WO2016105030A1 - Organic light emitting compound and organic electroluminescent device using same - Google Patents
Organic light emitting compound and organic electroluminescent device using same Download PDFInfo
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- WO2016105030A1 WO2016105030A1 PCT/KR2015/013912 KR2015013912W WO2016105030A1 WO 2016105030 A1 WO2016105030 A1 WO 2016105030A1 KR 2015013912 W KR2015013912 W KR 2015013912W WO 2016105030 A1 WO2016105030 A1 WO 2016105030A1
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- Prior art keywords
- group
- aryl
- alkyl
- boron
- formula
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 99
- 239000012044 organic layer Substances 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims description 104
- 239000010410 layer Substances 0.000 claims description 91
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- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 29
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- 238000000034 method Methods 0.000 claims description 28
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- 125000005104 aryl silyl group Chemical group 0.000 claims description 24
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- 125000005264 aryl amine group Chemical group 0.000 claims description 23
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- DJTMCBVPQLCDRW-UHFFFAOYSA-N 2-benzo[a]oxanthren-5-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound C1=CC=CC=2C(=CC3=C(OC4=C(O3)C=CC=C4)C1=2)B1OC(C(O1)(C)C)(C)C DJTMCBVPQLCDRW-UHFFFAOYSA-N 0.000 description 2
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- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Definitions
- the present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, a novel compound having excellent hole injection and transporting ability, light emitting ability, and the like, and the light emitting efficiency and driving voltage by including the same in at least one organic material layer.
- the present invention relates to an organic electroluminescent device having improved characteristics, such as lifespan.
- 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 hole injection, transporting ability, light emitting ability, and the like.
- 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 provides a compound represented by the following formula (1).
- X 1 is selected from the group consisting of O, S, and N (Ar 1 );
- X 2 and X 3 are the same as or different from each other, and each independently selected from the group consisting of O, S, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ) Obviously;
- Y 1 to Y 12 are the same or different from each other, and each independently selected from N or C (R 1), wherein C (R 1) when the plurality clear up a plurality of the C (R 1) are the same or different from each other ,
- R 1 is the same or different, and each independently 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, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ⁇ alkyloxy group of C 40, C 6 to C 60 aryloxy group, C 1 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 1 ⁇ C 60 of the phosphine group, C 1 ⁇ C 60 phosphine oxide group, and a C 1 ⁇ or selected from the group consisting of C
- Ar 1 to Ar 5 are the same as or different from each other, and 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 , Heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group having 6 to C 60 atoms, heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group having 1 to C 40 atoms, aryl jade having 6 to C 60 atoms group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C aryl silyl group of 60, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C group 60 arylboronic of, C 6 ⁇ aryl phosphine of C 60 It is selected from the group consisting of a pin group, a C 6 ⁇ C 60 aryl phosphine oxide group and a C 6 ⁇
- an 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, an aryl boron group, a phosphine group, a phosphine oxide groups and amine groups each independently, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C of 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ⁇ alkyloxy group of C 40, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ alkyloxy group of C 40, C
- 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 represented by Formula 1 may be used as a phosphorescent host of the light emitting layer.
- one or more organic material layers including the compound represented by Chemical Formula 1 may be selected from the group consisting of a light emitting layer, a light emitting auxiliary layer, a hole transport layer, and an electron transport layer.
- the compound represented by Formula 1 of the present invention may be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and luminescence properties.
- an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency, and long life compared to a conventional host material can be manufactured.
- Full color display panels with improved performance and lifetime can also be manufactured.
- the compound of the present invention is characterized in that represented by the formula (1). Since the compound represented by Chemical Formula 1 has a higher molecular weight than the conventional organic EL device material [for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')], the glass transition temperature is high, and thus the thermal stability is excellent. In addition, the carrier transporting ability, the light emitting ability and the like are excellent.
- the conventional organic EL device material for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')
- 'CBP' 4,4-dicarbazolybiphenyl
- the triplet energy gap of the host material should generally be higher than the triplet energy gap of the dopant. That is, when the lowest excited state of the host is higher in energy than the lowest emitted state of the dopant, phosphorescence efficiency may be improved.
- the compound represented by the formula (1) of the present invention can be usefully used as a phosphorescent host material by being able to control the energy level higher than the dopant by introducing a specific substituent into the basic skeleton having a triplet energy.
- the compound of Formula 1 may adjust HOMO and LUMO energy levels according to the type of substituents introduced into the basic skeleton, may have a wide bandgap, it may have a high carrier transport.
- the compound is a bipolar whole molecule when the electron backing group (EWG) having a high electron absorption such as a nitrogen-containing heterocyclic ring (eg, pyridine group, pyrimidine group, triazine group, etc.) is bonded to the basic skeleton. Because of the (bipolar) characteristics, the bonding force between the holes and the electrons can be enhanced.
- EWG electron backing group having a high electron absorption
- a nitrogen-containing heterocyclic ring eg, pyridine group, pyrimidine group, triazine group, etc.
- the compound of Formula 1 having EWG introduced into the basic skeleton has excellent carrier transport properties and luminescent properties, and thus, as an electron injection / transport layer material or a life improvement layer material, in addition to the light emitting layer material of the organic EL device. Can be used.
- the hole injection and transport is smooth.
- EDG electron donor group having a large electron donor such as an arylamine group, carbazole group, terphenyl group, triphenylene group, etc.
- the hole injection and transport is smooth.
- it can be usefully used as a hole injection / transport layer or a light emitting auxiliary layer material.
- Organic material layer material of the organic electroluminescent device preferably the light emitting layer material (blue, green and / or red phosphorescent host material), the electron transporting / injection layer material and the hole transporting / injection layer material, the light emitting auxiliary layer material, It is preferably used as the life improvement layer material. More preferably, it is used as a light emitting layer material, an electron injection layer material, a light emitting auxiliary layer material, and a life improvement layer material.
- the compound of Formula 1 may be a variety of substituents, especially aryl groups and / or heteroaryl groups, etc. are introduced into the basic skeleton to significantly increase the molecular weight of the compound, thereby improving the glass transition temperature, thereby It may have a higher thermal stability than the luminescent material (eg CBP).
- the compound represented by the formula (1) is effective in suppressing the crystallization of the organic material layer. Therefore, the organic electroluminescent device including the compound of Formula 1 according to the present invention can greatly improve the performance, such as driving voltage, efficiency, and life characteristics of the device, the full-color organic light emitting panel to which such an organic electroluminescent device is applied Performance can also be maximized.
- X 1 is selected from the group consisting of O, S, and N (Ar 1 ). More specifically, X 1 is preferably N (Ar 1 ).
- X 2 and X 3 are the same as or different from each other, and each independently from the group consisting of O, S, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ) Is selected.
- X 2 and X 3 may have various forms as shown in Table 1 below, but is not particularly limited thereto.
- X 2 and X 3 are each independently selected from the group consisting of O, S, and N (Ar 1 ).
- Y 1 to Y 12 are the same as or different from each other, and each independently selected from N or C (R 1 ), wherein when there are a plurality of C (R 1 ), a plurality of R 1 is the same or different from each other.
- Y 1 to Y 12 are C (R 1 ), or one of Y 1 to Y 12 is N.
- a plurality of R 1 are each independently 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, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ⁇ alkyloxy group of C 40, C 6 Aryloxy group of ⁇ C 60 , 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 1 ⁇ C 60 phosphine group, C 1 ⁇ C 60 phosphine oxide group, and a C 1 ⁇ selected from the group consist
- each R 1 is independently selected from the group consisting of hydrogen, C 1 ⁇ C 40 Alkyl group, C 6 ⁇ C 60 Aryl group, and a heteroaryl group of 5 to 60 nuclear atoms.
- Ar 1 to Ar 5 are the same as or different from each other, and each independently C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 3 ⁇ C 40 cyclo Alkyl 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 , aryl of C 6 to C 60 Oxy 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 groups, C 6 -C 60 arylphosphine oxide groups and C 6 -C 60 arylamine groups.
- Ar 1 to Ar 5 are the same as or different from each other, and each independently C 6 ⁇ C 60
- the aryl group, or a heteroaryl group having 5 to 60 nuclear atoms may be selected from phenyl group, biphenyl group, naphthyl group, phenanthrene group, pyrene group, triphenylene group, fluorene group and the like, the heteroaryl having 5 to 60 nuclear atoms
- the group may be selected from pyridine, pyrimidine, triazine, quinazoline, carbazole, dibenzofuran, dibenzothiophene and the like.
- Cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, phosphine group, phosphine oxide group and amine 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, 3 to 40 heterocycloalkyl group, C 6 Aryl group of ⁇ C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 ⁇ C 40 , aryloxy group of C 6 ⁇ C 60 , alkylsilyl group of C 1 ⁇ C 40 , C 6 ⁇
- the compound represented by the formula (1) according to the present invention may be more specifically specified by any one of the following C-1 to C-15.
- the phosphorescent host can balance electrons and electrons in the light emitting layer to improve electron mobility and maximize efficiency characteristics with a thermally stable structure. There is an advantage as a material.
- At least one of R 1 and Ar 1 to Ar 5 may be a substituent represented by the following formula (2).
- L is a single bond, or is C 6 ⁇ C 18 aryl group and a nuclear atoms selected from the group consisting of a hetero arylene of 5 to 18; Preferably it may be a single bond or a phenylene group or a biphenylene group.
- Z 1 to Z 5 are the same as or different from each other, and each independently N or C (R 11 ), provided that at least one of Z 1 to Z 5 is N, wherein at least two of Z 1 to Z 5 is C (R) 11 ), a plurality of R 11 's are the same or different from each other even if they are the same;
- R 11 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 6 -C 40 aryl group, of nuclear atoms of 5 to 40 heteroaryl group, C 6 ⁇ C 40 of the aryloxy group, C 1 ⁇ C 40 alkyloxy group of, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group of , C 6 ⁇ C 40 arylamine group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 40 aryl boron group, C 6 ⁇ C 40 aryl phosphine group A C 6 to C 40 arylphosphine oxide group and a C 6 to C 40 arylsilyl group, or condensed in combination with an
- Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenes group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ⁇ C 40, alkyloxy group of C 1 ⁇ C 40 of the , C 6 -C 40
- the substituent represented by the formula (2) may be more specific with any one of the substituents represented by the following A-1 to A-15. However, this is not particularly limited.
- n is an integer of 0 to 4, wherein when n is 0, all means hydrogen. When n is 1 to 4, it means that a part of hydrogen is substituted with a substituent R 12 . When n is an integer of 1 to 4, hydrogen is substituted with R 12 , wherein when there are a plurality of R 12 , they are the same as or different from each other,
- R 12 is 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 , nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 40 aryl group, nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 aryl amine group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 group of an alkyl boron, C 6 ⁇ C 40 group of the arylboronic, C 6 ⁇ C 40 aryl phosphine Fin group, C 6 ⁇ C 40 aryl phosphine oxide group and C 6 ⁇ C 40 It may be selected from the group consisting of aryl
- Alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 to C 40 alkynyl group, C 6 to C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 to C 40 aryloxy group, C 1 to C 40 Alkyloxy group, C 6 -C 40
- At least one of R 1 and Ar 1 to Ar 5 may be a substituent represented by Formula 2, and more preferably, Ar 1 is a substituent represented by Formula 2. .
- At least one of R 1 and Ar 1 to Ar 5 may be a substituent represented by the following formula (3).
- L 2 is a single bond, or is C 6 ⁇ C can be an aryl group and a nucleus of atoms of 18 is selected from the group consisting of a hetero arylene of 5 to 18, preferably or a single bond may be a phenylene group or biphenylene.
- R 13 and R 14 are the same as or different from each other, and each independently represent an alkyl group of C 1 to C 40 , an aryl group of C 6 to C 40 , a heteroaryl group of 5 to 40 nuclear atoms, and a C 6 to C 60 group ; Or an arylamine group, or R 13 and R 14 may combine to form a condensed ring;
- an alkyl group, an aryl group, a heteroaryl group and an arylamine group 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 6 ⁇ C 40 aryl group, heteroaryl group of 5 to 40 nuclear atoms, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 Arylamine group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 1 ⁇ C 40 Alkylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 40 the arylboronic group, C 6 ⁇ C 40 aryl phosphine group, C 6 ⁇ C 40 aryl phosphine oxide group, and a
- At least one of R 1 and Ar 1 to Ar 5 may be a substituent represented by Chemical Formula 3, and more preferably, Ar 1 is a substituent represented by Chemical Formula 3. .
- the compound of the present invention described above may be further embodied as a compound represented by any one of Formulas 1 to 101 illustrated below.
- the compound represented by the formula (1) of the present invention is not limited by those illustrated below.
- 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 compound represented by Chemical Formula 1 may be synthesized according to a general synthetic method, and for example, a core may be synthesized according to Scheme I below. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
- 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 a hole transport layer, an electron transport layer, a light emitting layer, or a light emitting auxiliary layer.
- the light emitting layer of the organic electroluminescent device of the present invention may include a host material, and may include the compound of Formula 1 as the host material.
- 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, an electron transport layer, a light emitting layer
- the light emitting auxiliary layer may include a compound represented by Chemical Formula 1.
- 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.
- a glass substrate coated with ITO Indium tin oxide having a thickness of 1500 ⁇ was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
- ITO Indium tin oxide
- UV OZONE cleaner Power sonic 405, Hwasin Tech
- a green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound synthesized in Synthesis Example as a light emitting host material when forming the emission layer.
- Example 1 One 7.20 525 36.4
- Example 2 4 6.82 518 39.9
- Example 3 5 6.98 517 40.2
- Example 4 6 6.89 515 38.4
- Example 5 7 6.78 518 42.4
- Example 6 10 6.69 518 42.8
- Example 7 11 6.72 517 41.7
- Example 8 16 6.70 515 42.0
- Example 9 17 6.82 518 40.3
- Example 10 18 6.84 518 41.2 Comparative Example 1 CBP 6.93 516 38.2
- the green organic EL device of Examples 1 to 10 using the compounds (1, 4 to 7, 10 to 11, 16 to 18) according to the present invention as a light emitting layer is compared using a conventional CBP. Compared with the green organic EL device of Example 1, it can be seen that it shows better performance in terms of efficiency and driving voltage.
- the compound synthesized in the synthesis example was subjected to high purity sublimation purification by a commonly known method, and then a red organic EL device was manufactured according to the following procedure.
- a glass substrate coated with ITO Indium tin oxide having a thickness of 1500 ⁇ was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
- ITO Indium tin oxide
- UV OZONE cleaner Power sonic 405, Hwasin Tech
- M-MTDATA 60 nm) / TCTA (80 nm) / Compound (1, 5, 8-9, 15-20) + 10% (piq) 2 Ir (acac) (30nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) were laminated in order to fabricate an organic EL device.
- a red organic electroluminescent device was manufactured in the same manner as in Example 11, except that CBP was used instead of the compound of Synthesis Example 1 as a light emitting host material when forming the emission layer.
- Example 11 One 5.30 8.92 Example 12 5 5.12 10.5 Example 13 8 4.92 10.4 Example 14 9 4.87 9.4 Example 15 15 4.90 9.8 Example 16 16 4.77 11.5 Example 17 17.72 10.2 Example 18 18 4.80 11.0 Example 19 19 4.59 12.8 Example 20 20 4.65 12.0 Comparative Example 2 CBP 5.25 8.2
- the red organic electroluminescent device of Examples 11 to 20, which uses the compounds (1, 5, 8-9, 15-20) according to the present invention as a material of the light emitting layer has conventional CBP
- the red organic electroluminescent element of the comparative example 2 used as a material it turns out that it shows the outstanding performance in efficiency and a drive voltage.
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Abstract
The present invention relates to an organic electroluminescent device comprising a novel compound having excellent light emitting capability and at least one organic layer containing the compound, thereby improving characteristics such as light emitting efficiency, driving voltage, and life of the organic electroluminescent device.
Description
본 발명은 신규한 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로, 보다 상세하게는 정공 주입 및 수송능, 발광능 등이 우수한 신규한 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 light emitting compound and an organic electroluminescent device using the same, and more particularly, a novel compound having excellent hole injection and transporting ability, light emitting ability, and the like, and the light emitting efficiency and driving voltage by including the same in at least one organic material layer. The present invention relates to an organic electroluminescent device having improved characteristics, such as lifespan.
1950년대 Bernanose의 유기 박막 발광 관측을 시점으로 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광 (electroluminescent, EL) 소자(이하, 간단히 '유기 EL 소자'로 칭함)에 대한 연구는 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 EL 소자가 제시되었다. 이후 고효율, 고수명의 유기 EL 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물 층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다. The study of organic electroluminescent (EL) devices (hereinafter simply referred to as 'organic EL devices') led to the blue electroluminescence using anthracene single crystals in 1965, based on Bernanose's observation of organic thin film emission. By (Tang), an organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer has been proposed. Since then, in order to make high-efficiency, high-life organic EL devices, the development has been made in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어 주면 양극에서는 정공이 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, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다. In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from the anode, and electrons are injected into the organic material layer from the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. 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 its function.
유기 EL 소자의 발광층 형성재료는 발광색에 따라 청색, 녹색, 적색 발광 재료로 구분될 수 있다. 그밖에, 보다 나은 천연색을 구현하기 위한 발광재료로 노란색 및 주황색 발광재료도 사용된다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 재료로서 호스트/도펀트 계를 사용할 수 있다. 도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 이러한 인광 재료의 개발은 이론적으로 형광에 비해 4배까지의 발광 효율을 향상시킬 수 있어 인광 도판트 뿐만 아니라 인광 호스트 재료들에 대해 관심이 집중되고 있다. 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. In addition, 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.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층으로는, 하기 화학식으로 표현된 NPB, BCP, Alq3 등이 널리 알려져 있고, 발광 재료는 안트라센 유도체들이 형광 도판트/호스트 재료로서 보고되고 있다. 특히 발광재료 중 효율 향상 측면에서 큰 장점을 가지고 있는 인광 재료로서는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색, 녹색, 적색 도판트 재료로 사용되고 있다. 현재까지는 CBP가 인광 호스트 재료로 우수한 특성을 나타내고 있다. Hole injection layer, hole transport layer to date. As the hole blocking layer and the electron transporting layer, NPB, BCP, Alq 3 and the like represented by the following formulas are widely known, and anthracene derivatives have been reported as fluorescent dopant / host materials in the light emitting material. Particularly, 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. To date, CBP has shown excellent properties as a phosphorescent host material.
그러나 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮고 열적 안정성이 매우 좋지 않아 유기 EL 소자에서의 수명 측면에서 만족할만한 수준이 되지 못하고 있다. However, existing materials have advantages in terms of luminescence properties, but the glass transition temperature is low and the thermal stability is very poor, and thus the materials are not satisfactory in terms of lifespan in organic EL devices.
본 발명은 유기 전계 발광 소자에 적용할 수 있으며, 정공 주입 및 수송능, 발광능 등이 모두 우수한 신규 유기 화합물을 제공하는 것을 목적으로 한다. 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 hole injection, transporting ability, light emitting ability, and the like.
또한 본 발명은 상기 신규 유기 화합물을 포함하여 낮은 구동전압과 높은 발광효율을 나타내며 수명이 향상되는 유기 전계 발광 소자를 제공하는 것을 또 다른 목적으로 한다.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.
상기 목적을 달성하기 위하여, 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 Chemical Formula 1,
X1은 O, S, 및 N(Ar1)로 이루어진 군에서 선택되고;X 1 is selected from the group consisting of O, S, and N (Ar 1 );
X2 및 X3는 서로 동일하거나 또는 상이하며, 각각 독립적으로 O, S, N(Ar1), C(Ar2)(Ar3) 및 Si(Ar4)(Ar5)로 구성된 군으로부터 선택되고;X 2 and X 3 are the same as or different from each other, and each independently selected from the group consisting of O, S, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ) Become;
Y1 내지 Y12은 서로 동일하거나 또는 상이하며, 각각 독립적으로 N 또는 C(R1)에서 선택되고, 이때 C(R1)이 복수 개일 경우 복수의 C(R1)은 서로 동일하거나 또는 상이하며, Y 1 to Y 12 are the same or different from each other, and each independently selected from N or C (R 1), wherein C (R 1) when the plurality clear up a plurality of the C (R 1) are the same or different from each other ,
R1은 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, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C1~C60의 포스핀기, C1~C60의 포스핀옥사이드기 및 C1~C60의 아민기로 이루어진 군에서 선택되거나, 또는 인접한 기와 결합하여 축합 고리를 형성할 수 있고,R 1 is the same or different, and each independently 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, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ alkyloxy group of C 40, C 6 to C 60 aryloxy group, C 1 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 1 ~ C 60 of the phosphine group, C 1 ~ C 60 phosphine oxide group, and a C 1 ~ or selected from the group consisting of C 60 amines, or to the adjacent group bonded may form a condensed ring,
Ar1 내지 Ar5는 서로 동일하거나 또는 상이하며, 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, 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,Ar 1 to Ar 5 are the same as or different from each other, and 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 , Heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group having 6 to C 60 atoms, heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group having 1 to C 40 atoms, aryl jade having 6 to C 60 atoms group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C aryl silyl group of 60, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ aryl phosphine of C 60 It is selected from the group consisting of a pin group, a C 6 ~ C 60 aryl phosphine oxide group and a C 6 ~ C 60 arylamine group,
상기 R1 및 Ar1 내지 Ar5에서 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 포스핀기, 포스핀옥사이드기 및 아민기는 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, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C1~C60의 포스핀기, C1~C60의 포스핀옥사이드기 및 C1~C60의 아민기로 이루어진 군에서 선택된 1종 이상으로 치환 또는 비치환될 수 있다. 이때 R1 및 Ar1 내지 Ar5가 복수 개의 치환기로 치환될 경우, 복수 개의 치환기는 서로 동일하거나 상이할 수 있다.In R 1 and Ar 1 to Ar 5 , an 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, an aryl boron group, a phosphine group, a phosphine oxide groups and amine groups, each independently, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C of 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ~ alkyloxy group of C 40, 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 1 ~ C 60 phosphine group, may be unsubstituted or substituted with one or more selected from the group consisting of C 1 ~ C 60 of the phosphine oxide group, and a group of C 1 ~ C 60 amine. In this case, when R 1 and Ar 1 to Ar 5 is substituted with a plurality of substituents, the plurality of substituents may be the same or different from each other.
또한, 본 발명은 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 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.
여기서, 상기 화학식 1로 표시되는 화합물은 발광층의 인광 호스트로 사용될 수 있다. 또한 상기 화학식 1로 표시되는 화합물을 포함하는 1층 이상의 유기물층은 발광층, 발광보조층, 정공수송층 및 전자수송층으로 이루어진 군에서 선택될 수 있다. Here, the compound represented by Formula 1 may be used as a phosphorescent host of the light emitting layer. In addition, one or more organic material layers including the compound represented by Chemical Formula 1 may be selected from the group consisting of a light emitting layer, a light emitting auxiliary layer, a hole transport layer, and an electron transport layer.
본 발명의 화학식 1로 표시되는 화합물은 열적 안정성 및 발광 특성이 우수하기 때문에 유기 전계 발광 소자의 유기물층의 재료로 사용될 수 있다.The compound represented by Formula 1 of the present invention may be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and luminescence properties.
특히, 본 발명의 화학식 1로 표시되는 화합물을 인광 호스트 재료로 사용할 경우, 종래의 호스트 재료에 비해 우수한 발광 성능, 낮은 구동전압, 높은 효율 및 장수명을 갖는 유기 전계 발광 소자를 제조할 수 있고, 나아가 성능 및 수명이 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency, and long life compared to a conventional host material can be manufactured. Full color display panels with improved performance and lifetime can also be manufactured.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
<신규 유기 화합물><New organic compound>
본 발명의 화합물은 상기 화학식 1로 표시되는 것을 특징으로 한다. 이러한 화학식 1로 표시되는 화합물은 종래 유기 EL 소자용 재료[예: 4,4-dicarbazolybiphenyl (이하, 'CBP'라 함)]보다 높은 분자량을 갖기 때문에, 유리전이온도가 높아 열적 안정성이 우수할 뿐만 아니라, 캐리어 수송능, 발광능 등이 우수하다. The compound of the present invention is characterized in that represented by the formula (1). Since the compound represented by Chemical Formula 1 has a higher molecular weight than the conventional organic EL device material [for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')], the glass transition temperature is high, and thus the thermal stability is excellent. In addition, the carrier transporting ability, the light emitting ability and the like are excellent.
보다 구체적으로, 유기 전계 발광 소자의 인광 발광층에서, 호스트 물질의 삼중항 에너지 갭은 일반적으로 도펀트의 삼중항 에너지 갭보다 높아야 한다. 즉, 호스트의 가장 낮은 여기 상태가 도펀트의 가장 낮은 방출 상태보다 에너지가 더 높은 경우, 인광 발광 효율이 향상될 수 있다. 이에, 본 발명의 화학식 1로 표시되는 화합물은 삼중항 에너지가 높은 기본 골격에 특정의 치환기가 도입됨으로써, 에너지 준위가 도펀트보다 높게 조절될 수 있어 인광 호스트 물질로 유용하게 사용될 수 있다.More specifically, in the phosphorescent layer of the organic EL device, the triplet energy gap of the host material should generally be higher than the triplet energy gap of the dopant. That is, when the lowest excited state of the host is higher in energy than the lowest emitted state of the dopant, phosphorescence efficiency may be improved. Thus, the compound represented by the formula (1) of the present invention can be usefully used as a phosphorescent host material by being able to control the energy level higher than the dopant by introducing a specific substituent into the basic skeleton having a triplet energy.
또한, 상기 화학식 1의 화합물은 상기 기본 골격에 도입되는 치환기의 종류에 따라 HOMO 및 LUMO 에너지 레벨을 조절할 수 있어, 넓은 밴드갭을 가질 수 있고, 높은 캐리어 수송성을 가질 수 있다. 일례로, 상기 화합물은 상기 기본 골격에 질소-함유 헤테로환(예컨대, 피리딘기, 피리미딘기, 트리아진기 등)과 같이 전자 흡수성이 큰 전자 끌개기(EWG)가 결합될 경우, 분자 전체가 바이폴라(bipolar) 특성을 갖기 때문에, 정공과 전자의 결합력을 높일 수 있다. 이와 같이, 상기 기본 골격에 EWG가 도입된 상기 화학식 1의 화합물은 우수한 캐리어 수송성 및 발광 특성이 우수하기 때문에, 유기 전계 발광 소자의 발광층 재료 이외에, 전자주입/수송층 재료, 또는 수명 개선층 재료로도 사용될 수 있다. In addition, the compound of Formula 1 may adjust HOMO and LUMO energy levels according to the type of substituents introduced into the basic skeleton, may have a wide bandgap, it may have a high carrier transport. For example, the compound is a bipolar whole molecule when the electron backing group (EWG) having a high electron absorption such as a nitrogen-containing heterocyclic ring (eg, pyridine group, pyrimidine group, triazine group, etc.) is bonded to the basic skeleton. Because of the (bipolar) characteristics, the bonding force between the holes and the electrons can be enhanced. As such, the compound of Formula 1 having EWG introduced into the basic skeleton has excellent carrier transport properties and luminescent properties, and thus, as an electron injection / transport layer material or a life improvement layer material, in addition to the light emitting layer material of the organic EL device. Can be used.
한편, 상기 화학식 1의 화합물이 상기 기본 골격에 아릴아민기, 카바졸기, 터페닐기, 트리페닐렌기 등과 같이 전자 공여성이 큰 전자 주게기(EDG)가 결합될 경우, 정공의 주입 및 수송이 원활하게 이루어지기 때문에, 발광층 재료 이외에, 정공주입/수송층 또는 발광 보조층 재료로도 유용하게 사용될 수 있다.On the other hand, when the compound of Formula 1 is combined with an electron donor group (EDG) having a large electron donor such as an arylamine group, carbazole group, terphenyl group, triphenylene group, etc., the hole injection and transport is smooth. In addition to the light emitting layer material, it can be usefully used as a hole injection / transport layer or a light emitting auxiliary layer material.
상기와 같이, 본 발명의 화학식 1로 표시되는 화합물은 유기 전계 발광 소자의 발광 특성을 향상시킴과 동시에, 정공 주입/수송 능력, 전자 주입/수송 능력, 발광 효율, 구동 전압, 수명 특성 등을 향상시킬 수 있으므로, 유기 전계 발광 소자의 유기물층 재료, 바람직하게는 발광층 재료(청색, 녹색 및/또는 적색의 인광 호스트 재료), 전자 수송/주입층 재료 및 정공 수송/주입층 재료, 발광보조층 재료, 수명개선층 재료로 사용되는 것이 바람직하다. 더욱 바람직하게는 발광층 재료, 전자 주입층 재료, 발광보조층 재료, 수명 개선층 재료로 사용되는 것이다.As described above, the compound represented by Chemical Formula 1 of the present invention not only improves the light emission characteristics of the organic electroluminescent device, but also improves the hole injection / transport capacity, the electron injection / transport ability, the luminous efficiency, the driving voltage, and the lifetime characteristics. Organic material layer material of the organic electroluminescent device, preferably the light emitting layer material (blue, green and / or red phosphorescent host material), the electron transporting / injection layer material and the hole transporting / injection layer material, the light emitting auxiliary layer material, It is preferably used as the life improvement layer material. More preferably, it is used as a light emitting layer material, an electron injection layer material, a light emitting auxiliary layer material, and a life improvement layer material.
또한, 상기 화학식 1의 화합물은 상기 기본 골격에 다양한 치환체, 특히 아릴기 및/또는 헤테로아릴기 등이 도입되어 화합물의 분자량이 유의적으로 증대됨으로써 유리 전이온도가 향상될 수 있고, 이로 인해 종래의 발광 재료(예를 들어, CBP) 보다 높은 열적 안정성을 가질 수 있다. 아울러, 상기 화학식 1로 표시되는 화합물은 유기물층의 결정화 억제에도 효과가 있다. 따라서, 본 발명에 따른 화학식 1의 화합물을 포함하는 유기 전계 발광 소자는 소자의 구동전압, 효율, 및 수명 특성 등의 성능이 크게 향상될 수 있고, 이러한 유기 전계 발광 소자가 적용된 풀 칼라 유기 발광 패널도 성능이 극대화될 수 있다.In addition, the compound of Formula 1 may be a variety of substituents, especially aryl groups and / or heteroaryl groups, etc. are introduced into the basic skeleton to significantly increase the molecular weight of the compound, thereby improving the glass transition temperature, thereby It may have a higher thermal stability than the luminescent material (eg CBP). In addition, the compound represented by the formula (1) is effective in suppressing the crystallization of the organic material layer. Therefore, the organic electroluminescent device including the compound of Formula 1 according to the present invention can greatly improve the performance, such as driving voltage, efficiency, and life characteristics of the device, the full-color organic light emitting panel to which such an organic electroluminescent device is applied Performance can also be maximized.
본 발명에 따라 화학식 1로 표시되는 화합물에서, X1은 O, S, 및 N(Ar1)로 이루어진 군에서 선택된다. 보다 구체적으로 X1은 N(Ar1)일 때가 바람직하다.In the compound represented by Formula 1 according to the present invention, X 1 is selected from the group consisting of O, S, and N (Ar 1 ). More specifically, X 1 is preferably N (Ar 1 ).
또한 X2 및 X3는 서로 동일하거나 또는 상이하며, 각각 독립적으로 O, S, N(Ar1), C(Ar2)(Ar3) 및 Si(Ar4)(Ar5)로 구성된 군으로부터 선택된다. And X 2 and X 3 are the same as or different from each other, and each independently from the group consisting of O, S, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ) Is selected.
보다 구체적으로, 상기 X2 및 X3는 하기 표 1과 같은 다양한 형태를 가질 수 있으나, 이에 특별히 한정되는 것은 아니다. 바람직하게는 X2 및 X3가 각각 독립적으로 O, S, 및 N(Ar1)으로 이루어진 군에서 선택되는 것이다. More specifically, X 2 and X 3 may have various forms as shown in Table 1 below, but is not particularly limited thereto. Preferably X 2 and X 3 are each independently selected from the group consisting of O, S, and N (Ar 1 ).
| X2 X 2 | X3 X 3 | X2 X 2 | X3 X 3 | X2 X 2 | X3 X 3 |
| OO | OO | N(Ar1)N (Ar 1 ) | OO | SS | OO |
| OO | SS | N(Ar1)N (Ar 1 ) | SS | SS | SS |
| OO | N(Ar1)N (Ar 1 ) | N(Ar1)N (Ar 1 ) | N(Ar1)N (Ar 1 ) | SS | N(Ar1)N (Ar 1 ) |
| OO | C(Ar2)(Ar3)C (Ar 2 ) (Ar 3 ) | N(Ar1)N (Ar 1 ) | C(Ar2)(Ar3)C (Ar 2 ) (Ar 3 ) | SS | C(Ar2)(Ar3)C (Ar 2 ) (Ar 3 ) |
| OO | Si(Ar4)(Ar5)Si (Ar 4 ) (Ar 5 ) | N(Ar1)N (Ar 1 ) | Si(Ar4)(Ar5)Si (Ar 4 ) (Ar 5 ) | SS | Si(Ar4)(Ar5)Si (Ar 4 ) (Ar 5 ) |
또한 Y1 내지 Y12은 서로 동일하거나 또는 상이하며, 각각 독립적으로 N 또는 C(R1)에서 선택되고, 이때 C(R1)이 복수 개일 경우 복수의 R1은 서로 동일하거나 또는 상이하다. In addition, Y 1 to Y 12 are the same as or different from each other, and each independently selected from N or C (R 1 ), wherein when there are a plurality of C (R 1 ), a plurality of R 1 is the same or different from each other.
보다 구체적으로는 Y1 내지 Y12는 모두 C(R1)이거나, 또는 Y1 내지 Y12중 하나가 N인 것이 바람직하다. More specifically, it is preferable that all of Y 1 to Y 12 are C (R 1 ), or one of Y 1 to Y 12 is N.
여기서, 복수 개의 R1은 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, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C1~C60의 포스핀기, C1~C60의 포스핀옥사이드기 및 C1~C60의 아민기로 이루어진 군에서 선택되거나, 또는 상기 R1 이 인접한 기(예, 다른 R1)과 결합하여 축합 고리를 형성할 수 있다. Here, a plurality of R 1 are each independently 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, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ alkyloxy group of C 40, C 6 Aryloxy group of ~ C 60 , 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 1 ~ C 60 phosphine group, C 1 ~ C 60 phosphine oxide group, and a C 1 ~ selected from the group consisting of C 60 amines, or, or a group wherein R 1 is adjacent to the condensation in conjunction with (e. g., different R 1) May form a ring.
본 발명에서, 상기 R1은 각각 독립적으로 수소, C1~C40의 알킬기, C6~C60의 아릴기, 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택되는 것이 바람직하다. In the present invention, each R 1 is independently selected from the group consisting of hydrogen, C 1 ~ C 40 Alkyl group, C 6 ~ C 60 Aryl group, and a heteroaryl group of 5 to 60 nuclear atoms.
또한 Ar1 내지 Ar5는 서로 동일하거나 또는 상이하며, 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, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된다. In addition, Ar 1 to Ar 5 are the same as or different from each other, and each independently C 1 ~ C 40 Alkyl group, C 2 ~ C 40 Alkenyl group, C 2 ~ C 40 Alkynyl group, C 3 ~ C 40 cyclo Alkyl 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 , aryl of C 6 to C 60 Oxy 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 groups, C 6 -C 60 arylphosphine oxide groups and C 6 -C 60 arylamine groups.
보다 구체적으로, 상기 Ar1 내지 Ar5는 서로 동일하거나 또는 상이하며, 각각 독립적으로 C6~C60의 아릴기, 또는 핵원자수 5 내지 60의 헤테로아릴기인 것이 바람직하다. 일례로, 상기 C6~C60의 아릴기는 페닐기, 비페닐기, 나프틸기, 페난트렌기, 파이렌기, 트리페닐렌기, 플루오렌기 등에서 선택될 수 있으며, 상기 핵원자수 5 내지 60의 헤테로아릴기는 피리딘, 피리미딘, 트리아진, 퀴나졸린, 카바졸, 디벤조퓨란, 디벤조싸이오펜 등에서 선택될 수 있다. More specifically, Ar 1 to Ar 5 are the same as or different from each other, and each independently C 6 ~ C 60 It is preferable that the aryl group, or a heteroaryl group having 5 to 60 nuclear atoms. For example, the C 6 ~ C 60 aryl group may be selected from phenyl group, biphenyl group, naphthyl group, phenanthrene group, pyrene group, triphenylene group, fluorene group and the like, the heteroaryl having 5 to 60 nuclear atoms The group may be selected from pyridine, pyrimidine, triazine, quinazoline, carbazole, dibenzofuran, dibenzothiophene and the like.
상기 R1 및 Ar1 내지 Ar5에서, 알킬기, 알케닐기, 알키닐기. 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 포스핀기, 포스핀옥사이드기 및 아민기는 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, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C1~C60의 포스핀기, C1~C60의 포스핀옥사이드기 및 C1~C60의 아민기로 이루어진 군에서 선택된 1종 이상으로 치환 또는 비치환될 수 있다. 이때 상기 치환기가 복수인 경우, 이들의 서로 동일하거나 또는 상이할 수 있다. In R 1 and Ar 1 to Ar 5 , an alkyl group, an alkenyl group, an alkynyl group. Cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron group, aryl boron group, phosphine group, phosphine oxide group and amine 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, 3 to 40 heterocycloalkyl group, C 6 Aryl group of ~ C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 ~ C 40 , aryloxy group of C 6 ~ C 60 , alkylsilyl group of C 1 ~ C 40 , C 6 ~ C 60 aryl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 1 ~ C 60 phosphine group, C 1 ~ Force of C 60 pin oxide groups and C 1 It may be substituted or unsubstituted with one or more selected from the group consisting of -C 60 amine groups. In this case, when there are a plurality of the substituents, these may be the same or different from each other.
본 발명에 따른 화학식 1로 표시되는 화합물은 하기 C-1 내지 C-15 중 어느 하나로 보다 구체화될 수 있다.The compound represented by the formula (1) according to the present invention may be more specifically specified by any one of the following C-1 to C-15.
상기 화학식 C-1 내지 C-15에서, Y1 내지 Y12 및 Ar1 내지 Ar5는 화학식 1에서 정의한 바와 동일하다.In Formulas C-1 to C-15, Y 1 to Y 12 and Ar 1 to Ar 5 are the same as defined in Formula 1.
특히, 본 발명에서 Ar1 위치에 방향족 환 또는 헤테로 방향족 환이 치환기로 도입될 경우, 전자이동성을 향상시켜 발광층에서의 정공과 전자의 균형을 맞추고, 열적 안정한 구조로 효율 특성을 극대화 할 수 있는 인광 호스트 재료로써의 장점이 있다. Particularly, when an aromatic ring or a heteroaromatic ring is introduced as a substituent at the Ar 1 position in the present invention, the phosphorescent host can balance electrons and electrons in the light emitting layer to improve electron mobility and maximize efficiency characteristics with a thermally stable structure. There is an advantage as a material.
본 발명의 바람직한 일례에 따르면, 상기 R1 및 Ar1 내지 Ar5 중 적어도 하나는 하기 화학식 2로 표시되는 치환체일 수 있다.According to a preferred embodiment of the present invention, at least one of R 1 and Ar 1 to Ar 5 may be a substituent represented by the following formula (2).
상기 화학식 2에서,In Chemical Formula 2,
*는 상기 화학식 1에 결합되는 부분을 의미하고;* Means a moiety bonded to Formula 1;
L은 단일결합이거나, 또는 C6~C18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택되고; 바람직하게는 단일결합이거나 페닐렌기 또는 비페닐렌기일 수 있다. L is a single bond, or is C 6 ~ C 18 aryl group and a nuclear atoms selected from the group consisting of a hetero arylene of 5 to 18; Preferably it may be a single bond or a phenylene group or a biphenylene group.
Z1 내지 Z5는 서로 동일하거나 상이하며, 각각 독립적으로 N 또는 C(R11)이며, 다만 Z1 내지 Z5 중 적어도 하나는 N이고, 이때 Z1 내지 Z5 중 2 이상이 C(R11)인 경우, 복수 개의 R11은 동일하게 표기되더라도 서로 동일하거나 상이하며;Z 1 to Z 5 are the same as or different from each other, and each independently N or C (R 11 ), provided that at least one of Z 1 to Z 5 is N, wherein at least two of Z 1 to Z 5 is C (R) 11 ), a plurality of R 11 's are the same or different from each other even if they are the same;
R11은 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C40의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되거나, 또는 인접하는 기(예컨대, L, 및/또는 인접하는 다른 R11)와 결합하여 축합 고리를 형성할 수 있으며,R 11 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 6 -C 40 aryl group, of nuclear atoms of 5 to 40 heteroaryl group, C 6 ~ C 40 of the aryloxy group, C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group of , C 6 ~ C 40 arylamine group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group A C 6 to C 40 arylphosphine oxide group and a C 6 to C 40 arylsilyl group, or condensed in combination with an adjacent group (eg, L, and / or another adjacent R 11 ). Can form a ring,
상기 L 및 R11에서 아릴렌기, 헤테로아릴렌기, 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환될 수 있다. 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다. Arylene group, heteroarylene group, alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group in L and R 11 , Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenes group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ~ C 40, alkyloxy group of C 1 ~ C 40 of the , C 6 -C 40 arylamine group, C 3 -C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group , C 6 ~ C 40 aryl group of boron, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ from the group consisting of C 40 arylsilyl of It may be unsubstituted or substituted with one or more substituents selected. In this case, when there are a plurality of substituents, they may be the same or different from each other.
본 발명에 따라, 상기 화학식 2로 표시되는 치환체는 하기 A-1 내지 A-15로 표시되는 치환체 중 어느 하나로 보다 구체화될 수 있다. 그러나 이에 특별히 한정되지 않는다. According to the present invention, the substituent represented by the formula (2) may be more specific with any one of the substituents represented by the following A-1 to A-15. However, this is not particularly limited.
상기 A-1 내지 A-15에서,In the above A-1 to A-15,
L 및 R11은 상기 화학식 2에서 정의된 바와 같고, L and R 11 are the same as defined in Formula 2,
n은 0 내지 4의 정수이며, 이때 n이 0인 경우 모두 수소인 것을 의미하며, 상기 n이 1 내지 4인 경우, 수소의 일부가 치환기 R12로 치환된 것을 의미한다. 상기 n이 1 내지 4의 정수인 경우 수소가 R12로 치환되되, 이때 R12가 복수 개인 경우, 이들은 서로 동일하거나 또는 상이하며, n is an integer of 0 to 4, wherein when n is 0, all means hydrogen. When n is 1 to 4, it means that a part of hydrogen is substituted with a substituent R 12 . When n is an integer of 1 to 4, hydrogen is substituted with R 12 , wherein when there are a plurality of R 12 , they are the same as or different from each other,
R12는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며, 이때 R12가 복수인 경우, 이들은 서로 동일하거나 또는 상이하며;R 12 is 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 , nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 40 aryl group, nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 aryl amine group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group of the arylboronic, C 6 ~ C 40 aryl phosphine Fin group, C 6 ~ C 40 aryl phosphine oxide group and C 6 ~ C 40 It may be selected from the group consisting of arylsilyl group, or by combining with an adjacent group to form a condensed ring, wherein when R 12 is a plurality , They are the same as or different from each other;
상기 L 및 R11~R12에서 아릴렌기, 헤테로아릴렌기, 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 또는 비치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.An arylene group, a heteroarylene group, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group in L and R 11 to R 12 , Alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 to C 40 alkynyl group, C 6 to C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 to C 40 aryloxy group, C 1 to C 40 Alkyloxy group, C 6 -C 40 arylamine group, C 3 -C 40 cycloalkyl group, nuclear atom 3-40 heterocycloalkyl group, C 1 -C 40 alkylsilyl group, C 1 -C 40 boron alkyl group, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ C 40 aryl group consisting of silyl When standing substituted with one or more substituents selected or may be unsubstituted or unsubstituted, wherein the substituent is a plurality, they may be the same or different from each other.
상기 화학식 1로 표시되는 화합물에서, R1 및 Ar1 내지 Ar5 중 적어도 하나가 상기 화학식 2로 표시되는 치환체일 수 있으며, 보다 구체적으로 상기 Ar1이 화학식 2로 표시되는 치환기인 경우가 바람직하다. In the compound represented by Formula 1, at least one of R 1 and Ar 1 to Ar 5 may be a substituent represented by Formula 2, and more preferably, Ar 1 is a substituent represented by Formula 2. .
본 발명의 바람직한 또 다른 일례에 따르면, 상기 R1 및 Ar1 내지 Ar5 중 적어도 하나는 하기 화학식 3으로 표시되는 치환체일 수 있다.According to another preferred embodiment of the present invention, at least one of R 1 and Ar 1 to Ar 5 may be a substituent represented by the following formula (3).
상기 화학식 3에서,In Chemical Formula 3,
*는 상기 화학식 1에 결합되는 부분을 의미하고;* Means a moiety bonded to Formula 1;
L2은 단일결합이거나, 또는 C6~C18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택되고, 바람직하게는 단일결합이거나 페닐렌기 또는 비페닐렌기일 수 있다. L 2 is a single bond, or is C 6 ~ C can be an aryl group and a nucleus of atoms of 18 is selected from the group consisting of a hetero arylene of 5 to 18, preferably or a single bond may be a phenylene group or biphenylene.
R13 및 R14는 서로 동일하거나 또는 상이하며, 각각 독립적으로 C1~C40의 알킬기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 또는 상기 R13 및 R14가 결합하여 축합 고리를 형성할 수 있으며;R 13 and R 14 are the same as or different from each other, and each independently represent an alkyl group of C 1 to C 40 , an aryl group of C 6 to C 40 , a heteroaryl group of 5 to 40 nuclear atoms, and a C 6 to C 60 group ; Or an arylamine group, or R 13 and R 14 may combine to form a condensed ring;
상기 R13 ~ R14에서, 알킬기, 아릴기, 헤테로아릴기 및 아릴아민기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 또는 비치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.R 13 ~ In R 14 , an alkyl group, an aryl group, a heteroaryl group and an arylamine group 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 6 ~ C 40 aryl group, heteroaryl group of 5 to 40 nuclear atoms, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 Arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 40 the arylboronic group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ C 40 substituted to the aryl silyl group substituents of two or more selected from the group consisting or unsubstituted of In this case, when the substituents are plural, they may be the same or different from each other.
상기 화학식 1로 표시되는 화합물에서, R1 및 Ar1 내지 Ar5 중 적어도 하나가 상기 화학식 3으로 표시되는 치환체일 수 있으며, 보다 구체적으로 상기 Ar1이 화학식 3으로 표시되는 치환기인 경우가 바람직하다. In the compound represented by Chemical Formula 1, at least one of R 1 and Ar 1 to Ar 5 may be a substituent represented by Chemical Formula 3, and more preferably, Ar 1 is a substituent represented by Chemical Formula 3. .
이상에서 설명한 본 발명의 화합물은 하기 예시되는 화학식 1 내지 화학식 101 중 어느 하나로 표시되는 화합물로 보다 구체화될 수 있다. 그러나 본 발명의 화학식 1로 표시되는 화합물이 하기 예시된 것들에 의해 한정되는 것은 아니다.The compound of the present invention described above may be further embodied as a compound represented by any one of Formulas 1 to 101 illustrated below. However, the compound represented by the formula (1) of the present invention is not limited by those illustrated below.
본 발명에서 알킬은 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 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, 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.
본 발명에서 알케닐(alkenyl)은 탄소-탄소 이중 결합을 1개 이상 가진탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등을 들 수 있으나, 이에 한정되지는 않는다.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.
본 발명에서 알키닐(alkynyl)은 탄소-탄소 삼중 결합을 1개 이상 가진탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등을 들 수 있으나, 이에 한정되지는 않는다.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.
본 발명에서 아릴은 단독 고리 또는 2 이상의 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 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, 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. In addition, 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.
본 발명에서 헤테로아릴은 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 등을 들 수 있으나, 이에 한정되지는 않는다.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. In addition, 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. Examples of such heteroaryl 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.
본 발명에서 아릴옥시는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 6 내지 60의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, aryloxy is a monovalent substituent represented by RO-, wherein 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.
본 발명에서 알킬옥시는 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. 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, 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. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
본 발명에서 아민은 R1R2N-로 표시되는 1가의 치환기로, 상기 R1 및 R2는 각각 독립적으로 탄소수 1 내지 60의 알킬, 탄소수 6 내지 60의 아릴 및 핵 원자수 5 내지 60의 헤테로아릴을 의미한다.In the present invention, 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.
본 발명에서 시클로알킬은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine) 등을 들 수 있으나, 이에 한정되지는 않는다.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.
본 발명에서 헤테로시클로알킬은 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 등을 들 수 있으나, 이에 한정되지는 않는다.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.
본 발명에서 알킬실릴은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, 아릴실릴은 탄소수 6 내지 60의 아릴로 치환된 실릴을 의미한다.In the present invention, alkylsilyl is silyl substituted with alkyl having 1 to 40 carbon atoms, and arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.
본 발명에서 축합 고리는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.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.
본 발명에 따라 화학식 1로 표시되는 화합물은 일반적인 합성방법에 따라 합성될 수 있으며, 일례로 하기 반응식 I에 따라 코어가 합성될 수 있다. 본 발명의 화합물에 대한 상세한 합성 과정은 후술하는 합성예에서 구체적으로 기술하도록 한다. According to the present invention, the compound represented by Chemical Formula 1 may be synthesized according to a general synthetic method, and for example, a core may be synthesized according to Scheme I below. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
[코어(Core) 합성 반응식 I][Core Synthesis Scheme I]
<유기 전계 발광 소자><Organic EL device>
한편, 본 발명의 다른 측면은 상기한 본 발명에 따른 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자(유기 EL 소자)에 관한 것이다.On the other hand, another aspect of the present invention relates to an organic electroluminescent device (organic EL device) comprising the compound represented by the formula (1) according to the present invention.
보다 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.More 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. Includes a compound represented by the formula (1). In this case, the compound may be used alone, or two or more may be used in combination.
상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광보조층, 발광층, 전자수송층 및 전자주입층 중 어느 하나 이상일 수 있고, 이 중에서 적어도 하나의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 구체적으로 상기 화학식 1의 화합물을 포함하는 유기물층은 정공수송층, 전자 수송층, 발광층, 또는 발광보조층인 것이 바람직하다.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. Specifically, the organic material layer including the compound of Formula 1 is preferably a hole transport layer, an electron transport layer, a light emitting layer, or a light emitting auxiliary layer.
본 발명의 유기 전계 발광 소자의 발광층은 호스트 재료를 포함할 수 있는데, 이때 호스트 재료로서 상기 화학식 1의 화합물을 포함할 수 있다. The light emitting layer of the organic electroluminescent device of the present invention may include a host material, and may include the compound of Formula 1 as the host material.
이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 기판, 양극, 정공주입층, 정공수송층, 발광보조층, 발광층, 전자수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 이때, 상기 정공주입층, 정공수송층, 발광보조층, 발광층, 전자수송층 및 전자주입층 중 하나 이상은 상기 화학식 1로 표시되는 화합물을 포함할 수 있고, 바람직하게는 정공수송층, 전자수송층, 발광층, 발광보조층이 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 한편 상기 전자수송층 위에는 전자주입층이 추가로 적층될 수 있다.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. In this case, at least one of 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, an electron transport layer, a light emitting layer, The light emitting 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.
본 발명의 유기 전계 발광 소자의 구조는 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.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.
본 발명의 유기 전계 발광 소자는 상기 유기물층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는, 당업계에 공지된 재료 및 방법으로 유기물층 및 전극을 형성하여 제조할 수 있다.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.
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.
본 발명의 유기 전계 발광 소자 제조 시 사용되는 기판은 특별히 한정되지 않으나, 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등을 사용할 수 있다.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.
또, 양극 물질로는 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 등을 들 수 있으나, 이에 한정되지는 않는다.In addition, 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.
또, 음극 물질로는 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 등을 들 수 있으나, 이에 한정되지는 않는다.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.
또한, 정공 주입층, 정공 수송층, 전자 주입층 및 전자 수송층은 특별히 한정되는 것은 아니며, 당 업계에 알려진 통상의 물질을 사용할 수 있다.In addition, 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.
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 with reference to Examples. However, the following examples are merely to illustrate the invention, the present invention is not limited by the following examples.
[준비예 1] Core I의 합성Preparation Example 1 Synthesis of Core I
<단계 1> 5-bromobenzo[b]naphtho[1,2-e][1,4]dioxine의 합성Step 1 Synthesis of 5-bromobenzo [b] naphtho [1,2-e] [1,4] dioxine
4-bromonaphthalene-1,2-diol 100 g (0.418 mol)에 DMF 700 mL 를 가하였다. 상온에서 1,2-difluorobenzene 95.3 g (0.836 mol) 과 potassium carbonate 143.5 g (1.04 mol)를 첨가하고 150℃에서 48 시간동안 가열환류하였다. 반응액을 냉각시킨 얼음물에 천천히 적가하여 반응을 종결하였다. EA 2.0 L로 유기층을 추출하고 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 48 g (수율 35%)을 얻었다.To 100 g (0.418 mol) of 4-bromonaphthalene-1,2-diol was added 700 mL of DMF. 95.3 g (0.836 mol) of 1,2-difluorobenzene and 143.5 g (1.04 mol) of potassium carbonate were added at room temperature, and the mixture was heated and refluxed at 150 ° C. for 48 hours. The reaction solution was slowly added dropwise to the cooled ice water to terminate the reaction. The organic layer was extracted with EA 2.0 L 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 48 g (yield 35%) of the title compound.
1H-NMR (in CDCl3) : δ 8.25 (m, 2H), 7.62 (m, 3H), 6.90 (m, 4H) 1 H-NMR (in CDCl 3 ): δ 8.25 (m, 2H), 7.62 (m, 3H), 6.90 (m, 4H)
[LCMS] : 313.2[LCMS]: 313.2
<단계 2> 2-(benzo[b]naphtho[1,2-e][1,4]dioxin-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 의 합성Step 2 Synthesis of 2- (benzo [b] naphtho [1,2-e] [1,4] dioxin-5-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane
5-bromobenzo[b]naphtho[1,2-e][1,4]dioxine 48.0 g (0.153 mol)과 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) 58.0 g (0.23 mol)에 dioxane 1.0 L를 가하였다. Pd(dppf)Cl2 6.2 g (7.6 mmol), KOAc 37 g (0.38 mol), 반응액에 첨가하였다. 반응액을 120℃에서 6시간 동안 가열환류하였다. 상온으로 온도를 냉각하고 반응액에 정제수 1.0 L로 반응을 종결하고 E.A 2.0 L로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 52 g (수율 94%)을 얻었다.48.0 g (0.153 mol) of 5-bromobenzo [b] naphtho [1,2-e] [1,4] dioxine with 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2 1.0 L of dioxane was added to 58.0 g (0.23 mol) of, 2'-bi (1,3,2-dioxaborolane). 6.2 g (7.6 mmol) of Pd (dppf) Cl 2 , 37 g (0.38 mol) of KOAc were added to the reaction solution. The reaction solution was heated to reflux at 120 ° C. for 6 hours. After cooling to room temperature, the reaction was terminated with 1.0 L of purified water, extracted with EA 2.0 L, 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 52 g (yield 94%) of the title compound.
1H-NMR (in CDCl3) : δ 8.25 (m, 2H), 7.62 (m, 3H), 6.90 (m, 4H), 1.20 (s, 12H) 1 H-NMR (in CDCl 3 ): δ 8.25 (m, 2H), 7.62 (m, 3H), 6.90 (m, 4H), 1.20 (s, 12H)
[LCMS] : 360.2[LCMS]: 360.2
<단계 3> 5-(2-nitrophenyl)benzo[b]naphtho[1,2-e][1,4]dioxine 의 합성Step 3 Synthesis of 5- (2-nitrophenyl) benzo [b] naphtho [1,2-e] [1,4] dioxine
2-(benzo[b]naphtho[1,2-e][1,4]dioxin-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 52.0 g (0.144 mol)에 Toluene 1.0 L, EtOH 250 mL, H2O 250mL 를 가하였다. 1-bromo-2-nitrobenzene 28.8 g (0.143 mol), Pd(PPh3)4 8.3 g (7.2 mmol), K2CO3 50 g (0.36 mol), 반응액에 첨가하였다. 반응액을 110℃에서 6시간 동안 가열환류하였다. 상온으로 온도를 냉각하고 반응액에 정제수 1.0 L로 반응을 종결하고 E.A 2.0 L로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 45 g (수율 88%)을 얻었다.2- (benzo [b] naphtho [1,2-e] [1,4] dioxin-5-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane 52.0 g (0.144 mol) 1.0 L of Toluene, 250 mL of EtOH, and 250 mL of H 2 O were added thereto. 28.8 g (0.143 mol) of 1-bromo-2-nitrobenzene, 8.3 g (7.2 mmol) of Pd (PPh 3 ) 4 , and 50 g (0.36 mol) of K 2 CO 3 were added to the reaction solution. The reaction solution was heated to reflux at 110 ° C. for 6 hours. After cooling to room temperature, the reaction was terminated with 1.0 L of purified water, extracted with EA 2.0 L, 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 45 g (yield 88%) of the title compound.
1H-NMR (in CDCl3) : δ 8.25 (m, 2H), 7.90 (m, 4H), 7.62 (m, 3H), 6.90 (m, 4H) 1 H-NMR (in CDCl 3 ): δ 8.25 (m, 2H), 7.90 (m, 4H), 7.62 (m, 3H), 6.90 (m, 4H)
[LCMS] : 355.3 [LCMS]: 355.3
<단계 4> Core I의 합성Step 4 Synthesis of Core I
5-(2-nitrophenyl)benzo[b]naphtho[1,2-e][1,4]dioxine 45.0 g (0.127 mol)에 DCB 1 L를 가하였다. Triethyl phosphine 100 g (0.381 mol)을 반응액에 첨가하고 180℃에서 12시간 동안 가열환류하였다. 반응액을 상온으로 냉각하고 정제수 500 mL를 가하여 반응을 종결하고 E.A 1.0 L로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 34 g (수율 83 %)을 얻었다.1 L of DCB was added to 45.0 g (0.127 mol) of 5- (2-nitrophenyl) benzo [b] naphtho [1,2-e] [1,4] dioxine. Triethyl phosphine 100 g (0.381 mol) was added to the reaction solution and heated to reflux at 180 ° C. for 12 hours. The reaction solution was cooled to room temperature, 500 mL of purified water was added to terminate the reaction, and extracted with 1.0 L of EA, followed by washing 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 34 g (yield 83%) of the title compound.
1H-NMR (in CDCl3) : δ 10.5 (s, 1H), 8.90 (d, 1H), 8.10 (m, 2H), 7.65 (m, 5H), 6.90 (m, 4H) 1 H-NMR (in CDCl 3 ): δ 10.5 (s, 1H), 8.90 (d, 1H), 8.10 (m, 2H), 7.65 (m, 5H), 6.90 (m, 4H)
[LCMS] : 323.3 [LCMS]: 323.3
[합성예 1] 화합물 1의 합성Synthesis Example 1 Synthesis of Compound 1
준비예 1에서 제조된 화합물 5.0 g (15.5 mmol)과 iodobenzene (3.79 g, 18.6 mmol), Pd2(dba)3 (0.63 g, 0.694 mmol), P(t-bu)3 (50% in xylene, 0.56 g, 1.388 mmol), tBuONa (2.66 g, 27.76 mmol) 및 toluene 200 ml 를 혼합하고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 에틸아세테이트로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물을 5.5 g(88%) 얻었다.5.0 g (15.5 mmol) of compound 1 prepared in Preparation Example 1, iodobenzene (3.79 g, 18.6 mmol), Pd 2 (dba) 3 (0.63 g, 0.694 mmol), P (t-bu) 3 (50% in xylene, 0.56 g, 1.388 mmol), tBuONa (2.66 g, 27.76 mmol) and 200 ml of toluene were mixed and stirred at 110 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with ethyl acetate and filtered with MgSO 4 . After removing the solvent of the filtered organic layer using column chromatography to give the title compound 5.5 g (88%).
[합성예 2] 화합물 4의 합성Synthesis Example 2 Synthesis of Compound 4
준비예 1에서 제조된 화합물 5.0 g (15.5 mmol)과 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 10.3 g (30.1 mmol)에 dioxane 100 mL를 가하였다. Pd(OAc)2 0.17 g (0.75 mmol), P(t-Bu)3 0.61 g (1.5 mmol), K2CO3 6.2 g (45.1 mmol)을 반응액에 첨가하고 120℃에서 12시간 가열환류하였다. 상온으로 온도를 냉각하고 반응액에 정제수 300 mL로 반응을 종결하였다. 혼합액을 E.A 500 mL로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 5.3 g (수율 55%)을 얻었다.100 mL of dioxane was added to 5.0 g (15.5 mmol) of the compound prepared in Preparation Example 1 and 10.3 g (30.1 mmol) of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine. 0.17 g (0.75 mmol) of Pd (OAc) 2 , 0.61 g (1.5 mmol) of P (t-Bu) 3 , and 6.2 g (45.1 mmol) of K 2 CO 3 were added to the reaction mixture, and the mixture was heated and refluxed at 120 ° C. for 12 hours. . The temperature was cooled to room temperature, and the reaction was terminated with 300 mL of purified water. The mixture was extracted with 500 mL 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 5.3 g (yield 55%) of the title compound.
[LCMS] : 630.7[LCMS]: 630.7
[합성예 3] 화합물 5의 합성Synthesis Example 3 Synthesis of Compound 5
준비예 1에서 제조된 화합물과 2-(3-chlorophenyl)-4,6-diphenylpyrimidine 을 사용한 것을 제외하고는, 상기 합성예 2 와 동일한 과정을 수행하여 목적 화합물 6 g (수율 61%)을 얻었다.Except for using the compound prepared in Preparation Example 1 and 2- (3-chlorophenyl) -4,6-diphenylpyrimidine, the same procedure as in Synthesis Example 2 was carried out to obtain the target compound 6 g (yield 61%).
[LCMS] : 629.7 [LCMS]: 629.7
[합성예 4] 화합물 6의 합성Synthesis Example 4 Synthesis of Compound 6
준비예 1에서 제조된 화합물과 2-(3-chlorophenyl)-4,6-diphenylpyrimidine 을 사용한 것을 제외하고는, 상기 합성예 2 와 동일한 과정을 수행하여 목적 화합물 6.3 g (수율 61%)을 얻었다.Except for using the compound prepared in Preparation Example 1 and 2- (3-chlorophenyl) -4,6-diphenylpyrimidine, the same procedure as in Synthesis Example 2 was carried out to obtain 6.3 g (yield 61%) of the title compound.
[LCMS] : 629.7 [LCMS]: 629.7
[합성예 5] 화합물 7의 합성Synthesis Example 5 Synthesis of Compound 7
준비예 1에서 제조된 화합물과 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 을 사용한 것을 제외하고는, 상기 합성예 2 와 동일한 과정을 수행하여 목적 화합물 4.0 g (수율 52%)을 얻었다.Except for using the compound prepared in Preparation Example 1 and 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine, the same procedure as in Synthesis Example 2 was carried out to give the target compound 4.0 g (Yield 52%) was obtained.
[LCMS] : 630.7[LCMS]: 630.7
[합성예 6] 화합물 8의 합성Synthesis Example 6 Synthesis of Compound 8
준비예 1에서 제조된 화합물과 2-(4-chlorophenyl)-4,6-diphenylpyrimidine 을 사용한 것을 제외하고는, 상기 합성예 2 와 동일한 과정을 수행하여 목적 화합물 4.0 g (수율 52%)을 얻었다.Except for using the compound prepared in Preparation Example 1 and 2- (4-chlorophenyl) -4,6-diphenylpyrimidine, the same procedure as in Synthesis Example 2 was carried out to obtain 4.0 g (yield 52%) of the title compound.
[LCMS] : 629.7[LCMS]: 629.7
[합성예 7] 화합물 9의 합성Synthesis Example 7 Synthesis of Compound 9
준비예 1에서 제조된 화합물과 4-(4-chlorophenyl)-2,6-diphenylpyrimidine을 사용한 것을 제외하고는, 상기 합성예 2 와 동일한 과정을 수행하여 목적 화합물 4.0 g (수율 52%)을 얻었다.Except for using the compound prepared in Preparation Example 1 and 4- (4-chlorophenyl) -2,6-diphenylpyrimidine, the same procedure as in Synthesis Example 2 was carried out to obtain 4.0 g (yield 52%) of the title compound.
[LCMS] : 629.7[LCMS]: 629.7
[합성예 8] 화합물 10의 합성Synthesis Example 8 Synthesis of Compound 10
준비예 1에서 제조된 화합물 3.8 g (11.8 mmol)과 2-(3'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine 을 dioxane 8.0 g (17.1 mmol)에 dioxane 100 mL를 가하였다. Pd(OAc)2 0.13 g (0.57 mmol), XPhos 0.54 g (1.1 mmol), Cs2CO3 7.5 g (22.9 mmol)을 반응액에 첨가하고 120℃에서 12시간 가열환류하였다. 상온으로 온도를 냉각하고 반응액에 정제수 300 mL로 반응을 종결하였다. 혼합액을 E.A 500 mL로 추출한 후, 증류수로 세척하였다. 얻어진 유기층을 무수 MgSO4로 건조하고, 감압증류하고 실리카겔 컬럼크로마토그래피로 정제하여 목적 화합물 3.4 g (수율 42%)을 얻었다.3.8 g (11.8 mmol) of the compound prepared in Preparation Example 1 and 2- (3'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine To dioxane 8.0 g (17.1 mmol) was added 100 mL of dioxane. 0.13 g (0.57 mmol) of Pd (OAc) 2 , 0.54 g (1.1 mmol) of XPhos, and 7.5 g (22.9 mmol) of Cs 2 CO 3 were added to the reaction solution, and the mixture was heated and refluxed at 120 ° C. for 12 hours. The temperature was cooled to room temperature, and the reaction was terminated with 300 mL of purified water. The mixture was extracted with 500 mL 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 3.4 g (yield 42%) of the title compound.
[LCMS] : 706.8 [LCMS]: 706.8
[합성예 9] 화합물 11의 합성Synthesis Example 9 Synthesis of Compound 11
준비예 1에서 제조된 화합물과 2-(4'-bromo-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, 상기 합성예 8 과 동일한 과정을 수행하여 목적 화합물 4.5 g (수율 54%)을 얻었다.Except for using the compound prepared in Preparation Example 1 and 2- (4'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine, 4.5 g (yield 54%) of the title compound was obtained by the same procedure as in Synthesis Example 8.
[LCMS] : 706.8[LCMS]: 706.8
[합성예 10] 화합물 12의 합성Synthesis Example 10 Synthesis of Compound 12
준비예 1에서 제조된 화합물과 2-(4'-bromo-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, 상기 합성예 8 과 동일한 과정을 수행하여 목적 화합물 4.5 g (수율 54%)을 얻었다.Except for using the compound prepared in Preparation Example 1 and 2- (4'-bromo- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5-triazine, 4.5 g (yield 54%) of the title compound was obtained by the same procedure as in Synthesis Example 8.
[LCMS] : 706.8 [LCMS]: 706.8
[합성예 11] 화합물 15의 합성Synthesis Example 11 Synthesis of Compound 15
준비예 1에서 제조된 화합물과 2-(4'-bromo-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine을 사용한 것을 제외하고는, 상기 합성예 8 과 동일한 과정을 수행하여 목적 화합물 4.5 g (수율 54%)을 얻었다.Except for using the compound prepared in Preparation Example 1 and 2- (4'-bromo- [1,1'-biphenyl] -4-yl) -4,6-diphenyl-1,3,5-triazine, 4.5 g (yield 54%) of the title compound was obtained by the same procedure as in Synthesis Example 8.
[LCMS] : 705.8[LCMS]: 705.8
[합성예 12] 화합물 16의 합성Synthesis Example 12 Synthesis of Compound 16
반응물로서 준비예 1에서 제조된 화합물과 4-(3'-chloro-[1,1'-biphenyl]-3-yl)-2,6-diphenylpyrimidine 를 사용한 것을 제외하고는, 상기 합성예 2와 동일한 과정을 수행하여 목적 화합물 4.5 g (수율 41%)을 얻었다.Except for using the compound prepared in Preparation Example 1 and 4- (3'-chloro- [1,1'-biphenyl] -3-yl) -2,6-diphenylpyrimidine as the reactant, the same as in Synthesis Example 2 The procedure was followed to obtain 4.5 g (41% yield) of the title compound.
[LCMS] : 705.8[LCMS]: 705.8
[합성예 13] 화합물 17의 합성Synthesis Example 13 Synthesis of Compound 17
반응물로서 준비예 1에서 제조된 화합물과 4-(4'-chloro-[1,1'-biphenyl]-3-yl)-2,6-diphenylpyrimidine 를 사용한 것을 제외하고는, 상기 합성예 2와 동일한 과정을 수행하여 목적 화합물 4.5 g (수율 41%)을 얻었다.Except for using the compound prepared in Preparation Example 1 and 4- (4'-chloro- [1,1'-biphenyl] -3-yl) -2,6-diphenylpyrimidine as the reactant, the same as in Synthesis Example 2 The procedure was followed to obtain 4.5 g (41% yield) of the title compound.
[LCMS] : 705.8 [LCMS]: 705.8
[합성예 14] 화합물 18의 합성Synthesis Example 14 Synthesis of Compound 18
반응물로서 준비예 1에서 제조된 화합물과 4-(4'-chloro-[1,1'-biphenyl]-4-yl)-2,6-diphenylpyrimidine 를 사용한 것을 제외하고는, 상기 합성예 2 와 동일한 과정을 수행하여 목적 화합물 5.2 g (수율 48%)을 얻었다.Except for using the compound prepared in Preparation Example 1 and 4- (4'-chloro- [1,1'-biphenyl] -4-yl) -2,6-diphenylpyrimidine as the reactant, the same as in Synthesis Example 2 The procedure was carried out to obtain 5.2 g (yield 48%) of the title compound.
[LCMS] : 705.8[LCMS]: 705.8
[합성예 15] 화합물 19의 합성Synthesis Example 15 Synthesis of Compound 19
반응물로서 준비예 1에서 제조된 화합물과 2-bromo-4-(4-(naphthalen-1-yl)phenyl)quinazoline 를 사용한 것을 제외하고는, 상기 합성예 8 과 동일한 과정을 수행하여 목적 화합물 4.5 g (수율 58%)을 얻었다.4.5 g of the target compound was performed in the same manner as in Synthesis Example 8, except that the compound prepared in Preparation Example 1 and 2-bromo-4- (4- (naphthalen-1-yl) phenyl) quinazoline were used as reactants. (Yield 58%) was obtained.
[LCMS] : 653.7[LCMS]: 653.7
[합성예 16] 화합물 20의 합성Synthesis Example 16 Synthesis of Compound 20
반응물로서 준비예 1에서 제조된 화합물과 4-([1,1'-biphenyl]-4-yl)-2-bromoquinazoline 를 사용한 것을 제외하고는, 상기 합성예 8 과 동일한 과정을 수행하여 목적 화합물 4.7 g (수율 66%)을 얻었다.Except for using the compound prepared in Preparation Example 1 and 4-([1,1'-biphenyl] -4-yl) -2-bromoquinazoline as a reactant, the same procedure as in Synthesis Example 8 was carried out to give the title compound 4.7 g (yield 66%) was obtained.
[LCMS] : 603.7[LCMS]: 603.7
[실시예 1 ~ 10] 녹색 유기 EL 소자의 제작[Examples 1 to 10] Fabrication of Green Organic EL Devices
합성예에서 합성된 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 EL 소자를 제작하였다.After the compound synthesized in the synthesis example was subjected to high purity sublimation purification by a commonly known method, a green organic EL device was manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 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.First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ 화합물 (1, 4~7, 10~11, 16~18) + 10 % Ir(ppy)3 (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 EL 소자를 제작하였다. M-MTDATA (60 nm) / TCTA (80 nm) / Compound (1, 4-7, 10-11, 16-18) + 10% Ir (ppy) 3 (30nm) / BCP An organic EL device was fabricated by laminating in order of 10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm).
m-MTDATA, TCTA, Ir(ppy)3, CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 , CBP and BCP are as follows.
[비교예 1] 녹색 유기 EL 소자의 제작Comparative Example 1 Fabrication of Green Organic EL Device
발광층 형성시 발광 호스트 물질로서 합성예에서 합성된 화합물 대신 CBP를 사용하는 것을 제외하고는, 상기 실시예 1과 동일한 과정으로 녹색 유기 EL 소자를 제작하였다.A green organic EL device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound synthesized in Synthesis Example as a light emitting host material when forming the emission layer.
[평가예][Evaluation Example]
실시예 1 ~ 10 및 비교예 1에서 제작한 각각의 녹색 유기 EL 소자에 대하여 전류밀도 (10) mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 2에 나타내었다.For each of the green organic EL devices produced in Examples 1 to 10 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at current density (10) mA / cm 2 were measured, and the results are shown in Table 2 below. It was.
| 샘플Sample | 호스트Host | 구동 전압 (V)Driving voltage (V) | EL 피크 (nm)EL peak (nm) | 전류효율 (cd/A)Current efficiency (cd / A) |
| 실시예 1Example 1 | 1One | 7.207.20 | 525525 | 36.436.4 |
| 실시예 2Example 2 | 44 | 6.826.82 | 518518 | 39.939.9 |
| 실시예 3Example 3 | 55 | 6.986.98 | 517517 | 40.240.2 |
| 실시예 4Example 4 | 66 | 6.896.89 | 515515 | 38.438.4 |
| 실시예 5Example 5 | 77 | 6.786.78 | 518518 | 42.442.4 |
| 실시예 6Example 6 | 1010 | 6.696.69 | 518518 | 42.842.8 |
| 실시예 7Example 7 | 1111 | 6.726.72 | 517517 | 41.741.7 |
| 실시예 8Example 8 | 1616 | 6.706.70 | 515515 | 42.042.0 |
| 실시예 9Example 9 | 1717 | 6.826.82 | 518518 | 40.340.3 |
| 실시예 10Example 10 | 1818 | 6.846.84 | 518518 | 41.241.2 |
| 비교예 1Comparative Example 1 | CBPCBP | 6.936.93 | 516516 | 38.238.2 |
상기 표 2에 나타낸 바와 같이, 본 발명에 따른 화합물(1, 4~7, 10~11, 16~18)을 발광층으로 사용하는 실시예 1~10의 녹색 유기 EL 소자는, 종래 CBP를 사용한 비교예 1의 녹색 유기 EL 소자와 비교해 볼 때 효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있다.As shown in Table 2, the green organic EL device of Examples 1 to 10 using the compounds (1, 4 to 7, 10 to 11, 16 to 18) according to the present invention as a light emitting layer is compared using a conventional CBP. Compared with the green organic EL device of Example 1, it can be seen that it shows better performance in terms of efficiency and driving voltage.
[[
실시예 11~20] 적색 유기 EL 소자의 제조Examples 11 to 20 Fabrication of Red Organic EL Devices
합성예에서 합성된 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 적색 유기 전계 발광 소자를 제작하였다.The compound synthesized in the synthesis example was subjected to high purity sublimation purification by a commonly known method, and then a red organic EL device was manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 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.First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ 화합물 (1, 5, 8~9, 15~20) + 10 % (piq)2Ir(acac) (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다.M-MTDATA (60 nm) / TCTA (80 nm) / Compound (1, 5, 8-9, 15-20) + 10% (piq) 2 Ir (acac) (30nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) were laminated in order to fabricate an organic EL device.
[비교예 2]Comparative Example 2
발광층 형성시 발광 호스트 물질로서 상기 합성예 1의 화합물 대신 CBP를 사용하는 것을 제외하고는, 상기 실시예 11과 동일한 과정으로 적색 유기 전계 발광 소자를 제작하였다.A red organic electroluminescent device was manufactured in the same manner as in Example 11, except that CBP was used instead of the compound of Synthesis Example 1 as a light emitting host material when forming the emission layer.
상기 실시예 11 ~ 20 및 비교예 2에서 사용된 m-MTDATA, (piq)2Ir(acac), CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, (piq) 2 Ir (acac), CBP, and BCP used in Examples 11 to 20 and Comparative Example 2 are as follows.
[평가예][Evaluation Example]
실시예 11 ~ 20 및 비교예 2에서 제작된 각각의 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율을 측정하고, 그 결과를 하기 표 3에 나타내었다.For each organic EL device manufactured in Examples 11 to 20 and Comparative Example 2, the driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured, and the results are shown in Table 3 below.
| 샘플Sample | 호스트Host | 구동 전압 (V)Driving voltage (V) | 전류효율 (cd/A)Current efficiency (cd / A) |
| 실시예 11Example 11 | 1One | 5.305.30 | 8.928.92 |
| 실시예 12Example 12 | 55 | 5.125.12 | 10.510.5 |
| 실시예 13Example 13 | 88 | 4.924.92 | 10.410.4 |
| 실시예 14Example 14 | 99 | 4.874.87 | 9.49.4 |
| 실시예 15Example 15 | 1515 | 4.904.90 | 9.89.8 |
| 실시예 16Example 16 | 1616 | 4.774.77 | 11.511.5 |
| 실시예 17Example 17 | 1717 | 4.724.72 | 10.210.2 |
| 실시예 18Example 18 | 1818 | 4.804.80 | 11.011.0 |
| 실시예 19Example 19 | 1919 | 4.594.59 | 12.812.8 |
| 실시예 20Example 20 | 2020 | 4.654.65 | 12.012.0 |
| 비교예 2Comparative Example 2 | CBPCBP | 5.255.25 | 8.28.2 |
상기 표 3에 나타낸 바와 같이, 본 발명에 따른 화합물(1, 5, 8~9, 15~20)을 발광층의 재료로 사용하는 실시예 11~20의 적색 유기 전계 발광소자는 종래 CBP를 발광층의 재료로 사용한 비교예 2의 적색 유기 전계 발광 소자와 비교해 볼 때 효율 및 구동전압 면에서 우수한 성능을 나타내는 것을 알 수 있다.As shown in Table 3, the red organic electroluminescent device of Examples 11 to 20, which uses the compounds (1, 5, 8-9, 15-20) according to the present invention as a material of the light emitting layer, has conventional CBP When compared with the red organic electroluminescent element of the comparative example 2 used as a material, it turns out that it shows the outstanding performance in efficiency and a drive voltage.
Claims (11)
- 하기 화학식 1로 표시되는 것을 특징으로 하는 화합물. A compound represented by the following formula (1).[화학식 1][Formula 1]
상기 화학식 1에서,In Chemical Formula 1,X1은 O, S, 및 N(Ar1)로 이루어진 군에서 선택되고;X 1 is selected from the group consisting of O, S, and N (Ar 1 );X2 및 X3는 서로 동일하거나 또는 상이하며, 각각 독립적으로 O, S, N(Ar1), C(Ar2)(Ar3) 및 Si(Ar4)(Ar5)로 구성된 군으로부터 선택되고;X 2 and X 3 are the same as or different from each other, and each independently selected from the group consisting of O, S, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ) Become;Y1 내지 Y12은 서로 동일하거나 또는 상이하며, 각각 독립적으로 N 또는 C(R1)에서 선택되고, 이때 C(R1)이 복수 개일 경우 복수의 R1은 서로 동일하거나 또는 상이하며, Y 1 to Y 12 are the same as or different from each other, and are each independently selected from N or C (R 1 ), wherein when there are a plurality of C (R 1 ), a plurality of R 1 are the same or different from each other,R1은 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, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C1~C60의 포스핀기, C1~C60의 포스핀옥사이드기 및 C1~C60의 아민기로 이루어진 군에서 선택되거나, 또는 인접한 기와 결합하여 축합 고리를 형성할 수 있고,R 1 is each independently 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, 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 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 1 to C 60 A phosphine group, a C 1 to C 60 phosphine oxide group and a C 1 to C 60 amine group, or may be combined with an adjacent group to form a condensed ring,Ar1 내지 Ar5는 서로 동일하거나 또는 상이하며, 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, 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,Ar 1 to Ar 5 are the same as or different from each other, and 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 , Heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group having 6 to C 60 atoms, heteroaryl group having 5 to 60 nuclear atoms, alkyloxy group having 1 to C 40 atoms, aryl jade having 6 to C 60 atoms group, C 1 ~ C 40 alkylsilyl group, C 6 ~ C aryl silyl group of 60, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ aryl phosphine of C 60 It is selected from the group consisting of a pin group, a C 6 ~ C 60 aryl phosphine oxide group and a C 6 ~ C 60 arylamine group,상기 R1 및 Ar1 내지 Ar5에서 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 포스핀기, 포스핀옥사이드기 및 아민기는 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, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C1~C60의 포스핀기, C1~C60의 포스핀옥사이드기 및 C1~C60의 아민기로 이루어진 군에서 선택된 1종 이상으로 치환 또는 비치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들의 서로 동일하거나 또는 상이할 수 있다. In R 1 and Ar 1 to Ar 5 , an 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, an aryl boron group, a phosphine group, a phosphine oxide groups and amine groups, each independently, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C of 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ~ alkyloxy group of C 40, 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 1 ~ C 60 phosphine group, C 1 to C 60, and phosphine oxide groups and C 1 to be unsubstituted or substituted with one or more selected from the group consisting of C 60 amines, where the substituent of the plurality Wu, can be those of the same or different from each other. - 제1항에 있어서, The method of claim 1,상기 X1은 N(Ar1)인 것을 특징으로 하는 화합물.X 1 is N (Ar 1 ), characterized in that the compound.
- 제1항에 있어서, The method of claim 1,상기 화학식 1로 표시되는 화합물은 하기 화학식 C-1 내지 C-15 중 어느 하나로 표시되는 것을 특징으로 하는 화합물.The compound represented by Formula 1 is represented by any one of the following formulas C-1 to C-15.
상기 화학식 C-1 내지 C-15에서,In Chemical Formulas C-1 to C-15,Y1 내지 Y12 및 Ar1 내지 Ar5는 화학식 1에서 정의한 바와 동일하다.Y 1 to Y 12 and Ar 1 to Ar 5 are the same as defined in Chemical Formula 1. - 제1항에 있어서,The method of claim 1,상기 R1 및 Ar1 내지 Ar5 중 적어도 하나는 하기 화학식 2로 표시되는 치환체인 것을 특징으로 하는 화합물.At least one of the R One And Ar One To Ar 5 A compound characterized in that the substituent represented by the formula (2).[화학식 2][Formula 2]
상기 화학식 2에서,In Chemical Formula 2,*는 상기 화학식 1에 결합되는 부분을 의미하고;* Means a moiety bonded to Formula 1;L은 단일결합이거나, 또는 C6~C18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택되고;L is a single bond, or is C 6 ~ C 18 aryl group and a nuclear atoms selected from the group consisting of a hetero arylene of 5 to 18;Z1 내지 Z5는 서로 동일하거나 상이하며, 각각 독립적으로 N 또는 C(R11)이며, 다만 Z1 내지 Z5 중 적어도 하나는 N이고, 이때 R11이 복수인 경우, 이들은 서로 동일하거나 상이하며;Z 1 to Z 5 are the same as or different from each other, and each independently N or C (R 11 ), provided that at least one of Z 1 to Z 5 is N, wherein when R 11 is plural, they are the same or different from each other. To;R11은 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C40의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며,R 11 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 6 -C 40 aryl group, of nuclear atoms of 5 to 40 heteroaryl group, C 6 ~ C 40 of the aryloxy group, C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group of , C 6 ~ C 40 arylamine group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group , C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ selected from the group consisting of C 40 or aryl silyl, and groups bonded to adjacent or may form a condensed ring,상기 L 및 R11에서 아릴렌기, 헤테로아릴렌기, 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다. Arylene group, heteroarylene group, alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group in L and R 11 , Alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenes group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ~ C 40, alkyloxy group of C 1 ~ C 40 of the , C 6 -C 40 arylamine group, C 3 -C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 alkyl boron group , C 6 ~ C 40 aryl group of boron, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ from the group consisting of C 40 arylsilyl of It may be substituted or unsubstituted with one or more selected substituents, wherein when the substituents are plural, they may be the same or different from each other. - 제4항에 있어서,The method of claim 4, wherein상기 R1 및 Ar1 내지 Ar5 중 적어도 하나는 하기 A-1 내지 A-15로 표시되는 치환체로 이루어진 군에서 선택되는 것을 특징으로 하는 화합물.At least one of R 1 and Ar 1 to Ar 5 is selected from the group consisting of substituents represented by A-1 to A-15.
상기 A-1 내지 A-15에서,In the above A-1 to A-15,L 및 R11은 상기 화학식 2에서 정의된 바와 같고, L and R 11 are the same as defined in Formula 2,n은 0 내지 4의 정수이며, n is an integer of 0 to 4,R12는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며, 이때 R12가 복수인 경우, 이들은 서로 동일하거나 또는 상이하며;R 12 is 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 , nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 40 aryl group, nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 aryl amine group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group of the arylboronic, C 6 ~ C 40 aryl phosphine Fin group, C 6 ~ C 40 aryl phosphine oxide group and C 6 ~ C 40 It may be selected from the group consisting of arylsilyl group, or by combining with an adjacent group to form a condensed ring, wherein when R 12 is a plurality , They are the same as or different from each other;상기 L 및 R11~R12에서 아릴렌기, 헤테로아릴렌기, 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 또는 비치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.An arylene group, a heteroarylene group, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group in L and R 11 to R 12 , Alkylsilyl group, alkyl boron group, aryl boron group, aryl phosphine group, aryl phosphine oxide group and aryl silyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 to C 40 alkynyl group, C 6 to C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 to C 40 aryloxy group, C 1 to C 40 Alkyloxy group, C 6 -C 40 arylamine group, C 3 -C 40 cycloalkyl group, nuclear atom 3-40 heterocycloalkyl group, C 1 -C 40 alkylsilyl group, C 1 -C 40 boron alkyl group, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ C 40 aryl group consisting of silyl When standing substituted with one or more substituents selected or may be unsubstituted or unsubstituted, wherein the substituent is a plurality, they may be the same or different from each other. - 제1항에 있어서,The method of claim 1,상기 R1 및 Ar1 내지 Ar5 중 적어도 하나는 하기 화학식 3으로 표시되는 치환체로 이루어진 군에서 선택되는 것을 특징으로 하는 화합물.At least one of the R One And Ar One To Ar 5 A compound characterized in that it is selected from the group consisting of substituents represented by the following formula (3).[화학식 3][Formula 3]
상기 화학식 3에서,In Chemical Formula 3,*는 상기 화학식 1에 결합되는 부분을 의미하고;* Means a moiety bonded to Formula 1;L2은 단일결합이거나, 또는 C6~C18의 아릴렌기 및 핵원자수 5 내지 18의 헤테로아릴렌기로 이루어진 군에서 선택되고, L 2 is selected from the group consisting of a single bond, or is C 6 ~ C 18 arylene group and a nuclear atoms of 5 to 18 hetero arylene group of,R13 및 R14는 서로 동일하거나 또는 상이하며, 각각 독립적으로 C1~C40의 알킬기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 또는 상기 R13 및 R14가 결합하여 축합 고리를 형성할 수 있으며;R 13 and R 14 are the same as or different from each other, and each independently represent an alkyl group of C 1 to C 40 , an aryl group of C 6 to C 40 , a heteroaryl group of 5 to 40 nuclear atoms, and a C 6 to C 60 group ; Or an arylamine group, or R 13 and R 14 may combine to form a condensed ring;상기 R13 ~ R14에서, 알킬기, 아릴기, 헤테로아릴기 및 아릴아민기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 또는 비치환될 수 있으며, 이때 상기 치환기가 복수인 경우, 이들은 서로 동일하거나 상이할 수 있다.R 13 ~ In R 14 , an alkyl group, an aryl group, a heteroaryl group and an arylamine group 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 6 ~ C 40 aryl group, heteroaryl group of 5 to 40 nuclear atoms, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 Arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 40 the arylboronic group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ C 40 substituted to the aryl silyl group substituents of two or more selected from the group consisting or unsubstituted of In this case, when the substituents are plural, they may be the same or different from each other. - 제1항에 있어서, The method of claim 1,상기 Ar1 내지 Ar5는 각각 독립적으로 C6~C60의 아릴기, 또는 핵원자수 5 내지 60의 헤테로아릴기이며, Ar 1 to Ar 5 are each independently a C 6 ~ C 60 aryl group, or a nuclear atom of 5 to 60 heteroaryl group,복수의 R1은 서로 동일하거나 또는 상이하며, 각각 독립적으로 수소, C1~C40의 알킬기, C6~C60의 아릴기, 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군으로부터 선택되며, A plurality of R 1 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms; ,상기 알킬기, 아릴기와 헤테로아릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 또는 비치환되는 것을 특징으로 하는 화합물.The alkyl group, aryl group and heteroaryl group 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 6 ~ C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 1 -C 40 alkylsilyl group, C 1 -C 40 alkylboron group, C 6 -C 40 aryl boron group, C 6- C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group and C 6 ~ C 40 An arylsilyl group of at least one substituent selected from the group consisting of substituted or unsubstituted compound.
- 제1항에 있어서, The method of claim 1,상기 화학식 1로 표시되는 화합물은 하기 화학식으로 표시되는 화합물 군으로부터 선택되는 것을 특징으로 하는 화합물. The compound represented by Formula 1 is selected from the group of compounds represented by the following formula.
- 양극, 음극, 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, An anode, a cathode, and at least one organic layer interposed between the anode and the cathode,상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항 내지 제8항 중 어느 한 항에 기재된 화학식 1의 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자. At least one of the one or more organic material layer comprises an organic electroluminescent device comprising the compound of formula (1) according to any one of claims 1 to 8.
- 제 9항에 있어서, The method of claim 9,상기 화학식 1로 표시되는 화합물을 포함하는 1층 이상의 유기물층은 발광층, 발광보조층, 전자수송층 및 정공수송층으로 이루어진 군에서 선택되는 것을 특징으로 하는 유기 전계 발광 소자. At least one organic material layer including the compound represented by Formula 1 is an organic electroluminescent device, characterized in that selected from the group consisting of a light emitting layer, a light emitting auxiliary layer, an electron transport layer and a hole transport layer.
- 제9항에 있어서, The method of claim 9,상기 화학식 1로 표시되는 화합물은 발광층의 인광 호스트로 사용되는 것을 특징으로 하는 유기 전계 발광 소자.The compound represented by Chemical Formula 1 is used as a phosphorescent host of the light emitting layer.
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| KR20130142818A (en) * | 2012-06-20 | 2013-12-30 | 주식회사 두산 | Novel compound and organic electroluminescent device comprising the same |
| KR20140000640A (en) * | 2012-06-22 | 2014-01-03 | 에스에프씨 주식회사 | Aromatic compound and organoelectroluminescent device comprising the compound |
| KR20140103391A (en) * | 2013-02-15 | 2014-08-27 | 에스에프씨 주식회사 | Novel organic compounds for organic light-emitting diode and organic light-emitting diode including the same |
| JP2014224100A (en) * | 2013-04-26 | 2014-12-04 | 保土谷化学工業株式会社 | Compound having benzothienoacridan ring structure or benzofuroacridan ring structure, and organic electroluminescence element |
| WO2015156580A2 (en) * | 2014-04-09 | 2015-10-15 | 주식회사 두산 | Organic compound and organic electroluminescent element comprising same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR101115036B1 (en) * | 2009-08-18 | 2012-03-06 | 덕산하이메탈(주) | Compound Containing Thianthrene And Organic Electronic Element Using The Same, Terminal Thereof |
| KR102087648B1 (en) * | 2013-06-03 | 2020-03-11 | 덕산네오룩스 주식회사 | An organic electronic element comprising a layer for improving light efficiency, and an electronic device comprising the same |
-
2014
- 2014-12-22 KR KR1020140186466A patent/KR102339569B1/en active IP Right Grant
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- 2015-12-18 WO PCT/KR2015/013912 patent/WO2016105030A1/en active Application Filing
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20130142818A (en) * | 2012-06-20 | 2013-12-30 | 주식회사 두산 | Novel compound and organic electroluminescent device comprising the same |
| KR20140000640A (en) * | 2012-06-22 | 2014-01-03 | 에스에프씨 주식회사 | Aromatic compound and organoelectroluminescent device comprising the compound |
| KR20140103391A (en) * | 2013-02-15 | 2014-08-27 | 에스에프씨 주식회사 | Novel organic compounds for organic light-emitting diode and organic light-emitting diode including the same |
| JP2014224100A (en) * | 2013-04-26 | 2014-12-04 | 保土谷化学工業株式会社 | Compound having benzothienoacridan ring structure or benzofuroacridan ring structure, and organic electroluminescence element |
| WO2015156580A2 (en) * | 2014-04-09 | 2015-10-15 | 주식회사 두산 | Organic compound and organic electroluminescent element comprising same |
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| Publication number | Publication date |
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| KR102339569B1 (en) | 2021-12-17 |
| KR20160076357A (en) | 2016-06-30 |
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