WO2017188596A1 - 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 - Google Patents
유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자 Download PDFInfo
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- WO2017188596A1 WO2017188596A1 PCT/KR2017/002779 KR2017002779W WO2017188596A1 WO 2017188596 A1 WO2017188596 A1 WO 2017188596A1 KR 2017002779 W KR2017002779 W KR 2017002779W WO 2017188596 A1 WO2017188596 A1 WO 2017188596A1
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- Prior art keywords
- group
- aryl
- formula
- alkyl
- compound
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 89
- 125000003118 aryl group Chemical group 0.000 claims description 94
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 37
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 36
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 30
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- 125000000304 alkynyl group Chemical group 0.000 claims description 27
- -1 aryl phosphine Chemical compound 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 125000004429 atom Chemical group 0.000 claims description 24
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 21
- 125000005104 aryl silyl group Chemical group 0.000 claims description 21
- 239000011368 organic material Substances 0.000 claims description 21
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 238000002347 injection Methods 0.000 claims description 15
- 239000007924 injection Substances 0.000 claims description 15
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 14
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- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 230000005525 hole transport Effects 0.000 claims description 9
- 125000005264 aryl amine group Chemical group 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 8
- 230000005494 condensation Effects 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 4
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- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
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- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 14
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 13
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- 230000000052 comparative effect Effects 0.000 description 12
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- 239000000243 solution Substances 0.000 description 10
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- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 6
- QPEFLTYNPXRWKV-UHFFFAOYSA-N 2-bromo-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=C(Br)N=C21 QPEFLTYNPXRWKV-UHFFFAOYSA-N 0.000 description 5
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- SRNKZYRMFBGSGE-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CN=C21 SRNKZYRMFBGSGE-UHFFFAOYSA-N 0.000 description 4
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- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 3
- WRQHNSKKYGHTLO-UHFFFAOYSA-N 1h-phenanthro[9,10-d]imidazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1NC=N2 WRQHNSKKYGHTLO-UHFFFAOYSA-N 0.000 description 3
- VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 3
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
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- POFDSYGXHVPQNX-UHFFFAOYSA-N triazolo[1,5-a]pyrimidine Chemical compound C1=CC=NC2=CN=NN21 POFDSYGXHVPQNX-UHFFFAOYSA-N 0.000 description 3
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 2
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- QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 2
- UZBYKKGCTOQGOM-UHFFFAOYSA-N 2-(4-bromophenyl)-4,6-dinaphthalen-2-yl-1,3,5-triazine Chemical compound BrC1=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC2=CC=CC=C2C=C1)C1=CC2=CC=CC=C2C=C1 UZBYKKGCTOQGOM-UHFFFAOYSA-N 0.000 description 2
- MRPUMSPLZXTYCU-UHFFFAOYSA-N 2-(4-chlorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine Chemical compound C1=CC(Cl)=CC=C1C1=NN2C=CC=NC2=N1 MRPUMSPLZXTYCU-UHFFFAOYSA-N 0.000 description 2
- JVTWZWXZDLOYQZ-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)phenyl]-4,6-dinaphthalen-2-yl-1,3,5-triazine Chemical compound ClC1=CC=C(C=C1)C1=CC=C(C=C1)C1=NC(=NC(=N1)C1=CC2=CC=CC=C2C=C1)C1=CC2=CC=CC=C2C=C1 JVTWZWXZDLOYQZ-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- 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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
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Definitions
- the present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, a compound having excellent electron transport ability and an organic light emitting device having improved characteristics such as luminous efficiency, driving voltage, and lifetime by including the same in at least one organic material layer. It relates to an electroluminescent element.
- 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 its function.
- the light emitting layer forming material of the organic EL device may be classified into blue, green, and red light emitting materials according to light emission colors. In addition, yellow and orange light emitting materials are also used as light emitting materials to realize better natural colors.
- a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
- the dopant material may be divided 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. The development of such phosphorescent materials can theoretically improve luminous efficiency up to 4 times compared to fluorescence, and thus, attention has been focused on phosphorescent dopants as well as phosphorescent host materials.
- NPB hole blocking layer
- BCP hole blocking layer
- Alq 3 hole blocking layer
- anthracene derivatives have been reported as fluorescent dopant / host materials in the light emitting material.
- phosphorescent materials having great advantages in terms of efficiency improvement among light emitting materials include metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2, such as blue, green, and red dopant materials. Is being used.
- CBP has shown excellent properties as a phosphorescent host material.
- the present invention can be applied to an organic electroluminescent device, and an object of the present invention is to provide a novel organic compound having excellent electron injection and electron transport ability.
- Another object of the present invention is to provide an organic electroluminescent device including the novel organic compound, which exhibits low driving voltage and high luminous efficiency and has an improved lifetime.
- the present invention to achieve the above object provides a compound represented by the following formula (1).
- Z 1 and Z- 2 are the same as or different from each other, and each independently N or C (R 2 ),
- X 1 to X 5 are the same as or different from each other, and each independently N or C (R 3 ),
- L 1 is a bond, an arylene group having 6 to 18 carbon atoms or a heteroarylene group having 5 to 18 nuclear atoms,
- Ar 1 is a substituent of Formula 2 or 3
- any one of Y 11 and Y 11 and Y 7 may be condensed with the ring represented by Formula 4 to form a condensed ring;
- n is an integer from 0 to 4,
- Y 1 to Y 6 which do not form a condensation with the ring represented by Formula 4 are the same as or different from each other, and each independently N or C (R 4 ),
- Y 7 is N (R 5 ) or C (R 6 ) (R 7 ),
- Y 8 to Y 11 which do not form a condensation with the ring represented by Formula 4 are the same as or different from each other, and are each independently N or C (R 8 ),
- R 2 and R 3 are the same or different, each independently represent hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, an alkyl of C 1 ⁇ C 40 Oxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ 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 is selected from the pingi, C 6 ⁇ C 60 aryl phosphine oxide group, and a
- R 1 and R 4 to R 8 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 Selected from the group consisting of -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, and C 5 -60 heteroaryl group May combine with adjacent groups to form a condensed ring,
- alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group , Arylphosphine oxide group and arylamine group are each independently C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nucleus aryloxy atoms, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ⁇ C 40 alkyloxy group, the C 6 ⁇ C 60 of, C 3 ⁇ C 40 alkylsilyl group, C
- the present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer
- an organic electroluminescent device comprising a compound represented by the formula (1).
- alkyl refers to a monovalent substituent derived from a straight or branched chain 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 in the present invention refers to a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
- Alkynyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
- aryl means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings.
- a form in which two or more rings are attached to each other (pendant) or condensed may also be included.
- Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
- Heteroaryl in the present invention means a monovalent substituent derived from monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
- a form in which two or more rings are pendant or condensed with each other may be included, and may also include a form in which the two or more rings are condensed with an aryl group.
- heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
- 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carb
- aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms.
- R means aryl having 6 to 60 carbon atoms.
- Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
- alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means alkyl having 1 to 40 carbon atoms, and includes a linear, branched or cyclic structure. can do.
- alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
- the amine is a monovalent substituent represented by R 1 R 2 N-, wherein R 1 and R 2 are each independently alkyl having 1 to 60 carbon atoms, aryl having 6 to 60 carbon atoms and having 5 to 60 nuclear atoms. Heteroaryl.
- Cycloalkyl in the present invention means monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms.
- Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
- Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, S or Se Is substituted with a hetero atom such as Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
- alkylsilyl is silyl substituted with alkyl having 1 to 40 carbon atoms
- arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.
- Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
- the present invention is an organic electroluminescent device comprising an anode, a cathode and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic electroluminescent device comprising.
- the compound of the present invention can be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and luminescent properties.
- the compound of the present invention when used as an electron transport material, it is possible to manufacture an organic electroluminescent device having a lower driving voltage, higher efficiency and longer life than conventional electron transport materials, and furthermore, a full color display with improved performance and lifetime. Panels can also be manufactured.
- Z 1 and Z- 2 are the same as or different from each other, and each independently N or C (R 2 ),
- X 1 to X 5 are the same as or different from each other, and each independently N or C (R 3 ),
- L 1 is a bond, an arylene group having 6 to 18 carbon atoms or a heteroarylene group having 5 to 18 nuclear atoms,
- Ar 1 is a substituent of Formula 2 or 3
- any one of Y 11 and Y 11 and Y 7 may be condensed with the ring represented by Formula 4 to form a condensed ring;
- n is an integer from 0 to 4,
- Y 1 to Y 6 which do not form a condensation with the ring represented by Formula 4 are the same as or different from each other, and each independently N or C (R 4 ),
- Y 7 is N (R 5 ) or C (R 6 ) (R 7 ),
- Y 8 to Y 11 which do not form a condensation with the ring represented by Formula 4 are the same as or different from each other, and are each independently N or C (R 8 ),
- R 2 and R 3 are the same or different, each independently represent hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, an alkyl of C 1 ⁇ C 40 Oxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ 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 is selected from the pingi, C 6 ⁇ C 60 aryl phosphine oxide group, and a
- R 1 and R 4 to R 8 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 Selected from the group consisting of -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, and C 5 -60 heteroaryl group May combine with adjacent groups to form a condensed ring,
- alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group , Arylphosphine oxide group and arylamine group are each independently C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nucleus aryloxy atoms, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ⁇ C 40 alkyloxy group, the C 6 ⁇ C 60 of, C 3 ⁇ C 40 alkylsilyl group, C
- the luminous efficiency is good and the lifespan characteristics of the material are excellent, and the driving life of the device is very excellent, and there is an advantage of manufacturing an OLED device with improved power consumption by inducing an increase in power efficiency. .
- novel organic compound provided by the present invention is characterized by represented by the following formula (1):
- Z 1 and Z- 2 are the same as or different from each other, and each independently N or C (R 2 ),
- X 1 to X 5 are the same as or different from each other, and each independently N or C (R 3 ),
- L 1 is a bond, an arylene group having 6 to 18 carbon atoms or a heteroarylene group having 5 to 18 nuclear atoms,
- Ar 1 is a substituent of Formula 2 or 3
- any one of Y 11 and Y 11 and Y 7 may be condensed with the ring represented by Formula 4 to form a condensed ring;
- n is an integer from 0 to 4,
- Y 1 to Y 6 which do not form a condensation with the ring represented by Formula 4 are the same as or different from each other, and each independently N or C (R 4 ),
- Y 7 is N (R 5 ) or C (R 6 ) (R 7 ),
- Y 8 to Y 11 which do not form a condensation with the ring represented by Formula 4 are the same as or different from each other, and are each independently N or C (R 8 ),
- R 2 and R 3 are the same or different, each independently represent hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, an alkyl of C 1 ⁇ C 40 Oxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ 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 is selected from the pingi, C 6 ⁇ C 60 aryl phosphine oxide group, and a
- R 1 and R 4 to R 8 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 Selected from the group consisting of -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, and C 5 -60 heteroaryl group May combine with adjacent groups to form a condensed ring,
- alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group , Arylphosphine oxide group and arylamine group are each independently C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, nucleus aryloxy atoms, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ⁇ C 40 alkyloxy group, the C 6 ⁇ C 60 of, C 3 ⁇ C 40 alkylsilyl group, C
- the novel electron withdrawing group (EWG) core of the triazolopyridine skeleton is characterized by the above formula (1).
- EWG group which is not used well in the field of electronic materials in the past, has excellent thermal stability due to its excellent electron withdrawing power and high glass transition temperature. It is excellent in luminous ability. Therefore, when the organic electroluminescent device includes the compound of Formula 1, the driving voltage, efficiency, lifespan, etc. of the device may be improved. In addition, the triplet energy of the developed materials is high, resulting in an increase in efficiency due to the triplet-triplet fusion (TTF) effect of the latest ETL materials.
- TTF triplet-triplet fusion
- Compounds of Formula 1 are hetero aryl groups introduced structure is a material having excellent electron transport ability of the dual EWG concept shows high efficiency and fast mobility, depending on the type of substituents introduced HOMO and LUMO energy levels can be controlled, which can have a wide bandgap and show very good electron transport.
- Formula 1 may be represented by the following Formula 5:
- Ar 1 , L 1 , Z 1 , Z 2 , X 1 and X 5 are as defined in Formula 1,
- n is an integer from 0 to 3
- R 9 is hydrogen, 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, nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, a nuclear atoms of 5 to 60 heteroaryl group, C 1 ⁇ alkyloxy group of C 40 of the, aryloxy of C 6 ⁇ C 60 , C 3 ⁇ 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 boron group, C 6 ⁇ C 60 Aryl phosphine group , C 6 ⁇ C 60 aryl phosphine oxide group and C 6 ⁇ C 60 An arylamine group
- An arylphosphine oxide group and an arylamine group are each independently a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, a nucleus aryloxy atoms, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ⁇ C 40 alkyloxy group, the C 6 ⁇ C 60 of, C 3 ⁇
- L 1 is a C 6 ⁇ C 18 arylene group, preferably characterized in that selected from the group consisting of phenylene group, biphenylene group, terphenyl group and naphthylene group, More preferably, the compound may be selected from the group consisting of compounds represented by the following formulas L-1 to L-11, but is not limited thereto.
- Ar 1 may be a substituent selected from the group consisting of substituents of the following Chemical Formulas 6 to 8:
- P is an integer from 0 to 2
- q is an integer from 0 to 4,
- R 10 to R 12 are the same or different, each independently represent hydrogen, deuterium, C 1 ⁇ alkyl group of C 40, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 of Is selected from the group consisting of a cycloalkyl group, a heterocycloalkyl group of 3 to 40 nuclear atoms, an aryl group of C 6 to C 60 and a heteroaryl group of 5 to 60 nuclear atoms, and combines with an adjacent group to form a condensed ring.
- C 1 ⁇ alkyl group of C 40 C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group
- C 3 ⁇ C 40 of Is selected from the group consisting of a cycloalkyl group, a heterocycloalkyl group of 3 to 40 nuclear atoms, an aryl group of C 6 to C 60 and a heteroaryl group of 5 to 60 nuclear atoms
- the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group and heteroaryl group are each independently C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alky group, C 3 ⁇ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 hetero cycloalkyl, heteroaryl of C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 aryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ aryloxy C 60, C 3 ⁇ C 40 alkyl silyl group, an aryl boronic of C 6 ⁇ C aryl silyl group of 60, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C 60 group, C 6 ⁇ C 60 of the aryl phosphine group, C 6 ⁇ C 60 ary
- the compound represented by Formula 1 of the present invention may be more specifically selected from the group consisting of the following compounds, but is not limited thereto.
- organic electroluminescent device comprising the compound represented by the formula (1) according to the present invention.
- 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.
- a compound represented by the formula (1) includes a compound represented by the 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 be any one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer may include a compound represented by Formula 1 have.
- the organic material layer including the compound of Formula 1 is preferably an electron transport layer or an electron transport auxiliary layer.
- the structure of the organic EL device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
- the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport layer and the electron injection layer may include a compound represented by the formula (1), preferably a hole transport layer, electron blocking layer, light emission
- the auxiliary layer may include a compound represented by Chemical Formula 1. Meanwhile, an electron injection layer may be further stacked on the electron transport layer.
- the organic electroluminescent device of the present invention may have a structure in which an insulating layer or an adhesive layer is inserted between an electrode and an organic material layer interface.
- the organic electroluminescent device of the present invention can be manufactured by forming an organic material layer and an electrode by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1.
- 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.
- the substrate used in the manufacture of the organic EL device of the present invention is not particularly limited, but silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
- 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), 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), 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
- the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
- the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and conventional materials known in the art may be used.
- Ar and Ar ' are an aryl group or a heteroaryl group.
- Example 2 Prepared in Example 1, the reaction of 2-bromo-5,7-dichloro-a - [1,2,4] triazolo [1,5-a] 2,4- di ([1,1 pyrimidine and Preparation Example 2 '-Biphenyl] -4-yl) -6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3 9.5 g (yield 62%) of the title compound was obtained in the same manner as in [Synthesis Example 1], except that, 5-triazine was used.
- Example 1 Prepared in Example 1, the reaction of 2-bromo-5,7-dichloro-a - [1,2,4] triazolo 2,4-a [1,5-a] pyrimidine as Preparation Example 4 (naphthalen-2 I) -6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine Except for the same procedure as in Synthesis Example 1, 8.3 g (yield 55%) of the title compound was obtained.
- Example 1 Prepared in Example 1, the reaction of 2-bromo-5,7-dichloro-a - [1,2,4] triazolo 2,4-a [1,5-a] pyrimidine prepared as in Example 13 (naphthalene-2 Yl) -6- (4 '-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -4- 5.0 g (yield 42%) of the title compound was obtained in the same manner as the [Synthesis Example 1], except that Il) -1,3,5-triazine was used.
- Example 15 Prepared in Example 1, the reaction of 2-bromo-5,7-dichloro-a - [1,2,4] triazolo 2,4-a [1,5-a] pyrimidine and Preparation Example 15 (naphthalene-2 [Synthesis example 1], except that the one) -6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyrimidine was used. ], The same process as in the following to obtain the target compound 6.5 g (yield 58%).
- Step 1 4-([1,1'- Biphenyl ] -4-yl) -6- (4'- Chloro -[1,1'- Biphenyl ] -4-yl) -2-phenylpyrimidine
- Step 2> 4-([1,1'- Biphenyl ] -4-yl) -2-phenyl-6- (4 '-(4,4,5,5- Tetramethyl Synthesis of -1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl] -4-yl) pyrimidine
- Example 1 Prepared in Example 1, the reaction of 2-bromo-5,7-dichloro-a - [1,2,4] triazolo [1,5-a] 1- phenyl-2-pyrimidine prepared as in Example 10 (4- ( 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1H-phenanthro [9,10-d] imidazole, except that Synthesis Example 1] was carried out to obtain 13.2 g (yield 88%) of the title compound.
- Example 3 reaction of 2- (4-chlorophenyl) - [1,2,4] triazolo [1,5-a] 1- phenyl-2-pyrimidine prepared as in Example 10 (4- (4, [Synthesis example] except that 4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1H-phenanthro [9,10-d] imidazole was used. 2] was carried out to obtain 6.4 g (yield 45%) of the title compound.
- a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 mm 3 was washed with distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and then transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.
- ITO Indium tin oxide
- DS-205 Doosan Electronics, 80 nm
- NPB 15 nm
- DS-405 Doosan Electronics, 30nm
- a blue organic electroluminescent device was manufactured in the same manner as in Example 1, except that Alq 3 was used instead of the compound 2 as the electron transporting layer material.
- a blue organic EL device was manufactured in the same manner as in Example 1, except that Compound 2 was not used as the electron transporting material.
- Example 1 Compound 2 4.2 456 8.2 Example 2 Compound 11 4.0 452 8.8 Example 3 Compound 24 4.1 450 9.2 Example 4 Compound 29 3.7 452 6.8 Example 5 Compound 39 3.9 455 8.5 Example 6 Compound 54 3.3 452 7.2 Example 7 Compound 60 3.6 455 9.2 Example 8 Compound 61 3.9 455 8.6 Example 9 Compound 77 4.2 452 8.5 Example 10 Compound 97 3.5 455 9.0 Comparative Example 1 Alq 3 4.7 458 6.0 Comparative Example 2 - 4.8 460 6.2
- the blue organic electroluminescent devices (Examples 1 to 10) using the compound of the present invention in the electron transporting layer were prepared using a blue organic electroluminescent device (comparative example 1) using Alq 3 as the electron transporting layer. Compared with the blue organic electroluminescent device (Comparative Example 2) without an electron transporting layer, it was found to exhibit excellent performance in terms of driving voltage, light emission peak, and current efficiency.
- a glass substrate coated with ITO Indium tin oxide
- ITO Indium tin oxide
- a solvent such as isopropyl alcohol, acetone, methanol
- UV ozone cleaner Power sonic 405, Hwasin Tech
- DS-205 Doosan Electronics, 80 nm
- NPB 15 nm
- DS-405 Doosan Electronics, 30nm
- Compound 2, 10, 27, 28 , 42, 65, 77, 102 5 nm
- Alq 3 25 nm
- a blue organic electroluminescent device was manufactured in the same manner as in Example 11, except that Compound 2 was not used as an electron transport auxiliary layer material, and Alq 3 , which was an electron transport layer material, was deposited at 30 nm instead of 25 nm. .
- Example 11 Compound 2 4.2 456 7.5
- Example 12 Compound 10 3.9 450 8.5
- Example 13 Compound 27 3.6 452 8.9
- Example 14 Compound 28 3.8 455 8.2
- Example 15 Compound 42 3.6 458 7.8
- Example 16 Compound 65 3.9 458 8.6
- Example 17 Compound 77 4.0 450 8.9
- Example 18 Compound 102 4.2 452 8.5 Comparative Example 3 - 4.8 458 6.0
- the blue organic EL device (Examples 11 to 18) using the compound of the present invention in the electron transport auxiliary layer was compared to the blue organic EL device (Comparative Example 3) without the electron transport auxiliary layer. It was found to exhibit excellent performance in terms of current efficiency, light emission peak, and driving voltage.
- the present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, a compound having excellent electron transport ability and an organic light emitting device having improved characteristics such as luminous efficiency, driving voltage, and lifetime by including the same in at least one organic material layer. It relates to an electroluminescent element.
Abstract
Description
샘플 | 전자 수송층 | 구동전압(V) | 발광피크(nm) | 전류효율(cd/A) |
실시예 1 | 화합물 2 | 4.2 | 456 | 8.2 |
실시예 2 | 화합물 11 | 4.0 | 452 | 8.8 |
실시예 3 | 화합물 24 | 4.1 | 450 | 9.2 |
실시예 4 | 화합물 29 | 3.7 | 452 | 6.8 |
실시예 5 | 화합물 39 | 3.9 | 455 | 8.5 |
실시예 6 | 화합물 54 | 3.3 | 452 | 7.2 |
실시예 7 | 화합물 60 | 3.6 | 455 | 9.2 |
실시예 8 | 화합물 61 | 3.9 | 455 | 8.6 |
실시예 9 | 화합물 77 | 4.2 | 452 | 8.5 |
실시예 10 | 화합물 97 | 3.5 | 455 | 9.0 |
비교예 1 | Alq3 | 4.7 | 458 | 6.0 |
비교예 2 | - | 4.8 | 460 | 6.2 |
샘플 | 전자수송 보조층 | 구동 전압(V) | 발광 피크(nm) | 전류효율(cd/A) |
실시예 11 | 화합물 2 | 4.2 | 456 | 7.5 |
실시예 12 | 화합물 10 | 3.9 | 450 | 8.5 |
실시예 13 | 화합물 27 | 3.6 | 452 | 8.9 |
실시예 14 | 화합물 28 | 3.8 | 455 | 8.2 |
실시예 15 | 화합물 42 | 3.6 | 458 | 7.8 |
실시예 16 | 화합물 65 | 3.9 | 458 | 8.6 |
실시예 17 | 화합물 77 | 4.0 | 450 | 8.9 |
실시예 18 | 화합물 102 | 4.2 | 452 | 8.5 |
비교예 3 | - | 4.8 | 458 | 6.0 |
Claims (11)
- 하기 화학식 1로 표시되는 화합물:[화학식 1][화학식 2][화학식 3][화학식 4]여기서,Z1 및 Z-2는 서로 동일하거나 상이하며, 각각 독립적으로 N 또는 C(R2)이며,X1 내지 X5는 서로 동일하거나 상이하며, 각각 독립적으로 N 또는 C(R3)이며,L1은 결합, C6~C18의 아릴렌기 또는 핵원자수 5 내지 18의 헤테로아릴렌기이며,*는 결합이 이루어지는 부분을 의미하고;Ar1은 상기 화학식 2 또는 3의 치환기이며,Y1과 Y2, Y2와 Y3, Y3과 Y4, Y4와 Y5, Y6과 Y1, Y7과 Y8, Y8과 Y9, Y9와 Y10, Y10과 Y11 및 Y11 및 Y7 중 어느 하나는 상기 화학식 4로 표시되는 고리와 축합되어 축합고리를 형성할 수 있고;m은 0 내지 4의 정수이고,상기 화학식 2 에서 상기 화학식 4로 표시되는 고리와 축합을 형성하지 않는 Y1 내지 Y6은 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 C(R4)이며,Y7 은 N(R5) 또는 C(R6)(R7)이며,상기 화학식 3에서 상기 화학식 4로 표시되는 고리와 축합을 형성하지 않는 Y8내지 Y11은 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 C(R8)이며,R2 및 R3은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 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, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택되며,상기 R1 및 R4 내지 R8은 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군으로부터 선택되며, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고,상기 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기 각각 독립적으로, 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, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택된 1종 이상으로 치환될 수 있으며, 복수개의 치환기로 치환될 경우 이들은 서로 동일하거나 상이하며, 인접하는 기와 결합하여 축합 고리를 형성할 수 있다.
- 제 1항에 있어서,상기 화합물은 하기 화학식 5로 표시되는 화합물:[화학식 5]여기서,Ar1, L1, Z1, Z2, X1 및 X5는 제1항에서 정의한 바와 같으며,n은 0 내지 3의 정수이고,R9는 수소, 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, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택되며,상기 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로, 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, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택된 1종 이상으로 치환될 수 있으며, 복수개의 치환기로 치환될 경우 이들은 서로 동일하거나 상이하다.
- 제 1항에 있어서,상기 L1은 C6~C18의 아릴렌기인 화합물.
- 제 3항에 있어서,상기 L1은 페닐렌기, 바이페닐렌기, 터페닐렌기 및 나프틸렌기로 이루어진 군으로부터 선택되는 화합물.
- 제 1항에 있어서,상기 상기 Ar1은 하기 화학식 6 내지 화학식 8의 치환기로 이루어진 군으로부터 선택되는 화합물:[화학식 6][화학식 7][화학식 8]여기서,*, Y1, Y3, Y5, Y7 및 Y9는 제1항에서 정의한 바와 같으며,P는 0 내지2의 정수이고,q는 0 내지 4의 정수이고,R10 내지 R12는 서로 동일하거나 상이하며, 각각 독립적으로 수소, 중수소, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군으로부터 선택되며, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고,상기 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기 및 헤테로아릴기는 각각 독립적으로, 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, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택된 1종 이상으로 치환될 수 있으며, 복수개의 치환기로 치환될 경우 이들은 서로 동일하거나 상이하다.
- (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서,상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항 따른 화합물을 포함하는 것인 유기 전계 발광 소자:
- 제8항에 있어서,상기 유기물층은 발광층, 발광 보조층, 정공 수송층, 정공 주입층, 전자 수송층, 전자 수송보조층 및 전자 주입층 으로 이루어진 군에서 선택되는 유기 전계 발광 소자.
- 제8항에 있어서,상기 유기물층은 발광층, 정공 수송층, 전자수송층 및 전자 수송보조층으로 이루어진 군에서 선택되는 유기 전계 발광 소자.
- 제8항에 있어서,상기 유기물층은 전자수송층 또는 전자수송보조층인 것을 특징으로 하는 유기 전계 발광 소자.
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KR20120078326A (ko) * | 2010-12-31 | 2012-07-10 | 제일모직주식회사 | 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
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JP6918835B2 (ja) | 2021-08-11 |
KR20170123940A (ko) | 2017-11-09 |
CN109071555A (zh) | 2018-12-21 |
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