CN117384149A - Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same - Google Patents
Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same Download PDFInfo
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- CN117384149A CN117384149A CN202310681828.7A CN202310681828A CN117384149A CN 117384149 A CN117384149 A CN 117384149A CN 202310681828 A CN202310681828 A CN 202310681828A CN 117384149 A CN117384149 A CN 117384149A
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- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- WQPDQJCBHQPNCZ-UHFFFAOYSA-N cyclohexa-2,4-dien-1-one Chemical compound O=C1CC=CC=C1 WQPDQJCBHQPNCZ-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000011903 deuterated solvents Substances 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000007243 oxidative cyclization reaction Methods 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 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
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 125000003226 pyrazolyl 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
- 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
- 238000006476 reductive cyclization reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux 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
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-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
- 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
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K85/649—Aromatic compounds comprising a hetero atom
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K85/649—Aromatic compounds comprising a hetero atom
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/1018—Heterocyclic compounds
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Abstract
The present disclosure relates to various host materials, organic electroluminescent compounds, and organic electroluminescent devices including the same. By including the organic electroluminescent compounds according to the present disclosure as an organic electroluminescent material or by including a specific combination of the compounds according to the present disclosure as various host materials, an organic electroluminescent device having improved driving voltage, light emitting efficiency, and/or lifetime characteristics can be provided.
Description
Technical Field
The present disclosure relates to various organic host materials, organic electroluminescent compounds, and organic electroluminescent devices including the same.
Background
In 1987, tang et al, eastman Kodak, inc., by using a TPD/Alq composed of a light-emitting layer and a charge-transporting layer 3 The bilayer was first developed for small molecule green organic electroluminescent devices (OLEDs). Thereafter, the development of the OLED is rapidly completed and the OLED has been commercialized. Currently, OLEDs mainly use phosphorescent materials having excellent luminous efficiency in panel implementation. Accordingly, for long-term use and high resolution displays, OLEDs having high luminous efficiency and/or long lifetime are required.
In order to improve light emitting efficiency, driving voltage, and/or lifetime, various materials or concepts for an organic layer of an organic electroluminescent device have been proposed. However, they are not satisfactory in practical use. Accordingly, there is a continuing need to develop organic electroluminescent devices having more improved performance, such as improved driving voltage, light emitting efficiency, power efficiency and/or lifetime characteristics, compared to previously disclosed organic electroluminescent devices.
Meanwhile, korean patent application laid-open No. 2020-0035905 discloses a compound having the following structure: wherein benzoxazole or benzothiazole is bonded to pyrimidine or triazine as a basic backbone through a linkage. However, the foregoing references do not specifically disclose organic electroluminescent compounds and a variety of host materials comprising specific combinations of compounds as claimed herein. In addition, there is a need to develop materials with improved properties (e.g., low driving voltage, high luminous efficiency, and/or long life characteristics) compared to the compounds disclosed in the foregoing references.
Disclosure of Invention
Technical problem
It is an object of the present disclosure to provide improved host materials capable of providing organic electroluminescent devices having improved driving voltage, luminous efficiency and/or lifetime characteristics. It is another object of the present disclosure to provide an organic electroluminescent compound having a novel structure suitable for application to an organic electroluminescent device. It is still another object of the present disclosure to provide an organic electroluminescent device having improved driving voltage, light emitting efficiency and/or lifetime characteristics by including the compound of the present disclosure or a specific combination of the compounds of the present disclosure.
Solution to the problem
As a result of intensive studies to solve the above technical problems, the present inventors have found that the above object 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 wherein the second host compound is represented by the following formula 2. Furthermore, the present inventors have found that the above object can be achieved by the compound represented by the following formula 3.
In the formula (1) of the present invention,
x represents O or S;
R 1 to R 5 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or formula a below; provided that R 1 To R 5 Wherein at least one of the formulae a;
in the formula (a) of the formula (a),
L 1 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Y 1 to Y 3 Each independently represents N or CH; provided that Y 1 To Y 3 Wherein at least two of them represent N; and is also provided with
Ar 1 And Ar is a group 2 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;
in the formula (2) of the present invention,
A 1 And A 2 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group;
X 15 to X 18 Any one of which is combined with X 19 To X 22 Any one of which are connected to each other to form a single bond; and is also provided with
X not forming said single bond 11 To X 14 、X 23 To X 26 And X 15 To X 22 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; or may be attached to one or more adjacent substituents to form one or more rings.
In the case of the method of 3,
x' represents O or S;
R' 1 represents hydrogen, deuterium, or phenyl unsubstituted or substituted by deuterium;
R' 2 to R'. 5 Each independently represents hydrogen, deuterium, a substituted or unsubstituted (C6-C30) aryl group, or a' formula; provided that R 'is' 2 To R'. 5 Wherein at least one of the formulae a';
in the formula a' of the formula (a),
L' 1 represents a single bond, or a substituted or unsubstituted (C6-C30) arylene group;
Y' 1 to Y' 3 Each independently represents N or CH; provided that Y' 1 To Y' 3 Wherein at least two of them represent N;
Ar' 1 and Ar' 2 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group; provided that Ar' 1 And Ar' 2 Is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group; and is also provided with
Ar' 1 And Ar' 2 Different from each other.
The beneficial effects of the invention are that
A variety of host materials and organic electroluminescent compounds according to the present disclosure exhibit properties suitable for use in organic electroluminescent devices. Further, by including the organic electroluminescent compound according to the present disclosure as an organic electroluminescent material or by including a specific combination of compounds according to the present disclosure as a variety of host materials, an organic electroluminescent device having a lower driving voltage, higher luminous efficiency, and/or longer lifetime characteristics than conventional organic electroluminescent devices, and a display device or a light emitting device can be manufactured using the same, is provided.
Detailed Description
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure and is not meant to limit the scope of the present disclosure.
The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and can be contained in any layer constituting the organic electroluminescent device if necessary.
The term "organic electroluminescent material" in the present disclosure means a material that may be used in an organic electroluminescent device and may contain at least one compound. The organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device, if necessary. For example, the organic electroluminescent material may be a hole injecting material, a hole transporting material, a hole assisting material, a light emitting assisting material, an electron blocking material, a light emitting material (including host materials and dopant materials), an electron buffer material, a hole blocking material, an electron transporting material, an electron injecting material, or the like.
The term "host materials" in the present disclosure means one or more host materials 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 (e.g., before vapor deposition) and a material after (e.g., after vapor deposition) being included in the organic electroluminescent device. For example, the various host materials of the present disclosure may be a combination of two or more host materials, which may optionally further comprise conventional materials included in organic electroluminescent materials. Two or more compounds included in the plurality of host materials of the present disclosure may be included together in one light emitting layer, or may be included in different light emitting layers, respectively. For example, two or more host materials may be co-evaporated or co-evaporated, or may be evaporated individually.
In this context, the term "(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 10, and more preferably 1 to 6. The above alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, etc. The term "(C3-C30 Cycloalkyl "or" (C3-C30) cycloalkylene "means a mono-or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentylmethyl, cyclohexylmethyl, and the like. The term "(3-to 7-membered) heterocycloalkyl" means cycloalkyl having 3 to 7 ring backbone atoms and comprising at least one heteroatom selected from the group consisting of B, N, O, S, si and P, preferably O, S and N. The heterocycloalkyl group may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene, tetrahydropyran, and the like. The term "(C6-C30) aryl" or "(C6-C30) arylene" means a monocyclic or fused ring group derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms. The aryl and arylene groups described above may be partially saturated; and may include a screw structure. The aryl group may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, biphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, benzophenanthryl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, and the like, Radicals, naphthacenes (naphthalene radicals), fluoranthenes, spirobifluorenes, spiro [ fluorene-benzofluorene ]]Base, spiro [ cyclopentene-fluorene ]]Base, spiro [ indan-fluorene ]]A group, azulenyl group (azulenyl), tetramethyldihydrophenanthryl group, and the like. Specifically, the aryl group may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthracenyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthaceneyl, pyrenyl, 1->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, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzo [ a ]]Fluorenyl and benzo [ b ]]Fluorenyl and benzo [ c ]]Fluorenyl, dibenzofluorenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-tetrabiphenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, benzofluoranthenyl, 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, 9-dimethyl-1-fluorenyl, 9-dimethyl-2-fluorenyl 9, 9-dimethyl-3-fluorenyl, 9-dimethyl-4-fluorenyl, 9-diphenyl-1-fluorenyl, 9-diphenyl-2-fluorenyl 9, 9-diphenyl-3-fluorenyl, 9-diphenyl-4-fluorenyl, 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-dioMethyl-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, 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.
The term "(3-to 30-membered) heteroaryl" or "(3-to 30-membered) heteroarylene" means an aryl or arylene 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 and P. The heteroaryl group may be a single ring or a condensed ring condensed with at least one benzene ring; may be partially saturated; a heteroaryl group may be formed by linking at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds; and may include a screw structure. The heteroaryl group may include monocyclic heteroaryl groups such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and the like; a condensed ring type heteroaryl group, such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, dibenzoselenophenyl, naphthobenzofuranyl, naphthobenzothiophenyl, benzofuranquinolinyl, benzobenzofuranquinazolinyl, benzofurannaphthyridinyl, benzofuranpyrimidinyl, naphthofuranpyrimidinyl, benzothiophenoquinolinyl, benzothiophenoquinazolinyl, benzothiophennaphthyridinyl, benzothiophenopyrimidinyl, naphthothiophenopyrimidinyl, pyrimidoindolyl, benzopyrimidindolinyl, benzofuranpyrazinyl, naphthofuranpyrazinyl, benzothiophenpyrazinyl, naphthothiophenopyrazinyl, benzofuranpyrimidinyl, benzofurannaphthyridinyl, benzofuranpyrimidinyl, benzofuranpyrazinyl, benzofuranyl, and benzofuranpyrazinyl pyrazinoindolyl, benzopyrazinoindolyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl, benzotriazolyl, phenazinyl, imidazopyridinyl, chromenoquinazolinyl, thiochromenoquinazolinyl, dimethylbenzopyrimidinyl, indolocarzolyl, indenocarzolyl, and the like. More specifically, the process is carried out, heteroaryl groups may include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-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-indolyledinyl (indolidinyl), 2-indolyledinyl, 3-indolyledinyl, 5-indolyledinyl, 6-indolyledinyl, 7-indolyledinyl, 8-indolyledinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 3-pyridinyl, 4-pyridinyl, 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, 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, azacarbazolyl-1-yl azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-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, 2-oxadiazolyl, 5-oxadiazolyl, 4-phenanthridinyl, 1-phenanthridinyl, 2-oxazolyl, 5-oxadiazolyl, and the like, 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-phenylpyrrolidin-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-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzo-3-benzofuranyl, 2-dibenzo- [ 2-benzo-3-benzofuranyl ] -2, 2-b ] -2-benzofuranyl, 2-b-naphtalenyl 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- [2,3-b ] -benzofuranyl, 2-b ] -benzofuranyl, 4-naphtho- [2,3-b ] -benzofuranyl, 1-naphtho-b-benzofuranyl, 1-naphtho-2-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, 3-napht- [2, 3-naphteno- [2,3-b ] -benzothienyl, 3-naphteno- [1,2-b ] -benzothienyl, 3-napht-naphteno-b-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-benzofuro [3,2-d ] pyrimidinyl, 8-benzofuro [3,2-d ] pyrimidinyl, 9-benzofuro [3,2-d ] pyrimidinyl, 2-benzothio [3,2-d ] pyrimidinyl, 6-benzothio [3,2-d ] pyrimidinyl, 7-benzothio [3,2-d ] pyrimidinyl, 8-benzothio [3,2-d ] pyrimidinyl, 9-benzothio [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-benzothio [3,2-d ] pyrazinyl, 6-benzothio [3,2-d ] pyrazinyl, 7-benzothio [3,2-d ] pyrazinyl, 8-benzothio [3,2-d ] pyrazinyl, 9-benzothio [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. In the present disclosure, "halogen" includes F, cl, br and I.
In addition, "ortho (o-)", "meta (m-)", and "para (p-)" are prefixes, respectively representing the relative positions of substituents. Ortho means that two substituents are adjacent to each other and are referred to as ortho, for example, when two substituents in the benzene derivative occupy positions 1 and 2. Meta-position means that two substituents are at positions 1 and 3 and is referred to as meta-position, for example, when two substituents in the benzene derivative occupy positions 1 and 3. Para represents two substituents at positions 1 and 4, and is referred to as para, for example, when two substituents in the benzene derivative occupy positions 1 and 4.
The term "ring formed by the connection of adjacent substituents" means that at least two adjacent substituents are connected or fused to each other to form a substituted or unsubstituted mono-or polycyclic (3-to 30-membered) alicyclic or aromatic ring, or a combination thereof. The ring may preferably be a substituted or unsubstituted mono-or polycyclic (3-to 26-membered) alicyclic ring or aromatic ring, or a combination thereof, more preferably a mono-or polycyclic (5-to 25-membered) aromatic ring that is unsubstituted or substituted with at least one of one or more (C6-C18) aryl groups and one or more (3-to 20-membered) heteroaryl groups. Furthermore, the ring formed may contain at least one heteroatom selected from B, N, O, S, si and P, preferably at least one heteroatom selected from N, O and S. For example, the ring may be a benzene ring, a cyclopentane ring, an indane ring, a fluorene ring, a phenanthrene ring, an indole ring, a carbazole ring, a xanthene ring, or the like.
The expression "substituted" in "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced with another atom or another functional group (i.e., substituent), and also includes that a hydrogen atom is replaced with a group formed by the connection of two or more substituents among the above-mentioned substituents. For example, the "group formed by the linkage of two or more substituents" may be pyridine-triazine. That is, pyridine-triazine may be interpreted as a heteroaryl substituent or a substituent in which two heteroaryl substituents are linked. In the present disclosure, one or more substituents of the substituted alkyl, substituted (arylene), substituted (heteroarylene), substituted dibenzofuranyl, substituted dibenzothiophenyl, and substituted carbazolyl are each independently at least one selected from the group consisting of: deuterium; halogen; cyano group; a carboxyl group; a nitro group; a hydroxyl group; phosphine oxide; (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; a (3-to 30-membered) heteroaryl group that is unsubstituted or substituted with at least one of deuterium and one or more (C6-C30) aryl groups; (C6-C30) aryl, unsubstituted or substituted with deuterium; 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- (C2-C30) alkenylamino; mono-or di- (C6-C30) arylamino; mono-or di- (3-to 30-membered) heteroarylamino; (C1-C30) alkyl (C2-C30) alkenylamino; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkyl (3-to 30-membered) heteroarylamino; (C2-C30) alkenyl (C6-C30) arylamino; (C2-C30) alkenyl (3-to 30-membered) heteroarylamino; (C6-C30) aryl (3-to 30-membered) heteroarylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; (C6-C30) arylphosphines; 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. According to one embodiment of the present disclosure, the one or more substituents are each independently at least one selected from the group consisting of: deuterium; (6-to 25-membered) heteroaryl, unsubstituted or substituted with at least one of deuterium and one or more (C6-C18) aryl; and unsubstituted or deuterium-substituted (C6-C28) aryl. According to another embodiment of the present disclosure, the one or more substituents are each independently at least one selected from the group consisting of: deuterium; (6-to 20-membered) heteroaryl, unsubstituted or substituted with at least one of deuterium and one or more (C6-C12) aryl; and unsubstituted or deuterium-substituted (C6-C20) aryl. For example, the one or more substituents may each independently be at least one selected from the group consisting of: deuterium, phenyl, biphenyl, terphenyl, naphthyl, triphenylene, dibenzofuranyl, dibenzothiophenyl, and carbazolyl that is unsubstituted or substituted with one or more phenyl groups, wherein the substituents may be further substituted with deuterium.
A plurality of host materials according to the present disclosure include a first host material and a second host material, wherein the first host material includes at least one compound represented by formula 1, and the second host material includes at least one compound represented by formula 2.
Hereinafter, the compound represented by formula 1 will be described in more detail.
In formula 1, X represents O or S.
In formula 1, R 1 To R 5 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or formula a; provided that R 1 To R 5 Is represented by formula a. According to one embodiment of the present disclosure, R 1 To R 5 Each independently of the otherRepresents hydrogen; deuterium; (C6-C30) aryl, unsubstituted or substituted with at least one of deuterium and one or more (C6-C30) aryl; or formula a. According to another embodiment of the disclosure, R 1 To R 5 Each independently represents hydrogen; deuterium; (C6-C18) aryl, unsubstituted or substituted with deuterium; or formula a. According to yet another embodiment of the disclosure, R 1 To R 5 Any one of the formulae a, and the others each independently represent hydrogen; deuterium; or an unsubstituted or deuterium-substituted (C6-C12) aryl group. For example, R 1 To R 5 Each independently may represent hydrogen, deuterium, phenyl unsubstituted or substituted with deuterium, formula a, or the like; provided that R 1 To R 5 At least one of which is of formula a.
L 1 Represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group. According to one embodiment of the present disclosure, L 1 Represents a single bond or a (C6-C30) arylene group which is unsubstituted or substituted by at least one of deuterium and one or more (C6-C30) aryl groups. According to another embodiment of the present disclosure, L 1 Represents a single bond or a (C6-C20) arylene group which is unsubstituted or substituted by at least one of deuterium and one or more (C6-C20) aryl groups. For example, L 1 May represent a single bond, a phenylene group unsubstituted or substituted with one or more phenyl groups, a biphenylene group unsubstituted or substituted with one or more phenyl groups, a terphenylene group, or the like, which may be further substituted with deuterium.
Y 1 To Y 3 Each independently represents N or CH; provided that Y 1 To Y 3 And at least two of them represent N. For example, Y 1 To Y 3 Wherein two of the two represent N and the other represents CH; or Y 1 To Y 3 All represent N.
Ar 1 And Ar is a group 2 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. According to one embodiment of the present disclosure, ar 1 And Ar is a group 2 Each independently represents unsubstituted or deuterium-substituted, one or more (C6-C30) aryl groups and oneAt least one substituted (C6-C30) aryl group of one or more (3-to 30-membered) heteroaryl groups; or a (3-to 30-membered) heteroaryl group which is unsubstituted or substituted with at least one of deuterium and one or more (C6-C30) aryl groups. According to another embodiment of the present disclosure, ar 1 And Ar is a group 2 Each independently represents a (C6-C25) aryl group unsubstituted or substituted with at least one of deuterium, one or more (C6-C20) aryl groups, and one or more (6-to 20-membered) heteroaryl groups; or a (6-to 15-membered) heteroaryl group which is unsubstituted or substituted with at least one of deuterium and one or more (C6-C15) aryl groups. Specifically, ar 1 And Ar is a group 2 Each independently may be phenyl unsubstituted or substituted with one or more dibenzofuranyl groups, one or more dibenzothiophenyl groups, one or more carbazolyl groups, or one or more 9-phenylcarbazolyl groups; a biphenyl group; a terphenyl group; a tetrabiphenyl group; a naphthyl group; phenyl naphthyl; a naphthylphenyl group; a pyridyl group; pyrimidinyl; triazinyl; dibenzofuranyl, unsubstituted or substituted with one or more phenyl groups; dibenzothienyl, unsubstituted or substituted with one or more phenyl groups; or a carbazolyl group unsubstituted or substituted with at least one of one or more phenyl groups and one or more biphenyl groups, which groups may be further substituted with at least one deuterium. For example, ar 1 And Ar is a group 2 Each independently may be phenyl unsubstituted or substituted with one or more dibenzofuranyl groups, one or more dibenzothiophenyl groups, one or more carbazolyl groups, or one or more 9-phenylcarbazolyl groups; a biphenyl group; a terphenyl group; dibenzofuranyl, unsubstituted or substituted with one or more phenyl groups; dibenzothienyl, unsubstituted or substituted with one or more phenyl groups; or a carbazolyl group unsubstituted or substituted with at least one of one or more phenyl groups and one or more biphenyl groups, which groups may be further substituted with at least one deuterium.
Hereinafter, the compound represented by formula 2 will be described in more detail.
In formula 2, A 1 And A 2 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiopheneA group, or a substituted or unsubstituted carbazolyl group. According to one embodiment of the present disclosure, A 1 And A 2 Each independently represents a substituted or unsubstituted (C6-C25) aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group, and one or more substituents thereof may each independently be at least one of deuterium, (C6-C30) aryl group, and (3-to 30-membered) heteroaryl group. According to another embodiment of the present disclosure, A 1 And A 2 Each independently represents a (C6-C25) aryl group unsubstituted or substituted with at least one of deuterium, one or more (C6-C18) aryl groups, one or more dibenzofuranyl groups, one or more dibenzothienyl groups, and one or more carbazolyl groups; dibenzofuranyl, unsubstituted or substituted with at least one of deuterium and one or more (C6-C18) aryl groups; dibenzothienyl, unsubstituted or substituted with at least one of deuterium and one or more (C6-C18) aryl groups; or a carbazolyl group unsubstituted or substituted with at least one of deuterium and one or more (C6-C18) aryl groups. Specifically, A 1 And A 2 Each independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzothiophenyl group. For example, A 1 And A 2 Each independently may be phenyl that is unsubstituted or substituted with one or more naphthyl, one or more triphenylene, one or more dibenzofuranyl, or one or more dibenzothiophenyl; a biphenyl group; a naphthyl group; a naphthylphenyl group; phenyl naphthyl; a terphenyl group; triphenylene; dibenzofuranyl, unsubstituted or substituted with one or more phenyl groups; dibenzothienyl, unsubstituted or substituted with one or more phenyl groups; or carbazolyl substituted with one or more phenyl groups or one or more naphthyl groups, which groups may be further substituted with deuterium.
In formula 2, X 15 To X 18 Any one of which is combined with X 19 To X 22 Is connected to each other to form a single bond. X not forming said single bond 11 To X 14 、X 23 To X 26 And X 15 To X 22 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; or may be attached to one or more adjacent substituents to form one or more rings. For example, X 11 To X 26 Each independently may be hydrogen or deuterium.
According to one embodiment of the present disclosure, X 11 、X 18 、X 19 And X 26 At least one, preferably at least two, more preferably at least three, and still more preferably all, of which may be deuterium.
According to one embodiment of the present disclosure, X 11 To X 26 The deuterium substitution rate of (c) may be about 25% to about 100%, preferably about 35% to about 100%, more preferably about 45% to about 100%, and still more preferably about 55% to about 100%.
According to one embodiment of the present disclosure, formula 2 may be represented by at least one of the following formulas 2-1 to 2-8.
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In the formulae 2-1 to 2-8, A 1 、A 2 And X 11 To X 26 And their preferred embodiments are as defined in formula 2.
The compound represented by formula 1 may be at least one selected from the following compounds, but is not limited thereto.
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The compound represented by formula 2 may be at least one selected from the following compounds, but is not limited thereto.
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Of the compounds H2-1 to H2-144, D n Meaning that n numbers of hydrogens are replaced with deuterium. In formula 2, the deuterium substitution rate may be about 40% to about 100%, preferably about 50% to about 100%, more preferably about 60% to about 100%, and still more preferably about 70% to about 100%. When deuterated to a number equal to or greater than the lower limit, the bond dissociation energy resulting from deuteration increases to increase the stability of the compound, and when the compound is used in an organic electroluminescent device, the device may exhibit improved lifetime characteristics.
The combination of at least one of the compounds C-1 to C-255 with at least one of the compounds H2-1 to H2-280 may be used in an organic electroluminescent device.
Hereinafter, the compound represented by formula 3 will be described in more detail.
In formula 3, X' represents O or S.
In formula 3, R' 1 Represents hydrogen, deuterium, or phenyl which is unsubstituted or substituted by deuterium. According to one embodiment of the present disclosure, R' 1 Represents unsubstituted or deuterium-substituted benzeneA base.
In formula 3, R' 2 To R'. 5 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or formula a'; provided that R 'is' 2 To R'. 5 Is represented by formula a'. According to one embodiment of the present disclosure, R' 2 To R'. 5 Each independently represents hydrogen, deuterium or formula a'. According to another embodiment, R' 2 To R'. 5 Each of which independently represents formula a', and the others each independently represents hydrogen or deuterium.
L' 1 Represents a single bond, or a substituted or unsubstituted (C6-C30) arylene group. According to one embodiment of the present disclosure, L' 1 Represents a single bond or a (C6-C30) arylene group which is unsubstituted or substituted by at least one of deuterium and one or more (C6-C30) aryl groups. According to another embodiment of the present disclosure, L' 1 Represents a single bond or a (C6-C20) arylene group which is unsubstituted or substituted by at least one of deuterium and one or more (C6-C20) aryl groups. For example, L' 1 May represent a single bond, a phenylene group unsubstituted or substituted with one or more phenyl groups, a biphenylene group unsubstituted or substituted with one or more phenyl groups, or a terphenylene group, which may be further substituted with deuterium.
Y' 1 To Y' 3 Each independently represents N or CH; provided that Y' 1 To Y' 3 And at least two of them represent N. For example, Y' 1 To Y' 3 Is N and the other is CH; or Y' 1 To Y' 3 Are all N.
Ar' 1 And Ar' 2 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group; provided that Ar' 1 And Ar' 2 Represents a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group, and Ar' 1 And Ar' 2 Different from each other. According to one embodiment of the present disclosure, when Ar' 1 And Ar' 2 Each independently represents substitution orWhen an unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, they may each be selected from the group consisting of: substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, and substituted or unsubstituted dibenzothiophenyl. According to another embodiment of the present disclosure, ar' 1 And Ar' 2 Each independently represents an unsubstituted or deuterium-substituted (C6-C18) aryl group; carbazolyl that is unsubstituted or substituted with at least one of deuterium and one or more (C6-C20) aryl groups; dibenzofuranyl, unsubstituted or substituted with at least one of deuterium and one or more (C6-C18) aryl groups; or dibenzothienyl, unsubstituted or substituted with at least one of deuterium and one or more (C6-C18) aryl. For example, ar' 1 And Ar' 2 Each independently may represent a phenyl group, a biphenyl group, a terphenyl group, a dibenzofuranyl group unsubstituted or substituted with one or more phenyl groups, a dibenzothiophenyl group unsubstituted or substituted with one or more phenyl groups, or a carbazolyl group unsubstituted or substituted with at least one of one or more phenyl groups and one or more biphenyl groups, which groups may be further substituted with deuterium.
The compound represented by formula 3 may be at least one selected from the following compounds, but is not limited thereto.
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The compound represented by formula 1 according to the present disclosure may be prepared by synthetic methods known to those skilled in the art. For example, the compound represented by formula 1 may be prepared by referring to the following reaction schemes 1-1 and 1-2, and the compound represented by formula 3 according to the present disclosure may be prepared by referring to the following reaction scheme 1-1, but is not limited thereto.
[ reaction scheme 1-1]
[ reaction schemes 1-2]
In schemes 1-1 and 1-2, X, R 1 、Y 1 To Y 3 、L 1 、Ar 1 And Ar is a group 2 Is as defined in formula 1, and Hal means halogen.
The compound represented by formula 2 according to the present disclosure may be prepared by synthetic methods known to those skilled in the art. For example, the compound represented by formula 2 may be prepared by referring to the following reaction scheme 2, but is not limited thereto.
Reaction scheme 2
In reaction scheme 2, A 1 、A 2 And X 11 To X 26 Is as defined in formula 2, dn meansRefers to the substitution of n numbers of hydrogens with deuterium, n is an integer of 1 or greater, and the upper limit of n is the number of hydrogens in each compound.
Although illustrative synthetic examples of the compounds represented by formulas 1 to 3 are described above, those skilled in the art will readily understand that they are all based on a Buchwald-hartmash (Buchwald-Hartwig) cross-coupling reaction, an N-arylation reaction, an acidified montmorillonite (H-mont) mediated etherification reaction, a Miyaura) boronation reaction, a Suzuki cross-coupling reaction, an intramolecular acid-induced cyclization reaction, a Pd (II) -catalyzed oxidative cyclization reaction, a grignard reaction (Grignard Reaction), a Heck reaction (Heck reaction), a dehydrocyclization reaction, an SN1 substitution reaction, an SN2 substitution reaction, a phosphine-mediated reductive cyclization reaction, and the like, and that the above reactions proceed even when substituents defined in formulas 1 to 3 other than the substituents specified in the specific synthetic examples are bonded.
Furthermore, deuterated compounds having formulas 1-3 may be prepared in a similar manner using deuterated precursor materials or more commonly may be prepared by treating non-deuterated compounds with deuterated solvent D6-benzene in the presence of lewis acid H/D exchange catalysts such as aluminum trichloride or ethylaluminum chloride. In addition, the degree of deuteration can be controlled by varying the reaction conditions, such as the reaction temperature. For example, the number of deuterium in formulas 1 to 3 can be controlled by adjusting the reaction temperature and time, the equivalent of acid, and the like.
The present disclosure provides an organic electroluminescent compound represented by formula 3, an organic electroluminescent material comprising the organic electroluminescent compound represented by formula 3, and an organic electroluminescent device comprising the organic electroluminescent material. The organic electroluminescent material may consist only of the organic electroluminescent compounds of the present disclosure, and may further comprise conventional materials included in the organic electroluminescent material.
The organic electroluminescent device of the present disclosure includes an anode, a cathode, and at least one organic layer between the anode and the cathode, wherein the organic layer may include an organic electroluminescent material including a compound represented by formula 3.
The organic electroluminescent compound having formula 3 of the present disclosure may be included in at least one of a light emitting layer, a hole injection layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer, and may be preferably included in at least one of a light emitting layer, a hole transport layer, a hole auxiliary layer, a light emitting auxiliary layer, an electron transport layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer, if necessary. The organic electroluminescent compounds according to formula 3 of the present disclosure may be contained as a host material. If desired, the organic electroluminescent compounds of the disclosure can be used as co-host materials.
The present disclosure provides an organic electroluminescent device including an anode; a cathode; and at least one light emitting layer between the anode and the cathode, wherein the at least one light emitting layer comprises a plurality of host materials of the present disclosure. The first host material and the second host material of the present disclosure may be contained in one light emitting layer, or may be contained in different light emitting layers among a plurality of light emitting layers, respectively. The various host materials of the present disclosure may comprise the compound represented by formula 1 and the compound represented by formula 2 in a ratio of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, and more preferably about 30:70 to about 70:30. Further, the compound represented by formula 1 and the compound represented by formula 2 in a desired ratio may be combined by mixing them in a shaker, by dissolving them in a glass tube via heating, or by dissolving them in a solvent or the like.
According to one embodiment of the present disclosure, the dopant compound may have a doping concentration of less than 20wt% with respect to the host compound 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 fluorescent dopant, and is preferably a phosphorescent dopant. The phosphorescent dopant material applied to the organic electroluminescent device according to the present disclosure is not particularly limited, but may be selected from metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), preferably ortho-metallized complex compounds selected from iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and more preferably ortho-metallized iridium complex compounds.
The dopant included in the organic electroluminescent device of the present disclosure may be a compound represented by the following formula 101, but is not limited thereto.
In the case of the method 101,
l is any one selected from the following structures 1 to 3;
R 100 to R 103 Each independently represents hydrogen, deuterium, halogen, unsubstituted or deuterium-and/or one or more 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 together with pyridine one or more rings, such as substituted or unsubstituted quinoline, benzofuropyridine, benzothienopyridine, indenopyridine, benzofuroquinoline, benzothienoquinoline, or indenoquinoline;
R 104 To R 107 Each independently represents hydrogen, deuterium, halogen, unsubstituted or (C1-C30) alkyl substituted by deuterium and/or one or more halogens, 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 together with benzene one or more substituted or unsubstituted rings, for example, substituted or unsubstituted naphthalene, fluorene, dibenzothiophene, dibenzofuran, indenopyridine, benzofuropyridine, or benzothiophenopyridine;
R 201 to R 220 Each independently ofStand for hydrogen, deuterium, halogen, unsubstituted or (C1-C30) alkyl substituted by deuterium and/or one or more halogens, 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.
Specific examples of the dopant compounds are as follows, but are not limited thereto.
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The organic electroluminescent device of the present disclosure includes an anode; a cathode; and at least one organic layer between the anode and the cathode. The organic layer includes a light emitting layer, and may further include at least one layer selected from a hole injecting layer, a hole transporting layer, a hole assisting layer, a light emitting assisting layer, an electron transporting layer, an electron buffering layer, an electron injecting layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. Each of these layers may be further configured as multiple layers.
The anode and cathode may each be formed of a transparent conductive material, or a transflective or 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 type of materials forming the anode and the cathode. In addition, the hole injection layer may be further doped with one or more p-type dopants, and the electron injection layer may be further doped with one or more n-type dopants.
At least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound may be further included in the organic layer. In addition, the organic material layer may further include 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 the metal.
In addition, the organic electroluminescent device of the present disclosure may emit white light by further including at least one light emitting layer including a blue, red or green light emitting compound known in the art in addition to the compound of the present disclosure. Furthermore, it may further comprise a yellow or orange light emitting layer, if necessary.
In the organic electroluminescent device of the present disclosure, it is preferable that at least one layer (hereinafter referred to as a "surface layer") selected from the group consisting of a chalcogenide layer, a metal halide layer, and a metal oxide layer is disposed on at least one inner surface of a pair of electrodes. In particular, it is preferable to place a chalcogenide (including oxide) layer of silicon and aluminum on the anode surface on the electroluminescent medium layer side, and to place a metal halide layer or a metal oxide layer on the cathode surface on the electroluminescent medium layer side. The driving stability of the organic electroluminescent device can be obtained by the surface layer. Preferred examples of chalcogenides include SiO X (1≤X≤2)、AlO X (1.ltoreq.X.ltoreq.1.5), siON, siAlON, etc., preferred examples of the metal halide include LiF, mgF 2 、CaF 2 Rare earth metal fluorides, etc., and metalsPreferred examples of the oxide include Cs 2 O、Li 2 O, mgO, srO, baO, caO, etc.
A hole injection layer, a hole transport layer, or 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 so as to lower a hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer, wherein two compounds may be used simultaneously in each of the multilayer. The hole transport layer or the electron blocking layer may be a multilayer.
An electron buffer layer, a hole blocking layer, an electron transport layer, or 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 multilayer in order to control electron injection and improve interface characteristics between the light emitting layer and the electron injection layer, wherein two compounds may be simultaneously used in each of the multilayer. The hole blocking layer or the electron transporting layer may be a multilayer, wherein a plurality of compounds may be used in each of the multilayer.
The light emitting auxiliary layer may be a layer disposed between the anode and the light emitting layer or between the cathode and the light emitting layer. When placed between the anode and the light emitting layer, the light emitting auxiliary layer may be used to promote hole injection and/or hole transport or block electron overflow. When placed between the cathode and the light emitting layer, the light emitting auxiliary layer may be used to promote electron injection and/or electron transport or to block hole overflow. Further, a hole assist layer may be disposed between the hole transport layer (or hole injection layer) and the light emitting layer, and it may exhibit an effect of promoting or blocking a hole transport rate (or hole injection rate), and thus charge balance may be adjusted. In addition, an electron blocking layer may be disposed between the hole transporting layer (or hole injecting layer) and the light emitting layer, and it may block the overflow of electrons from the light emitting layer and confine excitons in the light emitting layer to prevent light leakage. 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.
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 an anion, and thus injection and transport of electrons from the mixed region to the light emitting medium become easier. In addition, the hole transport compound is oxidized to a cation, and thus injection and transport of holes from the mixed region to the light emitting medium become easier. Preferred oxidizing dopants include various lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, an organic electroluminescent device having at least two light emitting layers and emitting white light may be manufactured by using a reducing dopant layer as a charge generating layer.
According to one embodiment of the present disclosure, an organic electroluminescent material may be used as a light emitting material for a white organic light emitting device. A white organic light emitting device has been proposed to have various structures such as a side-by-side structure or a stacked structure, depending on the arrangement of R (red), G (green), or YG (yellow-green) and B (blue) light emitting parts, or a Color Conversion Material (CCM) method, or the like. Furthermore, the organic electroluminescent material according to one embodiment of the present disclosure may also be used in an organic electroluminescent device including Quantum Dots (QDs).
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 inkjet printing, nozzle printing, slit coating, spin coating, dip coating, flow coating method, or the like may be used. Co-deposition or hybrid deposition is performed when forming films of the first and second host compounds of the present disclosure.
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.
Further, a display system, for example, a display system for a smart phone, a tablet computer, a notebook computer, a PC, a TV, or an automobile, may be produced by using the organic electroluminescence device of the present disclosure; or a lighting system, such as an outdoor or indoor lighting system.
Hereinafter, a method of preparing the compound of the present disclosure and characteristics thereof, and a driving voltage and light emitting efficiency of an organic electroluminescent device (OLED) including a plurality of host materials according to the present disclosure will be explained in detail with reference to representative compounds of the present disclosure. However, the following examples only describe the characteristics of the compounds according to the present disclosure and OLEDs including the same, and the present disclosure is not limited to the following examples.
Example 1: preparation of Compound C-116
1) Synthesis of Compound B
Compound A (6 g,26.1 mmol), bis (pinacolato) diboron (13.2 g,52.2 mmol), pd 2 (dba) 3 (2.4 g,2.6 mmol), spos (2.1 g,5.2 mmol) and potassium acetate (7.7 g,78.3 mmol) were added to the reaction vessel, dissolved in 130mL of 1, 4-dioxane, and stirred under reflux for 3 hours. After the reaction was completed, the reaction product was washed with distilled water, and the organic layer was extracted with ethyl acetate and dried over magnesium sulfate. The solvent was removed by a rotary evaporator and the residue was purified by column chromatography to obtain compound B (8 g, yield: 96%).
2) Synthesis of Compound C-116
Compound B (5 g,15.6 mmol), compound C (4.6 g,12.9 mmol), pd (PPh) 3 ) 4 (750 mg,0.65 mmol) and potassium carbonate (5.3 g,38.9 mmol) were added to a reaction vessel, dissolved in 65mL toluene, 20mL ethanol and 20mL water, and added at 12Reflux is carried out for 3 hours at 0 ℃. After the reaction was completed, the resulting solid was filtered and washed with methanol. The filtrate was recrystallized from xylene and ethyl acetate to obtain compound C-116 (2.6 g, yield: 32%).
| MW | Melting point | |
| C-116 | 516.56 | 273℃ |
Example 2: preparation of Compound C-117
Compound B (6 g,18.6 mmol), compound D (6 g,16.7 mmol), pd (PPh) 3 ) 4 (1.07 g,0.92 mmol) and potassium carbonate (7.74 g,56 mmol) were added to the reaction vessel, dissolved in 84mL of toluene, 28mL of ethanol and 28mL of water, and refluxed at 120℃for 3 hours. After the reaction was completed, the resulting solid was filtered and washed with methanol. The filtrate was recrystallized from xylene and ethyl acetate to obtain compound C-117 (3.7 g, yield: 38.5%).
| MW | Melting point | |
| C-117 | 516.56 | 286℃ |
Example 3: preparation of Compound C-118
Compound B (6 g,18.6 mmol), compound E (6 g,16.7 mmol), pd (PPh) 3 ) 4 (1.07 g,0.92 mmol) and potassium carbonate (7.74 g,56 mmol) were added to the reaction vessel, dissolved in 84mL of toluene, 28mL of ethanol and 28mL of water, and refluxed at 120℃for 3 hours. After the reaction was completed, the resulting solid was filtered and washed with methanol. The filtrate was recrystallized from xylene and ethyl acetate to obtain compound C-118 (5.2 g, yield: 54%).
| MW | Melting point | |
| C-118 | 516.56 | 305℃ |
Example 4: preparation of Compound C-180
Compound B (3.7 g,11.6 mmol), compound E (5 g,11.6 mmol), pd (PPh) 3 ) 4 (640 mg,0.57 mmol) and potassium carbonate (4.8 g,34.7 mmol) were added to the reaction vessel, dissolved in 60mL toluene, 30mL ethanol and 30mL water, and refluxed at 120℃for 3 hours. After the reaction was completed, the resulting solid was filtered and washed with methanol. The filtrate was recrystallized from xylene and ethyl acetate to obtain compound C-180 (3.2 g, yield: 47%).
| MW | Melting point | |
| C-180 | 591.2 | 303℃ |
Device examples 1 to 10: producing an OLED deposited with multiple host materials according to the present disclosure
An OLED according to the present disclosure was produced. First, a transparent electrode Indium Tin Oxide (ITO) film (10Ω/sq) (Japanese Ji Aoma Co., ltd. (GEOMATECCO., LTD., japan)) on a glass substrate for OLED was sequentially coated with acetone and isopropyl alcoholUltrasonic washing was performed and then stored in isopropanol. The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. The compound HI-1 shown in Table 3 was introduced into one cell of a 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 in a doping amount of 3wt% based on the total amount of compound HI-1 and compound HT-1 to form a hole injection layer having a thickness of 10 nm. Subsequently, the compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 80 nm. Next, 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 depositing a second hole transport layer having a thickness of 30nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light emitting layer was deposited thereon as follows: each of the first host compound and the second host compound shown in table 1 below was introduced as a host into two cells of a vacuum vapor deposition apparatus, and compound D-130 was introduced as a dopant into the other cell. The two host materials were evaporated at a rate of 1:2 (first host: second host), and the dopant materials were simultaneously evaporated at different rates, and the dopants were deposited at a doping amount of 10wt% based on the total of the host and the dopants to form a light emitting layer having a thickness of 40nm on the second hole transport layer. Then, the compound ETL-1 and the compound EIL-1 were evaporated as electron transport materials at a weight ratio of 40:60 to form an electron transport layer having a thickness of 35nm on the light emitting layer. After depositing the compound EIL-1 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 using another vacuum vapor deposition apparatus, thereby producing an OLED. All materials used for producing the OLED are shown in 10 -6 Purification by vacuum sublimation was performed under the tray.
Comparative example 1: production of an OLED comprising a contrast compound as host
An OLED was produced in the same manner as in device examples 1 to 10, except that compound C-1 was used alone as the host of the light-emitting layer.
The driving voltage, the light emitting efficiency and the light emitting color of the OLEDs produced in device examples 1 to 10 and comparative example 1 at a luminance of 1,000 nit, and the time taken for the luminance to decrease from 100% to 50% at a luminance of 60,000 nit (lifetime: T50) are shown in table 1 below.
[ Table 1 ]
As can be confirmed from table 1 above, the OLEDs (device examples 1 to 10) comprising the plurality of host materials according to the present disclosure exhibited lower driving voltages, higher luminous efficiencies, and significantly improved lifetime characteristics as compared to the OLED (comparative example 1) comprising the conventional host material. Since the OLED according to comparative example 1 cannot achieve a luminance of 60,000 nits, it is impossible to measure the lifetime thereof.
Device examples 11 to 14: producing an OLED deposited with multiple host materials 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) (japanese Ji Aoma limited (GEOMATECCO., LTD., japan)) on a glass substrate for OLED was sequentially ultrasonically washed with acetone and isopropyl alcohol, and then stored in isopropyl alcohol. The ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. The compound HI-1 shown in Table 3 was introduced into one cell of a 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 in a doping amount of 3wt% based on the total amount of compound HI-1 and compound HT-1 to form a hole injection layer having a thickness of 10 nm. Subsequently, the compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 80 nm. Next, 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 depositing a second hole transport layer having a thickness of 30nm on the first hole transport layer. In the shape of After forming the hole injection layer and the hole transport layer, a light emitting layer was deposited thereon as follows: the host compound shown in table 2 below was introduced as a host into two cells of a vacuum vapor deposition apparatus, and compound D-130 was introduced as a dopant into the other cell. The dopant and the host material were simultaneously evaporated at different rates, and the dopant was deposited at a doping amount of 10wt% based on the total amount of the host and the dopant to form a light emitting layer having a thickness of 40nm on the second hole transport layer. Then, the compound ETL-1 and the compound EIL-1 were evaporated as electron transport materials at a weight ratio of 40:60 to form an electron transport layer having a thickness of 35nm on the light emitting layer. After depositing the compound EIL-1 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 using another vacuum vapor deposition apparatus, thereby producing an OLED. All materials used for producing the OLED are shown in 10 -6 Purification by vacuum sublimation was performed under the tray.
Comparative example 2: production of an OLED comprising a contrast compound as host
An OLED was produced in the same manner as in device examples 11 to 14, except that compound a was used alone as the host of the light-emitting layer.
The driving voltage, the light emitting efficiency and the light emitting color of the OLEDs produced in device examples 11 to 14 and comparative example 2 at a luminance of 1,000 nit, and the time taken for the luminance to decrease from 100% to 50% at a luminance of 20,000 nit (lifetime: T50) are shown in table 2 below.
[ Table 2 ]
As can be confirmed from table 2 above, the OLEDs (device examples 11 to 14) comprising the host compounds according to the present disclosure exhibited lower driving voltages, higher luminous efficiencies, and significantly improved lifetime characteristics compared to the OLEDs (comparative example 2) comprising the conventional host compounds.
The compounds used in the device examples and comparative examples are shown in table 3 below.
[ Table 3 ]
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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:
in the formula (1) of the present invention,
x represents O or S;
R 1 to R 5 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or formula a below; provided that R 1 To R 5 Wherein at least one of the formulae a;
in the formula (a) of the formula (a),
L 1 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group;
Y 1 To Y 3 Each independently represents N or CH; provided that Y 1 To Y 3 Wherein at least two of them represent N; and is also provided with
Ar 1 And Ar is a group 2 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;
in the formula (2) of the present invention,
A 1 and A 2 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted carbazolyl group;
X 15 to X 18 Any one of which is combined with X 19 To X 22 Any one of which are connected to each other to form a single bond; and is also provided with
X not forming said single bond 11 To X 14 、X 23 To X 26 And X 15 To X 22 Each independently represents hydrogen, deuterium, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl; or may be attached to one or more adjacent substituents to form one or more rings.
2. The plurality of host materials of claim 1, wherein Ar of formula a 1 And Ar is a group 2 Each independently represents phenyl unsubstituted or substituted by one or more dibenzofuranyl groups, one or more dibenzothiophenyl groups, one or more carbazolyl groups or one or more 9-phenylcarbazolyl groups; a biphenyl group; a terphenyl group; a tetrabiphenyl group; a naphthyl group; phenyl naphthyl; a naphthylphenyl group; a pyridyl group; pyrimidinyl; triazinyl; dibenzofuranyl, unsubstituted or substituted with one or more phenyl groups; dibenzothienyl, unsubstituted or substituted with one or more phenyl groups; or a carbazolyl group unsubstituted or substituted with at least one of one or more phenyl groups and one or more biphenyl groups, which groups may be further substituted with at least one deuterium.
3. The plurality of host materials of claim 1, wherein in formula 2, X 11 、X 18 、X 19 And X 26 Represents deuterium.
4. The plurality of host materials of claim 1, wherein the compound represented by formula 2 has a deuterium substitution rate of 40% to 100%.
5. The plurality of host materials of claim 1, wherein in formula 2, X 11 To X 26 The deuterium substitution rate of (2) is 25% to 100%.
6. The plurality of host materials of claim 1, wherein formula 2 is represented by at least one of the following formulas 2-1 to 2-8:
in formulas 2-1 to 2-8,
A 1 、A 2 and X 11 To X 26 Is as defined in claim 1.
7. The plurality of host materials of claim 1, wherein a of formula 2 1 And A 2 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted benzofluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted dibenzothiophenyl group.
8. The plurality of host materials of claim 1, wherein one or more substituents of the substituted alkyl, the substituted (arylene), the substituted (heteroarylene), the substituted dibenzofuranyl, the substituted dibenzothienyl, and the substituted carbazolyl are each independently at least one selected from the group consisting of: deuterium; halogen; cyano group; a carboxyl group; a nitro group; a hydroxyl group; phosphine oxide; (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; a (3-to 30-membered) heteroaryl group that is unsubstituted or substituted with at least one of deuterium and one or more (C6-C30) aryl groups; (C6-C30) aryl, unsubstituted or substituted with deuterium; 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- (C2-C30) alkenylamino; mono-or di- (C6-C30) arylamino; mono-or di- (3-to 30-membered) heteroarylamino; (C1-C30) alkyl (C2-C30) alkenylamino; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkyl (3-to 30-membered) heteroarylamino; (C2-C30) alkenyl (C6-C30) arylamino; (C2-C30) alkenyl (3-to 30-membered) heteroarylamino; (C6-C30) aryl (3-to 30-membered) heteroarylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; (C6-C30) arylphosphines; 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.
9. The plurality of host materials according to claim 1, wherein the compound represented by formula 1 is at least one selected from the group consisting of:
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10. the plurality of host materials according to claim 1, wherein the compound represented by formula 2 is at least one selected from the group consisting of:
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in the compound, D n Meaning that n numbers of hydrogens are replaced with deuterium.
11. An organic electroluminescent compound represented by the following formula 3:
in the case of the method of 3,
x' represents O or S;
R' 1 represents phenyl unsubstituted or substituted by deuterium;
R' 2 to R'. 5 Each independently represents hydrogen, deuterium, a substituted or unsubstituted (C6-C30) aryl group, or a' formula; provided that R 'is' 2 To R'. 5 Wherein at least one of the formulae a';
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in the formula a' of the formula (a),
L' 1 represents a single bond, or a substituted or unsubstituted (C6-C30) arylene group;
Y' 1 to Y' 3 Each independently represents N or CH; provided that Y' 1 To Y' 3 Wherein at least two of them represent N;
Ar' 1 and Ar' 2 Each independently represents a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group; provided that Ar' 1 And Ar' 2 Is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group; and is also provided with
Ar' 1 And Ar' 2 Different from each other.
12. The organic electroluminescent compound according to claim 11, wherein the compound represented by formula 3 is selected from the group consisting of:
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13. an organic electroluminescent device comprising a plurality of host materials according to claim 1.
14. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 11.
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| KR1020230061568A KR20240008238A (en) | 2022-07-11 | 2023-05-12 | A plurality of host materials, organic electroluminescent compound, and organic electroluminescent device comprising the same |
| KR10-2023-0061568 | 2023-05-12 |
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