等一樣介入第一電極與第二電極之間的有機層中如何有效地生成激子而實現光轉換相關,按理論上來講,就內部發光效率而言,螢光為約25%,磷光為約100%。The efficiency of organic light-emitting devices can generally be divided into internal luminous efficiency and external luminous efficiency. The above-mentioned internal luminous efficiency is related to how to effectively generate excitons in the organic layer between the first electrode and the second electrode, such as the hole transport layer, the light emitting layer, and the electron transport layer, to achieve light conversion. In theory, In terms of internal luminous efficiency, fluorescence is about 25%, and phosphorescence is about 100%.
另一方面,外部發光效率呈現從上述有機物層生成的光提取到有機發光裝置外部的效率,通常,內部發光效率的約20%的水準提取到外部。On the other hand, the external luminous efficiency represents the efficiency of extracting the light generated from the organic material layer to the outside of the organic light-emitting device, and generally, about 20% of the internal luminous efficiency is extracted to the outside.
用於提高這種外部發光效率,即光提取效率的方法,為了防止發射到外部的光進行全反射而被損失,將多種有機化合物適用為覆蓋層(capping layer),為了改善有機發光裝置的性能,持續努力開發具有可提高外部發光效率的高折射率及薄膜穩定性的有機化合物。The method for improving the external luminous efficiency, that is, the light extraction efficiency, in order to prevent the light emitted to the outside from being totally reflected and lost, a variety of organic compounds are applied as a capping layer, in order to improve the performance of the organic light-emitting device Continuing efforts to develop organic compounds with high refractive index and film stability that can improve external luminous efficiency.
習知技術文獻 專利文獻 韓國公開專利公報第10-2004-0098238號Known technical literature Patent literature Korean Patent Publication No. 10-2004-0098238
發明要解決的技術問題The technical problem to be solved by the invention
本發明要解決的問題在於,提供維持高折射率的同時放大紫外線區域的吸收強度及範圍,增大外部量子效率,並可改善因暴露於外部紫外線而引起的壽命縮短問題的覆蓋層用化合物及包括含有上述化合物的覆蓋層的有機發光裝置。The problem to be solved by the present invention is to provide a compound for a coating layer and a coating layer that amplifies the absorption intensity and range of the ultraviolet region while maintaining a high refractive index, increases the external quantum efficiency, and can improve the problem of shortened lifetime caused by exposure to external ultraviolet rays. An organic light-emitting device including a cover layer containing the above-mentioned compound.
本發明要解決的問題在於,提供使可見光區域吸收最小化,維持寬的帶隙,可實現高色純度的覆蓋層用化合物及包括含有上述化合物的覆蓋層的有機發光裝置。The problem to be solved by the present invention is to provide a compound for a cover layer that minimizes absorption in the visible light region, maintains a wide band gap, and can achieve high color purity, and an organic light-emitting device including a cover layer containing the compound.
本發明要解決的又一問題在於,提供藉由板狀的稠芳基或稠雜芳基來適當調節化合物內龐大特性,從而改善分子間的薄膜排列,以改善折射率,並可從外部空氣及水分中改善穩定性的覆蓋層用化合物及包括含有上述化合物的覆蓋層的有機發光裝置。Another problem to be solved by the present invention is to provide a plate-shaped dense aryl group or a dense heteroaryl group to properly adjust the bulky characteristics of the compound, thereby improving the film arrangement between molecules, improving the refractive index, and allowing the air to be removed from the outside. And a compound for a coating layer that improves stability in moisture, and an organic light-emitting device including a coating layer containing the above-mentioned compound.
本發明要解決的另一問題在於,提供具有高的Tg及高的Td,以防止分子間再結晶化,從而可從有機發光裝置驅動時產生的熱中維持穩定的薄膜的覆蓋層用化合物及包括含有上述化合物的覆蓋層的有機發光裝置。Another problem to be solved by the present invention is to provide a compound for a coating layer that has a high Tg and a high Td to prevent intermolecular recrystallization, thereby maintaining a stable thin film from the heat generated when the organic light-emitting device is driven. An organic light-emitting device containing a coating layer of the above-mentioned compound.
但是,本發明要解決的問題不局限於以上描述的問題,本發明所屬技術領域具有通常知識者應當藉由以下的記載內容明確理解未描述的其他問題。However, the problems to be solved by the present invention are not limited to the problems described above. Those with ordinary knowledge in the technical field to which the present invention belongs should clearly understand other problems not described by the following description.
本發明的技術方案在於:The technical scheme of the present invention is:
本發明的第一實施方式提供由以下化學式1表示的覆蓋層用化合物。The first embodiment of the present invention provides a compound for a cover layer represented by the following Chemical Formula 1.
化學式1
在上述化學式1中,
A、B及C各自獨立地為取代或未取代的C6~C50的芳基、或者由取代或未取代的六元環形成的C2~C50的雜芳基,
上述A、B及C中的一個以上為由取代或未取代的六元環形成的三環以上的稠芳基或者由取代或未取代的六元環形成的三環以上的稠雜芳基(但,蒽基除外),
L1
至L3
各自獨立地為直接鍵合、取代或未取代的C6~C50的伸芳基、或者取代或未取代的C2~C50的雜芳基。
本發明的第二實施方式提供有機發光裝置,其包括:第一電極及第二電極;有機物層,介於上述第一電極及上述第二電極內側;以及覆蓋層,配置於上述第一電極及上述第二電極中的一個以上電極外側,並包含本發明第一實施方式的覆蓋層用化合物。The second embodiment of the present invention provides an organic light-emitting device, which includes: a first electrode and a second electrode; an organic layer interposed between the first electrode and the second electrode; and a cover layer disposed on the first electrode and the second electrode. One or more of the above-mentioned second electrodes are outside and contain the compound for a cover layer according to the first embodiment of the present invention.
對照先前技術之功效Compare the effects of previous technologies
本發明的一實例的覆蓋層用化合物呈現如下作用效果,維持高折射率的同時放大紫外線區域的吸收強度及範圍,增大外部量子效率,並可改善因暴露於外部紫外線而引起的壽命縮短問題。The compound for the coating layer of an example of the present invention exhibits the following effects, while maintaining a high refractive index, amplifying the absorption intensity and range of the ultraviolet region, increasing the external quantum efficiency, and improving the problem of shortened life due to exposure to external ultraviolet rays .
並且,本發明的一實例的覆蓋層用化合物呈現如下作用效果,使可見光區域吸收最小化,維持寬的帶隙,可實現高色純度。In addition, the compound for a cover layer of an example of the present invention exhibits the following effects to minimize absorption in the visible light region, maintain a wide band gap, and achieve high color purity.
進而,本發明的一實例的覆蓋層用化合物呈現如下作用效果,藉由板狀的稠芳基或稠雜芳基來適當調節化合物內龐大特性,從而改善分子間的薄膜排列,以改善折射率,並可從外部空氣及水分中改善穩定性。Furthermore, the compound for the covering layer of an example of the present invention exhibits the following effects. The bulky properties of the compound are appropriately adjusted by the plate-shaped dense aryl group or the dense heteroaryl group, thereby improving the film arrangement between molecules and improving the refractive index. , And can improve stability from outside air and moisture.
進而,本發明一實例的覆蓋層用化合物呈現具有高的Tg及高的Td,以防止分子間再結晶化,從而可從有機發光裝置驅動時產生的熱中維持穩定的薄膜的作用效果。Furthermore, the compound for a cover layer of an example of the present invention exhibits a high Tg and a high Td to prevent intermolecular recrystallization, thereby maintaining a stable film effect from the heat generated when the organic light-emitting device is driven.
以下,參照圖式,詳細說明本發明的實例及實施例,使得本發明所屬技術領域具有通常知識者可容易實施。Hereinafter, examples and embodiments of the present invention will be described in detail with reference to the drawings, so that those with ordinary knowledge in the technical field to which the present invention belongs can be easily implemented.
但是,本發明能夠以多種不同的形態實現,且不局限於在此說明的實例及實施例。並且,在圖中,為了明確說明本發明,省略了與說明無關的部分,在說明書全文中,對於類似的部分,標注了類似的元件符號。However, the present invention can be implemented in many different forms, and is not limited to the examples and embodiments described here. In addition, in the drawings, in order to clearly explain the present invention, parts that are not related to the description are omitted. In the entire specification, similar parts are marked with similar reference numerals.
在本發明說明書全文中,當一個部件位於另一部件“上”時,不僅包括一個部件與另一部件相接觸的情況,還包括在兩個部件之間存在其他部件的情況。Throughout the specification of the present invention, when a component is "on" another component, it includes not only the case where one component is in contact with another component, but also the case where there are other components between the two components.
在本發明說明書全文中,當一個部分“包括”一個結構要素時,除非有特別相反的記載,則意味著還可包括其他結構要素,而不是排除其他結構要素。在本發明說明書全文中使用的術語“約”、“實質上”等在所提及的含義上提示固有的製備及物質容差時以其數值或接近於其數值的含義使用,以防止昧良心的侵權人不當地利用為了幫助理解本發明而提及準確或絕對的數值的公開內容。在本發明說明書全文中使用的術語“~(的)步驟”或“~的步驟”不意味著“用於~的步驟”。In the entire specification of the present invention, when a part "includes" a structural element, unless there is a special description to the contrary, it means that other structural elements may be included instead of excluding other structural elements. The terms "about", "substantially", etc. used throughout the specification of the present invention are used in the meaning of their value or close to their value when the mentioned meanings indicate inherent preparation and material tolerances to prevent ambiguity. The infringer improperly uses the disclosure that mentions accurate or absolute values in order to help understand the present invention. The term "~ (of) step" or "~ step" used throughout the specification of the present invention does not mean "a step for ~".
在本發明說明書全文中,馬庫西(Markush)形式的表現中所含的“它們的組合”這一術語意味著選自由馬庫西形式的表現中所記載的多個結構要素組成的群組中的一種以上的混合或組合,意味著包括選自由上述多個結構要素組成的群組中的一種以上。Throughout the specification of the present invention, the term "their combination" contained in the expression of the Markush form means to be selected from the group consisting of a plurality of structural elements described in the expression of the Markush form A mixture or combination of more than one of the above means to include more than one selected from the group consisting of the above-mentioned multiple structural elements.
在本發明說明書全文中,“A和/或B”這一記載意味著“A或B,或者A及B”。In the entire specification of the present invention, the description of "A and/or B" means "A or B, or A and B".
在本發明說明書全文中,術語“芳基”或“伸芳基”可意味著包含C6-50的芳香族烴環基,例如,苯基、苄基、萘基、聯苯基、三聯苯基、芴基、菲基、三苯基烯基、苯基烯基、䓛基、熒蒽基、苯並芴基、苯並三苯基烯基、苯並䓛基、蒽基、均二苯乙烯基、芘基等的芳香族環,“雜芳基”或“伸雜芳基”作為包含一個以上雜原子的C2-50的芳香族環,例如,意味著包含從吡咯啉基、吡嗪基、吡啶基、吲哚基、異吲哚基、呋喃基、苯並呋喃基、異苯並呋喃基、二苯並呋喃基、苯並噻吩基、二苯並噻吩基、喹啉基、異喹啉基、喹㗁啉基、哢唑基、菲基唳基、吖啶基、菲基咯啉基、噻吩基及由吡啶環、吡嗪環、嘧啶環、噠嗪環、三嗪環、吲哚環、喹啉環、吖啶環、吡咯烷環、二噁烷環、呱啶環、嗎啉環、呱嗪環、哢唑環、呋喃環、噻吩環、噁唑環、噁二唑環、苯並噁唑環、噻唑環、噻重氮環、苯並噻唑環、三唑環、咪唑環、苯並咪唑環、吡喃環、二苯並呋喃環形成的雜環基。Throughout the specification of the present invention, the term "aryl" or "arylene" may mean a C6-50 aromatic hydrocarbon ring group, for example, phenyl, benzyl, naphthyl, biphenyl, terphenyl , Fluorenyl, phenanthryl, triphenylalkenyl, phenylalkenyl, phenylalkenyl, fluoranthene, benzofluorenyl, benzotriphenylalkenyl, benzotriphenylene, anthracenyl, stilbene Aromatic rings such as pyrenyl, pyrenyl, etc., "heteroaryl" or "heteroaryl" as a C2-50 aromatic ring containing one or more heteroatoms, for example, means to include pyrrolinyl, pyrazinyl , Pyridyl, indolyl, isoindolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, quinolinyl, isoquine Linyl, quinoline, azazolyl, phenanthryl, acridinyl, phenanthroline, thienyl, and pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indino Dole ring, quinoline ring, acridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, pyrazine ring, oxazole ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring , Benzoxazole ring, thiazole ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring, benzimidazole ring, pyran ring, dibenzofuran ring formed heterocyclic group.
在本發明說明書全文中,術語“取代的”或“可取代的”可意味著可由選自由重氫、鹵素、氨基、腈基、硝基或C1 ~ 30 的烷基、C2 ~ 30 的烯基、C1 ~ 30 的烷氧基、C3 ~ 20 的環烷基、C3 ~ 20 的雜環烷基、C1 ~ 30 硫醚基、C6 ~ 30 的芳基及C2 ~ 30 的雜芳基組成的群組中的一種以上的基取代未取代。並且,在本發明說明書全文中,相同的元件符號只要沒有特別提及的內容,就可具有相同意思。In the specification of the present invention, the term "substituted" or "substituted" means that may be selected from the group consisting of heavy hydrogen, halogen, amino, nitrile, nitro or C 1 ~ 30 alkyl group, C 2 ~ 30 of alkenyl group, C 1 ~ 30 alkoxy group, C 3 ~ 20 cycloalkyl group, the heterocycloalkyl group of C 3 ~ 20, C 1-30 thioether, C aryl and C 6 ~ 30 ~ 2 One or more groups in the group consisting of 30 heteroaryl groups are substituted and unsubstituted. In addition, throughout the specification of the present invention, the same reference signs may have the same meaning as long as there is no specific mention.
本發明的第一實施方式提供由以下化學式1表示的覆蓋層用化合物。The first embodiment of the present invention provides a compound for a cover layer represented by the following Chemical Formula 1.
化學式1
在上述化學式1中,
A、B及C各自獨立地為取代或未取代的C6~C50的芳基、或者由取代或未取代的六元環形成的C2~C50的雜芳基,上述A、B及C中的一個以上為由取代或未取代的六元環形成的三環以上的稠芳基或者由取代或未取代的六元環形成的三環以上的稠雜芳基(但,蒽基除外),
L1
至L3
各自獨立地為直接鍵合、取代或未取代的C6~C50的伸芳基、或者取代或未取代的C2~C50的雜芳基。
在本發明中,上述取代基各自獨立地為氫、重氫、鹵素、硝基、腈基、取代或未取代的C1~C30的烷基、取代或未取代的C2~C30的烯基、取代或未取代的C1~C30的烷氧基、取代或未取代的C1~C30的硫醚基、取代或未取代的C6~C50的芳基、或者由取代或未取代的C2~C9的環結構形成的C2~C50的雜芳基。In the present invention, the above-mentioned substituents are each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted C2~C30 alkenyl, substituted Or unsubstituted C1~C30 alkoxy group, substituted or unsubstituted C1~C30 thioether group, substituted or unsubstituted C6~C50 aryl group, or substituted or unsubstituted C2~C9 ring structure The formed C2~C50 heteroaryl group.
本發明的一實例的上述化學式1的覆蓋層用化合物,藉由與由六元環形成的三環以上的稠芳基或由六環形成的三環以上的稠雜芳基結合的芳基胺,維持高折射率的同時可增大紫外線區域的吸收波長強度及範圍。藉由這種特性,本發明的覆蓋層用化合物可增大有機發光裝置的外部量子效率,並可從外部紫外線暴露中改善壽命。The compound for the coating layer of the above
並且,本發明的一實例的上述化學式1的覆蓋層用化合物包含由六元環形成的三環以上的稠芳基或由六元環形成的三環以上的稠雜芳基,由此使可見光區域的吸收最小化,可維持寬的帶隙,其結果可實現高色純度。In addition, the compound for the coating layer of the above-mentioned
並且,本發明的一實例的上述化學式1的覆蓋層用化合物,與由六元環形成的三環以上的稠芳基或由六元環形成的三環以上的稠雜芳基結合,由此分子間薄膜排列變得優秀。由此,可改善折射率,並可從外部空氣或水分中改善穩定性。In addition, the compound for the coating layer of the above
並且,本發明的一實例的上述化學式1的覆蓋層用化合物,在450nm的折射率可以為2.1以上,具體地可以為2.2以上。並且,在紫外線吸收區域380nm下的吸收強度為0.6以上,具體地可以為0.7以上。In addition, the compound for a coating layer of Chemical Formula 1 in an example of the present invention may have a refractive index at 450 nm of 2.1 or more, specifically 2.2 or more. In addition, the absorption intensity at 380 nm in the ultraviolet absorption region is 0.6 or more, and specifically may be 0.7 or more.
並且,本發明的一實例的上述化學式1的覆蓋層用化合物,藉由由六元環形成的三環以上的稠芳基或由六元環形成的三環以上的稠雜芳基,具有高的Tg及Td,其結果可防止分子間再結晶化,由此可從驅動有機發光裝置時產生的熱中維持穩定的薄膜。In addition, the compound for the coating layer of the above
即,將本發明的一實例的覆蓋層用化合物適用於覆蓋層,若將上述覆蓋層配置於有機發光裝置的電極外側,則可提高外部發光效率。當從介於有機發光裝置的第一電極及第二電極內側的有機物層中生成的光提取到有機發光裝置的外部時,可防止向外部發射的光被全反射而損失。That is, the compound for a cover layer of an example of the present invention is applied to the cover layer, and if the cover layer is arranged outside the electrode of the organic light-emitting device, the external luminous efficiency can be improved. When the light generated from the organic material layer inside the first electrode and the second electrode of the organic light emitting device is extracted to the outside of the organic light emitting device, the light emitted to the outside can be prevented from being totally reflected and lost.
本發明的一實例的覆蓋層用化合物,因如上的結構特徵,可具有高折射率,薄膜穩定性突出,當適用為有機發光裝置的覆蓋層時,可提高有機發光裝置的外部發光效率、色座標及壽命。The compound for a cover layer of an example of the present invention can have a high refractive index and outstanding film stability due to the above structural characteristics. When applied as a cover layer of an organic light-emitting device, it can improve the external luminous efficiency and color of the organic light-emitting device. Coordinates and life.
在本發明的一實例中,上述化學式1可由以下化學式2表示。In an example of the present invention, the above
化學式2
在上述化學式2中,
A、B及C各自獨立地如上述化學式1中所定義,
l、m及n各自獨立地為0或1至4的整數,
l+m+n為1以上的整數。Chemical formula 2 In the above chemical formula 2, A, B, and C are each independently as defined in the
由上述化學式2表示的化合物,包含與胺的氮直接鍵合的伸苯基,維持不能吸收可見光區域的寬的帶隙,並有效改善折射率。The compound represented by the above-mentioned chemical formula 2 contains phenylene directly bonded to the nitrogen of the amine, maintains a wide band gap in the region that cannot absorb visible light, and effectively improves the refractive index.
在本發明的一實例中,上述化學式1的化合物可由以下化學式3至化學式5中的一個表示。In an example of the present invention, the compound of the
化學式3 Chemical formula 3
化學式4 Chemical formula 4
化學式5
在上述化學式3至化學式5中,
A、B及C各自獨立地如上述化學式1中所定義,
o及p各自獨立地為0、1或2,
q為2至7的整數,
r為0或1至4的整數。Chemical formula 5 In the above chemical formulas 3 to 5, A, B and C are each independently as defined in the
如上所述,由上述化學式3至化學式5表示的化合物包含1,4-伸苯基,增大紫外線區域的吸收波長強度及範圍的同時可具有高折射率。As described above, the compounds represented by the above Chemical Formula 3 to Chemical Formula 5 include 1,4-phenylene, and can have a high refractive index while increasing the intensity and range of the absorption wavelength in the ultraviolet region.
根據本發明的一實例,在由六元環形成的三環以上的稠芳基中,上述六元環具體可指苯基,上述三環以上的稠芳基可指由三個以上環結構稠合的形態的芳基,形成上述稠芳基的環結構可指僅由六元環形成的結構。例如,由六元環形成的三環以上的稠芳基可以為菲、三亞苯、芘或䓛等。According to an example of the present invention, in a fused aryl group with three or more rings formed by a six-membered ring, the six-membered ring may specifically refer to a phenyl group, and the fused aryl group with three or more rings may refer to a fused aryl group with three or more The aryl group of the combined form, the ring structure forming the above-mentioned condensed aryl group may refer to a structure formed of only a six-membered ring. For example, the condensed aryl group with three or more rings formed by a six-membered ring may be phenanthrene, triphenylene, pyrene, or the like.
根據本發明的一實例,A、B及C中的一個以上可以為由取代或未取代的六元環形成的三環以上的稠芳基,具體可以為取代或未取代的菲基、或者取代或未取代的三苯基。According to an example of the present invention, one or more of A, B, and C may be a condensed aryl group with three or more rings formed by a substituted or unsubstituted six-membered ring, and specifically may be a substituted or unsubstituted phenanthrene group, or a substituted Or unsubstituted triphenyl.
並且,根據本發明的一實例,A、B及C中的兩個以上可各自獨立地為由取代或未取代的六元環形成的三環以上的稠芳基,具體可以為取代或未取代的菲基、或者取代或未取代的三苯基。Furthermore, according to an example of the present invention, two or more of A, B, and C may each independently be a three-ring or more condensed aryl group formed by a substituted or unsubstituted six-membered ring, and specifically may be substituted or unsubstituted Phenanthryl, or substituted or unsubstituted triphenyl.
並且,根據本發明的一實例,A、B及C中的兩個可以為取代或未取代的菲基、或者取代或未取代的三苯基,且剩餘一個可選自由苯基、聯苯基、三聯苯基、萘基或它們的組合組成的群組中。Furthermore, according to an example of the present invention, two of A, B, and C may be substituted or unsubstituted phenanthrene groups, or substituted or unsubstituted triphenyl groups, and the remaining one may be selected from a phenyl group or a biphenyl group. , Terphenyl, naphthyl, or a combination thereof.
根據本發明的一實例,A、B及C可各自獨立地選自由苯基、聯苯基、三聯苯基、萘基、吡啶基、喹啉基、菲基、三苯基或它們的組合組成的群組中。According to an example of the present invention, A, B, and C can each independently be selected from phenyl, biphenyl, terphenyl, naphthyl, pyridyl, quinolinyl, phenanthryl, triphenyl or a combination thereof In the group.
並且,根據本發明的一實例,上述化學式1的化合物可包含一個以上的甲基、甲氧基、氟基或腈基作為取代基。Also, according to an example of the present invention, the compound of the
並且,根據本發明的一實例,L1至L3可各自獨立地選自由苯基、聯苯基、三聯苯基、萘基及它們的組合組成的群組中。Also, according to an example of the present invention, L1 to L3 may each independently be selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, and combinations thereof.
在本發明的一實例中,由上述化學式1至化學式5表示的覆蓋層用化合物能夠以如下所述的反應式進行合成,不局限於此,還能夠以多種方法進行合成。In an example of the present invention, the compound for the coating layer represented by the above
反應式 Reaction formula
在本發明的一實例中,由上述化學式1表示的化合物可以為以下提出的化合物1至化合物576中的一種化合物,可不局限於此: 。In an example of the present invention, the compound represented by the
本發明的第二實施方式提供包括含有由上述化學式1至化學式5中的一種表示的化合物的覆蓋層的有機發光裝置。The second embodiment of the present invention provides an organic light-emitting device including a cover layer containing a compound represented by one of the above-mentioned
根據本發明的一實例,有機發光裝置可包括:第一電極及第二電極,有機物層,介於上述第一電極及上述第二電極內側;以及覆蓋層,配置於上述第一電極及上述第二電極中的一個以上的電極外側,並包含本發明的覆蓋層用化合物。其中,在第一電極或第二電極的兩側面中,將與介於第一電極與第二電極之間的有機物層相鄰的一側作為內側,將不與有機物層相鄰的一側作為外側。即,在第一電極的外側配置覆蓋層時,在覆蓋層與有機物層之間介入第一電極,在第二電極的外側配置覆蓋層時,在覆蓋層與有機物層之間介入第二電極。According to an example of the present invention, an organic light-emitting device may include: a first electrode and a second electrode, an organic layer interposed between the first electrode and the second electrode; and a cover layer disposed on the first electrode and the second electrode. The outer side of one or more of the two electrodes contains the compound for a coating layer of the present invention. Among them, of the two sides of the first electrode or the second electrode, the side adjacent to the organic layer between the first electrode and the second electrode is taken as the inner side, and the side not adjacent to the organic layer is taken as the inner side. Outside. That is, when the covering layer is arranged outside the first electrode, the first electrode is interposed between the covering layer and the organic layer, and when the covering layer is arranged outside the second electrode, the second electrode is interposed between the covering layer and the organic layer.
根據本發明的一實例,就上述有機發光裝置而言,在第一電極及第二電極內側可介入多種有機物層,在第一及第二電極中的至少一個外側可形成覆蓋層。上述覆蓋層均形成在第一電極的外側和第二電極外側,或者可配置於第一電極的外側或第二電極的外側。上述覆蓋層可包含本發明的覆蓋層用化合物。According to an example of the present invention, for the above-mentioned organic light-emitting device, a variety of organic layers can be inserted inside the first electrode and the second electrode, and a covering layer can be formed outside at least one of the first and second electrodes. The above-mentioned covering layers are both formed on the outside of the first electrode and the outside of the second electrode, or may be arranged on the outside of the first electrode or the outside of the second electrode. The above-mentioned covering layer may contain the compound for covering layer of the present invention.
並且,根據本發明的一實例,在介入有上述覆蓋層的第一電極及第二電極外側上還可形成起到多種功能的有機物層。即,覆蓋層可直接形成於第一電極(或第二電極)外側表面上,或者在第一電極(或第二電極)外側表面形成起到多種功能的有機物層,並在上述有機物層上可形成包含本發明的化合物的覆蓋層。In addition, according to an example of the present invention, an organic layer with multiple functions may be formed on the outer side of the first electrode and the second electrode interposed with the above-mentioned covering layer. That is, the covering layer may be directly formed on the outer surface of the first electrode (or second electrode), or an organic layer with multiple functions may be formed on the outer surface of the first electrode (or second electrode), and the organic layer may be formed on the organic layer. A covering layer containing the compound of the present invention is formed.
根據本發明的一實例,覆蓋層可單獨包含本發明的一實例的覆蓋層用化合物,或者可一起包含2種以上或習知的化合物。According to an example of the present invention, the cover layer may separately include the compound for the cover layer of an example of the present invention, or may include two or more or conventional compounds together.
本發明的一實例的有機發光裝置在第一電極及第二電極之間,即在第一電極及第二電極的內側包括1層以上的有機物層,在上述第一電極及第二電極的外側可形成覆蓋層。上述有機物層通常可以是構成發光部的電洞輸送層、發光層及電子輸送層,可不局限於此。The organic light-emitting device of an example of the present invention includes one or more organic layers between the first electrode and the second electrode, that is, on the inner side of the first electrode and the second electrode, and on the outer side of the first electrode and the second electrode. A cover layer can be formed. The above-mentioned organic substance layer may generally be a hole transport layer, a light emitting layer, and an electron transport layer constituting the light emitting part, but is not limited to these.
上述有機發光裝置在第一電極(陽極,anode)與第二電極(陰極,cathode)之間可包括1層以上的電洞注入層(HIL)、電洞輸送層(HTL)、發光層(EML)、電子輸送層(ETL)、電子注入層(EIL)等構成發光部的有機物層。The above organic light-emitting device may include more than one hole injection layer (HIL), hole transport layer (HTL), and light emitting layer (EML) between the first electrode (anode) and the second electrode (cathode). ), electron transport layer (ETL), electron injection layer (EIL) and other organic material layers that constitute the light-emitting part.
例如,上述有機發光裝置可根據第1圖中所記載的結構來製備而成。有機發光裝置可至下而上依次層疊第一電極(陽極,電洞注入電極1000)/電洞注入層200/電洞輸送層300/發光層400/電子輸送層500/電子注入層600/第二電極(陰極,電子注入電極2000)/覆蓋層3000。For example, the above-mentioned organic light-emitting device can be manufactured according to the structure described in Fig. 1. The organic light-emitting device can stack the first electrode (anode, hole injection electrode 1000)/hole injection layer 200/hole transport layer 300/
如上所述,本發明的一實例的覆蓋層用化合物,藉由與由六元環形成的三環以上的稠芳基或由六元環形成的三環以上的稠雜芳基結合的芳基胺,維持高折射率的同時增大紫外線區域的吸收波長強度及範圍,來增大有機發光裝置的外部量子效率,並可從外部紫外線暴露中改善壽命,由於包含由六元環形成的三環以上的稠芳基或由六元環形成的三環以上的稠雜芳基,因此可使可見光區域的吸收最小化並可維持寬的帶隙,其結果可實現高色純度,結合有由六元環形成的三環以上的稠芳基或由六元環形成的三環以上的稠雜芳基,分子間薄膜排列優秀,由此可改善折射率,可從外部空氣或水分中改善穩定性。並且,根據本發明的一實例的上述化學式1的覆蓋層用化合物,藉由由六元環形成的三環以上的稠芳基或由六元環形成的三環以上的稠雜芳基,具有高的Tg及Td,其結果可防止分子間再結晶化,由此可從驅動有機發光裝置時產生的熱中維持穩定的薄膜。即,將本發明的一實例的覆蓋層用化合物適用於覆蓋層,若將上述覆蓋層配置於有機發光裝置的電極外側,則可提高外部發光效率。當從介於有機發光裝置的第一電極及第二電極內側的有機物層中生成的光提取到有機發光裝置外部時,可防止向外部發射的光被全反射而損失。As described above, the compound for a coating layer of an example of the present invention has an aryl group bonded to a condensed aryl group with three or more rings formed by a six-membered ring or a condensed heteroaryl group with three or more rings formed by a six-membered ring. Amines maintain a high refractive index while increasing the absorption wavelength intensity and range of the ultraviolet region to increase the external quantum efficiency of the organic light-emitting device, and can improve the life of the organic light-emitting device from external ultraviolet exposure, because it contains a three-ring formed by a six-membered ring The above condensed aryl groups or condensed heteroaryl groups with three or more rings formed by six-membered rings can minimize the absorption in the visible light region and maintain a wide band gap. As a result, high color purity can be achieved. Condensed aryl groups with three or more rings formed by membered rings or condensed heteroaryl groups with more than three rings formed by six-membered rings, excellent intermolecular film alignment, which can improve refractive index, and improve stability from external air or moisture . In addition, the compound for the coating layer of the above-mentioned
在第1圖中,基板100可使用用於有機發光裝置的基板,尤其,可以為機械強度、熱穩定性、透明性、表面平滑性、處理容易性及防水性優秀的透明的玻璃基板或可彎曲的塑膠基板。In Figure 1, the substrate 100 can be a substrate for an organic light-emitting device. In particular, it can be a transparent glass substrate with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance. Curved plastic substrate.
第一電極1000用作用於注入有機發光裝置的電洞的陽極。為了可注入電洞,利用具有低的功函數的物質,可由氧化銦錫(ITO)、氧化銦鋅(IZO)、石墨烯(graphene)之類的透明的材質形成。The first electrode 1000 serves as an anode for injecting holes of the organic light-emitting device. In order to be able to inject holes, a material with a low work function is used, which can be formed of transparent materials such as indium tin oxide (ITO), indium zinc oxide (IZO), and graphene.
藉由真空沉積法、旋塗法、鑄造法、LB(Langmuir-Blodgett)法等來在上述第一電極上部沉積電洞注入層物質,由此可形成電洞注入層200。在藉由上述真空沉積法來形成電洞注入層的情況下,其沉積條件因用作電洞注入層200的材料的化合物、所需電洞注入層的結構及熱特性等而不同,但通常可在50-500℃的沉積溫度、10-8至10-3torr(托)的真空度、0.01至100Å/sec的沉積速度、10Å至5μm的層厚度範圍內適當地進行選擇。並且,在電洞注入層表面,根據需要可追加沉積電荷發生層。作為電荷發生層物質可使用常規的物質,可舉例HATCN。The hole injection layer material is deposited on the upper portion of the first electrode by a vacuum deposition method, a spin coating method, a casting method, an LB (Langmuir-Blodgett) method, or the like, thereby forming the hole injection layer 200. In the case of forming the hole injection layer by the above-mentioned vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer 200, the structure and thermal characteristics of the hole injection layer required, etc., but generally It can be appropriately selected within a deposition temperature of 50-500°C, a vacuum degree of 10-8 to 10-3torr (torr), a deposition speed of 0.01 to 100 Å/sec, and a layer thickness of 10 Å to 5 μm. In addition, a charge generation layer can be additionally deposited on the surface of the hole injection layer as needed. As the charge generation layer material, conventional materials can be used, and HATCN can be exemplified.
接著,藉由真空沉積法、旋塗法、鑄造法、LB法等來在上述電洞注入層200上部沉積電洞輸送層物質,由此可形成電洞輸送層300。在藉由上述真空沉積法來形成電洞輸送層的情況下,其沉積條件因使用的化合物而不同,但通常,較佳地,在與電洞注入層的形成幾乎相同的條件範圍內進行選擇。Next, the hole transport layer material is deposited on the hole injection layer 200 by a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like, thereby forming the hole transport layer 300. In the case of forming the hole transport layer by the above-mentioned vacuum deposition method, the deposition conditions vary depending on the compound used, but generally, it is preferable to select within the range of almost the same conditions as the formation of the hole injection layer .
上述電洞輸送層300可使用習知的化合物而形成。根據本發明的一實例,電洞輸送層300可以是1層以上,雖然圖中未示出,但在上述電洞輸送層300上可形成發光輔助層。The hole transport layer 300 can be formed using a known compound. According to an example of the present invention, the hole transport layer 300 may be more than one layer. Although not shown in the figure, a light-emitting auxiliary layer may be formed on the hole transport layer 300 described above.
藉由真空沉積法、旋塗法、鑄造法、LB法等方法,在上述電洞輸送層300或發光輔助層上沉積發光層物質,由此可形成發光層400。在藉由上述真空沉積法來形成發光層的情況下,其沉積條件因使用的化合物而不同,但通常,較佳地,在與電洞注入層的形成幾乎相同的條件範圍內進行選擇。並且,上述發光層材料可將習知的化合物用作主體或摻雜劑。The light-emitting layer material is deposited on the hole transport layer 300 or the light-emitting auxiliary layer by a vacuum deposition method, a spin coating method, a casting method, or an LB method, thereby forming the light-emitting
並且,在發光層中,與磷光摻雜劑一同使用的情況下,為了防止三重態激子或電洞向電子輸送層擴散的現象,藉由真空沉積法或旋塗法還可層疊電洞抑制材料(HBL)。此時可使用的電洞抑制物質不受特別的限制,但可從用作電洞抑制材料的習知的物質中選擇任意物質來利用。例如,可例舉噁二唑衍生物或三唑衍生物、菲咯啉衍生物或日本特開平11-329734(A1)中所記載的電洞抑制材料等,代表性地,可使用Balq(雙(8-羥基-2-甲基喹啉)-鋁聯苯酚鹽)、菲咯啉(phenanthrolines)類化合物(如通用顯示器(UDC)公司的BCP(Basso Coupoline))等。In addition, when used together with phosphorescent dopants in the light-emitting layer, in order to prevent the triplet excitons or holes from diffusing into the electron transport layer, a vacuum deposition method or a spin coating method can also be laminated to suppress the holes Material (HBL). The hole suppressing substance that can be used at this time is not particularly limited, but any substance can be selected and used from conventional substances used as hole suppressing materials. For example, an oxadiazole derivative or a triazole derivative, a phenanthroline derivative, or the hole suppressing material described in JP 11-329734 (A1) can be exemplified. Representatively, Balq (double (8-hydroxy-2-methylquinoline)-aluminum biphenolate), phenanthrolines (phenanthrolines) compounds (such as BCP (Basso Coupoline) of Universal Display (UDC)), etc.
在如上形成的發光層400上部形成有電子輸送層500,此時,上述電子輸送層可藉由真空沉積法、旋塗法、鑄造法等方法來形成。並且,上述電子輸送層的沉積條件因使用的化合物而不同,但通常,較佳地,在與電洞注入層的形成幾乎相同的條件範圍內進行選擇。An electron transport layer 500 is formed on the light-emitting
之後,可在上述電子輸送層500上部沉積電子注入層物質來形成電子注入層600,此時,上述電子輸送層可藉由真空沉積法、旋塗法、鑄造法等的方法來形成常規的電子注入層物質。After that, the electron injection layer material can be deposited on the electron transport layer 500 to form the electron injection layer 600. At this time, the electron transport layer can be formed by vacuum deposition, spin coating, casting and other methods to form conventional electrons. Inject layer material.
上述有機發光裝置的電洞注入層200、電洞輸送層300、發光層400、電子輸送層500可使用如下的物質,不局限於此。 The following substances can be used for the hole injection layer 200, the hole transport layer 300, the
藉由真空沉積法或濺射法等的方法來在電子注入層600上形成用於注入電子的第二電極2000。作為第二電極,可使用多種金屬。具體例有鋁、金、銀、鎂等的物質。The second electrode 2000 for injecting electrons is formed on the electron injection layer 600 by a method such as a vacuum deposition method or a sputtering method. As the second electrode, various metals can be used. Specific examples include substances such as aluminum, gold, silver, and magnesium.
本發明的有機發光裝置不僅可以採用第一電極、電洞注入層、電洞輸送層、發光層、電子輸送層、電子注入層、第二電極結構的有機發光裝置,還可採用多種結構的有機發光裝置的結構,根據需要,還可形成一層或兩層的中間層。The organic light-emitting device of the present invention can not only adopt organic light-emitting devices with a first electrode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a second electrode structure, but also organic light-emitting devices with a variety of structures. For the structure of the light-emitting device, one or two intermediate layers can also be formed as required.
如上所述,根據本發明形成的各個有機物層的厚度可根據所需的程度來進行調節,具體為10至1000nm,更具體地可以為20至150nm。As described above, the thickness of each organic layer formed according to the present invention can be adjusted according to a desired degree, specifically 10 to 1000 nm, more specifically 20 to 150 nm.
根據本發明的一實例,在上述第一電極1000中,在使電洞注入層200介入的電極的外側可形成覆蓋層3000。並且,在上述第二電極2000中,在使電子注入層600介入的電極外側可形成覆蓋層3000,但不局限於此,上述覆蓋層3000可藉由沉積工序形成,上述覆蓋層3000的厚度可以為100至1000Å,更具體地可以為300至1000Å。此時,可防止覆蓋層的透射率降低。According to an example of the present invention, in the above-mentioned first electrode 1000, a cover layer 3000 may be formed on the outer side of the electrode where the hole injection layer 200 is inserted. In addition, in the second electrode 2000, the covering layer 3000 may be formed on the outside of the electrode where the electron injection layer 600 is inserted, but it is not limited to this. The covering layer 3000 may be formed by a deposition process, and the thickness of the covering layer 3000 may be It is 100 to 1000 Å, more specifically 300 to 1000 Å. At this time, the transmittance of the cover layer can be prevented from decreasing.
針對本實施方式的有機發光化合物,均可適用對於本發明的第一實施方式記載的內容,但可不局限於此。Regarding the organic light-emitting compound of this embodiment, the content described in the first embodiment of the present invention can be applied, but it is not limited to this.
以下,藉由本發明的實施例進行更具體的說明,本發明的範圍不局限於本實施例。Hereinafter, an embodiment of the present invention will be used for more specific description, and the scope of the present invention is not limited to this embodiment.
中間體的合成Synthesis of intermediates
為了合成目的化合物,合成中間體(IM,Intermediate)。In order to synthesize the target compound, an intermediate (IM, Intermediate) is synthesized.
製備例1:IM1的合成Preparation Example 1: Synthesis of IM1
以下IM1的合成法如下。 The synthesis method of the following IM1 is as follows.
在圓底燒瓶中,將菲-9-基硼酸(phenanthrene-9-ylboronic acid)20.0g、1-溴-4-碘苯15.7g溶解於600ml的1,4-二噁烷中,並放入100ml的K2 CO3 (2M)和2.5g的Pd(PPh3 )4 之後,進行回流攪拌。利用薄層層析法(TLC)來確認反應,並添加水之後,結束反應。利用甲基纖維素(MC)來提取有機層,並進行減壓過濾之後進行柱純化,由此得到中間體IM1 15.3g(收率65%)。In a round-bottom flask, dissolve 20.0g of phenanthrene-9-ylboronic acid and 15.7g of 1-bromo-4-iodobenzene in 600ml of 1,4-dioxane and put them in After 100 ml of K 2 CO 3 (2M) and 2.5 g of Pd (PPh 3 ) 4 , reflux and stirring were performed. The reaction was confirmed by thin layer chromatography (TLC), and after adding water, the reaction was terminated. The organic layer was extracted with methyl cellulose (MC), filtered under reduced pressure, and then subjected to column purification, thereby obtaining 15.3 g of intermediate IM1 (yield 65%).
製備例2及3:IM2及IM3的合成Preparation examples 2 and 3: Synthesis of IM2 and IM3
以與上述IM1相同的方法,如下列表1所示,改變起始物質來合成如下的IM2及IM3。 In the same way as the above IM1, as shown in Table 1 below, the starting materials were changed to synthesize the following IM2 and IM3.
表1
覆蓋層用化合物的合成Synthesis of compound for covering layer
合成例1:化合物11的合成 Synthesis Example 1: Synthesis of Compound 11
在圓底燒瓶中,將IM1 3.0g、二([1,1':4',1''-三聯苯]-4-基)胺(di([1,1':4',1''-terphenyl]-4-yl)amine))4.7g、t-BuONa 1.3g、Pd2 (dba)3 0.3g、(t-Bu)3 P 0.4ml溶解於120ml的甲苯,進行回流攪拌。利用薄層層析法來確認反應,並添加水之後,結束反應。利用甲基纖維素來提取有機層,並進行減壓過濾之後進行再結晶,由此得到化合物11 4.0g(收率61%)。In a round bottom flask, mix IM1 3.0g, two ([1,1':4',1''-terphenyl]-4-yl)amine (di([1,1':4',1'' -terphenyl]-4-yl)amine)) 4.7 g, 1.3 g of t-BuONa, 0.3 g of Pd 2 (dba) 3 , and 0.4 ml of (t-Bu) 3 P were dissolved in 120 ml of toluene and stirred under reflux. The reaction was confirmed by thin layer chromatography, and after adding water, the reaction was terminated. The organic layer was extracted with methyl cellulose, filtered under reduced pressure, and then recrystallized to obtain 4.0 g of compound 11 (yield 61%).
m/z:725.31(100.0%)、726.31(61.4%)、727.31(18.2%)、728.32(3.6%)m/z: 725.31 (100.0%), 726.31 (61.4%), 727.31 (18.2%), 728.32 (3.6%)
玻璃轉化溫度(Tg;TA儀器(TA instruments),DSC-2500):140℃Glass transition temperature (Tg; TA instruments, DSC-2500): 140°C
合成例2:化合物227的合成 Synthesis Example 2: Synthesis of Compound 227
以與合成例1相同的方法,使用IM2來代替IM1,合成化合物227(收率60%)。In the same manner as in Synthesis Example 1, IM2 was used instead of IM1 to synthesize compound 227 (yield 60%).
m/z:725.31(100.0%)、726.31(61.4%)、727.31(18.2%)、728.32(3.6%)m/z: 725.31 (100.0%), 726.31 (61.4%), 727.31 (18.2%), 728.32 (3.6%)
合成例3:化合物119的合成 Synthesis Example 3: Synthesis of Compound 119
以與合成例1相同的方法,使用IM3來代替IM1,合成化合物119(收率59%)。In the same manner as in Synthesis Example 1, IM3 was used instead of IM1 to synthesize compound 119 (yield 59%).
m/z:725.31(100.0%)、726.31(61.4%)、727.31(18.2%)、728.32(3.6%)m/z: 725.31 (100.0%), 726.31 (61.4%), 727.31 (18.2%), 728.32 (3.6%)
合成例4:化合物398的合成 Synthesis Example 4: Synthesis of Compound 398
在圓底燒瓶中,將IM1 3.0g、[1,1':4',1''-三聯苯]-4-胺([1,1':4',1''-terphenyl]-4-amine)2.2g、t-BuONa 1.3g、Pd2 (dba)3 0.3g、(t-Bu)3 P 0.4ml溶解於120ml的甲苯,進行回流攪拌。利用薄層層析法來確認反應,並添加水之後,結束反應。利用甲基纖維素來提取有機層,並進行減壓過濾之後進行再結晶,由此得到化合物398 4.2g(收率62%)。In a round bottom flask, mix IM1 3.0g, [1,1':4',1''-terphenyl]-4-amine ([1,1':4',1''-terphenyl]-4- amine) 2.2 g, t-BuONa 1.3 g, Pd 2 (dba) 3 0.3 g, and (t-Bu) 3 P 0.4 ml were dissolved in 120 ml of toluene and stirred under reflux. The reaction was confirmed by thin layer chromatography, and after adding water, the reaction was terminated. The organic layer was extracted with methylcellulose, filtered under reduced pressure, and then recrystallized to obtain 4.2 g of compound 398 (yield 62%).
m/z:749.31(100.0%)、750.31(63.5%)、751.31(19.6%)、752.32(4.0%)m/z: 749.31 (100.0%), 750.31 (63.5%), 751.31 (19.6%), 752.32 (4.0%)
合成例5:化合物553的合成 Synthesis Example 5: Synthesis of Compound 553
以與合成例4相同的方法,使用2-溴三亞苯(2-bromotriphenylene)來代替IM1,合成化合物553(收率60%)。In the same manner as in Synthesis Example 4, using 2-bromotriphenylene (2-bromotriphenylene) instead of IM1, compound 553 was synthesized (yield 60%).
m/z:697.28(100.0%)、698.28(58.8%)、699.28(17.0%)、700.29(3.2%)m/z: 697.28 (100.0%), 698.28 (58.8%), 699.28 (17.0%), 700.29 (3.2%)
有機發光裝置的製備Preparation of organic light emitting device
根據第1圖中所記載的結構來製備有機發光裝置。有機發光裝置可至下而上依次層疊第一電極(電洞注入電極1000)/電洞注入層200/電洞輸送層300/發光層400/電子輸送層500/電子注入層600/第二電極(電子注入電極2000)/覆蓋層3000。According to the structure described in Figure 1, an organic light-emitting device was prepared. The organic light-emitting device can sequentially stack the first electrode (hole injection electrode 1000)/hole injection layer 200/hole transport layer 300/
在第1圖中,當製備有機發光裝置時,基板10可以為透明的玻璃基板或可彎曲的塑膠基板。In Figure 1, when the organic light-emitting device is prepared, the substrate 10 may be a transparent glass substrate or a flexible plastic substrate.
第一電極1000用作用於注入有機發光裝置的電洞的陽極。為了可注入電洞,利用具有低的功函數的物質,可由氧化銦錫(ITO)、氧化銦鋅(IZO)、石墨烯(grapheme)之類的透明的材質形成。The first electrode 1000 serves as an anode for injecting holes of the organic light-emitting device. In order to be able to inject holes, a substance with a low work function is used, which can be formed of transparent materials such as indium tin oxide (ITO), indium zinc oxide (IZO), and grapheme.
在電洞注入層200、電洞輸送層300、發光層400、電子輸送層500中,使用下列表2中所整理的多種物質。In the hole injection layer 200, the hole transport layer 300, the light-emitting
表2
在電子注入層600上形成用於注入電子的第二電極2000。作為第二電極,可使用多種金屬。具體例有鋁、金、銀等的物質。A second electrode 2000 for injecting electrons is formed on the electron injection layer 600. As the second electrode, various metals can be used. Specific examples include substances such as aluminum, gold, and silver.
實施例1:本發明的有機發光裝置的製備Example 1: Preparation of the organic light-emitting device of the present invention
在形成包含Ag的反射層的ITO基板上,作為電洞注入層將600Å的HI01進行製膜,將50Å的HATCN進行製膜,作為電洞輸送層將500Å的HT01進行製膜之後,作為上述發光層摻雜3%的BH01:BD01,以250Å進行製膜。接著,作為電子輸送層將300Å的ET01:Liq(1:1)進行製膜之後,沉積LiF 10Å,形成電子注入層。接著,以15nm的厚度沉積MgAg,在上述陰極上,作為覆蓋層,以600Å厚度沉積在合成例1中製備的化合物。將該裝置密封(Encapsulation)於手套箱中,從而製備有機發光裝置。On an ITO substrate on which a reflective layer containing Ag is formed, 600Å HI01 is formed as a hole injection layer, 50Å HATCN is formed as a film, and 500Å HT01 is formed as a hole transport layer. The layer is doped with 3% BH01: BD01, and the film is formed at 250 Å. Next, 300Å of ET01:Liq (1:1) was deposited as an electron transport layer, and LiF 10Å was deposited to form an electron injection layer. Next, MgAg was deposited in a thickness of 15 nm, and on the above-mentioned cathode, as a covering layer, the compound prepared in Synthesis Example 1 was deposited in a thickness of 600 Å. The device was sealed (Encapsulation) in a glove box to prepare an organic light-emitting device.
實施例2至5:本發明的有機發光裝置的製備Examples 2 to 5: Preparation of the organic light emitting device of the present invention
以與實施例1相同的方法進行製備,分別使用在合成例2至5中製備的化合物來代替合成例1中製備的化合物,製備將覆蓋層製膜的有機發光裝置。The preparation was performed in the same manner as in Example 1, and the compounds prepared in Synthesis Examples 2 to 5 were used instead of the compounds prepared in Synthesis Example 1, respectively, to prepare an organic light-emitting device in which a cover layer was formed.
比較例1至3:有機發光裝置的製備Comparative Examples 1 to 3: Preparation of Organic Light-Emitting Device
以與實施例1相同的方法進行製備,分別使用下列表3中所示的Ref.1至Ref.3來代替合成例1中製備的化合物,製備將覆蓋層製膜的有機發光裝置。The preparation was carried out in the same manner as in Example 1, and Ref. 1 to Ref. 3 shown in Table 3 below were used instead of the compound prepared in Synthesis Example 1 to prepare an organic light-emitting device in which a cover layer was formed.
表3
實驗例1:有機發光裝置的性能評價Experimental example 1: Performance evaluation of organic light-emitting device
利用吉時利2400源測量單元(Kiethley 2400 source measurement unit)施加電壓來注入電子及電洞,利用柯尼卡美能達(Konica Minolta)分光輻射計(CS-2000)來測定發光時的亮度,由此在大氣壓條件下,測定對於施加電壓的電流密度及亮度,從而評價實施例1至實施例5及比較例1至比較例3的有機發光裝置的性能,並將其結果示於下列表4中。The Kiethley 2400 source measurement unit is used to apply voltage to inject electrons and holes, and the Konica Minolta spectroradiometer (CS-2000) is used to measure the brightness of light emission. Under atmospheric pressure conditions, the current density and brightness with respect to the applied voltage were measured to evaluate the performance of the organic light-emitting devices of Examples 1 to 5 and Comparative Examples 1 to 3, and the results are shown in Table 4 below .
表4
本發明相比於比較例1,在胺的一側面具有三亞苯作為由六元環形成的三環以上的稠芳基,由此具有高折射率,分子間薄膜排列變得優秀的同時增大紫外線區域的吸收波長,藉由高Tg,有效改善有機發光裝置的效率及壽命。Compared with Comparative Example 1, the present invention has triphenylene as a condensed aromatic group with three or more rings formed by six-membered rings on one side of the amine, thereby having a high refractive index, and the alignment of the intermolecular thin film is improved while increasing The absorption wavelength in the ultraviolet region, with high Tg, effectively improves the efficiency and lifetime of the organic light emitting device.
並且,本發明相比於比較例2,可維持使可見光區域的吸收的寬的帶隙,從CIEy座標結果中可確認可實現高色純度的有機發光裝置。In addition, compared with Comparative Example 2, the present invention can maintain a wider band gap for absorption in the visible light region, and it can be confirmed from the CIEy coordinate results that an organic light-emitting device with high color purity can be realized.
進而,本發明相比於比較例3,用一個胺使分子的龐大特性最小化,還能以小的分子量有效改善折射率,由此可實現高效率及高色純度。Furthermore, compared with Comparative Example 3, the present invention uses a single amine to minimize the bulkiness of the molecule, and can effectively improve the refractive index with a small molecular weight, thereby achieving high efficiency and high color purity.
實驗例2:折射率的評價Experimental example 2: Evaluation of refractive index
利用化合物398(合成例4)及化合物553(合成例5)和表3的Ref.1及Ref.3化合物,在矽基板上借助真空沉積設備分別製備厚度為30nm的沉積膜,並利用橢偏儀裝置(J.A.Woollam Co. Inc, M-2000X)來測定450nm的折射率。其結果如下列表5中所整理。Using compound 398 (synthesis example 4) and compound 553 (synthesis example 5) and the compounds of Ref.1 and Ref.3 in Table 3, a deposition film with a thickness of 30nm was prepared on a silicon substrate with vacuum deposition equipment, and ellipsometry was used. Instrument device (JAWoollam Co. Inc, M-2000X) to measure the refractive index of 450nm. The results are summarized in Table 5 below.
表5
如上表5中所記載,就化合物398及化合物553而言,可確定其折射率為2.1以上,更具體顯示2.2以上的高折射率。該情況下,在高色純度的CIEy 0.040至0.050之間有利於效率最大化。As described in Table 5 above, it was confirmed that compound 398 and compound 553 had a refractive index of 2.1 or more, and more specifically showed a high refractive index of 2.2 or more. In this case, the high color purity CIEy between 0.040 and 0.050 is beneficial to maximize efficiency.
實驗例3:紫外線區域中的吸收強度的評價Experimental example 3: Evaluation of absorption intensity in the ultraviolet region
在紫外線區域中,利用化合物398(合成例4)及化合物553(合成例5)和表3的Ref.1化合物來在矽基板上借助真空沉積設備分別製備厚度為30nm的沉積膜,並利用橢偏儀裝置(J.A.Woollam Co. Inc, M-2000X)來測定250nm~1000nm範圍內的吸收波長。其結果如第2圖中所示。可確認在紫外線吸收區域380nm的基準上,化合物398及化合物553的吸收強度為0.6以上,具體為0.7以上,相比於Ref.1及Ref.3化合物,吸收強度上升30%以上,更具體地,上升50%以上。In the ultraviolet region, the compound 398 (synthesis example 4) and compound 553 (synthesis example 5) and the Ref.1 compound in Table 3 were used to prepare deposited films with a thickness of 30 nm on the silicon substrate with the aid of vacuum deposition equipment. Polarimeter device (JAWoollam Co. Inc, M-2000X) to measure the absorption wavelength in the range of 250nm~1000nm. The results are shown in Figure 2. It can be confirmed that the absorption intensity of compound 398 and compound 553 is 0.6 or more, specifically 0.7 or more based on the ultraviolet absorption region of 380 nm. Compared with Ref.1 and Ref.3 compounds, the absorption intensity is increased by more than 30%, more specifically , An increase of more than 50%.
上述本發明的說明是用於例示性的,本發明所屬技術領域具有通常知識者可以理解在不變更本發明的技術思想或必要特徵的情況下,能夠以其他具體方式容易變形。因此,應理解以上描述的多個實施例在所有實施方式是例示性的,而不是限定性的。例如,以單一型說明的各個結構要素可分散地實施,同樣,說明為分散的多個結構要素也能夠以結合的方式實施。The above description of the present invention is for illustrative purposes, and those with ordinary knowledge in the technical field to which the present invention pertains can understand that it can be easily modified in other specific ways without changing the technical idea or essential features of the present invention. Therefore, it should be understood that the multiple embodiments described above are illustrative in all embodiments and not restrictive. For example, each structural element described in a single type can be implemented in a dispersed manner, and similarly, a plurality of structural elements described as being dispersed can also be implemented in a combined manner.
本發明的範圍由所附的申請專利範圍表示,而不是上述詳細說明,申請專利範圍的含義及範圍以及由其等同概念導出的所有變更或變形的方式應當被解釋為包括在本發明的範圍中。The scope of the present invention is indicated by the scope of the attached patent application, rather than the above detailed description. The meaning and scope of the scope of the patent application and all changes or modifications derived from its equivalent concepts should be construed as being included in the scope of the present invention .
100:基板 200:電洞注入層 300:電洞輸送層 400:發光層 500:電子輸送層 600:電子注入層 1000:第一電極(陽極) 2000:第二電極(陰極) 3000:覆蓋層100: substrate 200: hole injection layer 300: Electric hole transport layer 400: luminescent layer 500: electron transport layer 600: electron injection layer 1000: The first electrode (anode) 2000: Second electrode (cathode) 3000: Overlay
第1圖表示本發明一實例的有機發光裝置的簡圖。 第2圖為比較在紫外線區域中本發明一實例的化合物和比較例化合物的吸收強度的曲線圖。Fig. 1 shows a schematic diagram of an organic light-emitting device according to an example of the present invention. Figure 2 is a graph comparing the absorption intensity of a compound of an example of the present invention and a compound of a comparative example in the ultraviolet region.
100:基板 100: substrate
200:電洞注入層 200: hole injection layer
300:電洞輸送層 300: Electric hole transport layer
400:發光層 400: luminescent layer
500:電子輸送層 500: electron transport layer
600:電子注入層 600: electron injection layer
1000:第一電極(陽極) 1000: first electrode (anode)
2000:第二電極(陰極) 2000: second electrode (cathode)
3000:覆蓋層 3000: Overlay
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