WO2020184906A1 - Organic compound and organic electroluminescent device using same - Google Patents
Organic compound and organic electroluminescent device using same Download PDFInfo
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- WO2020184906A1 WO2020184906A1 PCT/KR2020/003141 KR2020003141W WO2020184906A1 WO 2020184906 A1 WO2020184906 A1 WO 2020184906A1 KR 2020003141 W KR2020003141 W KR 2020003141W WO 2020184906 A1 WO2020184906 A1 WO 2020184906A1
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- 238000002347 injection Methods 0.000 claims description 26
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- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 20
- 125000004104 aryloxy group Chemical group 0.000 claims description 17
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- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 16
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
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- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000005106 triarylsilyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
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- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Definitions
- the present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, a compound having excellent thermal stability, electrochemical stability, luminescence ability, electron injection/transport ability, and luminous efficiency by including it in at least one organic material layer. , To an organic electroluminescent device having improved characteristics such as driving voltage and lifetime.
- organic electroluminescent device In an organic electroluminescent device (hereinafter referred to as “organic EL device”), when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode and electrons are injected into the organic material layer from the cathode. When injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted.
- the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to their function.
- the light-emitting materials of the organic EL device may be classified into blue, green, and red light-emitting materials, and yellow and orange light-emitting materials for realizing better natural colors according to light emission colors.
- a host/dopant system may be used as a light emitting material.
- the dopant material can be classified into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
- a metal complex compound containing heavy atoms such as Ir and Pt.
- NPB hole blocking layer
- BCP hole blocking layer
- Alq 3 materials for the hole blocking layer and the electron transport layer
- anthracene derivatives have been reported as materials for the light emitting layer.
- metal complex compounds containing Ir such as Firpic, Ir(ppy) 3 and (acac)Ir(btp) 2 , which have advantages in terms of efficiency improvement, among the light emitting layer materials are blue, green, and red. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.
- Ir such as Firpic, Ir(ppy) 3 and (acac)Ir(btp) 2
- red is used as a phosphorescent dopant material
- CBP 4,4-dicarbazolybiphenyl
- the present invention provides a novel organic compound that can be applied to an organic electroluminescent device and can be used as a light emitting layer material, an electron transport layer material, or an electron transport auxiliary layer material having excellent thermal stability, electrochemical stability, luminescence and electron injection/transport performance. It aims to do.
- another object of the present invention is to provide an organic electroluminescent device including the novel organic compound, exhibiting a low driving voltage and high luminous efficiency, and improving lifespan.
- n is an integer of 1 to 3
- L 1 is selected from the group consisting of an arylene group of C 6 to C 40 and a heteroarylene group having 5 to 40 nuclear atoms,
- Z 1 to Z 3 are the same as or different from each other, and each independently N or CR 1 , provided that at least two of Z 1 to Z 3 are N,
- R 1 is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 Cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , C 6 to C 60 Aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 Selected from the group consisting of an arylphosphine group, a C 6 ⁇ C 60 arylphosphine oxide group and a C 6 ⁇ C 60 arylamine group, or combined with an adjacent group to
- Ar 1 and Ar 2 are the same as or different from each other, each independently selected from the group consisting of an aryl group of C 6 to C 60 and a heteroaryl group having 5 to 60 nuclear atoms,
- Arylene group and a heteroaryl group an alkyl group R 1 of said L 1, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl Group, alkyl boron group, aryl boron group, arylphosphine group, arylphosphine oxide group and arylamine group, and the aryl and heteroaryl groups of Ar 1 and Ar 2 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ⁇ C 60 Aryl group,
- the present invention is an organic electroluminescent device comprising the above-described anode, cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is represented by Formula 1 It provides an organic electroluminescent device comprising the compound.
- the compound of the present invention is excellent in thermal stability, electrochemical stability, electron transporting ability, and luminescence ability, it can be usefully applied as an organic material layer material of an organic electroluminescent device.
- the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full-color display panel or the like because the light emitting performance, driving voltage, lifespan, and efficiency are greatly improved.
- FIG. 1 is a schematic cross-sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.
- FIG. 2 is a schematic cross-sectional view of an organic electroluminescent device according to another example of the present invention.
- 300 organic material layer
- 310 hole injection layer
- the present invention is excellent in thermal stability, electrochemical stability, electron injection/transport ability, and luminescence ability, and thus a highly efficient light emitting layer material (specifically a host, more specifically an n-type host), an electron transport layer material or an electron transport auxiliary layer It provides a new compound that can be used as a material.
- a highly efficient light emitting layer material specifically a host, more specifically an n-type host
- an electron transport layer material or an electron transport auxiliary layer It provides a new compound that can be used as a material.
- the compound represented by Formula 1 according to the present invention is a 6-membered heteroaromatic substituent containing two or more N in fluorene of a spiro fluorene-annulene moiety. It includes a core structure formed by being bonded through ). Accordingly, the compound of Formula 1 according to the present invention is excellent in thermal stability, electrochemical stability, electron injection/transport performance, and luminescence performance. When the compound of Formula 1 is applied to an organic electroluminescent device, the organic electroluminescent device has a low driving voltage, high luminous efficiency and current efficiency, and has a long life.
- the spiro fluorene-annulene moiety has excellent electrochemical stability, high glass transition temperature, and thus excellent thermal stability, as well as excellent carrier transport ability, especially electron mobility. Do. Accordingly, when the compound of Formula 1 is applied to a blue organic electroluminescent device, the blue light emission efficiency of the device may be increased.
- a 6-membered heteroaromatic substituent containing two or more Ns is introduced into the above-described spiro fluorene-annulene moiety.
- the 6-membered heteroaromatic substituent containing two or more N is a monovalent triazine-based substituent, a monovalent pyrimidine-based substituent, a monovalent quinazoline substituent, etc., and has a large electron withdrawing group (EWG) )to be. Since the 6-membered heteroaromatic substituent containing two or more N has a stronger electron withdrawing power than the monovalent pyridine-based substituent, which is EWG, the electron injection and transport ability of the compound can be further maximized. I can.
- the 6-membered heteroaromatic substituent containing two or more N is spiro fluorene-annulene moiety
- the 6-membered heteroaromatic substituent is not introduced, or a pyridine-based substituent is introduced.
- the spiro fluorene-annulene compound not only the electron mobility is better, but also the glass transition temperature is higher, so that the thermal stability is better.
- the compound of the present invention is a 6-membered compound containing two or more N, unlike the spiro fluorene-annulene compound into which an arylamine group is introduced. Since the heteroaromatic substituent improves the stability and mobility of electrons, the life characteristics of the device can be increased.
- the aforementioned 6 membered heteroaromatic substituent is introduced at the benzene site in the fluorene of the spiro fluorene-annulene moiety.
- the compound of the present invention maintains the conjugation structure in the compound, unlike the compound in which the 6-membered heteroaromatic substituent is introduced at the benzene site in the annule of the spiro fluorene-annule moiety, so the stability and mobility of electrons are As a result, the lifetime characteristics of the device can be further improved.
- a 6-membered heteroaromatic substituent containing two or more N is introduced into the fluorene-annulene moiety via a linker (L 1 ).
- the linker is used as a transport channel (transporting channel) through which electrons can be transferred, and thus, not only the efficiency of the device is improved, but also the low voltage driving characteristics may be improved.
- the compound represented by Chemical Formula 1 has excellent electron transport ability and light emission properties. Accordingly, the compound of the present invention can be used as an organic material layer of an organic electroluminescent device, preferably as a material for a light-emitting layer (especially, a material for a light-emitting layer of green phosphorescence) or an electron transport layer.
- the compound of Formula 1 since the compound of Formula 1 has a high triplet energy, it can be used as a material for an auxiliary layer (hereinafter referred to as'electron transport auxiliary layer') interposed between the light emitting layer and the electron transport layer.
- the organic electroluminescent device may increase light emission and current efficiency due to a TTF (triplet-triplet fusion) effect.
- TTF triplet-triplet fusion
- the compound of Formula 1 can prevent the excitons generated in the emission layer from diffusing into the electron transport layer adjacent to the emission layer, the number of excitons contributing to light emission in the emission layer is increased, so that the luminous efficiency of the device can be improved.
- durability and stability of the device are improved, so that the life of the device can be efficiently increased.
- the organic electroluminescent device including the compound of Formula 1 can be driven at a low voltage, the lifespan of the device can be improved.
- a full-color organic light-emitting panel to which such an organic electroluminescent device is applied can also maximize performance.
- the compound represented by Formula 1 may be represented by any one of the following Formulas 2 to 4 depending on the location of the linker L 1 .
- n, L 1 , Z 1 to Z 3 , Ar 1 and Ar 2 are each as defined in Formula 1 above.
- L 1 is a divalent linker, selected from the group consisting of an arylene group of C 6 to C 40 and a heteroarylene group having 5 to 40 nuclear atoms, preferably an arylene group of C 6 to C 20 and It may be selected from the group consisting of a heteroarylene group having 5 to 20 nuclear atoms.
- L 1 include an arylene group such as a phenylene group, a biphenylene group, and a terphenylene group;
- heteroarylene groups such as a divalent dibenzofuran group, a divalent dibenzothiophene group, and a divalent fluorene group.
- L 1 may be selected from the group consisting of the following linker groups L1 to L6:
- linker groups L1 to L6 include the following L1-1 to L1-2, L2-1 to L2-3, L3-1, L4-1 to L4-4, L5-1 to L5-6, and L6- 1 to L6-5, and the like, but are not limited thereto.
- the compound of Formula 1 according to the present invention may be embodied as a compound represented by the following Formula 5 or 6, but is not limited thereto.
- Z 1 to Z 3 , Ar 1 and Ar 2 are each as defined in Formula 1,
- a is an integer from 0 to 4,
- b and c are each an integer of 0 to 3
- L 2 and L 3 are the same as or different from each other, and each independently a single bond, or is selected from the group consisting of an arylene group of C 6 to C 20 and a heteroarylene group of 5 to 20 nuclear atoms,
- Y 1 is selected from the group consisting of O, S and C(R 5 )(R 6 ),
- R 2 to R 6 are the same as or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, 3 to 40 nuclear atom heterocycloalkyl group, C 6 to C 60 aryl group, 5 to 60 nuclear atom heteroaryl group, C 1 to C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C the group of boron 60 aryl, C 6 ⁇ C 60 aryl phosphine group, is selected from the group consisting of C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ C 60
- the arylene group and heteroarylene group of L 2 and L 3 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyl of C 1 to C 40 Oxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C aryl phosphine oxide 60 group and a C 6 ⁇ C 60 aryl group is un
- the compound represented by Formula 1 according to the present invention may be embodied as a compound represented by any one of the following Formulas 7 to 12, but is not limited thereto.
- Z 1 to Z 3 , Ar 1 and Ar 2 are each as defined in Formula 1,
- R 5 and R 6 are the same as or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, 3 to 40 nuclear atom heterocycloalkyl group, C 6 to C 60 aryl group, 5 to 60 nuclear atom heteroaryl group, C 1 to C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C group of 60 arylboronic, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ C 60 is selected from the group consisting of
- Z 1 to Z 3 are the same as or different from each other, and each independently N or CR 1 , provided that at least two of Z 1 to Z 3 are N.
- R 1 is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 to C 60 aryl group, 5 to 60 nuclear atom heteroaryl group, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phos
- the condensed ring may be a C 6 ⁇ C 20 condensed aromatic ring, or a 5 to 20 membered condensed heteroaromatic ring, and the heterocycloalkyl group, heteroaryl group and condensed heteroaromatic ring are each N, S , O and Se may contain at least one hetero atom selected from the group consisting of.
- Z 1 to Z 3 are all N.
- R 1 is a group consisting of hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 20 alkyl group, C 6 to C 20 aryl group, and heteroaryl group having 5 to 20 nuclear atoms It may be selected from, or may be combined with an adjacent group Ar 1 and/or Ar 2 to form a condensed ring of C 6 ⁇ C 20 .
- Ar 1 and Ar 2 are the same as or different from each other, and each independently selected from the group consisting of an aryl group of C 6 to C 60 and a heteroaryl group having 5 to 60 nuclear atoms , Specifically, each independently may be selected from the group consisting of an aryl group of C 6 to C 20 and a heteroaryl group having 5 to 20 nuclear atoms.
- the heteroaryl group may each include at least one hetero atom selected from the group consisting of N, S, O, and Se.
- Ar 1 and Ar 2 are the same as or different from each other, and each may be independently selected from the group consisting of a phenyl group, a biphenyl group, a monovalent dibenzofuran group, and a monovalent dibenzothiophene group.
- the moiety may be selected from the group consisting of the following substituents EWG1 to EWG17:
- Aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, arylphosphine group, arylphosphine oxide group and arylamine group, and the aryl and heteroaryl groups of Ar 1 and Ar 2 are each independently deuterium , Halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, 3 to 40 nuclear atoms Heterocycloalkyl group of,
- the heterocycloalkyl group and the heteroaryl group may each include one or more heteroatoms selected from the group consisting of N, S, O, and Se.
- the compound represented by Formula 1 according to the present invention described above may be further specified as compounds (1) to (121), but is not limited thereto.
- alkyl refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
- alkenyl refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon double bonds. Examples thereof include vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl), and the like, but is not limited thereto.
- alkynyl refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.
- cycloalkyl refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
- examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.
- heterocycloalkyl refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or a hetero atom such as Se.
- heterocycloalkyl include morpholine and piperazine, but are not limited thereto.
- aryl refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined.
- a form in which two or more rings are simply attached to each other or condensed may be included. Examples of such aryl include phenyl, naphthyl, phenanthryl, and anthryl, but are not limited thereto.
- heteroaryl refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, one or more carbons, preferably 1 to 3 carbons in the ring are substituted with heteroatoms such as N, O, S or Se.
- heteroatoms such as N, O, S or Se.
- a form in which two or more rings are simply attached to each other or condensed may be included, and further, a form condensed with an aryl group may be included.
- heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, phenoxathienyl, indolizinyl, indolyl ( indolyl), purinyl, quinolyl, benzothiazole, polycyclic rings such as carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
- alkyloxy is a monovalent substituent represented by R'O-, wherein R'refers to alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure It may include. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
- aryloxy is a monovalent substituent represented by RO-, and R means an aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.
- alkylsilyl refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and includes mono- as well as di- and tri-alkylsilyl.
- arylsilyl refers to silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as di- and tri-arylsilyl as well as mono-.
- alkyl boron group refers to a boron group substituted with an alkyl having 1 to 40 carbon atoms
- aryl boron group refers to a boron group substituted with an aryl having 6 to 60 carbon atoms.
- alkylphosfinyl group refers to a phosphine group substituted with an alkyl having 1 to 40 carbon atoms, and includes not only mono- but also di-alkylphosfinyl groups.
- arylphosphinyl group refers to a phosphine group substituted with a monoaryl or diaryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosfinyl groups.
- arylamine refers to an amine substituted with an aryl having 6 to 40 carbon atoms, and includes mono- as well as di-arylamine.
- organic electroluminescent device (hereinafter, referred to as “organic EL device”) including the compound represented by Formula 1 above.
- the organic electroluminescent device includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers is It includes a compound represented by Formula 1.
- the compound may be used alone, or two or more may be used in combination.
- the one or more organic material layers may include any one or more of a hole injection layer, a hole transport layer, an emission layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, of which at least one organic material layer is represented by Formula 1 above. Contains compounds. Specifically, the organic material layer including the compound of Formula 1 may be selected from the group consisting of a light emitting layer, an electron transport layer, and an electron transport auxiliary layer.
- the at least one organic material layer includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer
- the electron transport layer includes the compound represented by Formula 1.
- the compound represented by Formula 1 is an electron transport layer material and is included in the organic electroluminescent device.
- the organic electroluminescent device of the present invention because of the compound of Formula 1, electrons are easily injected from the cathode or electron injection layer to the electron transport layer, and can quickly move from the electron transport layer to the light emitting layer, and thus, the binding force of holes and electrons in the light emitting layer Is high. Therefore, the organic electroluminescent device of the present invention is excellent in luminous efficiency, power efficiency, and brightness.
- the compound of Formula 1 has excellent thermal stability and electrochemical stability, and can improve the performance of an organic electroluminescent device.
- the one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer
- the electron transport auxiliary layer comprises the compound represented by Formula 1 Include.
- the compound represented by Formula 1 is included in the organic electroluminescent device as an electron transport auxiliary layer material.
- the compound of Formula 1 has a high triplet energy.
- the efficiency of the organic electroluminescent device may be increased due to the TTF (triplet-triplet fusion) effect.
- the compound of Formula 1 can prevent the excitons generated in the emission layer from being diffused into the electron transport layer adjacent to the emission layer. Accordingly, the number of excitons contributing to light emission in the light emitting layer is increased, so that the luminous efficiency of the device can be improved, the durability and stability of the device are improved, so that the life of the device can be effectively increased.
- the one or more organic material layers include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer
- the emission layer includes a host material and a dopant material, wherein the chemical formula It may contain the compound of 1.
- the light emitting layer of the present invention may include a compound known in the art other than the compound of Formula 1 as a host.
- the host may include a p-type host and an n-type host.
- the n-type host includes the compound of Formula 1.
- the p-type host is a host material having a p-type property, specifically, a material having better hole transport properties than an electron transport property, and a material having a high hole injection or transport property, that is, a material having a high hole conductivity.
- the p-type host usable in the present invention may be used without limitation as long as it is a material having a high hole conductivity generally known in the art.
- a carbazole derivative or the like may be used, but is not limited thereto.
- the use ratio of the p-type host and the n-type host may be a weight ratio of 1:99 to 99:1, specifically, a weight ratio of 30:70 to 70:30.
- the content of the host may be about 70 to 99.9% by weight based on the total amount of the light emitting layer, and the content of the dopant may be about 0.1 to 30% by weight based on the total amount of the light emitting layer.
- the compound represented by Formula 1 is a light emitting layer material, preferably a green, blue and red phosphorescent host material, more preferably a green phosphorescent host material, and is included in the organic electroluminescent device.
- the efficiency luminance and power efficiency
- lifespan luminance
- driving voltage thermal stability
- the like of the organic electroluminescent device can be improved.
- the compound represented by Formula 1 is preferably included in the organic electroluminescent device as a green and/or red phosphorescent host, fluorescent host, or dopant material.
- the compound represented by Chemical Formula 1 of the present invention is a green phosphorescent host material for a light emitting layer having high efficiency.
- the structure of the organic electroluminescent device of the present invention is not particularly limited, but, for example, an anode 100, one or more organic material layers 300, and a cathode 200 may be sequentially stacked on a substrate (FIGS. 1 and 2 Reference). In addition, it may have a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.
- the organic electroluminescent device includes an anode 100, a hole injection layer 310, a hole transport layer 320, a light emitting layer 330, an electron transport layer 340, and
- the cathode 200 may have a sequentially stacked structure.
- an electron injection layer 350 may be positioned between the electron transport layer 340 and the cathode 200.
- an electron transport auxiliary layer (not shown) may be positioned between the emission layer 330 and the electron transport layer 340.
- At least one of the organic material layers 300 contains a compound represented by Formula 1 above. Except for including, it can be manufactured by forming an organic material layer and an electrode using materials and methods known in the art.
- the organic material layer may be formed by a vacuum deposition method or a solution coating method.
- the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer method.
- the substrate usable in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.
- examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; Conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
- metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof
- Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb
- Conductive polymers such as polythiophene, poly
- examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; And a multilayered material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
- the glass substrate coated with a thin film of ITO (Indium tin oxide) with a thickness of 1500 ⁇ was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonically clean with a solvent such as isopropyl alcohol, acetone, methanol, etc., dry, transfer to a UV OZONE cleaner (Power Sonic 405, Hwashin Tech), and then use UV for 5 minutes. It was cleaned and the substrate was transferred to a vacuum evaporator.
- ITO Indium tin oxide
- DS-205 (80 nm) / NPB (15 nm) / 95 wt% of ADN + 5 wt% of DS-405 (30 nm) / Compound 2 (30 nm) / LiF (1 nm ) / Al (200 nm) was stacked in order to prepare an organic electroluminescent device.
- the structure of NPB and ADN used at this time is as follows, and DS-205 and DS-405 are Doosan Electronics BG products.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of the compound 2 used as the electron transport layer material when forming the electron transport layer in Example 1.
- Example 1 when forming the electron transport layer, a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq 3 was deposited at 30 nm instead of the compound 2 used as the electron transport layer material.
- the structure of Alq 3 used at this time is as follows.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound A was used instead of Compound 2 used in Example 1.
- the structure of Compound A used at this time is as follows.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound B was used instead of Compound 2 used in Example 1.
- the structure of compound B used at this time is as follows.
- Example 1 Compound 2 3.9 450 9.2 Example 2 Compound 3 3.9 452 9.0 Example 3 Compound 10 3.6 451 8.9 Example 4 Compound 23 4.3 452 9.3 Example 5 Compound 34 3.6 450 8.6 Example 6 Compound 42 3.5 452 9.4 Example 7 Compound 59 3.8 451 8.2 Example 8 Compound 62 3.8 452 8.9 Example 9 Compound 66 3.8 451 8.7 Example 10 Compound 80 3.3 452 9.1 Example 11 Compound 91 3.4 450 9.2 Example 12 Compound 100 3.7 451 9.5 Example 13 Compound 109 3.5 452 9.0 Comparative Example 1 Alq 3 4.8 457 5.8 Comparative Example 2 A 4.5 458 6.5 Comparative Example 3 B 4.6 457 7.1
- the blue organic electroluminescent devices of Examples 1 to 13 using the compound according to the present invention as an electron transport layer material were the blue organic electroluminescent devices of Comparative Example 1 in which Alq 3 was applied as the electron transport layer material.
- the glass substrate coated with a thin film of ITO (Indium tin oxide) with a thickness of 1500 ⁇ was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonically clean with a solvent such as isopropyl alcohol, acetone, methanol, etc., dry, transfer to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and clean the substrate for 5 minutes using UV And transferred the substrate to a vacuum evaporator.
- ITO Indium tin oxide
- NPB, ADN and Alq 3 used at this time are as follows, and DS-205 and DS-405 are Doosan Electronics BG products.
- a blue organic EL device was manufactured in the same manner as in Example 14, except that the compounds shown in Table 2 were used as electron transport auxiliary layer materials instead of compound 2 used as the electron transport auxiliary layer material in Example 14. I did.
- Blue organic EL was carried out in the same manner as in Example 14, except that the compound 2 used as the electron transport auxiliary layer material in Example 14 was not used, and Alq 3 as the electron transport layer material was deposited at 30 nm instead of 25 nm. The device was fabricated.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 14, except that Compound A was used instead of Compound 1 in Example 14.
- the structure of Compound A used at this time is as described in Comparative Example 2.
- a blue organic electroluminescent device was manufactured in the same manner as in Example 14, except that Compound B was used instead of Compound 1 in Example 14.
- the structure of Compound B used at this time is as described in Comparative Example 3.
- Example 14 Compound 2 3.3 450 9.3 Example 15 Compound 5 3.2 450 9.2 Example 16 Compound 13 3.5 452 8.8 Example 17 Compound 15 3.5 451 9.2 Example 18 Compound 28 3.8 450 9.4 Example 19 Compound 29 4.0 450 8.5 Example 20 Compound 45 3.4 451 8.9 Example 21 Compound 49 3.3 450 9.0 Example 22 Compound 73 3.5 451 9.2 Example 23 Compound 76 3.6 452 8.3 Example 24 Compound 94 3.7 450 9.2 Example 25 Compound 96 3.7 451 9.3 Example 26 Compound 103 3.5 450 9.3 Example 27 Compound 113 3.3 450 8.5 Comparative Example 4 - 4.6 455 6.2 Comparative Example 5 A 4.5 455 6.8 Comparative Example 6 B 4.2 456 7.2
- the blue organic EL device of Examples 14 to 27 using the compound according to the present invention as an electron transport auxiliary layer material is the blue organic electroluminescent device of Comparative Example 4 without an electron transport auxiliary layer, and the bonding position of the substituent.
- Current efficiency compared to the blue organic EL device of Comparative Example 5 in which a compound of which is different is used as an electron transport auxiliary layer material, and the blue organic EL device of Comparative Example 6 in which a compound having a substituent directly bonded without a linker is used as an electron transport auxiliary layer material. And it was found that exhibiting excellent performance in terms of driving voltage.
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Abstract
The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using same and, more particularly, to a compound having excellent thermal stability, electrochemical stability, light-emitting ability, and hole/electron transport ability, and an organic electroluminescent device including the compound in one or more organic material layers so as to have improved properties of light-emitting efficiency, driving voltage, lifespan and the like.
Description
본 발명은 신규한 유기 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로, 보다 상세하게는 열적 안정성, 전기화학적 안정성, 발광 능력, 전자 주입/수송 능력이 우수한 화합물 및 이를 하나 이상의 유기물층에 포함함으로써 발광효율, 구동 전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound and an organic electroluminescent device using the same, and more particularly, a compound having excellent thermal stability, electrochemical stability, luminescence ability, electron injection/transport ability, and luminous efficiency by including it in at least one organic material layer. , To an organic electroluminescent device having improved characteristics such as driving voltage and lifetime.
유기 전계 발광 소자(이하, '유기 EL소자'라 함)는 두 전극 사이에 전압을 걸어주면 양극에서는 정공이 유기물층으로 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 이때, 유기물층으로 사용되는 물질은 그 기능에 따라, 발광물질, 정공주입 물질, 정공수송 물질, 전자수송 물질, 전자주입 물질 등으로 분류될 수 있다.In an organic electroluminescent device (hereinafter referred to as “organic EL device”), when a voltage is applied between two electrodes, holes are injected into the organic material layer from the anode and electrons are injected into the organic material layer from the cathode. When injected holes and electrons meet, excitons are formed, and when these excitons fall to the ground state, light is emitted. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to their function.
유기 EL 소자의 발광 물질은 발광색에 따라 청색, 녹색, 적색 발광 물질과, 보다 나은 천연색을 구현하기 위한 노란색 및 주황색 발광 물질로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도펀트 계를 사용할 수 있다.The light-emitting materials of the organic EL device may be classified into blue, green, and red light-emitting materials, and yellow and orange light-emitting materials for realizing better natural colors according to light emission colors. In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system may be used as a light emitting material.
도펀트 물질은 유기 물질을 사용하는 형광 도펀트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도펀트로 나눌 수 있다. 이때, 인광 재료는 이론적으로 형광 재료에 비해 4배까지 발광 효율이 높기 때문에, 인광 도펀트 뿐만 아니라 인광 호스트 재료들에 대한 연구도 많이 진행되고 있다.The dopant material can be classified into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the phosphorescent material theoretically has a luminous efficiency up to four times higher than that of the fluorescent material, many studies on phosphorescent host materials as well as phosphorescent dopants are being conducted.
현재까지 정공주입층, 정공수송층. 정공 차단층, 전자수송층 재료로는 NPB, BCP, Alq3 등이 널리 알려져 있으며, 발광층 재료로는 안트라센 유도체들이 보고되고 있다. 특히, 발광층 재료 중 효율 향상 측면에서 장점을 가지고 있는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색(blue), 녹색(green), 적색(red)의 인광 도판트 재료로 사용되고 있으며, 4,4-디카바졸리비페닐(4,4-dicarbazolybiphenyl, CBP)은 인광 호스트 재료로 사용되고 있다.Until now, the hole injection layer and the hole transport layer. As materials for the hole blocking layer and the electron transport layer, NPB, BCP, and Alq 3 are widely known, and anthracene derivatives have been reported as materials for the light emitting layer. In particular, metal complex compounds containing Ir such as Firpic, Ir(ppy) 3 and (acac)Ir(btp) 2 , which have advantages in terms of efficiency improvement, among the light emitting layer materials are blue, green, and red. (red) is used as a phosphorescent dopant material, and 4,4-dicarbazolybiphenyl (CBP) is used as a phosphorescent host material.
그러나 종래의 유기물층 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮아 열적 안정성이 매우 좋지 않기 때문에, 유기 전계 발광 소자의 수명 측면에서 만족할 만한 수준이 되지 못하고 있다. 따라서, 성능이 뛰어난 유기물층 재료의 개발이 요구되고 있다.However, conventional organic material layer materials have an advantage in terms of light emission characteristics, but their thermal stability is not very good due to a low glass transition temperature, and thus, they are not at a satisfactory level in terms of the lifespan of an organic electroluminescent device. Therefore, there is a demand for the development of an organic material layer material having excellent performance.
본 발명은 유기 전계 발광 소자에 적용할 수 있으며, 열안정성, 전기화학적 안정성, 발광능 및 전자 주입/수송능이 우수한 발광층 재료나 전자 수송층 재료 또는 전자수송 보조층 재료로 사용될 수 있는 신규 유기 화합물을 제공하는 것을 목적으로 한다. The present invention provides a novel organic compound that can be applied to an organic electroluminescent device and can be used as a light emitting layer material, an electron transport layer material, or an electron transport auxiliary layer material having excellent thermal stability, electrochemical stability, luminescence and electron injection/transport performance. It aims to do.
또한, 본 발명은 상기 신규 유기 화합물을 포함하여 낮은 구동 전압과 높은 발광 효율을 나타내며 수명이 향상되는 유기 전계 발광 소자를 제공하는 것을 또 다른 목적으로 한다.In addition, another object of the present invention is to provide an organic electroluminescent device including the novel organic compound, exhibiting a low driving voltage and high luminous efficiency, and improving lifespan.
상기한 목적을 달성하기 위해, 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:In order to achieve the above object, the present invention provides a compound represented by the following formula 1:
(상기 화학식 1에서, (In Formula 1,
n은 1 내지 3의 정수이고,n is an integer of 1 to 3,
L1은 C6~C40의 아릴렌기 및 핵원자수 5 내지 40의 헤테로아릴렌기로 이루어진 군에서 선택되고,L 1 is selected from the group consisting of an arylene group of C 6 to C 40 and a heteroarylene group having 5 to 40 nuclear atoms,
Z1 내지 Z3는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 CR1이고, 다만 Z1 내지 Z3 중 적어도 2개는 N이며,Z 1 to Z 3 are the same as or different from each other, and each independently N or CR 1 , provided that at least two of Z 1 to Z 3 are N,
R1은 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 또는 인접한 기와 결합하여 축합 고리를 형성하고,R 1 is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 Cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , C 6 to C 60 Aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 Selected from the group consisting of an arylphosphine group, a C 6 ~ C 60 arylphosphine oxide group and a C 6 ~ C 60 arylamine group, or combined with an adjacent group to form a condensed ring,
Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택되며,Ar 1 and Ar 2 are the same as or different from each other, each independently selected from the group consisting of an aryl group of C 6 to C 60 and a heteroaryl group having 5 to 60 nuclear atoms,
상기 L1의 아릴렌기와 헤테로아릴렌기, R1의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기와 아릴아민기, 및 Ar1 및 Ar2의 아릴기와 헤테로아릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이함).Arylene group and a heteroaryl group, an alkyl group R 1 of said L 1, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl Group, alkyl boron group, aryl boron group, arylphosphine group, arylphosphine oxide group and arylamine group, and the aryl and heteroaryl groups of Ar 1 and Ar 2 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ~ C 60 Aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkylsilyl group, C 6 to C 60 aryl silyl group, C 1 ~ C 40 group, the alkyl boron C 6 ~ C group 60 arylboronic of, C 6 ~ aryl phosphine oxide of C 60 aryl phosphine group, C 6 ~ C 60 of the group, and a C 6 ~ C It is substituted or unsubstituted with one or more substituents selected from the group consisting of 60 arylamine groups, and in this case, when the substituents are plural, they are the same or different from each other).
또한, 본 발명은 전술한 양극, 음극, 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.In addition, the present invention is an organic electroluminescent device comprising the above-described anode, cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is represented by Formula 1 It provides an organic electroluminescent device comprising the compound.
본 발명의 화합물은 열적 안정성, 전기화학적 안정성, 전자 수송능, 발광능 등이 우수하기 때문에 유기 전계 발광 소자의 유기물층 재료로 유용하게 적용될 수 있다.Since the compound of the present invention is excellent in thermal stability, electrochemical stability, electron transporting ability, and luminescence ability, it can be usefully applied as an organic material layer material of an organic electroluminescent device.
또한, 본 발명의 화합물을 유기물층에 포함하는 유기 전계 발광 소자는 발광성능, 구동전압, 수명, 효율 등의 측면이 크게 향상되어 풀 칼라 디스플레이 패널 등에 효과적으로 적용될 수 있다.In addition, the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full-color display panel or the like because the light emitting performance, driving voltage, lifespan, and efficiency are greatly improved.
도 1은 본 발명의 일례에 따른 유기 전계 발광 소자를 개략적으로 나타낸 단면도이다.1 is a schematic cross-sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.
도 2는 본 발명의 다른 일례에 따른 유기 전계 발광 소자를 개략적으로 나타낸 단면도이다.2 is a schematic cross-sectional view of an organic electroluminescent device according to another example of the present invention.
** 부호의 설명 ***** Explanation of sign ***
100: 양극, 200: 음극,100: anode, 200: cathode,
300: 유기물층, 310: 정공주입층,300: organic material layer, 310: hole injection layer,
320: 정공수송층, 330: 발광층,320: hole transport layer, 330: light emitting layer,
340: 전자수송층, 350: 전자주입층340: electron transport layer, 350: electron injection layer
이하, 본 발명을 상세히 설명한다. Hereinafter, the present invention will be described in detail.
<신규 화합물><New compound>
본 발명은 열안정성, 전기화학적 안정성, 전자 주입/수송능, 발광능이 우수하여 유기 전계 발광 소자의 고효율 발광층 재료(구체적으로 호스트, 더 구체적으로 n형 호스트)나, 전자수송층 재료 또는 전자수송 보조층 재료로 사용될 수 있는 신규 화합물을 제공한다.The present invention is excellent in thermal stability, electrochemical stability, electron injection/transport ability, and luminescence ability, and thus a highly efficient light emitting layer material (specifically a host, more specifically an n-type host), an electron transport layer material or an electron transport auxiliary layer It provides a new compound that can be used as a material.
구체적으로, 본 발명에 따른 화학식 1로 표시되는 화합물은 스파이로 플루오렌-애뉼렌 모이어티(spiro fluorene-annulene moiety)의 플루오렌에 2개 이상의 N을 함유하는 6원 헤테로방향족 치환체가 링커(Linker)를 통해 결합되어 이루어진 코어 구조를 포함한다. 이에 따라, 본 발명에 따른 화학식 1의 화합물은 열안정성, 전기화학적 안정성, 전자 주입/수송능, 발광능이 우수하다. 이러한 화학식 1의 화합물을 유기 전계 발광 소자에 적용할 경우, 유기 전계 발광 소자는 낮은 구동전압과 높은 발광 효율 및 전류 효율을 가지며, 장수명을 갖는다. Specifically, the compound represented by Formula 1 according to the present invention is a 6-membered heteroaromatic substituent containing two or more N in fluorene of a spiro fluorene-annulene moiety. It includes a core structure formed by being bonded through ). Accordingly, the compound of Formula 1 according to the present invention is excellent in thermal stability, electrochemical stability, electron injection/transport performance, and luminescence performance. When the compound of Formula 1 is applied to an organic electroluminescent device, the organic electroluminescent device has a low driving voltage, high luminous efficiency and current efficiency, and has a long life.
상기 화학식 1로 표시되는 화합물에서, 스파이로 플루오렌-애뉼렌 모이어티는 전기화학적 안정성이 매우 우수하고, 유리전이온도가 높아 열적 안정성이 우수할 뿐만 아니라, 캐리어 수송 능력, 특히 전자 이동성이 매우 우수하다. 따라서, 상기 화학식 1의 화합물을 청색 유기 전계 발광 소자에 적용할 경우, 소자의 청색 발광 효율이 상승될 수 있다.In the compound represented by Chemical Formula 1, the spiro fluorene-annulene moiety has excellent electrochemical stability, high glass transition temperature, and thus excellent thermal stability, as well as excellent carrier transport ability, especially electron mobility. Do. Accordingly, when the compound of Formula 1 is applied to a blue organic electroluminescent device, the blue light emission efficiency of the device may be increased.
또, 상기 화학식 1의 화합물은 전술한 스파이로 플루오렌-애뉼렌 모이어티에 2개 이상의 N을 함유하는 6원의 헤테로방향족 치환체가 도입된다. 여기서, 2개 이상의 N을 함유하는 6원의 헤테로방향족 치환체는 1가의 트리아진계 치환체, 1가의 피리미딘계 치환체, 1가의 퀴나졸린 치환체 등으로, 전자 흡수성이 큰 전자끌개기(electron withdrawing group, EWG)이다. 이러한 2개 이상의 N을 함유하는 6원의 헤테로방향족 치환체는 EWG인 1가의 피리딘계 치환체에 비해 전자를 끌어당기는 힘(electron withdrawing power)이 더 강하기 때문에, 화합물의 전자 주입 및 수송 능력을 더 극대화시킬 수 있다. 이러한 2개 이상의 N을 함유하는 6원의 헤테로 방향족 치환체가 스파이로 플루오렌-애뉼렌 모이어티에 된 본 발명의 화합물은 6원의 헤테로 방향족 치환체가 비(非)도입되거나, 또는 피리딘계 치환체가 도입된 스파이로 플루오렌-애뉼렌 화합물에 비해, 전자 이동성이 더 우수할 뿐만 아니라, 유리전이온도도 더 높아 열적 안정성이 더 우수하다. 또한, 전자수송 영역(예, 전자수송층, 전자수송 보조층 등)에서, 본 발명의 화합물은 아릴아민기가 도입된 스파이로 플루오렌-애뉼렌 화합물과 달리, 2개 이상의 N을 함유하는 6원의 헤테로방향족 치환체가 전자의 안정성 및 이동성을 향상시키기 때문에, 소자의 수명 특성이 증가될 수 있다. Further, in the compound of Formula 1, a 6-membered heteroaromatic substituent containing two or more Ns is introduced into the above-described spiro fluorene-annulene moiety. Here, the 6-membered heteroaromatic substituent containing two or more N is a monovalent triazine-based substituent, a monovalent pyrimidine-based substituent, a monovalent quinazoline substituent, etc., and has a large electron withdrawing group (EWG) )to be. Since the 6-membered heteroaromatic substituent containing two or more N has a stronger electron withdrawing power than the monovalent pyridine-based substituent, which is EWG, the electron injection and transport ability of the compound can be further maximized. I can. In the compound of the present invention in which the 6-membered heteroaromatic substituent containing two or more N is spiro fluorene-annulene moiety, the 6-membered heteroaromatic substituent is not introduced, or a pyridine-based substituent is introduced. Compared to the spiro fluorene-annulene compound, not only the electron mobility is better, but also the glass transition temperature is higher, so that the thermal stability is better. In addition, in the electron transport region (e.g., an electron transport layer, an electron transport auxiliary layer, etc.), the compound of the present invention is a 6-membered compound containing two or more N, unlike the spiro fluorene-annulene compound into which an arylamine group is introduced. Since the heteroaromatic substituent improves the stability and mobility of electrons, the life characteristics of the device can be increased.
게다가, 전술한 6원의 헤테로방향족 치환체는 스파이로 플루오렌-애뉼렌 모이어티의 플루오렌 내 벤젠 부위에 도입된다. 이러한 본 발명의 화합물은 6원의 헤테로방향족 치환체가 스파이로 플루오렌-애뉼렌 모이어티의 애뉼렌 내 벤젠 부위에 도입된 화합물과 달리, 화합물 내 conjugation 구조를 유지하기 때문에, 전자의 안정성 및 이동성이 향상되어 소자의 수명 특성이 더 향상될 수 있다. In addition, the aforementioned 6 membered heteroaromatic substituent is introduced at the benzene site in the fluorene of the spiro fluorene-annulene moiety. The compound of the present invention maintains the conjugation structure in the compound, unlike the compound in which the 6-membered heteroaromatic substituent is introduced at the benzene site in the annule of the spiro fluorene-annule moiety, so the stability and mobility of electrons are As a result, the lifetime characteristics of the device can be further improved.
아울러, 본 발명의 화합물은 2개 이상의 N을 함유하는 6원의 헤테로방향족 치환체가 링커(L1)를 통해 스파이로 플루오렌-애뉼렌 모이어티에 도입된다. 여기서, 링커는 전자를 전달할 수 있는 수송 채널(이동 채널, transporting channel)로 이용되고, 이로 인해 소자의 효율이 향상될 뿐만 아니라, 저전압 구동 특성이 향상될 수 있다. In addition, in the compound of the present invention, a 6-membered heteroaromatic substituent containing two or more N is introduced into the fluorene-annulene moiety via a linker (L 1 ). Here, the linker is used as a transport channel (transporting channel) through which electrons can be transferred, and thus, not only the efficiency of the device is improved, but also the low voltage driving characteristics may be improved.
전술한 바와 같이, 상기 화학식 1로 표시되는 화합물은 전자 수송 능력 및 발광 특성이 우수하다. 따라서, 본 발명의 화합물은 유기 전계 발광 소자의 유기물층, 바람직하게 발광층 재료(특히, 그린 인광의 발광층 재료)나 전자 수송층 재료로 사용될 수 있다. 또한, 상기 화학식 1의 화합물은 높은 삼중항 에너지를 갖고 있기 때문에, 발광층과 전자 수송층 사이에 개재(介在)된 보조층(이하, '전자수송 보조층') 재료로 사용될 수 있다. 특히, 상기 화학식 1의 화합물이 전자수송 보조층 재료로 유기 전계 발광 소자에 포함될 경우, 유기 전계 발광 소자는 TTF(triplet-triplet fusion) 효과로 인해 발광 및 전류 효율이 상승될 수 있다. 또한, 상기 화학식 1의 화합물이 발광층에서 생성된 엑시톤이 발광층에 인접하는 전자수송층으로 확산되는 것을 방지할 수 있기 때문에, 발광층 내에서 발광에 기여하는 엑시톤의 수가 증가되어 소자의 발광 효율이 개선될 수 있고, 소자의 내구성 및 안정성이 향상되어 소자의 수명이 효율적으로 증가될 수 있다. 게다가, 상기 화학식 1의 화합물을 포함하는 유기 전계 발광 소자는 저전압 구동이 가능하기 때문에, 소자의 수명이 개선될 수 있다. 이러한 유기 전계 발광 소자가 적용된 풀 칼라 유기 발광 패널도 성능이 극대화될 수 있다.As described above, the compound represented by Chemical Formula 1 has excellent electron transport ability and light emission properties. Accordingly, the compound of the present invention can be used as an organic material layer of an organic electroluminescent device, preferably as a material for a light-emitting layer (especially, a material for a light-emitting layer of green phosphorescence) or an electron transport layer. In addition, since the compound of Formula 1 has a high triplet energy, it can be used as a material for an auxiliary layer (hereinafter referred to as'electron transport auxiliary layer') interposed between the light emitting layer and the electron transport layer. Particularly, when the compound of Formula 1 is included in an organic electroluminescent device as an electron transport auxiliary layer material, the organic electroluminescent device may increase light emission and current efficiency due to a TTF (triplet-triplet fusion) effect. In addition, since the compound of Formula 1 can prevent the excitons generated in the emission layer from diffusing into the electron transport layer adjacent to the emission layer, the number of excitons contributing to light emission in the emission layer is increased, so that the luminous efficiency of the device can be improved. In addition, durability and stability of the device are improved, so that the life of the device can be efficiently increased. In addition, since the organic electroluminescent device including the compound of Formula 1 can be driven at a low voltage, the lifespan of the device can be improved. A full-color organic light-emitting panel to which such an organic electroluminescent device is applied can also maximize performance.
상기 화학식 1로 표시되는 화합물은 링커인 L1의 도입 위치에 따라 하기 화학식 2 내지 4 중 어느 하나로 표시될 수 있다.The compound represented by Formula 1 may be represented by any one of the following Formulas 2 to 4 depending on the location of the linker L 1 .
상기 화학식 2 내지 4에서,In Formulas 2 to 4,
n, L1, Z1 내지 Z3, Ar1 및 Ar2는 각각 상기 화학식 1에서 정의한 바와 같다.n, L 1 , Z 1 to Z 3 , Ar 1 and Ar 2 are each as defined in Formula 1 above.
상기 화학식 1로 표시되는 화합물에서, n은 1 내지 3의 정수이다. 또, L1은 2가의 연결기(linker)로서, C6~C40의 아릴렌기 및 핵원자수 5 내지 40의 헤테로아릴렌기로 이루어진 군에서 선택되고, 바람직하게 C6~C20의 아릴렌기 및 핵원자수 5 내지 20의 헤테로아릴렌기로 이루어진 군에서 선택될 수 있다. L1의 구체적인 예를 들면, 페닐렌기, 바이페닐렌기, 터페닐렌기(terphenylene group) 등과 같은 아릴렌기; 2가의 디벤조퓨란기, 2가의 디벤조싸이오펜기, 2가의 플루오렌기 등과 같은 헤테로아릴렌기가 있다. 일례에 따르면, L1은 하기 링커기 L1 내지 L6으로 이루어진 군에서 선택될 수 있다:In the compound represented by Formula 1, n is an integer of 1 to 3. In addition, L 1 is a divalent linker, selected from the group consisting of an arylene group of C 6 to C 40 and a heteroarylene group having 5 to 40 nuclear atoms, preferably an arylene group of C 6 to C 20 and It may be selected from the group consisting of a heteroarylene group having 5 to 20 nuclear atoms. Specific examples of L 1 include an arylene group such as a phenylene group, a biphenylene group, and a terphenylene group; There are heteroarylene groups such as a divalent dibenzofuran group, a divalent dibenzothiophene group, and a divalent fluorene group. According to an example, L 1 may be selected from the group consisting of the following linker groups L1 to L6:
상기 링커기 L1 내지 L6의 구체적인 예로는 하기 L1-1~L1-2, L2-1~L2-3, L3-1, L4-1~L4-4, L5-1~L5-6, 및 L6-1~L6-5 등이 있는데, 이에 한정되지 않는다.Specific examples of the linker groups L1 to L6 include the following L1-1 to L1-2, L2-1 to L2-3, L3-1, L4-1 to L4-4, L5-1 to L5-6, and L6- 1 to L6-5, and the like, but are not limited thereto.
전술한 L1의 종류에 따라 본 발명에 따른 화학식 1의 화합물은 하기 화학식 5 또는 6으로 표시되는 화합물로 구체화될 수 있는데, 이에 한정되지 않는다.Depending on the type of L 1 described above, the compound of Formula 1 according to the present invention may be embodied as a compound represented by the following Formula 5 or 6, but is not limited thereto.
상기 화학식 5 및 6에서,In Formulas 5 and 6,
Z1 내지 Z3, Ar1 및 Ar2는 각각 화학식 1에서 정의된 바와 같고,Z 1 to Z 3 , Ar 1 and Ar 2 are each as defined in Formula 1,
a는 0 내지 4의 정수이고, a is an integer from 0 to 4,
b 및 c는 각각 0 내지 3의 정수이며,b and c are each an integer of 0 to 3,
L2 및 L3는 서로 동일하거나 상이하고, 각각 독립적으로 단일결합이거나, 또는 C6~C20의 아릴렌기 및 핵원자수 5 내지 20의 헤테로아릴렌기로 이루어진 군에서 선택되고,L 2 and L 3 are the same as or different from each other, and each independently a single bond, or is selected from the group consisting of an arylene group of C 6 to C 20 and a heteroarylene group of 5 to 20 nuclear atoms,
Y1은 O, S 및 C(R5)(R6)으로 이루어진 군에서 선택되고, Y 1 is selected from the group consisting of O, S and C(R 5 )(R 6 ),
R2 내지 R6은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,R 2 to R 6 are the same as or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, 3 to 40 nuclear atom heterocycloalkyl group, C 6 to C 60 aryl group, 5 to 60 nuclear atom heteroaryl group, C 1 to C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C the group of boron 60 aryl, C 6 ~ C 60 aryl phosphine group, is selected from the group consisting of C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ C 60 aryl group of an amine of,
상기 L2 및 L3의 아릴렌기와 헤테로아릴렌기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이하다.The arylene group and heteroarylene group of L 2 and L 3 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 Alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyl of C 1 to C 40 Oxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C aryl phosphine oxide 60 group and a C 6 ~ C 60 aryl group is unsubstituted or substituted by one substituent at least one selected from the group consisting of amine groups of, wherein When the above substituents are plural, they are the same as or different from each other.
구체적으로, 본 발명에 따른 화학식 1로 표시되는 화합물은 하기 화학식 7 내지 12 중 어느 하나로 표시되는 화합물로 구체화될 수 있는데, 이에 한정되지 않는다.Specifically, the compound represented by Formula 1 according to the present invention may be embodied as a compound represented by any one of the following Formulas 7 to 12, but is not limited thereto.
상기 화학식 7 내지 12에서,In Formulas 7 to 12,
Z1 내지 Z3, Ar1 및 Ar2는 각각 화학식 1에서 정의한 바와 같고,Z 1 to Z 3 , Ar 1 and Ar 2 are each as defined in Formula 1,
R5 및 R6은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 바람직하게 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C20의 알킬기, C6~C20의 아릴기, 핵원자수 5 내지 20개의 헤테로아릴기, C6~C20의 아릴아민기로 이루어진 군에서 선택될 수 있다. 여기서, 상기 헤테로시클로알킬기, 헤테로아릴기 및 축합 헤테로방향족고리는 각각 N, S, O 및 Se로 이루어진 군에서 선택된 1개 이상의 헤테로 원자를 포함할 수 있다.R 5 and R 6 are the same as or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, 3 to 40 nuclear atom heterocycloalkyl group, C 6 to C 60 aryl group, 5 to 60 nuclear atom heteroaryl group, C 1 to C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C group of 60 arylboronic, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ C 60 is selected from the group consisting of an aryl amine, preferably hydrogen, deuterium, halogen In the group consisting of a group, a cyano group, a nitro group, an amino group, a C 1 to C 20 alkyl group, a C 6 to C 20 aryl group, a heteroaryl group having 5 to 20 nuclear atoms, and a C 6 to C 20 arylamine group Can be chosen. Here, the heterocycloalkyl group, the heteroaryl group, and the condensed heteroaromatic ring may each include at least one hetero atom selected from the group consisting of N, S, O and Se.
또, 상기 화학식 1로 표시되는 화합물에서, Z1 내지 Z3는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 CR1이고, 다만 Z1 내지 Z3 중 적어도 2개는 N이다. 이때, R1은 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 또는 인접한 기(예, Ar1, Ar2)와 결합하여 축합 고리를 형성한다. 여기서, 축합 고리는 C6~C20의 축합 방향족 고리이거나, 또는 5원~20원의 축합 헤테로방향족고리일 수 있고, 또 상기 헤테로시클로알킬기, 헤테로아릴기 및 축합 헤테로방향족고리는 각각 N, S, O 및 Se로 이루어진 군에서 선택된 1개 이상의 헤테로 원자를 포함할 수 있다. In addition, in the compound represented by Formula 1, Z 1 to Z 3 are the same as or different from each other, and each independently N or CR 1 , provided that at least two of Z 1 to Z 3 are N. At this time, R 1 is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 to C 60 aryl group, 5 to 60 nuclear atom heteroaryl group, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~, or selected from the group consisting of an aryl amine of the C 60 in, or in conjunction with an adjacent group (for example, Ar 1, Ar 2) fused ring To form. Here, the condensed ring may be a C 6 ~ C 20 condensed aromatic ring, or a 5 to 20 membered condensed heteroaromatic ring, and the heterocycloalkyl group, heteroaryl group and condensed heteroaromatic ring are each N, S , O and Se may contain at least one hetero atom selected from the group consisting of.
일례에 따르면, Z1 내지 Z3은 모두 N이다. According to an example, Z 1 to Z 3 are all N.
다른 일례에 따르면, Z1 내지 Z3 중 2개는 N이고, 나머지는 CR1이다. 이때, R1은 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C20의 알킬기, C6~C20의 아릴기, 및 핵원자수 5 내지 20개의 헤테로아릴기로 이루어진 군에서 선택될 수 있고, 또는 인접한 기인 Ar1 및/또는 Ar2와 결합하여 C6~C20의 축합 고리를 형성할 수 있다. According to another example, two of Z 1 to Z 3 are N, and the rest are CR 1 . At this time, R 1 is a group consisting of hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 20 alkyl group, C 6 to C 20 aryl group, and heteroaryl group having 5 to 20 nuclear atoms It may be selected from, or may be combined with an adjacent group Ar 1 and/or Ar 2 to form a condensed ring of C 6 ~ C 20 .
또, 상기 화학식 1로 표시되는 화합물에서, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택되고, 구체적으로 각각 독립적으로 C6~C20의 아릴기 및 핵원자수 5 내지 20개의 헤테로아릴기로 이루어진 군에서 선택될 수 있다. 여기서, 상기 헤테로아릴기는 각각 N, S, O 및 Se로 이루어진 군에서 선택된 1개 이상의 헤테로 원자를 포함할 수 있다. In addition, in the compound represented by Formula 1, Ar 1 and Ar 2 are the same as or different from each other, and each independently selected from the group consisting of an aryl group of C 6 to C 60 and a heteroaryl group having 5 to 60 nuclear atoms , Specifically, each independently may be selected from the group consisting of an aryl group of C 6 to C 20 and a heteroaryl group having 5 to 20 nuclear atoms. Here, the heteroaryl group may each include at least one hetero atom selected from the group consisting of N, S, O, and Se.
일례에 따르면, Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기, 비페닐기, 1가의 디벤조퓨란기, 및 1가의 디벤조싸이오펜기로 이루어진 군에서 선택될 수 있다. According to an example, Ar 1 and Ar 2 are the same as or different from each other, and each may be independently selected from the group consisting of a phenyl group, a biphenyl group, a monovalent dibenzofuran group, and a monovalent dibenzothiophene group.
전술한 Z1~Z3 및 Ar1~Ar2의 종류에 따라, 상기 화학식 1의 화합물에서, 
모이어티는 하기 치환기 EWG1 내지 EWG17로 이루어진 군에서 선택된 것일 수 있다:Depending on the type of Z 1 to Z 3 and Ar 1 to Ar 2 described above, in the compound of Formula 1, The moiety may be selected from the group consisting of the following substituents EWG1 to EWG17:
또, 상기 화학식 1로 표시되는 화합물에서, 상기 L1의 아릴렌기와 헤테로아릴렌기, R1의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기와 아릴아민기, 및 Ar1 및 Ar2의 아릴기와 헤테로아릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되고, 바람직하게 중수소, 할로겐, 시아노기, 니트로기, C1~C20의 알킬기, C6~C30의 아릴기, 핵원자수 5 내지 30개의 헤테로아릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환될 수 있다. 이때, 상기 치환기가 복수인 경우, 복수의 치환기는 서로 동일하거나 상이하다. 여기서, 상기 헤테로시클로알킬기 및 헤테로아릴기는 각각 N, S, O 및 Se로 이루어진 군에서 선택된 1개 이상의 헤테로원자를 포함할 수 있다.In addition, in the compound represented by Formula 1, the arylene group of L 1 , a heteroarylene group, an alkyl group of R 1 , an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group , Aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, arylphosphine group, arylphosphine oxide group and arylamine group, and the aryl and heteroaryl groups of Ar 1 and Ar 2 are each independently deuterium , Halogen, cyano group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, 3 to 40 nuclear atoms Heterocycloalkyl group of, C 6 to C 60 aryl group, heteroaryl group of 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 Alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphine group, C 6 ~ C 60 Unsubstituted or substituted with one or more substituents selected from the group consisting of arylphosphine oxide group and C 6 ~ C 60 arylamine group, preferably deuterium, halogen, cyano group, nitro group, C 1 ~ C 20 alkyl group , C 6 ~ C 30 may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 30 nuclear atoms. In this case, when there are a plurality of substituents, the plurality of substituents are the same or different from each other. Here, the heterocycloalkyl group and the heteroaryl group may each include one or more heteroatoms selected from the group consisting of N, S, O, and Se.
상기에서 설명한 본 발명에 따른 화학식 1로 표시되는 화합물은 화합물 (1) 내지 화합물 (121)로 보다 구체화될 수 있는데, 이에 의해 한정되는 것은 아니다.The compound represented by Formula 1 according to the present invention described above may be further specified as compounds (1) to (121), but is not limited thereto.
본 발명에서 "알킬"은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등이 있는데, 이에 한정되지는 않는다.In the present invention, "alkyl" refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.
본 발명에서 "알케닐(alkenyl)"은 탄소-탄소 이중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등이 있는데, 이에 한정되지는 않는다.In the present invention, "alkenyl" refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon double bonds. Examples thereof include vinyl (vinyl), allyl (allyl), isopropenyl (isopropenyl), 2-butenyl (2-butenyl), and the like, but is not limited thereto.
본 발명에서 "알키닐(alkynyl)"은 탄소-탄소 삼중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등이 있는데, 이에 한정되지는 않는다.In the present invention, "alkynyl" refers to a monovalent substituent derived from a straight or branched unsaturated hydrocarbon having 2 to 40 carbon atoms having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl and 2-propynyl.
본 발명에서 "시클로알킬"은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine) 등이 있는데, 이에 한정되지는 않는다.In the present invention, "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.
본 발명에서 "헤테로시클로알킬"은 핵원자수 3 내지 40의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등이 있는데, 이에 한정되지는 않는다.In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons, is N, O, S Or a hetero atom such as Se. Examples of such heterocycloalkyl include morpholine and piperazine, but are not limited thereto.
본 발명에서 "아릴"은 단독 고리 또는 2이상의 고리가 조합된 탄소수 6 내지 60의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등이 있는데, 이에 한정되지는 않는다.In the present invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In addition, a form in which two or more rings are simply attached to each other or condensed may be included. Examples of such aryl include phenyl, naphthyl, phenanthryl, and anthryl, but are not limited thereto.
본 발명에서 "헤테로아릴"은 핵원자수 5 내지 60의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있고, 나아가 아릴기와의 축합된 형태도 포함될 수 있다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리, 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등이 있는데, 이에 한정되지는 않는다.In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, one or more carbons, preferably 1 to 3 carbons in the ring are substituted with heteroatoms such as N, O, S or Se. In addition, a form in which two or more rings are simply attached to each other or condensed may be included, and further, a form condensed with an aryl group may be included. Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, phenoxathienyl, indolizinyl, indolyl ( indolyl), purinyl, quinolyl, benzothiazole, polycyclic rings such as carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
본 발명에서 "알킬옥시"는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 탄소수 1 내지 40의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등이 있는데, 이에 한정되지는 않는다.In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R'refers to alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure It may include. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, and the like.
본 발명에서 "아릴옥시"는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 5 내지 40의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있는데, 이에 한정되지는 않는다.In the present invention, "aryloxy" is a monovalent substituent represented by RO-, and R means an aryl having 5 to 40 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, and diphenyloxy.
본 발명에서 "알킬실릴"은 탄소수 1 내지 40의 알킬로 치환된 실릴을 의미하며, 모노-뿐만 아니라 디-, 트리-알킬실릴을 포함한다. 또, "아릴실릴"은 탄소수 5 내지 60의 아릴로 치환된 실릴을 의미하고, 모노-뿐만 아니라 디-, 트리-아릴실릴 등의 폴리아릴실릴을 포함한다.In the present invention, "alkylsilyl" refers to silyl substituted with alkyl having 1 to 40 carbon atoms, and includes mono- as well as di- and tri-alkylsilyl. In addition, "arylsilyl" refers to silyl substituted with aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as di- and tri-arylsilyl as well as mono-.
본 발명에서 "알킬보론기"는 탄소수 1 내지 40의 알킬로 치환된 보론기를 의미하며, "아릴보론기"는 탄소수 6 내지 60의 아릴로 치환된 보론기를 의미한다.In the present invention, "alkyl boron group" refers to a boron group substituted with an alkyl having 1 to 40 carbon atoms, and "aryl boron group" refers to a boron group substituted with an aryl having 6 to 60 carbon atoms.
본 발명에서 "알킬포스피닐기"는 탄소수 1 내지 40의 알킬로 치환된 포스핀기를 의미하고, 모노- 뿐만 아니라 디-알킬포스피닐기를 포함한다. 또, 본 발명에서 "아릴포스피닐기"는 탄소수 6 내지 60의 모노아릴 또는 디아릴로 치환된 포스핀기를 의미하고, 모노- 뿐만 아니라 디-아릴포스피닐기를 포함한다. In the present invention, the "alkylphosfinyl group" refers to a phosphine group substituted with an alkyl having 1 to 40 carbon atoms, and includes not only mono- but also di-alkylphosfinyl groups. In addition, in the present invention, "arylphosphinyl group" refers to a phosphine group substituted with a monoaryl or diaryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosfinyl groups.
본 발명에서 "아릴아민"은 탄소수 6 내지 40의 아릴로 치환된 아민을 의미하며, 모노-뿐만 아니라 디-아릴아민를 포함한다.In the present invention, "arylamine" refers to an amine substituted with an aryl having 6 to 40 carbon atoms, and includes mono- as well as di-arylamine.
<유기 전계 발광 소자><Organic EL device>
한편, 본 발명의 다른 측면은 전술한 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자(이하, '유기 EL 소자')에 관한 것이다.Meanwhile, another aspect of the present invention relates to an organic electroluminescent device (hereinafter, referred to as “organic EL device”) including the compound represented by Formula 1 above.
구체적으로, 본 발명에 따른 유기 전계 발광 소자는 양극(anode), 음극(cathode) 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화합물은 단독으로 사용되거나, 또는 2 이상이 혼합되어 사용될 수 있다.Specifically, the organic electroluminescent device according to the present invention includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers is It includes a compound represented by Formula 1. In this case, the compound may be used alone, or two or more may be used in combination.
상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광층, 전자 수송 보조층, 전자 수송층, 및 전자 주입층 중 어느 하나 이상을 포함할 수 있고, 이 중에서 적어도 하나의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함한다. 구체적으로, 상기 화학식 1의 화합물을 포함하는 유기물층은 발광층, 전자수송층 및 전자수송 보조층으로 이루어진 군에서 선택된 것일 수 있다.The one or more organic material layers may include any one or more of a hole injection layer, a hole transport layer, an emission layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, of which at least one organic material layer is represented by Formula 1 above. Contains compounds. Specifically, the organic material layer including the compound of Formula 1 may be selected from the group consisting of a light emitting layer, an electron transport layer, and an electron transport auxiliary layer.
일례에 따르면, 상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송층, 및 전자주입층을 포함하고, 상기 전자수송층은 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화학식 1로 표시되는 화합물은 전자수송층 물질로 유기 전계 발광 소자에 포함된다. 이러한 유기 전계 발광 소자에서, 전자는 상기 화학식 1의 화합물 때문에, 음극 또는 전자주입층에서 전자수송층으로 용이하게 주입되고, 또한 전자수송층에서 발광층으로 빠르게 이동할 수 있고, 따라서 발광층에서의 정공과 전자의 결합력이 높다. 그러므로, 본 발명의 유기 전계 발광 소자는 발광효율, 전력효율, 휘도 등이 우수하다. 게다가, 상기 화학식 1의 화합물은 열적 안정성, 전기화학적 안정성이 우수하여, 유기 전계 발광 소자의 성능을 향상시킬 수 있다.According to an example, the at least one organic material layer includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and the electron transport layer includes the compound represented by Formula 1. In this case, the compound represented by Formula 1 is an electron transport layer material and is included in the organic electroluminescent device. In such an organic electroluminescent device, because of the compound of Formula 1, electrons are easily injected from the cathode or electron injection layer to the electron transport layer, and can quickly move from the electron transport layer to the light emitting layer, and thus, the binding force of holes and electrons in the light emitting layer Is high. Therefore, the organic electroluminescent device of the present invention is excellent in luminous efficiency, power efficiency, and brightness. In addition, the compound of Formula 1 has excellent thermal stability and electrochemical stability, and can improve the performance of an organic electroluminescent device.
다른 일례에 따르면, 상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송 보조층, 전자수송층, 및 전자주입층을 포함하고, 상기 전자수송 보조층은 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화학식 1로 표시되는 화합물은 전자수송 보조층 물질로 유기 전계 발광 소자에 포함된다. 이때, 상기 화학식 1의 화합물이 높은 삼중항 에너지를 갖는다. 이 때문에, 상기 화학식 1의 화합물을 전자수송 보조층 물질로 포함할 경우, TTF(triplet-triplet fusion) 효과로 인해 유기 전계 발광 소자의 효율이 상승될 수 있다. 또한, 상기 화학식 1의 화합물은 발광층에서 생성된 엑시톤이 발광층에 인접하는 전자수송층으로 확산되는 것을 방지할 수 있다. 따라서, 발광층 내에서 발광에 기여하는 엑시톤의 수가 증가되어 소자의 발광 효율이 개선될 수 있고, 소자의 내구성 및 안정성이 향상되어 소자의 수명이 효율적으로 증가될 수 있다. According to another example, the one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, and the electron transport auxiliary layer comprises the compound represented by Formula 1 Include. In this case, the compound represented by Formula 1 is included in the organic electroluminescent device as an electron transport auxiliary layer material. At this time, the compound of Formula 1 has a high triplet energy. For this reason, when the compound of Formula 1 is included as an electron transport auxiliary layer material, the efficiency of the organic electroluminescent device may be increased due to the TTF (triplet-triplet fusion) effect. In addition, the compound of Formula 1 can prevent the excitons generated in the emission layer from being diffused into the electron transport layer adjacent to the emission layer. Accordingly, the number of excitons contributing to light emission in the light emitting layer is increased, so that the luminous efficiency of the device can be improved, the durability and stability of the device are improved, so that the life of the device can be effectively increased.
또 다른 일례에 따르면, 상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송층, 및 전자주입층을 포함하고, 상기 발광층은 호스트 재료와 도펀트 재료를 포함하는데, 이때 호스트 재료로서 상기 화학식 1의 화합물을 포함할 수 있다. 또한, 본 발명의 발광층은 상기 화학식 1의 화합물 이외의 당 분야의 공지된 화합물을 호스트로서 포함할 수 있다. According to another example, the one or more organic material layers include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer, and the emission layer includes a host material and a dopant material, wherein the chemical formula It may contain the compound of 1. In addition, the light emitting layer of the present invention may include a compound known in the art other than the compound of Formula 1 as a host.
구체적으로, 상기 호스트는 p형 호스트 및 n형 호스트를 포함할 수 있다. 이때, 상기 n형 호스트는 상기 화학식 1의 화합물을 포함한다. 또, 상기 p형 호스트는 p형의 성질을 갖는 호스트 물질로, 구체적으로 정공 수송성이 전자 수송성보다 우수한 물질로, 정공을 주입받거나 수송하는 특성이 큰 물질, 즉 정공의 전도도가 큰 물질이다. 본 발명에서 사용 가능한 p형 호스트로는 당 업계에 일반적으로 알려진 정공 전도도가 큰 물질이라면 제한 없이 사용할 수 있고, 예컨대 카바졸계 유도체 등이 있는데, 이에 한정되지 않는다. Specifically, the host may include a p-type host and an n-type host. In this case, the n-type host includes the compound of Formula 1. In addition, the p-type host is a host material having a p-type property, specifically, a material having better hole transport properties than an electron transport property, and a material having a high hole injection or transport property, that is, a material having a high hole conductivity. The p-type host usable in the present invention may be used without limitation as long as it is a material having a high hole conductivity generally known in the art. For example, a carbazole derivative or the like may be used, but is not limited thereto.
상기 p형 호스트 및 n형 호스트의 사용 비율은 1:99 ~ 99:1의 중량 비율, 구체적으로 30:70 ~ 70:30 중량비율일 수 있다. The use ratio of the p-type host and the n-type host may be a weight ratio of 1:99 to 99:1, specifically, a weight ratio of 30:70 to 70:30.
본 발명에서, 호스트의 함량은 발광층의 총량을 기준으로 약 70 내지 99.9 중량%일 수 있고, 도펀트의 함량은 발광층의 총량을 기준으로 약 0.1 내지 30 중량%일 수 있다.In the present invention, the content of the host may be about 70 to 99.9% by weight based on the total amount of the light emitting layer, and the content of the dopant may be about 0.1 to 30% by weight based on the total amount of the light emitting layer.
상기 화학식 1로 표시되는 화합물은 발광층 재료, 바람직하게 녹색, 청색 및 적색의 인광 호스트 물질, 더 바람직하게 녹색의 인광 호스트 물질로 유기 전계 발광 소자에 포함된다. 이 경우, 발광층에서의 정공과 전자의 결합력이 높아지기 때문에, 유기 전계 발광 소자의 효율(발광효율 및 전력효율), 수명, 휘도, 구동 전압, 열적 안정성 등이 향상될 수 있다. 구체적으로 상기 화학식 1로 표시되는 화합물은 녹색 및/또는 적색의 인광 호스트, 형광 호스트, 또는 도펀트 재료로서 유기 전계 발광 소자에 포함되는 것이 바람직하다. 특히, 본 발명의 화학식 1로 표시되는 화합물은 고효율을 가진 발광층의 그린 인광 호스트 재료인 것이 바람직하다. The compound represented by Formula 1 is a light emitting layer material, preferably a green, blue and red phosphorescent host material, more preferably a green phosphorescent host material, and is included in the organic electroluminescent device. In this case, since the bonding force between holes and electrons in the emission layer is increased, the efficiency (luminescence efficiency and power efficiency), lifespan, luminance, driving voltage, thermal stability, and the like of the organic electroluminescent device can be improved. Specifically, the compound represented by Formula 1 is preferably included in the organic electroluminescent device as a green and/or red phosphorescent host, fluorescent host, or dopant material. In particular, it is preferable that the compound represented by Chemical Formula 1 of the present invention is a green phosphorescent host material for a light emitting layer having high efficiency.
이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 예컨대 기판 위에, 양극(100), 1층 이상의 유기물층(300) 및 음극(200)이 순차적으로 적층될 수 있다(도 1 및 도 2참조). 뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.The structure of the organic electroluminescent device of the present invention is not particularly limited, but, for example, an anode 100, one or more organic material layers 300, and a cathode 200 may be sequentially stacked on a substrate (FIGS. 1 and 2 Reference). In addition, it may have a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer.
일례에 따르면, 상기 유기 전계 발광 소자는 도 1에 도시된 바와 같이, 기판 위에, 양극(100), 정공주입층(310), 정공수송층(320), 발광층(330), 전자수송층(340) 및 음극(200)이 순차적으로 적층된 구조를 가질 수 있다. 선택적으로, 도 2에 도시된 바와 같이, 상기 전자수송층(340)과 음극(200) 사이에 전자주입층(350)이 위치할 수 있다. 또한, 상기 발광층(330)과 전자수송층(340) 사이에 전자수송 보조층(미도시됨)이 위치할 수 있다. 본 발명의 유기 전계 발광 소자는 상기 유기물층(300) 중 적어도 하나[예컨대, 발광층(330), 전자수송층(340), 또는 전자수송 보조층(미도시됨)]가 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는, 당 기술 분야에 알려져 있는 재료 및 방법으로 유기물층 및 전극을 형성하여 제조할 수 있다.According to an example, as shown in FIG. 1, the organic electroluminescent device includes an anode 100, a hole injection layer 310, a hole transport layer 320, a light emitting layer 330, an electron transport layer 340, and The cathode 200 may have a sequentially stacked structure. Optionally, as shown in FIG. 2, an electron injection layer 350 may be positioned between the electron transport layer 340 and the cathode 200. In addition, an electron transport auxiliary layer (not shown) may be positioned between the emission layer 330 and the electron transport layer 340. In the organic electroluminescent device of the present invention, at least one of the organic material layers 300 (e.g., the emission layer 330, the electron transport layer 340, or the electron transport auxiliary layer (not shown)) contains a compound represented by Formula 1 above. Except for including, it can be manufactured by forming an organic material layer and an electrode using materials and methods known in the art.
상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이에 한정되지는 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer method.
본 발명에서 사용 가능한 기판은 특별히 한정되지 않으며, 비제한적인 예로는 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등이 있다.The substrate usable in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.
또, 양극 물질의 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등이 있는데, 이에 한정되지는 않는다.Further, examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; Conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
또, 음극 물질의 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있는데, 이에 한정되지는 않는다.Further, examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof; And a multilayered material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
이하 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail through examples. However, the following examples are only illustrative of the present invention, and the present invention is not limited by the following examples.
[준비예 1] Core-1의 합성[Preparation Example 1] Synthesis of Core-1
<단계 1> 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9H-tribenzo[a,c,e][7]annulen-9-ol 의 합성<Step 1> Synthesis of 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9H-tribenzo[a,c,e][7]annulen-9-ol
2-Bromo-4'-chloro-1,1'-biphenyl 40 g (0.15 mol)에 THF 400 mL를 가하였다. 이후, 반응액의 온도를 - 78 ℃로 낮추고, 이 반응액에 1.6M의 n-BuLi solution 103 mL (0.16 mol)를 천천히 적가한 다음, - 78 ℃의 온도에서 1시간 동안 교반하였다. 이후, 9H-tribenzo[a,c,e][7]annulen-9-one 42.2 g (0.16 mol)을 THF 400 mL에 용해시킨 다음, 이 용액을 상기 반응액에 천천히 첨가한 후, - 78 ℃의 온도에서 1시간 동안 교반하고, 상온(20ㅁ5℃)에서 24시간 동안 추가로 교반하였다. 그 다음, 상기 반응액에 정제수 500 mL를 투입하여 반응을 종결시킨 후, ethyl acetate(E.A) 2.0 L로 추출하고, 증류수로 세척하였다. 이후, 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류한 후 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 47.9 g (수율 72 %)을 얻었다.400 mL of THF was added to 40 g (0.15 mol) of 2-Bromo-4'-chloro-1,1'-biphenyl. Thereafter, the temperature of the reaction solution was lowered to -78°C, 103 mL (0.16 mol) of 1.6M n-BuLi solution was slowly added dropwise to the reaction solution, followed by stirring at -78°C for 1 hour. Thereafter, 42.2 g (0.16 mol) of 9H-tribenzo[a,c,e][7]annulen-9-one was dissolved in 400 mL of THF, and this solution was slowly added to the reaction solution, and then -78 ℃ The mixture was stirred at a temperature of 1 hour and further stirred at room temperature (20ㅁ5°C) for 24 hours. Then, 500 mL of purified water was added to the reaction solution to terminate the reaction, followed by extraction with 2.0 L of ethyl acetate (EA) and washing with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 47.9 g (yield 72%) of the title compound.
[LCMS] : 444[LCMS]: 444
<단계 2> 2-chlorospiro[fluorene-9,9'-tribenzo[a,c,e][7]annulene] 의 합성<Step 2> Synthesis of 2-chlorospiro[fluorene-9,9'-tribenzo[a,c,e][7]annulene]
상기 <단계 1>에서 얻은 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9H-tribenzo[a,c,e][7]annulen-9-ol 47.0 g (0.11 mol)에 concentrated HCl(conc.HCl) 71 mL와 acetic acid(AcOH) 705 mL를 첨가한 후, 상기 반응액을 100℃에서 2시간 동안 가열환류한 후, 상온으로 온도를 냉각하였다. 이후, 냉각된 반응액에 정제수 500 mL를 투입하여 반응을 종결시킨 후, 생성된 고체를 감압여과하고 훈풍 건조하여 목적 화합물 43.3 g (수율 96 %)을 얻었다.9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9H-tribenzo[a,c,e][7]annulen-9-ol 47.0 g obtained in the <Step 1> ( 0.11 mol) to 71 mL of concentrated HCl (conc.HCl) and 705 mL of acetic acid (AcOH) were added, and the reaction solution was heated to reflux at 100° C. for 2 hours, and then the temperature was cooled to room temperature. Thereafter, 500 mL of purified water was added to the cooled reaction solution to terminate the reaction, and the resulting solid was filtered under reduced pressure and dried with hot air to obtain 43.3 g (yield 96%) of the target compound.
[LCMS] : 426[LCMS]: 426
<단계 3> 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-tribenzo[a,c,e][7]annulen]-2-yl)-1,3,2-dioxaborolane 의 합성<Step 3> 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-tribenzo[a,c,e][7]annulen]-2-yl)-1,3,2 -dioxaborolane synthesis
상기 <단계 2>에서 합성된 2-chlorospiro[fluorene-9,9'-tribenzo[a,c,e][7]annulene] 43.0 g (101 mmol) 및 4,4,4',4',5,5,5',5'-옥타메틸-2,2'-비(1,3,2-디옥사보로란) 30.7 g (121 mmol)에 디옥산 500 mL를 첨가한 다음, Pd(dppf)Cl2 4.2 g (5.1 mmol), XPhos 4.8 g (10.1 mmol)와 KOAc 29.7 g (303 mmol)을 첨가한 후, 130 ℃에서 3시간 동안 가열 환류하였다. 그 다음, 상기 반응액의 온도를 상온으로 냉각한 후, 냉각된 반응액에 염화암모늄 수용액 500 mL를 투입하여 반응을 종결시키고, E.A 1.0 L로 추출하고, 증류수로 세척하였다. 이후, 얻어진 유기층을 무수 MgSO4로 건조하고, 감압 증류한 후 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 38.2 g (수율 73 %)을 얻었다.2-chlorospiro[fluorene-9,9'-tribenzo[a,c,e][7]annulene] 43.0 g (101 mmol) and 4,4,4',4',5 synthesized in <Step 2> 500 mL of dioxane was added to 30.7 g (121 mmol) of 5,5',5'-octamethyl-2,2'-ratio (1,3,2-dioxaborolane), and then Pd(dppf )Cl 2 4.2 g (5.1 mmol), XPhos 4.8 g (10.1 mmol) and KOAc 29.7 g (303 mmol) were added, followed by heating to reflux at 130° C. for 3 hours. Then, after cooling the temperature of the reaction solution to room temperature, 500 mL of an aqueous ammonium chloride solution was added to the cooled reaction solution to terminate the reaction, extracted with 1.0 L of EA, and washed with distilled water. Thereafter, the obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 38.2 g (yield 73%) of the title compound.
[LCMS] : 518[LCMS]: 518
[준비예 2] Core-2의 합성[Preparation Example 2] Synthesis of Core-2
<단계 1> 9-(3'-chloro-[1,1'-biphenyl]-2-yl)-9H-tribenzo[a,c,e][7]annulen-9-ol 의 합성<Step 1> Synthesis of 9-(3'-chloro-[1,1'-biphenyl]-2-yl)-9H-tribenzo[a,c,e][7]annulen-9-ol
상기 [준비예 1]의 <단계 1>에서 사용된 2-Bromo-4'-chloro-1,1'-biphenyl 대신 2-Bromo-3'-chloro-1,1'-biphenyl을 사용하는 것을 제외하고는, 상기 [준비예 1]의 <단계 1>과 동일한 과정을 수행하여 목적 화합물 66.5 g (80 %)을 얻었다. 이때 합성된 목적 화합물은 준비예 1의 <단계 1>에서 얻은 화합물의 구조 이성질체에 해당되었다.Except for the use of 2-Bromo-3'-chloro-1,1'-biphenyl instead of 2-Bromo-4'-chloro-1,1'-biphenyl used in <Step 1> of [Preparation Example 1] Then, 66.5 g (80%) of the target compound was obtained by performing the same procedure as in <Step 1> of [Preparation Example 1]. At this time, the synthesized target compound corresponds to the structural isomer of the compound obtained in <Step 1> of Preparation Example 1.
[LCMS] : 444[LCMS]: 444
<단계 2> 3-chlorospiro[fluorene-9,9'-tribenzo[a,c,e][7]annulene] 의 합성<Step 2> Synthesis of 3-chlorospiro[fluorene-9,9'-tribenzo[a,c,e][7]annulene]
상기 [준비예 1]의 <단계 2>에서 사용된 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9H-tribenzo[a,c,e][7]annulen-9-ol 대신 상기 <단계 1>에서 얻은 9-(3'-chloro-[1,1'-biphenyl]-2-yl)-9H-tribenzo[a,c,e][7]annulen-9-ol를 사용하는 것을 제외하고는, 상기 [준비예 1]의 <단계 2>와 동일한 과정을 수행하여 목적 화합물 60.2 g (95 %)을 얻었다. 이때 합성된 목적 화합물은 준비예 1의 <단계 2>에서 얻은 화합물의 구조 이성질체에 해당되었다.9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9H-tribenzo[a,c,e][7]annulen used in <Step 2> of [Preparation Example 1] 9-(3'-chloro-[1,1'-biphenyl]-2-yl)-9H-tribenzo[a,c,e][7]annulen-9 obtained in <Step 1> instead of -9-ol Except for using -ol, 60.2 g (95%) of the title compound was obtained by performing the same procedure as in <Step 2> of [Preparation Example 1]. At this time, the synthesized target compound corresponds to the structural isomer of the compound obtained in <Step 2> of Preparation Example 1.
[LCMS] : 426[LCMS]: 426
<단계 3> 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-tribenzo[a,c,e][7]annulen]-3-yl)-1,3,2-dioxaborolane 의 합성<Step 3> 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-tribenzo[a,c,e][7]annulen]-3-yl)-1,3,2 -dioxaborolane synthesis
상기 [준비예 1]의 <단계 3>에서 사용된 2-chlorospiro[fluorene-9,9'-tribenzo[a,c,e][7]annulene] 대신 상기 <단계 2>에서 얻은 3-chlorospiro[fluorene-9,9'-tribenzo[a,c,e][7]annulene]를 사용하는 것을 제외하고는, 상기 [준비예 1]의 <단계 3>과 동일한 과정을 수행하여 목적 화합물 45.2 g (62 %)을 얻었다. 이때 합성된 목적 화합물은 준비예 1의 <단계 3>에서 얻은 화합물의 구조 이성질체에 해당되었다.Instead of 2-chlorospiro[fluorene-9,9'-tribenzo[a,c,e][7]annulene] used in <Step 3> of [Preparation Example 1], 3-chlorospiro[ obtained in <Step 2>] Except for the use of fluorene-9,9'-tribenzo[a,c,e][7]annulene], the same procedure as in <Step 3> of [Preparation Example 1] was performed, and the target compound 45.2 g ( 62%). At this time, the synthesized target compound corresponds to the structural isomer of the compound obtained in <Step 3> of Preparation Example 1.
[LCMS] : 518[LCMS]: 518
[준비예 3] Core-3의 합성[Preparation Example 3] Synthesis of Core-3
<단계 1> 9-(2'-bromo-[1,1'-biphenyl]-2-yl)-9H-tribenzo[a,c,e][7]annulen-9-ol 의 합성<Step 1> Synthesis of 9-(2'-bromo-[1,1'-biphenyl]-2-yl)-9H-tribenzo[a,c,e][7]annulen-9-ol
상기 [준비예 1]의 <단계 1>에서 사용된 2-Bromo-4'-chloro-1,1'-biphenyl 대신 2-Bromo-2'-Bromo-1,1'-biphenyl을 사용하는 것을 제외하고는, 상기 [준비예 1]의 <단계 1>과 동일한 과정을 수행하여 목적 화합물 31.1 g (66 %)을 얻었다. 이때 합성된 목적 화합물은 준비예 1의 <단계 1>에서 얻은 화합물의 구조 이성질체에 해당되었다.Except for the use of 2-Bromo-2'-Bromo-1,1'-biphenyl instead of 2-Bromo-4'-chloro-1,1'-biphenyl used in <Step 1> of [Preparation Example 1] Then, 31.1 g (66%) of the target compound was obtained by performing the same procedure as in <Step 1> of [Preparation Example 1]. At this time, the synthesized target compound corresponds to the structural isomer of the compound obtained in <Step 1> of Preparation Example 1.
[LCMS] : 489[LCMS]: 489
<단계 2> 4-bromospiro[fluorene-9,9'-tribenzo[a,c,e][7]annulene] 의 합성<Step 2> Synthesis of 4-bromospiro[fluorene-9,9'-tribenzo[a,c,e][7]annulene]
상기 [준비예 1]의 <단계 2>에서 사용된 9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9H-tribenzo[a,c,e][7]annulen-9-ol 대신 상기 <단계 1>에서 얻은 9-(2'-bromo-[1,1'-biphenyl]-2-yl)-9H-tribenzo[a,c,e][7]annulen-9-ol를 사용하는 것을 제외하고는, 상기 [준비예 1]의 <단계 2>와 동일한 과정을 수행하여 목적 화합물 29.0 g (97 %)을 얻었다. 이때 합성된 목적 화합물은 준비예 1의 <단계 2>에서 얻은 화합물의 구조 이성질체에 해당되었다.9-(4'-chloro-[1,1'-biphenyl]-2-yl)-9H-tribenzo[a,c,e][7]annulen used in <Step 2> of [Preparation Example 1] 9-(2'-bromo-[1,1'-biphenyl]-2-yl)-9H-tribenzo[a,c,e][7]annulen-9 obtained in <Step 1> instead of -9-ol Except for using -ol, 29.0 g (97%) of the target compound was obtained by performing the same procedure as in <Step 2> of [Preparation Example 1]. At this time, the synthesized target compound corresponds to the structural isomer of the compound obtained in <Step 2> of Preparation Example 1.
[LCMS] : 471[LCMS]: 471
<단계 3> 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-tribenzo[a,c,e][7]annulen]-4-yl)-1,3,2-dioxaborolane 의 합성<Step 3> 4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-tribenzo[a,c,e][7]annulen]-4-yl)-1,3,2 -dioxaborolane synthesis
상기 [준비예 1]의 <단계 3>에서 사용된 2-chlorospiro[fluorene-9,9'-tribenzo[a,c,e][7]annulene] 대신 상기 <단계 2>에서 얻은 4-bromospiro[fluorene-9,9'-tribenzo[a,c,e][7]annulene]를 사용하는 것을 제외하고는, 상기 [준비예 1]의 <단계 3>과 동일한 과정을 수행하여 목적 화합물 22.4 g (70 %)을 얻었다. 이때 합성된 목적 화합물은 준비예 1의 <단계 3>에서 얻은 화합물의 구조 이성질체에 해당되었다.Instead of 2-chlorospiro[fluorene-9,9'-tribenzo[a,c,e][7]annulene] used in <Step 3> of [Preparation Example 1], 4-bromospiro[ obtained in Step 2> Except for the use of fluorene-9,9'-tribenzo[a,c,e][7]annulene], the same procedure as in <Step 3> of [Preparation Example 1] was performed, and the target compound 22.4 g ( 70%). At this time, the synthesized target compound corresponds to the structural isomer of the compound obtained in <Step 3> of Preparation Example 1.
[LCMS] : 518[LCMS]: 518
[합성예 1] 화합물 2의 합성[Synthesis Example 1] Synthesis of Compound 2
준비예 1에서 합성된 화합물 Core-1 10 g (19.3 mmol) 및 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine 9.0 g (23.2 mmol)에 디옥산 100 mL, 및 H2O 25 mL를 첨가한 후, 여기에 Pd(PPh3)4 1.2 g (1.0 mmol) 및 K2CO3 8.0 g (57.9 mmol)을 첨가한 다음, 120℃에서 4 시간 동안 가열 환류하였다. 이후, 상기 반응액의 온도를 상온으로 냉각하고, 냉각된 반응액에 정제수 300 mL로 반응을 종결한 후, 상기 혼합액을 E.A 1.0 L로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압 증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 8.9 g (수율 66 %)을 얻었다.Compound Core-1 synthesized in Preparation Example 1 10 g (19.3 mmol) and 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine 9.0 g (23.2 mmol) dioxane 100 mL, And after adding 25 mL of H 2 O, Pd(PPh 3 ) 4 1.2 g (1.0 mmol) and K 2 CO 3 8.0 g (57.9 mmol) were added thereto, followed by heating to reflux at 120° C. for 4 hours. . Thereafter, the temperature of the reaction solution was cooled to room temperature, and the reaction was terminated with 300 mL of purified water in the cooled reaction solution, and the mixture was extracted with 1.0 L of EA and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 8.9 g (yield 66%) of the title compound.
[LCMS] : 699[LCMS]: 699
[합성예 2] 화합물 3의 합성[Synthesis Example 2] Synthesis of Compound 3
준비예 1에서 합성된 화합물 Core-1 12.0 g (23.2 mmol) 및 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 10.7 g (25.6 mmol)에 디옥산 200 mL, 및 H2O 50 mL를 첨가한 다음, 여기에 Pd(OAc)2 0.27 g (1.2 mmol), XPhos 1.1 g (2.4 mmol), 및 Cs2CO3 15.1 g (46.4 mmol)을 첨가한 후, 120℃에서 3시간 동안 가열 환류하였다. 이후, 상기 반응액의 온도를 상온으로 냉각하고, 냉각된 반응액에 정제수 500 mL로 반응을 종결하였다. 이어서, 상기 혼합액을 E.A 1 L로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 13.3 g (수율 74 %)을 얻었다.Compound Core-1 synthesized in Preparation Example 1 12.0 g (23.2 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3, To 10.7 g (25.6 mmol) of 5-triazine, 200 mL of dioxane, and 50 mL of H 2 O were added, followed by Pd(OAc) 2 0.27 g (1.2 mmol), XPhos 1.1 g (2.4 mmol), and Cs 2 CO 3 15.1 g (46.4 mmol) was added and then heated to reflux at 120° C. for 3 hours. Thereafter, the temperature of the reaction solution was cooled to room temperature, and the reaction was terminated with 500 mL of purified water in the cooled reaction solution. Subsequently, the mixture was extracted with 1 L of EA and washed with distilled water. The obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and purified by silica gel column chromatography to obtain 13.3 g (yield 74%) of the title compound.
[LCMS] : 775[LCMS]: 775
[합성예 3] 화합물 5의 합성[Synthesis Example 3] Synthesis of Compound 5
합성예 2에서 사용된 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 4-([1,1'-biphenyl]-4-yl)-6-(3-chlorophenyl)-2-phenylpyrimidine을 사용하는 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 5.8 g (수율 72 %)을 얻었다.Instead of 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine used in Synthesis Example 2, 4-([1,1 Except for using'-biphenyl]-4-yl)-6-(3-chlorophenyl)-2-phenylpyrimidine, 5.8 g (yield 72%) of the target compound was prepared in the same manner as in [Synthesis Example 2]. Got it.
[LCMS] : 774[LCMS]: 774
[합성예 4] 화합물 10의 합성[Synthesis Example 4] Synthesis of Compound 10
합성예 1에서 사용된 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 4-(4-bromophenyl)-2,6-diphenylpyrimidine을 사용한 것을 제외하고는, [합성예 1]과 동일한 과정을 수행하여 목적 화합물 9.4 g (수율 61 %)을 얻었다.Except that 4-(4-bromophenyl)-2,6-diphenylpyrimidine was used instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1, [Synthesis The same procedure as in Example 1] was carried out to obtain 9.4 g (61% yield) of the title compound.
[LCMS] : 698[LCMS]: 698
[합성예 5] 화합물 13의 합성[Synthesis Example 5] Synthesis of Compound 13
합성예 2에서 사용된 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 8.6 g (수율 70 %)을 얻었다.2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine used in Synthesis Example 2 instead of 2-(3'-chloro -[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine, except for using the target compound 8.6 g by performing the same procedure as in [Synthesis Example 2] (Yield 70%) was obtained.
[LCMS] : 775[LCMS]: 775
[합성예 6] 화합물 15의 합성[Synthesis Example 6] Synthesis of Compound 15
합성예 2에서 사용된 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 5.5 g (수율 63 %)을 얻었다.2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine used in Synthesis Example 2 instead of 2-(3'-chloro -[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine, except for using the target compound 5.5 g by performing the same procedure as in [Synthesis Example 2] (Yield 63%) was obtained.
[LCMS] : 775[LCMS]: 775
[합성예 7] 화합물 19의 합성[Synthesis Example 7] Synthesis of Compound 19
합성예 2에서 사용된 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 4-([1,1'-biphenyl]-4-yl)-6-(3'-chloro-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine 을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 6.4 g (수율 72 %)을 얻었다.Instead of 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine used in Synthesis Example 2, 4-([1,1 The same procedure as in [Synthesis Example 2], except that'-biphenyl]-4-yl)-6-(3'-chloro-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine was used. To obtain the title compound 6.4 g (72% yield).
[LCMS] : 851[LCMS]: 851
[합성예 8] 화합물 23의 합성[Synthesis Example 8] Synthesis of Compound 23
합성예 2에서 사용된 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 2-(4'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenylpyrimidine을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 10.5 g (수율 60 %)을 얻었다.2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine used in Synthesis Example 2 instead of 2-(4'-chloro Except for using -[1,1'-biphenyl]-3-yl)-4,6-diphenylpyrimidine, 10.5 g (yield 60%) of the target compound was obtained by performing the same procedure as in [Synthesis Example 2].
[LCMS] : 774[LCMS]: 774
[합성예 9] 화합물 28의 합성[Synthesis Example 9] Synthesis of Compound 28
합성예 2에서 사용된 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-phenylquinazoline을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 9.2 g (수율 76 %)을 얻었다.2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine used in Synthesis Example 2 instead of 2-(3'-chloro Except for using -[1,1'-biphenyl]-3-yl)-4-phenylquinazoline, 9.2 g (yield 76%) of the target compound was obtained by performing the same procedure as in [Synthesis Example 2].
[LCMS] : 748[LCMS]: 748
[합성예 10] 화합물 29의 합성[Synthesis Example 10] Synthesis of Compound 29
합성예 2에서 사용된 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 2-(3''-chloro-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine 을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 3.4 g (수율 80 %)을 얻었다.Instead of 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine used in Synthesis Example 2, 2-(3''- Same as [Synthesis Example 2], except that chloro-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used The procedure was carried out to obtain 3.4 g (yield 80%) of the target compound.
[LCMS] : 852[LCMS]: 852
[합성예 11] 화합물 34의 합성[Synthesis Example 11] Synthesis of Compound 34
합성예 2에서 사용된 화합물 Core-1 대신 준비예 2에서 얻은 화합물 Core-2를 사용하고, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 5.9 g (수율 71 %)을 얻었다.Instead of the compound Core-1 used in Synthesis Example 2, the compound Core-2 obtained in Preparation Example 2 was used, and 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6 Using 2-([1,1'-biphenyl]-4-yl)-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine instead of -phenyl-1,3,5-triazine Except, by performing the same procedure as in [Synthesis Example 2] to obtain the target compound 5.9 g (71% yield).
[LCMS] : 775[LCMS]: 775
[합성예 12] 화합물 42의 합성[Synthesis Example 12] Synthesis of Compound 42
합성예 2에서 사용된 화합물 Core-1 대신 준비예 2에서 얻은 화합물 Core-2를 사용하고, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 2-(4-chlorophenyl)-4-phenylquinazoline을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 4.5 g (수율 68 %)을 얻었다.Instead of the compound Core-1 used in Synthesis Example 2, the compound Core-2 obtained in Preparation Example 2 was used, and 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6 Except for using 2-(4-chlorophenyl)-4-phenylquinazoline instead of -phenyl-1,3,5-triazine, 4.5 g (yield 68%) of the target compound was prepared by performing the same procedure as in [Synthesis Example 2]. Got it.
[LCMS] : 672[LCMS]: 672
[합성예 13] 화합물 45의 합성[Synthesis Example 13] Synthesis of Compound 45
합성예 2에서 사용된 화합물 Core-1 대신 준비예 2에서 얻은 화합물 Core-2를 사용하고, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 5.0 g (수율 73 %)을 얻었다.Instead of the compound Core-1 used in Synthesis Example 2, the compound Core-2 obtained in Preparation Example 2 was used, and 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6 Except for using 2-(3'-chloro-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine instead of -phenyl-1,3,5-triazine Then, 5.0 g (yield 73%) of the target compound was obtained by performing the same procedure as in [Synthesis Example 2].
[LCMS] : 775[LCMS]: 775
[합성예 14] 화합물 49의 합성[Synthesis Example 14] Synthesis of Compound 49
합성예 2에서 사용된 화합물 Core-1 대신 준비예 2에서 얻은 화합물 Core-2를 사용하고, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 4-([1,1'-biphenyl]-4-yl)-6-(3'-chloro-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 9.6 g (수율 62 %)을 얻었다.Instead of the compound Core-1 used in Synthesis Example 2, the compound Core-2 obtained in Preparation Example 2 was used, and 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6 4-([1,1'-biphenyl]-4-yl)-6-(3'-chloro-[1,1'-biphenyl]-3-yl)- instead of -phenyl-1,3,5-triazine Except for using 2-phenylpyrimidine, the same procedure as in [Synthesis Example 2] was performed to obtain 9.6 g (62% yield) of the target compound.
[LCMS] : 851[LCMS]: 851
[합성예 15] 화합물 55의 합성[Synthesis Example 15] Synthesis of Compound 55
합성예 2에서 사용된 화합물 Core-1 대신 준비예 2에서 얻은 화합물 Core-2를 사용하고, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 4-(3'-chloro-[1,1'-biphenyl]-3-yl)-2,6-diphenylpyrimidine을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 3.4 g (수율 75 %)을 얻었다.Instead of the compound Core-1 used in Synthesis Example 2, the compound Core-2 obtained in Preparation Example 2 was used, and 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6 [Synthesis Example 2], except for using 4-(3'-chloro-[1,1'-biphenyl]-3-yl)-2,6-diphenylpyrimidine instead of -phenyl-1,3,5-triazine By following the same procedure as, 3.4 g of the title compound (75% yield) was obtained.
[LCMS] : 774[LCMS]: 774
[합성예 16] 화합물 59의 합성[Synthesis Example 16] Synthesis of Compound 59
합성예 2에서 사용된 화합물 Core-1 대신 준비예 2에서 얻은 화합물 Core-2를 사용하고, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 2-(3''-chloro-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 5.5 g (수율 63 %)을 얻었다.Instead of the compound Core-1 used in Synthesis Example 2, the compound Core-2 obtained in Preparation Example 2 was used, and 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6 2-(3''-chloro-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3 instead of -phenyl-1,3,5-triazine , Except for using 5-triazine, the same procedure as in [Synthesis Example 2] was performed to obtain 5.5 g of the target compound (yield 63%).
[LCMS] : 852[LCMS]: 852
[합성예 17] 화합물 62의 합성[Synthesis Example 17] Synthesis of Compound 62
합성예 1에서 사용된 화합물 Core-1 대신 준비예 3에서 얻은 화합물 Core-3을 사용하는 것을 제외하고는, [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.2 g (수율 77 %)을 얻었다.Except for using the compound Core-3 obtained in Preparation Example 3 instead of the compound Core-1 used in Synthesis Example 1, by performing the same procedure as in [Synthesis Example 1] to obtain 6.2 g (yield 77%) of the target compound .
[LCMS] : 699[LCMS]: 699
[합성예 18] 화합물 66의 합성[Synthesis Example 18] Synthesis of Compound 66
합성예 2에서 사용된 화합물 Core-1 대신 준비예 3에서 얻은 화합물 Core-3을 사용하고, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 4-([1,1'-biphenyl]-4-yl)-6-(4-chlorophenyl)-2-phenylpyrimidine을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 10.2 g (수율 71 %)을 얻었다.Using the compound Core-3 obtained in Preparation Example 3 instead of the compound Core-1 used in Synthesis Example 2, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6 [Synthesis Example 2], except that 4-([1,1'-biphenyl]-4-yl)-6-(4-chlorophenyl)-2-phenylpyrimidine was used instead of -phenyl-1,3,5-triazine ] And obtained the title compound 10.2 g (71% yield).
[LCMS] : 774[LCMS]: 774
[합성예 19] 화합물 73의 합성[Synthesis Example 19] Synthesis of Compound 73
합성예 2에서 사용된 화합물 Core-1 대신 준비예 3에서 얻은 화합물 Core-3을 사용하고, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 7.2 g (수율 59 %)을 얻었다.Using the compound Core-3 obtained in Preparation Example 3 instead of the compound Core-1 used in Synthesis Example 2, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6 Except for using 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine instead of -phenyl-1,3,5-triazine Then, 7.2 g (yield 59%) of the target compound was obtained by performing the same procedure as in [Synthesis Example 2].
[LCMS] : 775[LCMS]: 775
[합성예 20] 화합물 76의 합성[Synthesis Example 20] Synthesis of Compound 76
합성예 2에서 사용된 화합물 Core-1 대신 준비예 3에서 얻은 화합물 Core-3을 사용하고, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 2-([1,1'-biphenyl]-4-yl)-4-(3'-chloro-[1,1'-biphenyl]-3-yl)-6-phenyl-1,3,5-triazine을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 6.4 g (수율 70 %)을 얻었다.Using the compound Core-3 obtained in Preparation Example 3 instead of the compound Core-1 used in Synthesis Example 2, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6 2-([1,1'-biphenyl]-4-yl)-4-(3'-chloro-[1,1'-biphenyl]-3-yl)- instead of -phenyl-1,3,5-triazine Except that 6-phenyl-1,3,5-triazine was used, the same procedure as in [Synthesis Example 2] was performed to obtain 6.4 g (yield 70%) of the target compound.
[LCMS] : 852[LCMS]: 852
[합성예 21] 화합물 80의 합성[Synthesis Example 21] Synthesis of Compound 80
합성예 2에서 사용된 화합물 Core-1 대신 준비예 3에서 얻은 화합물 Core-3을 사용하고, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 4-([1,1'-biphenyl]-4-yl)-6-(4'-chloro-[1,1'-biphenyl]-3-yl)-2-phenylpyrimidine을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 8.6 g (수율 61 %)을 얻었다.Using the compound Core-3 obtained in Preparation Example 3 instead of the compound Core-1 used in Synthesis Example 2, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6 4-([1,1'-biphenyl]-4-yl)-6-(4'-chloro-[1,1'-biphenyl]-3-yl)- instead of -phenyl-1,3,5-triazine Except that 2-phenylpyrimidine was used, the same procedure as in [Synthesis Example 2] was performed to obtain 8.6 g (yield 61%) of the target compound.
[LCMS] : 851[LCMS]: 851
[합성예 22] 화합물 89의 합성[Synthesis Example 22] Synthesis of Compound 89
합성예 2에서 사용된 화합물 Core-1 대신 준비예 3에서 얻은 화합물 Core-3을 사용하고, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 2-(3''-chloro-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 4.5 g (수율 72 %)을 얻었다.Using the compound Core-3 obtained in Preparation Example 3 instead of the compound Core-1 used in Synthesis Example 2, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6 2-(3''-chloro-[1,1':3',1''-terphenyl]-3-yl)-4,6-diphenyl-1,3 instead of -phenyl-1,3,5-triazine , Except for using 5-triazine, 4.5 g (yield 72%) of the target compound was obtained by performing the same procedure as in [Synthesis Example 2].
[LCMS] : 852[LCMS]: 852
[합성예 23] 화합물 91의 합성[Synthesis Example 23] Synthesis of Compound 91
합성예 1에서 사용된 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-(8-bromodibenzo[b,d]furan-2-yl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, [합성예 1]과 동일한 과정을 수행하여 목적 화합물 9.3 g (수율 59 %)을 얻었다.Instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1, 2-(8-bromodibenzo[b,d]furan-2-yl)-4,6- Except that diphenyl-1,3,5-triazine was used, the same procedure as in [Synthesis Example 1] was performed to obtain 9.3 g (yield 59%) of the target compound.
[LCMS] : 789[LCMS]: 789
[합성예 24] 화합물 94의 합성[Synthesis Example 24] Synthesis of Compound 94
합성예 1에서 사용된 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-(6-bromodibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.6 g (수율 80 %)을 얻었다.2-(6-bromodibenzo[b,d]furan-4-yl)-4,6-instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1 Except that diphenyl-1,3,5-triazine was used, 6.6 g (yield 80%) of the target compound was obtained by performing the same procedure as in [Synthesis Example 1].
[LCMS] : 789[LCMS]: 789
[합성예 25] 화합물 96의 합성[Synthesis Example 25] Synthesis of Compound 96
합성예 1에서 사용된 화합물 Core-1 대신 준비예 3에서 얻은 화합물 Core-3을 사용하고, 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-(6-bromodibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine 을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 3.2 g (수율 75 %)을 얻었다.Instead of the compound Core-1 used in Synthesis Example 1, the compound Core-3 obtained in Preparation Example 3 was used, and instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine, 2-(6 -Bromodibenzo[b,d]furan-4-yl)-4,6-diphenyl-1,3,5-triazine was performed in the same manner as in [Synthesis Example 1], except that the target compound was 3.2 g (yield 75%).
[LCMS] : 789[LCMS]: 789
[합성예 26] 화합물 100의 합성[Synthesis Example 26] Synthesis of Compound 100
합성예 2에서 사용된 화합물 Core-1 대신 준비예 2에서 얻은 화합물 Core-2를 사용하고, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 2-(8-chlorodibenzo[b,d]furan-1-yl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 7.7 g (수율 42 %)을 얻었다.Instead of the compound Core-1 used in Synthesis Example 2, the compound Core-2 obtained in Preparation Example 2 was used, and 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6 Except for using 2-(8-chlorodibenzo[b,d]furan-1-yl)-4,6-diphenyl-1,3,5-triazine instead of -phenyl-1,3,5-triazine, [ Synthesis Example 2] was carried out in the same manner to obtain 7.7 g (yield 42%) of the target compound.
[LCMS] : 789[LCMS]: 789
[합성예 27] 화합물 103의 합성[Synthesis Example 27] Synthesis of Compound 103
합성예 2에서 사용된 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 2-(8-bromodibenzo[b,d]thiophen-2-yl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 5.4 g (수율 60 %)을 얻었다.Instead of 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine used in Synthesis Example 2, 2-(8-bromodibenzo[ Except for using b,d]thiophen-2-yl)-4,6-diphenyl-1,3,5-triazine, 5.4 g of the target compound (yield 60%) was performed in the same manner as in [Synthesis Example 2] ).
[LCMS] : 806[LCMS]: 806
[합성예 28] 화합물 123의 합성[Synthesis Example 28] Synthesis of Compound 123
합성예 1에서 사용된 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine 대신 2-(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, [합성예 1]과 동일한 과정을 수행하여 목적 화합물 10.5 g (수율 73 %)을 얻었다.Instead of 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1, 2-(7-bromo-9,9-dimethyl-9H-fluoren-2-yl)- Except that 4,6-diphenyl-1,3,5-triazine was used, the same procedure as in [Synthesis Example 1] was performed to obtain 10.5 g (yield 73%) of the target compound.
[LCMS] : 816[LCMS]: 816
[합성예 29] 화합물 113의 합성[Synthesis Example 29] Synthesis of Compound 113
합성예 1에서 사용된 화합물 Core-1 대신 준비예 2에서 얻은 화합물 Core-2를 사용하고, 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 2-(6-bromo-9,9-dimethyl-9H-fluoren-3-yl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.5 g (수율 66 %)을 얻었다.Instead of the compound Core-1 used in Synthesis Example 1, the compound Core-2 obtained in Preparation Example 2 was used, and 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6 Except for using 2-(6-bromo-9,9-dimethyl-9H-fluoren-3-yl)-4,6-diphenyl-1,3,5-triazine instead of -phenyl-1,3,5-triazine Then, 4.5 g (yield 66%) of the target compound was obtained by performing the same procedure as in [Synthesis Example 1].
[LCMS] : 816[LCMS]: 816
[합성예 30] 화합물 115의 합성[Synthesis Example 30] Synthesis of Compound 115
합성예 2에서 사용된 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 2-(3'-chloro-[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 8.1 g (수율 66 %)을 얻었다.2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine used in Synthesis Example 2 instead of 2-(3'-chloro Except for using -[1,1'-biphenyl]-3-yl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine, [ Synthesis Example 2] was carried out in the same manner to obtain 8.1 g of the title compound (66% yield).
[LCMS] : 866[LCMS]: 866
[합성예 31] 화합물 117의 합성[Synthesis Example 31] Synthesis of Compound 117
합성예 2에서 사용된 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 2-(4-chlorophenyl)-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 5.4 g (수율 61 %)을 얻었다.2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine used in Synthesis Example 2 instead of 2-(4-chlorophenyl) Except for using -4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine, 5.4 g of the target compound was carried out in the same manner as in [Synthesis Example 2] (Yield 61%) was obtained.
[LCMS] : 789[LCMS]: 789
[합성예 32] 화합물 119의 합성[Synthesis Example 32] Synthesis of Compound 119
합성예 2에서 사용된 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine 대신 2-(8-chlorodibenzo[b,d]furan-1-yl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine을 사용한 것을 제외하고는, [합성예 2]와 동일한 과정을 수행하여 목적 화합물 11.5 g (수율 84 %)을 얻었다.Instead of 2-([1,1'-biphenyl]-4-yl)-4-(3-chlorophenyl)-6-phenyl-1,3,5-triazine used in Synthesis Example 2, 2-(8-chlorodibenzo[ Except for using b,d]furan-1-yl)-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine, [Synthesis Example 2] Following the same procedure as, 11.5 g of the title compound (84% yield) was obtained.
[LCMS] : 880[LCMS]: 880
[실시예 1] 청색 유기 전계 발광 소자의 제조[Example 1] Preparation of blue organic electroluminescent device
합성예 1에서 화합물 2를 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기와 같이 청색 유기 전계 발광 소자를 제조하였다.In Synthesis Example 1, compound 2 was subjected to high-purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was manufactured as follows.
ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고, 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.The glass substrate coated with a thin film of ITO (Indium tin oxide) with a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonically clean with a solvent such as isopropyl alcohol, acetone, methanol, etc., dry, transfer to a UV OZONE cleaner (Power Sonic 405, Hwashin Tech), and then use UV for 5 minutes. It was cleaned and the substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, DS-205 (80 nm) / NPB (15 nm) / 95wt%의 ADN + 5 wt%의 DS-405 (30nm) / 화합물 2 (30 nm)/ LiF (1 nm)/ Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제조하였다. 이때 사용된 NPB 및 ADN의 구조는 다음과 같고, DS-205 및 DS-405는 ㈜두산전자 BG 제품이다.On the ITO transparent electrode prepared as above, DS-205 (80 nm) / NPB (15 nm) / 95 wt% of ADN + 5 wt% of DS-405 (30 nm) / Compound 2 (30 nm) / LiF (1 nm ) / Al (200 nm) was stacked in order to prepare an organic electroluminescent device. The structure of NPB and ADN used at this time is as follows, and DS-205 and DS-405 are Doosan Electronics BG products.
[실시예 2~13] 청색 유기 전계 발광 소자의 제작[Examples 2 to 13] Fabrication of a blue organic electroluminescent device
실시예 1에서 전자 수송층 형성시 전자 수송층 물질로 사용된 화합물 2 대신하기 표 1에 기재된 화합물을 각각 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다.A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of the compound 2 used as the electron transport layer material when forming the electron transport layer in Example 1.
[비교예 1] 청색 유기 전계 발광 소자의 제조[Comparative Example 1] Preparation of blue organic electroluminescent device
실시예 1에서 전자 수송층 형성시 전자 수송층 물질로 사용된 화합물 2 대신 Alq3을 30nm로 증착하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다. 이때 사용된 Alq3의 구조는 다음과 같다. In Example 1, when forming the electron transport layer, a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq 3 was deposited at 30 nm instead of the compound 2 used as the electron transport layer material. The structure of Alq 3 used at this time is as follows.
[비교예 2] 청색 유기 전계 발광 소자의 제조[Comparative Example 2] Preparation of blue organic electroluminescent device
실시예 1에서 사용된 화합물 2 대신 화합물 A를 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다. 이때 사용된 화합물 A의 구조는 다음과 같다. A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound A was used instead of Compound 2 used in Example 1. The structure of Compound A used at this time is as follows.
[비교예 3] 청색 유기 전계 발광 소자의 제조[Comparative Example 3] Preparation of blue organic electroluminescent device
실시예 1에서 사용된 화합물 2 대신 화합물 B를 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다. 이때 사용된 화합물 B의 구조는 다음과 같다. A blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound B was used instead of Compound 2 used in Example 1. The structure of compound B used at this time is as follows.
[평가예 1][Evaluation Example 1]
실시예 1 내지 13 및 비교예 1 내지 3에서 각각 제조된 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율, 발광파장을 측정하였고, 그 결과를 하기 표 1에 나타내었다.For the organic electroluminescent devices prepared in Examples 1 to 13 and Comparative Examples 1 to 3, respectively, driving voltage, current efficiency, and emission wavelength at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 1 below. Done.
| 샘플Sample | 전자수송층Electron transport layer | 구동전압(V)Driving voltage (V) | 발광피크(nm)Emission peak (nm) | 전류효율(cd/A)Current efficiency (cd/A) |
| 실시예 1Example 1 | 화합물 2Compound 2 | 3.93.9 | 450450 | 9.29.2 |
| 실시예 2Example 2 | 화합물 3Compound 3 | 3.93.9 | 452452 | 9.09.0 |
| 실시예 3Example 3 | 화합물 10Compound 10 | 3.63.6 | 451451 | 8.98.9 |
| 실시예 4Example 4 | 화합물 23Compound 23 | 4.34.3 | 452452 | 9.39.3 |
| 실시예 5Example 5 | 화합물 34Compound 34 | 3.63.6 | 450450 | 8.68.6 |
| 실시예 6Example 6 | 화합물 42Compound 42 | 3.53.5 | 452452 | 9.49.4 |
| 실시예 7Example 7 | 화합물 59Compound 59 | 3.83.8 | 451451 | 8.28.2 |
| 실시예 8Example 8 | 화합물 62Compound 62 | 3.83.8 | 452452 | 8.98.9 |
| 실시예 9Example 9 | 화합물 66Compound 66 | 3.83.8 | 451451 | 8.78.7 |
| 실시예 10Example 10 | 화합물 80Compound 80 | 3.33.3 | 452452 | 9.19.1 |
| 실시예 11Example 11 | 화합물 91Compound 91 | 3.43.4 | 450450 | 9.29.2 |
| 실시예 12Example 12 |
화합물 100 |
3.73.7 | 451451 | 9.59.5 |
| 실시예 13Example 13 | 화합물 109Compound 109 | 3.53.5 | 452452 | 9.09.0 |
| 비교예 1Comparative Example 1 | Alq3 Alq 3 | 4.84.8 | 457457 | 5.85.8 |
| 비교예 2Comparative Example 2 | AA | 4.54.5 | 458458 | 6.56.5 |
| 비교예 3Comparative Example 3 | BB | 4.64.6 | 457457 | 7.17.1 |
상기 표 1에 나타낸 바와 같이, 본 발명에 따른 화합물을 전자수송층 재료로 사용한 실시예 1~13의 청색 유기 전계 발광 소자는 종래의 Alq3를 전자수송층 재료로 적용한 비교예 1의 청색 유기 전계 발광 소자, 치환기의 결합위치가 상이한 화합물을 포함한 비교예 2의 청색 유기 전계 발광 소자, 및 링커 없이 직접 치환기가 도입된 화합물을 포함한 비교예 3의 청색 유기 전계 발광 소자보다 전류효율 및 구동전압이 우수한 성능을 나타내는 것을 알 수 있었다.As shown in Table 1, the blue organic electroluminescent devices of Examples 1 to 13 using the compound according to the present invention as an electron transport layer material were the blue organic electroluminescent devices of Comparative Example 1 in which Alq 3 was applied as the electron transport layer material. , The blue organic electroluminescent device of Comparative Example 2 including a compound having a different bonding position of the substituent, and the blue organic electroluminescent device of Comparative Example 3 including a compound in which a substituent was introduced directly without a linker. I could see that it was indicated.
[실시예 2] 청색 유기 EL 소자의 제조[Example 2] Fabrication of blue organic EL device
합성예 1에서 합성된 화합물 2를 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 아래의 과정에 따라 청색 유기 EL 소자를 제작하였다.After compound 2 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, a blue organic EL device was manufactured according to the following procedure.
ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후, UV OZONE 세정기(Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.The glass substrate coated with a thin film of ITO (Indium tin oxide) with a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonically clean with a solvent such as isopropyl alcohol, acetone, methanol, etc., dry, transfer to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and clean the substrate for 5 minutes using UV And transferred the substrate to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에, DS-205 (80 nm) / NPB (15 nm) / 95 wt%의 ADN + 5 wt%의 DS-405 (㈜두산전자, 30nm) / 화합물 2 (5 nm) / Alq3 (25 nm) / LiF (1 nm) / Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제조하였다.On the ITO transparent electrode prepared as above, DS-205 (80 nm) / NPB (15 nm) / 95 wt% of ADN + 5 wt% of DS-405 (Doosan Electronics, 30 nm) / Compound 2 (5 nm) / Alq 3 (25 nm) / LiF (1 nm) / Al (200 nm) were stacked in this order to prepare an organic electroluminescent device.
이때 사용된 NPB, ADN 및 Alq3의 구조는 다음과 같고, DS-205 및 DS-405는 ㈜두산전자 BG 제품이다.The structures of NPB, ADN and Alq 3 used at this time are as follows, and DS-205 and DS-405 are Doosan Electronics BG products.
[실시예 14] ~ [실시예 27] 청색 유기 EL 소자의 제조[Example 14] to [Example 27] Preparation of blue organic EL device
실시예 14에서 전자수송 보조층 물질로 사용된 화합물 2 대신 하기 표 2에 기재된 화합물을 각각 전자수송보조층 물질로 사용하는 것을 제외하고는, 실시예 14 와 동일하게 수행하여 청색 유기 EL 소자를 제조하였다.A blue organic EL device was manufactured in the same manner as in Example 14, except that the compounds shown in Table 2 were used as electron transport auxiliary layer materials instead of compound 2 used as the electron transport auxiliary layer material in Example 14. I did.
[비교예 4] 청색 유기 전계 발광 소자의 제조[Comparative Example 4] Preparation of blue organic electroluminescent device
실시예 14에서 전자수송보조층 물질로 사용된 화합물 2 를 사용하지 않고, 전자 수송층 물질인 Alq3를 25 nm 대신 30 nm로 증착하는 것을 제외하고는, 실시예 14와 동일하게 수행하여 청색 유기 EL 소자를 제작하였다. Blue organic EL was carried out in the same manner as in Example 14, except that the compound 2 used as the electron transport auxiliary layer material in Example 14 was not used, and Alq 3 as the electron transport layer material was deposited at 30 nm instead of 25 nm. The device was fabricated.
[비교예 5] 청색 유기 전계 발광 소자의 제조[Comparative Example 5] Preparation of blue organic electroluminescent device
실시예 14에서 화합물 1 대신 화합물 A를 사용하는 것을 제외하고는, 실시예 14와 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다. 이때 사용된 화합물 A의 구조는 비교예 2에 기재된 바와 같다. A blue organic electroluminescent device was manufactured in the same manner as in Example 14, except that Compound A was used instead of Compound 1 in Example 14. The structure of Compound A used at this time is as described in Comparative Example 2.
[비교예 6] 청색 유기 전계 발광 소자의 제조[Comparative Example 6] Preparation of blue organic electroluminescent device
실시예 14에서 화합물 1 대신 화합물 B를 사용하는 것을 제외하고는, 실시예 14와 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다. 이때 사용된 화합물 B의 구조는 비교예 3에 기재된 바와 같다. A blue organic electroluminescent device was manufactured in the same manner as in Example 14, except that Compound B was used instead of Compound 1 in Example 14. The structure of Compound B used at this time is as described in Comparative Example 3.
[평가예 2][Evaluation Example 2]
실시예 14 내지 27 및 비교예 4 내지 6에서 각각 제조된 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 발광파장, 전류효율을 측정하였고, 그 결과를 하기 표 2에 나타내었다.For the organic electroluminescent devices prepared in Examples 14 to 27 and Comparative Examples 4 to 6, respectively, driving voltage, emission wavelength, and current efficiency at a current density of 10 mA/cm 2 were measured, and the results are shown in Table 2 below. Done.
| 샘플Sample | 전자수송보조층Electronic transport auxiliary layer | 구동 전압(V)Driving voltage (V) | 발광 피크(nm)Emission peak (nm) | 전류효율cd/A)Current efficiency cd/A) |
| 실시예 14Example 14 | 화합물 2Compound 2 | 3.33.3 | 450450 | 9.39.3 |
| 실시예 15Example 15 | 화합물 5Compound 5 | 3.23.2 | 450450 | 9.29.2 |
| 실시예 16Example 16 | 화합물 13Compound 13 | 3.53.5 | 452452 | 8.88.8 |
| 실시예 17Example 17 | 화합물 15Compound 15 | 3.53.5 | 451451 | 9.29.2 |
| 실시예 18Example 18 | 화합물 28Compound 28 | 3.83.8 | 450450 | 9.49.4 |
| 실시예 19Example 19 | 화합물 29Compound 29 | 4.04.0 | 450450 | 8.58.5 |
| 실시예 20Example 20 | 화합물 45Compound 45 | 3.43.4 | 451451 | 8.98.9 |
| 실시예 21Example 21 | 화합물 49Compound 49 | 3.33.3 | 450450 | 9.09.0 |
| 실시예 22Example 22 | 화합물 73Compound 73 | 3.53.5 | 451451 | 9.29.2 |
| 실시예 23Example 23 | 화합물 76Compound 76 | 3.63.6 | 452452 | 8.38.3 |
| 실시예 24Example 24 | 화합물 94Compound 94 | 3.73.7 | 450450 | 9.29.2 |
| 실시예 25Example 25 | 화합물 96Compound 96 | 3.73.7 | 451451 | 9.39.3 |
| 실시예 26Example 26 | 화합물 103Compound 103 | 3.53.5 | 450450 | 9.39.3 |
| 실시예 27Example 27 | 화합물 113Compound 113 | 3.33.3 | 450450 | 8.58.5 |
| 비교예 4Comparative Example 4 | -- | 4.64.6 | 455455 | 6.26.2 |
| 비교예 5Comparative Example 5 | AA | 4.54.5 | 455455 | 6.86.8 |
| 비교예 6Comparative Example 6 | BB | 4.24.2 | 456456 | 7.27.2 |
표 2에 나타낸 바와 같이, 본 발명에 따른 화합물을 전자수송보조층 물질로 사용한 실시예 14~27의 청색 유기 EL 소자는 전자수송보조층 없는 비교예 4의 청색 유기 전계 발광 소자, 치환기의 결합위치가 다른 화합물을 전자수송보조층 물질로 사용한 비교예 5의 청색 유기 전계 발광 소자, 및 링커 없이 치환기가 직접 결합된 화합물을 전자수송보조층 물질로 사용한 비교예 6의 청색 유기 EL 소자에 비해 전류 효율 및 구동전압 면에서 우수한 성능을 나타내는 것을 알 수 있었다.As shown in Table 2, the blue organic EL device of Examples 14 to 27 using the compound according to the present invention as an electron transport auxiliary layer material is the blue organic electroluminescent device of Comparative Example 4 without an electron transport auxiliary layer, and the bonding position of the substituent. Current efficiency compared to the blue organic EL device of Comparative Example 5 in which a compound of which is different is used as an electron transport auxiliary layer material, and the blue organic EL device of Comparative Example 6 in which a compound having a substituent directly bonded without a linker is used as an electron transport auxiliary layer material. And it was found that exhibiting excellent performance in terms of driving voltage.
Claims (11)
- 하기 화학식 1로 표시되는 화합물:Compound represented by the following formula 1:[화학식 1] [Formula 1]
(상기 화학식 1에서, (In Formula 1,n은 1 내지 3의 정수이고,n is an integer of 1 to 3,L1은 C6~C40의 아릴렌기 및 핵원자수 5 내지 40의 헤테로아릴렌기로 이루어진 군에서 선택되고,L 1 is selected from the group consisting of an arylene group of C 6 to C 40 and a heteroarylene group having 5 to 40 nuclear atoms,Z1 내지 Z3는 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 CR1이고, 다만 Z1 내지 Z3 중 적어도 2개는 N이며,Z 1 to Z 3 are the same as or different from each other, and each independently N or CR 1 , provided that at least two of Z 1 to Z 3 are N,R1은 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 또는 인접한 기와 결합하여 축합 고리를 형성하고,R 1 is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 Cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , C 6 to C 60 Aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 Selected from the group consisting of an arylphosphine group, a C 6 ~ C 60 arylphosphine oxide group and a C 6 ~ C 60 arylamine group, or combined with an adjacent group to form a condensed ring,Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군에서 선택되며,Ar 1 and Ar 2 are the same as or different from each other, each independently selected from the group consisting of an aryl group of C 6 to C 60 and a heteroaryl group having 5 to 60 nuclear atoms,상기 L1의 아릴렌기와 헤테로아릴렌기, R1의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기와 아릴아민기, 및 Ar1 및 Ar2의 아릴기와 헤테로아릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이함).Arylene group and a heteroaryl group, an alkyl group R 1 of said L 1, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl Group, alkyl boron group, aryl boron group, arylphosphine group, arylphosphine oxide group and arylamine group, and the aryl and heteroaryl groups of Ar 1 and Ar 2 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, 3 to 40 nuclear atoms heterocycloalkyl group, C 6 ~ C 60 Aryl group, heteroaryl group having 5 to 60 nuclear atoms, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkylsilyl group, C 6 to C 60 aryl silyl group, C 1 ~ C 40 group, the alkyl boron C 6 ~ C group 60 arylboronic of, C 6 ~ aryl phosphine oxide of C 60 aryl phosphine group, C 6 ~ C 60 of the group, and a C 6 ~ C It is substituted or unsubstituted with one or more substituents selected from the group consisting of 60 arylamine groups, and in this case, when the substituents are plural, they are the same or different from each other). - 제1항에 있어서,The method of claim 1,상기 화학식 1로 표시되는 화합물은 하기 화학식 2 내지 4 중 어느 하나로 표시되는 화합물:The compound represented by Formula 1 is a compound represented by any one of the following Formulas 2 to 4:[화학식 2] [Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
(상기 화학식 2 내지 4에서,(In Formulas 2 to 4,n, L1, Z1 내지 Z3, Ar1 및 Ar2는 각각 제1항에 정의된 바와 같음).n, L 1 , Z 1 to Z 3 , Ar 1 and Ar 2 are each as defined in claim 1). - 제1항에 있어서,The method of claim 1,상기 화학식 1로 표시되는 화합물은 하기 화학식 5 또는 6으로 표시되는 화합물:The compound represented by Formula 1 is a compound represented by the following Formula 5 or 6:[화학식 5] [Formula 5]
[화학식 6][Formula 6]
(상기 화학식 5 및 6에서,(In Formulas 5 and 6,Z1 내지 Z3, Ar1 및 Ar2는 각각 제1항에 정의된 바와 같고,Z 1 to Z 3 , Ar 1 and Ar 2 are each as defined in claim 1,a는 0 내지 4의 정수이고, a is an integer from 0 to 4,b 및 c는 각각 0 내지 3의 정수이며,b and c are each an integer of 0 to 3,L2 및 L3는 서로 동일하거나 상이하고, 각각 독립적으로 단일결합이거나, 또는 C6~C20의 아릴렌기 및 핵원자수 5 내지 20의 헤테로아릴렌기로 이루어진 군에서 선택되고,L 2 and L 3 are the same as or different from each other, and each independently a single bond, or is selected from the group consisting of an arylene group of C 6 to C 20 and a heteroarylene group of 5 to 20 nuclear atoms,Y1은 O, S 및 C(R5)(R6)으로 이루어진 군에서 선택되고, Y 1 is selected from the group consisting of O, S and C(R 5 )(R 6 ),R2 내지 R6은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,R 2 to R 6 are the same as or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, 3 to 40 nuclear atom heterocycloalkyl group, C 6 to C 60 aryl group, 5 to 60 nuclear atom heteroaryl group, C 1 to C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C the group of boron 60 aryl, C 6 ~ C 60 aryl phosphine group, is selected from the group consisting of C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ C 60 aryl group of an amine of,상기 L2 및 L3의 아릴렌기와 헤테로아릴렌기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환되며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이함).The arylene group and heteroarylene group of L 2 and L 3 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 Alkynyl group, C 3 to C 40 cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyl of C 1 to C 40 Oxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C aryl phosphine oxide 60 group and a C 6 ~ C 60 aryl group is unsubstituted or substituted by one substituent at least one selected from the group consisting of amine groups of, wherein When the above substituents are plural, they are the same or different from each other). - 제1항에 있어서,The method of claim 1,상기 화학식 1로 표시되는 화합물은 하기 화학식 7 내지 12 중 어느 하나로 표시되는 화합물:The compound represented by Formula 1 is a compound represented by any one of the following Formulas 7 to 12:[화학식 7] [Formula 7]
[화학식 8][Formula 8]
[화학식 9][Formula 9]
[화학식 10][Formula 10]
[화학식 11][Formula 11]
[화학식 12][Formula 12]
(상기 화학식 7 내지 12에서,(In Formulas 7 to 12,Z1 내지 Z3, Ar1 및 Ar2는 각각 제1항에 정의된 바와 같고,Z 1 to Z 3 , Ar 1 and Ar 2 are each as defined in claim 1,R5 및 R6은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 중수소, 할로겐기, 시아노기, 니트로기, 아미노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택됨).R 5 and R 6 are the same as or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, 3 to 40 nuclear atom heterocycloalkyl group, C 6 to C 60 aryl group, 5 to 60 nuclear atom heteroaryl group, C 1 to C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 arylboronic group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ selected from the group consisting of an aryl amine of the C 60). - 제1항에 있어서,The method of claim 1,상기 화학식 1에서, L1은 하기 링커기 L1 내지 L6으로 이루어진 군에서 선택된 링커기인, 화합물:In Formula 1, L 1 is a linker group selected from the group consisting of the following linker groups L1 to L6, a compound:.
. - 제1항에 있어서,The method of claim 1,상기 화학식 1의 모이어티는 하기 치환기 EWG1 내지 EWG17로 이루어진 군에서 선택된 치환기인, 화합물:The moiety of Formula 1 is a compound selected from the group consisting of the following substituents EWG1 to EWG17:.
. - 제1항에 있어서,The method of claim 1,상기 화학식 1로 표시되는 화합물은 하기 화합물 (1) 내지 화합물 (122)로 이루어진 군에서 선택된 것인, 화합물:The compound represented by Formula 1 is selected from the group consisting of the following compounds (1) to (122), a compound:
.
. - (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic material layer interposed between the anode and the cathode,상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항 내지 제7항 중 어느 한 항에 기재된 유기 화합물을 포함하는 유기 전계 발광 소자.An organic electroluminescent device comprising the organic compound according to any one of claims 1 to 7, at least one of the one or more organic material layers.
- 제8항에 있어서,The method of claim 8,상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층을 포함하고,The one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer,상기 유기 화합물을 포함하는 유기물층은 발광층 또는 전자수송층인, 유기 전계 발광 소자.The organic material layer including the organic compound is an emission layer or an electron transport layer, an organic electroluminescent device.
- 제8항에 있어서,The method of claim 8,상기 발광층은 p형 호스트 및 n형 호스트를 포함하고,The emission layer includes a p-type host and an n-type host,상기 n형 호스트는 상기 유기 화합물을 포함하는 것인, 유기 전계 발광 소자.The n-type host comprises the organic compound, an organic electroluminescent device.
- 제8항에 있어서,The method of claim 8,상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송 보조층, 전자수송층 및 전자주입층을 포함하고,The one or more organic material layers include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer,상기 유기 화합물을 포함하는 유기물층은 상기 전자수송 보조층인, 유기 전계 발광 소자.The organic material layer including the organic compound is the electron transport auxiliary layer, an organic electroluminescent device.
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|---|---|---|---|---|
| KR20170091712A (en) * | 2014-12-01 | 2017-08-09 | 메르크 파텐트 게엠베하 | Materials for organic electroluminescent devices |
| KR20170126559A (en) * | 2016-05-09 | 2017-11-20 | 삼성디스플레이 주식회사 | Polycyclic compound and organic electroluminescence device including the same |
| JP2019014681A (en) * | 2017-07-07 | 2019-01-31 | 彩豐精技股▲分▼有限公司 | Compound and organic electronic device using the same |
| KR20190010273A (en) * | 2017-07-21 | 2019-01-30 | 니켐 파인 테크놀로지 컴퍼니 리미티드 | Novel compound and organic electronic device comprising the same |
| KR20190011128A (en) * | 2017-07-24 | 2019-02-01 | 니켐 파인 테크놀로지 컴퍼니 리미티드 | Novel compound and organic electronic device comprising the same |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20200109798A (en) | 2020-09-23 |
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