CN117203184A - Compound for organic electric element, organic electric element using same, and electronic device using same - Google Patents
Compound for organic electric element, organic electric element using same, and electronic device using same Download PDFInfo
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- CN117203184A CN117203184A CN202280029789.6A CN202280029789A CN117203184A CN 117203184 A CN117203184 A CN 117203184A CN 202280029789 A CN202280029789 A CN 202280029789A CN 117203184 A CN117203184 A CN 117203184A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 96
- 239000000126 substance Substances 0.000 claims abstract description 97
- 239000012044 organic layer Substances 0.000 claims abstract description 36
- 239000010410 layer Substances 0.000 claims description 189
- 125000003118 aryl group Chemical group 0.000 claims description 68
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 125000000623 heterocyclic group Chemical group 0.000 claims description 54
- 229910052757 nitrogen Inorganic materials 0.000 claims description 48
- 229910052717 sulfur Inorganic materials 0.000 claims description 40
- 229910052760 oxygen Inorganic materials 0.000 claims description 39
- 125000005842 heteroatom Chemical group 0.000 claims description 37
- 125000001931 aliphatic group Chemical group 0.000 claims description 36
- 125000004122 cyclic group Chemical group 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- -1 aliphatic cyclic Chemical group 0.000 claims description 27
- 125000003342 alkenyl group Chemical group 0.000 claims description 26
- 125000000304 alkynyl group Chemical group 0.000 claims description 26
- 125000004104 aryloxy group Chemical group 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 125000005567 fluorenylene group Chemical group 0.000 claims description 21
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
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- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 12
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- 125000003277 amino group Chemical group 0.000 description 15
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- 125000005647 linker group Chemical group 0.000 description 11
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 8
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
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- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
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- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- QFPVHUJPACOOEB-UHFFFAOYSA-N 9-naphthalen-2-yl-9-phenylfluorene Chemical compound c1ccc(cc1)C1(c2ccccc2-c2ccccc12)c1ccc2ccccc2c1 QFPVHUJPACOOEB-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
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- 125000004429 atom Chemical group 0.000 description 3
- YUFRAQHYKKPYLH-UHFFFAOYSA-N benzo[f]quinoxaline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=N1 YUFRAQHYKKPYLH-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 125000005562 phenanthrylene group Chemical group 0.000 description 3
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- 229910002027 silica gel Inorganic materials 0.000 description 3
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- 101150075118 sub1 gene Proteins 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 2
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- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 2
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
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- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- FBVBNCGJVKIEHH-UHFFFAOYSA-N [1]benzofuro[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3OC2=C1 FBVBNCGJVKIEHH-UHFFFAOYSA-N 0.000 description 2
- ITOKSWHFPQBNSE-UHFFFAOYSA-N [1]benzofuro[3,2-d]pyrimidine Chemical compound N1=CN=C2C3=CC=CC=C3OC2=C1 ITOKSWHFPQBNSE-UHFFFAOYSA-N 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- PQIUGRLKNKSKTC-UHFFFAOYSA-N benzo[h]quinazoline Chemical compound N1=CN=C2C3=CC=CC=C3C=CC2=C1 PQIUGRLKNKSKTC-UHFFFAOYSA-N 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 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 2
- 230000007423 decrease Effects 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
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- QKEBGAUJUHZNNU-UHFFFAOYSA-N 9h-pyrrolo[2,3-f]quinoxaline Chemical compound N1=CC=NC2=C(NC=C3)C3=CC=C21 QKEBGAUJUHZNNU-UHFFFAOYSA-N 0.000 description 1
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- BJHVGSLMZTVDRA-UHFFFAOYSA-N [1]benzothiolo[2,3-b]pyrazine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=N1 BJHVGSLMZTVDRA-UHFFFAOYSA-N 0.000 description 1
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 1
- OICJTSLHQGDCTQ-UHFFFAOYSA-N [1]benzothiolo[3,2-d]pyrimidine Chemical compound N1=CN=C2C3=CC=CC=C3SC2=C1 OICJTSLHQGDCTQ-UHFFFAOYSA-N 0.000 description 1
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- ASZJLWVOAYYGRX-UHFFFAOYSA-N benzene;9h-carbazole Chemical compound C1=CC=CC=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 ASZJLWVOAYYGRX-UHFFFAOYSA-N 0.000 description 1
- XEMRLVBSKVCUDL-UHFFFAOYSA-N benzo[g]quinoxaline Chemical compound N1=CC=NC2=CC3=CC=CC=C3C=C21 XEMRLVBSKVCUDL-UHFFFAOYSA-N 0.000 description 1
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- YRUMDWGUXBZEPE-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1.C1CCCCC1 YRUMDWGUXBZEPE-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- MNXYJVWXMUBENA-UHFFFAOYSA-N dinaphthofuran Chemical compound C1=CC=CC2=C(C3=C(C4=CC=CC=C4C=C3)O3)C3=CC=C21 MNXYJVWXMUBENA-UHFFFAOYSA-N 0.000 description 1
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- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 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
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- YTIFDAAZLZVHIX-UHFFFAOYSA-N naphtho[1,2-g][1]benzofuran Chemical compound C1=CC=C2C3=CC=C4C=COC4=C3C=CC2=C1 YTIFDAAZLZVHIX-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- MCBJUXFCNBVPNF-UHFFFAOYSA-N phenanthro[9,10-d]pyrimidine Chemical compound C1=NC=C2C3=CC=CC=C3C3=CC=CC=C3C2=N1 MCBJUXFCNBVPNF-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- PLZDHJUUEGCXJH-UHFFFAOYSA-N pyrido[4,3-d]pyrimidine Chemical compound C1=NC=C2C=NC=CC2=N1 PLZDHJUUEGCXJH-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000005576 pyrimidinylene group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- QQNLHOMPVNTETJ-UHFFFAOYSA-N spiro[fluorene-9,9'-xanthene] Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11C2=CC=CC=C2C2=CC=CC=C21 QQNLHOMPVNTETJ-UHFFFAOYSA-N 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- PWYVVBKROXXHEB-UHFFFAOYSA-M trimethyl-[3-(1-methyl-2,3,4,5-tetraphenylsilol-1-yl)propyl]azanium;iodide Chemical compound [I-].C[N+](C)(C)CCC[Si]1(C)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PWYVVBKROXXHEB-UHFFFAOYSA-M 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The present invention provides a compound represented by chemical formula 1, an organic electronic element including a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, and an electronic device including the organic electronic element. The organic layer includes the compound represented by chemical formula 1, so that the driving voltage of the organic electric element can be reduced, and the light emitting efficiency and the lifetime can be improved.
Description
Technical Field
The present invention relates to a compound for an organic electronic device, an organic electronic device using the same, and an electronic device using the same.
Background
In general, an organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic substance. An organic electronic device utilizing the organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic layer therebetween. The organic layer is generally formed in a multilayer structure composed of various different substances in order to improve efficiency and stability of the organic electronic device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
In the organic electroluminescent element, lifetime and efficiency are the most problematic, and as the display grows in size, such efficiency or lifetime becomes a necessity.
Efficiency, lifetime, driving voltage, and the like are related to each other, and if efficiency increases, driving voltage relatively decreases, and crystallization of organic substances by Joule heating (Joule heating) that occurs when driving is performed with decreasing driving voltage decreases, and eventually lifetime tends to increase. However, even if the organic layer is simply improved, the efficiency cannot be maximized. This is because only the energy level (energy level) and T between the organic layers 1 The value, the intrinsic properties of the substance (mobility, surface properties, etc.) forming the optimum combinationLong life and high efficiency can be achieved at the same time.
Therefore, in order to fully develop the excellent characteristics of the organic electric element, it is necessary to develop a substance constituting the organic layer in the element, in particular, a hole transport layer and a light emitting auxiliary layer.
Disclosure of Invention
Technical problem
The purpose of the present invention is to provide a compound that can reduce the drive voltage of an element and can improve the luminous efficiency and lifetime, and an organic electric element and an electronic device using the same.
Technical proposal
In one aspect, the present invention provides a compound represented by the following chemical formula.
In another aspect, the present invention provides an organic electric element including the compound represented by the above chemical formula and an electronic device thereof.
Technical effects
By using the compound of the embodiment of the invention, not only the driving voltage of the element can be reduced, but also the luminous efficiency and the service life of the element can be improved.
Drawings
Fig. 1 to 3 are illustrations of an organic electroluminescent element according to an embodiment of the present invention.
Description of the reference numerals
100. 200, 300: organic electrical element 110: first electrode
120: hole injection layer 130: hole transport layer
140: light emitting layer 150: electron transport layer
160: electron injection layer 170: second electrode
180: light efficiency improvement layer 210: buffer layer
220: light emission auxiliary layer 320: first hole injection layer
330: first hole transport layer 340: a first light-emitting layer
350: first electron transport layer 360: a first charge generation layer
361: second charge generation layer 420: a second hole injection layer
430: second hole transport layer 440: a second light-emitting layer
450: second electron transport layer CGL: charge generation layer
ST1: first stack ST2: second stack
Detailed Description
The terms "aryl" and "arylene" used in the present invention have carbon numbers of 6 to 60, respectively, unless otherwise specified, but are not limited thereto. In the present invention, the aryl group or arylene group includes monocyclic, ring aggregate, fused polycyclic, spiro compound and the like.
The term "fluorenyl" as used in the present invention means a substituted or unsubstituted fluorenyl group, "fluorenylene" means a substituted or unsubstituted fluorenylene group, and fluorenyl or fluorenylene groups as used in the present invention include spiro compounds formed by the mutual bonding of R and R 'in the following structures, and also include cyclic compounds formed by the mutual bonding of adjacent R'. "substituted fluorenyl", "substituted fluorenylene" means that at least one of the substituents R, R', R "in the following structure is a substituent other than hydrogen, and R" in the following structure may be 1 to 8 valent. Regardless of valence, both fluorenyl and fluorenylene groups may be referred to herein as fluorenyl fluorene rings or fluorenes.
The term "spiro compound" as used in the present invention means "spiro union" and spiro union means that only one atom is shared by two spiro atom rings, thereby achieving the connection. At this time, the atoms shared in the two rings are referred to as "", and these are referred to as "single spiro-", "double spiro-", and "triple spiro-" compounds, respectively, according to of spiro atoms included in one compound.
The term "heterocyclic group" used in the present invention includes not only an aromatic ring such as "heteroaryl" or "heteroarylene" but also a non-aromatic ring, and unless otherwise specified, means a ring having 2 to 60 carbon atoms each containing one or more hetero atoms, but the present invention is not limited thereto. The term "heteroatom" used in the present invention, unless otherwise specified, means, for example, N, O, S, P or Si as an element other than carbon, and may include SO containing, instead of carbon forming a ring, a compound as described below 2 And p=o, etc. The heterocyclic group means a monocyclic group containing a heteroatom, a ring aggregate, a polycyclic compound after fusion, a spiro compound, or the like.
The term "aliphatic cyclic group" as used in the present invention means cyclic hydrocarbon other than aromatic hydrocarbon, including monocyclic, cyclic aggregate, fused polycyclic and spiro compounds, etc., and unless otherwise specified, means a ring having 3 to 60 carbon atoms, but is not limited thereto. For example, when benzene as an aromatic ring and cyclohexane (cyclohexane) as a non-aromatic ring are fused, the aromatic ring corresponds to an aliphatic ring.
In the present specification, "group names" corresponding to aryl groups, arylene groups, heterocyclic groups, and the like, which are shown by examples of the symbols and substituents thereof, may be described as "names of groups reflecting valence", but may also be described as "parent compound names". For example, in the case of "phenanthrene" which is one type of aryl group, the monovalent "group" is "phenanthryl" (phenanthrylene), the divalent group is "phenanthrylene" (phenanthrylene), and the like, and the names of the groups may be described by distinguishing the valence numbers, but may be described as "phenanthrene" which is the name of the parent compound, regardless of the valence numbers. Similarly, in the case of pyrimidine, the term "pyrimidine" may be used independently of the valence, or the term "name of the radical" of the valence, for example, in the case of monovalent, the term "pyrimidinyl" may be used, in the case of divalent, the term "pyrimidinylene" may be used, or the like.
In the present invention, when the name of the compound or the name of the substituent is described, numerals, letters, or the like indicating the position may be omitted. For example, pyrido [4,3-d ] pyrimidine may be referred to as pyridopyrimidine, benzofuro [2,3-d ] pyrimidine may be referred to as benzofuropyrimidine, and 9, 9-dimethyl-9H-fluorene may be referred to as dimethylfluorene. Thus, either benzo [ g ] quinoxaline or benzo [ f ] quinoxaline may be described as a benzoquinoxaline.
The chemical formulas used in the present specification can be applied in the same manner as the definition of the substituents defined by the index of the following chemical formulas unless explicitly stated otherwise.
Wherein, in the case where a is an integer of 0, the substituent R 1 The absence, that is, when a is 0, means that hydrogen is bonded to each carbon forming the benzene ring, and in this case, the expression of hydrogen bonded to carbon may be omitted, and chemical formula or compound may be described. And, in the case where a is an integer of 1, one substituent R 1 In combination with one of the carbons used to form the benzene ring, in the case where a is an integer of 2 or 3, respectively, in a manner such that a is an integer of 4 to 6, in a manner such that a is an integer of 2 and above, R 1 May be the same or different from each other.
In the present specification, unless otherwise specified, when a condensed ring is represented, a number in the 'number-condensed ring' represents the number of condensed rings. For example, a form in which 3 rings like anthracene, phenanthrene, benzoquinazoline and the like are condensed with each other may be shown as a 3-condensed ring.
In the present specification, unless otherwise specified, when a ring is represented as a "number atom" such as a five-membered ring or a six-membered ring, the number in the "number-atom" represents the number of elements forming the ring. For example thiophene or furan may correspond to a five membered ring and benzene or pyridine may correspond to a six membered ring.
In the present specification, unless otherwise specified, the ring formed by bonding adjacent groups is selected from C 6 ～C 60 An aromatic ring group of (a); fluorenyl; c comprising at least one heteroatom of O, N, S, si and P 2 ～C 60 Heterocyclic groups of (a); c 3 ～C 60 Is a group consisting of aliphatic cyclic groups.
Unless otherwise indicated in the present specification, 'between adjacent groups' means that, when the following chemical formula is taken as an example, it is not only R 1 And R is 2 Between, R 2 And R is 3 Between, R 3 And R is 4 Between, R 5 And R is 6 And also includes R sharing one carbon 7 And R is 8 And may also include a binding as R 1 And R is 7 Between, R 1 And R is 8 Between or R 4 And R is 5 Substituents of ring constituent elements (carbon, nitrogen, etc.) which are not directly adjacent to each other. That is, when a substituent is present in a ring constituent element such as directly adjacent carbon or nitrogen, it may be an adjacent group, but when no substituent is bonded to a ring constituent element at a directly adjacent position, it may be an adjacent group to a substituent bonded to the next ring constituent element, and also may be referred to as an adjacent group between substituents bonded to the same ring constituent carbon. In the following chemical formula, R is as same as R 7 And R is 8 In the case where substituents bonded to the same carbon are bonded to each other to form a ring, a compound containing a spiro moiety can be formed.
In the present specification, "adjacent groups are bonded to each other to form a ring" is used in the same meaning as "adjacent groups are bonded to each other to selectively form a ring", and means that at least one pair of adjacent groups are bonded to each other to form a ring.
In the present specification, unless otherwise specified, the ring formed by bonding the aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic cyclic group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, and adjacent groups may be selected from the group consisting of heavy hydrogen, halogen, and C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted amino, substituted by C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted silyl, substituted with C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C 1 ～C 20 Alkylthio, C 1 ～C 20 Alkoxy, C 6 ～C 20 Aryloxy group, C 6 ～C 20 Arylthio radicals C 1 ～C 20 Alkyl, C of (2) 2 ～C 20 Alkenyl, C 2 ～C 20 Alkynyl, C 6 ～C 20 Aryl, fluorenyl, C comprising at least one heteroatom selected from the group consisting of O, N, S, si and P 2 ～C 20 Heterocyclic group of (C) 3 ～C 20 Further substituted with one or more substituents from the group consisting of aliphatic cyclic groups.
Next, a laminated structure of an organic electric element including the compound of the present invention will be described with reference to fig. 1 to 3.
In the process of adding reference numerals to the constituent elements of the respective drawings, it should be noted that the same reference numerals are given as much as possible to the same constituent elements even though they are shown in different drawings. In the process of describing the present invention, a detailed description will be omitted in the case where it is determined that the detailed description of known structures or functions related thereto will obscure the gist of the present invention.
In describing the structural elements of the present invention, terms such as first, second, A, B, (a), (b) and the like may be used. Such terms are merely used to distinguish one element from another and the nature, order, sequence, etc. of the elements are not limited by such terms. In the case where one structural element is "connected", "joined" or "coupled" to another structural element, the structural element may be directly connected or coupled to the other structural element, but it may be understood that other structural elements are "connected", "joined" or "coupled" between the respective structural elements.
In the case where a structural element such as a layer, a film, a region, or a plate is located "on" or "upper" another structural element, this is understood to be not only located "directly above" the other structural element but also to be located in the middle. Conversely, where a structural element is located "directly above" another portion, it is understood that there are no other portions in between.
Fig. 1 to 3 are illustrations of an organic electroluminescent element according to an embodiment of the present invention.
Referring to fig. 1, an organic electric element 100 according to an embodiment of the present invention includes: the first electrode 110 is formed on a substrate (not shown), the second electrode 170, and an organic layer between the first electrode 110 and the second electrode 170.
The first electrode 110 may be an anode, the second electrode 170 may be a cathode, and in the case of an inversion type, the first electrode may be a cathode and the second electrode may be an anode.
The organic layers may include a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, and an electron injection layer 160. Specifically, a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, and an electron injection layer 160 may be sequentially formed on the first electrode 110.
Preferably, the light efficiency improving layer 180 may be formed on one surface of the first electrode 110 or the second electrode 170, which is not in contact with the organic layer, and in the case of forming the light efficiency improving layer 180, the light efficiency of the organic electric element may be improved.
For example, the light efficiency improvement layer 180 may be formed on the second electrode 170, but in the case of an organic light emitting element that emits light from the front side (top emission), the light efficiency improvement layer 180 is formed, so that the loss of optical energy due to SPPs (surface plasmon polarizations) in the second electrode 170 can be reduced, and in the case of an organic light emitting element that emits light from the back side (bottom emission), the light efficiency improvement layer 180 can perform a buffer function for the second electrode 170.
A buffer layer 210 or a light-emitting auxiliary layer 220 may be further formed between the hole transport layer 130 and the light-emitting layer 140, which will be described with reference to fig. 2.
Referring to fig. 2, the organic electric element 200 according to another embodiment of the present invention may include a hole injection layer 120, a hole transport layer 130, a buffer layer 210, a light emitting auxiliary layer 220, a light emitting layer 140, an electron transport layer 150, an electron injection layer 160, and a second electrode 170, on which a light efficiency improvement layer 180 may be formed, sequentially formed on the first electrode 110.
Although not shown in fig. 2, an electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150.
In addition, according to another embodiment of the present invention, the organic layer may be formed in a form of a stack including a plurality of hole transporting layers, light emitting layers, and electron transporting layers. This is described with reference to fig. 3.
Referring to fig. 3, an organic electric element 300 according to still another embodiment of the present invention may be formed with two or more sets of stacks (ST 1, ST 2) of organic layers formed in multiple layers between a first electrode 110 and a second electrode 170, and a charge generation layer CGL is formed between the stacks of organic layers.
Specifically, the organic electronic device according to an embodiment of the present invention may include a first electrode 110, a first stack ST1, a charge generation layer CGL (Charge Generation Layer), a second stack ST2, a second electrode 170, and a light efficiency improving layer 180.
The first stack ST1 may include a first hole injection layer 320, a first hole transport layer 330, a first light emitting layer 340, and a first electron transport layer 350 as the organic layer formed on the first electrode 110, and the second stack ST2 may include a second hole injection layer 420, a second hole transport layer 430, a second light emitting layer 440, and a second electron transport layer 450. In this way, the first stack and the second stack may have organic layers having the same stacked structure, but may have organic layers having different stacked structures.
A charge generation layer CGL may be formed between the first stack ST1 and the second stack ST 2. The charge generation layer CGL may include a first charge generation layer 360 and a second charge generation layer 361. Such a charge generation layer CGL is formed between the first light emitting layer 340 and the second light emitting layer 440, increases current efficiency generated at the respective light emitting layers, and plays a role of smoothly distributing charges.
Although the first light emitting layer 340 may include a light emitting material including a blue fluorescent dopant in a blue host, and the second light emitting layer 440 may include a material doped with a cyan (yellow) dopant and a red dopant in a green host, the materials of the first light emitting layer 340 and the second light emitting layer 440 according to the embodiment of the present invention are not limited thereto.
In fig. 3, n may be an integer of 1 to 5, but when n is 2, a charge generation layer CGL and a third stack may be further stacked on the second stack ST 2.
As shown in fig. 3, in the case where a plurality of light-emitting layers are formed by means of a multilayer stack structure, not only an organic electroluminescent element that emits white light by means of a mixing effect of light emitted from each light-emitting layer but also an organic electroluminescent element that emits light of a plurality of colors can be prepared.
Although the compound represented by chemical formula 1 of the present invention may be used as a material of the hole injection layer 120, 320, 420, the hole transport layer 130, 330, 430, the buffer layer 210, the light emitting auxiliary layer 220, the electron transport layer 150, 350, 450, the electron injection layer 160, the light emitting layer 140, 340, 440, or the light efficiency improvement layer 180, it is preferable that the compound be used as a material of the hole transport layer 130, 330, 430, the light emitting auxiliary layer 220, or/and the light efficiency improvement layer 180.
Even for the same similar cores, the band gap (band gap), electrical properties, surface properties, etc. may be different depending on which substituent is bonded at which position, and thus it is necessary to study the selection of cores and the combination of sub-substituents bonded thereto, in particular, when the energy level and T between the organic layers 1 When the optimal combination of intrinsic properties (mobility, surface properties, etc.) of the substance is achieved, both long life and high efficiency can be achieved.
Accordingly, the compound represented by chemical formula 1 in the present invention is used as a material of the hole transport layer 130, 330, 430, the light emitting auxiliary layer 220, or/and the light efficiency improvement layer 180, so that the energy level between the organic layers and T can be increased 1 Values, intrinsic characteristics (mobility, surface characteristics, etc.), etc., are optimized while improving the lifetime and efficiency of the electromechanical element.
The organic electroluminescent element according to an embodiment of the present invention can be manufactured using various evaporation methods. The anode 110 can be formed by vapor deposition such as PVD or CVD, for example, by vapor deposition of a metal or a metal oxide having conductivity or an alloy thereof on a substrate, and an organic layer including the hole injection layer 120, the hole transport layer 130, the light emitting layer 140, the electron transport layer 150, and the electron injection layer 160 is formed thereon, and then a substance capable of functioning as the cathode 170 is vapor deposited thereon. A light-emitting auxiliary layer 220 may be further formed between the hole-transporting layer 130 and the light-emitting layer 140, and an electron-transporting auxiliary layer (not shown) may be further formed between the light-emitting layer 140 and the electron-transporting layer 150, as described above, or may be formed in a stack structure.
The organic layer is formed into a smaller number of layers by a solvent treatment or solvent refining method (solvent refining method) other than vapor deposition, for example, spin coating, nozzle printing, ink jet printing, slit coating, dip coating, roll-to-roll, doctor blading, screen printing, or thermal transfer method, using a plurality of polymer materials. Since the organic layer of the present invention can be formed by various methods, the protection scope of the present invention is not limited by the forming method.
The organic electric element according to an embodiment of the present invention may be classified into a front emission type, a rear emission type, or a double-sided emission type according to materials used.
And, the organic electric element according to an embodiment of the present invention is selected from the group consisting of an organic electric light emitting element, an organic solar cell, an organic photoreceptor, an organic transistor, an element for monochromatic illumination, and an element for quantum dot display.
Another embodiment of the present invention may include an electronic device including: a display device including the organic electric element of the present invention described above; and a control unit for controlling the display device. In this case, the electronic device may be a wireless communication terminal in the present or future, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a navigator, a game machine, various TVs, and various computers.
Hereinafter, the compound according to one aspect of the present invention will be described.
The compound of one aspect of the present invention is represented by the following chemical formula 1.
< chemical formula 1>
In the above chemical formula 1, each symbol can be defined as follows.
The nitrogen N of the amine group may be bound to the benzene ring moiety of the fluorene moiety, or to R', or to r″.
R 1 To R 4 Independently of each other selected from the group consisting of hydrogen; heavy hydrogen; halogen; cyano group; a nitro group; c (C) 6 ～C 60 Aryl of (a); fluorenyl; c comprising at least one heteroatom of O, N, S, si and P 2 ～C 60 Heterocyclic groups of (a); c (C) 3 ～C 60 An aliphatic cyclic group of (a); c (C) 1 ～C 20 Alkyl of (2)；C 2 ～C 20 Alkenyl of (c); c (C) 2 ～C 20 Alkynyl of (a); c (C) 1 ～C 20 Alkoxy groups of (a); c (C) 6 ～C 20 An aryloxy group of (a); -L' -N (R) a )(R b ) And adjacent groups can be combined with each other to form a ring.
a to c are integers of 0 to 4, d is an integer of 0 to 7, and R is an integer of 2 or more 1 R is respectively R 2 R is respectively R 3 R is respectively R 4 Respectively, are the same or different from each other,
when nitrogen N of the amine group is bound to the benzene ring portion of the fluorene moiety, a+b may be an integer of 7 or less.
Between adjacent groups, e.g. adjacent R 1 Between and adjacent R 2 Between and adjacent R 3 R is in between, or adjacent to 4 In the case where the above-mentioned rings are bonded to each other to form a ring, the above-mentioned ring may be selected from the group consisting of C 6 ～C 60 An aromatic ring group of (a); a fluorene ring group; c comprising at least one heteroatom of O, N, S, si and P 2 ～C 60 Heterocyclic groups of (a); c 3 ～C 60 Is a group consisting of aliphatic cyclic groups.
In the case where the ring formed by bonding adjacent groups to each other is an aromatic ring, the aromatic ring may be C 6 ～C 20 ，C 6 ～C 18 ，C 6 ～C 16 ，C 6 ～C 14 ，C 6 ～C 13 ，C 6 ～C 12 ，C 6 ～C 10 ，C 6 ，C 10 ，C 12 ，C 14 ，C 15 ，C 16 ，C 18 And the like, specifically benzene, naphthalene, anthracene, phenanthrene, pyrene, and the like.
R 'and R' are independently selected from hydrogen; c (C) 6 ～C 60 Aryl of (a); fluorenyl; c comprising at least one heteroatom selected from O, N, S, si and P 2 ～C 60 Heterocyclic groups of (a); c (C) 3 ～C 60 An aliphatic cyclic group of (a); c (C) 1 ～C 20 Alkyl of (a); c (C) 2 ～C 20 Alkenyl of (c); c (C) 2 ～C 20 Alkynyl of (a); c (C) 1 ～C 20 Alkoxy groups of (a); c 6 ～C 20 R 'and R' may be bonded to each other to form a ring. The nitrogen N of the amine group may be bonded to R 'or R "of the fluorene moiety, for example, when R' or R" is an aryl group, the above aryl group may be bonded to the nitrogen N of the amine group.
When R 'and R' may combine with each other to form a ring, a spiro compound may be formed. For example, when R 'and R' may combine with each other to form a ring, the ring may be selected from the group consisting of C 6 ～C 60 An aromatic ring group of (a); a fluorene ring group; c comprising at least one heteroatom selected from the group consisting of O, N, S, si and P 2 ～C 60 Heterocyclic groups of (a); c 3 ～C 60 In particular, R 'and R' may be bonded to each other to form a ring of xanthenes, fluorenes, acridines, etc., and for example, may form a ring comprising the following structure.
In the above structure, fluorene and carbon atoms to which R' and R "are bonded are shared with each other, corresponding to a spiro atom. In the above structure, X may be a direct bond, O, S, N (Ar) 1 ) Or C (R) 1 )(R 2 ) The above structure corresponds to fluorene (yl) when X is a direct bond, 9H-xanthene (xanthene) when X is O, 9H-thioxanthene (thioxanthene) when X is S, N (Ar) 1 ) When the structure corresponds to acridine or a derivative thereof, R 'and R' are combined with each other when X is a direct bond, and spirobifluorene or a derivative thereof is finally formed.
At C (R) 1 )(R 2 ) Wherein R is 1 R is R 2 Independently of each other selected from hydrogen, heavy hydrogen, halogen, and C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted silyl, substituted with C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl substitution orUnsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C 1 ～C 20 Alkylthio, C 1 ～C 20 Alkoxy, C 6 ～C 20 Aryloxy group, C 6 ～C 20 Arylthio radicals C 1 ～C 20 Alkyl, C of (2) 2 ～C 20 Alkenyl, C 2 ～C 20 Alkynyl, C 6 ～C 30 Aryl, fluorenyl, C comprising at least one heteroatom selected from the group consisting of O, N, S, si and P 2 ～C 30 Heterocyclic group of (C) 3 ～C 30 Is a group of aliphatic cyclic groups, R 1 And R is 2 Can be combined with each other to form a ring.
R 1 And R is 2 In the case of forming a ring by bonding to each other, the above-mentioned ring may be selected from the group consisting of C 6 ～C 60 An aromatic ring group of (a); a fluorene ring group; c comprising at least one heteroatom of O, N, S, si and P 2 ～C 60 Heterocyclic groups of (a); c 3 ～C 60 For example, if R 1 And R is 2 And are bonded to each other to form a fluorene ring, and then together with C to which these are bonded, spirobifluorene can be formed.
In N (Ar) 1 ) Ar in (1) 1 Is selected from C 6 ～C 30 Aryl, fluorenyl, C comprising at least one heteroatom of O, N, S, si and P 2 ～C 30 Heterocyclic groups of C 3 ～C 30 An aliphatic cyclic group, and combinations thereof.
L is selected from C 6 ～C 60 Arylene of (a); fluorenylene; c (C) 3 ～C 60 An aliphatic cyclic group of (a); c comprising at least one heteroatom of O, N, S, si and P 2 ～C 60 Heterocyclic groups of (a); and combinations thereof.
Ar 1 Is selected from C 6 ～C 60 Aryl of (a); fluorenyl; c comprising at least one heteroatom of O, N, S, si and P 2 ～C 60 Heterocyclic groups of (a); c (C) 3 ～C 60 An aliphatic cyclic group of (a); and their useAnd a group of combinations. For example, ar 1 May be C 12 ～C 25 Aryl or fluorenyl groups of (a).
The above L' is selected from single bond; c (C) 6 ～C 60 Arylene of (a); fluorenylene; c (C) 3 ～C 60 An aliphatic ring of (a); and C comprising at least one heteroatom of O, N, S, si and P 2 ～C 60 Is selected from the group consisting of heterocyclic groups.
R is as described above a R is R b Independently of one another selected from the group consisting of C 6 ～C 60 Aryl of (a); fluorenyl; c comprising at least one heteroatom of O, N, S, si and P 2 ～C 60 Heterocyclic groups of (a); c 3 ～C 60 Is a group consisting of aliphatic cyclic groups.
The above R 1 To R 4 、Ar 1 、R’、R”、R 1 、R 2 、R a 、R b In the case where at least one of them is an aryl group, the aryl group may be, for example, C 6 ～C 30 ，C 6 ～C 29 ，C 6 ～C 28 ，C 6 ～C 27 ，C 6 ～C 26 ，C 6 ～C 25 ，C 6 ～C 24 ，C 6 ～C 23 ，C 6 ～C 22 ，C 6 ～C 21 ，C 6 ～C 20 ，C 6 ～C 19 ，C 6 ～C 18 ，C 6 ～C 17 ，C 6 ～C 16 ，C 6 ～C 15 ，C 6 ～C 14 ，C 6 ～C 13 ，C 6 ～C 12 ，C 6 ～C 11 ，C 6 ～C 10 ，C 6 ，C 10 ，C 12 ，C 13 ，C 14 ，C 15 ，C 16 ，C 17 ，C 18 The aryl group of the above may be specifically benzene (phenyl), biphenyl (biphenyl), naphthalene (napthenyl), terphenyl (terphenyl), phenanthrene (triphenylene), triphenylene (triphenylene) and the like.
In the case where at least one of the L, L' groups is arylene, the aboveAryl may be, for example, C 6 ～C 30 ，C 6 ～C 29 ，C 6 ～C 28 ，C 6 ～C 27 ，C 6 ～C 26 ，C 6 ～C 25 ，C 6 ～C 24 ，C 6 ～C 23 ，C 6 ～C 22 ，C 6 ～C 21 ，C 6 ～C 20 ，C 6 ～C 19 ，C 6 ～C 18 ，C 6 ～C 17 ，C 6 ～C 16 ，C 6 ～C 15 ，C 6 ～C 14 ，C 6 ～C 13 ，C 6 ～C 12 ，C 6 ～C 11 ，C 6 ～C 10 ，C 6 ，C 10 ，C 12 ，C 13 ，C 14 ，C 15 ，C 16 ，C 17 ，C 18 And the like, and specifically, may be benzene (phenyl), biphenyl (biphenyl), naphthalene (napthenyl), terphenyl (terphenyl), phenanthrene (triphenylene), triphenylene (triphenylene), and the like.
The above R 1 To R 4 、Ar 1 、R’、R”、R 1 、R 2 、R a 、R b In the case where at least one of the heterocyclic groups L, L' is a heterocyclic group, the heterocyclic group may be, for example, C 2 ～C 30 ，C 2 ～C 29 ，C 2 ～C 28 ，C 2 ～C 27 ，C 2 ～C 26 ，C 2 ～C 25 ，C 2 ～C 24 ，C 2 ～C 23 ，C 2 ～C 22 ，C 2 ～C 21 ，C 2 ～C 20 ，C 2 ～C 19 ，C 2 ～C 18 ，C 2 ～C 17 ，C 2 ～C 16 ，C 2 ～C 15 ，C 2 ～C 14 ，C 2 ～C 13 ，C 2 ～C 12 ，C 2 ～C 11 ，C 2 ～C 10 ，C 2 ～C 9 ，C 2 ～C 8 ，C 2 ～C 7 ，C 2 ～C 6 ，C 2 ～C 5 ，C 2 ～C 4 ，C 2 ～C 3 ，C 2 ，C 3 ，C 4 ，C 5 ，C 6 ，C 7 ，C 8 ，C 9 ，C 10 ，C 11 ，C 12 ，C 13 ，C 14 ，C 15 ，C 16 ，C 17 ，C 18 ，C 19 ，C 20 ，C 21 ，C 22 ，C 23 ，C 24 ，C 25 ，C 26 ，C 27 ，C 28 ，C 29 And the like, and in particular, can be pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, silole, indene, indole, phenyl-indole, benzoindole, phenyl-benzoindole, pyrazinoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenanthroquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthacene, dinaphthiophene, carbazole, benzene-carbazole, benzocarbazole, benzo-benzocarbazole, naphthalene-benzocarbazole, benzoimidazole dibenzocarbazole, indolocarbazole, benzofuropyridine, benzothiophenopyridine, benzofuropyridine, benzothiophenopyrimidine, benzofuropyrimidine, benzothiophenopyrazine, benzofuropyrazine, benzimidazole, benzothiazole, benzoxazole, benzothiophene, phenanthroline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxazine, phenothiazine, dibenzodioxadiene, benzodibenzodioxadiene, thianthrene, 9-dimethyl-9H-xanthene, 9-dimethyl-9H-thioxanthene, dihydrodimethylphenylacridine, spiro [ fluorene-9, 9' -xanthene ]Etc.
The above R 1 To R 4 、Ar 1 、Ar 1 、R'、R”、R 1 、R 2 、R a 、R b In the case where at least one of the fluorenyl group and L, L' group is fluorenylene, the fluorenyl group or the fluorenylene groupThe fluorenyl group may be, for example, 9-dimethyl-9H-fluorene, 9-diphenyl-9H-fluorene, 9' -spirobifluorene, or spiro [ benzo [ b ]]Fluorene-11, 9' -fluorene]Benzo [ b ]]Fluorene, 11, 11-diphenyl-11H-benzo [ b ]]Fluorene, 9- (naphthalen-2-yl) 9-phenyl-9H-fluorene, and the like.
The above R 1 To R 4 、Ar 1 、Ar 1 、R'、R”、R 1 、R 2 、R a 、R b In the case where at least one of the groups L, L' is an aliphatic cyclic group, the aliphatic cyclic group may be, for example, C 3 ～C 30 ，C 3 ～C 29 ，C 3 ～C 28 ，C 3 ～C 27 ，C 3 ～C 26 ，C 3 ～C 25 ，C 3 ～C 24 ，C 3 ～C 23 ，C 3 ～C 22 ，C 3 ～C 21 ，C 3 ～C 20 ，C 3 ～C 19 ，C 3 ～C 18 ，C 3 ～C 17 ，C 3 ～C 13 ，C 3 ～C 15 ，C 3 ～C 14 ，C 3 ～C 13 ，C 3 ～C 12 ，C 3 ～C 11 ，C 3 ～C 10 ，C 3 ～C 8 ，C 3 ～C 6 ，C 6 ，C 10 ，C 11 ，C 12 ，C 13 ，C 14 ，C 15 ，C 16 ，C 17 ，C 18 And the like, specifically, a cyclohexane group (cyclo hexanyl group), an adamantyl group (adamantyl group), and the like.
The above R 1 To R 4 、R'、R”、R 1 、R 2 In the case where at least one of the alkyl groups is an alkyl group, the alkyl group may be, for example, C 1 ～C 20 、C 1 ～C 10 、C 1 ～C 4 、C 1 、C 2 、C 3 、C 4 The alkyl group such as methyl, ethyl, tert-butyl, etc. may be mentioned.
The above aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, alicyclic group,Alkyl, alkenyl, alkynyl, alkoxy, aryloxy, a ring formed by bonding adjacent groups to each other, a ring formed by bonding R 'and R', R 1 And R is 2 The rings formed by the combination of the two can be respectively selected from heavy hydrogen, halogen and C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted silyl, substituted with C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C 1 ～C 20 Alkylthio, C 1 ～C 20 Alkoxy, C 6 ～C 20 Aryloxy group, C 6 ～C 20 Arylthio radicals C 1 ～C 20 Alkyl, C of (2) 2 ～C 20 Alkenyl, C 2 ～C 20 Alkynyl, C 6 ～C 30 Aryl, fluorenyl, C comprising at least one heteroatom selected from the group consisting of O, N, S, si and P 2 ～C 30 Heterocyclic groups of C 3 ～C 30 Further substituted with one or more substituents selected from the group consisting of aliphatic cyclic groups, and combinations thereof.
Preferably, the aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic cyclic group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, ring formed by bonding adjacent groups to each other, ring formed by bonding R 'and R', R 1 And R is 2 The rings formed by the combination of the two can be respectively selected from heavy hydrogen, halogen and C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted silyl, substituted with C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C 1 ～C 20 Alkylthio, C 1 ～C 20 Alkoxy, C 6 ～C 20 Aryloxy group, C 6 ～C 20 Arylthio radicals C 1 ～C 20 Alkyl, C of (2) 2 ～C 20 Alkenyl, C 2 ～C 20 Alkynyl, C 6 ～C 20 Aryl, fluorenyl, C comprising at least one heteroatom selected from the group consisting of O, N, S, si and P 2 ～C 20 Heterocyclic groups of C 3 ～C 20 Further substituted with one or more substituents selected from the group consisting of aliphatic cyclic groups, and combinations thereof.
The above aryl, fluorenyl, heterocyclic, aliphatic cyclic, aromatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, fluorenylene, arylene, a ring formed by bonding adjacent groups to each other, a ring formed by bonding R 'and R', R 1 And R is 2 When at least one of the rings formed by the combination of the two is substituted by an aryl group, the aryl group may be, for example, C 2 ～C 30 ，C 2 ～C 29 ，C 2 ～C 28 ，C 2 ～C 27 ，C 2 ～C 26 ，C 2 ～C 25 ，C 2 ～C 24 ，C 2 ～C 23 ，C 2 ～C 22 ，C 2 ～C 21 ，C 2 ～C 20 ，C 2 ～C 19 ，C 2 ～C 18 ，C 2 ～C 17 ，C 2 ～C 16 ，C 2 ～C 15 ，C 2 ～C 14 ，C 2 ～C 13 ，C 2 ～C 12 ，C 2 ～C 11 ，C 2 ～C 10 ，C 6 ，C 10 ，C 12 ，C 13 ，C 14 ，C 15 ，C 16 ，C 17 ，C 18 And the like.
The above aryl, fluorenyl, heterocyclic, aliphatic cyclic, aromatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, fluorenylene, arylene, a ring formed by bonding adjacent groups to each other, a ring formed by bonding R 'and R', R 1 And R is 2 When at least one of the rings formed by the bonding is substituted with a heterocyclic group, the heterocyclic group may be, for example, C 2 ～C 30 ，C 2 ～C 29 ，C 2 ～C 28 ，C 2 ～C 27 ，C 2 ～C 26 ，C 2 ～C 25 ，C 2 ～C 24 ，C 2 ～C 23 ，C 2 ～C 22 ，C 2 ～C 21 ，C 2 ～C 20 ，C 2 ～C 19 ，C 2 ～C 18 ，C 2 ～C 17 ，C 2 ～C 16 ，C 2 ～C 15 ，C 2 ～C 14 ，C 2 ～C 13 ，C 2 ～C 12 ，C 2 ～C 11 ，C 2 ～C 10 ，C 2 ～C 9 ，C 2 ～C 8 ，C 2 ～C 7 ，C 2 ～C 6 ，C 2 ～C 5 ，C 2 ～C 4 ，C 2 ～C 3 ，C 2 ，C 3 ，C 4 ，C 5 ，C 6 ，C 7 ，C 8 ，C 9 ，C 10 ，C 11 ，C 12 ，C 13 ，C 14 ，C 15 ，C 16 ，C 17 ，C 18 ，C 19 ，C 20 ，C 21 ，C 22 ，C 23 ，C 24 ，C 25 ，C 26 ，C 27 ，C 28 ，C 29 And the like.
The above aryl, fluorenyl, heterocyclic, aliphatic cyclic, aromatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, fluorenylene, arylene, a ring formed by bonding adjacent groups to each other, a ring formed by bonding R 'and R', R 1 And R is 2 When at least one of the rings formed by the bonding is substituted with a fluorenyl group, the fluorenyl group may be, for example, 9-dimethyl-9H-fluorene, 9-diphenyl-9H-fluorene, 9' -spirobifluorene, or spiro [ benzo [ b ]]Fluorene-11, 9' -fluorene]Benzo [ b ]]Fluorene, 11, 11-diphenyl-11H-benzo [ b ]]Fluorene, 9- (naphthalen-2-yl) 9-phenyl-9H-fluorene, and the like.
When the above aryl group, fluorenyl group, heterocyclic group, alicyclic group,Aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, fluorenylene group, arylene group, ring formed by bonding adjacent groups to each other, ring formed by bonding R 'and R', R 1 And R is 2 When at least one of the rings formed by the combination of the two is substituted by an alkyl group, the alkyl group may be, for example, C 1 ～C 20 、C 1 ～C 10 、C 1 ～C 4 、C 1 、C 2 、C 3 、C 4 And the like.
The above aryl, fluorenyl, heterocyclic, aliphatic cyclic, aromatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, fluorenylene, arylene, a ring formed by bonding adjacent groups to each other, a ring formed by bonding R 'and R', R 1 And R is 2 When at least one of the rings formed by the bonding is substituted with an alkoxy group, the alkoxy group may be, for example, C 1 ～C 20 、C 1 ～C 10 、C 1 ～C 4 、C 1 、C 2 、C 3 、C 4 And the like.
The above aryl, fluorenyl, heterocyclic, aliphatic cyclic, aromatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, fluorenylene, arylene, a ring formed by bonding adjacent groups to each other, a ring formed by bonding R 'and R', R 1 And R is 2 When at least one of the rings formed by the bonding is substituted with an aliphatic cyclic group, the aliphatic cyclic group may be, for example, C 3 ～C 30 ，C 3 ～C 29 ，C 3 ～C 28 ，C 3 ～C 27 ，C 3 ～C 26 ，C 3 ～C 25 ，C 3 ～C 24 ，C 3 ～C 23 ，C 3 ～C 22 ，C 3 ～C 21 ，C 3 ～C 20 ，C 3 ～C 19 ，C 3 ～C 18 ，C 3 ～C 17 ，C 3 ～C 13 ，C 3 ～C 15 ，C 3 ～C 14 ，C 3 ～C 13 ，C 3 ～C 12 ，C 3 ～C 11 ，C 3 ～C 10 ，C 3 ～C 8 ，C 3 ～C 6 ，C 6 ，C 10 ，C 11 ，C 12 ，C 13 ，C 14 ，C 15 ，C 16 ，C 17 ，C 18 And the like.
The compound represented by the above chemical formula 1 may be represented by one of the following chemical formulas 2 to 22, chemical formula 7-1 to chemical formula 10-1.
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In the above chemical formulas 2 to 22, chemical formulas 7-1 to 10-1, each symbol can be defined as follows.
R 1 ～R 4 、R’、R”、Ar 1 L, a, c, d are as defined in chemical formula 1, and represent binding sites. For example, in formulas 12, 17, and 18, an amine group may be bonded to carbon represented by x, and in formulas 14, 21, and 22, a fluorene substituent may be bonded to carbon represented by x.
In chemical formulas 2 to 2In chemical formula 6, b is as defined in chemical formula 1, and in chemical formula 7, chemical formula 8, chemical formula 11, chemical formula 12, chemical formula 15 to chemical formula 18, chemical formula 7-1 and chemical formula 8-1, b is an integer of 0 to 3, and in chemical formula 9, chemical formula 10, chemical formula 13, chemical formula 14, chemical formula 19 to chemical formula 22, chemical formula 9-1 and chemical formula 10-1, b is an integer of 0 to 4, and b is an integer of 2 or more, R 2 Respectively the same or different.
X is a direct bond, O, S, N (Ar) 1 ) Or C (R) 1 )(R 2 )。
R 5 ，R 6 ，R 11 To R 15 ，R 1 R is R 2 Independently of each other selected from hydrogen, heavy hydrogen, halogen, and C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted silyl, substituted with C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C 1 ～C 20 Alkylthio, C 1 ～C 20 Alkoxy, C 6 ～C 20 Aryloxy group, C 6 ～C 20 Arylthio radicals C 1 ～C 20 Alkyl, C of (2) 2 ～C 20 Alkenyl, C 2 ～C 20 Alkynyl, C 6 ～C 30 Aryl, fluorenyl, C comprising at least one heteroatom selected from the group consisting of O, N, S, si and P 2 ～C 30 Heterocyclic groups of C 3 ～C 30 And combinations thereof, and adjacent groups may be bonded to each other to form a ring, R 1 And R is 2 Can be combined with each other to form a ring.
Between adjacent groups, e.g. adjacent R 5 Between and adjacent R 6 Between and adjacent R 11 Between and adjacent R 12 Between and adjacent R 13 Between and adjacent R 14 R is in between, or adjacent to 15 In the case where the above-mentioned rings are bonded to each other to form a ring, the above-mentioned ring may be selected from the group consisting of C 6 ～C 30 An aromatic ring group of (a); fluorene ringA base; c comprising at least one heteroatom of O, N, S, si and P 2 ～C 30 Heterocyclic groups of (a); c 3 ～C 30 Is a group consisting of aliphatic cyclic groups.
In the case where the ring formed by bonding adjacent groups to each other is an aromatic ring, the aromatic ring may be, for example, C 6 ～C 20 ，C 6 ～C 18 ，C 6 ～C 16 ，C 6 ～C 14 ，C 6 ～C 13 ，C 6 ～C 12 ，C 6 ～C 10 ，C 6 ，C 10 ，C 12 ，C 14 ，C 15 ，C 16 ，C 18 And the like, specifically benzene, naphthalene, anthracene, phenanthrene, pyrene, and the like.
When R is 1 And R is 2 When they are combined with each other to form a ring, they may form a spiro compound. When R is 1 And R is 2 When they are combined with each other to form a ring, the ring may be selected from the group consisting of C 6 ～C 30 An aromatic ring group of (a); a fluorene ring group; c comprising at least one heteroatom of O, N, S, si and P 2 ～C 30 Heterocyclic groups of (a); c 3 ～C 30 Is a group consisting of aliphatic cyclic groups.
Ar as described above 1 Is selected from C 6 ～C 30 Aryl, fluorenyl, C comprising at least one heteroatom of O, N, S, si and P 2 ～C 30 Heterocyclic groups of C 3 ～C 30 An aliphatic cyclic group, and combinations thereof.
In chemical formula 6, in chemical formulae 7-1 to 10-1, e is an integer of 0 to 5, in chemical formulae 11 to 22, e is an integer of 0 to 4, and when e is an integer of 2 or more, R 5 Respectively the same or different.
f is an integer of 0 to 5, m, n, o and p are each an integer of 0 to 4, q is an integer of 0 to 3, and R is an integer of 2 or more 6 R is respectively R 11 R is respectively R 12 R is respectively R 13 R is respectively R 14 R is respectively R 15 Respectively the same or different.
In formulae 2 to 4, formulae 7 to 14, formulae 7-1 to 10-1, d may be 0, or R 4 May be hydrogen. In addition, in chemical formula 8, R 1 To R 6 ，R 11 R is R 12 May all be hydrogen, or a to f, m and n may all be 0.
The above R 5 、R 6 、R 11 To R 15 、R 1 、R 2 、Ar 1 In the case where at least one of them is an aryl group, the aryl group may be, for example, C 6 ～C 30 ，C 6 ～C 29 ，C 6 ～C 28 ，C 6 ～C 27 ，C 6 ～C 26 ，C 6 ～C 25 ，C 6 ～C 24 ，C 6 ～C 23 ，C 6 ～C 22 ，C 6 ～C 21 ，C 6 ～C20，C 6 ～C 19 ，C 6 ～C 18 ，C 6 ～C 17 ，C 6 ～C 16 ，C 6 ～C 15 ，C 6 ～C 14 ，C 6 ～C 13 ，C 6 ～C 12 ，C 6 ～C 11 ，C 6 ～C 10 ，C 6 ，C 10 ，C 12 ，C 13 ，C 14 ，C 15 ，C 16 ，C 17 ，C 18 The aryl group of the above may be specifically benzene (phenyl), biphenyl (biphenyl), naphthalene (napthenyl), terphenyl (terphenyl), phenanthrene (triphenylene), triphenylene (triphenylene) and the like.
The above R 5 、R 6 、R 11 To R 15 、R 1 、R 2 、Ar 1 In the case where at least one of them is a heterocyclic group, the heterocyclic group may be, for example, C 2 ～C 30 ，C 2 ～C 29 ，C 2 ～C 28 ，C 2 ～C 27 ，C 2 ～C 26 ，C 2 ～C 25 ，C 2 ～C 24 ，C 2 ～C 23 ，C 2 ～C 22 ，C 2 ～C 21 ，C 2 ～C 20 ，C 2 ～C 19 ，C 2 ～C 18 ，C 2 ～C 17 ，C 2 ～C 16 ，C 2 ～C 15 ，C 2 ～C 14 ，C 2 ～C 13 ，C 2 ～C 12 ，C 2 ～C 11 ，C 2 ～C 10 ，C 2 ～C 9 ，C 2 ～C 8 ，C 2 ～C 7 ，C 2 ～C 6 ，C 2 ～C 5 ，C 2 ～C 4 ，C 2 ～C 3 ，C 2 ，C 3 ，C 4 ，C 5 ，C 6 ，C 7 ，C 8 ，C 9 ，C 10 ，C 11 ，C 12 ，C 13 ，C 14 ，C 15 ，C 16 ，C 17 ，C 18 ，C 19 ，C 20 ，C 21 ，C 22 ，C 23 ，C 24 ，C 25 ，C 26 ，C 27 ，C 28 ，C 29 And the like.
The above R 5 、R 6 、R 11 To R 15 、R 1 、R 2 、Ar 1 In the case where at least one of them is a fluorenyl group, the fluorenyl group may be 9, 9-dimethyl-9H-fluorene, 9-diphenyl-9H-fluorene, 9' -spirobifluorene, or spiro [ benzo [ b ]]Fluorene-11, 9' -fluorene]Benzo [ b ]]Fluorene, 11, 11-diphenyl-11H-benzo [ b ]]Fluorene, 9- (naphthalen-2-yl) 9-phenyl-9H-fluorene, and the like.
The above R 5 、R 6 、R 11 To R 15 、R 1 、R 2 、Ar 1 In the case where at least one of them is an aliphatic cyclic group, the aliphatic cyclic group may be, for example, C 3 ～C 30 ，C 3 ～C 29 ，C 3 ～C 28 ，C 3 ～C 27 ，C 3 ～C 26 ，C 3 ～C 25 ，C 3 ～C 24 ，C 3 ～C 23 ，C 3 ～C 22 ，C 3 ～C 21 ，C 3 ～C 20 ，C 3 ～C 19 ，C 3 ～C 18 ，C 3 ～C 17 ，C 3 ～C 13 ，C 3 ～C 15 ，C 3 ～C 14 ，C 3 ～C 13 ，C 3 ～C 12 ，C 3 ～C 11 ，C 3 ～C 10 ，C 3 ～C 8 ，C 3 ～C 6 ，C 6 ，C 10 ，C 11 ，C 12 ，C 13 ，C 14 ，C 15 ，C 16 ，C 17 ，C 18 And the like, specifically, a cyclohexane group (cyclo hexanyl group), an adamantyl group (adamantyl group), and the like.
The above R 5 、R 6 、R 11 To R 15 、R 1 、R 2 In the case where at least one of the alkyl groups is an alkyl group, the alkyl group may be, for example, C 1 ～C 20 、C 1 ～C 10 、C 1 ～C 4 、C 1 、C 2 、C 3 、C 4 The alkyl group such as methyl, ethyl, tert-butyl, etc. may be mentioned.
R is as described above 5 ，R 6 ，R 11 To R 15 ，R 1 ，R 2 ，Ar 1 A ring formed by bonding adjacent groups to each other, R 1 And R is 2 The rings formed by the combination of the two can be respectively selected from heavy hydrogen, halogen and C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted silyl, substituted with C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C 1 ～C 20 Alkylthio, C 1 ～C 20 Alkoxy, C 6 ～C 20 Aryloxy group, C 6 ～C 20 Arylthio radicals C 1 ～C 20 Alkyl, C of (2) 2 ～C 20 Alkenyl, C 2 ～C 20 Alkynyl, C 6 ～C 30 Aryl, fluorenyl, C comprising at least one heteroatom selected from the group consisting of O, N, S, si and P 2 ～C 30 Heterocyclic groups of C 3 ～C 30 Further substituted with one or more substituents from the group consisting of aliphatic cyclic groups.
Specifically, the compound represented by the above chemical formula 1 may be one of the following compounds, but is not limited thereto.
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According to another aspect of the present invention, there is provided an organic electronic component including a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, wherein the organic layer includes a compound represented by chemical formula 1.
The organic layer may include a light-emitting layer, the hole-transporting layer between the light-emitting layer and the first electrode, and a light-emitting auxiliary layer between the hole-transporting layer and the first electrode, and the compound may be included in at least one of the hole-transporting layer and the light-emitting auxiliary layer.
The organic electronic device further includes a light efficiency improving layer including a compound represented by chemical formula 1, and in this case, the light efficiency improving layer is formed on one surface of the first electrode and the second electrode, which is not in contact with the organic layer.
The organic layer may include two or more stacks, and may include a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the anode, and the organic layer may further include a charge generation layer formed between the two or more stacks.
According to still another aspect of the present invention, there is provided an electronic device including a display device including a compound represented by chemical formula 1 and a control unit for driving the display device.
The following examples are given to specifically illustrate examples of synthesis of the compound represented by chemical formula 1 and examples of production of the organic electric element according to the present invention, but the present invention is not limited to the following examples.
Synthesis example
The compound represented by chemical formula 1 according to the present invention may be prepared by reacting Sub1 with Sub2 as in the following reaction formula 1, but is not limited thereto.
< reaction formula 1> (Hal is I, br or Cl.)
Illustration of Sub1
Sub1 in reaction formula 1 may be a compound with, but is not limited to, FD-MS (Field degradation-Mass Spectrometry) values of the following compounds are shown in table 1, respectively.
TABLE 1
| Compounds of formula (I) | FD-MS | Compounds of formula (I) | FD-MS |
| Sub 1-1 | CAS NO＝1225053-54-2 | Sub 1-2 | CAS NO＝28320-31-2 |
| Sub 1-3 | CAS NO＝1190360-23-6 | Sub 1-4 | CAS NO＝942615-32-9 |
| Sub 1-5 | m/z＝348.05(C 21 H 17 Br＝349.27) | Sub 1-6 | m/z＝348.05(C 21 H 17 Br＝349.27) |
| Sub 1-7 | m/z＝406.13(C 25 H 27 Br＝407.4) | Sub 1-8 | m/z＝328.08(C 19 H 21 Br＝329.28) |
| Sub 1-9 | CAS NO＝171408-76-7 | Sub 1-10 | CAS NO＝1161009-88-6 |
| Sub 1-11 | m/z＝394.04(C 25 H 15 Br＝395.3) | Sub 1-12 | m/z＝470.07(C 31 H 19 Br＝471.4) |
| Sub 1-13 | m/z＝528.15(C 35 H 29 Br＝529.52) | Sub 1-14 | m/z＝450.1(C 29 H 23 Br＝451.41) |
| Sub 1-15 | CAS NO＝1547491-70-2 | Sub 1-16 | m/z＝396.05(C 25 H 17 Br＝397.32) |
| Sub 1-17 | m/z＝530.16(C 35 H 31 Br＝531.54) | Sub 1-18 | m/z＝452.11(C 29 H 25 Br＝453.42) |
| Sub 1-19 | m/z＝472.08(C 31 H 21 Br＝473.41) | Sub 1-20 | m/z＝334.04(C 20 H 15 Br＝335.24) |
| Sub 1-21 | m/z＝334.04(C 20 H 15 Br＝335.24) | Sub 1-22 | m/z＝334.04(C 20 H 15 Br＝335.24) |
| Sub 1-23 | m/z＝390.1(C 24 H 23 Br＝391.35) | Sub 1-24 | m/z＝396.05(C 25 H 17 Br＝397.32) |
| Sub 1-25 | CAS NO＝1257251-75-4 | Sub 1-26 | CAS NO＝1998216-26-4 |
| Sub 1-27 | m/z＝562.09(C 37 H 23 Br0＝563.49) | Sub 1-28 | CAS NO＝1477458-14-2 |
| Sub 1-29 | CAS NO＝899422-06-1 | Sub 1-30 | CAS NO＝1643935-07-2 |
| Sub 1-31 | CAS NO＝1640344-19-9 | Sub 1-32 | CAS NO＝2086293-11-8 |
| Sub 1-33 | CAS NO＝2360947-56-2 | Sub 1-34 | m/z＝492.11(C 31 H 25 BrO＝493.44) |
| Sub 1-35 | m/z＝466.09(C 29 H 23 Br0＝467.41) | Sub 1-36 | m/z＝508.09(C 31 H 25 BrS＝509.51) |
| Sub 1-37 | m/z＝502.04(C 31 H 19 BrS＝503.46) | Sub 1-38 | m/z＝485.08(C 31 H 20 BrN＝486.41) |
| Sub 1-39 | m/z＝436.08(C 28 H 21 Br＝437.38) | Sub 1-40 | m/z＝394.04(C 25 H 15 Br＝395.3) |
Synthesis example of Sub2
Sub2 of the reaction scheme 1 can be synthesized by the reaction scheme of the following reaction scheme 2, and Sub2-I can be synthesized by the following reaction scheme 3, but is not limited thereto.
< reaction No. 2>
< reaction No. 3>
Synthesis example of Sub2-3
(1) Synthesis example of Sub2-3-c
To Sub2-3-a (26 g,91.9 mmol) were added Sub2-3-b (22.8 g,91.9 mmol), pd (PPh 3 ) 4 (0.05 eq.) K 2 CO 3 (3 eq.) and THF/H 2 O (306 ml/153 ml) and refluxed for 12 hours. After the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, and THF was removed. Extracted with MC and wiped with water. The organic layer was dried over MgSO 4 After drying and concentration, the resultant concentrate was separated by a silica gel column, whereby 28.5g (yield: 96.4%) of a resultant was obtained.
(2) Synthesis example of Sub2-I-3
To Sub2-3-c (28.5 g,79.3 mmol) was added Sub2-3-d(12.4g，79.3mmol)、Pd(PPh 3 ) 4 (0.05 eq.) K 2 CO 3 (3 eq.) and THF/H 2 O (264 ml/132 ml) was synthesized in the same manner as in the synthesis example of Sub2-3-c described above, whereby 25.8g (yield: 83.4%) of a product was obtained.
(3) Synthesis example of Sub2-3
Sub2-I-3 (25.8 g,66 mmol) was dissolved in toluene (676 ml), and Sub2-II-3 (11.7 g,69.3 mmol) and Pd were added 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq.) and NaOt-Bu (3 eq.) and stirring is carried out at 100 ℃. After completion of the reaction, the reaction mixture was treated with CH 2 Cl 2 And extracting the organic layer with water over MgSO 4 Drying and concentrating. Thereafter, the concentrate was separated by a silica gel column and then subjected to recrystallization, whereby 28.4g (yield: 82.3%) of a product was obtained.
Synthesis example of Sub2-8
To Sub2-I-8 (25 g,79.4 mmol) was added Sub2-II-8 (18.8 g,83.38 mmol), pd 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (814 ml) were carried out in the same manner as in the synthesis example of Sub2-3 described above, whereby 32.2g (yield: 80.7%) of a product was obtained.
Synthesis example of Sub2-14
To Sub2-I-14 (22 g,69.9 mmol) was added Sub2-II-14 (15.4 g,73.4 mmol), pd 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (716 ml) were carried out in the same manner as in the above synthesis example of Sub2-3, whereby 27.6g (yield: 81%) of a product was obtained.
Synthesis example of Sub2-27
To Sub2-I-27 (23 g,58.8 mmol) was added Sub2-II-27 (12.9 g,61.8 mmol), pd 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (603 ml) were carried out in the same manner as in the synthesis example of Sub2-3 described above, whereby 26.7g (yield: 80.5%) of a product was obtained.
Synthesis example of Sub2-32
To Sub2-I-32 (19 g,47.9 mmol) was added Sub2-II-32 (8.5 g,50.3 mmol), pd 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (491 ml) were carried out in the same manner as in the above-described synthesis example of Sub2-3, whereby 19.2g (yield: 75.6%) of a product was obtained.
Synthesis example of Sub2-39
Sub2-II-39 (15.3 g,53.7 mmol), pd were added to Sub2-I-39 (20 g,51.2 mmol) 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (524 ml) were carried out in the same manner as in the synthesis example of Sub2-3 described above, whereby 23.2g (yield: 71%) of a product was obtained.
Synthesis example of Sub2-53
To Sub2-I-53 (21 g,66.7 mmol) was added Sub2-II-53 (12.8 g,70 mmol), pd 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 equivalent), naOtBu (3 equivalents), and toluene (684 ml) were carried out in the same manner as in the synthesis example of Sub2-3 described above to obtain 23.5g (yield: 76.2%) of a product.
Synthesis example of Sub2-66
To Sub2-I-66 (22 g,56.3 mmol) was added Sub2-II-66 (12.9 g,59.1 mmol), pd 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (577 ml) were carried out in the same manner as in the above synthesis example of Sub2-3, whereby 26.1g (yield: 80.9%) of a product was obtained.
Synthesis example of Sub2-68
To Sub2-I-68 (19 g,63.4 mmol) was added Sub2-II-68 (11 g,63.4 mmol), pd 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (619 ml) were carried out in the same manner as in the synthesis example of Sub2-3 described above, whereby 21g (yield: 76.8%) of a product was obtained.
Synthesis example of Sub2-71
To Sub2-I-71 (19 g,43.5 mmol) was added Sub2-II-71 (8.5 g,45.7 mmol), pd 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (446 ml) were carried out in the same manner as in the above synthesis example of Sub2-3, whereby 16.4g (yield: 69.8%) of a product was obtained.
The compounds belonging to Sub2 may be, but not limited to, the following compounds, and table 2 shows FD-MS values of the following compounds.
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TABLE 2
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Synthesis example of end product
Synthesis example of P1-1
Sub2-48 (43.01 g,96.09 mmol) and Pd were added after dissolving Sub1-2 (32 g,91.52 mmol) in toluene (938 ml) 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq.) and NaOt-Bu (3 eq.) and stirring is carried out at 100 ℃. After completion of the reaction, the reaction mixture was treated with CH 2 Cl 2 And extracting the organic layer with water over MgSO 4 Drying and concentrating. Thereafter, the concentrate was separated by a silica gel column and then recrystallized, whereby 44.27g (yield: 75.6%) of a product was obtained.
Synthesis example of P1-3
Sub2-3 (60.39 g,115.31 mmol), pd was added to Sub1-2 (30 g,109.82 mmol) 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (1126 ml) were carried out in the same manner as in the above-described synthesis example of P1-1, whereby 67.8g (yield: 86.2%) of a product was obtained.
Synthesis example of P1-8
Sub2-5 (48.2 g,107.63 mmol), pd was added to Sub1-2 (28 g,102.5 mmol) 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (1051 ml) were carried out in the same manner as in the above-described synthesis example of P1-1, whereby 54.1g (yield: 82.4%) of a product was obtained.
Synthesis example of P1-13
Sub2-13 (41.7 g,93.2 mmol), pd was added to Sub1-5 (31 g,88.7 mmol) 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (910 ml) were carried out in the same manner as in the above-described synthesis example of P1-1, whereby 48.4g (yield: 76.1%) of a product was obtained.
Synthesis example of P1-19
Sub2-18 (45.9 g,92.3 mmol), pd were added to Sub1-2 (24 g,87.9 mmol) 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq),And toluene (901 ml), in the same manner as in the synthesis example of P1-1 above, 43.9g (yield: 72.4%) of a product was obtained.
Synthesis example of P1-38
Sub2-64 (44.3 g,84.6 mmol), pd was added to Sub1-2 (22 g,80.5 mmol) 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (825 ml) were carried out in the same manner as in the above-described synthesis example of P1-1, whereby 48.2g (yield: 83.6%) of a product was obtained.
Synthesis example of P2-9
Sub2-56 (28.6 g,53.1 mmol), pd was added to Sub1-10 (20 g,50.6 mmol) 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (519 ml) were carried out in the same manner as in the above-described synthesis example of P1-1, whereby 30.7g (yield: 71.3%) of a product was obtained.
Synthesis example of P2-20
Sub2-66 (28 g,48.8 mmol), pd was added to Sub1-14 (21 g,46.5 mmol) 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (477 ml) were carried out in the same manner as in the above-described synthesis example of P1-1, whereby 30.2g (yield: 68.7%) of a product was obtained.
Synthesis example of P3-8
Sub2-20 (28.3 g,50.2 mmol), pd was added to Sub1-15 (19 g,47.82 mmol) 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (490 ml) were carried out in the same manner as in the above-mentioned synthesis example of P1-1, whereby 27.5g (yield: 65.3%) of a product was obtained.
Synthesis example of P3-26
Sub2-26 (30.3 g,56.4 mmol), pd was added to Sub1-22 (18 g,53.7 mmol) 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (550 ml) were carried out in the same manner as in the above-described synthesis example of P1-1, whereby 31.5g (yield: 74.1%) of a product was obtained.
Synthesis example of P4-3
Sub2-51 (29.8 g,52.8 mmol), pd was added to Sub1-25 (20 g,50.3 mmol) 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (516 ml) were carried out in the same manner as in the above-described synthesis example of P1-1, whereby 33.8g (yield: 76.4%) of a product was obtained.
Synthesis example of P5-1
Sub2-3 (41.4 g,79.1 mmol), pd was added to Sub1-28 (31 g,74.4 mmol) 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (773 ml) were carried out in the same manner as in the above-described synthesis example of P1-1, whereby 53.5g (yield: 83.1%) of a product was obtained.
Synthesis example of P5-16
Sub2-73 (33.4 g,63.8 mmol), pd were added to Sub1-29 (25 g,60.8 mmol) 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (623 ml) were carried out in the same manner as in the above-described synthesis example of P1-1, whereby 35.9g (yield: 69.1%) of a product was obtained.
Synthesis example of P5-19
Sub2-76 (29.9 g,46.7 mmol), pd was added to Sub1-30 (19 g,44.5 mmol) 2 (dba) 3 (0.03 eq), P (t-Bu) 3 (0.06 eq), naOt-Bu (3 eq), and toluene (456 ml) were carried out in the same manner as in the above-described synthesis example of P1-1, whereby 27g (yield: 61.6%) of a product was obtained.
The FD-MS values of the compounds of the present invention prepared according to the synthesis examples described above are as in table 3 below.
TABLE 3
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Evaluation of organic electric element production
Example 1 Green organic electroluminescent element (hole transporting layer)
After forming a hole injection layer of 60nm thickness by vacuum deposition of a film of N1- (naphthalen-2-yl) -N4, N4-bis (4- (naphthalen-2-yl (phenyl) amino) phenyl) -N1-phenylbenzene-1, 4-diamine (hereinafter, abbreviated as "2-TNATA") on an ITO layer (anode) formed on a glass substrate, a hole transport layer was formed by vacuum deposition of a film of the compound P1-1 of the present invention of 60nm thickness on the hole injection layer.
The hole transporting layer was mainly composed of 4,4'-N, N' -dicarbazole-biphenyl (hereinafter abbreviated as "CBP") and tris (2-phenylpyridine) iridium (hereinafter abbreviated as "Ir (ppy)" 3 ") as a dopant, and 90:10, and a light emitting layer was vacuum deposited at a thickness of 30 nm.
Next, a hole blocking layer was formed by vacuum deposition of (1, 1' -biphenyl-4-hydroxy) bis (2-methyl-8-hydroxyquinoline) aluminum (hereinafter, abbreviated as "BAlq") on the light emitting layer at a thickness of 5nm, and a tris (8-hydroxyquinoline) aluminum (hereinafter, abbreviated as "Alq") was vacuum deposited on the hole blocking layer at a thickness of 40nm 3 ") to form an electron transport layer.
Then, liF was deposited on the electron transport layer at a thickness of 0.2nm to form an electron injection layer, and then Al was deposited at a thickness of 150nm to form a cathode.
Examples 2 to 27
An organic electroluminescent element was produced in the same manner as in example 1 above, except that the compound of the present invention described in Table 4 below was used instead of the compound P1-1 of the present invention as the hole transporting layer.
Comparative example 1
An organic electroluminescent element was produced in the same manner as in example 1 above, except that N, N '-bis (1-naphthyl) -N, N' -diphenyl- (1, 1 '-biphenyl) -4,4' -diamine (hereinafter, abbreviated as "NPB") was used as the substance of the hole transporting layer.
Comparative examples 2 to 7
An organic electroluminescent element was fabricated in the same manner as in example 1 above, except that one of the following comparative compounds ref1 to ref6 was used instead of the compound P-1 of the example of the present invention as a substance of the hole transporting layer.
<ref1><ref2><ref3>
Forward bias dc voltages were applied to the organic electroluminescent elements prepared by examples 1 to 27 and comparative examples 1 to 7 of the present invention, and Electroluminescent (EL) characteristics were measured using PR-650 of photo research company of usa. At 5000cd/m 2 In the reference brightness, the T95 lifetime was measured by a lifetime measuring device manufactured by korean pulse science (ma cscience). The measurement results are shown in table 4 below.
TABLE 4
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As can be seen from table 4, when the compound of the present invention is used as a material of the hole transporting layer, the driving voltage of the organic electric element is reduced, and both efficiency and lifetime are improved, as compared with the case of using NPB or one of the comparative compounds ref1 to ref 6.
Ref1 to ref6 as comparative compounds are each a tertiary amine structure similar to the present invention, but differ in that in ref1 and ref2, pure aryl groups are substituted for amine groups, whereas in formula 1 of the present invention, condensed rings containing fluorene moieties are substituted, and in spite of ref3 to ref6 having a structure very similar to the compounds of the present invention, ref3, ref4 and ref6 differ from the compounds of the present invention in the binding position of the linker L to the naphthalene moiety bound to the phenylene moiety, and in that ref5 differs from the compounds of the present invention in the absence of L.
To explain this in more detail, as described below, in chemical formula 1 of the present invention, the phenylene moiety directly bonded to L is referred to as a constituent 1, and the naphthalene moiety bonded to such a constituent 1 is referred to as a constituent 2.
In the compound of the present invention, the linker L and the constituent 2 are bonded to the phenylene group of the constituent 1 at the ortho (ortho) position, whereas the linker L and the constituent 2 are bonded to the ref3, ref4, and ref6 at the meta (meta) position, which is different from each other.
Further, since the linking group L of the compound of the present invention cannot be formed as a single bond, nitrogen of the amine group and constituent 1 are bound via the linking group L, whereas ref5 is nitrogen directly linked to the amine group as a phenylene group of constituent 1, which is different in this point.
Therefore, it is understood that, when the compound of the present invention is used as a material for a hole transporting layer, the compound of the present invention has a lower driving voltage and improved efficiency and life, because the compound of the present invention has a structure in which an amine group is substituted for a substituent containing a specific ring form (fluorenyl moiety, xanthene moiety, thioxanthene moiety, acridine moiety), and nitrogen of the amine group is indirectly bonded to structure 1 via a linking group L, and L and structure 2 are bonded to each other at the meta position of structure 1, as compared with the case where an amine group is substituted for only a pure aryl group, and the electrical characteristics of the element are affected by the type of the core and the type of substituent constituting the compound.
Comparison of ref1 with HOMO energy levels of the compounds P1-49, P2-25, P3-22, P5-16, P5-17 of the present invention is shown in Table 5 below.
TABLE 5
| ref 1 | P1-49 | P2-25 | P3-22 | P5-16 | P5-17 | |
| HOMO(eV) | 4.897 | 4.773 | 4.785 | 4.794 | 4.820 | 4.764 |
Referring to table 5, it is understood that the HOMO energy level values of the compounds P1 to 49, P2 to 25, P3 to 22, P5 to 16, and P5 to 17 of the present invention are higher than ref1, which suggests that holes can easily move from the hole injection layer to the light emitting layer when the compound represented by chemical formula 1 of the present invention is used as a material of the hole transporting layer according to the core structure of the compound, and thus the characteristics of the element are improved as compared to the compound of ref 1.
As described above, ref3, ref4 and ref6 and the compounds P1 to 34, P1 to 49 and P5 to 16 of the present invention differ in the positions where the linking group L on the phenylene group as the constituent 1 and the constituent 2 bind, and as a result, the compound of the present invention easily has a resonance structure as compared with the comparative compound, and therefore the element characteristics of the examples using the compound of the present invention are improved.
In addition, as already explained, the difference between comparative compound ref6 and the compounds P4 to 27 of the present invention is whether or not a linking group L is present between the N of the amine group and the constituent 1, and the HOMO values will be different due to this difference, as shown in Table 6 below.
TABLE 6
| ref 6 | P4-27 | |
| HOMO(eV) | 4.944 | 4.878 |
As is clear from table 6, the HOMO energy levels of the compounds P4 to 27 of the present invention are higher than ref6, and thus it is seen that the presence or absence of the linking group has an effect on the physical properties of the compound, and when the compound of the present invention having a high HOMO energy level is used as a material for the hole transporting layer, holes can easily move from the hole injecting layer to the light emitting layer, and therefore, the characteristics of the device are improved as compared with ref 6.
Therefore, it is understood that the types of substituents substituted with an amine group, the presence or absence of a linking group L between an N of an amine group and a constituent 1, the position of the linking group L on the constituent 1 and a constituent 2, and the like will differ depending on the physical properties (HOMO, LUMO, T1, and the like) of these compounds, and that such differences may have a significant influence on the performance of an electromechanical device.
Example 28 Green organic electroluminescent device (light-emitting auxiliary layer)
After a hole injection layer of 60nm thickness was formed by vacuum deposition of a 2-TNATA film on an ITO layer (anode) formed on a glass substrate, a hole transport layer was formed by vacuum deposition of an NPB film of 60nm thickness on the hole injection layer.
Next, a light-emitting auxiliary layer was formed by vacuum evaporation of the compound P1-2 of the present invention on the hole transport layer at a thickness of 20nm, 9, 10-bis (naphthalen-2-yl) anthracene was used as a main body on the light-emitting auxiliary layer, BD-052X (manufactured by Idemitsu kosan) was used as a dopant, and 96:4, and a light-emitting layer was vacuum deposited at a thickness of 30 nm.
Next, a hole blocking layer was formed by vacuum deposition of BAlq at a thickness of 10nm on the light emitting layer, and Alq was vacuum deposited at a thickness of 40nm on the hole blocking layer 3 To form an electron transport layer. Then, liF was deposited on the electron transport layer at a thickness of 0.2nm to form an electron injection layer, and then Al was deposited at a thickness of 150nm to form a cathode.
Examples 29 to 41
An organic electroluminescent element was produced in the same manner as in example 28 above, except that the compound of the present invention shown in Table 7 below was used as the light-emitting auxiliary layer instead of the compound P1-2 of the present invention.
Comparative example 8
An organic electroluminescent element was fabricated in the same manner as in example 28 above, except that no light-emitting auxiliary layer was formed.
Comparative examples 9 to 14
An organic electroluminescent element was produced in the same manner as in example 28 above, except that one of ref 1 to ref 6 was used as the substance of the light-emitting auxiliary layer instead of the compound P1-2 of the present invention.
The organic electroluminescent elements prepared by examples 28 to 41 and comparative examples 8 to 14 of the present invention were applied with a forward bias direct current voltage, and Electroluminescent (EL) characteristics were measured using PR-650 of photo research company of usa. At 500cd/m 2 In the reference brightness, the T95 lifetime was measured by a lifetime measuring device manufactured by korean pulse science (ma cscience). The measurement results are shown in table 7 below.
TABLE 7
As is clear from table 7 above, when the compound of the present invention is used as a material of the light-emitting auxiliary layer, the characteristics of the organic electric element are improved as compared with the case where the light-emitting auxiliary layer is not formed or one of the comparative compounds ref 1 to ref 6 is used.
That is, it is understood that the compound of the present invention has the above-described characteristics in which the amine group is substituted with a substituent having a specific ring form (fluorene moiety, xanthene moiety, thioxanthene moiety, etc.), and that the characteristics of the element can be improved even when the compound of the present invention is used as a material for a hole transporting layer or a material for a light-emitting auxiliary layer.
Therefore, it is known that the compound of the present invention can improve the charge balance in the light emitting layer, thereby improving the efficiency, and can maintain the charge balance in the light emitting layer with preventing the transfer of electrons from the light emitting layer, thereby improving the driving voltage and lifetime, and finally the above-mentioned characteristics of the compound of the present invention play a major role in improving the performance of the device.
The above description is merely illustrative, and a person skilled in the art to which the present invention pertains can make various modifications within the scope of the essential characteristics of the present invention. Therefore, the embodiments disclosed in the present specification are not intended to limit the present invention, but rather to illustrate the present invention, and the scope of the claims of the present invention is not limited by such embodiments. The scope of the invention should be construed in accordance with the appended claims and all techniques that come within the meaning and range of equivalents are intended to be embraced therein.
Claims (16)
1. A compound represented by chemical formula 1:
< chemical formula 1>
In the above-mentioned chemical formula 1,
R 1 to R 4 Independently of each other selected from the group consisting of hydrogen; heavy hydrogen; halogen; cyano group; a nitro group; c (C) 6 ～C 60 Aryl of (a); fluorenyl; c comprising at least one heteroatom of O, N, S, si and P 2 ～C 60 Heterocyclic groups of (a); c (C) 3 ～C 60 An aliphatic cyclic group of (a); c (C) 1 ～C 20 Alkyl of (a); c (C) 2 ～C 20 Alkenyl of (c); c (C) 2 ～C 20 Alkynyl of (a); c (C) 1 ～C 20 Alkoxy groups of (a); c (C) 6 ～C 20 An aryloxy group of (a); -L' -N (R) a )(R b ) A group of groups, and adjacent groups may be bonded to each other to form a ring,
a to c are integers of 0 to 4, d is an integer of 0 to 7, and R is an integer of 2 or more 1 R is respectively R 2 R is respectively R 3 R is respectively R 4 Respectively, are the same or different from each other,
r 'and R' are independently selected from hydrogen; c (C) 6 ～C 60 Aryl of (a); fluorenyl; c comprising at least one heteroatom of O, N, S, si and P 2 ～C 60 Heterocyclic groups of (a); c (C) 3 ～C 60 An aliphatic cyclic group of (a); c (C) 1 ～C 20 Alkyl of (a); c (C) 2 ～C 20 Alkenyl of (c); c (C) 2 ～C 20 Alkynyl of (a); c (C) 1 ～C 20 Alkoxy groups of (a); c 6 ～C 20 And R' may be combined with each other to form a ring,
l is selected from C 6 ～C 60 Arylene of (a); fluorenylene; c (C) 3 ～C 60 An aliphatic cyclic group of (a); c comprising at least one heteroatom of O, N, S, si and P 2 ～C 60 Heterocyclic groups of (a); a group consisting of a combination thereof,
Ar 1 is selected from C 6 ～C 60 Aryl of (a); fluorenyl; c comprising at least one heteroatom of O, N, S, si and P 2 ～C 60 Heterocyclic groups of (a); c (C) 3 ～C 60 An aliphatic cyclic group of (a); a group consisting of a combination thereof,
the above L' is selected from single bond; c (C) 6 ～C 60 Arylene of (a); fluorenylene; c (C) 3 ～C 60 An aliphatic ring of (a); and C comprising at least one heteroatom of O, N, S, si and P 2 ～C 60 Is selected from the group consisting of heterocyclic groups,
r is as described above a R is R b Independently of one another selected from the group consisting of C 6 ～C 60 Aryl of (a); fluorenyl; c comprising at least one heteroatom of O, N, S, si and P 2 ～C 60 Heterocyclic groups of (a); c 3 ～C 60 Is selected from the group consisting of aliphatic cyclic groups,
The aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, a ring formed by bonding adjacent groups to each other, a ring formed by bonding R 'and R', R 1 And R is 2 The rings formed by the combination of the two can be respectively selected from heavy hydrogen, halogen and C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted silyl, substituted with C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C 1 ～C 20 Alkylthio, C 1 ～C 20 Alkoxy, C 6 ～C 20 Aryloxy group, C 6 ～C 20 Arylthio radicals C 1 ～C 20 Alkyl, C of (2) 2 ～C 20 Alkenyl, C 2 ～C 20 Alkynyl, C 6 ～C 30 Aryl, fluorenyl, C comprising at least one heteroatom selected from the group consisting of O, N, S, si and P 2 ～C 30 Heterocyclic groups of C 3 ～C 30 Aliphatic cyclic group of (C), andone or more substituents of the group consisting of combinations thereof are further substituted.
2. The compound according to claim 1, wherein the above chemical formula 1 is represented by one of the following chemical formulas 2 to 4,
< chemical formula 4>
In the above chemical formulas 2 to 4, R 1 、R 2 、R 4 、R'、R”、Ar 1 A, b, d are as defined in claim 1.
3. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 5 or chemical formula 6,
In the above chemical formula 5 and chemical formula 6, R 1 、R 2 、R'、R”、Ar 1 A, b are as defined in claim 1,
R 5 is selected from hydrogen, heavy hydrogen, halogen, and C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted silyl, substituted with C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C 1 ～C 20 Alkylthio, C 1 ～C 20 Alkoxy, C 6 ～C 20 Aryloxy group, C 6 ～C 20 Arylthio radicals C 1 ～C 20 Alkyl, C of (2) 2 ～C 20 Alkenyl, C 2 ～C 20 Alkynyl, C 6 ～C 30 Aryl, fluorenyl, C comprising at least one heteroatom selected from the group consisting of O, N, S, si and P 2 ～C 30 Heterocyclic groups of C 3 ～C 30 And combinations thereof, and adjacent groups may be bonded to each other to form a ring,
e is an integer of 0 to 5, and R is an integer of 2 or more when e is an integer of 5 Respectively the same or different.
4. The compound according to claim 1, wherein the above chemical formula 1 is represented by one of the following chemical formulas 7 to 10,
in the above chemical formulas 7 to 10, R 1 To R 4 、R'、R”、Ar 1 L, a, c, d are as defined in claim 1,
R 11 to R 15 Independently of each other selected from hydrogen, heavy hydrogen, halogen, and C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted silyl, substituted with C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C 1 ～C 20 Alkylthio, C 1 ～C 20 Alkoxy, C 6 ～C 20 Aryloxy group, C 6 ～C 20 Arylthio radicals C 1 ～C 20 Alkyl, C of (2) 2 ～C 20 Alkenyl, C 2 ～C 20 Alkynyl, C 6 ～C 30 Aryl, fluorenyl, C comprising at least one heteroatom selected from the group consisting of O, N, S, si and P 2 ～C 30 Heterocyclic groups of C 3 ～C 30 And combinations thereof, and adjacent groups may be bonded to each other to form a ring,
in chemical formulas 7 and 8, b is an integer of 0 to 3, in chemical formulas 9 and 10, b is an integer of 0 to 4, and when b is an integer of 2 or more, R 2 Respectively, are the same or different from each other,
m, n, o and p are integers of 0 to 4, q is an integer of 0 to 3, and R is an integer of 2 or more 11 R is respectively R 12 R is respectively R 13 R is respectively R 14 R is respectively R 15 Respectively the same or different.
5. The compound according to claim 1, wherein the above chemical formula 1 is represented by one of the following chemical formulas 11 to 14,
in the above chemical formulas 11 to 14, R 1 To R 4 R ', R', a, c, d are as defined in claim 1, represent binding sites,
x is O, S, N (Ar) 1 ) Or C (R) 1 )(R 2 )，
R 5 ，R 6 ，R 11 To R 15 ，R 1 R is R 2 Independently of each other selected from hydrogen, heavy hydrogen, halogen, and C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted silyl, substituted with C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl group extractionSubstituted or unsubstituted phosphine oxides, siloxane groups, cyano groups, nitro groups, C 1 ～C 20 Alkylthio, C 1 ～C 20 Alkoxy, C 6 ～C 20 Aryloxy group, C 6 ～C 20 Arylthio radicals C 1 ～C 20 Alkyl, C of (2) 2 ～C 20 Alkenyl, C 2 ～C 20 Alkynyl, C 6 ～C 30 Aryl, fluorenyl, C comprising at least one heteroatom selected from the group consisting of O, N, S, si and P 2 ～C 30 Heterocyclic groups of C 3 ～C 30 And combinations thereof, and adjacent groups may be bonded to each other to form a ring, R 1 And R is 2 Can be combined with each other to form a ring,
ar as described above 1 Is selected from C 6 ～C 30 Aryl, fluorenyl, C comprising at least one heteroatom of O, N, S, si and P 2 ～C 30 Heterocyclic groups of C 3 ～C 30 An aliphatic cyclic group, and combinations thereof,
in chemical formula 11 and chemical formula 12, b is an integer of 0 to 3, in chemical formula 13 and chemical formula 14, b is an integer of 0 to 4, and when b is an integer of 2 or more, R 2 Respectively, are the same or different from each other,
e. m, n, o and p are each an integer of 0 to 4, f is an integer of 0 to 5, q is an integer of 0 to 3, and R is an integer of 2 or more 5 R is respectively R 6 R is respectively R 11 R is respectively R 12 R is respectively R 13 R is respectively R 14 R is respectively R 15 Respectively the same or different.
6. The compound according to claim 1, wherein the above chemical formula 1 is represented by the following chemical formula 15 or chemical formula 16,
at the upper partIn the chemical formula 15 and the chemical formula 16, R 1 、R 2 R', R ", a are as defined in claim 1,
R 5 r is R 6 Independently of each other selected from hydrogen, heavy hydrogen, halogen, and C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted silyl, substituted with C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C 1 ～C 20 Alkylthio, C 1 ～C 20 Alkoxy, C 6 ～C 20 Aryloxy group, C 6 ～C 20 Arylthio radicals C 1 ～C 20 Alkyl, C of (2) 2 ～C 20 Alkenyl, C 2 ～C 20 Alkynyl, C 6 ～C 30 Aryl, fluorenyl, C comprising at least one heteroatom selected from the group consisting of O, N, S, si and P 2 ～C 30 Heterocyclic groups of C 3 ～C 30 And combinations thereof, and adjacent groups may be bonded to each other to form a ring,
b is an integer of 0 to 3, e is an integer of 0 to 4, f is an integer of 0 to 5, and R is an integer of 2 or more when they are each 2 R is respectively R 5 R is respectively R 6 Respectively the same or different.
7. The compound according to claim 1, wherein the above chemical formula 1 is represented by one of the following chemical formulas 17 to 22,
In the above chemical formulas 17 to 22, R 1 、R 2 R', a are as defined in claim 1, which represents the binding site,
x is O, S, N (Ar) 1 ) Or C (R) 1 )(R 2 )，
R 5 、R 6 、R 11 To R 15 、R 1 R is R 2 Independently of each other selected from hydrogen, heavy hydrogen, halogen, and C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted silyl, substituted with C 1 ～C 20 Alkyl or C 6 ～C 20 Aryl-substituted or unsubstituted phosphine oxides, siloxanes, cyano groups, nitro groups, C 1 ～C 20 Alkylthio, C 1 ～C 20 Alkoxy, C 6 ～C 20 Aryloxy group, C 6 ～C 20 Arylthio radicals C 1 ～C 20 Alkyl, C of (2) 2 ～C 20 Alkenyl, C 2 ～C 20 Alkynyl, C 6 ～C 30 Aryl, fluorenyl, C comprising at least one heteroatom selected from the group consisting of O, N, S, si and P 2 ～C 30 Heterocyclic groups of C 3 ～C 30 And combinations thereof, and adjacent groups may be bonded to each other to form a ring, R 1 And R is 2 Can be combined with each other to form a ring,
ar as described above 1 Is selected from C 6 ～C 30 Aryl, fluorenyl, C comprising at least one heteroatom of O, N, S, si and P 2 ～C 30 Heterocyclic groups of C 3 ～C 30 An aliphatic cyclic group, and combinations thereof,
in chemical formulas 17 and 18, b is an integer of 0 to 3, in chemical formulas 19 to 22, b is an integer of 0 to 4, and when b is an integer of 2 or more, R 2 Respectively, are the same or different from each other,
e. m, n, o and p are each an integer of 0 to 4, f is an integer of 0 to 5, q is an integer of 0 to 3, and R is an integer of 2 or more 5 R is respectively R 6 R is respectively R 11 R is respectively R 12 R is respectively R 13 R is respectively R 14 R is respectively R 15 Respectively the same or different.
8. The compound according to claim 1, wherein Ar is 1 Is C 12 ～C 25 Aryl or fluorenyl groups of (a).
9. The compound according to claim 1, wherein the compound represented by the above chemical formula 1 is one of the following compounds:
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10. an organic electronic component comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises the compound of claim 1.
11. The organic electric device according to claim 10, wherein the organic layer includes a light-emitting layer, a hole-transporting layer between the light-emitting layer and the first electrode, and a light-emitting auxiliary layer between the hole-transporting layer and the first electrode, and wherein the compound is contained in at least one layer of the hole-transporting layer and the light-emitting auxiliary layer.
12. The organic electric element according to claim 10, wherein the organic electric element further comprises a light efficiency improving layer, the light efficiency improving layer comprising the compound according to claim 1, which is formed on both surfaces of the first electrode or the second electrode not to be in contact with the organic layer.
13. The organic electric device according to claim 10, wherein the organic layer comprises two or more stacks (stacks) comprising a hole transporting layer, a light emitting layer, and an electron transporting layer sequentially formed on the anode.
14. The organic electronic device of claim 13, wherein the organic layer further comprises a charge generation layer formed between the two or more stacks.
15. An electronic device, comprising:
a display device comprising the organic electrical element according to claim 10; and
and a control unit for driving the display device.
16. The electronic device according to claim 15, wherein the organic electronic element is an organic electroluminescent element, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting element, or a quantum dot display element.
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| Application Number | Priority Date | Filing Date | Title |
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| KR10-2021-0052990 | 2021-04-23 | ||
| KR10-2021-0057264 | 2021-05-03 | ||
| KR1020210057264A KR20220146987A (en) | 2021-04-23 | 2021-05-03 | Compound for organic electric element, organic electric element using the same, and an electronic device thereof |
| PCT/KR2022/003947 WO2022225198A1 (en) | 2021-04-23 | 2022-03-22 | Compound for organic electric element, organic electric element using same, and electronic device comprising same |
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| CN117203184A true CN117203184A (en) | 2023-12-08 |
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