WO2024033282A1 - Materials for organic electroluminescent devices - Google Patents
Materials for organic electroluminescent devices Download PDFInfo
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- WO2024033282A1 WO2024033282A1 PCT/EP2023/071765 EP2023071765W WO2024033282A1 WO 2024033282 A1 WO2024033282 A1 WO 2024033282A1 EP 2023071765 W EP2023071765 W EP 2023071765W WO 2024033282 A1 WO2024033282 A1 WO 2024033282A1
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- radicals
- atoms
- group
- formula
- aromatic
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- 239000000463 material Substances 0.000 title claims abstract description 93
- 150000001875 compounds Chemical class 0.000 claims abstract description 139
- 239000000203 mixture Substances 0.000 claims abstract description 53
- 125000003118 aryl group Chemical group 0.000 claims description 91
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000004001 thioalkyl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 238000009472 formulation Methods 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
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- 101000855613 Homo sapiens Cryptochrome-2 Proteins 0.000 claims 1
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- 239000010410 layer Substances 0.000 description 87
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- -1 benzocarboline Chemical compound 0.000 description 30
- 125000001072 heteroaryl group Chemical group 0.000 description 14
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- 238000000151 deposition Methods 0.000 description 9
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- 125000004429 atom Chemical group 0.000 description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 230000003111 delayed effect 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
- 238000005401 electroluminescence Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
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- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 4
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- LNJBTNLVEZXDMV-UHFFFAOYSA-N 5-(9h-carbazol-3-yl)benzimidazolo[1,2-a]benzimidazole Chemical compound C12=CC=CC=C2N2C3=CC=CC=C3N=C2N1C1=CC=C(NC=2C3=CC=CC=2)C3=C1 LNJBTNLVEZXDMV-UHFFFAOYSA-N 0.000 description 3
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- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
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- 125000004986 diarylamino group Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
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- 229910052783 alkali metal Inorganic materials 0.000 description 2
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- 125000000304 alkynyl group Chemical group 0.000 description 2
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
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- 150000001491 aromatic compounds Chemical class 0.000 description 2
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- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
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- 239000012159 carrier gas Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- 150000007858 diazaphosphole derivatives Chemical class 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- XXPBFNVKTVJZKF-UHFFFAOYSA-N dihydrophenanthrene Natural products C1=CC=C2CCC3=CC=CC=C3C2=C1 XXPBFNVKTVJZKF-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 1
- SWGQKRKXZZPKJA-UHFFFAOYSA-N indeno[2,1-a]fluorene-1,2-diamine Chemical class C1=CC=C2C=C3C4=CC5=C(N)C(N)=CC=C5C4=CC=C3C2=C1 SWGQKRKXZZPKJA-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004246 ligand exchange chromatography Methods 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- RQNMYNYHBQQZSP-UHFFFAOYSA-M methylmagnesium chloride Chemical compound C[Mg]Cl RQNMYNYHBQQZSP-UHFFFAOYSA-M 0.000 description 1
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- VXNSQGRKHCZUSU-UHFFFAOYSA-N octylbenzene Chemical compound [CH2]CCCCCCCC1=CC=CC=C1 VXNSQGRKHCZUSU-UHFFFAOYSA-N 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 150000002991 phenoxazines Chemical class 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- BUAWIRPPAOOHKD-UHFFFAOYSA-N pyrene-1,2-diamine Chemical class C1=CC=C2C=CC3=C(N)C(N)=CC4=CC=C1C2=C43 BUAWIRPPAOOHKD-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- GDISDVBCNPLSDU-UHFFFAOYSA-N pyrido[2,3-g]quinoline Chemical compound C1=CC=NC2=CC3=CC=CN=C3C=C21 GDISDVBCNPLSDU-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BZLZKLMROPIZSR-UHFFFAOYSA-N triphenylsilicon Chemical compound C1=CC=CC=C1[Si](C=1C=CC=CC=1)C1=CC=CC=C1 BZLZKLMROPIZSR-UHFFFAOYSA-N 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
Definitions
- the present invention describes heterocyclic derivatives substituted by at least one cyano group, as well as compositions and devices comprising these compounds, especially organic electroluminescent devices comprising these compounds as host materials.
- OLEDs organic electroluminescent devices
- phosphorescent organometallic complexes are often used as emitting materials.
- OLEDs organic electroluminescent devices
- triplet emission phosphorescence
- the properties of phosphorescent OLEDs are not only determined by the triplet emitters used.
- the other materials used such as host materials or charge transport materials, are also of particular importance. Improvements in these materials can therefore also lead to improvements in the OLED properties.
- An emitter compound here is taken to mean a compound which emits light during operation of the electronic device.
- a host compound in this case is taken to mean a compound which is present in the mixture in a greater proportion than the emitter compound.
- the term matrix compound and the term host compound can be used synonymously.
- the host compound preferably does not emit light. Even if a plurality of different host compounds are present in the mixture of the emitting layer, their individual proportions are typically greater than the proportion of the emitter compounds, or the proportions of the individual emitter compounds if a plurality of emitter compounds are present in the mixture of the emitting layer.
- the emitter compound is typically the component present in smaller amount, i.e. in a smaller proportion than the other compounds present in the mixture of the emitting layer.
- the emitter compound is also referred to as dopant.
- Host materials for use in organic electronic devices are well known to the person skilled in the art.
- the term "matrix material" is also frequently used in the prior art when what is meant is a host material for phosphorescent emitters. This use of the term is also applicable to the present invention.
- a multitude of host materials has been developed both for fluorescent and for phosphorescent electronic devices.
- 6H-Benzimidazolo[1,2-a]benzimidazole (BimBim) is a commonly used building block in the synthesis and development of high triplet energy (T1) host materials for next generation blue organic light emitting diodes (OLED). It was first described in WO11160757A1 and W012130709A1.
- the problem addressed by the present invention is that of providing compounds which are especially suitable for use as host material in a phosphorescent or fluorescent OLEDs or as electron transport materials.
- a further means of improving the performance data of electronic devices, especially of organic electroluminescent devices is to use combinations of two or more materials, especially two or more host materials.
- the invention therefore provides a compound of the following formula (1):
- Ar 1 is a group of formula (
- Y is the same or different at each instance and is CR Y or N, or two groups Y form a condensed ring together, with the proviso that the Y connected with Y 1 are C if p is 1 and CR Y or N if p is 0; and with the proviso that up to two Y are N each cyclus in the group of formula (Ar1); Y 1 is O, S, CR Y 2 or a single bond; p is 0 or 1 ;
- Q is C, Ge or Si
- X is the same or different at each instance and is CR X or N, or two groups X form a condensed ring together, with the proviso that the X connected with N is C;
- R stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms, where in each case one or more non-adjacent CH2 groups may be replaced by SO, SO2, O, S and where one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms.
- An aryl group in the sense of this invention contains 6 to 60 aromatic ring atoms, preferably 6 to 40 aromatic ring atoms, more preferably 6 to 20 aromatic ring atoms; a heteroaryl group in the sense of this invention contains 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, more preferably 5 to 20 aromatic ring atoms, at least one of which is a heteroatom.
- the heteroatoms are preferably selected from N, O and S. This represents the basic definition. If other preferences are indicated in the description of the present invention, for example with respect to the number of aromatic ring atoms or the heteroatoms present, these apply.
- An aryl group or heteroaryl group here is taken to mean either a simple aromatic ring, i.e. benzene, or a simple heteroaromatic ring, for example pyridine, pyrimidine or thiophene, or a condensed (annellated) aromatic or heteroaromatic polycycle, for example naphthalene, phenanthrene, quinoline or carbazole.
- a condensed (annellated) aromatic or heteroaromatic polycycle in the sense of the present application consists of two or more simple aromatic or heteroaromatic rings condensed with one another.
- An aryl or heteroaryl group which may in each case be substituted by the above-mentioned radicals and which may be linked to the aromatic or heteroaromatic ring system via any desired positions, is taken to mean, in particular, groups derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benz- anthracene, benzophenanthrene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzo- thiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-
- aryloxy group in accordance with the definition of the present invention is taken to mean an aryl group, as defined above, which is bonded via an oxygen atom.
- An analogous definition applies to heteroaryloxy groups.
- An aromatic ring system in the sense of this invention contains 6 to 60 C atoms in the ring system, preferably 6 to 40 C atoms, more preferably 6 to 20 C atoms.
- a heteroaromatic ring system in the sense of this invention contains 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, more preferably 5 to 20 aromatic ring atoms, at least one of which is a heteroatom.
- the heteroatoms are preferably selected from N, O and/or S.
- An aromatic or heteroaromatic ring system in the sense of this invention is intended to be taken to mean a system which does not necessarily contain only aryl or heteroaryl groups, but instead in which, in addition, a plurality of aryl or heteroaryl groups may be connected by a non-aromatic unit (preferably less than 10% of the atoms other than H), such as, for example, an sp 3 - hybridised C, Si, N or O atom, an sp 2 -hybridised C or N atom or an sp-hybridised C atom.
- systems such as 9,9’-spirobifluorene, 9,9’-diarylfluorene, triarylamine, diaryl ether, stilbene, etc., are also intended to be taken to be aromatic ring systems in the sense of this invention, as are systems in which two or more aryl groups are connected, for example, by a linear or cyclic alkyl, alkenyl or alkynyl group or by a silyl group.
- systems in which two or more aryl or heteroaryl groups are linked to one another via single bonds are also taken to be aromatic or heteroaromatic ring systems in the sense of this invention, such as, for example, systems such as biphenyl, terphenyl or diphenyltriazine.
- An aromatic or heteroaromatic ring system having 5 - 60 aromatic ring atoms, which may in each case also be substituted by radicals as defined above and which may be linked to the aromatic or heteroaromatic group via any desired positions, is taken to mean, in particular, groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans- indenofluorene, truxene, isotruxene, spirotruxene,
- a straight-chain alkyl group having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms in which, in addition, individual H atoms or CH2 groups may be substituted by the groups mentioned above under the definition of the radicals, is preferably taken to mean the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, cyclooct
- An alkoxy or thioalkyl group having 1 to 40 C atoms is preferably taken to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t- butoxy, n-pentoxy, s-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cyclo- heptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy, 2,2,2-tri- fluoroethoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, n-
- the above-mentioned formulation is also intended to be taken to mean that, in the case where one of the two radicals represents hydrogen, the second radical is bonded at the position to which the hydrogen atom was bonded, with formation of a ring. This is illustrated by the following scheme:
- the two radicals are adjacent radicals.
- Adjacent radicals in the sense of the present invention are radicals which are bonded to atoms which are linked directly to one another or which are bonded to the same atom.
- the compound of formula (1) is selected from the compounds of formulae (1-1) to (1-4),
- the group Ar 1 of formula (1) is selected from the groups of formulae (Ar1-1) to (Ar1-5)
- the compound of formula (1) is selected from the compounds of formulae (1-1-1-1) to (1-4- 5-4),
- Q is C and Ar1 is a group of formulae (Ar1-1) to (Ar1-4) or Q is Ge or Si and Ar 1 is a group of formula (Ar-4).
- X stand on each occurrence, identically or differently for CR X .
- X stand on each occurrence, identically or differently for CR X and Y stand on each occurrence, identically or differently for CR Y .
- no X or Y is N.
- Y stand on each occurrence, identically or differently for CR Y .
- the compound is a compound according to one of the formulae (1-1-1-1) to (1 -1-5-4) or (1-2-1-1) to (1-2-5-4).
- the compound contains not more than two substituents R that are a group other than H, F, CN or D, preferably other than H or D.
- the compound contains not more than two substituents selected from R x and/or R Y are a group other than H, F, CN or D, preferably other than H or D.
- the compound is a compound according to one of the formulae (1-1-1-1) to (1 -1-5-4) or (1-2-1-1) to (1-2-5-4), preferably according to one of the formulae (1-1-1-1a) to (1-1-5-4a) or (1-2-1-1a) to (1-2-5-4a).
- R 1 , R x , R Y stand on each occurrence, identically or differently, for H, D, F, a straight-chain alkyl group having 1 to 20, preferably 1 to 10, more preferably 1 to 6 C atoms or branched or a cyclic alkyl group having 3 to 20, preferably 3 to 10, more preferably 3 to 6 C atoms, each of which may be substituted by one or more radicals R, an aromatic or heteroaromatic ring system having 5 to 40, preferably 5 to 30, more preferably 5 to 18 aromatic ring atoms, which may in each case be substituted by one or more radicals R, where two radicals R 1 and/or a radical R 1 and a radical R Y may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R.
- R 1 , R x , R Y stand on each occurrence, identically or differently, for H, D, a straight-chain alkyl group having 1 to 10, preferably 1 to 6 C atoms or branched or a cyclic alkyl group having 3 to 10, preferably 3 to 6 C atoms, each of which may be substituted by one or more radicals R, or an aromatic or heteroaromatic ring system having 5 to 18 aromatic ring atoms, preferably 6 to 12 aromatic ring atoms, which may in each case be substituted by one or more radicals R, where two radicals R 1 and/or a radical R 1 and a radical R Y may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R.
- R x , R Y stand for H or D.
- R 1 , R x , R Y standing for an aromatic or heteroaromatic ring system it is preferred that they are the same or different at each instance and selected from the groups of the following formulae Ar-1 to Ar-83:
- Ar 3 is the same or different at each instance and is a bivalent aromatic or heteroaromatic ring system which has 6 to 18 aromatic ring atoms and may be substituted in each case by one or more R radicals;
- a 1 is the same or different at each instance and is NR, O, S or C(R)2;
- R 1 stands on each occurrence identically or differently for a straight-chain alkyl group having 1 to 20, preferably 1 to 10, more preferably 1 to 6 C atoms or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, preferably 5 to 18, more preferably 6 to 12 aromatic ring atoms, which may in each case be sub- stituted by one or more radicals R, where two radicals R 1 may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R.
- R 1 stands on each occurrence identically or differently for a straight-chain alkyl group having 1 to 20, preferably 1 to 10, more preferably 1 to 6 C atoms or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, preferably 5 to 18, more preferably 6 to 12 aromatic ring atoms, which may in each case be sub- stituted by one or more radicals R, where two radicals R 1 may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R, preferably two racidals R 1 may form an aromatic or heteroaromatic ring system via at least one single bond.
- R 1 is selected from the groups according to CR3, CR2CR3, Ar-1, Ar-2, Ar-3, Ar-4, preferably Ar-1 and CR3, wherein two R 1 may be connected via a single bond.
- Q and both R 1 are selected as follows:
- the compound of formula (1) is selected from the compounds of formulae (1 -1 - 1 - 1 a) to (1-4-6-4a),
- the present invention therefore further provides a process for preparing the compounds of
- the invention characterized by the following steps: (1) synthesizing the base skeleton of the compound of the formula (1) containing a reactive leaving group or H in place of the Ar 1 group, the reactive leaving group preferably selected from boronic acid, boronic ester, Cl, Br, I, triflate, tosylate or mesylate;
- the present invention furthermore provides a composition
- a composition comprising a material selected from compounds of the formula (1) as defined above and a material selected from electron- transporting host materials that is preferably selected from the group of the triazines, pyrimidines, quinazolines, quinoxalines and lactams, or derivatives of these structures.
- Preferred triazine, pyrimidine, quinazoline or quinoxaline derivatives that can be used as a mixture together with the compounds of the invention are the compounds of the following formulae (e-1), (e-2), (e-3) and (e-4): where R has the meanings given above.
- R is preferably the same or different at each instance and is H or an aromatic or heteroaromatic ring system which has 6 to 30 aromatic ring atoms and which may be substituted by one or more R 1 radicals.
- Ar in the formulae (e-1 a), (e-2a), (e-3a) and (e- 4a) is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 6 to 30 aromatic ring atoms, especially 6 to 24 aromatic ring atoms, and may be substituted by one or more R radicals.
- Suitable aromatic or heteroaromatic ring systems Ar here are the same as set out above as embodiments for Ar, especially the structures Ar-1 to Ar-83.
- Suitable triazine and pyrimidine compounds that may be used as matrix materials together with the compounds of the invention are the compounds depicted in the following table:
- lactams examples are the structures depicted in the following table:
- the composition comprises a first host material selected from compounds of the formula (1) as defined above, a second host material selected from electron-transporting host materials and a third compound selected from phosphorescent emitters, fluorescent emitters and emitters that exhibit TADF (thermally activated delayed fluorescence).
- a first host material selected from compounds of the formula (1) as defined above
- a second host material selected from electron-transporting host materials
- a third compound selected from phosphorescent emitters, fluorescent emitters and emitters that exhibit TADF (thermally activated delayed fluorescence).
- the third compound is selected from phosphorescent emitters.
- Phosphorescence in the context of this invention is understood to mean luminescence from an excited state having higher spin multiplicity, i.e. a spin state > 1, especially from an excited triplet state.
- all luminescent complexes with transition metals or lanthanides, especially all iridium, platinum and copper complexes shall be regarded as phosphorescent emitters.
- Suitable phosphorescent compounds are especially compounds which, when suitably excited, emit light, preferably in the visible region, and also contain at least one atom of atomic number greater than 20, preferably greater than 38 and less than 84, more preferably greater than 56 and less than 80, especially a metal having this atomic number.
- Preferred phosphorescence emitters used are compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, especially compounds containing iridium or platinum.
- Examples of the emitters described above can be found in applications WO 00/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645, EP 1191613, EP 1191612, EP 1191614, WO 05/033244, WO 05/019373, US 2005/0258742, WO 2009/146770, WO 2010/015307, WO 2010/031485, WO 2010/054731, WO 2010/054728, WO 2010/086089, WO 2010/099852, WO 2010/102709, WO 2011/032626, WO 2011/066898, WO 2011/157339, WO 2012/007086, WO 2014/008982, WO 2014/023377, WO 2014/094961, WO 2014/094960, WO 2015/036074, WO 2015/104045, WO 2015/117718, WO 2016/015815, WO 2016/124304, WO 2017/032439,
- the third compound is selected from emitters which exhibit thermally activated delayed fluorescence (TADF emitters) (e.g. H. Uoyarna et al., Nature 2012, vol. 492, 234).
- TADF emitters are organic materials in which the energy gap between the lowest triplet state Ti and the first excited singlet state Si is sufficiently small that the Si state is thermally accessible from the Ti state.
- the TADF emitter is preferably an aromatic compound having both donor and acceptor substituents, with only slight spatial overlap between the LIIMO and the HOMO of the compound. What is understood by donor and acceptor substituents is known in principle to those skilled in the art.
- Suitable donor substituents are especially diaryl- or -heteroarylamino groups and carbazole groups or carbazole derivatives, each preferably bonded to the aromatic compound via N. These groups may also have further substitution.
- Suitable acceptor substituents are especially cyano groups, but also, for example, electron-deficient heteroaryl groups which may also have further substitution, for example substituted or unsubstituted triazine groups.
- the third compound is selected from fluorescent emitters.
- Preferred fluorescent emitters are aromatic anthracenamines, aro- matic anthracenediamines, aromatic pyrenamines, aromatic pyrenediamines, aromatic chrysenamines or aromatic chrysenediamines.
- An aromatic anthracenamine is taken to mean a compound in which one diarylamino group is bonded directly to an anthracene group, preferably in the 9-position.
- An aromatic anthracenediamine is taken to mean a com- pound in which two diarylamino groups are bonded directly to an anthracene group, preferably in the 9,10-position.
- Aromatic pyrenamines, pyrenediamines, chrysenamines and chrysenediamines are defined analogously thereto, where the diarylamino groups are preferably bonded to the pyrene in the 1 -position or in the 1,6-position.
- emitters are indenofluorenamines or indenofluorenediamines, for example in accordance with WO 2006/108497 or WO 2006/122630, benzoindenofluorenamines or benzoindenofluorenediamines, for example in accordance with WO 2008/006449, and dibenzoindenofluorenamines or dibenzoindenofluorenediamines, for example in accordance with WO 2007/140847, and the indenofluorene derivatives containing con- densed aryl groups which are disclosed in WO 2010/012328.
- Still further preferred emitters are benzanthracene derivatives as disclosed in WO 2015/158409, anthracene derivatives as disclosed in WO 2017/036573, fluorene dimers connected via heteroaryl groups like in WO 2016/150544 or phenoxazine derivatives as disclosed in WO 2017/028940 and WO 2017/028941.
- Preference is likewise given to the pyrenarylamines disclosed in WO 2012/048780 and WO 2013/185871.
- the composition comprises a first host material selected from compounds of the formula (1) as defined above, a second host material selected from hole-transporting host materials, a third compound selected from phosphorescent emitters and emitters that exhibit TADF (thermally activated delayed fluorescence) and a fourth compound selected from phosphorescent emitters and fluorescent emitters.
- a first host material selected from compounds of the formula (1) as defined above
- a second host material selected from hole-transporting host materials
- TADF thermalally activated delayed fluorescence
- compositions may also comprise further organic or inorganic compounds which are likewise used in the electronic device like, for example, further emitters or further host materials.
- the compound of formula (1) or the composition comprising a compound of formula (1) may be processed by vapour deposition or from solution. If the compositions are applied from solution, formulations of the composition of the invention comprising at least one further solvent are required. These formulations may, for example, be solutions, dispersions or emulsions. For this purpose, it may be preferable to use mixtures of two or more solvents.
- the present invention therefore further provides a formulation comprising a compound of formula (1) or a composition comprising a compound of formula (1) and at least one solvent.
- Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, (-)-fenchone, 1 , 2,3,5- tetramethylbenzene, 1 ,2,4,5-tetramethylbenzene, 1 -methylnaphthalene, 2- methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole,
- the present invention also provides for the use of the compound of formula (1) or of compositions comprising the compound of formula (1) in an organic electronic device, preferably in an emitting layer and/or in an electron-transporting layer.
- the organic electronic device is preferably selected from organic integrated circuits (OlCs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors and organic photoreceptors, particular preference being given to organic electroluminescent devices.
- organic electroluminescent devices containing at least one compound of the formula (1), as described above or described as preferred, are organic light-emitting transistors (OLETs), organic field-quench devices (OFQDs), organic light- emitting electrochemical cells (OLECs, LECs, LEECs), organic laser diodes (O-lasers) and organic light-emitting diodes (OLEDs); OLECs and OLEDs are especially preferred and OLEDs are the most preferred.
- OLETs organic light-emitting transistors
- OFQDs organic field-quench devices
- OLEDs organic light- emitting electrochemical cells
- O-lasers organic laser diodes
- OLEDs organic light-emitting diodes
- the compound of formula (1) as described above or described as preferred is used in a layer having an electron-transporting function in an electronic device.
- the layer is preferably an electron injection layer (EIL), an electron transport layer (ETL), a hole blocker layer (HBL) and/or an emission layer (EML), more preferably an ETL, EIL and/or an EML.
- EIL electron injection layer
- ETL electron transport layer
- HBL hole blocker layer
- EML emission layer
- the compound of formula (1) or the composition is used in an EML as an host material in combination with a electron-transporting host material.
- the present invention further provides an organic electronic device which is especially selected from one of the aforementioned electronic devices and which comprises the compound of formula (1) or compositions comprising the compound of formula (1), as described above or described as preferred, preferably in an emission layer (EML), in an electron transport layer (ETL), in an electron injection layer (EIL) and/or in a hole blocker layer (HBL), very preferably in an EML, EIL and/or ETL and most preferably in an EML.
- EML emission layer
- ETL electron transport layer
- EIL electron injection layer
- HBL hole blocker layer
- the electronic device is an organic electroluminescent device, most preferably an organic light-emitting diode (OLED), containing the compound of formula (1) or a composition comprising the compound of formula (1) in the emission layer (EML).
- OLED organic light-emitting diode
- the organic electroluminescent device is therefore one comprising an anode, a cathode and at least one organic layer comprising at least one light-emitting layer, wherein the at least one light- emitting layer contains at least one compound of the formula (1) or a composition comprising a compound of formula (1) as described above.
- the light-emitting layer in the device of the invention contains preferably between 99.9% and 1% by volume, further preferably between 99% and 10% by volume, especially preferably between 98% and 40% by volume, very especially preferably between 97% and 50% by volume, of host material composed of at least one compound of the formula (1) or composed of at least one a first host material selected from compounds of the formula (1) and a second host material selected from electron-transporting host materials as described above, based on the overall composition of emitter and host material.
- the light-emitting layer in the device of the invention preferably contains between 0.1% and 99% by volume, further preferably between 1% and 90% by volume, more preferably between 2% and 40% by volume, most preferably between 3% and 20% by volume, of the emitter based on the overall composition of the light-emitting layer composed of emitter and host material. If the compounds are processed from solution, preference is given to using the corresponding amounts in % by weight rather than the above-specified amounts in % by volume.
- the light-emitting layer in the device of the invention preferably contains the host material of the formula (1), preferably in combination with a host material selected from electron-transporting host materials, in a percentage by volume ratio between 3:1 and 1 :3, preferably between 1 :2.5 and 1 :1 , more preferably between 1 :2 and 1 :1. If the compounds are processed from solution, preference is given to using the corresponding ratio in % by weight rather than the above-specified ratio in % by volume.
- an electronic device may comprise further layers. These are selected, for example, from in each case one or more hole injection layers, hole transport layers, hole blocker layers, light- emitting layers, electron transport layers, electron injection layers, electron blocker layers, exciton blocker layers, interlayers, charge generation layers (IDMC 2003, Taiwan; Session 21 OLED (5), T. Matsumoto, T. Nakada, J. Endo, K. Mori, N. Kawamura, A. Yokoi, J. Kido, Multiphoton Organic EL Device Having Charge Generation Layer) and/or organic or inorganic p/n junctions.
- IDMC 2003 Taiwan
- Session 21 OLED (5) T. Matsumoto, T. Nakada, J. Endo, K. Mori, N. Kawamura, A. Yokoi, J. Kido, Multiphoton Organic EL Device Having Charge Generation Layer
- the sequence of layers in an organic electroluminescent device is preferably as follows: anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode.
- the sequence of the layers is a preferred sequence.
- An organic electroluminescent device of the invention may contain two or more light- emitting layers.
- at least one of the light-emitting layers contains at least one compound of the formula (1) and compositions comprising a compound of formula (1) as described above. More preferably, these emission layers in this case have several emission maxima between 380 nm and 750 nm overall, such that the overall result is white emission; in other words, various emitting compounds which may fluoresce or phosphoresce and which emit blue or yellow or orange or red light are used in the light- emitting layers.
- three-layer systems i.e.
- Suitable charge transport materials as usable in the hole injection or hole transport layer or electron blocker layer or in the electron transport layer of the organic electroluminescent device of the invention are, for example, the compounds disclosed in Y. Shirota et al., Chem. Rev. 2007, 107(4), 953-1010, or other materials as used in these layers according to the prior art.
- Materials used for the electron transport layer may be any materials as used according to the prior art as electron transport materials in the electron transport layer.
- aluminium complexes for example Alqs, zirconium complexes, for example Zrq4, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketones, lactams, boranes, diazaphosphole derivatives and phosphine oxide derivatives.
- Further suitable materials are derivatives of the above-mentioned compounds as disclosed in JP 2000/053957, WO 2003/060956, WO 2004/028217, WO 2004/080975 and WO 2010/072300.
- Preferred hole transport materials are especially materials which can be used in a hole transport, hole injection or electron blocker layer, such as indenofluoreneamine derivatives (for example according to WO 06/122630 or WO 06/100896), the amine derivatives disclosed in EP 1661888, hexaazatriphenylene derivatives (for example according to WO 01/049806), amine derivatives having fused aromatic systems (for example according to US 5,061,569), the amine derivatives disclosed in WO 95/09147, monobenzoindenofluoreneamines (for example according to WO 08/006449), dibenzoindenofluoreneamines (for example according to WO 07/140847), spirobifluoreneamines (for example according to WO 2012/034627 or the as yet unpublished EP 12000929.5), fluoreneamines (for example according to WO 2014/015937, WO 2014/015938 and WO 2014/015935), spirodibenzopyran
- Preferred cathodes of electronic devices are metals having a low work function, metal alloys or multilayer structures composed of various metals, for example alkaline earth metals, alkali metals, main group metals or lanthanoids (e.g. Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Additionally suitable are alloys composed of an alkali metal or alkaline earth metal and silver, for example an alloy composed of magnesium and silver.
- further metals having a relatively high work function for example Ag or Al, in which case combinations of the metals such as Ca/Ag, Mg/Ag or Ba/Ag, for example, are generally used.
- a thin interlayer of a material having a high dielectric constant between a metallic cathode and the organic semiconductor may also be preferable to introduce a thin interlayer of a material having a high dielectric constant between a metallic cathode and the organic semiconductor.
- useful materials for this purpose are alkali metal or alkaline earth metal fluorides, but also the corresponding oxides or carbonates (e.g. Li F, U2O, BaF2, MgO, NaF, CsF, CS2CO3, etc.). It is also possible to use lithium quinolinate (LiQ) for this purpose.
- the layer thickness of this layer is preferably between 0.5 and 5 nm.
- Preferred anodes are materials having a high work function.
- the anode has a work function of greater than 4.5 eV versus vacuum.
- metals having a high redox potential are suitable for this purpose, for example Ag, Pt or Au.
- metal/metal oxide electrodes e.g. Al/N i/N iO x , AI/PtO x
- at least one of the electrodes has to be transparent or partly transparent in order to enable either the irradiation of the organic material (organic solar cell) or the emission of light (OLED, O-I-ASER).
- Preferred anode materials here are conductive mixed metal oxides.
- ITO indium tin oxide
- IZO indium zinc oxide
- conductive doped organic materials especially conductive doped polymers.
- the anode may also consist of two or more layers, for example of an inner layer of ITO and an outer layer of a metal oxide, preferably tungsten oxide, molybdenum oxide or vanadium oxide.
- the organic electronic device in the course of production, is appropriately (according to the application) structured, contact-connected and finally sealed, since the lifetime of the devices of the invention is shortened in the presence of water and/or air.
- the organic electronic device comprising the composition of the invention is characterized in that one or more organic layers comprising the composition of the invention are coated by a sublimation method.
- the materials are applied by vapour deposition in vacuum sublimation systems at an initial pressure of less than 10' 5 mbar, preferably less than 10' 6 mbar. In this case, however, it is also possible that the initial pressure is even lower, for example less than 10' 7 mbar.
- an organic electroluminescent device characterized in that one or more layers are coated by the OVPD (organic vapour phase deposition) method or with the aid of a carrier gas sublimation.
- the materials are applied at a pressure between 10' 5 mbar and 1 bar.
- OVJP organic vapour jet printing
- the materials are applied directly by a nozzle and thus structured (for example, M. S. Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).
- an organic electroluminescent device characterized in that one or more organic layers comprising the composition of the invention are produced from solution, for example by spin-coating, or by any printing method, for example screen printing, flexographic printing, nozzle printing or offset printing, but more preferably LITI (light-induced thermal imaging, thermal transfer printing) or inkjet printing.
- LITI light-induced thermal imaging, thermal transfer printing
- soluble compounds of the components of the composition of the invention are needed. High solubility can be achieved by suitable substitution of the corresponding compounds.
- Processing from solution has the advantage that the layer comprising the composition of the invention can be applied in a very simple and inexpensive manner. This technique is especially suitable for the mass production of organic electronic devices.
- hybrid methods are possible, in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapour deposition.
- the invention therefore further provides a process for producing an organic electronic device comprising a composition of the invention as described above or described as preferred, characterized in that at least one organic layer comprising a composition of the invention is applied by gas phase deposition, especially by a sublimation method and/or by an OVPD (organic vapour phase deposition) method and/or with the aid of carrier gas sublimation, or from solution, especially by spin-coating or by a printing method.
- gas phase deposition especially by a sublimation method and/or by an OVPD (organic vapour phase deposition) method and/or with the aid of carrier gas sublimation, or from solution, especially by spin-coating or by a printing method.
- an organic layer which is to comprise the composition of the invention and which may comprise multiple different constituents can be applied, or applied by vapour deposition, to any substrate.
- the materials used can each be initially charged in a material source and ultimately evaporated from the different material sources ("co-evaporation”).
- the various materials can be premixed (premix systems) and the mixture can be initially charged in a single material source from which it is ultimately evaporated (“premix evaporation”). In this way, it is possible in a simple and rapid manner to achieve the vapour deposition of a layer with homogeneous distribution of the components without a need for precise actuation of a multitude of material sources.
- the invention accordingly further provides a process characterized in that the at least one compound of the formula (1) as described above or described as preferred and the compositions comprising the compound of formula (1) as described above or described as preferred are deposited from the gas phase successively or simultaneously from at least two material sources, optionally with other materials as described above or described as preferred, and form the organic layer.
- the invention accordingly further provides a process characterized in that the composition of the invention as described above or described as preferred is utilized as material source for the gas phase deposition of the host system and, optionally together with further materials, forms the organic layer.
- the invention further provides a process for producing an organic electronic device comprising a composition of the invention as described above or described as preferred, characterized in that the formulation of the invention as described above is used to apply the organic layer.
- Fabrication of vapor processed OLED devices The manufacturing of the OLED devices is performed accordingly to WO 04/058911 with adapted film thicknesses and layer sequences.
- the following examples V1 , E1 and E2 show data of OLED devices.
- Glass plates with structured ITO (50 nm, indium tin oxide) are pre-treated with an oxygen plasma, followed by an argon plasma.
- the pre-treated glass plates form the substrates on which the OLED devices are fabricated.
- the OLED devices have in principle the following layer structure:
- HIL Hole injection layer
- HTL Hole transporting layer
- EBL Electron blocking layer
- EBL Emissive layer
- HBL Hole blocking layer
- ETL Electron transporting layer
- EIL Electron injection layer
- the cathode is formed by an aluminium layer with a thickness of 100 nm.
- the detailed stack sequence is shown in table A.
- the materials used for the OLED fabrication are presented in table B.
- the emission layer here always consists of at least one matrix material and one phosphorescent material.
- the phosphorescent material is mixed with the matrix material or matrix materials in a certain proportion by volume by co-evaporation.
- the electron-transport layer and hole-injection layer may also consist of a mixture of two or more materials.
- the OLED devices are characterised by standard methods.
- the electroluminescence spectra and the external quantum efficiency (EQE, measured in %) are determined from current/voltage/luminance characteristic lines (IUL characteristic lines) assuming a Lambertian emission profile.
- the electroluminescence (EL) spectra are recorded at a luminous density of 1000 cd/m 2 and the CIE 1931 x and y coordinates are then calculated from the EL spectrum.
- U is defined as the voltage, which is required for a current density of 10 mA/cm 2 .
- the parameter EQE represents the external quantum efficiency at a current density of 10 mA/cm 2 .
- the lifetime LT90 is defined as the time after which the luminance drops from the starting luminance to a proportion of 90% of the starting luminance in the course of operation with a constant current density of 5 mA/cm 2 .
- the device data of various OLED devices are summarized in table A and table C.
- the example V1 represents a comparative example according to the state of the art.
- the examples E1 and E2 show data of inventive OLED devices that use an Ir-complex as emitter.
- the examples E3, E4, and E5 show data of inventive OLED devices that use an Pt-complex as emitter.
- the inventive compounds are especially suitable as a host (matrix) when blended with an electron-conducting host material and a phosphorescent emitter to form the emissive layer of a phosphorescent blue OLED device.
- the representative examples use HH1, HH2, and HH3 as host materials.
- the host compounds HH1, HH2, and HH3 can be exchanged by the compound HH4.
- a comparative compound for the state of the art is represented by StA (structures see table B).
- the use of the inventive compound as a host (matrix) in a phosphorescent blue OLED device results in excellent device data, especially with respect to lifetime LT90 when compared to the state of the art.
- This technical advantage is apparent when examples E1 and E2 are compared to V1 in table A.
- the inventive host compounds HH1 and HH2 in E1 and E2 can also be exchanged with the inventive compound HH4.
- inventive compounds as a host (matrix) in a phosphorescent blue OLED device that incorporate a Pt-complex as emitter results in excellent device data, especially with respect to lifetime LT90. This is apparent in the examples E3 and E4 in table C, where HTM2 is selected from a fluorenamine compound. Moreover, the inventive host compounds HH2 and HH3 in E3 and E4 can also be exchanged with the inventive compound HH4.
- inventive compounds as an electron blocking material in the EBL in a phosphorescent blue OLED results in excellent device data, especially with respect to lifetime LT90 and operational voltage II. This is apparent when comparing example E5 and E4 in table C, where HTM2 is selected from fluorenamine compounds.
- inventive host compound HH3 in E4 and E5 can also be exchanged with the inventive compound HH4.
- Table A Device stack and performance data of vapor processed OLEDs with Ir-complex as emitter
- Table B Structural formulae of vapor processed OLED materials
- Table C Device stack and performance data of vapor processed OLEDs with Pt- complex as emitter
Abstract
The present invention relates to a heterocyclic compound of formula (1) as well as compositions and devices comprising these compounds, especially organic electroluminescent devices comprising these compounds as host materials.
Description
Materials for organic electroluminescent devices
The present invention describes heterocyclic derivatives substituted by at least one cyano group, as well as compositions and devices comprising these compounds, especially organic electroluminescent devices comprising these compounds as host materials.
In organic electroluminescent devices (OLEDs), phosphorescent organometallic complexes are often used as emitting materials. In general, there is still room for improvement in OLEDs, especially OLEDs that exhibit triplet emission (phosphorescence), for example in terms of efficiency, operating voltage and lifetime. The properties of phosphorescent OLEDs are not only determined by the triplet emitters used. Here, the other materials used, such as host materials or charge transport materials, are also of particular importance. Improvements in these materials can therefore also lead to improvements in the OLED properties.
There is also still room for improvement in OLEDs that exhibit singlet emission (fluorescence and/or thermally activated delayed fluorescence), also in terms of efficiency, operating voltage and lifetime. Here too, the properties of fluorescent OLEDs are also not only determined by the singlet emitters but also by the the other materials used, such as the host materials and the charge transport materials. Improvements in these materials can therefore also lead to improvements in the OLED properties.
An emitter compound here is taken to mean a compound which emits light during operation of the electronic device. A host compound in this case is taken to mean a compound which is present in the mixture in a greater proportion than the emitter compound. The term matrix compound and the term host compound can be used synonymously. The host compound preferably does not emit light. Even if a plurality of different host compounds are present in the mixture of the emitting layer, their individual proportions are typically greater than the proportion of the emitter compounds, or the proportions of the individual emitter compounds if a plurality of emitter compounds are present in the mixture of the emitting layer.
If a mixture of a plurality of compounds is present in the emitting layer, the emitter compound is typically the component present in smaller amount, i.e. in a smaller proportion than the other compounds present in the mixture of the emitting layer. In this case, the emitter compound is also referred to as dopant.
Host materials for use in organic electronic devices are well known to the person skilled in the art. The term "matrix material" is also frequently used in the prior art when what is meant is a host material for phosphorescent emitters. This use of the term is also applicable to the present invention. In the meantime, a multitude of host materials has been developed both for fluorescent and for phosphorescent electronic devices.
6H-Benzimidazolo[1,2-a]benzimidazole (BimBim) is a commonly used building block in the synthesis and development of high triplet energy (T1) host materials for next generation blue organic light emitting diodes (OLED). It was first described in WO11160757A1 and W012130709A1.
There is no conjugation between the two benzene rings in the BimBim structure, which leads to a large gap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LIIMO), and therefore a high excited state energy. This is especially favorable for host materials of deep blue OLEDs based on phosphorescence, hyperphosphorescence or hyperfluorescence, because the emitter emission is then unlikely to be quenched by the hosts and high efficiencies can be obtained.
There is generally still a need for improvement in these materials for use as host materials. The problem addressed by the present invention is that of providing compounds which are especially suitable for use as host material in a phosphorescent or fluorescent OLEDs or as electron transport materials.
A further means of improving the performance data of electronic devices, especially of organic electroluminescent devices, is to use combinations of two or more materials, especially two or more host materials.
However, there is still need for improvement in the case of use of the host materials or in the case of use of mixtures of the host materials, especially in relation to efficiency, operating voltage and/or lifetime of the organic electronic device.
Surprisingly, it has been found that compounds and mixtures comprising the compounds described in more detail below solve this problem and are particularly suitable for use in OLEDs. In particular, the OLEDs have a long lifetime, a high efficiency and a low operating voltage. These compounds, the mixture comprising these compounds as well as electronic devices, in particular organic electroluminescent devices, containing these compounds are therefore the object of the present invention.
Formula (1 ) where the symbols and indices used are as follows:
Formula (Ar1) where the dashed bond indicates the bonding position to the nitrogen in formula (1);
Y is the same or different at each instance and is CRY or N, or two groups Y form a condensed ring together, with the proviso that the Y connected with Y1 are C if p is 1 and CRY or N if p is 0; and with the proviso that up to two Y are N each cyclus in the group of formula (Ar1);
Y1 is O, S, CRY2 or a single bond; p is 0 or 1 ;
Q is C, Ge or Si;
X is the same or different at each instance and is CRX or N, or two groups X form a condensed ring together, with the proviso that the X connected with N is C;
R1, Rx, RY stand on each occurrence, identically or differently, for a radical selected from H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, N(R)2, N(Ar)2, NO2, Si(R)a, B(OR)2, OSO2R, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non-adjacent CH2 groups may be replaced by RC=CR, C=C, Si(R)2, Ge(R)2, Sn(R)2, C=O, C=S, C=Se, P(=O)(R), SO, SO2, O, S or CONR and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R, and an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R; where two radicals R1, one radical R1 and one radical RY, two radicals Rx , two radicals RY may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R;
R stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CHO, CN, C(=O)Ar, P(=O)(Ar)2, S(=O)Ar, S(=O)2Ar, N(R')2, N(Ar)2, NO2, Si(R )3, B(OR')2, OSO2R , a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40 C atoms, each of which may be substituted by one or more radicals R , where in each case one or more non-adjacent CH2 groups may be replaced by R C=CR , C=C, Si(R )2, Ge(R )2, Sn(R )2, C=O, C=S, C=Se, P(=O)(R ), SO, SO2, O, S or CONR and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO2, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R , or an aryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R ; where two radicals R may form an aliphatic or aromatic ring system together, which may be substituted by one or more radicals R ;
Ar is, on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case also be substituted by one or more radicals R ;
R stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 20 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl group having 3 to 20 C atoms, where in each case one or more non-adjacent CH2 groups may be replaced by SO, SO2, O, S and where one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms.
Furthermore, the following definitions of chemical groups apply for the purposes of the present application:
An aryl group in the sense of this invention contains 6 to 60 aromatic ring atoms, preferably 6 to 40 aromatic ring atoms, more preferably 6 to 20 aromatic ring atoms; a heteroaryl group in the sense of this invention contains 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, more preferably 5 to 20 aromatic ring atoms, at least one of which is a heteroatom. The heteroatoms are preferably selected from N, O and S. This represents the basic definition. If other preferences are indicated in the description of the present invention, for example with respect to the number of aromatic ring atoms or the heteroatoms present, these apply.
An aryl group or heteroaryl group here is taken to mean either a simple aromatic ring, i.e. benzene, or a simple heteroaromatic ring, for example pyridine, pyrimidine or thiophene, or a condensed (annellated) aromatic or heteroaromatic polycycle, for example naphthalene, phenanthrene, quinoline or carbazole. A condensed (annellated) aromatic or heteroaromatic polycycle in the sense of the present application consists of two or more simple aromatic or heteroaromatic rings condensed with one another.
An aryl or heteroaryl group, which may in each case be substituted by the above-mentioned radicals and which may be linked to the aromatic or heteroaromatic ring system via any desired positions, is taken to mean, in particular, groups derived from benzene, naphthalene,
anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benz- anthracene, benzophenanthrene, tetracene, pentacene, benzopyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzo- thiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, pheno- thiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthimidazole, phen- anthrimidazole, pyridimidazole, pyrazinimidazole, quinoxalinimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1 ,2-thiazole, 1 ,3- thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, pyrazine, phenazine, naphthyridine, azacarbazole, benzocarboline, phenan- throline, 1 ,2,3-triazole, 1 ,2,4-triazole, benzotriazole, 1 ,2,3-oxadiazole, 1 ,2,4-oxadiazole, 1 ,2,5-oxadiazole, 1 ,3,4-oxadiazole, 1 ,2,3-thiadiazole, 1 ,2,4-thiadiazole, 1 ,2,5-thiadiazole,
1.3.4-thiadiazole, 1 ,3,5-triazine, 1 ,2,4-triazine, 1 ,2,3-triazine, tetrazole, 1 ,2,4,5-tetrazine,
1.2.3.4-tetrazine, 1 ,2,3,5-tetrazine, purine, pteridine, indolizine and benzothiadiazole.
An aryloxy group in accordance with the definition of the present invention is taken to mean an aryl group, as defined above, which is bonded via an oxygen atom. An analogous definition applies to heteroaryloxy groups.
An aromatic ring system in the sense of this invention contains 6 to 60 C atoms in the ring system, preferably 6 to 40 C atoms, more preferably 6 to 20 C atoms. A heteroaromatic ring system in the sense of this invention contains 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, more preferably 5 to 20 aromatic ring atoms, at least one of which is a heteroatom. The heteroatoms are preferably selected from N, O and/or S. An aromatic or heteroaromatic ring system in the sense of this invention is intended to be taken to mean a system which does not necessarily contain only aryl or heteroaryl groups, but instead in which, in addition, a plurality of aryl or heteroaryl groups may be connected by a non-aromatic unit (preferably less than 10% of the atoms other than H), such as, for example, an sp3- hybridised C, Si, N or O atom, an sp2-hybridised C or N atom or an sp-hybridised C atom. Thus, for example, systems such as 9,9’-spirobifluorene, 9,9’-diarylfluorene, triarylamine, diaryl ether, stilbene, etc., are also intended to be taken to be aromatic ring systems in the sense of this invention, as are systems in which two or more aryl groups are connected, for example, by a linear or cyclic alkyl, alkenyl or alkynyl group or by a silyl group. Furthermore, systems in which two or more aryl or heteroaryl groups are linked to one another via single
bonds are also taken to be aromatic or heteroaromatic ring systems in the sense of this invention, such as, for example, systems such as biphenyl, terphenyl or diphenyltriazine.
An aromatic or heteroaromatic ring system having 5 - 60 aromatic ring atoms, which may in each case also be substituted by radicals as defined above and which may be linked to the aromatic or heteroaromatic group via any desired positions, is taken to mean, in particular, groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans- indenofluorene, truxene, isotruxene, spirotruxene, spiroisotruxene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzo- thiophene, pyrrole, indole, isoindole, carbazole, indolocarbazole, indenocarbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimi- dazole, naphthimidazole, phenanthrimidazole, pyridimidazole, pyrazinimidazole, quinoxalin- imidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxa- zole, 1 ,2-thiazole, 1 ,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1 ,5-diazaanthracene, 2,7-diazapyrene, 2,3-diazapyrene, 1 ,6-diazapyrene, 1 ,8-diazapyrene, 4,5-diazapyrene, 4,5,9, 10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorubin, naphthyridine, azacarbazole, benzo- carboline, phenanthroline, 1 ,2,3-triazole, 1 ,2,4-triazole, benzotriazole, 1 ,2,3-oxadiazole,
1.2.4-oxadiazole, 1 ,2,5-oxadiazole, 1 ,3,4-oxadiazole, 1 ,2,3-thiadiazole, 1 ,2,4-thiadiazole,
1.2.5-thiadiazole, 1 ,3,4-thiadiazole, 1 ,3,5-triazine, 1 ,2,4-triazine, 1 ,2,3-triazine, tetrazole,
1.2.4.5-tetrazine, 1 ,2,3,4-tetrazine, 1 ,2,3,5-tetrazine, purine, pteridine, indolizine and benzo- thiadiazole, or combinations of these groups.
For the purposes of the present invention, a straight-chain alkyl group having 1 to 40 C atoms or a branched or cyclic alkyl group having 3 to 40 C atoms or an alkenyl or alkynyl group having 2 to 40 C atoms, in which, in addition, individual H atoms or CH2 groups may be substituted by the groups mentioned above under the definition of the radicals, is preferably taken to mean the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-
trifluoroethyl, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl or octynyl. An alkoxy or thioalkyl group having 1 to 40 C atoms is preferably taken to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t- butoxy, n-pentoxy, s-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cyclo- heptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy, 2,2,2-tri- fluoroethoxy, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, n-pentylthio, s-pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoromethylthio, pentafluoro- ethylthio, 2,2,2-trifluoroethylthio, ethenylthio, propenylthio, butenylthio, pentenylthio, cyclo- pentenylthio, hexenylthio, cyclohexenylthio, heptenylthio, cycloheptenylthio, octenylthio, cyclooctenylthio, ethynylthio, propynylthio, butynylthio, pentynylthio, hexynylthio, heptynyl- thio or octynylthio.
The formulation that two radicals may form a ring with one another is, for the purposes of the present application, intended to be taken to mean, inter alia, that the two radicals are linked to one another by a chemical bond. This is illustrated by the following schemes:
Furthermore, however, the above-mentioned formulation is also intended to be taken to mean that, in the case where one of the two radicals represents hydrogen, the second radical is bonded at the position to which the hydrogen atom was bonded, with formation of a ring. This is illustrated by the following scheme:
Ri f i
When two radicals form a ring with one another, then it is preferred that the two radicals are adjacent radicals. Adjacent radicals in the sense of the present invention are radicals which are bonded to atoms which are linked directly to one another or which are bonded to the same atom.
In accordance with a preferred embodiment, the compound of formula (1) is selected from the compounds of formulae (1-1) to (1-4),
In accordance with a preferred embodiment, the group Ar1 of formula (1) is selected from the groups of formulae (Ar1-1) to (Ar1-5)
In accordance with a very preferred embodiment, the compound of formula (1) is selected from the compounds of formulae (1-1-1-1) to (1-4- 5-4),
In a preferred embodiment of the invention Q is C and Ar1 is a group of formulae (Ar1-1) to (Ar1-4) or Q is Ge or Si and Ar1 is a group of formula (Ar-4).
In a preferred embodiment of the invention X stand on each occurrence, identically or differently for CRX.
In a preferred embodiment of the invention X stand on each occurrence, identically or differently for CRX and Y stand on each occurrence, identically or differently for CRY. In this embodiment no X or Y is N.
In a preferred embodiment of the invention Y stand on each occurrence, identically or differently for CRY.
In a preferred embodiment the compound is a compound according to one of the formulae (1-1-1-1) to (1 -1-5-4) or (1-2-1-1) to (1-2-5-4).
Preferred embodiments of the compounds according to formulae (1-1-1-1) to (1-4- 5-4) are shown in the following table:
In a preferred embodiment the compound contains not more than two substituents R that are a group other than H, F, CN or D, preferably other than H or D.
In a preferred embodiment the compound contains not more than two substituents selected from Rx and/or RY are a group other than H, F, CN or D, preferably other than H or D.
In a preferred embodiment the compound is a compound according to one of the formulae (1-1-1-1) to (1 -1-5-4) or (1-2-1-1) to (1-2-5-4), preferably according to one of the formulae (1-1-1-1a) to (1-1-5-4a) or (1-2-1-1a) to (1-2-5-4a).
Preferably, R1, Rx, RY stand on each occurrence, identically or differently, for H, D, F, a straight-chain alkyl, alkoxy or thioalkyl group having 1 to 40, preferably 1 to 20, more preferably 1 to 10 C atoms or branched or a cyclic alkyl, alkoxy or thioalkyl group having 3 to 40, preferably 3 to 20, more preferably 3 to 10 C atoms, each of which may be substituted by one or more radicals R, where in each case one or more non-adjacent CH2 groups may be replaced by RC=CR, C=C, O or S and where one or more H atoms may be replaced by D or F, an aromatic or heteroaromatic ring system having 5 to 60, preferably 5
to 40, more preferably 5 to 30, particularly preferably 5 to 18 aromatic ring atoms, which may in each case be substituted by one or more radicals R.
More preferably, R1, Rx, RY stand on each occurrence, identically or differently, for H, D, F, a straight-chain alkyl group having 1 to 20, preferably 1 to 10, more preferably 1 to 6 C atoms or branched or a cyclic alkyl group having 3 to 20, preferably 3 to 10, more preferably 3 to 6 C atoms, each of which may be substituted by one or more radicals R, an aromatic or heteroaromatic ring system having 5 to 40, preferably 5 to 30, more preferably 5 to 18 aromatic ring atoms, which may in each case be substituted by one or more radicals R, where two radicals R1 and/or a radical R1 and a radical RY may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R.
Particularly preferably, R1, Rx, RY stand on each occurrence, identically or differently, for H, D, a straight-chain alkyl group having 1 to 10, preferably 1 to 6 C atoms or branched or a cyclic alkyl group having 3 to 10, preferably 3 to 6 C atoms, each of which may be substituted by one or more radicals R, or an aromatic or heteroaromatic ring system having 5 to 18 aromatic ring atoms, preferably 6 to 12 aromatic ring atoms, which may in each case be substituted by one or more radicals R, where two radicals R1 and/or a radical R1 and a radical RY may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R.
Very particularly preferably Rx, RY stand for H or D.
In the case of R1, Rx, RY standing for an aromatic or heteroaromatic ring system it is preferred that they are the same or different at each instance and selected from the groups of the following formulae Ar-1 to Ar-83:
Ar-67 Ar-68
where R is as defined above, the dotted bond represents the bond to corresponding carbon atom and, in addition:
Ar3 is the same or different at each instance and is a bivalent aromatic or heteroaromatic ring system which has 6 to 18 aromatic ring atoms and may be substituted in each case by one or more R radicals;
A1 is the same or different at each instance and is NR, O, S or C(R)2; n is 0 or 1 , where n = 0 means that no A1 group is bonded at this position and R radicals are bonded to the corresponding carbon atoms instead; m is 0 or 1 , where m = 0 means that the Ar3 group is absent and that the corresponding aromatic or heteroaromatic group is bonded directly to the carbon atom.
Particularly preferred Ar groups are Ar-1 , Ar-2, Ar-3, Ar-4, Ar-13 groups with A1 = O or S, m = 1 and Ar3 = para-phenylene, Ar-13 with m = 0 and A1 = C(CH3)2 or C(C6Hs)2, Ar-14 with m = 0 and A1 = C(CH3)2 or C(C6Hs)2, Ar-15 with A1 = N-phenyl, m = 1 and Ar3 = meta- or para- phenylene, Ar-16 with m = 0 and A1 = O, S, C(CH3)2 or C(C6Hs)2, Ar-43, Ar-45 and Ar-46, especially the following groups: Ar-1a, Ar-2a, Ar-3a, Ar-4a, Ar-13a with A1 = O or S, Ar-13b with A1 = C(CH3)2 or C(C6H5)2, Ar-14a with A1 = C(CH3)2 or C(C6H5)2, Ar-15a, Ar-15b, Ar- 16a with A1 = O, S, C(CH3)2 or C(C6H5)2, Ar-43a, Ar-45a and Ar-46a,
where the symbols used have the definitions given above.
In a preferred embodiment R1 stands on each occurrence identically or differently for a straight-chain alkyl group having 1 to 20, preferably 1 to 10, more preferably 1 to 6 C atoms or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, preferably 5 to 18, more preferably 6 to 12 aromatic ring atoms, which may in each case be sub- stituted by one or more radicals R, where two radicals R1 may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R.
In a preferred embodiment R1 stands on each occurrence identically or differently for a straight-chain alkyl group having 1 to 20, preferably 1 to 10, more preferably 1 to 6 C atoms or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, preferably 5 to 18, more preferably 6 to 12 aromatic ring atoms, which may in each case be sub- stituted by one or more radicals R, where two radicals R1 may form an aliphatic, aromatic or heteroaromatic ring system together, which may be substituted by one or more radicals R, preferably two racidals R1 may form an aromatic or heteroaromatic ring system via at least one single bond.
In a preferred embodiment R1 is selected from the groups according to CR3, CR2CR3, Ar-1, Ar-2, Ar-3, Ar-4, preferably Ar-1 and CR3, wherein two R1 may be connected via a single bond.
In accordance with a very preferred embodiment, the compound of formula (1) is selected from the compounds of formulae (1 -1 - 1 - 1 a) to (1-4-6-4a),
-ML-
-90 k-
Where in formulae (1-1 -1-1 a) to (1-4-5-4a): p, q are selected, identically or differently, from 0, 1 , 2, 3 and 4; and r,s are selected, identically or differently, from 0, 1 , 2, 3, 4 and 5.
The present invention therefore further provides a process for preparing the compounds of
35 the invention, characterized by the following steps:
(1) synthesizing the base skeleton of the compound of the formula (1) containing a reactive leaving group or H in place of the Ar1 group, the reactive leaving group preferably selected from boronic acid, boronic ester, Cl, Br, I, triflate, tosylate or mesylate;
(2) introducing the Ar1 group by a coupling reaction.
The present invention furthermore provides a composition comprising a material selected from compounds of the formula (1) as defined above and a material selected from electron- transporting host materials that is preferably selected from the group of the triazines, pyrimidines, quinazolines, quinoxalines and lactams, or derivatives of these structures.
Preferred triazine, pyrimidine, quinazoline or quinoxaline derivatives that can be used as a mixture together with the compounds of the invention are the compounds of the following formulae (e-1), (e-2), (e-3) and (e-4):
where R has the meanings given above. R is preferably the same or different at each instance and is H or an aromatic or heteroaromatic ring system which has 6 to 30 aromatic ring atoms and which may be substituted by one or more R1 radicals.
Preference is given to the compounds of the following formulae (e-1 a) to (e-4a):
Particular preference is given to the triazine derivatives of the formula (e-1) or (e-1a) and the quinoxaline derivatives of the formula (e-4) or (e-4a), especially the triazine derivatives of the formula (e-1) or (e-1 a).
In a preferred embodiment of the invention, Ar in the formulae (e-1 a), (e-2a), (e-3a) and (e- 4a) is the same or different at each instance and is an aromatic or heteroaromatic ring system which has 6 to 30 aromatic ring atoms, especially 6 to 24 aromatic ring atoms, and may be substituted by one or more R radicals. Suitable aromatic or heteroaromatic ring systems Ar here are the same as set out above as embodiments for Ar, especially the structures Ar-1 to Ar-83.
Examples of suitable triazine and pyrimidine compounds that may be used as matrix materials together with the compounds of the invention are the compounds depicted in the following table:
Examples of suitable quinazoline and quinoxaline derivatives are the structures depicted in the following table:
Examples of suitable lactams are the structures depicted in the following table:
Other examples of suitable matrix materials that can be used together with the compounds of the invention are the compounds depicted in the following table:
Preferably, the composition comprises a first host material selected from compounds of the formula (1) as defined above, a second host material selected from electron-transporting host materials and a third compound selected from phosphorescent emitters, fluorescent emitters and emitters that exhibit TADF (thermally activated delayed fluorescence).
In accordance with a preferred embodiment, the third compound is selected from phosphorescent emitters. Phosphorescence in the context of this invention is understood to mean luminescence from an excited state having higher spin multiplicity, i.e. a spin state > 1, especially from an excited triplet state. In the context of this application, all luminescent complexes with transition metals or lanthanides, especially all iridium, platinum and copper complexes, shall be regarded as phosphorescent emitters.
Suitable phosphorescent compounds (= triplet emitters) are especially compounds which, when suitably excited, emit light, preferably in the visible region, and also contain at least one atom of atomic number greater than 20, preferably greater than 38 and less than 84, more preferably greater than 56 and less than 80, especially a metal having this atomic number. Preferred phosphorescence emitters used are compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, especially compounds containing iridium or platinum.
Examples of the emitters described above can be found in applications WO 00/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645, EP 1191613, EP 1191612, EP 1191614, WO 05/033244, WO 05/019373, US 2005/0258742, WO 2009/146770, WO 2010/015307, WO 2010/031485, WO 2010/054731, WO 2010/054728, WO 2010/086089, WO 2010/099852, WO 2010/102709, WO 2011/032626, WO 2011/066898, WO 2011/157339, WO 2012/007086, WO 2014/008982, WO 2014/023377, WO 2014/094961, WO 2014/094960, WO 2015/036074, WO 2015/104045, WO 2015/117718, WO 2016/015815, WO 2016/124304, WO 2017/032439, WO 2018/011186 and WO 2018/041769, WO 2019/020538, WO 2018/178001, WO 2019/115423 or WO 2019/158453. In general, all phosphorescent complexes as used for phosphorescent OLEDs according to the prior art and as known to those skilled in the art in the field of organic electroluminescence are suitable, and the person skilled in the art will be able to use further phosphorescent complexes without exercising inventive skill.
In accordance with another preferred embodiment, the third compound is selected from emitters which exhibit thermally activated delayed fluorescence (TADF emitters) (e.g. H. Uoyarna et al., Nature 2012, vol. 492, 234). These emitters are organic materials in which the energy gap between the lowest triplet state Ti and the first excited singlet state Si is sufficiently small that the Si state is thermally accessible from the Ti state. The TADF emitter is preferably an aromatic compound having both donor and acceptor substituents, with only slight spatial overlap between the LIIMO and the HOMO of the compound. What is understood by donor and acceptor substituents is known in principle to those skilled in the art. Suitable donor substituents are especially diaryl- or -heteroarylamino groups and
carbazole groups or carbazole derivatives, each preferably bonded to the aromatic compound via N. These groups may also have further substitution. Suitable acceptor substituents are especially cyano groups, but also, for example, electron-deficient heteroaryl groups which may also have further substitution, for example substituted or unsubstituted triazine groups.
The general art knowledge of the person skilled in the art includes knowledge of which materials are generally suitable as TADF compounds. The following references disclose, by way of example, materials that are potentially suitable as TADF compounds:
Tanaka et al., Chemistry of Materials 25(18), 3766 (2013).
Lee et al., Journal of Materials Chemistry C 1(30), 4599 (2013).
Zhang et al., Nature Photonics advance online publication, 1 (2014), doi: 10.1038/nphoton.2014.12.
Serevicius et al., Physical Chemistry Chemical Physics 15(38), 15850 (2013).
Li et al., Advanced Materials 25(24), 3319 (2013).
- Youn Lee et al., Applied Physics Letters 101(9), 093306 (2012).
Nishimoto et al., Materials Horizons 1, 264 (2014), doi: 10.1039/C3MH00079F. Valchanov et al., Organic Electronics, 14(11), 2727 (2013).
Nasu et al., ChemComm, 49, 10385 (2013).
In addition, the following patent applications disclose potential TADF compounds: WO 2013/154064, WO 2013/133359, WO 2013/161437, WO 2013/081088, WO 2013/081088, WO 2013/011954, JP 2013/116975 and US 2012/0241732.
In addition, the person skilled in the art is able to infer design principles for TADF compounds from these publications. For example, Valchanov et al. show how the color of TADF compounds can be adjusted.
Still in accordance with another preferred embodiment, the third compound is selected from fluorescent emitters. Preferred fluorescent emitters are aromatic anthracenamines, aro- matic anthracenediamines, aromatic pyrenamines, aromatic pyrenediamines, aromatic chrysenamines or aromatic chrysenediamines. An aromatic anthracenamine is taken to mean a compound in which one diarylamino group is bonded directly to an anthracene group, preferably in the 9-position. An aromatic anthracenediamine is taken to mean a com- pound in which two diarylamino groups are bonded directly to an anthracene group, preferably in the 9,10-position. Aromatic pyrenamines, pyrenediamines, chrysenamines and chrysenediamines are defined analogously thereto, where the diarylamino groups are
preferably bonded to the pyrene in the 1 -position or in the 1,6-position. Further preferred emitters are indenofluorenamines or indenofluorenediamines, for example in accordance with WO 2006/108497 or WO 2006/122630, benzoindenofluorenamines or benzoindenofluorenediamines, for example in accordance with WO 2008/006449, and dibenzoindenofluorenamines or dibenzoindenofluorenediamines, for example in accordance with WO 2007/140847, and the indenofluorene derivatives containing con- densed aryl groups which are disclosed in WO 2010/012328. Still further preferred emitters are benzanthracene derivatives as disclosed in WO 2015/158409, anthracene derivatives as disclosed in WO 2017/036573, fluorene dimers connected via heteroaryl groups like in WO 2016/150544 or phenoxazine derivatives as disclosed in WO 2017/028940 and WO 2017/028941. Preference is likewise given to the pyrenarylamines disclosed in WO 2012/048780 and WO 2013/185871. Preference is likewise given to the benzoindenofluorenamines disclosed in WO 2014/037077, the benzofluorenamines disclosed in WO 2014/106522 and the indenofluorenes disclosed in WO 2014/111269 or WO 2017/036574, WO 2018/007421. Also preferred are the emitters comprising dibenzofuran or indenodibenzofuran moieties as disclosed in WO 2018/095888, WO 2018/095940, WO 2019/076789, WO 2019/170572 as well as in WO 2020/043657, WO 2020/043646 and WO/2020/043640. Preference is likewise given to boron derivatives as disclosed, for example, in WO 2015/102118, CN108409769, CN107266484, WO2017195669, US2018069182 as well as in WO 2020/208051 , W02021/058406, and WO 2021/094269.
In accordance with another preferred embodiment, the composition comprises a first host material selected from compounds of the formula (1) as defined above, a second host material selected from hole-transporting host materials, a third compound selected from phosphorescent emitters and emitters that exhibit TADF (thermally activated delayed fluorescence) and a fourth compound selected from phosphorescent emitters and fluorescent emitters.
In the further layers of the organic electroluminescent device of the invention, it is possible to use any materials as typically used according to the prior art. The person skilled in the art will therefore be able, without exercising inventive skill, to use any materials known for organic electroluminescent devices in combination with the compounds of formula (1) or the above-recited preferred embodiments.
The compositions may also comprise further organic or inorganic compounds which are likewise used in the electronic device like, for example, further emitters or further host materials.
The compound of formula (1) or the composition comprising a compound of formula (1) may be processed by vapour deposition or from solution. If the compositions are applied from solution, formulations of the composition of the invention comprising at least one further solvent are required. These formulations may, for example, be solutions, dispersions or emulsions. For this purpose, it may be preferable to use mixtures of two or more solvents.
The present invention therefore further provides a formulation comprising a compound of formula (1) or a composition comprising a compound of formula (1) and at least one solvent.
Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP, chlorobenzene, dioxane, phenoxytoluene, especially 3-phenoxytoluene, (-)-fenchone, 1 , 2,3,5- tetramethylbenzene, 1 ,2,4,5-tetramethylbenzene, 1 -methylnaphthalene, 2- methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole,
3.4-dimethylanisole, 3,5-dimethylanisole, acetophenone, a-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, NMP, p-cymene, phenetole,
1.4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, hexamethylindane or mixtures of these solvents.
The present invention also provides for the use of the compound of formula (1) or of compositions comprising the compound of formula (1) in an organic electronic device, preferably in an emitting layer and/or in an electron-transporting layer.
The organic electronic device is preferably selected from organic integrated circuits (OlCs), organic field-effect transistors (OFETs), organic thin-film transistors (OTFTs), organic electroluminescent devices, organic solar cells (OSCs), organic optical detectors and organic photoreceptors, particular preference being given to organic electroluminescent devices.
Very particularly preferred organic electroluminescent devices containing at least one compound of the formula (1), as described above or described as preferred, are organic light-emitting transistors (OLETs), organic field-quench devices (OFQDs), organic light- emitting electrochemical cells (OLECs, LECs, LEECs), organic laser diodes (O-lasers) and organic light-emitting diodes (OLEDs); OLECs and OLEDs are especially preferred and OLEDs are the most preferred.
Preferably, the compound of formula (1) as described above or described as preferred is used in a layer having an electron-transporting function in an electronic device. The layer is preferably an electron injection layer (EIL), an electron transport layer (ETL), a hole blocker layer (HBL) and/or an emission layer (EML), more preferably an ETL, EIL and/or an EML. Most preferably, the compound of formula (1) or the composition is used in an EML as an host material in combination with a electron-transporting host material.
Therefore, the present invention further provides an organic electronic device which is especially selected from one of the aforementioned electronic devices and which comprises the compound of formula (1) or compositions comprising the compound of formula (1), as described above or described as preferred, preferably in an emission layer (EML), in an electron transport layer (ETL), in an electron injection layer (EIL) and/or in a hole blocker layer (HBL), very preferably in an EML, EIL and/or ETL and most preferably in an EML.
In a particularly preferred embodiment of the present invention, the electronic device is an organic electroluminescent device, most preferably an organic light-emitting diode (OLED), containing the compound of formula (1) or a composition comprising the compound of formula (1) in the emission layer (EML).
In a particularly preferred embodiment of the present invention, the organic electroluminescent device is therefore one comprising an anode, a cathode and at least
one organic layer comprising at least one light-emitting layer, wherein the at least one light- emitting layer contains at least one compound of the formula (1) or a composition comprising a compound of formula (1) as described above.
The light-emitting layer in the device of the invention, as described above, contains preferably between 99.9% and 1% by volume, further preferably between 99% and 10% by volume, especially preferably between 98% and 40% by volume, very especially preferably between 97% and 50% by volume, of host material composed of at least one compound of the formula (1) or composed of at least one a first host material selected from compounds of the formula (1) and a second host material selected from electron-transporting host materials as described above, based on the overall composition of emitter and host material. Correspondingly, the light-emitting layer in the device of the invention preferably contains between 0.1% and 99% by volume, further preferably between 1% and 90% by volume, more preferably between 2% and 40% by volume, most preferably between 3% and 20% by volume, of the emitter based on the overall composition of the light-emitting layer composed of emitter and host material. If the compounds are processed from solution, preference is given to using the corresponding amounts in % by weight rather than the above-specified amounts in % by volume.
The light-emitting layer in the device of the invention, as described above, preferably contains the host material of the formula (1), preferably in combination with a host material selected from electron-transporting host materials, in a percentage by volume ratio between 3:1 and 1 :3, preferably between 1 :2.5 and 1 :1 , more preferably between 1 :2 and 1 :1. If the compounds are processed from solution, preference is given to using the corresponding ratio in % by weight rather than the above-specified ratio in % by volume.
Apart from the cathode, anode and the layer comprising the composition of the invention, an electronic device may comprise further layers. These are selected, for example, from in each case one or more hole injection layers, hole transport layers, hole blocker layers, light- emitting layers, electron transport layers, electron injection layers, electron blocker layers, exciton blocker layers, interlayers, charge generation layers (IDMC 2003, Taiwan; Session 21 OLED (5), T. Matsumoto, T. Nakada, J. Endo, K. Mori, N. Kawamura, A. Yokoi, J. Kido, Multiphoton Organic EL Device Having Charge Generation Layer) and/or organic or
inorganic p/n junctions. However, it should be pointed out that not necessarily every one of these layers needs to be present.
The sequence of layers in an organic electroluminescent device is preferably as follows: anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode.
The sequence of the layers is a preferred sequence.
At the same time, it should be pointed out again that not all the layers mentioned need be present and/or that further layers may additionally be present.
An organic electroluminescent device of the invention may contain two or more light- emitting layers. According to the invention, at least one of the light-emitting layers contains at least one compound of the formula (1) and compositions comprising a compound of formula (1) as described above. More preferably, these emission layers in this case have several emission maxima between 380 nm and 750 nm overall, such that the overall result is white emission; in other words, various emitting compounds which may fluoresce or phosphoresce and which emit blue or yellow or orange or red light are used in the light- emitting layers. Especially preferred are three-layer systems, i.e. systems having three light-emitting layers, where the three layers show blue, green and orange or red emission (for the basic construction see, for example, WO 2005/011013). It should be noted that, for the production of white light, rather than a plurality of colour-emitting emitter compounds, an emitter compound used individually which emits over a broad wavelength range may also be suitable.
Suitable charge transport materials as usable in the hole injection or hole transport layer or electron blocker layer or in the electron transport layer of the organic electroluminescent device of the invention are, for example, the compounds disclosed in Y. Shirota et al., Chem. Rev. 2007, 107(4), 953-1010, or other materials as used in these layers according to the prior art.
Materials used for the electron transport layer may be any materials as used according to the prior art as electron transport materials in the electron transport layer. Especially suitable are aluminium complexes, for example Alqs, zirconium complexes, for example
Zrq4, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, oxadiazole derivatives, aromatic ketones, lactams, boranes, diazaphosphole derivatives and phosphine oxide derivatives. Further suitable materials are derivatives of the above-mentioned compounds as disclosed in JP 2000/053957, WO 2003/060956, WO 2004/028217, WO 2004/080975 and WO 2010/072300.
Preferred hole transport materials are especially materials which can be used in a hole transport, hole injection or electron blocker layer, such as indenofluoreneamine derivatives (for example according to WO 06/122630 or WO 06/100896), the amine derivatives disclosed in EP 1661888, hexaazatriphenylene derivatives (for example according to WO 01/049806), amine derivatives having fused aromatic systems (for example according to US 5,061,569), the amine derivatives disclosed in WO 95/09147, monobenzoindenofluoreneamines (for example according to WO 08/006449), dibenzoindenofluoreneamines (for example according to WO 07/140847), spirobifluoreneamines (for example according to WO 2012/034627 or the as yet unpublished EP 12000929.5), fluoreneamines (for example according to WO 2014/015937, WO 2014/015938 and WO 2014/015935), spirodibenzopyranamines (for example according to WO 2013/083216) and dihydroacridine derivatives (for example WO 2012/150001).
Preferred cathodes of electronic devices are metals having a low work function, metal alloys or multilayer structures composed of various metals, for example alkaline earth metals, alkali metals, main group metals or lanthanoids (e.g. Ca, Ba, Mg, Al, In, Mg, Yb, Sm, etc.). Additionally suitable are alloys composed of an alkali metal or alkaline earth metal and silver, for example an alloy composed of magnesium and silver. In the case of multilayer structures, in addition to the metals mentioned, it is also possible to use further metals having a relatively high work function, for example Ag or Al, in which case combinations of the metals such as Ca/Ag, Mg/Ag or Ba/Ag, for example, are generally used. It may also be preferable to introduce a thin interlayer of a material having a high dielectric constant between a metallic cathode and the organic semiconductor. Examples of useful materials for this purpose are alkali metal or alkaline earth metal fluorides, but also the corresponding oxides or carbonates (e.g. Li F, U2O, BaF2, MgO, NaF, CsF, CS2CO3,
etc.). It is also possible to use lithium quinolinate (LiQ) for this purpose. The layer thickness of this layer is preferably between 0.5 and 5 nm.
Preferred anodes are materials having a high work function. Preferably, the anode has a work function of greater than 4.5 eV versus vacuum. Firstly, metals having a high redox potential are suitable for this purpose, for example Ag, Pt or Au. Secondly, metal/metal oxide electrodes (e.g. Al/N i/N iOx, AI/PtOx) may also be preferred. For some applications, at least one of the electrodes has to be transparent or partly transparent in order to enable either the irradiation of the organic material (organic solar cell) or the emission of light (OLED, O-I-ASER). Preferred anode materials here are conductive mixed metal oxides. Particular preference is given to indium tin oxide (ITO) or indium zinc oxide (IZO). Preference is further given to conductive doped organic materials, especially conductive doped polymers. In addition, the anode may also consist of two or more layers, for example of an inner layer of ITO and an outer layer of a metal oxide, preferably tungsten oxide, molybdenum oxide or vanadium oxide.
The organic electronic device, in the course of production, is appropriately (according to the application) structured, contact-connected and finally sealed, since the lifetime of the devices of the invention is shortened in the presence of water and/or air.
In a further preferred embodiment, the organic electronic device comprising the composition of the invention is characterized in that one or more organic layers comprising the composition of the invention are coated by a sublimation method. In this case, the materials are applied by vapour deposition in vacuum sublimation systems at an initial pressure of less than 10'5 mbar, preferably less than 10'6 mbar. In this case, however, it is also possible that the initial pressure is even lower, for example less than 10'7 mbar.
Preference is likewise given to an organic electroluminescent device, characterized in that one or more layers are coated by the OVPD (organic vapour phase deposition) method or with the aid of a carrier gas sublimation. In this case, the materials are applied at a pressure between 10'5 mbar and 1 bar. A special case of this method is the OVJP (organic vapour jet printing) method, in which the materials are applied directly by a nozzle and thus structured (for example, M. S. Arnold et al., Appl. Phys. Lett. 2008, 92, 053301).
Preference is additionally given to an organic electroluminescent device, characterized in that one or more organic layers comprising the composition of the invention are produced from solution, for example by spin-coating, or by any printing method, for example screen printing, flexographic printing, nozzle printing or offset printing, but more preferably LITI (light-induced thermal imaging, thermal transfer printing) or inkjet printing. For this purpose, soluble compounds of the components of the composition of the invention are needed. High solubility can be achieved by suitable substitution of the corresponding compounds. Processing from solution has the advantage that the layer comprising the composition of the invention can be applied in a very simple and inexpensive manner. This technique is especially suitable for the mass production of organic electronic devices.
In addition, hybrid methods are possible, in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapour deposition.
These methods are known in general terms to those skilled in the art and can be applied to organic electroluminescent devices.
The invention therefore further provides a process for producing an organic electronic device comprising a composition of the invention as described above or described as preferred, characterized in that at least one organic layer comprising a composition of the invention is applied by gas phase deposition, especially by a sublimation method and/or by an OVPD (organic vapour phase deposition) method and/or with the aid of carrier gas sublimation, or from solution, especially by spin-coating or by a printing method.
In the production of an organic electronic device by means of gas phase deposition, there are two methods in principle by which an organic layer which is to comprise the composition of the invention and which may comprise multiple different constituents can be applied, or applied by vapour deposition, to any substrate. Firstly, the materials used can each be initially charged in a material source and ultimately evaporated from the different material sources ("co-evaporation"). Secondly, the various materials can be premixed (premix systems) and the mixture can be initially charged in a single material source from which it is ultimately evaporated ("premix evaporation"). In this way, it is possible in a simple and rapid manner to achieve the vapour deposition of a layer with homogeneous distribution of the components without a need for precise actuation of a multitude of material sources.
The invention accordingly further provides a process characterized in that the at least one compound of the formula (1) as described above or described as preferred and the compositions comprising the compound of formula (1) as described above or described as preferred are deposited from the gas phase successively or simultaneously from at least two material sources, optionally with other materials as described above or described as preferred, and form the organic layer.
The invention accordingly further provides a process characterized in that the composition of the invention as described above or described as preferred is utilized as material source for the gas phase deposition of the host system and, optionally together with further materials, forms the organic layer.
The invention further provides a process for producing an organic electronic device comprising a composition of the invention as described above or described as preferred, characterized in that the formulation of the invention as described above is used to apply the organic layer.
It should be pointed out that variations of the embodiments described in the present invention are covered by the scope of this invention. Any feature disclosed in the present invention may, unless this is explicitly ruled out, be exchanged for alternative features which serve the same purpose or an equivalent or similar purpose. Any feature disclosed in the present invention, unless stated otherwise, should therefore be considered as an example from a generic series or as an equivalent or similar feature.
All features of the present invention may be combined with one another in any manner, unless particular features and/or steps are mutually exclusive. This is especially true of preferred features of the present invention. Equally, features of non-essential combinations may be used separately (and not in combination).
The technical teaching disclosed with the present invention may be abstracted and combined with other examples. The invention is illustrated in more detail by the examples which follow, without any intention of restricting it thereby.
Synthesis examples
CAS: 1537905-39-7
5-(9H-carbazol-3-yl)-5H-benzo[d]benzo[4,5]imidazo[1 ,2-a]imidazole (CAS: 1537905-39-7) is synthesized in analogy to WO2014009317A1.
Example 1 :
5-fluoro-9,9'-spirobi[fluorene] (25.12 g; 72.80 mmol; 1.00 eq.), 5-(9H-carbazol-3-yl)-5H- benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (34.07 g; 87.36 mmol; 1.20 eq.) and Cesiumcarbonate (47.92 g; 145.60 mmol; 2.00 eq.) were added to 800 ml Dimethylacetamide and stirred under nitrogen for 30 min. After this it was heated for 48 h to 150°C. After cooling to room temperature, the solvent was distilled off and the residue was taken up in dichloromethane and water. The water phase was extracted twice with dichloromethane. After combining the organic phases, the mixture was washed with brine and dried with sodium sulfate. After evaporation of the solvent the crude product was chromatographically purified resulting in 49 g of final product (yield 98%).
The following molecules can be synthesized in the same way by changing the starting materials:
4-Fluoro-9,9-dimethyl-9H-fluorene (CAS: 2420524-96-3) is synthesized by the following reaction sequence:
CAS: 2420524-96-3 a) Suzuki reaction: Methyl 2-brom benzoate 99% (50.0 g; 230 mmol; 1.0 eq.), 2- fluorophenylboronic acid (32.3 g; 230 mmol; 1.0 eq.) and K2CO3 (63.6 g; 460 mmol; 2.0 eq.) are suspended in acetonitrile (750 ml) and ethanol (500 ml) under argon.
Bis(triphenylphosphin)Pd(ll) chloride (3.2 g; 4.6 mmol; 0.02 eq.) are added and the reaction mixture is heated under reflux for 20 hrs. After cooling to room temperature the mixture is poured onto water and extracted with ethyl acetate. The combined organic layers are dried over Na2SC>4 and the solvent is removed in vacuo. The crude product is purified via silica column chromatography and methyl 2'-fluoro-[1 ,1'-biphenyl]-2-carboxylate (47 g, 87%) is obtained as colourless oil. b) Grignard reaction: Cerium(lll) chloride (5.6 g; 22.6 mmol; 1.05 eq.) are heated up to 80 °C under argon for 1 hour. After cooling to room temperature methyl 2'-fluoro-[1 ,1'- biphenyl]-2-carboxylate (5.0 g; 21.5 mmol; 1.0 eq.) and THF (165 ml) are added. The reaction mixture is cooled to 2 °C and methylmagnesiumchlorid 3.0M in THF (21.5 ml; 64 mmol; 3.0 eq.) are added dropwise. Stirring is continued at room temperature over night. The mixture is poured into aqueous ammonia solution and it is extracted with ethyl acetate.
The combined organic layers are dried over Na2SC>4 and the solvent is removed in vacuo. Crude 2-{2'-fluoro-[1,1'-biphenyl]-2-yl}propan-2-ol (6.5 g) is obtained as yellow oil. c) Condensation: 2-{2'-fluoro-[1,1'-biphenyl]-2-yl}propan-2-ol (43.7 g; 185 mmol; 1.0 eq.) and Amberlyst 15 (17.8 g; 185 mmol; 1.0 eq.) are dissolved in toluene (1.5 I) and the reaction mixture is stirred under reflux for 48 hrs. After cooling to room temperature the amberlyst is filtered off and the solvent is removed in vacuo. The crude product is dissolved in heptane and filtered over silica and the solvent is removed in vacuo. 4-Fluoro-9,9- dimethyl-9H-fluorene (35.5 g, 89%) is obtained as colourless crystals.
Example 3:
3-(Bromophenyl)triphenylsilane (32.3 g; 77.3 mmol; 1.10 eq.), 5-(9H-carbazol-3-yl)-5H- benzo[d]benzo[4,5]imidazo[1,2-a]imidazole (19.4 g; 50.6 mmol; 0.72 eq.), K3PO4 (46.2 g; 211 mmol; 3,0 eq.) and Cul (4.0 g; 21.1 mmol; 0,30 eq.) are added to 1 ,4-dioxane (500 ml) and trans-1,2-diaminocyclohexane (DACH) (85 ml; 703 mmol; 10,00 eq.) and the suspension is degassed under argon. It is then heated to 100 °C for 2 days. After cooling to room temperature the reaction mixture is poured onto 500 ml aqueous ammonia (25%) and stirring is continued for 2 hrs. The product is extracted with toluene. The volumne of the solution is reduced and the resulting precipitate is collected and washed with methanol. The crude product is recrystallized from toluene to give 27 g (36 mmol, 52%) of the product as white solid.
Fabrication of OLEDs
Fabrication of vapor processed OLED devices
The manufacturing of the OLED devices is performed accordingly to WO 04/058911 with adapted film thicknesses and layer sequences. The following examples V1 , E1 and E2 show data of OLED devices.
Glass plates with structured ITO (50 nm, indium tin oxide) are pre-treated with an oxygen plasma, followed by an argon plasma. The pre-treated glass plates form the substrates on which the OLED devices are fabricated.
The OLED devices have in principle the following layer structure:
Substrate,
- ITO (50 nm),
Hole injection layer (HIL)
Hole transporting layer (HTL), Electron blocking layer (EBL), Emissive layer (EML), Hole blocking layer (HBL), Electron transporting layer (ETL), Electron injection layer (EIL), Cathode.
The cathode is formed by an aluminium layer with a thickness of 100 nm. The detailed stack sequence is shown in table A. The materials used for the OLED fabrication are presented in table B.
All materials are applied by thermal vapour deposition in a vacuum chamber. The emission layer here always consists of at least one matrix material and one phosphorescent material. The phosphorescent material is mixed with the matrix material or matrix materials in a certain proportion by volume by co-evaporation. An expression such as HH:EH:D (42%:43%:15%) here means that material HH is present in the layer in a proportion by volume of 42%, material EH is present in the layer in a proportion by volume of 43% and material D is present in the layer in a proportion by volume of 15%. Analogously, the electron-transport layer and hole-injection layer may also consist of a mixture of two or more materials.
The OLED devices are characterised by standard methods. For this purpose, the electroluminescence spectra and the external quantum efficiency (EQE, measured in %)
are determined from current/voltage/luminance characteristic lines (IUL characteristic lines) assuming a Lambertian emission profile. The electroluminescence (EL) spectra are recorded at a luminous density of 1000 cd/m2 and the CIE 1931 x and y coordinates are then calculated from the EL spectrum. U is defined as the voltage, which is required for a current density of 10 mA/cm2. The parameter EQE represents the external quantum efficiency at a current density of 10 mA/cm2. The lifetime LT90 is defined as the time after which the luminance drops from the starting luminance to a proportion of 90% of the starting luminance in the course of operation with a constant current density of 5 mA/cm2. The device data of various OLED devices are summarized in table A and table C. The example V1 represents a comparative example according to the state of the art. The examples E1 and E2 show data of inventive OLED devices that use an Ir-complex as emitter. The examples E3, E4, and E5 show data of inventive OLED devices that use an Pt-complex as emitter.
In the following section several examples are described in more detail to show the advantages of the inventive OLED devices.
Use of inventive compounds as host material in fluorescent OLEDs
The inventive compounds are especially suitable as a host (matrix) when blended with an electron-conducting host material and a phosphorescent emitter to form the emissive layer of a phosphorescent blue OLED device. The representative examples use HH1, HH2, and HH3 as host materials. Moreover, in the given examples E1 - E5 in table A and C the host compounds HH1, HH2, and HH3 can be exchanged by the compound HH4.
A comparative compound for the state of the art is represented by StA (structures see table B). The use of the inventive compound as a host (matrix) in a phosphorescent blue OLED device results in excellent device data, especially with respect to lifetime LT90 when compared to the state of the art. This technical advantage is apparent when examples E1 and E2 are compared to V1 in table A. Here, the inventive host compounds HH1 and HH2 in E1 and E2 can also be exchanged with the inventive compound HH4.
The use of the inventive compounds as a host (matrix) in a phosphorescent blue OLED device that incorporate a Pt-complex as emitter results in excellent device data, especially with respect to lifetime LT90. This is apparent in the examples E3 and E4 in table C, where
HTM2 is selected from a fluorenamine compound. Moreover, the inventive host compounds HH2 and HH3 in E3 and E4 can also be exchanged with the inventive compound HH4.
Moreover, the use of the inventive compounds as an electron blocking material in the EBL in a phosphorescent blue OLED results in excellent device data, especially with respect to lifetime LT90 and operational voltage II. This is apparent when comparing example E5 and E4 in table C, where HTM2 is selected from fluorenamine compounds. Here, the inventive host compound HH3 in E4 and E5 can also be exchanged with the inventive compound HH4.
Claims
(1) synthesizing the base skeleton of the compound of the formula (1) containing a reactive leaving group or H in place of the Ar1 group;
(2) introducing the Ar1 group by a coupling reaction. Formulation comprising at least one compound according to one or more of Claims 1 to 9 and at least one solvent. Use of a compound according to one or more of Claims 1 to 9 in an electronic device. Electronic device comprising at least one compound according to one or more of Claims 1 to 9. Electronic device according to Claim 13 which is an organic electroluminescent device, characterized in that the compound according to one or more of Claims 1 to 9 is used in an emitting layer in combination with at least one phosphorescent emitter. Electronic device according to Claim 14, characterized in that the emitting layer contains at least one further material selected from the compounds of the formulae (e- 1), (e-2), (e-3) and (e-4)
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