WO2020180124A1 - Composé électroluminescent organique et matériau électroluminescent organique le comprenant, et dispositif électroluminescent organique - Google Patents

Composé électroluminescent organique et matériau électroluminescent organique le comprenant, et dispositif électroluminescent organique Download PDF

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WO2020180124A1
WO2020180124A1 PCT/KR2020/003110 KR2020003110W WO2020180124A1 WO 2020180124 A1 WO2020180124 A1 WO 2020180124A1 KR 2020003110 W KR2020003110 W KR 2020003110W WO 2020180124 A1 WO2020180124 A1 WO 2020180124A1
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substituted
unsubstituted
membered
alkyl
organic electroluminescent
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PCT/KR2020/003110
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English (en)
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Ga-Won Lee
Ji-Song JUN
Hong-Se OH
Kyoung-Jin Park
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020200027111A external-priority patent/KR20200107836A/ko
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to CN202080016238.7A priority Critical patent/CN113474438A/zh
Publication of WO2020180124A1 publication Critical patent/WO2020180124A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present disclosure relates to an organic electroluminescent compound and an organic electroluminescent material comprising the same, and an organic electroluminescent device.
  • An electroluminescent device is a self-light-emitting display device which has advantages in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time.
  • the first organic EL device was developed by Eastman Kodak in 1987, by using small aromatic diamine molecules and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • Iridium(III) complexes have been widely known as phosphorescent light-emitting materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C-3’)iridium(acetylacetonate) [(acac)Ir(btp) 2 ], tris(2-phenylpyridine)iridium [Ir(ppy) 3 ], and bis(4,6-difluorophenylpyridinato-N,C2)picolinato iridium (Firpic) as red-, green-, and blue-emitting materials, respectively.
  • CBP 4,4’-N,N’-dicarbazol-biphenyl
  • BCP bathocuproine
  • BAlq aluminum(III) bis(2-methyl-8-quinolinate)(4-phenylphenolate)
  • WO 2017/086729 A1 discloses an organic electroluminescent device including a compound in which the aryl bonded directly to the 1-position on carbon and to the nitrogen atom of the carbazole moiety, contains an octagonal ring as a basic skeleton with nitrogen atom, oxygen atom, or sulfur atom, as a linker.
  • the prior art does not disclose an organic electroluminescent material containing the compound of the basic skeleton like the present disclosure.
  • the object of the present disclosure is firstly, to provide an organic electroluminescent compound which is effective to produce an organic electroluminescent device having low driving voltage and/or high luminous efficiency and/or long lifespan, and secondly, to provide an organic electroluminescent material and an organic electroluminescent device comprising the organic electroluminescent compound.
  • the organic electroluminescent compound represented by the following formula 1 in which the aryl bonded directly to the nitrogen atom of the carbazole is fused throughout the structure to form an octagonal ring. Further, the device characteristics with good efficiency can be realized by inducing stereoscopical distortion to the compound of formula 1, thereby breaking the ⁇ -conjugation and having high triplet energy (E T ). In addition, the organic electroluminescent compound represented by the following formula 1 has a high HOMO level due to its structure properties, thereby improving hole mobility in the light-emitting layer, so that the organic electroluminescent device may improve luminous efficiency and lifespan characteristic.
  • X 1 to X 15 each independently represent CR a or N;
  • Q represents N-L-Ar, O, S, or CR 51 R 52 ;
  • L represents a single bond, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene;
  • Ar represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino;
  • R a represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl,
  • R 51 and R 52 each independently represent 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 each other to form a ring.
  • an organic electroluminescent device having low driving voltage and/or high luminous efficiency and/or superior lifespan characteristic can be prepared.
  • the present disclosure relates to an organic electroluminescent compound represented by formula 1 above, an organic electroluminescent material comprising the organic electroluminescent compound, and an organic electroluminescent device comprising the organic electroluminescent material.
  • 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 material layer constituting an organic electroluminescent device, as necessary.
  • organic electroluminescent material means a material that may be used in an organic electroluminescent device, and may comprise at least one compound.
  • the organic electroluminescent material may be comprised in any layer constituting an organic electroluminescent device, as necessary.
  • the organic electroluminescent material may be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material.
  • (C1-C30)alkyl is meant to be a linear or branched alkyl having 1 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10.
  • the above alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert -butyl, etc.
  • (C2-C30)alkenyl is meant to be a linear or branched alkenyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10.
  • the above alkenyl may include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • (C2-C30)alkynyl is meant to be a linear or branched alkynyl having 2 to 30 carbon atoms constituting the chain, in which the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10.
  • the above alkynyl may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.
  • (C3-C30)cycloalkyl(ene) 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, and more preferably 3 to 7.
  • the above cycloalkyl may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • (3- to 7-membered)heterocycloalkyl is a cycloalkyl having 3 to 7 ring backbone atoms in which the number of ring backbone atom is preferably 5 to 7, 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, in which the number of the ring backbone carbon atoms is preferably 6 to 25, more preferably 6 to 18, may be partially saturated, and may comprise a spiro structure.
  • aryl specifically include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, me
  • the aryl may be o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-t-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, p-terphenyl-4-
  • (3- to 30-membered)heteroaryl(ene) is an aryl having 3 to 30 ring backbone atoms, in which the number of ring backbone atoms is preferably 5 to 25, including at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si, P, and Ge.
  • the above heteroaryl may be a monocyclic ring, or a fused ring condensed with at least one benzene ring; and may be partially saturated.
  • the above heteroatom may be linked with at least one substituent selected from the group consisting of 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 unsubstit
  • the above heteroaryl may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and may comprise a spiro structure.
  • the heteroaryl specifically may include 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, dibenzothioph
  • the heteroaryl may be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7-indolizidinyl, 8-indolizidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridiny
  • Ortho position is a compound with substituents, which are adjacent to each other, e.g., at the 1 and 2 positions on benzene.
  • Meta position is the next substitution position of the immediately adjacent substitution position, e.g., a compound with substituents at the 1 and 3 positions on benzene.
  • Para position is the next substitution position of the meta position, e.g., a compound with substituents at the 1 and 4 positions on benzene.
  • a ring formed in linking to an adjacent substituent means a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof, formed by linking or fusing two or more adjacent substituents, preferably may be a substituted or unsubstituted (3- to 26-membered) mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof.
  • the formed ring may include at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably, N, O, and S.
  • the number of atoms in the ring skeleton is 5 to 20; according to another embodiment of the present disclosure, the number of atoms in the ring skeleton is 5 to 15.
  • the fused ring may be, a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, or or
  • 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 organic electroluminescent compound according to one embodiment is represented by the following formula 1.
  • X 1 to X 15 each independently represent CR a or N;
  • Q represents N-L-Ar, O, S, or CR 51 R 52 ;
  • L represents a single bond, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene;
  • Ar represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino;
  • R a represents hydrogen, deuterium, halogen, cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl,
  • R 51 and R 52 each independently represent 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 each other to form a ring.
  • X 1 to X 15 may be all CR a .
  • R a may be hydrogen, deuterium, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted mono- or di- (C6-C30)arylamino; or may be linked to adjacent substituents to form a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic, aromatic ring, or a combination thereof, preferably, hydrogen, deuterium, a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- to 25-membered)heteroaryl, or a substituted or unsubstituted di(C6-C25)arylamino; or may be linked to adjacent substituents to form a substituted or unsubstituted (5- to 25-membered) mono
  • R a may be phenyl unsubstituted or substituted with at least one of triazine, diphenylamino, phenylfluorenylamino, carbazole, and dibenzofuran; a substituted or unsubstituted p-biphenyl; a substituted or unsubstituted carbazolyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted dibiphenyl-4-ylamino; a substituted or unsubstituted quinoxalinyl; a substituted or unsubstituted quinazolinyl; a substituted or unsubstituted triazinyl; or may be linked to adjacent R a s to form
  • L may be a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene, preferably, a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (5- to 25-membered)heteroarylene, more preferably, a single bond, a substituted or unsubstituted (C6-C18)arylene, or a substituted or unsubstituted (5- to 18-membered)heteroarylene.
  • L may be a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted m-biphenylene, a substituted or unsubstituted p-biphenylene, a substituted or unsubstituted pyridinylene, a substituted or unsubstituted pyrimidinylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted triazinylene, a substituted or unsubstituted quinazolinylene, a substituted or unsubstituted quinoxalinylene, or a substituted or unsubstituted benzoquinoxalinylene.
  • Ar may be a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted di(C6-C30)arylamino, preferably, a substituted or unsubstituted (C6-C25)aryl, a substituted or unsubstituted (5- to 25-membered)heteroaryl, or a substituted or unsubstituted di(C6-C25)arylamino, more preferably, a substituted or unsubstituted (C6-C18)aryl, a substituted or unsubstituted (5- to 18-membered)heteroaryl, or a substituted or unsubstituted di(C6-C18)arylamino.
  • Ar may be a substituted or unsubstituted phenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzonaphthothiophenyl, a substituted or unsubstituted pyridinyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted
  • R 51 and R 52 each independently may be a substituted or unsubstituted (C1-C30)alkyl or a substituted or unsubstituted (C6-C30)aryl, preferably, a substituted or unsubstituted (C1-C20)alkyl or a substituted or unsubstituted (C6-C25)aryl, more preferably, a substituted or unsubstituted (C1-C10)alkyl or a substituted or unsubstituted (C6-C18)aryl.
  • R 51 and R 52 each independently may be methyl or phenyl.
  • the compound of formula 1 may be represented by any one of the following formulas 2-1 to 2-4.
  • L, Ar, R 51 , and R 52 are as defined in formula 1;
  • R 1 to R 15 are as defined as R a in formula 1.
  • Ar, R a , R 51 , and R 52 each independently may be selected from any one of the substituents listed in the following Group 1.
  • D1 and D2 each independently represent benzene ring or naphthalene ring;
  • X 21 represents O, S, NR 31 , or CR 32 R 33 ;
  • X 22 each independently represent CR 34 or N; provided that at least one X 22 represent(s) N;
  • X 23 each independently represent CR 35 or N;
  • L 11 to L 18 each independently represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene;
  • R’ 11 to R’ 22 and R 31 to R 35 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 (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to adjacent substituents to form a ring;
  • aa, ff, and gg each independently represent an integer of 1 to 5
  • bb represents an integer of 1 to 7
  • cc to ee each independently represent an integer of 1 to 4;
  • each R’ 11 , each R’ 12 , each R’ 13 , each R’ 14 , each R’ 15 , each R’ 16 , or each R’ 17 may be the same or different.
  • Ar, R a , R 51 , and R 52 each independently may be selected from any one of the substituents listed in the following Group 2.
  • a 1 to A 3 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C6-C30)aryl; and
  • L is as defined as L in formula 1.
  • the organic electroluminescent compound represented by formula 1 may be more specifically illustrated by the following compounds, but is not limited thereto.
  • the compound represented by formula 1 according to the present disclosure may be prepared as represented by the following reaction schemes 1 to 6, but is not limited thereto; further, it may be produced by a synthetic method known to a person skilled in the art.
  • exemplary synthesis examples of the compounds represented by formula 1 are described, but they are based on Buchwald-Hartwig cross coupling reaction, N-arylation reaction, H-mont-mediated etherification reaction, Miyaura borylation reaction, Suzuki cross-coupling reaction, Intramolecular acid-induced cyclization reaction, Pd(II)-catalyzed oxidative cyclization reaction, Grignard reaction, Heck reaction, Cyclic Dehydration reaction, SN 1 substitution reaction, SN 2 substitution reaction, and Phosphine-mediated reductive cyclization reaction etc. It will be understood by one skilled in the art that the above reaction proceeds even if other substituents defined in the formulas 1 and 2-1 to 2-4 other than the substituents described in the specific synthesis examples are bonded.
  • the present disclosure may provide an organic electroluminescent material comprising an organic electroluminescent compound of formula 1, and an organic electroluminescent device comprising the organic electroluminescent material.
  • the organic electroluminescent material may be made solely of the organic electroluminescent compound of the present disclosure, and may further comprise conventional materials included in the organic electroluminescent material. When two or more species of materials are included in one layer, the at least two compounds may be a mixture-evaporation or separately a co-evaporation to form a layer.
  • the organic electroluminescent material according to one embodiment may comprise at least one compound represented by formula 1.
  • the compound of formula 1 may be comprised in the light-emitting layer, specifically, the organic electroluminescent compound represented by formula 1 of the present disclosure may be comprised as the first host material in the organic electroluminescent device.
  • the organic electroluminescent material may use the organic electroluminescent compound represented by formula 1 as a co-host material. That is, the light-emitting layer may further comprise the other organic electroluminescent compound as a second host material other than the organic electroluminescent compound of formula 1 (a first host material).
  • the first host compound and the second host compound may be included in the organic electroluminescent material in the weight ratio of the first host compound to the second host compound of about 1:9 to 9:1, e.g., 2:8 to 8:2, 3:7 to 7:3, 4:6 to 6:4, and 5:5.
  • the at least two compounds may be a mixture-evaporation or separately a co-evaporation to form a layer.
  • the second host material may use the well-known phosphorescent host material, and it is preferable to use the compound represented by the following formula 3 or 4 in terms of luminous efficiency, but is not limited thereto.
  • W represents O, S, CR b4 R b5 , or NR b6 ;
  • L c represents a single bond, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene;
  • Ar c represents a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
  • R b1 to R b6 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 (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C
  • each R b1 , each R b2 , and each R b3 may be the same or different.
  • L c may be a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene, preferably, a single bond, a substituted or unsubstituted (C6-C25)arylene, or a substituted or unsubstituted (5- to 25-membered)heteroarylene, and more preferably, a single bond, a substituted or unsubstituted (C6-C18)arylene, or a substituted or unsubstituted (5- to 18-membered)heteroarylene.
  • L c may be a single bond, or a substituted or unsubstituted phenylene, a substituted or unsubstituted pyridylene, a substituted or unsubstituted pyrimidinylene, a substituted or unsubstituted carbazolylene, a substituted or unsubstituted quinolinylene, or a substituted or unsubstituted quinazolinylene.
  • Ar c may be a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (5- to 30-membered)heteroaryl, preferably, a substituted or unsubstituted (C6-C25)aryl or a substituted or unsubstituted (5- to 25-membered)heteroaryl, more preferably, (C6-C18)aryl unsubstituted or substituted with at least one (C6-C18)aryl and (5- to 18-membered)heteroaryl, or (C6-C18)aryl-substituted or unsubstituted (5- to 18-membered)heteroaryl.
  • Ar c may be a substituted or unsubstituted phenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted triazinyl, or a substituted or unsubstituted dibenzothiophenyl.
  • R b1 to R b6 each independently may be hydrogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl, preferably, hydrogen, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 25-membered)heteroaryl, more preferably, hydrogen, a substituted or unsubstituted (C1-C4)alkyl, a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted (5- to 18-membered)heteroaryl.
  • R b1 may be hydrogen, a substituted or unsubstituted phenyl or a substituted or unsubstituted carbazolyl;
  • R b2 may be hydrogen or a substituted or unsubstituted dibenzothiophenyl;
  • R b3 may be hydrogen or a substituted or unsubstituted triazinyl;
  • R b4 and R b5 each independently may be methyl or phenyl; and
  • R b6 may be a substituted or unsubstituted phenyl or a substituted or unsubstituted biphenyl.
  • the second host material may be more specifically illustrated by the following compounds, but is not limited thereto.
  • TPS is triphenylsilyl
  • the light-emitting layer may further comprise at least one dopant.
  • the dopant comprised in the organic electroluminescent material of the present disclosure may be used at least one phosphorescent or fluorescent dopant, preferably a phosphorescent dopant.
  • the phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particulary limited, but may be preferably a metallated complex compound(s) of a metal atom(s) selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably an ortho-metallated complex compound(s) of a metal atom(s) selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably ortho-metallated iridium complex compound(s).
  • the dopant comprised in the organic electroluminescent device of the present disclosure may be illustrated the compound represented by the following formula 101, but is not limited thereto:
  • L is selected from any one of the following structures 1 to 3:
  • R 100 to R 103 each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, cyano, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or a substituted or unsubstituted (C1-C30)alkoxy;
  • R 100 to R 103 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, e.g., a substituted or unsubstituted quinoline, a substituted or unsubstituted benzofuropyridine, a substituted or unsubstituted benzothienopyridine, a substituted or unsubstituted indenopyridine
  • R 104 to R 107 each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, cyano, or a substituted or unsubstituted (C1-C30)alkoxy; or R 104 to R 107 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring, e.g., a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted dibenzofur
  • R 201 to R 220 each independently represent hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, or a substituted or unsubstituted (C6-C30)aryl; R 201 to R 220 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted fused ring; and
  • n an integer of 1 to 3.
  • the specific examples of the dopant compound include the following, but are not limited thereto:
  • the organic electroluminescent device may comprise a first electrode; a second electrode; and at least one organic layer between the first and second electrodes.
  • the organic electroluminescent compound represented by the formula 1 of the present disclosure may be included in at least one layer.
  • the organic layer includes a light-emitting layer comprising the organic electroluminescent compound of the present disclosure.
  • the light-emitting layer is comprised solely of the organic electroluminescent compound represented by formula 1 or at least two species of the organic electroluminescent compound of the present disclosure, or may further comprise the organic electroluminescent compound represented by formula 3 or 4.
  • the organic layer may comprise a light-emitting layer, and may further comprise at least one layer selected from a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an interlayer, a hole blocking layer, and an electron blocking layer, wherein each layer may be further constituted of several layers.
  • the organic layer may further comprise at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound.
  • the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides, and organic metals of the d-transition elements of the Periodic Table, or at least one complex compound comprising such a metal.
  • An organic electroluminescent material may be used as light-emitting materials for a white organic light-emitting device.
  • the white organic light-emitting device has suggested various structures such as a parallel side-by-side arrangement method, a stacking arrangement method, or CCM (color conversion material) method, etc., according to the arrangement of R (Red), G (Green), B (blue), or YG (yellowish green) light-emitting units.
  • the organic electroluminescent material according to one embodiment may also be applied to the organic electroluminescent device comprising a QD (quantum dot).
  • first electrode and the second electrode may be an anode and the other may be a cathode.
  • first electrode and the second electrode may each be formed as a transmissive conductive material, a transflective conductive material, or a reflective conductive material.
  • the organic electroluminescent device may be a top emission type, a bottom emission type, or a both-sides emission type according to the kinds of the material forming the first electrode and the second electrode.
  • 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 injection layer may be doped as a p-dopant.
  • 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 or the electron blocking layer may be multi-layers, and wherein each layer may use a plurality of compounds.
  • 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 electron injection layer may be doped as an n-dopant.
  • 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 hole transport layer which is further included, may be used as the hole auxiliary layer or the electron blocking layer.
  • the light-emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer may have an effect of improving the efficiency and/or the lifespan of the organic electroluminescent device.
  • a surface layer selected from a chalcogenide layer, a halogenated metal layer, and a metal oxide layer
  • a surface layer selected from a chalcogenide layer, a halogenated metal 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 halogenated metal 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 halogenated metal 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 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 prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.
  • each layer of the organic electroluminescent device of the present disclosure 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., can be used.
  • a wet film-forming method a thin film may be formed by dissolving or diffusing materials forming each layer into any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc.
  • the solvent may 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 above methods may be used, preferably, co-evaporation or mixture-evaporation may be used.
  • the co-deposition is a mixed deposition method in which two or more isomer materials are put into respective individual crucible sources and a current is applied to both cells simultaneously to evaporate the materials and to perform mixed deposition; and the mixed deposition is a mixed deposition method in which two or more isomer materials are mixed in one crucible source before deposition, and then a current is applied to one cell to evaporate the materials.
  • first host compound and the second host compound according to one embodiment are present in the same layer or another layer in the organic electroluminescent device, two host compounds may be individually deposited. For example, the first host compound is deposited, thereafter the second host compound may be deposited.
  • the present disclosure can provide display devices such as smartphones, tablets, notebooks, PCs, TVs, or display devices for vehicles, or lighting devices such as outdoor or indoor lighting, by using a plurality of host materials of the present disclosure.
  • An OLED comprising the organic electroluminescent compound according to the present disclosure was produced.
  • a transparent electrode indium tin oxide (ITO) thin film (10 ⁇ /sq) on a glass substrate for an OLED (GEOMATEC CO., LTD., Japan) was subjected to an ultrasonic washing with acetone, ethanol, and distilled water, sequentially, and then was stored in isopropanol.
  • the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus.
  • Compound HI-1 was introduced into a cell of the vacuum vapor deposition apparatus, and the pressure in the chamber of the apparatus was then controlled to 10 -6 torr.
  • a light-emitting layer using a plurality of host materials was then deposited thereon as follows: The compound C-31 as a host was introduced into one cell of the vacuum vapor deposition apparatus and compound D-50 was introduced into another cell as a dopant. At the same time, the dopant material was evaporated at different rate, and doped in a doping amount of 10 wt% with respect to the total amount of the host and the dopant, to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
  • compounds ET-1 and EI-1 were introduced into another two cells, were evaporated at a rate of 4:6, and were deposited to form an electron transport layer having a thickness of 35 nm on the light-emitting layer.
  • an Al cathode having a thickness of 80 nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus.
  • an OLED was produced.
  • Each compound was purified by vacuum sublimation under 10 -6 torr and then used.
  • An OLED was produced in the same manner as in Device Example 1, except that compound C-1 as a first host compound and compound B-46 as a second host compound were introduced into one cell and compound D-50 was introduced into another cell as a dopant.
  • the two host materials were evaporated at a rate of 2:1 and simultaneously, at the same time, the dopant was evaporated in a doping amount of 10 wt% with respect to the total amount of the host and the dopant, to form a light-emitting layer having a thickness of 40 nm on the second hole transport layer.
  • An OLED was produced in the same manner as in Device Example 2, except that the compound C-15 as a first host compound and compound B-46 as a second host compound were used in the light-emitting layer.
  • An OLED was produced in the same manner as in Device Example 1, except that compound A as a host and compound D-50 as a dopant were used to form the light-emitting layer having a thickness of 30 nm on the second hole transport layer and Balq was deposited to form a hole blocking layer having a thickness of 10 nm.
  • the organic electroluminescent device using the organic electroluminescent compound represented by formula 1 according to the present disclosure as a sole host and co-host material has lower driving voltage and higher luminous efficiency and superior color coordinates characteristics than the organic electroluminescent device of Comparative Example 1 using solely the conventional host material.

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Abstract

La présente invention concerne un composé électroluminescent organique et un matériau électroluminescent organique le comprenant, et un dispositif électroluminescent organique. Du fait qu'il comprend le composé électroluminescent organique et un matériau électroluminescent organique le comprenant, un dispositif électroluminescent organique ayant une faible tension de commande et/ou une efficacité lumineuse élevée et/ou une longue durée de vie peut être fourni.
PCT/KR2020/003110 2019-03-07 2020-03-05 Composé électroluminescent organique et matériau électroluminescent organique le comprenant, et dispositif électroluminescent organique WO2020180124A1 (fr)

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CN202080016238.7A CN113474438A (zh) 2019-03-07 2020-03-05 有机电致发光化合物和包含其的有机电致发光材料、以及有机电致发光装置

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KR10-2019-0026086 2019-03-07
KR1020200027111A KR20200107836A (ko) 2019-03-07 2020-03-04 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 재료, 및 유기 전계 발광 소자
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130012700A1 (en) * 2010-03-25 2013-01-10 Merck Patent Gmbh Materials for organic electroluminescent devices
WO2016182186A1 (fr) * 2015-05-11 2016-11-17 Rohm And Haas Electronic Materials Korea Ltd. Composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
KR20180012709A (ko) * 2016-07-27 2018-02-06 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
CN108727398A (zh) * 2018-06-28 2018-11-02 宁波卢米蓝新材料有限公司 一种稠环化合物及其制备方法和用途
KR20190001967A (ko) * 2017-06-28 2019-01-08 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130012700A1 (en) * 2010-03-25 2013-01-10 Merck Patent Gmbh Materials for organic electroluminescent devices
WO2016182186A1 (fr) * 2015-05-11 2016-11-17 Rohm And Haas Electronic Materials Korea Ltd. Composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
KR20180012709A (ko) * 2016-07-27 2018-02-06 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20190001967A (ko) * 2017-06-28 2019-01-08 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
CN108727398A (zh) * 2018-06-28 2018-11-02 宁波卢米蓝新材料有限公司 一种稠环化合物及其制备方法和用途

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