WO2019194481A1 - Organic electroluminescent compound and organic electroluminescent device comprising the same - Google Patents
Organic electroluminescent compound and organic electroluminescent device comprising the same Download PDFInfo
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- WO2019194481A1 WO2019194481A1 PCT/KR2019/003760 KR2019003760W WO2019194481A1 WO 2019194481 A1 WO2019194481 A1 WO 2019194481A1 KR 2019003760 W KR2019003760 W KR 2019003760W WO 2019194481 A1 WO2019194481 A1 WO 2019194481A1
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- alkyl
- organic electroluminescent
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- 0 CC*(c1c-2cccc1)(c(cc1)c-2c2c1c(-c1ccccc1*1C(C(*3)c4cccc(-c5ccccc5)c4)=*c4c3c(cccc3)c3cc4)c1cc2)c1ccccc1 Chemical compound CC*(c1c-2cccc1)(c(cc1)c-2c2c1c(-c1ccccc1*1C(C(*3)c4cccc(-c5ccccc5)c4)=*c4c3c(cccc3)c3cc4)c1cc2)c1ccccc1 0.000 description 40
- DCEULJBJXKMNHC-UHFFFAOYSA-N CC(C)(c1ccccc1-1)c2c-1c(-c1c(-[n](c3ccccc3c3c4)c3cc(cc3c5c6cccc5)c4cc3[n]6-c3ccccc3)nc(cccc3)c3n1)ccc2 Chemical compound CC(C)(c1ccccc1-1)c2c-1c(-c1c(-[n](c3ccccc3c3c4)c3cc(cc3c5c6cccc5)c4cc3[n]6-c3ccccc3)nc(cccc3)c3n1)ccc2 DCEULJBJXKMNHC-UHFFFAOYSA-N 0.000 description 1
- BAZCBLBNBAALFZ-UHFFFAOYSA-N CC1(C)c(c(-c2nc3ccccc3nc2-[n](c(cccc2)c2c2c3)c2cc(cc2c4c5cccc4)c3cc2[n]5-c2ccccc2)ccc2)c2-c2ccccc12 Chemical compound CC1(C)c(c(-c2nc3ccccc3nc2-[n](c(cccc2)c2c2c3)c2cc(cc2c4c5cccc4)c3cc2[n]5-c2ccccc2)ccc2)c2-c2ccccc12 BAZCBLBNBAALFZ-UHFFFAOYSA-N 0.000 description 1
- RINSCTSANDTSJL-UHFFFAOYSA-N CC1(C)c(ccc(-c2c(-[n](c3ccccc3c3c4)c3cc(cc3c5c6cccc5)c4cc3[n]6-c3ccccc3)nc(cccc3)c3n2)c2)c2-c2ccccc12 Chemical compound CC1(C)c(ccc(-c2c(-[n](c3ccccc3c3c4)c3cc(cc3c5c6cccc5)c4cc3[n]6-c3ccccc3)nc(cccc3)c3n2)c2)c2-c2ccccc12 RINSCTSANDTSJL-UHFFFAOYSA-N 0.000 description 1
- DOOUFHUKDWGGDE-UHFFFAOYSA-O CC=C(C=C(C([NH3+])=C1)N)C1=CC Chemical compound CC=C(C=C(C([NH3+])=C1)N)C1=CC DOOUFHUKDWGGDE-UHFFFAOYSA-O 0.000 description 1
- XZWWOGWTTLPBFV-UHFFFAOYSA-N Nc(ccc1c2C=C=C1)c2N Chemical compound Nc(ccc1c2C=C=C1)c2N XZWWOGWTTLPBFV-UHFFFAOYSA-N 0.000 description 1
- IFJJAKZZOVOCAY-UHFFFAOYSA-N c(cc1)ccc1-[n](c(cccc1)c1c1c2)c1cc(cc1c3c4cccc3)c2cc1[n]4-c1c(-c2ccc(c(cccc3)c3[s]3)c3c2)nc(cccc2)c2n1 Chemical compound c(cc1)ccc1-[n](c(cccc1)c1c1c2)c1cc(cc1c3c4cccc3)c2cc1[n]4-c1c(-c2ccc(c(cccc3)c3[s]3)c3c2)nc(cccc2)c2n1 IFJJAKZZOVOCAY-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
Definitions
- the present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
- OLED organic electroluminescent device
- Korean Patent Appl. Laid-Open Nos. 2010-0007780, 2014-0120090, 2011-0016033, and 2016-0007965 disclose a heteroaryl compound as a host compound comprised in an organic electroluminescent device, but do not specifically disclose a 24-membered heteroaryl compound containing a quinoxaline derivative.
- the objective of the present disclosure is to provide an organic electroluminescent compound suitable for producing an organic electroluminescent device having lower driving voltage, higher luminous efficiency, and/or improved lifespan properties.
- ring A represents a substituted or unsubstituted naphthalene
- R 1 and R 2 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6
- L 1 and L 2 each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
- Ar 1 represents hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
- Ar 2 represents any one selected from the following formulas:
- R 3 to R 13 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6
- a, b, c, f, and g represent an integer of 4; d represents an integer of 2; e represents an integer of 3; h and i represent an integer of 6; where each of R 1 , each of R 2 , each of R 3 , each of R 5 , each of R 6 , each of R 7 , each of R 8 , each of R 11 , and each of R 12 may be the same or different; and
- * represents the connecting site with L 2 .
- the organic electroluminescent compound according to the present disclosure can produce an organic electroluminescent device having lower driving voltage, higher luminous efficiency, and/or longer lifespan properties.
- organic electroluminescent compound in the present disclosure means a compound that may be used in an organic electroluminescent device, and may be comprised in any layer constituting an organic electroluminescent device, as necessary.
- organic electroluminescent material in the present disclosure means a material that may be used in an organic electroluminescent device, and may comprise at least one compound.
- the organic electroluminescent material may be comprised in any layer constituting an organic electroluminescent device, as necessary.
- the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.
- the organic electroluminescent material of the present disclosure may comprise at least one compound represented by formula 1.
- the compound represented by formula 1 may be comprised in a light-emitting layer, but is not limited thereto. When comprised in the light-emitting layer, the compound represented by formula 1 may be comprised as a host material.
- ring A represents a substituted or unsubstituted naphthalene; and according to one embodiment of the present disclosure, represents an unsubstituted naphthalene. Also, ring A may be represented by any one of the following formulas.
- R 14 each independently, represents hydrogen, deuterium, a halogen, a cyano, an unsubstituted (C1-C10)alkyl, an unsubstituted (C6-C18)aryl, or an unsubstituted (3- to 20-membered)heteroaryl.
- R 14 represents hydrogen.
- L 1 and L 2 each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; according to one embodiment of the present disclosure, represent a single bond, or a substituted or unsubstituted (C6-C25)arylene; and according to another embodiment of the present disclosure, represent a single bond, or an unsubstituted (C6-C18)arylene.
- L 1 may represent a single bond
- L 2 may represent a single bond, a phenylene, or a naphthylene.
- Ar 1 represents hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl.
- Ar 1 represents a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl.
- Ar 1 represents a substituted or unsubstituted (C6-C18)aryl.
- Ar 1 may represent a phenyl, a naphthyl, or a biphenyl.
- R 1 and R 2 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri
- R 1 and R 2 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl.
- R 1 and R 2 each independently, represent hydrogen, an unsubstituted (C1-C10)alkyl, an unsubstituted (C6-C18)aryl, or an unsubstituted (5- to 20-membered)heteroaryl.
- R 1 and R 2 represent hydrogen.
- Ar 2 represents any one selected from the following formulas.
- R 3 to R 13 each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstit
- R 3 to R 13 each independently, represent hydrogen, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl.
- R 3 to R 13 each independently, represent hydrogen, a (C6-C18)aryl unsubstituted or substituted with a (C1-C10)alkyl(s), or a (3- to 25-membered)heteroaryl unsubstituted or substituted with a (C6-C18)aryl(s).
- R 3 each independently, represents hydrogen, or an unsubstituted phenyl
- R 4 represents a phenyl, a naphthyl, a biphenyl, a dimethylfluorenyl, a naphthylphenyl, a phenylnaphthyl, a dibenzofuranyl, a dibenzothiophenyl, or a phenylcarbazolyl
- R 5 each independently, represents a phenyl
- R 6 to R 12 represent hydrogen
- R 9 , R 10 , and R 13 each independently, represent a phenyl, a naphthyl, or a biphenyl.
- a, b, c, f, and g represent an integer of 4; d represents an integer of 2; e represents an integer of 3; h and i represent an integer of 6; where each of R 1 , each of R 2 , each of R 3 , each of R 5 , each of R 6 , each of R 7 , each of R 8 , each of R 11 , and each of R 12 may be the same or different; and * represents the connecting site with L 2 .
- the compound represented by formula 1 may be a compound represented by any one of the following formulas 2-1 to 2-4.
- L 1 , L 2 , Ar 1 , Ar 2 , R 1 , R 2 , a and b are as defined in formula 1.
- (C1-C30)alkyl is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10.
- the above alkyl may include methyl, ethyl, n -propyl, iso -propyl, n -butyl, iso -butyl, tert -butyl, etc.
- (C2-C30)alkenyl is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10.
- the above alkenyl may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
- (C2-C30)alkynyl is meant to be a linear or branched alkynyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10.
- the above alkynyl may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
- (C3-C30)cycloalkyl is meant to be a mono- or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, in which the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7.
- the above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
- (3- to 7-membered)heterocycloalkyl is meant to be a cycloalkyl having 3 to 7, preferably 5 to 7, ring backbone atoms, and including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably the group consisting of O, S, and N.
- the above heterocycloalkyl may include tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.
- (C6-C30)aryl(ene) is meant to be a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, in which the number of the ring backbone carbon atoms is preferably 6 to 25, more preferably 6 to 18.
- the above aryl may be partially saturated, and may comprise a spiro structure.
- the above aryl may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, etc.
- the term "(3- to 30-membered)heteroaryl(ene)” is meant to be an aryl group having 3 to 30 ring backbone atoms, and including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P.
- the above heteroaryl may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and may comprise a spiro structure.
- the above heteroaryl may include a monocyclic ring-type heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindo
- substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or another functional group, i.e., a substituent.
- the substituents are at least one selected from the group consisting of a (C1-C20)alkyl, a (C6-C25)aryl and a (5- to 25-membered)heteroaryl.
- the substituents, each independently are at least one selected from the group consisting of a (C1-C10)alkyl and a (C6-C18)aryl.
- the substituents, each independently may be at least one selected from the group consisting of a methyl, a phenyl, and a naphthyl.
- the ring may be a substituted or unsubstituted mono- or polycyclic (3- to 30-membered) alicyclic or aromatic ring, or the combination thereof, in which the formed ring may contain at least one heteroatom selected from nitrogen, oxygen, and sulfur.
- the compound represented by formula 1 includes the following compounds, but is not limited thereto.
- the compound of formula 1 according to the present disclosure may be prepared by a synthetic method known to one skilled in the art, and for example, as shown in the following reaction scheme, but is not limited thereto.
- L 1 , L 2 , Ar 1 , Ar 2 , R 1 , R 2 , a, and b are as defined in formula 1; and Hal is a halogen atom.
- the present disclosure may provide an organic electroluminescent material comprising the organic electroluminescent compound represented by formula 1, and an organic electroluminescent device comprising the organic electroluminescent material.
- the organic electroluminescent material may consist of only the organic electroluminescent compounds of the present disclosure, and may further include conventional compounds included in the organic electroluminescent material.
- the organic electroluminescent device comprises a first electrode; a second electrode; and at least one organic layer between the first and second electrodes.
- the organic layer may comprise at least one organic electroluminescent compound represented by formula 1.
- the organic layer may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
- the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal.
- the organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, an electron blocking layer, and an electron buffer layer.
- the organic electroluminescent compound represented by formula 1 of the present disclosure may be comprised in a light-emitting layer.
- the organic electroluminescent compound represented by formula 1 of the present disclosure may be comprised as a host material.
- the light-emitting layer may further comprise at least one dopant.
- the light-emitting layer may further comprise a compound(s) other than the organic electroluminescent compound represented by formula 1 of the present disclosure (first host material) as a second host material.
- the weight ratio between the first host material and the second host material is in the range of 1:99 to 99:1.
- the second host material may be any of the known phosphorescent hosts, but is not limited thereto.
- the organic electroluminescent compound of the present disclosure can be used to produce a display system or a lighting system. Specifically, it is possible to produce a display system, e.g., a display system for smartphones, tablets, notebooks, PCs, TVs, or cars, or a lighting system, e.g., an outdoor or indoor lighting system, by using the organic electroluminescent device comprising the organic electroluminescent compound of the present disclosure.
- a display system e.g., a display system for smartphones, tablets, notebooks, PCs, TVs, or cars
- a lighting system e.g., an outdoor or indoor lighting system
- OLED organic electroluminescent device
- An OLED according to the present disclosure was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone, ethanol and distilled water, sequentially, and then was stored in isopropanol.
- the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus.
- Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and the pressure in the chamber of the apparatus was then controlled to 10 -6 torr.
- compound HI-2 was introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer.
- Compound HT-1 was then introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer.
- Compound HT-2 was then introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer.
- a light-emitting layer was formed thereon as follows: The host material shown in Table 1 was introduced into one cell of the vacuum vapor depositiong apparatus as a host, and compound D-1 was introduced into another cell as a dopant.
- the two materials were evaporated at different rates and the dopant was deposited in a doping amount of 3 wt% based on the total amount of the hosts and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
- compound ET-1 and compound EI-1 were evaporated at a rate of 1:1 in two other cells to deposit an electron transport layer having a thickness of 35 nm on the light-emitting layer.
- an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus.
- an OLED was produced.
- Comparative Example 1 Producing an OLED comprising a comparative
- An OLED was produced in the same manner as in Device Example 1, except that the following compound A was used as a host of the light-emitting layer.
- an OLED comprising the organic electroluminescent compound of the present disclosure has lower driving voltage, higher luminous efficiency, and/or longer lifespan properties as compared with an OLED comprising a conventional compound.
- the compounds listed in Table 2 as host materials according to the present disclosure have high HOMO energy values due to naphthalene. Generally, the compounds tend to have higher HOMO energy value, the greater the hole mobility, which contributes to lowering the driving voltage of the OLED. It is understood that substituting quinoxaline instead of triazine in this HOMO moiety results in a lower band gap of the triplet energy, since quinoxaline has a LUMO energy value and triplet energy value lower than triazine. As a result, the compound of the present disclosure has a more suitable energy value for the red host, thereby improving electron mobility and charge balance.
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Abstract
The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound of the present disclosure, it is possible to provide an organic electroluminescent device having lower driving voltage, higher luminous efficiency, and/or improved lifespan properties.
Description
The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
A small molecular green organic electroluminescent device (OLED) was first developed by Tang, et al., of Eastman Kodak in 1987 by using TPD/Alq3 bi-layer consisting of a light-emitting layer and a charge transport layer. Thereafter, the development of OLEDs was rapidly effected and OLEDs have been commercialized. At present, OLEDs primarily use phosphorescent materials having excellent luminous efficiency in panel implementation. Also, an OLED having low driving voltage and high luminous efficiency is required for prolonged use and high resolution of a display. Thus, various materials used for the organic layer of the organic electroluminescent device have been developed in order to improve luminous efficiency, driving voltage, or lifespan.
Korean Patent Appl. Laid-Open Nos. 2010-0007780, 2014-0120090, 2011-0016033, and 2016-0007965 disclose a heteroaryl compound as a host compound comprised in an organic electroluminescent device, but do not specifically disclose a 24-membered heteroaryl compound containing a quinoxaline derivative.
The objective of the present disclosure is to provide an organic electroluminescent compound suitable for producing an organic electroluminescent device having lower driving voltage, higher luminous efficiency, and/or improved lifespan properties.
The present inventors found that the above objective can be achieved by an organic electroluminescent compound represented by the following formula 1:
wherein
ring A represents a substituted or unsubstituted naphthalene;
R1 and R2, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or two or more R1’s may be linked to each other to form a ring(s); or two or more R2’s may be linked to each other to form a ring(s);
L1 and L2, each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
Ar1 represents hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
Ar2 represents any one selected from the following formulas:
wherein
R3 to R13, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino;
a, b, c, f, and g represent an integer of 4; d represents an integer of 2; e represents an integer of 3; h and i represent an integer of 6; where each of R1, each of R2, each of R3, each of R5, each of R6, each of R7, each of R8, each of R11, and each of R12 may be the same or different; and
* represents the connecting site with L2.
The organic electroluminescent compound according to the present disclosure can produce an organic electroluminescent device having lower driving voltage, higher luminous efficiency, and/or longer lifespan properties.
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the disclosure, and is not meant in any way to restrict the scope of the disclosure.
The term "organic electroluminescent compound" in the present disclosure means a compound that may be used in an organic electroluminescent device, and may be comprised in any layer constituting an organic electroluminescent device, as necessary.
The term "organic electroluminescent material" in the present disclosure means a material that may be used in an organic electroluminescent device, and may comprise at least one compound. The organic electroluminescent material may be comprised in any layer constituting an organic electroluminescent device, as necessary. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc.
The organic electroluminescent material of the present disclosure may comprise at least one compound represented by formula 1. The compound represented by formula 1 may be comprised in a light-emitting layer, but is not limited thereto. When comprised in the light-emitting layer, the compound represented by formula 1 may be comprised as a host material.
Hereinafter, the compound represented by formula 1 will be described in more detail.
In formula 1, ring A represents a substituted or unsubstituted naphthalene; and according to one embodiment of the present disclosure, represents an unsubstituted naphthalene. Also, ring A may be represented by any one of the following formulas.
In the formulas above, j represents an integer of 4; and R14, each independently, represents hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl, where each of R14 may be the same or different. According to one embodiment of the present disclosure, R14, each independently, represents hydrogen, deuterium, a halogen, a cyano, an unsubstituted (C1-C10)alkyl, an unsubstituted (C6-C18)aryl, or an unsubstituted (3- to 20-membered)heteroaryl. For example, R14 represents hydrogen.
In formula 1, L1 and L2, each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; according to one embodiment of the present disclosure, represent a single bond, or a substituted or unsubstituted (C6-C25)arylene; and according to another embodiment of the present disclosure, represent a single bond, or an unsubstituted (C6-C18)arylene. For example, L1 may represent a single bond, and L2 may represent a single bond, a phenylene, or a naphthylene.
In formula 1, Ar1 represents hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl. According to one embodiment of the present disclosure, Ar1 represents a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl. According to another embodiment of the present disclosure, Ar1 represents a substituted or unsubstituted (C6-C18)aryl. For example, Ar1 may represent a phenyl, a naphthyl, or a biphenyl.
In formula 1, R1 and R2, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or two or more R1’s may be linked to each other to form a ring(s); or two or more R2’s may be linked to each other to form a ring(s). According to one embodiment of the present disclosure, R1 and R2, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl. According to another embodiment of the present disclosure, R1 and R2, each independently, represent hydrogen, an unsubstituted (C1-C10)alkyl, an unsubstituted (C6-C18)aryl, or an unsubstituted (5- to 20-membered)heteroaryl. For example, R1 and R2 represent hydrogen.
In formula 1, Ar2 represents any one selected from the following formulas.
In the formulas above, R3 to R13, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino. According to one embodiment of the present disclosure, R3 to R13, each independently, represent hydrogen, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl. According to another embodiment of the present disclosure, R3 to R13, each independently, represent hydrogen, a (C6-C18)aryl unsubstituted or substituted with a (C1-C10)alkyl(s), or a (3- to 25-membered)heteroaryl unsubstituted or substituted with a (C6-C18)aryl(s). For example, R3, each independently, represents hydrogen, or an unsubstituted phenyl; R4 represents a phenyl, a naphthyl, a biphenyl, a dimethylfluorenyl, a naphthylphenyl, a phenylnaphthyl, a dibenzofuranyl, a dibenzothiophenyl, or a phenylcarbazolyl; R5, each independently, represents a phenyl; R6 to R12 represent hydrogen; and R9, R10, and R13, each independently, represent a phenyl, a naphthyl, or a biphenyl.
In the formulas above, a, b, c, f, and g represent an integer of 4; d represents an integer of 2; e represents an integer of 3; h and i represent an integer of 6; where each of R1, each of R2, each of R3, each of R5, each of R6, each of R7, each of R8, each of R11, and each of R12 may be the same or different; and * represents the connecting site with L2.
According to one embodiment of the present disclosure, the compound represented by formula 1 may be a compound represented by any one of the following formulas 2-1 to 2-4.
In formulas 2-1 to 2-4, L1, L2, Ar1, Ar2, R1, R2, a and b are as defined in formula 1.
Herein, the term "(C1-C30)alkyl" is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above alkyl may include methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, etc. The term "(C2-C30)alkenyl" is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above alkenyl may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. The term "(C2-C30)alkynyl" is meant to be a linear or branched alkynyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above alkynyl may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc. The term "(C3-C30)cycloalkyl" is meant to be a mono- or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, in which the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term "(3- to 7-membered)heterocycloalkyl" is meant to be a cycloalkyl having 3 to 7, preferably 5 to 7, ring backbone atoms, and including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably the group consisting of O, S, and N. The above heterocycloalkyl may include tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. The term "(C6-C30)aryl(ene)" is meant to be a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, in which the number of the ring backbone carbon atoms is preferably 6 to 25, more preferably 6 to 18. The above aryl may be partially saturated, and may comprise a spiro structure. The above aryl may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, etc. Herein, the term "(3- to 30-membered)heteroaryl(ene)" is meant to be an aryl group having 3 to 30 ring backbone atoms, and including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The above heteroaryl may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and may comprise a spiro structure. The above heteroaryl may include a monocyclic ring-type heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, benzoquinazolinyl, quinoxalinyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, etc. "Halogen" includes F, Cl, Br, and I.
Herein, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced with another atom or another functional group, i.e., a substituent. The substituents of the substituted naphthalene, the substituted (C1-C30)alkyl, the substituted (C6-C30)aryl(ene), the substituted (3- to 30-membered)heteroaryl(ene), the substituted (C3-C30)cycloalkyl, the substituted (C1-C30)alkoxy, the substituted tri(C1-C30)alkylsilyl, the substituted di(C1-C30)alkyl(C6-C30)arylsilyl, the substituted (C1-C30)alkyldi(C6-C30)arylsilyl, the substituted tri(C6-C30)arylsilyl, the substituted mono- or di- (C1-C30)alkylamino, the substituted mono- or di- (C6-C30)arylamino, and the substituted (C1-C30)alkyl(C6-C30)arylamino in ring A, L1, L2, Ar1, and R1 to R14, each independently, are at least one selected from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30)alkenyl; a (C2-C30)alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a (C3-C30)cycloalkenyl; a (3- to 7-membered)heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl(s); a (C6-C30)aryl unsubstituted or substituted with a (3- to 30-membered)heteroaryl(s); a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; an amino; a mono- or di- (C1-C30)alkylamino; a mono- or di- (C6-C30)arylamino unsubstituted or substituted with a (C1-C30)alkyl(s); a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl. According to one embodiment of the present disclosure, the substituents, each independently, are at least one selected from the group consisting of a (C1-C20)alkyl, a (C6-C25)aryl and a (5- to 25-membered)heteroaryl. According to another embodiment of the present disclosure, the substituents, each independently, are at least one selected from the group consisting of a (C1-C10)alkyl and a (C6-C18)aryl. For example, the substituents, each independently, may be at least one selected from the group consisting of a methyl, a phenyl, and a naphthyl.
In the formulas of the present disclosure, if adjacent substituents are linked to each other to form a ring, the ring may be a substituted or unsubstituted mono- or polycyclic (3- to 30-membered) alicyclic or aromatic ring, or the combination thereof, in which the formed ring may contain at least one heteroatom selected from nitrogen, oxygen, and sulfur.
The compound represented by formula 1 includes the following compounds, but is not limited thereto.
The compound of formula 1 according to the present disclosure may be prepared by a synthetic method known to one skilled in the art, and for example, as shown in the following reaction scheme, but is not limited thereto.
[Reaction Scheme 1]
In reaction scheme 1, L1, L2, Ar1, Ar2, R1, R2, a, and b are as defined in formula 1; and Hal is a halogen atom.
In addition, the present disclosure may provide an organic electroluminescent material comprising the organic electroluminescent compound represented by formula 1, and an organic electroluminescent device comprising the organic electroluminescent material. The organic electroluminescent material may consist of only the organic electroluminescent compounds of the present disclosure, and may further include conventional compounds included in the organic electroluminescent material.
Meanwhile, the organic electroluminescent device according to the present disclosure comprises a first electrode; a second electrode; and at least one organic layer between the first and second electrodes. The organic layer may comprise at least one organic electroluminescent compound represented by formula 1. Also, the organic layer may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds. Further, the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4th period, transition metals of the 5th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal.
One of the first and second electrodes may be an anode, and the other may be a cathode. The organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron injection layer, an interlayer, a hole blocking layer, an electron blocking layer, and an electron buffer layer.
The organic electroluminescent compound represented by formula 1 of the present disclosure may be comprised in a light-emitting layer. When used in the light-emitting layer, the organic electroluminescent compound represented by formula 1 of the present disclosure may be comprised as a host material. Preferably, the light-emitting layer may further comprise at least one dopant. If necessary, the light-emitting layer may further comprise a compound(s) other than the organic electroluminescent compound represented by formula 1 of the present disclosure (first host material) as a second host material. The weight ratio between the first host material and the second host material is in the range of 1:99 to 99:1. The second host material may be any of the known phosphorescent hosts, but is not limited thereto.
The organic electroluminescent compound of the present disclosure can be used to produce a display system or a lighting system. Specifically, it is possible to produce a display system, e.g., a display system for smartphones, tablets, notebooks, PCs, TVs, or cars, or a lighting system, e.g., an outdoor or indoor lighting system, by using the organic electroluminescent device comprising the organic electroluminescent compound of the present disclosure.
Hereinafter, the preparation method of the compound of the present disclosure, and the properties thereof will be explained in detail with reference to the representative compounds of the present disclosure. However, the present disclosure is not limited to the following examples.
Example 1: Preparation of compound H-51
Synthesis of compound
1-1
In a flask, 40 g of 1,5-dibromonaphthalene (140 mmol), 78.14 g of bis(pinacolate)diboron (308 mmol), 3.9 g of bis(triphenylphosphine)palladium(II) dichloride (6 mmol), and 60 g of potassium acetate (615 mmol) were dissolved in 900 mL of 1,4-dioxane, and the mixture was refluxed for 3 hours at 120℃. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was separated by column chromatography to obtain 38 g of compound 1-1 (71%).
Synthesis of compound
1-2
In a flask, 38 g of compound 1-1 (100 mmol), 60.6 g of 1-bromo-2-nitrobenzene (300 mmol), 23.1 g of tetrakis(triphenylphosphine)palladium(0) (20 mmol), and 53 g of sodium carbonate (500 mmol) were dissolved in 500 mL of toluene, 250 mL of ethanol, and 250 mL of water, and the mixture was refluxed for 3 hours at 120℃. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was separated by column chromatography to obtain 29.6 g of compound 1-2 (79.9%).
Synthesis of compound
1-3
In a flask, 30 g of compound 1-2 (81 mmol), and 42.49 g of triphenylphosphine (162 mmol) were dissolved in 405 mL of dichlorobenzene, and the mixture was refluxed for 24 hours at 200℃. After completion of the reaction, the solvent was removed by vacuum distillation. The residue was separated by column chromatography to obtain 13.6 g of compound 1-3 (49%).
Synthesis of compound
1-4
In a flask, 13.6 g of compound 1-3 (40 mmol), 12.3 g of iodobenzene (60 mmol), 5.3 g of copper iodide (28 mmol), 6.8 g of 1,2-diaminocyclohexane (60 mmol), and 39.3 g of cesium carbonate (121 mmol) were dissolved in 200 mL of xylene, and the mixture was refluxed for 3 hours at 180℃. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was separated by column chromatography to obtain 12 g of compound 1-4 (75%).
Synthesis of compound
1-5
In a flask, 12 g of compound 1-4 (48 mmol), and 30.38 g of triphenylphosphine (116 mmol) were dissolved in 240 mL of dichlorobenzene, and the mixture was refluxed for 24 hours at 200℃. After completion of the reaction, the solvent was removed by vacuum distillation. The residue was separated by column chromatography to obtain 9 g of compound 1-5 (82%).
Synthesis of compound
H-51
In a flask, 5 g of compound 1-5 (13 mmol), 3.4 g of 2-chloro-3-phenylquinoxaline (14 mmol), 5.4 g of potassium carbonate (39 mmol), and 80 mg of dimethylaminopyridine (0.654 mmol) were dissolved in 65 mL of dimethyl formamide, and the mixture was refluxed for 24 hours at 180℃. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was separated by column chromatography to obtain 4.2 g of compound H-51 (54%).
Example 2: Preparation of compound H-52
In a flask, 3.8 g of compound 1-5 (10 mmol), 3.178 g of 2-chloro-3-naphthylquinoxaline (11 mmol), 4.1 g of potassium carbonate (30 mmol), and 61 mg of dimethylaminopyridine (0.497 mmol) were dissolved in 50 mL of dimethyl formamide, and the mixture was refluxed for 24 hours at 180℃. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 1.5 g of compound H-52 (23.7%).
Example 3: Preparation of compound H-507
Synthesis of compound
3-1
In a flask, 11 g of compound 1-3 (33 mmol), 13.6 g of iodobiphenyl (49 mmol), 4.3 g of copper iodide (23 mmol), 5.8 mL of 1,2-diaminocyclohexane (49 mmol), and 31.7 g of cesium carbonate (99 mmol) were dissolved in 162 mL of xylene, and the mixture was refluxed for 3 hours at 180℃. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 15 g of compound 3-1 (94%).
Synthesis of compound
3-2
In a flask, 15 g of compound 3-1 (31 mmol), and 19.2 g of triphenylphosphine (73 mmol) were dissolved in 152 mL of dichlorobenzene, and the mixture was refluxed for 24 hours at 200℃. After completion of the reaction, the solvent was removed by vacuum distillation. The residue was separated by column chromatography to obtain 11 g of compound 3-2 (78%).
Synthesis of compound
H-507
In a flask, 6 g of compound 3-2 (13 mmol), 3.4 g of 2-chloro-3-phenylquinoxaline (14 mmol), 5.4 g of potassium carbonate (39 mmol), and 799 mg of dimethylaminopyridine (7 mmol) were dissolved in 64 mL of dimethylformamide, and the mixture was refluxed for 24 hours at 180℃. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 1.3 g of compound H-507 (15%).
Example 4: Preparation of compound H-269
Synthesis of compound
4-1
In a flask, 49 g of compound 1-3 (144.8 mmol), 55.1 g of 2-bromo naphthalene (217 mmol), 27.5 g of copper iodide (101.3 mmol), 26 mL of 1,2-diaminocyclohexane (217.2 mmol), and 141 g of cesium carbonate (424 mmol) were dissolved in 724 mL of xylene, and the mixture was refluxed for 3 hours at 180℃. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 44.7 g of compound 4-1 (66.7%).
Synthesis of compound
4-2
In a flask, 44.7 g of compound 4-1 (96.2 mmol), and 60.5 g of triphenylphosphine (230 mmol) were dissolved in 481 mL of dichlorobenzene, and the mixture was refluxed for 24 hours at 200℃. After completion of the reaction, the solvent was removed by vacuum distillation. The residue was separated by column chromatography to obtain 25 g of compound 4-2 (61%).
Synthesis of compound
H-269
In a flask, 25 g of compound 4-2 (57.8 mmol), 16.6 g of 2-chloro-3-phenylquinoxaline (69.4 mmol), 24 g of potassium carbonate (173 mmol), and 353 mg of dimethylaminopyridine (2.89 mmol) were dissolved in 385 mL of dimethylformamide, and the mixture was refluxed for 24 hours at 180℃. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 16 g of compound H-269 (43%).
Example 5: Preparation of compound H-101
Synthesis of compound
5-1
In a flask, 51.6 g of 2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene (135.7 mmol), 82.2 g of 1-bromo-2-nitrobenzene (407.2 mmol), 31.4 g of tetrakis(triphenylphosphine)palladium(0) (27.1 mmol), and 93.8 g of potassium carbonate (678.5 mmol) were dissolved in 400 mL of toluene, 340 mL of ethanol, and 340 mL of water, and the mixture was refluxed at 120℃. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 42.6 g of compound 5-1 (84%).
Synthesis of compound
5-2
In a flask, 42.6 g of compound 5-1 (115 mmol), and 60.3 g of triphenylphosphine (230 mmol) were dissolved in 575 mL of dichlorobenzene, and the mixture was refluxed for 24 hours at 200℃. After completion of the reaction, the solvent was removed by vacuum distillation. The residue was separated by column chromatography to obtain 20 g of compound 5-2 (51%).
Synthesis of compound
5-3
In a flask, 8.4 g of compound 5-2 (24.8 mmol), 5.5 mL of iodobenzene (49.6 mmol), 1.1 g of tris(dibenzylideneacetone)dipalladium(0) (1.24 mmol), 1.2 mL of tri-tert-butylphosphine (2.48 mmol), and 7.15 g of sodium-tert-butoxide (74.4 mmol) were dissolved in 124 mL of xylene, and the mixture was refluxed for 3 hours at 180℃. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 7.2 g of compound 5-3 (70.5%).
Synthesis of compound
5-4
In a flask, 7.2 g of compound 5-3 (17.3 mmol), and 10.9 g of triphenylphosphine (41.6 mmol) were dissolved in 87 mL of dichlorobenzene, and the mixture was refluxed for 24 hours at 200℃. After completion of the reaction, the solvent was removed by vacuum distillation. The residue was separated by column chromatography to obtain 4.5 g of compound 5-4 (66%).
Synthesis of compound
H-101
In a flask, 4.5 g of compound 5-4 (11.7 mmol), 16 g of 2-chloro-3-phenylquinoxaline (35.3 mmol), 40.4 g of cesium carbonate (140.4 mmol), and 3 g of dimethylaminopyridine (23.4 mmol) were dissolved in 110 mL of dimethylformamide, and the mixture was refluxed for 24 hours at 230℃. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 1 g of compound H-101 (14%).
Example 6: Preparation of compound H-169
Synthesis of compound
6-1
In a flask, 7.5 g of 1-bromo-7-phenyl-7H benzo[c]carbazole (20 mmol), 10 g of nitrophenylboronic acid (60 mmol), 2.32 g of tetrakis(triphenylphosphine)palladium(0) (2 mmol), and 8.3 g of potassium carbonate (60 mmol) were dissolved in 80 mL of tetrahydrofuran and 20 mL of water, and the mixture was refluxed for 24 hours at 120℃. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was separated by column chromatography to obtain 3 g of compound 6-1 (36%).
Synthesis of compound
6-2
In a flask, 5.5 g of compound 6-1 (13 mmol), and 8.7 g of triphenylphosphine (33 mmol) were dissolved in 70 mL of dichlorobenzene, and the mixture was refluxed at 180℃. After completion of the reaction, the solvent was removed by vacuum distillation. The residue was separated by column chromatography to obtain 2 g of compound 6-2 (40%).
Synthesis of compound
H-169
In a flask, 2 g of compound 6-2 (5.23 mmol), 1.38 g of 2-chloro-3-phenylquinoxaline (5.75 mmol), 1.7 g of cesium carbonate (5.23 mmol), and 320 mg of dimethylaminopyridine (2.62 mmol) were dissolved in 20 mL of dimethylformamide, and the mixture was refluxed for 24 hours at 180℃. After completion of the reaction, the organic layer was extracted with ethyl acetate, and the residual moisture was removed by using magnesium sulfate. The residue was dried and separated by column chromatography to obtain 1.1 g of compound H-169 (35.8%).
Hereinafter, the characteristics of the organic electroluminescent device (OLED) comprising the organic electroluminescent compound of the present disclosure will be described in order to understand the present disclosure in detail.
Device Examples 1 to 4: Producing an OLED comprising a compound
according to the present disclosure as a host
An OLED according to the present disclosure was produced as follows: A transparent electrode indium tin oxide (ITO) thin film (10 Ω/sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone, ethanol and distilled water, sequentially, and then was stored in isopropanol. The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and the pressure in the chamber of the apparatus was then controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the above-introduced material, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate. Next, compound HI-2 was introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer. Compound HT-1 was then introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer. Compound HT-2 was then introduced into another cell of the vacuum vapor deposition apparatus and was evaporated by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After forming the hole injection layers and the hole transport layers, a light-emitting layer was formed thereon as follows: The host material shown in Table 1 was introduced into one cell of the vacuum vapor depositiong apparatus as a host, and compound D-1 was introduced into another cell as a dopant. The two materials were evaporated at different rates and the dopant was deposited in a doping amount of 3 wt% based on the total amount of the hosts and dopant to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer. Next, compound ET-1 and compound EI-1 were evaporated at a rate of 1:1 in two other cells to deposit an electron transport layer having a thickness of 35 nm on the light-emitting layer. After depositing compound EI-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED was produced.
Comparative Example 1: Producing an OLED comprising a comparative
compound as a host
An OLED was produced in the same manner as in Device Example 1, except that the following compound A was used as a host of the light-emitting layer.
The compounds used in the Device Examples and the Comparative Example are as follows.
The results of the driving voltage and the luminous efficiency at a luminance of 1,000 nits, and the lifespan (the time taken to reduce the initial luminance of 100% to a luminance of 90% at a constant current in a luminance of 5,000 nits) of the OLEDs produced in the Device Examples and the Comparative Example, are shown in the following Table 1.
The physical properties of the host materials used in the Device Examples and the Comparative Example are shown in the following Table 2.
From the Device Examples and the Comparative Example, it can be confirmed that an OLED comprising the organic electroluminescent compound of the present disclosure has lower driving voltage, higher luminous efficiency, and/or longer lifespan properties as compared with an OLED comprising a conventional compound.
Specifically, the compounds listed in Table 2 as host materials according to the present disclosure have high HOMO energy values due to naphthalene. Generally, the compounds tend to have higher HOMO energy value, the greater the hole mobility, which contributes to lowering the driving voltage of the OLED. It is understood that substituting quinoxaline instead of triazine in this HOMO moiety results in a lower band gap of the triplet energy, since quinoxaline has a LUMO energy value and triplet energy value lower than triazine. As a result, the compound of the present disclosure has a more suitable energy value for the red host, thereby improving electron mobility and charge balance.
Claims (8)
- An organic electroluminescent compound represented by the following formula 1:
whereinring A represents a substituted or unsubstituted naphthalene;R1 and R2, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or two or more R1’s may be linked to each other to form a ring(s); or two or more R2’s may be linked to each other to form a ring(s);L1 and L2, each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;Ar1 represents hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;Ar2 represents any one selected from the following formulas:
whereinR3 to R13, each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino;a, b, c, f, and g represent an integer of 4; d represents an integer of 2; e represents an integer of 3; h and i represent an integer of 6; where each of R1, each of R2, each of R3, each of R5, each of R6, each of R7, each of R8, each of R11, and each of R12 may be the same or different; and* represents the connecting site with L2. - The organic electroluminescent compound according to claim 1, wherein ring A represents any one of the following formulas:
whereinj represents an integer of 4; andR14, each independently, represents hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl, where each of R14 may be the same or different. - The organic electroluminescent compound according to claim 1, wherein formula 1 is represented by any one of the following formulas 2-1 to 2-4:
whereinL1, L2, Ar1, Ar2, R1, R2, a, and b are as defined in claim 1. - The organic electroluminescent compound according to claim 1, wherein the substituents of the substituted naphthalene, the substituted (C1-C30)alkyl, the substituted (C6-C30)aryl(ene), the substituted (3- to 30-membered)heteroaryl(ene), the substituted (C3-C30)cycloalkyl, the substituted (C1-C30)alkoxy, the substituted tri(C1-C30)alkylsilyl, the substituted di(C1-C30)alkyl(C6-C30)arylsilyl, the substituted (C1-C30)alkyldi(C6-C30)arylsilyl, the substituted tri(C6-C30)arylsilyl, the substituted mono- or di- (C1-C30)alkylamino, the substituted mono- or di- (C6-C30)arylamino, and the substituted (C1-C30)alkyl(C6-C30)arylamino in ring A, L1, L2, Ar1, and R1 to R13, each independently, are at least one selected from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30)alkenyl; a (C2-C30)alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a (C3-C30)cycloalkenyl; a (3- to 7-membered)heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a (3- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl; a (C6-C30)aryl unsubstituted or substituted with a (3- to 30-membered)heteroaryl; a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; an amino; a mono- or di- (C1-C30)alkylamino; a mono- or di- (C6-C30)arylamino unsubstituted or substituted with a (C1-C30)alkyl; a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl.
- The organic electroluminescent compound according to claim 1, wherein the compound represented by the formula 1 is any one selected from the group consisting of the following compounds:
- An organic electroluminescent material comprising the organic electroluminescent compound according to claim 1.
- An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.
- The organic electroluminescent device according to claim 7, wherein the organic electroluminescent compound is comprised in a light-emitting layer.
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| KR1020190033691A KR20190115412A (en) | 2018-04-02 | 2019-03-25 | Organic electroluminescent compound and organic electroluminescent device comprising the same |
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