CN117263891A - Multiple host materials and organic electroluminescent device comprising the same - Google Patents
Multiple host materials and organic electroluminescent device comprising the same Download PDFInfo
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- CN117263891A CN117263891A CN202310738450.XA CN202310738450A CN117263891A CN 117263891 A CN117263891 A CN 117263891A CN 202310738450 A CN202310738450 A CN 202310738450A CN 117263891 A CN117263891 A CN 117263891A
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- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
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- 150000002602 lanthanoids Chemical class 0.000 description 1
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- 238000004519 manufacturing process Methods 0.000 description 1
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- 150000005309 metal halides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
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- NYESPUIMUJRIAP-UHFFFAOYSA-N naphtho[1,2-e][1]benzofuran Chemical group C1=CC=CC2=C3C(C=CO4)=C4C=CC3=CC=C21 NYESPUIMUJRIAP-UHFFFAOYSA-N 0.000 description 1
- XRJUVKFVUBGLMG-UHFFFAOYSA-N naphtho[1,2-e][1]benzothiole Chemical group C1=CC=CC2=C3C(C=CS4)=C4C=CC3=CC=C21 XRJUVKFVUBGLMG-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
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- 230000006798 recombination Effects 0.000 description 1
- 238000006476 reductive cyclization reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
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- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000005106 triarylsilyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- SLAJUCLVZORTHN-UHFFFAOYSA-N triphenylgermanium Chemical class C1=CC=CC=C1[Ge](C=1C=CC=CC=1)C1=CC=CC=C1 SLAJUCLVZORTHN-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
The present disclosure relates to a plurality of host materials including at least one first host compound and at least one second host compound, and an organic electroluminescent device including the plurality of host materials. By including a specific combination of compounds according to the present disclosure as a host material, an organic electroluminescent device having low driving voltage, high luminous efficiency, and long life characteristics can be provided.
Description
Technical Field
The present disclosure relates to a variety of host materials and an organic electroluminescent device including the same.
Background
Organic electroluminescent devices (OLEDs) were first developed by Eastman Kodak (Eastman Kodak) in 1987 by using small aromatic diamine molecules and aluminum complexes as materials for forming the light emitting layer [ appl. Phys. Lett. [ applied physics rapid report ]51,913,1987].
The light emitting material of the OLED is the most important factor determining the light emitting efficiency of the device, and can be functionally divided into host materials and dopant materials. The light emitting material may be used by mixing a host and a dopant in order to improve color purity, light emitting efficiency, and stability. In general, a device having excellent Electroluminescent (EL) characteristics has a structure including a light emitting layer formed by doping a dopant into a host. When such dopant/host material systems are used as light emitting materials, their choice is important because the host material greatly affects the efficiency and lifetime of the light emitting device.
Recently, an urgent task is to develop an OLED having high efficiency and long life characteristics. In particular, in view of EL characteristics required for medium-and large-sized OLED panels, development of highly excellent light emitting materials superior to conventional light emitting materials is urgently required.
Korean patent application laid-open No. 10-2014-0057439 discloses an organic electroluminescent device using a heterocyclic compound as a host or a hole-transporting material. However, the prior art does not specifically disclose an organic electroluminescent device using a plurality of host materials of a specific combination of the present disclosure, and there is still a need to develop a host material for improving the performance of an OLED.
Disclosure of Invention
Technical problem
An object of the present disclosure is, firstly, to provide various host materials capable of producing an organic electroluminescent device having low driving voltage and/or high luminous efficiency and/or long life characteristics, and, secondly, to provide an organic electroluminescent device including these host materials.
Solution to the problem
As a result of intensive studies to solve the above technical problems, the present inventors have found that the aforementioned objects can be achieved by a plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following formula 1 and the second host compound is represented by the following formula 2, so as to complete the present invention.
In the formula (1) of the present invention,
x represents O, S, CR 11 R 12 、NR 13 Or Se;
R 11 to R 13 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; or may be attached to adjacent substituents to form one or more rings; and is also provided with
A represents a substituted or unsubstituted phenanthrene ring represented by the following formula 1-1;
in the formulae 1 and 1-1,
R 1 to R 4 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl,
Provided that R 1 To R 4 At least one of which is
L 1 And L 2 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (C3-C30) cycloalkylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 1 to Ar 5 Each independently represents a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
a and d are integers of 1 to 4, b and c are integers of 1 or 2, and when a to d are integers of 2 or more, R 1 To R 4 Each can be in phase withSame or different; and is also provided with
* Represents a linking site with formula 1;
in the formula (2) of the present invention,
X 1 to X 3 Each independently represents N, CH or CD;
L 21 To L 23 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 21 to Ar 23 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, (C3-C30) aliphatic ring, and substituted or unsubstituted fused ring of (C6-C30) aromatic ring, or-N- (R') (R "); or may be attached to adjacent substituents to form one or more rings; provided that Ar is 21 To Ar 23 At least one of which is a substituted or unsubstituted (3-to 30-membered) heteroaryl; and is also provided with
R 'and R' each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
The beneficial effects of the invention are that
By using a plurality of host materials according to the present disclosure, an organic electroluminescent device having low driving voltage and/or high luminous efficiency and/or long life characteristics can be provided.
Detailed Description
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the invention and is not meant to limit the scope of the invention in any way.
The present disclosure relates to a plurality of host materials including at least one first host compound and at least one second host compound, wherein the first host compound is represented by formula 1 and the second host compound is represented by formula 2, and an organic electroluminescent device including the same.
The plurality of host materials of the present disclosure may further comprise at least one third host compound different from the first host compound and the second host compound.
The present disclosure relates to an organic electroluminescent compound represented by formula 3 and an organic electroluminescent material comprising the same, and an organic electroluminescent device.
The term "plurality of organic electroluminescent materials" in the present disclosure means an organic electroluminescent material comprising a combination of at least two compounds, which may be contained in any layer constituting an organic electroluminescent device. It may mean both a material before (e.g., before vapor deposition) and a material after (e.g., after vapor deposition) being included in the organic electroluminescent device. For example, the plurality of organic electroluminescent materials may be a combination of at least two compounds, which may be contained in at least one of the following layers: a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary layer, an electron blocking layer, a light emitting layer, an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. Such at least two compounds may be contained in the same layer or in different layers, and may be mixed-evaporated or co-evaporated, or may be evaporated individually.
Herein, "a plurality of host materials" means a host material comprising a combination of at least two compounds, which may be contained in any light emitting layer constituting an organic electroluminescent device. It may mean both a material before being contained in the organic electroluminescent device (e.g., before vapor deposition) and a material after being contained in the organic electroluminescent device (e.g., after vapor deposition). For example, the plurality of host materials of the present disclosure may be a combination of at least two host materials, and optionally, it may further comprise conventional materials included in an organic electroluminescent material. At least two compounds included in the plurality of host materials of the present disclosure may be included together in one light emitting layer by a method used in the art, or may be each included in a separate light emitting layer. For example, such at least two compounds may be evaporated in a mixture or co-evaporation, or may be evaporated individually.
Herein, the term "multiple host materials" means a host material comprising a combination of at least two compounds, which may be contained in any light emitting layer constituting an organic electroluminescent device. It may mean both a material before being contained in the organic electroluminescent device (e.g., before vapor deposition) and a material after being contained in the organic electroluminescent device (e.g., after vapor deposition). The various host materials of the present disclosure may be included in any light emitting layer constituting an organic electroluminescent device. At least two compounds contained in a plurality of host materials may be contained together in one light-emitting layer, or may be contained in separate light-emitting layers each. When at least two host materials are contained in one light emitting layer, the at least two host materials may be mixed and evaporated to form a layer, or may be separately and simultaneously co-evaporated to form a layer.
Herein, "(C1-C30) alkyl" means a straight or branched alkyl group having 1 to 30 carbon atoms constituting a chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. Herein, the term "(C3-C30) cycloalkyl" means a mono-or polycyclic hydrocarbon having from 3 to 30 ring backbone carbon atoms, wherein the number of carbon atoms is preferably from 3 to 20, and more preferably from 3 to 7. The cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, and the like. Herein, "(C6-C30) (arylene)" is used "Is a monocyclic or fused ring group derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, wherein the number of ring backbone carbon atoms is preferably 6 to 20, more preferably 6 to 15, which may be partially saturated and may comprise a spiro structure. Examples of aryl groups are in particular phenyl, biphenyl, terphenyl, tetrabiphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, phenanthryl, benzophenanthryl, phenylphenanthryl, anthracenyl, benzanthrenyl, indenyl, triphenylenyl, pyrenyl, naphthacene, perylenyl, Radical, benzo->Radicals, naphthaceneyl (napthoxyl), fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro [ fluorene-fluorene ]]Base, spiro [ fluorene-benzofluorene ]]A group, azulenyl (azulenyl), tetramethyl-dihydrophenanthryl, and the like. More specifically, the process is carried out, the aryl group may be o-tolyl, m-tolyl, p-tolyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-tert-butylphenyl, p- (2-phenylpropyl) phenyl, 4 '-methylbiphenyl, 4' -tert-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 para-terphenyl-2-yl, meta-tetrabiphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-dimethyl-1-fluorenyl, 9-dimethyl-2-fluorenyl, 9-dimethyl-3-fluorenyl, 9-dimethyl-4-fluorenyl 9, 9-diphenyl-1-fluorenyl, 9-diphenyl-2-fluorenyl, 9-diphenyl-3-fluorenyl, 9-diphenyl-4-fluorenyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1- & lt- & gt >Radix, 2- & lt- & gt>Radix, 3->Radix, 4->Radix, 5- & lt- & gt>Radix, 6- & lt- & gt>Radical, benzo [ c ]]Phenanthryl, benzo [ g ]]/>1-triphenylene, 2-triphenylene, 3-triphenylene, 4-triphenylene, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, 11-dimethyl-1-benzo [ a ]]Fluorenyl, 11-dimethyl-2-benzo [ a ]]Fluorenyl, 11-dimethyl-3-benzo [ a ]]Fluorenyl, 11-dimethyl-4-benzo [ a ]]Fluorenyl, 11-dimethyl-5-benzo [ a ]]Fluorenyl, 11-dimethyl-6-benzo [ a ]]Fluorenyl, 11-dimethyl-7-benzo [ a ]]Fluorenyl, 11-dimethyl-8-benzo [ a ]]Fluorenyl, 11-dimethyl-9-benzo [ a ]]Fluorenyl, 11-dimethyl-10-benzo [ a ]]Fluorenyl, 11-dimethyl-1-benzo [ b ]]Fluorenyl, 11-dimethyl-2-benzo [ b ]]Fluorenyl, 11-dimethyl-3-benzo [ b ]]Fluorenyl, 11-dimethyl-4-benzo [ b ]]Fluorenyl, 11-dimethyl-5-benzo [ b ]]Fluorenyl, 11-dimethyl-6-benzo [ b ]]Fluorenyl, 11-dimethyl-7-benzo [ b ]]Fluorenyl, 11-dimethyl-8-benzo [ b ]]Fluorenyl, 11-dimethyl-9-benzo [ b ]]Fluorenyl, 11-dimethyl-10-benzo [ b ]]Fluorenyl, 11-dimethyl-1-benzo [ c ]]Fluorenyl, 11-dimethyl-2-benzo [ c ]]Fluorenyl, 11-dimethyl-3-benzo [ c ] ]Fluorenyl, 11-dimethyl-4-benzo [ c ]]Fluorenyl, 11-dimethyl-5-benzo [ c ]]Fluorenyl, 11-dimethyl-6-benzo [ c ]]Fluorenyl group11, 11-dimethyl-7-benzo [ c ]]Fluorenyl, 11-dimethyl-8-benzo [ c ]]Fluorenyl, 11-dimethyl-9-benzo [ c ]]Fluorenyl, 11-dimethyl-10-benzo [ c ]]Fluorenyl, 11-diphenyl-1-benzo [ a ]]Fluorenyl, 11-diphenyl-2-benzo [ a ]]Fluorenyl, 11-diphenyl-3-benzo [ a ]]Fluorenyl, 11-diphenyl-4-benzo [ a ]]Fluorenyl, 11-diphenyl-5-benzo [ a ]]Fluorenyl, 11-diphenyl-6-benzo [ a ]]Fluorenyl, 11-diphenyl-7-benzo [ a ]]Fluorenyl, 11-diphenyl-8-benzo [ a ]]Fluorenyl, 11-diphenyl-9-benzo [ a ]]Fluorenyl, 11-diphenyl-10-benzo [ a ]]Fluorenyl, 11-diphenyl-1-benzo [ b ]]Fluorenyl, 11-diphenyl-2-benzo [ b ]]Fluorenyl, 11-diphenyl-3-benzo [ b ]]Fluorenyl, 11-diphenyl-4-benzo [ b ]]Fluorenyl, 11-diphenyl-5-benzo [ b ]]Fluorenyl, 11-diphenyl-6-benzo [ b ]]Fluorenyl, 11-diphenyl-7-benzo [ b ]]Fluorenyl, 11-diphenyl-8-benzo [ b ]]Fluorenyl, 11-diphenyl-9-benzo [ b ]]Fluorenyl, 11-diphenyl-10-benzo [ b ]]Fluorenyl, 11-diphenyl-1-benzo [ c ]]Fluorenyl, 11-diphenyl-2-benzo [ c ] ]Fluorenyl, 11-diphenyl-3-benzo [ c ]]Fluorenyl, 11-diphenyl-4-benzo [ c ]]Fluorenyl, 11-diphenyl-5-benzo [ c ]]Fluorenyl, 11-diphenyl-6-benzo [ c ]]Fluorenyl, 11-diphenyl-7-benzo [ c ]]Fluorenyl, 11-diphenyl-8-benzo [ c ]]Fluorenyl, 11-diphenyl-9-benzo [ c ]]Fluorenyl, 11-diphenyl-10-benzo [ c ]]Fluorenyl, 9, 10-tetramethyl-9, 10-dihydro-1-phenanthryl, 9, 10-tetramethyl-9, 10-dihydro-2-phenanthryl 9, 10-tetramethyl-9, 10-dihydro-3-phenanthryl, 9, 10-tetramethyl-9, 10-dihydro-4-phenanthryl, and the like. Herein, "(3-to 30-membered) (ene) heteroaryl" is an aryl group having 3 to 30 ring backbone atoms and comprising at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, si, P, se and Ge, wherein the number of ring backbone carbon atoms is preferably 3 to 30, and more preferably 5 to 20. The heteroaryl group may be a single ring or a condensed ring condensed with at least one benzene ring; and may be partially saturated. Further, the heteroaryl or heteroarylene described above herein may be a heteroaryl or heteroarylene formed by linking at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds, and may comprise a spiro structure. Examples of heteroaryl groups can in particular be Is a monocyclic heteroaryl group including furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and the like; and a fused-ring type heteroaryl group, including benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, benzobenzofuranoquinolinyl, benzofuranoquinazolinyl, benzofuranonaphthyridinyl, benzofuranopyrimidinyl, naphthofuranopyrimidinyl, benzothiophenoquinolinyl, benzothiophenoquinazolinyl, benzoquinolinyl, benzopyrimidinyl, benzoquinolinyl, and benzoquinolinyl benzothiophene naphthyridinyl, benzothiophene pyrimidinyl, naphthyridin pyrimidinyl, pyrimidoindolyl, benzopyrimidino indolyl, benzofuranopyrazinyl, naphtofuranopyrazinyl, benzothiophenopyrazinyl, naphthyridin opyrazinyl, pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzofuranpyrazinyl, benzofuranyl, benzoimidazolyl, benzoyl, benzoimidazolyl benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolicidinyl (indozidinyl), acridinyl, silafluorenyl (silafluoronyl), germofluorenyl (germofluorenyl), benzotriazolyl, phenazinyl, imidazopyridinyl, chromenoquinazolinyl, thiochromenyl, dimethylphenyl, indolocarbazolyl, indenocarbazolyl, and the like. More specifically, the heteroaryl group may be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 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-indolicidinyl, 2-indolicidinyl, 3-indolicidinyl, 5-indolicidinyl, 6-indolicidinyl, 7-indolicidinyl, 8-indolicidinyl, 2-imidazopyridinyl, 3-miazinyl Azolopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furanyl, 3-furanyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 5-benzofuranyl 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolinyl, 3-quinolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 1-isoquinolinyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl, 6-isoquinolinyl, 7-isoquinolinyl, 8-isoquinolinyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazol-1-yl, azacarbazol-2-yl, azacarbazol-3-yl, azacarbazol-4-yl, azacarbazol-5-yl, azacarbazol-6-yl, azacarbazol-7-yl, azacarbazol-8-yl, azacarbazol-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrolidin-1-yl, 2-methylpyrrolidin-3-yl, 2-methylpyrrolidin-4-yl, 2-methylpyrrolidin-5-yl, 3-methylpyrrolidin-1-yl, 3-methylpyrrolidin-2-yl, 3-methylpyrrolidin-4-yl, 3-methylpyrrolidin-5-yl, 2-tert-butylpyrrol-4-yl, 3- (2-phenylpropyl) pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothienyl, 2-dibenzothienyl, 3-dibenzothiophene Radical, 4-dibenzothienyl, 1-naphtho- [1,2-b]-benzofuranyl, 2-naphtho- [1,2-b]-benzofuranyl, 3-naphtho- [1,2-b]-benzofuranyl, 4-naphtho- [1,2-b]-benzofuranyl, 5-naphtho- [1,2-b]-benzofuranyl, 6-naphtho- [1,2-b]-benzofuranyl, 7-naphtho- [1,2-b]-benzofuranyl, 8-naphtho- [1,2-b]-benzofuranyl, 9-naphtho- [1,2-b]-benzofuranyl, 10-naphtho- [1,2-b]-benzofuranyl, 1-naphtho- [2,3-b]-benzofuranyl, 2-naphtho- [2,3-b]-benzofuranyl, 3-naphtho- [2,3-b]-benzofuranyl, 4-naphtho- [2,3-b]-benzofuranyl, 5-naphtho- [2,3-b]-benzofuranyl, 6-naphtho- [2,3-b]-benzofuranyl, 7-naphtho- [2,3-b]-benzofuranyl, 8-naphtho- [2,3-b]-benzofuranyl, 9-naphtho- [2,3-b]-benzofuranyl, 10-naphtho- [2,3-b]-benzofuranyl, 1-naphtho- [2,1-b]-benzofuranyl, 2-naphtho- [2,1-b]-benzofuranyl, 3-naphtho- [2,1-b]-benzofuranyl, 4-naphtho- [2,1-b]-benzofuranyl, 5-naphtho- [2,1-b]-benzofuranyl, 6-naphtho- [2,1-b]-benzofuranyl, 7-naphtho- [2,1-b]-benzofuranyl, 8-naphtho- [2,1-b]-benzofuranyl, 9-naphtho- [2,1-b ]-benzofuranyl, 10-naphtho- [2,1-b]-benzofuranyl, 1-naphtho- [1,2-b]-benzothienyl, 2-naphtho- [1,2-b]-benzothienyl, 3-naphtho- [1,2-b]-benzothienyl, 4-naphtho- [1,2-b]-benzothienyl, 5-naphtho- [1,2-b]-benzothienyl, 6-naphtho- [1,2-b]-benzothienyl, 7-naphtho- [1,2-b]-benzothienyl, 8-naphtho- [1,2-b]-benzothienyl, 9-naphtho- [1,2-b]-benzothienyl, 10-naphtho- [1,2-b]-benzothienyl, 1-naphtho- [2,3-b]-benzothienyl, 2-naphtho- [2,3-b]-benzothienyl, 3-naphtho- [2,3-b]-benzothienyl, 4-naphtho- [2,3-b]-benzothienyl, 5-naphtho- [2,3-b]-benzothienyl, 1-naphtho- [2,1-b]-benzothienyl, 2-naphtho- [2,1-b]-benzothienyl, 3-naphtho- [2,1-b]-benzothienyl, 4-naphtho- [2,1-b]-benzothienyl, 5-naphtho- [2,1-b]-benzothienyl, 6-naphtho- [2,1-b]-benzothienyl, 7-naphtho- [2,1-b]-benzothienyl, 8-naphtho- [2,1-b]-benzothienyl, 9-naphtho- [2,1-b]-benzothienyl, 10-naphtho- [2,1-b]-benzothienyl, 2-benzofuro [3,2-d ]]Pyrimidinyl, 6-benzofuro [3,2-d ]]Pyrimidinyl, 7-benzofurano[3,2-d]Pyrimidinyl, 8-benzofuro [3,2-d ] ]Pyrimidinyl, 9-benzofuro [3,2-d ]]Pyrimidinyl, 2-benzothieno [3,2-d ]]Pyrimidinyl, 6-benzothieno [3,2-d ]]Pyrimidinyl, 7-benzothieno [3,2-d ]]Pyrimidinyl, 8-benzothieno [3,2-d ]]Pyrimidinyl, 9-benzothieno [3,2-d ]]Pyrimidinyl, 2-benzofuro [3,2-d ]]Pyrazinyl, 6-benzofuro [3,2-d ]]Pyrazinyl, 7-benzofuro [3,2-d ]]Pyrazinyl, 8-benzofuro [3,2-d ]]Pyrazinyl, 9-benzofuro [3,2-d ]]Pyrazinyl, 2-benzothieno [3,2-d ]]Pyrazinyl, 6-benzothieno [3,2-d ]]Pyrazinyl, 7-benzothieno [3,2-d ]]Pyrazinyl, 8-benzothieno [3,2-d ]]Pyrazinyl, 9-benzothieno [3,2-d ]]Pyrazinyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germanofluorenyl, 2-germanofluorenyl, 3-germanofluorenyl, 4-germanofluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, and the like. Herein, the term "(C3-C30) aliphatic ring and condensed ring of (C6-C30) aromatic ring" means a ring formed by condensing at least one aliphatic ring having 3 to 30 ring skeleton carbon atoms with at least one aromatic ring having 6 to 30 ring skeleton carbon atoms, the number of carbon atoms in the aliphatic ring being preferably 3 to 25, more preferably 3 to 18, and the number of carbon atoms in the aromatic ring being preferably 6 to 25, more preferably 6 to 18. For example, the condensed ring may be a condensed ring of at least one benzene and at least one cyclohexane, or a condensed ring of at least one naphthalene and at least one cyclopentane, or the like. Herein, the carbon atoms in the fused rings of the (C3-C30) aliphatic ring and the (C6-C30) aromatic ring may be replaced by at least one heteroatom selected from B, N, O, S, si and P, preferably at least one heteroatom selected from N, O and S. The term "halogen" in this disclosure includes F, cl, br and I.
Further, "o", "m", and "p" mean substitution positions of all substituents. Ortho-positions are compounds having substituents adjacent to each other, for example at positions 1 and 2 on benzene. Meta is the next substitution position to the immediately adjacent substitution position, e.g., the compound has substituents at positions 1 and 3 on benzene. Para is the next substitution position in the meta position, e.g., the compound has substituents at positions 1 and 4 on benzene.
Herein, the term "ring formed by attachment to adjacent substituents" means a substituted or unsubstituted (3-to 30-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof formed by attachment or fusion of two or more adjacent substituents, preferably a substituted or unsubstituted (5-to 25-membered) monocyclic or polycyclic alicyclic ring, aromatic ring, or a combination thereof. Furthermore, the ring formed may comprise at least one heteroatom selected from the group consisting of B, N, O, S, si and P, preferably N, O and S. According to one embodiment of the present disclosure, the number of atoms in the ring backbone is 5 to 20; according to another embodiment of the present disclosure, the number of atoms in the ring backbone is 5 to 15. In one embodiment, the fused ring may be, for example, a benzofuropyridine ring, a benzothiophene 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 benzofluorene 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 a substituted or unsubstituted carbazole ring, or the like.
Further, the expression "substituted" in "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced with another atom or functional group (i.e., substituent), and is substituted with a group to which two or more substituents are attached among the substituents. For example, "a substituent in which two or more substituents are linked" may be pyridine-triazine. That is, the pyridine-triazine may be a heteroaryl group, or may be interpreted as one substituent in which two heteroaryl groups are linked. Preferably, the substituents of substituted alkyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted fused rings of aliphatic and aromatic rings, substituted mono-or di-alkylamino, substituted mono-or di-alkenylamino, substituted mono-or di-arylamino, substituted mono-or di-heteroarylamino, substituted alkylalkenylamino, substituted alkylarylamino, substituted alkylheteroarylamino, substituted alkenylarylamino, substituted alkenylheteroarylamino, and substituted arylheteroarylamino in the formulae of the present disclosure each independently represent at least one selected from the group consisting of: deuterium; halogen; cyano group; a carboxyl group; a nitro group; a hydroxyl group; (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; (3-to 30-membered) heteroaryl, unsubstituted or substituted by (C6-C30) aryl; (C6-C30) aryl unsubstituted or substituted with at least one of (C1-C30) alkyl and (3-to 30-membered) heteroaryl; tri (C1-C30) alkylsilyl; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; an amino group; mono-or di- (C1-C30) alkylamino; mono-or di- (C6-C30) arylamino; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; di (C6-C30) arylborocarbonyl; di (C1-C30) alkyl borocarbonyl; (C1-C30) alkyl (C6-C30) arylborocarbonyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl; for example, at least one selected from the following: deuterium, cyano, methyl, phenyl, naphthyl, biphenyl, phenanthryl, triphenylsilyl, fluorenyl, dibenzothienyl, dibenzofuranyl, and diphenylamino.
Hereinafter, a host material according to an embodiment will be described.
According to one embodiment, the plurality of host materials comprises a first host compound comprising at least one compound represented by formula 1 and a second host compound comprising at least one compound represented by formula 1.
According to one embodiment, the first host compound as a host material may be represented by the following formula 1.
In the formula (1) of the present invention,
x represents O, S, CR 11 R 12 、NR 13 Or Se;
R 11 to R 13 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; or may be attached to adjacent substituents to form one or more rings;
a represents a substituted or unsubstituted phenanthrene ring represented by the following formula 1-1;
in the formulae 1 and 1-1,
R 1 to R 4 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl,
Provided that R 1 To R 4 At least one of which is
L 1 And L 2 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (C3-C30) cycloalkylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 1 To Ar 5 Each independently represents a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
a and d are 1 to 4B and c are integers of 1 or 2, when a to d are integers of 2 or more, R 1 To R 4 Each of which may be the same or different; and is also provided with
* Represents the site of attachment to formula 1.
In one embodiment, X may be O or S.
In one embodiment, R 1 To R 4 Each independently of the others can be hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl,
In one embodiment, R 1 To R 4 At least one of them may be For example R 1 To R 4 At least two of (a) may be +.> For example R 1 To R 4 At least two of (a) may be +.>
In one embodiment, R 1 、R 2 And R is 4 At least one of them may be
In one embodiment, the removal ofIn addition, R 1 To R 4 Each independently may be hydrogen, deuterium, or a substituted or unsubstituted (C6-C30) aryl group, for example, hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted biphenyl group.
In one embodiment, L 1 And L 2 Each independently may be a single bond or a substituted or unsubstituted (C6-C30) arylene group, preferably a single bond, or a (C6-C25) arylene group that is unsubstituted or substituted with at least one of: deuterium; (C6-C30) aryl; and di (C6-C30) arylamino; more preferably a single bond, or a (C6-C18) arylene group, which is unsubstituted or substituted by at least one of the following: deuterium; (C6-C30) aryl; and di (C6-C30) arylamino. For example, L 1 And L 2 Each independently may be a single bond, or a phenylene group that is unsubstituted or substituted with at least one of: deuterium; a phenyl group; and a diphenylamino group.
In one embodiment, L 1 And L 2 May be a single bond.
In one embodiment, ar 1 To Ar 5 Each independently may be a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-to 30-membered) heteroaryl group, preferably a (C6-C25) aryl group that is unsubstituted or substituted with at least one of: deuterium; cyano group; (C6-C30) aryl; (5-to 30-membered) heteroaryl; and di (C6-C30) arylamino, or (5-to 25-membered) heteroaryl, which is unsubstituted or substituted with at least one of deuterium and (C6-C30) aryl, more preferably (C6-C25) aryl, which is unsubstituted or substituted with at least one of: deuterium; cyano group; (C6-C25) aryl; (5-to 25-membered) heteroaryl; and di (C6-C25) arylamino, or (5-to 18-membered) heteroaryl, unsubstituted or substituted with at least one of deuterium and (C6-C25) aryl. For example, ar 1 And Ar is a group 2 Each independently may be phenyl that is unsubstituted or substituted with at least one of: deuterium; a naphthyl group; phenylpropyl; a dimethylfluorenyl group; carbazolyl; a pyridyl group; dibenzofuranyl; dibenzothienyl; phenanthryl; triphenylsilyl; and a diphenylamino group, a phenyl group unsubstituted or substituted with a cyano group Or naphthyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, phenyl, unsubstituted or pyridyl; a biphenyl group; and phenanthryl which is unsubstituted or substituted by pyridyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted 9, 10-dihydrophenanthryl, substituted or unsubstituted o-tetrabiphenyl, substituted or unsubstitutedA group, an unsubstituted or phenyl-substituted pyridyl group, an unsubstituted or phenyl-substituted carbazolyl group, an unsubstituted or phenyl-substituted phenanthridinyl group, an unsubstituted or deuterium-or phenyl-substituted dibenzofuranyl group, an unsubstituted or phenyl-substituted dibenzothiophenyl group, a substituted or unsubstituted dibenzoselenophenyl group, or a substituted or unsubstituted naphthobenzoselenoyl group (nanobenzoselenonyl). For example, ar 3 To Ar 5 Each independently may be phenyl that is unsubstituted or substituted with at least one of: deuterium; cyano group; a pyridyl group; and a diphenylamino group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted p-biphenyl group, a substituted or unsubstituted m-biphenyl group, a substituted or unsubstituted o-biphenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted pyridyl group, a carbazolyl group which is unsubstituted or substituted by a phenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
According to one embodiment, the first host compound represented by formula 1 may be represented by the following formula I-1 or I-2.
In formulas I-1 and I-2,
X、R 1 to R 4 And a to d are as defined in formula 1.
According to one embodiment, the first host compound represented by formula 1 may be more specifically described by the following compounds, but is not limited thereto.
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According to one embodiment, the host compound represented by formula 1 may be prepared as shown in the following reaction scheme 1, but is not limited thereto, and may also be prepared by synthetic methods known to those skilled in the art.
Reaction scheme 1
In scheme 1, each substituent is as defined in formula 1.
As mentioned above, illustrative synthetic examples of the compounds represented by formula 1 are described, but they are based on Suzuki (Suzuki) cross-coupling reaction, wittig (Wittig) reaction, buchwald-Hartmax (Buchwald-Hartwig) cross-coupling reaction, miyaura) boronation reaction, N-arylation reaction, acidified montmorillonite (H-mont) mediated etherification reaction, intramolecular acid induced cyclization reaction, pd (II) catalyzed oxidative cyclization reaction, grignard (Grignard) reaction, heck (Heck) reaction, dehydrocyclization reaction, SN 1 Substitution reaction, SN 2 Substitution reaction, phosphine-mediated reductive cyclization reaction, and the like. Those skilled in the art will appreciate that the above reaction proceeds even if other substituents defined in formula 1 are bonded in addition to the substituents described in the specific synthetic examples.
According to one embodiment, the second host compound (which is another host material) may be composed of
Formula 2.
In the formula (2) of the present invention,
X 1 to X 3 Each independently represents N, CH or CD;
L 21 to L 23 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 21 to Ar 23 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, (C3-C30) aliphatic ring, and substituted or unsubstituted fused ring of (C6-C30) aromatic ring, or-N- (R') (R "); or may be attached to adjacent substituents to form one or more rings; and is also provided with
R 'and R' each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
In one embodiment, X 1 To X 3 Each independently may be N or CH.
In one embodiment, X 1 To X 3 At least one of them may be N, preferably X 1 To X 3 At least two of (a) may be N, more preferably X 1 To X 3 May be N.
In one ofIn embodiments, L 21 To L 23 Each independently may be a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (5-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. For example, L 21 To L 23 Each independently may be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted benzonaphthothiophene group, or a substituted or unsubstituted benzonaphthofuran group.
In one embodiment, ar 21 To Ar 23 Each independently may be a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (5-to 30-membered) heteroaryl group, or a substituted or unsubstituted tri (C6-C30) arylsilyl group, preferably a substituted or unsubstituted (C6-C25) aryl group, a substituted or unsubstituted (5-to 25-membered) heteroaryl group, or a substituted or unsubstituted tri (C6-C25) arylsilyl group, more preferably a substituted or unsubstituted (C6-C25) aryl group, a substituted or unsubstituted (5-to 18-membered) heteroaryl group, or a substituted or unsubstituted tri (C6-C18) arylsilyl group.
In one embodiment, ar 21 To Ar 23 At least one of which may be a substituted or unsubstituted (5-to 30-membered) heteroaryl group, preferably Ar 21 To Ar 23 May be substituted or unsubstituted (5-to 30-membered) heteroaryl.
In one embodiment, ar 21 To Ar 23 May be a substituted or unsubstituted (C6-C30) aryl group.
For example, ar 21 To Ar 23 Each independently of the otherCan be substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted triphenylgermyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzoselenophenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted benzophenanthryl, substituted or unsubstituted triphenylgermanium A group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted benzonaphthofuranyl group, a substituted or unsubstituted benzonaphtalenylthiophene group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzoxazolyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted naphthooxazolyl group, a substituted or unsubstituted benzonaphthazolyl group, a substituted or unsubstituted naphthazolyl group, a substituted or unsubstituted benzonaphthazolyl group, or a substituted or unsubstituted naphtazoimidazolyl group. Preferably Ar 21 To Ar 23 Each independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted p-biphenyl group, a substituted or unsubstituted m-biphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted triphenylsilyl group, a substituted or unsubstituted triphenylgermyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzoselenophenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted spirobifluor group Phenanthryl, substituted or unsubstituted ++>A group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted benzonaphthofuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted benzonaphthooxazolyl group, a substituted or unsubstituted benzonaphthothiazolyl group, or a substituted or unsubstituted naphthoselenazolyl group. Wherein the substituent of the substituted group may be at least one selected from the group consisting of: deuterium, cyano, methyl, phenyl, biphenyl, naphthyl, phenanthryl, triphenylsilyl, fluorenyl, dibenzothienyl and dibenzofuranyl.
According to one embodiment, ar 21 To Ar 23 At least one of them may be any one selected from the following formulas 2-1 to 2-17.
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In formulas 2-1 to 2-17,
t represents O, S, CR 17 R 18 、NR 19 Or Se;
Y 1 and Y 2 Each independently represents-N=, -NR 20 -, -O-, -S-or-Se-; provided that Y 1 And Y 2 Any of which is-n=, and Y 1 And Y 2 The other of (a) is-NR 20 -, -O-, -S-or-Se-;
R 1 to R 15 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl [ ] C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted fused rings of (C3-C30) aliphatic and (C6-C30) aromatic rings, or-N- (R') (R "); or may be attached to adjacent substituents to form one or more rings;
r 'and R' each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
R 17 to R 20 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group; or may be attached to adjacent substituents to form one or more rings;
L 8 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 8 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
a and d are integers from 1 to 5, b, e ', f, i and o ' are integers from 1 to 3, c, e, h, f ', l, i ' and o are integers from 1 to 4, d ' is an integer from 1 to 6, g, j, k, m and n ' are integers from 1 or 2, g ', j ', m ' and n are 1;
When a to m, o, d ' to f ', i ', n ' and o ' are integers of 2 or more, R 1 To R 15 Each of which may be the same or different; and is also provided with
* L in the expression and formula 2 21 To L 23 Is a ligation site of (2).
In one embodiment, T may be O, S, se, or CR 17 R 18 Wherein R is 17 And R is 18 Each independently may be a substituted or unsubstituted (C1-C30) alkyl group, or a substituted or unsubstituted (C6-C30) aryl group.
In one embodiment, Y 1 And Y 2 Any of which may be-n=, and Y 1 And Y 2 The other of them may be-O-, -S-or-Se-.
In one embodiment, R 1 To R 15 Each independently may be hydrogen, deuterium, cyano, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-to 30-membered) heteroaryl, or substituted or unsubstituted tri (C6-C30) arylsilyl, preferably hydrogen, deuterium, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (5-to 25-membered) heteroaryl, or substituted or unsubstituted tri (C6-C25) arylsilyl, more preferably hydrogen, deuterium, substituted or unsubstituted (C6-C18) aryl, substituted or unsubstituted (5-to 18-membered) heteroaryl, or substituted or unsubstituted tri (C6-C18) arylsilyl. For example, R 1 To R 15 Each independently may be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylsilyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, or substituted or unsubstituted benzonaphthooxazolyl.
In one embodiment, ar 8 May be a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-to 30-membered) heteroaryl group, preferably a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-to 25-membered) heteroaryl group, more preferably a substituted or unsubstituted (C6-C18) aryl group, or a substituted or unsubstituted (5-to 18-membered) heteroaryl group. For example, ar 8 May be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group. Wherein the substituent of the substituted group may be at least one selected from the group consisting of: deuterium, cyano, methyl, phenyl, triphenylsilyl and triphenylgermyl.
According to one embodiment, the second host compound represented by formula 2 may be more specifically described by the following compounds, but is not limited thereto.
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In the above compounds, dn means that n hydrogens are replaced with deuterium, where n represents an integer of 1 or more, and where the upper limit of n is determined by the number of hydrogens that may be substituted in each compound.
The host compound represented by formula 2 according to the present disclosure may be prepared by a synthetic method known to those skilled in the art, for example, by a synthetic method disclosed in reference to korean patent application laid-open No. 10-2020-0092879, or the like.
According to one embodiment, the plurality of host materials may further comprise at least one third host compound different from the first host compound and the second host compound.
According to one embodiment, the third host compound (which is a host material) may be represented by the following formula 4 or 5.
HAr′ 1 -L′ 4 -Ar′ 4 ---(5)
In the formulae 4 and 5,
L’ 1 to L' 4 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar’ 1 to Ar'. 4 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group; and is also provided with
HAr’ 1 Represents a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
In one embodiment, in formula 4, L' 1 To L' 3 Each independently may be a single bond, or a substituted or unsubstituted (C6-C30) arylene group, preferably a single bond, or a substituted or unsubstituted (C6-C25) arylene group, more preferably a single bond, or a substituted or unsubstituted (C6-C18) arylene group. For example, L' 1 To L' 3 Each independently may be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.
In one embodiment, in formula 4, ar' 1 To Ar'. 3 Each independently may be a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-to 30-membered) heteroaryl group, preferably a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-to 25-membered) heteroaryl group, more preferably a substituted or unsubstituted (C6-C18) aryl group, or a substituted or unsubstituted (5-to 25-membered) heteroaryl group. For example, ar' 1 To Ar'. 3 Each independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted p-biphenyl group, a substituted or unsubstituted m-biphenyl group, a substituted or unsubstituted o-biphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstitutedAlkenyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or nitrogen-containing substituted or unsubstituted 23 membered heteroaryl.
In one embodiment, in formula 4, ar' 1 To Ar'. 3 May be represented by the following formula 2-10, 2-13, or 2-18.
In formulas 2 to 10, 2 to 13 and 2 to 18,
Y 1 and Y 2 Each independently represents-N=, -NR 20 -, -O-, -S-or-Se-; provided that Y 1 And Y 2 Any of which is-n=, and Y 1 And Y 2 The other of (a) is-NR 20 -, -O-, -S-or-Se-;
R 9 to R 15 And R is 20 To R 24 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, (C3-C30) aliphatic ring, and substituted or unsubstituted fused ring of (C6-C30) aromatic ring, or-N- (R') (R "); or may be attached to adjacent substituents to form one or more rings;
r 'and R' each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
Ar 8 Represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
l, w and y are integers from 1 to 4; i. o' and z are integers from 1 to 3; j. k, m, n' and x are integers of 1 or 2;
when l, w, y, i, o ', z, j, k, m, n' and x are integers of 2 or more, R 9 To R 15 And R is 21 To R 24 Each of which may be the same or different; and is also provided with
* Represented by L 'in formula 4' 1 To L' 3 Is a ligation site of (2).
In one embodiment, in formula 4, ar' 1 To Ar'. 3 At least one of which may be represented by formulae 2 to 10.
In one embodiment, in formula 4, ar' 1 To Ar'. 3 At least one of which may be represented by formulae 2 to 13.
In one embodiment, in formula 5, L' 4 May be a single bond, or a substituted or unsubstituted (C6-C30) arylene group, preferably a single bond, or a substituted or unsubstituted (C6-C25) arylene group, more preferably a single bond, or a substituted or unsubstituted (C6-C18) arylene group. For example, L' 4 May be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.
In one embodiment, in formula 5, ar' 4 May be a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-to 30-membered) heteroaryl group, preferably a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-to 25-membered) heteroaryl group, more preferably a substituted or unsubstituted (C6-C18) aryl group, or a substituted or unsubstituted (5-to 18-membered) heteroaryl group. For example, ar' 4 May be a substituted or unsubstituted phenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted p-terphenyl group, or a substituted or unsubstituted dibenzofuranyl group.
HAr’ 1 Heteroaryl which may be substituted or unsubstituted (5-to 30-membered), preferably may be represented by formula 2-13 or 2-18, more preferably may be represented by formula 2-18, wherein is L 'in formula 5' 4 Is a ligation site of (2).
According to one embodiment, the third host compound represented by formula 4 or 5 may be more specifically described by the following compounds, but is not limited thereto.
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According to another embodiment of the present disclosure, the present disclosure provides an organic electroluminescent compound represented by the following formula 3.
In the case of the method of 3,
x represents O, S, CR 11 R 12 、NR 13 Or Se;
R 11 to R 13 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; or may be attached to adjacent substituents to form one or more rings;
R 1 to R 4 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, Provided that R 1 To R 4 At least one of which is +.>
L 1 And L 2 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (C3-C30) cycloalkylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 1 to Ar 5 Each independently represents a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3-to 30-membered) heteroaryl group; and is also provided with
a and d are integers of 1 to 4, b and c are integers of 1 or 2, and when a to d are integers of 2 or more, R 1 To R 4 Each of which may be the same or different;
* Represents a linkage site to formula 3;
with the proviso that the following compounds are excluded from formula 3.
According to one embodiment, the organic electroluminescent compound represented by formula 3 may be more specifically illustrated by the following compound, but is not limited thereto.
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Hereinafter, an organic electroluminescent device to which the above-described various host materials and/or organic electroluminescent compounds are applied will be described.
According to one embodiment, an 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 may include a light emitting layer, and the light emitting layer may include a plurality of host materials including at least one first host compound represented by formula 1 and at least one second host compound represented by formula 2. Wherein the weight ratio of the first host compound to the second host compound in the light emitting layer may be in the range of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, more preferably about 40:60 to about 60:40, and even more preferably may be about 50:50.
According to one embodiment, the plurality of host materials of the present disclosure may include at least one compound of the compounds H1-1 to H1-743 (which is a first host compound represented by formula 1) and at least one compound of the compounds H2-1 to H2-741 (which is a second host compound represented by formula 2). The plurality of host materials may be contained in the same organic layer, such as a light-emitting layer, or may be contained in different light-emitting layers, respectively.
According to another embodiment, the plurality of host materials according to the present disclosure may further comprise at least one third host compound different from the first host compound and the second host compound. For example, the various host materials according to the present disclosure may include at least one of the compounds H1-1 to H1-743 (which is a first host compound represented by formula 1), at least one of the compounds H2-1 to H2-741 (which is a second host compound represented by formula 2), and at least one of the compounds H3-1 to H3-60 (which is a third host compound represented by formula 4 or 5).
According to another embodiment, the organic electroluminescent compound represented by formula 3 may be included as a host material of the light emitting layer, a hole injection layer material, a hole transport layer material, a hole auxiliary layer material, a light emitting auxiliary layer material, or an electron blocking layer material.
The organic layer may further include at least one layer selected from the group consisting of: a hole injection layer, a hole transport layer, a hole assist layer, a light emitting assist layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, an electron blocking layer, and an electron buffer layer. In addition to the luminescent material according to the present disclosure, the organic layer may further comprise an amine-based compound and/or an azine-based compound. Specifically, the hole injection layer, the hole transport layer, the hole auxiliary layer, the light emitting auxiliary layer, or the electron blocking layer may contain an amine-based compound (for example, an arylamine-based compound, a styrylarylamine-based compound, or the like) as a hole injection material, a hole transport material, a hole auxiliary material, a light emitting auxiliary material, or an electron blocking material. In addition, the electron transport layer, the electron injection layer, the electron buffer layer, or the hole blocking layer may contain an azine-based compound as an electron transport material, an electron injection material, an electron buffer material, or a hole blocking material. In addition, the organic layer may further comprise at least one metal selected from the group consisting of: a metal of group 1 of the periodic table, a metal of group 2, a transition metal of group 4, a transition metal of group 5, an organometallic of a lanthanide and a d-transition element, or at least one complex compound comprising such a metal.
According to one embodiment, a variety of host materials may be used as the light emitting material for the white organic light emitting device. Depending on the arrangement of R (red), G (green), YG (yellow-green), or B (blue) light emitting units, a white organic light emitting device has proposed various structures such as a parallel side-by-side arrangement method, a stacked arrangement method, or a CCM (color conversion material) method, or the like. Furthermore, according to one embodiment, a variety of host materials may also be applied to an organic electroluminescent device including QDs (quantum dots).
One of the first electrode and the second electrode may be an anode, and the other may be a cathode. Wherein the 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 of a top emission type, a bottom emission type, or a two-side emission type according to the kind of material forming the first and second electrodes.
A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the light emitting layer. The hole injection layer may be a multilayer to lower a hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein each of the multilayer may use two compounds at the same time. In addition, the hole injection layer may be doped with a p-type dopant. Further, an electron blocking layer may be disposed between the hole transporting layer (or hole injecting layer) and the light emitting layer, and excitons may be confined within the light emitting layer by blocking electrons from overflowing from the light emitting layer to prevent light emission leakage. The hole transporting layer or the electron blocking layer may be a multilayer, and various compounds may be used for each layer.
An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light emitting layer and the cathode. The electron buffer layer may be a plurality of layers to control injection of electrons and improve interface characteristics between the light emitting layer and the electron injection layer, wherein each of the plurality of layers may use two compounds at the same time. A hole blocking layer may be placed between the electron transport layer (or electron injection layer) and the light emitting layer and block holes from reaching the cathode, thereby increasing the probability of recombination of electrons and holes in the light emitting layer. The hole blocking layer or the electron transporting layer may also be a multilayer, wherein each layer may use a plurality of compounds. In addition, the electron injection layer may be doped with an n-type 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. When the light-emitting auxiliary layer is placed between the anode and the light-emitting layer, it may be used to promote hole injection and/or hole transport, or to prevent electron overflow. When the light-emitting auxiliary layer is placed between the cathode and the light-emitting layer, it may be used to promote electron injection and/or electron transport, or to prevent hole overflow. In addition, a hole assist layer may be disposed between the hole transport layer (or hole injection layer) and the light emitting layer, and the hole transport rate (or hole injection rate) may be effectively promoted or limited, thereby enabling control of charge balance. When the organic electroluminescent device includes two or more hole transport layers, the further included hole transport layer may serve as a hole auxiliary layer or an electron blocking layer. The light emitting auxiliary layer, the hole auxiliary layer, or the electron blocking layer may have an effect of improving efficiency and/or lifetime of the organic electroluminescent device.
In the organic electroluminescent device of the present disclosure, at least one layer (hereinafter, "surface layer") selected from the group consisting of a chalcogenide layer, a halogenated metal layer, and a metal oxide layer may be preferably placed on an inner surface of one or both of a pair of electrodes. In particular, it is preferable to place a layer of chalcogenides (including oxides) of silicon and aluminum on the anode surface of the electroluminescent medium layer, and to place a layer of a metal halide or metal oxide on the cathode surface of the electroluminescent medium layer. Organic compoundThe operational stability of the electroluminescent device can be obtained by the surface layer. Preferably, the chalcogenide comprises SiO X (1≤X≤2)、AlO X (X is more than or equal to 1 and less than or equal to 1.5), siON, siAlON and the like; the halogenated metal comprises LiF, mgF 2 、CaF 2 Rare earth metal fluorides, etc.; and the metal oxide includes Cs 2 O、Li 2 O, mgO, srO, baO, caO, etc.
Further, in the organic electroluminescent device of the present disclosure, a mixed region of an electron transporting compound and a reducing dopant, or a mixed region of a hole transporting compound and an oxidizing dopant may be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anions, and thus injection and transport of electrons from the mixing region to the electroluminescent medium becomes easier. Furthermore, the hole transporting compound is oxidized to a cation, and thus injection and transport of holes from the mixed region to the electroluminescent medium become easier. Preferably, the oxidizing dopants include various lewis acids and acceptor compounds, and the reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, the reducing dopant layer may be used as a charge generation layer to prepare an organic electroluminescent device having two or more light emitting layers and emitting white light.
According to one embodiment, the organic electroluminescent device may further include at least one dopant in the light emitting layer. In one embodiment, the dopant compound may have a doping concentration of less than 20 wt% relative to the host material of the light emitting layer.
The dopant included in the organic electroluminescent device of the present disclosure may be at least one phosphorescent dopant or a fluorescent dopant, preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but may preferably be one or more metallized complex compounds of one or more metal atoms selected from the group consisting of: iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably one or more orthometalated complex compounds of one or more metal atoms selected from the group consisting of: iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably is one or more orthometalated iridium complex compounds.
The dopant included in the organic electroluminescent device of the present disclosure may use a compound represented by the following formula 101, but is not limited thereto.
In the case of the method 101,
l is selected from the following structures 1 to 3:
R 100 to R 103 Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium-and/or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-to 30-membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or may be attached to adjacent substituents to form one or more rings, for example with pyridine to form one or more rings, for example, substituted or unsubstituted quinoline, substituted or unsubstituted benzofuranopyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranoquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline;
R 104 to R 107 Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium-and/or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or may be attached to adjacent substituents to form one or more substituted or unsubstituted rings, e.g., with benzene to form one or more substituted or unsubstituted rings, substituted or unsubstituted rings Naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranopyridine, or substituted or unsubstituted benzothiophenopyridine;
R 201 to R 220 Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium-and/or halogen-substituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or substituted or unsubstituted (C6-C30) aryl; or may be attached to adjacent substituents to form one or more substituted or unsubstituted rings; and is also provided with
s represents an integer of 1 to 3.
In particular, specific examples of the dopant compound include the following, but are not limited thereto.
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In order to form each layer of the organic electroluminescent device of the present disclosure, a dry film forming method such as vacuum evaporation, sputtering, plasma, ion plating method, or the like, or a wet film forming method such as spin coating, dip coating, flow coating method, or the like may be used. When a wet film forming method is used, a thin film may be formed by dissolving or diffusing the material forming each layer into any suitable solvent (e.g., ethanol, chloroform, tetrahydrofuran, dioxane, etc.). The solvent may be any solvent in which the material forming each layer can be dissolved or diffused and which has no problem in terms of film forming ability.
When forming a layer by the first host compound and the second host compound according to one embodiment, the layer may be formed by the methods listed above, and may generally be formed by co-deposition or mixed deposition. Co-deposition is a hybrid deposition method in which two or more materials are placed in respective single crucible sources and an electric current is applied to both chambers simultaneously to evaporate the materials; and hybrid deposition is a method in which two or more materials are mixed in one crucible source before they are deposited and then an electric current is applied to one cell to evaporate the materials.
According to one embodiment, when the first host compound and the second host compound are present in the same layer or different layers in the organic electroluminescent device, the two host compounds may be formed separately. For example, after depositing the first host compound, a second host compound may be deposited.
According to one embodiment, the present disclosure may provide a display device including a plurality of host materials including a first host compound represented by formula 1 and a second host compound represented by formula 2. Further, by using the organic electroluminescent device of the present disclosure, a display device such as a smart phone, a tablet computer, a notebook computer, a PC, a TV, or a display device for a vehicle, or a lighting device such as outdoor or indoor lighting may be prepared.
Hereinafter, a method of preparing the organic electroluminescent compound according to the present disclosure will be explained with reference to a synthetic method of a representative compound or an intermediate compound in order to understand the present disclosure in detail.
EXAMPLE 1 Synthesis of Compound H1-52
Compound A-1 (5.4 g,17.88 mmol), compound 1 (5 g,14.90 mmol), tris (dibenzylideneacetone) dipalladium (0) (Pd) 2 (dba) 3 ) (0.68 g,0.745 mmol), sodium t-butoxide (NaOtBu) (2.1 g,22.36 mmol), S-phos (0.49 g,1.19 mmol) and 75mL o-xylene were added to the reaction vessel and then stirred under reflux for 1 hour. After the completion of the reaction, the reaction mixture was cooled to room temperature, filtered through celite, distilled under reduced pressure, and separated by column chromatography to obtain compound H1-52 (2.6 g, yield: 24%).
| MW | Melting point | |
| H1-52 | 601.6 | 238.4℃ |
EXAMPLE 2 Synthesis of Compound H1-144
1) Synthesis of Compound A-2
Compound A-1 (7 g,23.1 mmol), aniline (2.5 mL,27.7 mmol), pd 2 (dba) 3 (1.05g，1.1mmol)、Sphos(0.949g，2.3mmol), and NaOtBu (3.4 g,35.3 mmol) were added to the reaction vessel and dissolved in 115mL o-xylene, and then stirred under reflux for 1 hour. After the reaction was completed, the reaction mixture was washed with distilled water, and the organic layer was extracted with ethyl acetate and dried over magnesium sulfate, and the solvent was removed. Then, it was purified by column chromatography to obtain compound A-2 (4.4 g, yield: 53%).
2) Synthesis of Compound H1-144
Compound A-2 (4.4 g,12.2 mmol), compound 2 (4.76 g,14.6 mmol), pd 2 (dba) 3 (0.56 g,0.6 mmol), spos (0.502 g,1.2 mmol), and NaOtBu (1.76 g,18.3 mmol) were added to the reaction vessel and dissolved in 82mL of o-xylene, and then stirred under reflux for 1 hour. After the reaction was completed, the reaction mixture was washed with distilled water, and the organic layer was extracted with ethyl acetate and dried over magnesium sulfate, and the solvent was removed. Then, it was purified by column chromatography to obtain compound H1-144 (1.3 g, yield: 18%).
| MW | Melting point | |
| H1-144 | 602.74 | 197.4℃ |
EXAMPLE 3 Synthesis of Compound H1-145
Compound A-2 (6.7 g,18.64 mmol), compound 3 (8.9 g,22.36 mmol), pd 2 (dba) 3 (0.85 g,0.93 mmol), spos (0.76 g,1.86 mmol), and NaOtBu (2.7 g,27.96 mmol) were added to the reaction vessel and dissolved in 82mL of o-xylene, and then stirred under reflux for 1 hour. After the reaction was completed, the reaction mixture was washed with distilled water, and the organic layer was extracted with ethyl acetate and dried over magnesium sulfate, and the solvent was removed. Then, it was purified by column chromatography to obtain compound H1-145 (1.1 g, yield: 9%).
| MW | Melting point | |
| H1-145 | 678.8 | 186.5℃ |
EXAMPLE 4 Synthesis of Compound H1-65
Compound A-1 (5.7 g,18.95 mmol), compound 4 (6 g,14.58 mmol), pd 2 (dba) 3 (0.66 g,0.729 mmol), naOt-Bu (2.1 g,21.87 mmol), tri-tert-butylphosphine (P (t-Bu)) 3 ) (50%) (0.7 mL,1.458 mmol) and 75mL toluene were added to the reaction vessel, and then stirred under reflux for 1 hour. After the completion of the reaction, the reaction mixture,the reaction mixture was cooled to room temperature, filtered through celite, distilled under reduced pressure, and separated by column chromatography to obtain compound H1-65 (2.6 g, yield: 26%).
| MW | Melting point | |
| H1-65 | 677.7 | 234.4℃ |
EXAMPLE 5 Synthesis of Compound H1-88
Compound A-1 (5.7 g,18.95 mmol), compound 5 (6 g,14.58 mmol) Pd 2 (dba) 3 (0.66g，0.729mmol)、NaOt-Bu(2.1g，21.87mmol)、P(t-bu) 3 (50%) (0.7 mL,1.458 mmol) and 75mL toluene were added to the reaction vessel, and then stirred under reflux for 1 hour. After the completion of the reaction, the reaction mixture was cooled to room temperature, filtered through celite, distilled under reduced pressure, and separated by column chromatography to obtain compound H1-88 (4 g, yield: 40%).
| MW | Melting point | |
| H1-88 | 677.7 | 256.5℃ |
Hereinafter, a method of manufacturing an organic electroluminescent device including various host materials according to the present disclosure and device characteristics thereof will be explained in order to understand the present disclosure in detail.
Device examples 1 to 28 preparation of OLEDs co-deposited with a first host compound and a second host compound according to the present disclosure
An OLED according to the present disclosure was produced. First, a transparent electrode Indium Tin Oxide (ITO) thin film (10Ω/sq) (Ji Aoma limited (GEOMATEC co., ltd.), japan) on a glass substrate for OLED was subjected to ultrasonic washing with acetone and isopropyl alcohol in this order, and thereafter stored in isopropyl alcohol and then used. Thereafter, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Then, the compound HI-1 was introduced into one cell of the vacuum vapor deposition apparatus, and the compound HT-1 was introduced into the other cell. The two materials were evaporated at different rates and compound HI-1 was deposited at a doping amount of 3wt% based on the total of compounds HI-1 and HT-1 to form a hole injection layer having a thickness of 10 nm. Next, the compound HT-1 was deposited on the hole injection layer as a first hole transport layer having a thickness of 80 nm. Then, the compound HT-2 was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying a current to the cell, thereby forming a second hole transport layer having a thickness of 60nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light emitting layer is formed thereon as follows: the first and second host compounds described in Table 1 below were subjected to a second hosting Each of the compounds was introduced as a host into two cells of a vacuum vapor deposition apparatus, respectively, and compound D-39 was introduced as a dopant into the other cell. The two host materials were evaporated at a rate of 1:1, and the dopant materials were simultaneously evaporated at different rates, and deposited at a doping amount of 3wt% based on the total amount of host and dopant to form a light emitting layer having a thickness of 40nm on the second hole transport layer. Next, the compounds ET-1 and EI-1 were deposited as an electron transport material in a weight ratio of 50:50 to form an electron transport layer having a thickness of 35nm on the light emitting layer. After the compound EI-1 was deposited as an electron injection layer having a thickness of 2nm on the electron transport layer, an Al cathode having a thickness of 80nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED was produced. Each compound to be used for all materials was found to be at 10 -6 Purification by vacuum sublimation was performed under the tray.
Device example 29 preparation of an OLED co-deposited with a first host compound and a second host compound according to the present disclosure
An OLED was fabricated in the same manner as in device example 1, except that the first host compound and the second host compound were deposited at a ratio of 4:6 as host materials of the light emitting layer.
Comparative examples 1 to 8 preparation of OLED comprising conventional Compounds as a host
An OLED was fabricated in the same manner as in device example 1, except that the second host compound of table 1 below was used alone as a host of the light-emitting layer.
The driving voltage, the light emitting efficiency, and the light emitting color at a luminance of 1,000 nit, and the time taken for the luminance to decrease from 100% to 95% at a luminance of 10,000 nit of the OLED devices of device examples 1 to 29 and comparative examples 1 to 8 produced as described above were measured (lifetime: T95), and the results thereof are shown in table 1 below.
TABLE 1
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Device examples 30 to 35 preparation of OLEDs co-deposited with a first host compound, a second host compound, and a third host compound according to the present disclosure
An OLED was fabricated in the same manner as in device example 1, except that the first, second, and third host compounds shown in table 2 below were deposited at a ratio of 1:2:1 as the hosts of the light emitting layer.
The driving voltage, the light emitting efficiency, and the light emitting color at a luminance of 1,000 nits, and the time taken for the luminance to decrease from 100% to 95% at a luminance of 10,000 nits of the OLED devices of the device examples 30 to 35 produced as described above were measured (lifetime: T95), and the results thereof are shown in table 2 below.
TABLE 2
As can be seen from tables 1 and 2 above, the organic electroluminescent device comprising a specific combination of compounds according to the present disclosure as a host material exhibits low driving voltage and/or high luminous efficiency, and particularly significantly improved lifetime characteristics, compared to the organic electroluminescent device using only a single host material.
Device examples 36 to 38 preparation of OLEDs comprising compounds according to the present disclosure as second hole transport layer material
An OLED was fabricated in the same manner as in device example 1, except that the compounds of table 3 below were deposited as the material for the second hole transport layer and the first host compounds H1-88 and the second host compounds H2-739 were deposited as the hosts for the light emitting layers.
Comparative example 9 preparation of OLED comprising conventional Compounds as the second hole transport layer Material
An OLED was fabricated in the same manner as in device example 36, except that the compounds of table 3 below were deposited as the material for the second hole transport layer.
The driving voltages and power efficiencies at the luminance of 1,000 nits of the OLED devices of device examples 36 to 38 and comparative example 9 produced as described above were measured, and the results thereof are shown in table 3 below.
TABLE 3 Table 3
As can be seen from table 3 above, the organic electroluminescent device including the organic electroluminescent compound according to the present disclosure as a hole transport layer material has a lower driving voltage and/or higher power efficiency than the organic electroluminescent device including the conventional compound as a hole transport layer material.
The compounds used in the above device examples and comparative examples are shown in table 4 below:
TABLE 4 Table 4
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Claims (14)
1. A plurality of host materials comprising at least one first host compound and at least one second host compound, wherein the first host compound is represented by the following formula 1 and the second host compound is represented by the following formula 2:
wherein the method comprises the steps of
X represents O, S, CR 11 R 12 、NR 13 Or Se;
R 11 to R 13 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; or may be attached to adjacent substituents to form one or more rings;
a represents a substituted or unsubstituted phenanthrene ring represented by the following formula 1-1;
wherein the method comprises the steps of
R 1 To R 4 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl,Provided that R 1 To R 4 At least one of which is
L 1 And L 2 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (C3-C30) cycloalkylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 1 to Ar 5 Each independently represents a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
a and d are integers of 1 to 4, b and c are integers of 1 or 2, when a to d are integers of 2 or moreWhen R is 1 To R 4 Each of which may be the same or different; and is also provided with
* Represents a linking site with formula 1;
wherein the method comprises the steps of
X 1 To X 3 Each independently represents N, CH or CD;
L 21 to L 23 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 21 to Ar 23 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, (C3-C30) aliphatic ring, and substituted or unsubstituted fused ring of (C6-C30) aromatic ring, or-N- (R') (R "); or may be attached to adjacent substituents to form one or more rings; and is also provided with
R 'and R' each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
2. The plurality of host materials of claim 1, wherein the formula 1 is represented by the following formula I-1 or I-2:
wherein the method comprises the steps of
X、R 1 To R 4 And a to d are as defined in claim 1.
3. The plurality of host materials of claim 1, wherein Ar in formula 2 21 To Ar 23 Is represented by any one of the following formulas 2-1 to 2-17:
wherein the method comprises the steps of
T represents O, S, CR 17 R 18 、NR 19 Or Se;
Y 1 and Y 2 Each independently represents-N=, -NR 20 -, -O-, -S-or-Se-; provided that Y 1 And Y 2 Any of which is-n=, and Y 1 And Y 2 The other of (a) is-NR 20 -, -O-, -S-or-Se-;
R 1 to R 15 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, (C3-C30) aliphatic ring, and substituted or unsubstituted fused ring of (C6-C30) aromatic ring, or-N- (R') (R "); or may be attached to adjacent substituents to form one or more rings;
R 'and R' each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
R 17 to R 20 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group; or may be attached to adjacent substituents to form one or more rings;
L 8 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 8 represents a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
a and d are integers from 1 to 5, b, e ', f, i and o ' are integers from 1 to 3, c, e, h, f ', l, i ' and o are integers from 1 to 4, d ' is an integer from 1 to 6, g, j, k, m and n ' are integers from 1 or 2, g ', j ', m ' and n are 1;
when a to m, o, d ' to f ', i ', n ' and o ' are integers of 2 or more, R 1 To R 15 Each of which may be the same or different; and is also provided with
* L in the expression and formula 2 21 To L 23 Is a ligation site of (2).
4. The plurality of host materials of claim 1, wherein the compound represented by formula 1 is selected from the group consisting of:
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5. The plurality of host materials of claim 1, wherein the compound represented by formula 2 is selected from the group consisting of:
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wherein the method comprises the steps of
Dn means replacing n hydrogens with deuterium, where n represents an integer of 1 or more, where the upper limit of n is determined by the number of hydrogens that may be substituted in each compound.
6. An organic electroluminescent device comprising a first electrode; a second electrode; and at least one light emitting layer between the first electrode and the second electrode, wherein the at least one light emitting layer comprises the plurality of host materials of claim 1.
7. An organic electroluminescent compound represented by the following formula 3:
wherein the method comprises the steps of
X represents O, S, CR 11 R 12 、NR 13 Or Se;
R 11 to R 13 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; or may be attached to adjacent substituents to form one or more rings;
R 1 to R 4 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, Provided that R 1 To R 4 At least one of which is +.>
L 1 And L 2 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, a substituted or unsubstituted (C3-C30) cycloalkylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar 1 To Ar 5 Each independently represents a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3-to 30-membered) heteroaryl group; and is also provided with
a and d are integers of 1 to 4, b and c are integers of 1 or 2, and when a to d are integers of 2 or more, R 1 To R 4 Each of which may be the same or different;
* Represents a linkage site to formula 3;
with the proviso that the following compounds are excluded from formula 3.
8. The organic electroluminescent compound according to claim 7, wherein the compound represented by formula 3 is selected from the group consisting of:
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9. an organic electroluminescent device comprising the organic electroluminescent compound according to claim 7.
10. The plurality of host materials of claim 1, further comprising at least one third host compound different from the first host compound and the second host compound.
11. The plurality of host materials of claim 10, wherein the third host compound is represented by the following formula 4 or 5:
HAr′ 1 -L′ 4 -Ar′ 4 ---(5)
wherein the method comprises the steps of
L’ 1 To L' 4 Each independently represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Ar’ 1 to Ar'. 4 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group; and is also provided with
HAr’ 1 Represents a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
12. The plurality of host materials of claim 11, wherein Ar 'in formula 4' 1 To Ar'. 3 At least one of them is represented by the following formula 2-10, 2-13 or 2-18, or HAr 'in formula 5' 1 Represented by the following formulas 2 to 13 or 2 to 18:
wherein the method comprises the steps of
Y 1 And Y 2 Each independently represents-N=, -NR 20 -, -O-, -S-or-Se-; provided that Y 1 And Y 2 Any of which is-n=, and Y 1 And Y 2 The other of (a) is-NR 20 -, -O-, -S-or-Se-;
R 9 to R 15 And R is 20 To R 24 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstitutedSubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted fused ring of (C3-C30) aliphatic ring and (C6-C30) aromatic ring, or-N- (R') (R "); or may be attached to adjacent substituents to form one or more rings;
R 'and R' each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
Ar 8 represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group;
l, w and y are integers from 1 to 4; i. o' and z are integers from 1 to 3; j. k, m, n' and x are integers of 1 or 2;
when l, w, y, i, o ', z, j, k, m, n' and x are integers of 2 or more, R 9 To R 15 And R is 21 To R 24 Each of which may be the same or different; and is also provided with
* Represents L 'in formula 4 or 5' 1 To L' 4 Is a ligation site of (2).
13. The plurality of host materials of claim 10, wherein the third host compound is selected from the group consisting of:
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14. an organic electroluminescent device comprising a plurality of host materials according to claim 10.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2022-0075780 | 2022-06-21 | ||
| KR1020230059265A KR20230174704A (en) | 2022-06-21 | 2023-05-08 | A plurality of host materials and organic electroluminescent device comprising the same |
| KR10-2023-0059265 | 2023-05-08 |
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| Publication Number | Publication Date |
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| CN117263891A true CN117263891A (en) | 2023-12-22 |
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| CN (1) | CN117263891A (en) |
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