WO2019017697A1 - Organic electroluminescent compound and organic electroluminescent device comprising the same - Google Patents

Organic electroluminescent compound and organic electroluminescent device comprising the same Download PDF

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Publication number
WO2019017697A1
WO2019017697A1 PCT/KR2018/008140 KR2018008140W WO2019017697A1 WO 2019017697 A1 WO2019017697 A1 WO 2019017697A1 KR 2018008140 W KR2018008140 W KR 2018008140W WO 2019017697 A1 WO2019017697 A1 WO 2019017697A1
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Prior art keywords
substituted
unsubstituted
alkyl
aryl
organic electroluminescent
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PCT/KR2018/008140
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French (fr)
Inventor
Hyun Kim
Doo-Hyeon Moon
Sang-Hee Cho
Sung-Wook Cho
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DuPont Specialty Materials Korea Ltd
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Rohm and Haas Electronic Materials Korea Ltd
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Priority claimed from KR1020180067248A external-priority patent/KR102740675B1/en
Application filed by Rohm and Haas Electronic Materials Korea Ltd filed Critical Rohm and Haas Electronic Materials Korea Ltd
Priority to US16/630,871 priority Critical patent/US10991889B2/en
Priority to CN201880046816.4A priority patent/CN110914379B/en
Publication of WO2019017697A1 publication Critical patent/WO2019017697A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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 materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • 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
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers

Definitions

  • the present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
  • An electroluminescent (EL) device is a self-light-emitting device with the advantages of providing a wider viewing angle, a greater contrast ratio, and a faster response time.
  • the first organic EL device was developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer ( see Appl. Phys. Lett. 51, 913, 1987).
  • An organic EL device changes electric energy into light by the injection of a charge into an organic light-emitting material, and commonly comprises an anode, a cathode, and an organic layer formed between the two electrodes.
  • the organic layer of the organic EL device may be composed of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (containing host and dopant materials), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc.; the materials used in the organic layer can be classified into a hole injection material, a hole transport 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., depending on functions.
  • the organic EL device In the organic EL device, holes from an anode and electrons from a cathode are injected into a light-emitting layer by electric voltage, and an exciton having high energy is produced by the recombination of the holes and electrons.
  • the organic light-emitting compound moves into an excited state by the energy and emits light from energy when the organic light-emitting compound returns to the ground state from the excited state.
  • an electron transport material actively transports electrons from a cathode to a light-emitting layer and inhibits transport of holes which are not recombined in the light-emitting layer to increase recombination opportunity of holes and electrons in the light-emitting layer.
  • electron-affinitive materials are used as an electron transport material.
  • Organic metal complexes having light-emitting function such as Alq 3 have been conventionally used as an electron transport material.
  • Alq 3 also has a limitation in providing an organic electroluminescent device having sufficiently satisfactory performance, thus, there is a demand for an electron transport material having improved performance capable of replacing Alq 3 . Therefore, new electron transport materials have been required, which do not have the above problems, are highly electron-affinitive, and quickly transport electrons in organic EL devices to provide organic EL devices having high luminous efficiency.
  • the electron buffer layer is a layer for solving the problem of a change in luminance caused by the change of a current characteristic of the device when exposed to a high temperature during a process of producing a panel.
  • the characteristic of the compound comprised in the electron buffer layer is important.
  • the objective of the present disclosure is to provide an organic electroluminescent compound which is effective for manufacturing an organic electroluminescent device having low driving voltage, high efficiency and/or excellent color coordinates.
  • the present inventors found that the compounds are stabilized against stress such as high temperature when the weak positions of quinoline, which are the second and the fourth carbon positions thereof, are protected.
  • the organic electroluminescent device comprising the indenoquinoline derivative which is substituted with e.g., aryl and/or heteroaryl at the second and the fourth carbon positions on the basis of quinoline has a higher luminous efficiency as well as a lower driving voltage than the indenoquinoline derivative having only one substituent in the quinoline moiety, and reached the present invention.
  • the present inventors found the aforementioned objective can be achieved by the organic electroluminescent compound represented by the following formula 1, and completed the present invention.
  • R 1 to R 3 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, provided that at least two of R 1 to R 3 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • a and b, or b and c, or c and d of formula 1 are combined with * of formula 2 to form a ring, wherein B 1 and B 2 are bonded at the positions not bonded to * of formula 2 among a to d, regardless of the sequence;
  • B 1 and B 2 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- 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)aryl
  • Ar 1 and Ar 2 each independently represent halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; or may be linked to an adjacent substituent to form a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic or aromatic ring, or a combination thereof;
  • R 11 to R 14 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- 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)aryl
  • the organic electroluminescent device having a low driving voltage, a high luminous efficiency and/or excellent color coordinates is provided.
  • 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, if 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. If necessary, the organic electroluminescent material may be comprised in any layer constituting an organic electroluminescent device.
  • 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, or an electron injection material.
  • An organic electroluminescent material of the present disclosure comprises at least one compound represented by formula 1 above.
  • the compound of formula 1 may be comprised in at least one layer, which consists of the organic electroluminescent device; and may be in the electron buffer layer and/or the electron transport layer, but not limited thereto; may be included as an electron buffer material when included in the electron buffer layer and may be included as an electron transport material when included in the electron transport layer.
  • the compound represented by formula 1 may be represented by any one of the following formulae 3 to 8.
  • R 1 to R 3 , B 1 , B 2 , Ar 1 , Ar 2 , and R 11 to R 14 are as defined in formula 1.
  • R 1 to R 3 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, provided that at least two of R 1 to R 3 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl.
  • R 1 and R 3 each independently represent a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl, and R 2 represents hydrogen.
  • R 1 and R 3 each independently represent a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl, and wherein the substituents of the substituted aryl each independently represent (C6-C15)aryl-substituted or unsubstituted (5- to 25-membered)heteroaryl, wherein the substituents of the substituted heteroaryl each independently represent (C6-C15)aryl, and R 2 represents hydrogen.
  • R 1 and R 3 each independently may be phenyl; naphthyl; biphenyl; naphthylphenyl; carbazolyl; benzocarbazolyl; carbazolylphenyl; benzocarbazolylphenyl; dibenzocarbazolylphenyl; phenylindolocarbazolyl; triazinyl or pyrimidinyl substituted with one or more of phenyl and biphenyl; triazinyl substituted with one or more of phenyl, naphthyl, and biphenyl; or phenyl, naphthyl, biphenyl, phenylnaphthyl or naphthylphenyl substituted with pyrimidinyl.
  • a and b, or b and c, or c and d of formula 1 are combined with * of formula 2 to form a ring, wherein B 1 and B 2 are bonded at the positions not bonded to * of formula 2 among a to d, regardless of the sequence;
  • B 1 and B 2 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- 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)aryl
  • Ar 1 and Ar 2 each independently represent halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; or may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic or aromatic ring, or a combination thereof.
  • Ar 1 and Ar 2 each independently represent a substituted or unsubstituted (C1-C6)alkyl, or a substituted or unsubstituted (C6-C12)aryl; or may be linked to each other to form a substituted or unsubstituted (5- to 15-membered) polycyclic, alicyclic or aromatic ring, or a combination thereof.
  • Ar 1 and Ar 2 each independently represent an unsubstituted (C1-C6)alkyl or an unsubstituted (C6-C12)aryl; or may be linked to each other to form an unsubstituted (5- to 15-membered) polycyclic aromatic ring.
  • Ar 1 and Ar 2 may be each independently methyl or phenyl; or may be linked to each other to form a spirobifluorene ring.
  • R 11 to R 14 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- 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)aryl
  • R 11 to R 14 each independently represent hydrogen or a substituted or unsubstituted (C6-C12)aryl. In another embodiment of the present disclosure, R 11 to R 14 each independently represent hydrogen or an unsubstituted (C6-C12)aryl. According to another embodiment of the present disclosure, R 11 , R 13 and R 14 are hydrogen, and R 12 is hydrogen or an unsubstituted (C6-C12)aryl. Specifically, R 11 to R 14 may be each independently hydrogen or phenyl.
  • an adjacent substituent when an adjacent substituent may be linked to form a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic or aromatic ring, or a combination thereof, the formed alicyclic, aromatic ring, or a combination thereof may contain at least one heteroatom selected from nitrogen, oxygen, and sulfur.
  • the heteroaryl(ene) and the heterocycloalkyl each independently may contain at least one heteroatom selected from B, N, O, S, Si, and P.
  • the heteroatom may be combined with at least one of substituents selected from hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- 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 unsub
  • R 1 and R 3 each independently represent a substituted or unsubstituted (C6-C20)aryl or a substituted or unsubstituted (5- to 20-membered)heteroaryl;
  • R 2 represents hydrogen;
  • B 1 and B 2 represent hydrogen;
  • Ar 1 and Ar 2 each independently represent a substituted or unsubstituted (C1-C6)alkyl or a substituted or unsubstituted (C6-C12)aryl, or may be linked to each other to form a substituted or unsubstituted (5- to 15-membered) polycyclic, alicyclic or aromatic ring, or a combination thereof;
  • R 11 to R 14 each independently represent hydrogen or a substituted or unsubstituted (C6-C12)aryl.
  • R 1 and R 3 each independently represent a substituted or unsubstituted (C6-C20)aryl or a substituted or unsubstituted (5- to 20-membered)heteroaryl, wherein the substituents of the substituted aryl each independently represent (C6-C15)aryl-substituted or unsubstituted (5- to 20-membered)heteroaryl, and the substituents of the substituted heteroaryl each independently represent (C6-C15)aryl;
  • R 2 represents hydrogen;
  • B 1 and B 2 represent hydrogen;
  • Ar 1 and Ar 2 each independently represent an unsubstituted (C1-C6)alkyl or an unsubstituted (C6-C12)aryl; or may be linked to each other to form an unsubstituted (5- to 15-membered) polycyclic aromatic ring;
  • R 11 to R 14 each independently represent hydrogen or an unsubstituted (C6-C12
  • (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, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and 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, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • (C2-C30)alkynyl is 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, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
  • (C3-C30)cycloalkyl is 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, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • (3- to 7-membered)heterocycloalkyl is a cycloalkyl having 3 to 7 ring backbone atoms, preferably 5 to 7 ring backbone atoms and at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.
  • (C6-C30)aryl(ene) is a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms and may be partially saturated, in which the number of ring backbone carbon atoms is preferably 6 to 25, more preferably 6 to 18.
  • the aryl includes those having a spiro structure, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenyl terphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, etc.
  • (5- to 30-membered)heteroaryl(ene) is an aryl group having at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and 5 to 30 ring backbone atoms; having preferably 1 to 4 heteroatoms, and may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated.
  • heteroaryl(ene) in the present disclosure may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); may comprise those having a spiro structure; and includes a monocyclic ring-type heteroaryl including 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 including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzo
  • substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or functional group, i.e., a substituent.
  • the substituents are each independently (C6-C15)aryl or (C6-C15)aryl-substituted or unsubstituted (5- to 25-membered)heteroaryl.
  • the substituents may be each independently phenyl; biphenyl; carbazolyl; benzocarbazolyl; dibenzocarbazolyl; and triazinyl or pyrimidinyl, etc., substituted with at least one of phenyl, naphthyl and biphenyl.
  • the compound represented by formula 1 may be specifically illustrated by the following compounds, but is not limited thereto:
  • the compounds of formula 1 according to the present disclosure can be prepared by a synthetic method known to one skilled in the art, e.g., the following reaction scheme 1.
  • R 1 to R 3 , B 1 , B 2 , Ar 1 , Ar 2 and R 11 to R 14 are as defined in formula 1.
  • the present disclosure provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1 and an organic electroluminescent device comprising the organic electroluminescent material.
  • the organic electroluminescent material may be comprised solely of the organic electroluminescent compound of the present disclosure, or may further comprise conventional materials included in the organic electroluminescent material.
  • the organic electroluminescent device includes a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode.
  • the organic layer comprises 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 buffer layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.
  • the organic electroluminescent compound represented by formula 1 of the present disclosure may be comprised in at least one layer of the light-emitting layer, the hole injecting layer, the hole transport layer, the hole auxiliary layer, the light-emitting auxiliary layer, the electron transport layer, the electron buffer layer, the electron injection layer, the interlayer, the hole blocking layer, and the electron blocking layer. According to the case, it may be, preferably, comprised in at least one layer of the light-emitting layer, the electron buffer layer, and the electron transport layer. When used in the light-emitting layer, the organic electroluminescent compound of formula 1 of the present disclosure may be comprised as a host material.
  • the organic electroluminescent compound of formula 1 of the present disclosure When used in the electron buffer layer, the organic electroluminescent compound of formula 1 of the present disclosure may be comprised as an electron buffer material. When used in the electron transport layer, the organic electroluminescent compound of formula 1 of the present disclosure may be comprised as an electron transport material.
  • the light-emitting layer may include at least one host and at least one dopant. If necessary, the light-emitting layer may comprise a co-host material, i.e., a plurality of two or more host materials.
  • the host compound to be used in the present disclosure may be a phosphorescent host compound or a fluorescent host compound, and the kinds of host compound to be used are not particularly limited.
  • the host compound may be a fluorescent host compound, for example, may be an anthracene compound represented by the following formula 11.
  • Ar 31 and Ar 32 each independently represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
  • Ar 33 and Ar 34 each independently represent hydrogen, deuterium, halogen, cyano, nitro, hydroxy, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C1-C30)alkylsilyl, a substituted or unsubstituted (C6-C30)arylsilyl, a substituted or un
  • the compound represented by formula 11 may be specifically illustrated by the following compounds, but is not limited thereto:
  • the dopant compound to be used in the present disclosure may be a phosphorescent dopant compound or a fluorescent dopant compound.
  • the dopant compound may be a fluorescent dopant compound, for example, may be a condensed polycyclic amine derivative represented by the following formula 21.
  • Ar 41 represents a substituted or unsubstituted (C6-C50)aryl or styryl;
  • L a represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
  • Ar 42 and Ar 43 each independently represent hydrogen, deuterium, halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl, or may be linked to an adjacent substituent(s) to form a (3- to 30-membered) mono- or polycyclic, alicyclic or aromatic ring, or a combination thereof whose carbon atom may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur; tt represents 1 or 2; and
  • a preferable aryl group for Ar 41 includes a substituted or unsubstituted phenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted anthryl, a substituted or unsubstituted pyrenyl, a substituted or unsubstituted chrysenyl, a substituted or unsubstituted benzofluorenyl, and spiro[fluoren-benzofluorene], etc.
  • the compound of formula 21 may be illustrated by the following compounds, but is not limited thereto:
  • the organic electroluminescent device according to the present disclosure may further comprise at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound in the organic layer.
  • 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 the d-transition elements of the Periodic Table, or at least one complex compound comprising such a metal.
  • the organic electroluminescent device of the present disclosure further comprises at least one light-emitting layer comprising a blue, red or green light-emitting compound known in the art in addition to the compound of the present disclosure, so that it may emit white light. Further, if necessary, it may further include a yellow or orange light-emitting layer.
  • a surface layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer
  • a chalcogenide (including oxides) layer of silicon and aluminum is preferably placed on an anode surface of an electroluminescent medium layer
  • a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer.
  • the operation stability for the organic electroluminescent device may be obtained by the surface layer.
  • the chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.;
  • the metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer.
  • the hole injection layer may be multi-layers in order to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multi-layers may use two compounds simultaneously.
  • the hole transport layer or the electron blocking layer may also be multi-layers.
  • An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode.
  • the electron buffer layer may be multi-layers in order to control the injection of the electron and improve the interfacial properties between the light-emitting layer and the electron injection layer, wherein each of the multi-layers may use two compounds simultaneously.
  • the hole blocking layer or the electron transport layer may also be multi-layers, wherein each layer may use a plurality of compounds.
  • the light-emitting auxiliary layer may be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer.
  • the light-emitting auxiliary layer When the light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it can be used for promoting the hole injection and/or the hole transport, or for preventing the overflow of electrons.
  • the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it can be used for promoting the electron injection and/or the electron transport, or for preventing the overflow of holes.
  • the hole auxiliary layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and may be effective to promote or block the hole transport rate (or the hole injection rate), thereby enabling the charge balance to be controlled.
  • the electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can confine the excitons within the light-emitting layer by blocking the overflow of electrons from the light-emitting layer to prevent a light-emitting leakage.
  • the hole transport layer which is further included, may be used as the hole auxiliary layer or the electron blocking layer.
  • the hole auxiliary layer and the electron blocking layer may have an effect of improving the efficiency and/or the lifespan of the organic electroluminescent device.
  • a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
  • the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
  • the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
  • the oxidative dopant includes various Lewis acids and acceptor compounds
  • the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • a reductive dopant layer may be employed as a charge generating layer to produce an organic electroluminescent device having two or more light-emitting layers and emitting white light.
  • Forming each layer of the organic electroluminescent device of the present disclosure can apply one method of dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc., or wet film-forming methods such as spin coating, dip coating, flow coating methods, etc.
  • the dopant compound and the host compound of the present disclosure may be film-formed by a co-evaporation process or a mixture-evaporation process.
  • a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
  • the organic electroluminescent device of the present disclosure can be used for the manufacture of display devices such as smart phones, tablets, notebooks, PCs, TVs, or display devices for vehicles, or lighting devices such as an outdoor or indoor lighting.
  • An OLED device was produced not according to the present disclosure.
  • a transparent electrode ITO thin film (10 ⁇ /sq) on a glass substrate for an OLED (GEOMATEC CO., LTD.) was subjected to an ultrasonic washing with acetone and isopropyl alcohol, 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 -7 torr.
  • Compound HT-2 was then introduced into another cell of the vacuum vapor deposition apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming a second hole transport layer having a thickness of 5 nm on the first hole transport layer.
  • a light-emitting layer was then deposited as follows.
  • Compound H-15 as a host was introduced into one cell of the vacuum vapor deposition apparatus and compound D-38 as a dopant was introduced into another cell of the apparatus.
  • the two materials were evaporated at a different rate and the dopant was deposited in a doping amount of 2 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 20 nm on the second hole transport layer.
  • compound ET-1 as an electron transport material was introduced into one cell and compound EI-1 was introduced into another cell were evaporated in a weight ratio of 1:1 and deposited to form an electron transport layer having a thickness of 35 nm.
  • an Al cathode having a thickness of 80 nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer.
  • an OLED device was produced.
  • each of the compounds was used by purifying by vacuum sublimation at 10 -6 torr.
  • Comparative Example 2 an OLED device was produced in the same manner as in Comparative Example 1, except that the thickness of the electron transport layer was reduced to 25 nm and the compound of the following Table 1 was inserted as an electron buffer layer having a thickness of 5 nm between the light-emitting layer and the electron transport layer.
  • Table 1 The evaluation results of the organic electroluminescent devices produced in Comparative Example 2 are shown in Table 1 below.
  • electroluminescent device comprising the compound of the present
  • Device Examples 1 to 3 an OLED device was produced in the same manner as in Comparative Example 1, except that the thickness of the electron transport layer was reduced to 25 nm and the compound of the following Table 1 was inserted as an electron buffer layer having a thickness of 5 nm between the light-emitting layer and the electron transport layer.
  • Table 1 The evaluation results of the organic electroluminescent devices produced in Device Examples 1 to 3 are shown in Table 1 below.
  • the organic electroluminescent device including the present compound as an electron buffer material is excellent in terms of driving voltage and/or luminous efficiency while maintaining the same level of color coordinates compared with the organic electroluminescent device not including an electron buffer material or including a conventional material as an electron buffer material.
  • Comparative Examples 3 and 4 an OLED device was produced in the same manner as in Comparative Example 1, except that the electron transport material was changed to the compound of the following Table 2.
  • Table 2 The evaluation results of the organic electroluminescent devices produced in Comparative Examples 3 and 4 are shown in Table 2 below.
  • electroluminescent device comprising the compound of the present
  • the organic electroluminescent device including the present compound as an electron transport material is excellent in terms of driving voltage and/or luminous efficiency while maintaining the same level of color coordinates compared with the organic electroluminescent device including a conventional material as an electron transport material.

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Abstract

La présente invention concerne un composé électroluminescent organique et un dispositif électroluminescent organique comprenant ce dernier. En outre, un dispositif électroluminescent organique ayant une faible tension d'excitation, une efficacité lumineuse élevée et/ou une caractéristique de longue durée de vie peut être fourni avec l'utilisation du composé électroluminescent organique selon la présente invention.The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. In addition, an organic electroluminescent device having a low excitation voltage, a high luminous efficiency and / or a long life characteristic can be provided with the use of the organic electroluminescent compound according to the present invention.

Description

ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME
The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
An electroluminescent (EL) device is a self-light-emitting device with the advantages of providing a wider viewing angle, a greater contrast ratio, and a faster response time. The first organic EL device was developed by Eastman Kodak, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer (see Appl. Phys. Lett. 51, 913, 1987).
An organic EL device (OLED) changes electric energy into light by the injection of a charge into an organic light-emitting material, and commonly comprises an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer of the organic EL device may be composed of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (containing host and dopant materials), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc.; the materials used in the organic layer can be classified into a hole injection material, a hole transport 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., depending on functions. In the organic EL device, holes from an anode and electrons from a cathode are injected into a light-emitting layer by electric voltage, and an exciton having high energy is produced by the recombination of the holes and electrons. The organic light-emitting compound moves into an excited state by the energy and emits light from energy when the organic light-emitting compound returns to the ground state from the excited state.
Research is underway to improve the performance of an organic electroluminescent device by using a material suitable for each layer in the organic electroluminescent device.
For example, an electron transport material actively transports electrons from a cathode to a light-emitting layer and inhibits transport of holes which are not recombined in the light-emitting layer to increase recombination opportunity of holes and electrons in the light-emitting layer. Thus, electron-affinitive materials are used as an electron transport material. Organic metal complexes having light-emitting function such as Alq3 have been conventionally used as an electron transport material. However, Alq3 also has a limitation in providing an organic electroluminescent device having sufficiently satisfactory performance, thus, there is a demand for an electron transport material having improved performance capable of replacing Alq3. Therefore, new electron transport materials have been required, which do not have the above problems, are highly electron-affinitive, and quickly transport electrons in organic EL devices to provide organic EL devices having high luminous efficiency.
Further, the electron buffer layer is a layer for solving the problem of a change in luminance caused by the change of a current characteristic of the device when exposed to a high temperature during a process of producing a panel. In order to obtain a similar current characteristic and a stability to high temperature compared to a device without an electron buffering layer, the characteristic of the compound comprised in the electron buffer layer is important.
US 6,849,348 B2, US 7,285,341 B2, US 8,993,128 B2, and KR 2016-0052399 A disclose indenoquinoline derivatives as compounds for an organic electroluminescent device. However, the compounds disclosed in the above documents do not disclose the compounds of the present disclosure in view of specific compound structure including the kinds and position of the substituent.
The objective of the present disclosure is to provide an organic electroluminescent compound which is effective for manufacturing an organic electroluminescent device having low driving voltage, high efficiency and/or excellent color coordinates.
Common compounds having a fluorene moiety can easily induce electron currents. However, the present inventors found that the compounds are stabilized against stress such as high temperature when the weak positions of quinoline, which are the second and the fourth carbon positions thereof, are protected. As a result of intensive studies, the present inventors found that the organic electroluminescent device comprising the indenoquinoline derivative which is substituted with e.g., aryl and/or heteroaryl at the second and the fourth carbon positions on the basis of quinoline has a higher luminous efficiency as well as a lower driving voltage than the indenoquinoline derivative having only one substituent in the quinoline moiety, and reached the present invention.
More specifically, the present inventors found the aforementioned objective can be achieved by the organic electroluminescent compound represented by the following formula 1, and completed the present invention.
Figure PCTKR2018008140-appb-I000001
Figure PCTKR2018008140-appb-I000002
In formula 1
R1 to R3 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, provided that at least two of R1 to R3 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
a and b, or b and c, or c and d of formula 1 are combined with * of formula 2 to form a ring, wherein B1 and B2 are bonded at the positions not bonded to * of formula 2 among a to d, regardless of the sequence;
B1 and B2 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- 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;
Ar1 and Ar2 each independently represent halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; or may be linked to an adjacent substituent to form a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic or aromatic ring, or a combination thereof;
R11 to R14 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- 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 may be linked to an adjacent substituent to form a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic or aromatic ring, or a combination thereof.
According to the present disclosure, the organic electroluminescent device having a low driving voltage, a high luminous efficiency and/or excellent color coordinates is provided.
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the invention, and is not meant in any way to restrict the scope of the invention.
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, if 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. If necessary, the organic electroluminescent material may be comprised in any layer constituting an organic electroluminescent device. 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, or an electron injection material.
An organic electroluminescent material of the present disclosure comprises at least one compound represented by formula 1 above. The compound of formula 1 may be comprised in at least one layer, which consists of the organic electroluminescent device; and may be in the electron buffer layer and/or the electron transport layer, but not limited thereto; may be included as an electron buffer material when included in the electron buffer layer and may be included as an electron transport material when included in the electron transport layer.
The compound represented by formula 1 will be described in more detail as follows.
The compound represented by formula 1 may be represented by any one of the following formulae 3 to 8.
Figure PCTKR2018008140-appb-I000003
Figure PCTKR2018008140-appb-I000004
Figure PCTKR2018008140-appb-I000005
In formulae 3 to 8,
R1 to R3, B1, B2, Ar1, Ar2, and R11 to R14 are as defined in formula 1.
In formula1, R1 to R3 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, provided that at least two of R1 to R3 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl. In one embodiment of the present disclosure, R1 and R3 each independently represent a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl, and R2 represents hydrogen. In another embodiment of the present disclosure, R1 and R3 each independently represent a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl, and wherein the substituents of the substituted aryl each independently represent (C6-C15)aryl-substituted or unsubstituted (5- to 25-membered)heteroaryl, wherein the substituents of the substituted heteroaryl each independently represent (C6-C15)aryl, and R2 represents hydrogen. Specifically, R1 and R3 each independently may be phenyl; naphthyl; biphenyl; naphthylphenyl; carbazolyl; benzocarbazolyl; carbazolylphenyl; benzocarbazolylphenyl; dibenzocarbazolylphenyl; phenylindolocarbazolyl; triazinyl or pyrimidinyl substituted with one or more of phenyl and biphenyl; triazinyl substituted with one or more of phenyl, naphthyl, and biphenyl; or phenyl, naphthyl, biphenyl, phenylnaphthyl or naphthylphenyl substituted with pyrimidinyl.
a and b, or b and c, or c and d of formula 1 are combined with * of formula 2 to form a ring, wherein B1 and B2 are bonded at the positions not bonded to * of formula 2 among a to d, regardless of the sequence;
B1 and B2 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- 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. In one embodiment of the present disclosure, B1 and B2 represent hydrogen.
Ar1 and Ar2 each independently represent halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; or may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic or aromatic ring, or a combination thereof. In one embodiment of the present disclosure, Ar1 and Ar2 each independently represent a substituted or unsubstituted (C1-C6)alkyl, or a substituted or unsubstituted (C6-C12)aryl; or may be linked to each other to form a substituted or unsubstituted (5- to 15-membered) polycyclic, alicyclic or aromatic ring, or a combination thereof. In another embodiment of the present disclosure, Ar1 and Ar2 each independently represent an unsubstituted (C1-C6)alkyl or an unsubstituted (C6-C12)aryl; or may be linked to each other to form an unsubstituted (5- to 15-membered) polycyclic aromatic ring. Specifically, Ar1 and Ar2 may be each independently methyl or phenyl; or may be linked to each other to form a spirobifluorene ring.
R11 to R14 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- 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 may be linked to each other to form a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic or aromatic ring, or a combination thereof. In one embodiment of the present disclosure, R11 to R14 each independently represent hydrogen or a substituted or unsubstituted (C6-C12)aryl. In another embodiment of the present disclosure, R11 to R14 each independently represent hydrogen or an unsubstituted (C6-C12)aryl. According to another embodiment of the present disclosure, R11, R13 and R14 are hydrogen, and R12 is hydrogen or an unsubstituted (C6-C12)aryl. Specifically, R11 to R14 may be each independently hydrogen or phenyl.
In the formula of the present disclosure, when an adjacent substituent may be linked to form a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic or aromatic ring, or a combination thereof, the formed alicyclic, aromatic ring, or a combination thereof may contain at least one heteroatom selected from nitrogen, oxygen, and sulfur.
In the formula of the present disclosure, the heteroaryl(ene) and the heterocycloalkyl each independently may contain at least one heteroatom selected from B, N, O, S, Si, and P. In addition, the heteroatom may be combined with at least one of substituents selected from hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- 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, and a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.
According to one embodiment of the present disclosure, in the formula 1, R1 and R3 each independently represent a substituted or unsubstituted (C6-C20)aryl or a substituted or unsubstituted (5- to 20-membered)heteroaryl; R2 represents hydrogen; B1 and B2 represent hydrogen; Ar1 and Ar2 each independently represent a substituted or unsubstituted (C1-C6)alkyl or a substituted or unsubstituted (C6-C12)aryl, or may be linked to each other to form a substituted or unsubstituted (5- to 15-membered) polycyclic, alicyclic or aromatic ring, or a combination thereof; R11 to R14 each independently represent hydrogen or a substituted or unsubstituted (C6-C12)aryl.
According to another embodiment of the present disclosure, in formula 1, R1 and R3 each independently represent a substituted or unsubstituted (C6-C20)aryl or a substituted or unsubstituted (5- to 20-membered)heteroaryl, wherein the substituents of the substituted aryl each independently represent (C6-C15)aryl-substituted or unsubstituted (5- to 20-membered)heteroaryl, and the substituents of the substituted heteroaryl each independently represent (C6-C15)aryl; R2 represents hydrogen; B1 and B2 represent hydrogen; Ar1 and Ar2 each independently represent an unsubstituted (C1-C6)alkyl or an unsubstituted (C6-C12)aryl; or may be linked to each other to form an unsubstituted (5- to 15-membered) polycyclic aromatic ring; R11 to R14 each independently represent hydrogen or an unsubstituted (C6-C12)aryl.
Herein, "(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, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and 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, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. "(C2-C30)alkynyl" is 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, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc. "(C3-C30)cycloalkyl" is 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, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. "(3- to 7-membered)heterocycloalkyl" is a cycloalkyl having 3 to 7 ring backbone atoms, preferably 5 to 7 ring backbone atoms and at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. "(C6-C30)aryl(ene)" is a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms and may be partially saturated, in which the number of ring backbone carbon atoms is preferably 6 to 25, more preferably 6 to 18. The aryl includes those having a spiro structure, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenyl terphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl, etc. "(5- to 30-membered)heteroaryl(ene)" is an aryl group having at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and 5 to 30 ring backbone atoms; having preferably 1 to 4 heteroatoms, and may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; may be partially saturated. In addition, the heteroaryl(ene) in the present disclosure may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); may comprise those having a spiro structure; and includes a monocyclic ring-type heteroaryl including 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 including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, 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.
In addition, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced with another atom or functional group, i.e., a substituent. The substituents of the substituted alkyl, the substituted aryl, the substituted heteroaryl, the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted mono- or di- alkylamino, the substituted mono- or di- arylamino, the substituted alkylarylamino, and the substituted mono- or polycyclic, alicyclic, aromatic ring, or the combination thereof, in R1 to R3, B1, B2, Ar1, Ar2, and R11 to R14 are each independently at least one selected from the group consisting of deuterium; halogen; cyano; carboxyl; nitro; hydroxy; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (C6-C30)aryl- substituted or unsubstituted (5- to 30-membered)heteroaryl; (5- to 30-membered)heteroaryl- substituted or unsubstituted (C6-C30)aryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; a mono- or di- (C1-C30)alkylamino; (C1-C30)alkyl- substituted or unsubstituted mono- or di- (C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. In one embodiment of the present disclosure, the substituents are each independently (C6-C15)aryl or (C6-C15)aryl-substituted or unsubstituted (5- to 25-membered)heteroaryl. Specifically, the substituents may be each independently phenyl; biphenyl; carbazolyl; benzocarbazolyl; dibenzocarbazolyl; and triazinyl or pyrimidinyl, etc., substituted with at least one of phenyl, naphthyl and biphenyl.
The compound represented by formula 1 may be specifically illustrated by the following compounds, but is not limited thereto:
Figure PCTKR2018008140-appb-I000006
Figure PCTKR2018008140-appb-I000007
Figure PCTKR2018008140-appb-I000008
Figure PCTKR2018008140-appb-I000009
Figure PCTKR2018008140-appb-I000010
Figure PCTKR2018008140-appb-I000011
Figure PCTKR2018008140-appb-I000012
Figure PCTKR2018008140-appb-I000013
Figure PCTKR2018008140-appb-I000014
Figure PCTKR2018008140-appb-I000015
Figure PCTKR2018008140-appb-I000016
Figure PCTKR2018008140-appb-I000017
Figure PCTKR2018008140-appb-I000018
Figure PCTKR2018008140-appb-I000019
Figure PCTKR2018008140-appb-I000020
Figure PCTKR2018008140-appb-I000021
Figure PCTKR2018008140-appb-I000022
Figure PCTKR2018008140-appb-I000023
Figure PCTKR2018008140-appb-I000024
Figure PCTKR2018008140-appb-I000025
Figure PCTKR2018008140-appb-I000026
Figure PCTKR2018008140-appb-I000027
Figure PCTKR2018008140-appb-I000028
Figure PCTKR2018008140-appb-I000029
Figure PCTKR2018008140-appb-I000030
Figure PCTKR2018008140-appb-I000031
Figure PCTKR2018008140-appb-I000032
Figure PCTKR2018008140-appb-I000033
Figure PCTKR2018008140-appb-I000034
Figure PCTKR2018008140-appb-I000035
Figure PCTKR2018008140-appb-I000036
Figure PCTKR2018008140-appb-I000037
Figure PCTKR2018008140-appb-I000038
Figure PCTKR2018008140-appb-I000039
Figure PCTKR2018008140-appb-I000040
Figure PCTKR2018008140-appb-I000041
Figure PCTKR2018008140-appb-I000042
Figure PCTKR2018008140-appb-I000043
Figure PCTKR2018008140-appb-I000044
Figure PCTKR2018008140-appb-I000045
Figure PCTKR2018008140-appb-I000046
Figure PCTKR2018008140-appb-I000047
Figure PCTKR2018008140-appb-I000048
Figure PCTKR2018008140-appb-I000049
Figure PCTKR2018008140-appb-I000050
Figure PCTKR2018008140-appb-I000051
Figure PCTKR2018008140-appb-I000052
Figure PCTKR2018008140-appb-I000053
Figure PCTKR2018008140-appb-I000054
Figure PCTKR2018008140-appb-I000055
Figure PCTKR2018008140-appb-I000056
Figure PCTKR2018008140-appb-I000057
Figure PCTKR2018008140-appb-I000058
Figure PCTKR2018008140-appb-I000059
Figure PCTKR2018008140-appb-I000060
Figure PCTKR2018008140-appb-I000061
Figure PCTKR2018008140-appb-I000062
Figure PCTKR2018008140-appb-I000063
Figure PCTKR2018008140-appb-I000064
Figure PCTKR2018008140-appb-I000065
The compounds of formula 1 according to the present disclosure can be prepared by a synthetic method known to one skilled in the art, e.g., the following reaction scheme 1.
Figure PCTKR2018008140-appb-I000066
In the reaction scheme 1, R1 to R3, B1, B2, Ar1, Ar2 and R11 to R14 are as defined in formula 1.
The present disclosure provides an organic electroluminescent material comprising the organic electroluminescent compound of formula 1 and an organic electroluminescent device comprising the organic electroluminescent material.
The organic electroluminescent material may be comprised solely of the organic electroluminescent compound of the present disclosure, or may further comprise conventional materials included in the organic electroluminescent material.
The organic electroluminescent device according to the present disclosure includes a first electrode; a second electrode; and at least one organic layer interposed between the first electrode and the second electrode.
One of the first electrode and the second electrode may be an anode and the other may be a cathode. The organic layer comprises 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 buffer layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer.
The organic electroluminescent compound represented by formula 1 of the present disclosure may be comprised in at least one layer of the light-emitting layer, the hole injecting layer, the hole transport layer, the hole auxiliary layer, the light-emitting auxiliary layer, the electron transport layer, the electron buffer layer, the electron injection layer, the interlayer, the hole blocking layer, and the electron blocking layer. According to the case, it may be, preferably, comprised in at least one layer of the light-emitting layer, the electron buffer layer, and the electron transport layer. When used in the light-emitting layer, the organic electroluminescent compound of formula 1 of the present disclosure may be comprised as a host material. When used in the electron buffer layer, the organic electroluminescent compound of formula 1 of the present disclosure may be comprised as an electron buffer material. When used in the electron transport layer, the organic electroluminescent compound of formula 1 of the present disclosure may be comprised as an electron transport material.
The light-emitting layer may include at least one host and at least one dopant. If necessary, the light-emitting layer may comprise a co-host material, i.e., a plurality of two or more host materials.
The host compound to be used in the present disclosure may be a phosphorescent host compound or a fluorescent host compound, and the kinds of host compound to be used are not particularly limited. Specifically, the host compound may be a fluorescent host compound, for example, may be an anthracene compound represented by the following formula 11.
Figure PCTKR2018008140-appb-I000067
In formula 11,
Ar31 and Ar32 each independently represent a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; Ar33 and Ar34 each independently represent hydrogen, deuterium, halogen, cyano, nitro, hydroxy, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted (C1-C30)alkylsilyl, a substituted or unsubstituted (C6-C30)arylsilyl, a substituted or unsubstituted (C6-C30)ar(C1-C30)alkylsilyl, or -NR41R42; R41 and R42 each independently represent hydrogen, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, or may be bonded to each other to form a (3-to 30-membered) mono- or polycyclic, alicyclic or aromatic ring, or a combination of alicyclic and aromatic rings whose carbon atom may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur; rr and ss each independently represent an integer of 1 to 4; and where rr or ss is an integer of 2 or more, each of Ar33 or Ar34 may be the same or different.
The compound represented by formula 11 may be specifically illustrated by the following compounds, but is not limited thereto:
Figure PCTKR2018008140-appb-I000068
Figure PCTKR2018008140-appb-I000069
Figure PCTKR2018008140-appb-I000070
Figure PCTKR2018008140-appb-I000071
Figure PCTKR2018008140-appb-I000072
Figure PCTKR2018008140-appb-I000073
Figure PCTKR2018008140-appb-I000074
Figure PCTKR2018008140-appb-I000075
Figure PCTKR2018008140-appb-I000076
Figure PCTKR2018008140-appb-I000077
Figure PCTKR2018008140-appb-I000078
Figure PCTKR2018008140-appb-I000079
Figure PCTKR2018008140-appb-I000080
Figure PCTKR2018008140-appb-I000081
Figure PCTKR2018008140-appb-I000082
Figure PCTKR2018008140-appb-I000083
Figure PCTKR2018008140-appb-I000084
Figure PCTKR2018008140-appb-I000085
Figure PCTKR2018008140-appb-I000086
Figure PCTKR2018008140-appb-I000087
Figure PCTKR2018008140-appb-I000088
Figure PCTKR2018008140-appb-I000089
The dopant compound to be used in the present disclosure may be a phosphorescent dopant compound or a fluorescent dopant compound. Specifically, the dopant compound may be a fluorescent dopant compound, for example, may be a condensed polycyclic amine derivative represented by the following formula 21.
Figure PCTKR2018008140-appb-I000090
In formula 21,
wherein Ar41 represents a substituted or unsubstituted (C6-C50)aryl or styryl; La represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; Ar42 and Ar43 each independently represent hydrogen, deuterium, halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl, or may be linked to an adjacent substituent(s) to form a (3- to 30-membered) mono- or polycyclic, alicyclic or aromatic ring, or a combination thereof whose carbon atom may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur; tt represents 1 or 2; and where tt is 2, each of
Figure PCTKR2018008140-appb-I000091
may be the same or different.
A preferable aryl group for Ar41 includes a substituted or unsubstituted phenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted anthryl, a substituted or unsubstituted pyrenyl, a substituted or unsubstituted chrysenyl, a substituted or unsubstituted benzofluorenyl, and spiro[fluoren-benzofluorene], etc.
The compound of formula 21 may be illustrated by the following compounds, but is not limited thereto:
Figure PCTKR2018008140-appb-I000092
Figure PCTKR2018008140-appb-I000093
Figure PCTKR2018008140-appb-I000094
Figure PCTKR2018008140-appb-I000095
Figure PCTKR2018008140-appb-I000096
Figure PCTKR2018008140-appb-I000097
Figure PCTKR2018008140-appb-I000098
Figure PCTKR2018008140-appb-I000099
Figure PCTKR2018008140-appb-I000100
Figure PCTKR2018008140-appb-I000101
Figure PCTKR2018008140-appb-I000102
Figure PCTKR2018008140-appb-I000103
Figure PCTKR2018008140-appb-I000104
Figure PCTKR2018008140-appb-I000105
Figure PCTKR2018008140-appb-I000106
Figure PCTKR2018008140-appb-I000107
Figure PCTKR2018008140-appb-I000108
Figure PCTKR2018008140-appb-I000109
Figure PCTKR2018008140-appb-I000110
Figure PCTKR2018008140-appb-I000111
Figure PCTKR2018008140-appb-I000112
Figure PCTKR2018008140-appb-I000113
The organic electroluminescent device according to the present disclosure may further comprise at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound in the organic layer.
Also, in the organic electroluminescent device of the present disclosure, 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 the d-transition elements of the Periodic Table, or at least one complex compound comprising such a metal.
In addition, the organic electroluminescent device of the present disclosure further comprises at least one light-emitting layer comprising a blue, red or green light-emitting compound known in the art in addition to the compound of the present disclosure, so that it may emit white light. Further, if necessary, it may further include a yellow or orange light-emitting layer.
In the organic electroluminescent device of the present disclosure, preferably, at least one layer (hereinafter, "a surface layer") selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s). Specifically, a chalcogenide (including oxides) layer of silicon and aluminum is preferably placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably placed on a cathode surface of an electroluminescent medium layer. The operation stability for the organic electroluminescent device may be obtained by the surface layer. Preferably, the chalcogenide includes SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON, etc.; the metal halide includes LiF, MgF2, CaF2, a rare earth metal fluoride, etc.; and the metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light-emitting layer. The hole injection layer may be multi-layers in order to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multi-layers may use two compounds simultaneously. The hole transport layer or the electron blocking layer may also be multi-layers.
An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode. The electron buffer layer may be multi-layers in order to control the injection of the electron and improve the interfacial properties between the light-emitting layer and the electron injection layer, wherein each of the multi-layers may use two compounds simultaneously. The hole blocking layer or the electron transport layer may also be multi-layers, wherein each layer may use a plurality of compounds.
The light-emitting auxiliary layer may be placed between the anode and the light-emitting layer, or between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it can be used for promoting the hole injection and/or the hole transport, or for preventing the overflow of electrons. When the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it can be used for promoting the electron injection and/or the electron transport, or for preventing the overflow of holes.
In addition, the hole auxiliary layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and may be effective to promote or block the hole transport rate (or the hole injection rate), thereby enabling the charge balance to be controlled. Also, the electron blocking layer may be placed between the hole transport layer (or hole injection layer) and the light-emitting layer, and can confine the excitons within the light-emitting layer by blocking the overflow of electrons from the light-emitting layer to prevent a light-emitting leakage. When an organic electroluminescent device includes two or more hole transport layers, the hole transport layer, which is further included, may be used as the hole auxiliary layer or the electron blocking layer. The hole auxiliary layer and the electron blocking layer may have an effect of improving the efficiency and/or the lifespan of the organic electroluminescent device.
In addition, in the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium. Furthermore, the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds, and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. Also, a reductive dopant layer may be employed as a charge generating layer to produce an organic electroluminescent device having two or more light-emitting layers and emitting white light.
Forming each layer of the organic electroluminescent device of the present disclosure can apply one method of dry film-forming methods such as vacuum evaporation, sputtering, plasma, ion plating methods, etc., or wet film-forming methods such as spin coating, dip coating, flow coating methods, etc. The dopant compound and the host compound of the present disclosure may be film-formed by a co-evaporation process or a mixture-evaporation process.
When using a wet film-forming method, a thin film can be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent where the materials forming each layer can be dissolved or diffused, and where there are no problems in film-formation capability.
Also, the organic electroluminescent device of the present disclosure can be used for the manufacture of display devices such as smart phones, tablets, notebooks, PCs, TVs, or display devices for vehicles, or lighting devices such as an outdoor or indoor lighting.
Hereinafter, the preparation method of an organic electroluminescent compound according to the present disclosure, and the properties thereof will be explained in detail with reference to the representative compounds of the present disclosure in order to understand the present disclosure in detail. However, the present disclosure is not limited by the following examples.
Example 1: Preparation of compound C-1
Figure PCTKR2018008140-appb-I000114
Figure PCTKR2018008140-appb-I000115
Preparation of compound 1-1
Malonic acid (75 g, 716.71 mmol) and POCl3 (713 mL, 7.64 mol) were added into a round bottom flask (RBF) of 500 mL and stirred for 10 minutes. 9,9-dimethyl-9H-fluoren-2-amine (100 g, 478 mmol) was slowly added to the reaction mixture and refluxed at 150℃ for 2 hours and then cooled to room temperature. The reaction mixture was slowly added to ice water and the resulting solid was filtered. The filtered solid was dissolved in CHCl3 and the organic layer was separated and treated with MgSO4. Thereafter, the reaction mixture was purified by column chromatography to obtain compound 1-1 (74 g, 49%).
Preparation of compound 1-2
Compound 1-1 (10 g, 32 mmol), phenylboronic acid (2.70 g, 35 mmol), Pd(PPh3)4 (2.21 g, 2.0 mmol), K2CO3 (13.20 g, 95 mmol), toluene (133 mL, 0.24 M), EtOH (48 mL), and water (48 mL, 2 M) were added to RBF of 500 mL and refluxed. After completion of the reaction, the reaction mixture was cooled to room temperature and then was extracted with dichloromethane and treated with MgSO4. Thereafter, the reaction mixture was purified by column chromatography to obtain compound 1-2 (8.0 g, 71%).
Preparation of compound C-1
Compound 1-2 (8.0 g, 22.0 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (19.57 g, 45.0 mmol), K3PO4 (23.38 g, 110 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (s-phos) (0.74 g, 2.0 mmol), and toluene (173 mL, 0.13 M) were added to RBF of 500 mL and stirred at 140℃ for 30 minutes. Pd2(dba)3 (0.823 g, 2.0 mmol) was then added to the reaction mixture, followed by reflux for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and then was extracted with ethyl acetate and treated with MgSO4. Thereafter, the reaction mixture was purified by column chromatography to obtain compound C-1 (5.1 g, 36%).
Figure PCTKR2018008140-appb-I000116
Example 2: Preparation of compound C-119
Figure PCTKR2018008140-appb-I000117
Figure PCTKR2018008140-appb-I000118
Preparation of compound 2-1
Compound 1-1 (5 g, 16 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (7.62 g, 18 mmol), Pd(PPh3)4 (1.10 g, 0.96 mmol), K2CO3 (6.60 g, 48 mmol), toluene (70 mL, 0.23 M), EtOH (24 mL), and water (24 mL, 2 M) were added to RBF of 500 mL and refluxed. After completion of the reaction, the reaction mixture was cooled to room temperature and then was extracted with dichloromethane and treated with MgSO4. Thereafter, the reaction mixture was purified by column chromatography to obtain compound 2-1 (8.0 g, 85%).
Preparation of compound C-119
Compound 2-1 (7.5 g, 13.0 mmol), 2-naphthylboronic acid (3.25 g, 26 mmol), K3PO4 (13.29 g, 63 mmol), s-phos (0.42 g, 1.0 mmol), and toluene (100 mL, 0.13 M) were added into RBF of 500 mL, and the reaction mixture was stirred at 140℃ for 30 minutes. Pd2(dba)3 (0.468 g, 0.511 mmol) was then added thereto, followed by refluxing for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and then was extracted with ethyl acetate and treated with MgSO4. Thereafter, the reaction mixture was purified by column chromatography to obtain compound C-119 (7.5 g, 86%).
Figure PCTKR2018008140-appb-I000119
Example 3: Preparation of compound C-135
Figure PCTKR2018008140-appb-I000120
Figure PCTKR2018008140-appb-I000121
Preparation of compound 3-1
Compound 1-1 (4 g, 13 mmol), 2,4-diphenyl-6-(3’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1’-biphenyl]-3-yl)-1,3,5-triazine (7.16 g, 14 mmol), Pd(PPh3)4 (0.883 g, 0.764 mmol), K2CO3 (5.28 g, 38 mmol), toluene (60 mL, 0.21 M), EtOH (20 mL), and water (19 mL, 2 M) were added to RBF of 250 mL and refluxed. After completion of the reaction, the reaction mixture was cooled to room temperature and then was extracted with dichloromethane and treated with MgSO4. Thereafter, the reaction mixture was purified by column chromatography to obtain compound 3-1 (5.5 g, 64%).
Preparation of compound C-135
Compound 3-1 (2.5 g, 4.0 mmol), phenylboronic acid (0.919 g, 8.0 mmol), K3PO4 (3.921 g, 18 mmol), s-phos (0.124 g, 0.302 mmol), and toluene (30 mL, 0.126 M) were added to RBF of 100 mL, and the reaction mixture was stirred at 140℃ for 30 minutes. Pd2(dba)3 (0.138 g, 0.151 mmol) was then added thereto, followed by refluxing for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and then was extracted with ethyl acetate and treated with MgSO4. Thereafter, the reaction mixture was purified by column chromatography to obtain compound C-135 (1.5 g, 56%).
Figure PCTKR2018008140-appb-I000122
Example 4: Preparation of compound C-322
Figure PCTKR2018008140-appb-I000123
Figure PCTKR2018008140-appb-I000124
Preparation of compound 4-2
Compound 1-1 (4.6 g, 14.37 mmol), compound 4-1 (8.2 g, 16.03 mmol), Pd(PPh3)4 (1.0 g, 0.87 mmol), K2CO3 (6.0 g, 43.71 mmol), toluene (70 mL, 0.23 M), EtOH (22 mL), and water (22 mL, 2 M) were added to RBF of 250 mL and refluxed. After completion of the reaction, the reaction mixture was cooled to room temperature and then was extracted with dichloromethane and treated with MgSO4. Thereafter, the reaction mixture was purified by column chromatography to obtain compound 4-2 (8.2 g, 86%).
Preparation of compound C-322
Compound 4-2 (8.0 g, 12.06 mmol), compound 4-3 (4.1 g, 24.12 mmol), K3PO4(12.54 g, 59.1 mmol), s-phos (0.4 g, 0.96 mmol), and toluene (142 mL, 0.0852 M) were added to RBF of 250 mL, and the reaction mixture was stirred at 140℃ for 30 minutes. Pd2(dba)3 (0.44 g, 0.48 mmol) was then added thereto, followed by refluxing for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and then was extracted with ethyl acetate and treated with MgSO4. Thereafter, the reaction mixture was purified by column chromatography to obtain compound C-322 (7.5 g, 82%).
Figure PCTKR2018008140-appb-I000125
[Comparative Example 1] Producing a blue light-emitting organic
electroluminescent device not according to the present disclosure
An OLED device was produced not according to the present disclosure. First, a transparent electrode ITO thin film (10 Ω/sq) on a glass substrate for an OLED (GEOMATEC CO., LTD.) was subjected to an ultrasonic washing with acetone and isopropyl alcohol, sequentially, and then was stored in isopropanol. Next, 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 10-7 torr. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming a first hole injection layer having a thickness of 60 nm on the ITO substrate. Compound HI-2 was then introduced into another cell of the vacuum vapor deposition apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer. Compound HT-1 was introduced into another cell of the vacuum vapor deposition apparatus. Thereafter, an electric current was applied to the cell to evaporate the introduced material, thereby forming a first hole transport layer having a thickness of 20 nm on the second hole injection layer. Compound HT-2 was then introduced into another cell of the vacuum vapor deposition apparatus, and an electric current was applied to the cell to evaporate the introduced material, thereby forming a second hole transport layer having a thickness of 5 nm on the first hole transport layer. After forming the hole injection layers and the hole transport layers, a light-emitting layer was then deposited as follows. Compound H-15 as a host was introduced into one cell of the vacuum vapor deposition apparatus and compound D-38 as a dopant was introduced into another cell of the apparatus. The two materials were evaporated at a different rate and the dopant was deposited in a doping amount of 2 wt%, based on the total weight of the host and dopant, to form a light-emitting layer having a thickness of 20 nm on the second hole transport layer. Next, compound ET-1 as an electron transport material was introduced into one cell and compound EI-1 was introduced into another cell were evaporated in a weight ratio of 1:1 and deposited to form an electron transport layer having a thickness of 35 nm. 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 by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced. For each of the materials, each of the compounds was used by purifying by vacuum sublimation at 10-6 torr.
The results of the driving voltage, the luminous efficiency, and the CIE color coordinates of the organic electroluminescent device produced as described above at a luminance of 1,000 nits are shown in the following Table 1.
[Comparative Example 2] Producing a blue light-emitting organic
electroluminescent device not according to the present disclosure
In Comparative Example 2, an OLED device was produced in the same manner as in Comparative Example 1, except that the thickness of the electron transport layer was reduced to 25 nm and the compound of the following Table 1 was inserted as an electron buffer layer having a thickness of 5 nm between the light-emitting layer and the electron transport layer. The evaluation results of the organic electroluminescent devices produced in Comparative Example 2 are shown in Table 1 below.
[Device Examples 1 to 3] Producing a blue light-emitting organic
electroluminescent device comprising the compound of the present
disclosure as an electron buffer material
In Device Examples 1 to 3, an OLED device was produced in the same manner as in Comparative Example 1, except that the thickness of the electron transport layer was reduced to 25 nm and the compound of the following Table 1 was inserted as an electron buffer layer having a thickness of 5 nm between the light-emitting layer and the electron transport layer. The evaluation results of the organic electroluminescent devices produced in Device Examples 1 to 3 are shown in Table 1 below.
Figure PCTKR2018008140-appb-I000126
It was confirmed that the organic electroluminescent device including the present compound as an electron buffer material is excellent in terms of driving voltage and/or luminous efficiency while maintaining the same level of color coordinates compared with the organic electroluminescent device not including an electron buffer material or including a conventional material as an electron buffer material.
[Comparative Examples 3 and 4] Producing a blue light-emitting organic
electroluminescent device not according to the present disclosure
In Comparative Examples 3 and 4, an OLED device was produced in the same manner as in Comparative Example 1, except that the electron transport material was changed to the compound of the following Table 2. The evaluation results of the organic electroluminescent devices produced in Comparative Examples 3 and 4 are shown in Table 2 below.
[Device Examples 4 to 7] Producing a blue light-emitting organic
electroluminescent device comprising the compound of the present
disclosure as an electron transport material
In Device Examples 4 to 7, an OLED device was produced in the same manner as in Comparative Example 1, except that the electron transport material was changed to the compound of the following Table 2. The evaluation results of the organic electroluminescent devices produced in Device Examples 4 to 7 are shown in Table 2 below.
Figure PCTKR2018008140-appb-I000127
It was confirmed that the organic electroluminescent device including the present compound as an electron transport material is excellent in terms of driving voltage and/or luminous efficiency while maintaining the same level of color coordinates compared with the organic electroluminescent device including a conventional material as an electron transport material.
Figure PCTKR2018008140-appb-I000128
Figure PCTKR2018008140-appb-I000129
Figure PCTKR2018008140-appb-I000130
Figure PCTKR2018008140-appb-I000131

Claims (10)

  1. An organic electroluminescent compound represented by the following formula 1:
    Figure PCTKR2018008140-appb-I000132
    Figure PCTKR2018008140-appb-I000133
    wherein,
    R1 to R3 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl, provided that at least two of R1 to R3 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;
    a and b, or b and c, or c and d of formula 1 are combined with * of formula 2 to form a ring, wherein B1 and B2 are bonded at the positions not bonded to * of formula 2 among a to d, regardless of the sequence;
    B1 and B2 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- 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;
    Ar1 and Ar2 each independently represent halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl; or may be linked to an adjacent substituent to form a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic or aromatic ring, or a combination thereof; and
    R11 to R14 each independently represent hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- 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 may be linked to an adjacent substituent to form a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic or aromatic ring, or a combination thereof.
  2. The organic electroluminescent compound according to claim 1, wherein the formula 1 is represented by any one of the following formulae 3 to 8:
    Figure PCTKR2018008140-appb-I000134
    Figure PCTKR2018008140-appb-I000135
    Figure PCTKR2018008140-appb-I000136
    wherein,
    R1 to R3, B1, B2, Ar1, Ar2, and R11 to R14 are as defined in claim 1.
  3. The organic electroluminescent compound according to claim 1, wherein the substituents of the substituted alkyl, the substituted aryl, the substituted heteroaryl, the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkyaryllsilyl, the substituted alkyldiarylsilyl, the substituted arylsilyl, the substituted mono- or di- alkylamino, the substituted mono- or di- arylamino, the substituted alkylarylamino, and the substituted mono- or polycyclic, alicyclic, aromatic ring, or the combination thereof, in R1 to R3, B1, B2, Ar1, Ar2, and R11 to R14, are each independently at least one selected from the group consisting of deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (C6-C30)aryl-substituted or unsubstituted (5- to 30-membered)heteroaryl; (5- to 30-membered)heteroaryl- substituted or unsubstituted (C6-C30)aryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; a mono- or di- (C1-C30)alkylamino; (C1-C30)alkyl-substituted or unsubstituted mono- or di- (C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.
  4. The organic electroluminescent compound according to claim 1, wherein, R1 and R3 each independently represent a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl;
    R2 represents hydrogen;
    B1 and B2 represent hydrogen;
    Ar1 and Ar2 each independently represent a substituted or unsubstituted (C1-C6)alkyl, or a substituted or unsubstituted (C6-C12)aryl, or may be linked to an adjacent substituent to form a substituted or unsubstituted (5- to 15-membered) polycyclic, alicyclic, or aromatic ring, or a combination thereof; and
    R11 to R14 each independently represent hydrogen or a substituted or unsubstituted (C6-C12)aryl.
  5. The organic electroluminescent compound according to claim 1, wherein, R1 and R3 each independently represent a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl, wherein the substituents of the substituted aryl are each independently (C6-C15)aryl-substituted or unsubstituted (5- to 25-membered)heteroaryl, and wherein the substituents of the substituted heteroaryl are each independently (C6-C15)aryl;
    R2 represents hydrogen;
    B1 and B2 represent hydrogen;
    Ar1 and Ar2 each independently represent an unsubstituted (C1-C6)alkyl, or an unsubstituted (C6-C12)aryl; or may be linked to an adjacent substituent to form an unsubstituted (5- to 15-membered) polycyclic aromatic ring; and
    R11 to R14 each independently represent halogen or an unsubstituted (C6-C12)aryl.
  6. The organic electroluminescent compound according to claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:
    Figure PCTKR2018008140-appb-I000137
    Figure PCTKR2018008140-appb-I000138
    Figure PCTKR2018008140-appb-I000139
    Figure PCTKR2018008140-appb-I000140
    Figure PCTKR2018008140-appb-I000141
    Figure PCTKR2018008140-appb-I000142
    Figure PCTKR2018008140-appb-I000143
    Figure PCTKR2018008140-appb-I000144
    Figure PCTKR2018008140-appb-I000145
    Figure PCTKR2018008140-appb-I000146
    Figure PCTKR2018008140-appb-I000147
    Figure PCTKR2018008140-appb-I000148
    Figure PCTKR2018008140-appb-I000149
    Figure PCTKR2018008140-appb-I000150
    Figure PCTKR2018008140-appb-I000151
    Figure PCTKR2018008140-appb-I000152
    Figure PCTKR2018008140-appb-I000153
    Figure PCTKR2018008140-appb-I000154
    Figure PCTKR2018008140-appb-I000155
    Figure PCTKR2018008140-appb-I000156
    Figure PCTKR2018008140-appb-I000157
    Figure PCTKR2018008140-appb-I000158
    Figure PCTKR2018008140-appb-I000159
    Figure PCTKR2018008140-appb-I000160
    Figure PCTKR2018008140-appb-I000161
    Figure PCTKR2018008140-appb-I000162
    Figure PCTKR2018008140-appb-I000163
    Figure PCTKR2018008140-appb-I000164
    Figure PCTKR2018008140-appb-I000165
    Figure PCTKR2018008140-appb-I000166
    Figure PCTKR2018008140-appb-I000167
    Figure PCTKR2018008140-appb-I000168
    Figure PCTKR2018008140-appb-I000169
    Figure PCTKR2018008140-appb-I000170
    Figure PCTKR2018008140-appb-I000171
    Figure PCTKR2018008140-appb-I000172
    Figure PCTKR2018008140-appb-I000173
    Figure PCTKR2018008140-appb-I000174
    Figure PCTKR2018008140-appb-I000175
    Figure PCTKR2018008140-appb-I000176
    Figure PCTKR2018008140-appb-I000177
    Figure PCTKR2018008140-appb-I000178
    Figure PCTKR2018008140-appb-I000179
    Figure PCTKR2018008140-appb-I000180
    Figure PCTKR2018008140-appb-I000181
    Figure PCTKR2018008140-appb-I000182
    Figure PCTKR2018008140-appb-I000183
    Figure PCTKR2018008140-appb-I000184
    Figure PCTKR2018008140-appb-I000185
    Figure PCTKR2018008140-appb-I000186
    Figure PCTKR2018008140-appb-I000187
    Figure PCTKR2018008140-appb-I000188
    Figure PCTKR2018008140-appb-I000189
    Figure PCTKR2018008140-appb-I000190
    Figure PCTKR2018008140-appb-I000191
    Figure PCTKR2018008140-appb-I000192
    Figure PCTKR2018008140-appb-I000193
    Figure PCTKR2018008140-appb-I000194
    Figure PCTKR2018008140-appb-I000195
    Figure PCTKR2018008140-appb-I000196
  7. An organic electroluminescent material comprising the organic electroluminescent compound according to claim 1.
  8. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.
  9. The organic electroluminescent device according to claim 8, wherein the organic electroluminescent compound is contained in at least one layer of an electron buffer layer and an electron transport layer.
  10. A display device comprising the organic electroluminescent compound according to claim 1.
PCT/KR2018/008140 2017-07-21 2018-07-19 Organic electroluminescent compound and organic electroluminescent device comprising the same Ceased WO2019017697A1 (en)

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