CN117586271A - 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 PDF

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CN117586271A
CN117586271A CN202310990273.4A CN202310990273A CN117586271A CN 117586271 A CN117586271 A CN 117586271A CN 202310990273 A CN202310990273 A CN 202310990273A CN 117586271 A CN117586271 A CN 117586271A
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substituted
unsubstituted
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deuterium
membered
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郑昭永
愼孝壬
文斗铉
赵相熙
姜炫周
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Rohm and Haas Electronic Materials Korea Ltd
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Rohm and Haas Electronic Materials Korea Ltd
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Priority claimed from KR1020230090920A external-priority patent/KR20240021108A/en
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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 a specific combination of compounds according to the present disclosure as a variety of host materials or by including a compound according to the present disclosure, an organic electroluminescent device having a lower driving voltage, higher luminous efficiency, and/or longer lifetime characteristics than conventional organic electroluminescent devices can be produced.

Description

Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same
Technical Field
The present disclosure relates to various host materials, organic electroluminescent compounds, and organic electroluminescent devices including the same.
Background
A small-molecule green organic electroluminescent device (OLED) was first developed by Tang et al from Eastman Kodak, inc. 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 realization. However, in many applications such as TV and lighting devices, the lifetime of the OLED is insufficient and still a higher efficiency of the OLED is required. Typically, the higher the luminance of an OLED, the shorter the lifetime an OLED has. Accordingly, for long-term use and high resolution of the display, an OLED having long-life characteristics is required.
Meanwhile, korean patent publication No. 1612164 discloses a compound in which an amine group is condensed with a dibenzo moiety comprising carbazole, fluorene, or 5-membered heterocycle to form a ring. However, the foregoing references do not specifically disclose a variety of host materials or specific combinations of host materials comprising specific compounds as claimed in the present disclosure. Furthermore, there is a continuing need to develop luminescent materials with more improved performance (e.g., improved driving voltage, luminous efficiency, and/or lifetime characteristics) compared to previously disclosed OLEDs.
Disclosure of Invention
Technical problem
It is an object of the present disclosure to provide a variety of host materials capable of providing an organic electroluminescent device 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 significantly improved driving voltage, luminous 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 technical problems, the present inventors have found that the above object can be achieved by a variety of host materials comprising at least one first host compound represented by the following formula 1 and at least one second host compound represented by the following formula 2, or compounds represented by the following formula 1' or any one of the following formulas 2' -1 to 2' -4.
In the formula (1) of the present invention,
x represents-O-, -S-, -N (R) -, C (R') (R ") -or-Se-;
r, R 'and R' each independently represent 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, -L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 ) The method comprises the steps of carrying out a first treatment on the surface of the Or R ' and R ' may be linked to each other to form one or more rings, and R ' may be the same or different;
R 1 to R 13 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, one or more (C3-C30) aliphatic rings, and a substituted or unsubstituted fused ring group of one or more (C6-C30) aromatic rings, -L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to one or more adjacent substituents to form one or more rings;
provided that R, R ', R' and R 1 To R 13 At least one of them represents-L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 )；
L 1 And L 2 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;
L 3 represents a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group; and is also provided with
Ar 1 To Ar 5 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted condensed ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, 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,
X 1 to X 3 Each independently represents-N=or-C (R 20 ) =, provided that X 1 To X 3 Wherein at least one of them represents N;
R 20 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, or a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic and one or more (C6-C30) aromatic rings;
L 4 To L 6 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-memberedMeta) heteroarylene;
Ar 6 to Ar 8 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, one or more (C3-C30) aliphatic rings, and one or more (C6-C30) aromatic ring substituted or unsubstituted fused ring groups or-N- (R) 21 )(R 22 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to one or more adjacent substituents to form one or more rings; provided that Ar is 6 To Ar 8 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
R 21 And R is 22 Each independently represents 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 the formula 1' of the present invention,
x represents-N (R) -, -C (R') (R ") -or-Se-;
r, R 'and R' each independently represent 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, -L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 ) The method comprises the steps of carrying out a first treatment on the surface of the Or R ' and R ' may be linked to each other to form one or more rings, and R ' may be the same or different;
R 1 to R 13 Each independently of the otherRepresents 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, one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic ring substituted or unsubstituted fused ring groups, -L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to one or more adjacent substituents to form one or more rings;
Provided that R, R ', R' and R 1 To R 13 At least one of them represents-L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 )；
L 1 And L 2 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;
L 3 represents a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group; and is also provided with
Ar 1 To Ar 5 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted condensed ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
In the formulae 2'-1 to 2' -4,
t represents O or S;
X 1 ' to X 4 ' 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;
L 4 ' to L 6 ' each independently represents a single bond, unsubstituted or deuterium-substituted phenylene, or unsubstituted or deuterium-substituted naphthylene; and is also provided with
Ar 7 ' and Ar 8 ' each independently represents an unsubstituted or deuterium-substituted phenyl group, an unsubstituted or deuterium-substituted biphenyl group, an unsubstituted or deuterium-substituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzonaphthofuryl group, or a substituted or unsubstituted benzonaphthothienyl group;
In the formula 2' -1 of the present invention,
X 6 ' to X 8 ' each independently represents hydrogen, deuterium or-L 7 -Ar 9 Provided that X 6 ' to X 8 At least one of' represents-L 7 -Ar 9 ；
If X 6 ' is-L 7 -Ar 9 L is then 7 Represents a single bond, unsubstituted or deuterium-substituted phenylene group, or unsubstituted or deuterium-substituted naphthylene group, and Ar 9 Represents unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, or unsubstituted or deuterium-substituted naphthyl; provided that if L 7 Is a single bond, ar 9 Represents unsubstituted or deuterium-substituted naphthyl;
if X 7 ' is-L 7 -Ar 9 L is then 7 Represents a single bond, unsubstituted or deuterium-substituted phenylene group, or unsubstituted or deuterium-substituted naphthylene group, ar 9 Represents unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, or unsubstituted or deuterium-substituted naphthyl;
if X 8 ' is-L 7 -Ar 9 L is then 7 Represents a single bond, unsubstituted or deuterium-substituted phenylene group, or unsubstituted or deuterium-substituted naphthylene group, ar 9 Represents phenyl which is unsubstituted or substituted by deuterium, or naphthyl which is unsubstituted or substituted by deuterium; and is also provided with
Provided that if X 8 ' is-L 7 -Ar 9 And phenyl, then Ar 7 ' and Ar 8 At least one of' represents a dibenzofuranyl or dibenzothienyl group;
In the formula 2' -2 of the present invention,
X 8 ' represents-L 7 -Ar 9 And X is 5 ' and X 7 ' each independently represents hydrogen or deuterium;
L 7 represents a single bond, unsubstituted or deuterium-substituted phenylene group, or unsubstituted or deuterium-substituted naphthylene group, and Ar 9 Represents hydrogen, unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, or unsubstituted or deuterium-or one or more phenyl-substituted naphthyl; and is also provided with
Provided that if L 7 Is a single bond, ar 9 Represents unsubstituted or deuterium-substituted naphthyl;
in the formula 2' -3 of the present invention,
X 5 '、X 6 ' and X 8 ' each independently represents hydrogen, deuterium or-L 7 -Ar 9 Provided that X 5 '、X 6 ' and X 8 At least one of' represents-L 7 -Ar 9 ；
L 7 Represents a single bond, unsubstituted or deuterium-substituted phenylene group, or unsubstituted or deuterium-substituted naphthylene group, ar 9 Represents phenyl which is unsubstituted or substituted by deuterium or one or more naphthyl groups, biphenyl which is unsubstituted or substituted by deuterium, or naphthyl which is unsubstituted or substituted by deuterium; and is also provided with
Provided that if X 5 ' is-L 7 -Ar 9 And naphthyl, ar 7 ' and Ar 8 At least one of' represents a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group;
in the formula 2' -4, the amino acid sequence,
X 5 ' to X 7 ' each independently represents hydrogen, deuterium, or-L 7 -Ar 9 Provided that X 5 ' to X 7 At least one of' represents-L 7 -Ar 9 The method comprises the steps of carrying out a first treatment on the surface of the And is also provided with
L 7 Represents a single bond, unsubstituted or deuterium-substituted phenylene group, or unsubstituted or deuterium-substituted naphthylene group, and Ar 9 Represents unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, or unsubstituted or deuterium-substituted naphthyl.
The beneficial effects of the invention are that
By including a specific combination of compounds according to the present disclosure as a variety of host materials or by including a compound according to the present disclosure, an organic electroluminescent device having significantly improved driving voltage, luminous efficiency, and/or lifetime characteristics compared to conventional organic electroluminescent devices can be produced.
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 in any way.
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 "multiple host materials" in the present disclosure 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 (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 host materials of the present disclosure is a combination of at least two host materials, and may optionally further include 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, or may be included in different light emitting layers, respectively. For example, at least two 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 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. The term "(C3-C30) (alkylene) 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. The term "(3-to 7-membered) heterocycloalkyl" means cycloalkyl having 3 to 7 ring backbone atoms and including at least one heteroatom selected from the group consisting of B, N, O, S, si and P, and preferably consisting of O, S and N. The heterocycloalkyl group may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene, tetrahydropyran, and the like. The term "(C6-C30) (arylene) refers to a monocyclic or fused ring group derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms. The aryl groups described above may be partially saturated and may contain spiro structures. The aryl group may include phenyl, biphenyl, terphenyl, tetrabiphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorene Phenyl, diphenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthracyl, indenyl, triphenylenyl, pyrenyl, naphthacene, perylenyl,Group, naphto-naphthyl group, fluoranthenyl group, spirobifluorenyl group, spiro [ fluorene-benzofluorene ]]A group, azulenyl (azulenyl), tetramethyldihydrophenanthryl, cumenyl, and the like. Specifically, the aryl group may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthraceyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, tetracenyl, 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-benzophenanthryl, 2-benzophenanthryl, 3-benzophenanthryl, 4-benzophenanthryl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl and 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-tetrabiphenyl3-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, p-tolyl, p-xylyl, p-tolyl, p-xylyl, p-phenylpropyl, p-tolyl, p-xylyl, and p-tolyl 4' -tert-butyl-p-terphenyl-4-yl, 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, 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, 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) (arylene) heteroaryl" means an (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, P, se and Ge. 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 and pyridazinyl, and fused ring heteroaryl groups, 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, benzopyranoquinazolinyl, thiobenzopyranoquinazolinyl, dimethylphenopyrimidinyl, indolocarzolyl, indenocarzolyl, and the like. More specifically, the process is carried out, the heteroaryl group 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-indolinyl, 2-indolinyl, 3-indolinyl, 5-indolinyl, 6-indolinyl, 7-indolinyl, 8-indolinyl, 2-imidazopyridyl, 3-imidazopyridyl, 5-imidazopyridyl, 6-imidazopyridyl 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, 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-azanyl, 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, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothienyl, 2-dibenzothienyl, 3-dibenzothienyl, 4-dibenzothienyl, 2-dibenzo- [1,2-b ] -2- [ 2-b ] -2, 2- [ 2-b ] -2-naphtho-b ] -1, 2-naphtho- [ b ] -2-naphthyridinyl 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, 5-naphtho- [2,3-b ] -benzofuranyl, 1-naphtho- [2, 2-b ] -benzofuranyl, 5-naphtho-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-benzofuro [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-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 addition, "halogen" includes F, cl, br and I.
In addition, "o-," m-, "and" p-) "are prefixes, and represent the relative positions of substituents, respectively. Ortho means that two substituents are adjacent to each other and is referred to as ortho, for example, if 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, if 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 meta, for example, if two substituents in the benzene derivative occupy positions 1 and 4.
In this context, 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. Herein, each of the one or more substituents of the substituted fused ring groups of the substituted alkyl, substituted alkenyl, substituted aryl, substituted arylene, substituted heteroaryl, substituted heteroarylene, substituted cycloalkyl, substituted cycloalkylene, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and one or more aliphatic and one or more aromatic rings is 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 unsubstituted or substituted by one or more (C6-C30) aryl groups; (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 one or more (C6-C30) aryl groups; (C6-C30) aryl unsubstituted or substituted with at least one of one or more (C1-C30) alkyl groups and one or more (3-to 30-membered) heteroaryl groups; tri (C1-C30) alkylsilyl; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; a fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings; an amino group; mono-or di- (C1-C30) alkylamino; mono-or di- (C2-C30) alkenylamino; substituted or unsubstituted 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; 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, wherein the substituents may be further substituted with deuterium. 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; cyano group; (C1-C20) alkyl; (C6-C25) aryl; (5-to 25-membered) heteroaryl; substituted or unsubstituted di (C6-C25) arylamino; and (C6-C25) aryl (C1-C20) alkyl. 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; cyano group; (C1-C10) alkyl; (C6-C20) aryl; (5-to 20-membered) heteroaryl; di (C6-C18) arylamino groups unsubstituted or substituted with deuterium; and (C6-C18) aryl (C1-C10) alkyl. For example, the one or more substituents may be at least one selected from the group consisting of: deuterium, cyano, methyl, phenyl, naphthyl, biphenyl, phenanthryl, fluorenyl, phenylfluorenyl, cumenyl, isopropyl substituted with one or more phenyl groups, triphenylsilyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl, phenylbiphenylamino, and diphenylamino groups, wherein the substituents may be further substituted with deuterium.
In the present disclosure, 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 25-membered) alicyclic 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 (5-to 25-membered) heteroaryl groups. Furthermore, the ring formed may contain at least one heteroatom selected from B, N, O, S, si, P, se and Ge, preferably at least one heteroatom selected from N, O, S and Se. For example, the ring may be a benzene ring, a cyclopentane ring, an indane ring, a fluorene ring unsubstituted or substituted with one or more phenyl groups, a phenanthrene ring, an indole ring, a xanthene ring, a benzofuropyridine ring, a benzothiophene pyridine ring, a dibenzothiophene ring, a dibenzofuran ring, a naphthalene ring, a benzofluorene ring, a benzothiophene ring, a benzofuran ring, an indene ring, a carbazole ring, or the like.
In the present disclosure, each of the heteroaryl (ene) and heterocycloalkyl (heterocycle) independently may include at least one heteroatom selected from B, N, O, S, si, P, se and Ge. Furthermore, the heteroatom may be bonded to at least one selected from the group consisting of: 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 mono-or di- (C1-C30) alkylamino, substituted or unsubstituted mono-or di- (C2-C30) alkenylamino, substituted or unsubstituted mono-or di- (C6-C30) arylamino, substituted or unsubstituted mono-to 30-membered hetero (C1-to 30) alkylamino, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or unsubstituted mono-or di- (C2-C30) alkylamino, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or di (C1-to 30-membered alkylamino, substituted or unsubstituted (C30-to 30-C amino Substituted or unsubstituted (C2-C30) alkenyl (3-to 30-membered) heteroarylamino, and substituted or unsubstituted (C6-C30) aryl (3-to 30-membered) heteroarylamino.
The plurality of host materials of the present disclosure comprises a first host compound and a second host compound, wherein the first host material comprises at least one first host compound represented by formula 1, and the second host material comprises at least one second host compound represented by formula 2.
According to one embodiment, the first host compound (which is a host material) may be represented by formula 1.
In the formula (1) of the present invention, X represents-O-, -S-, -N (R) -, C (R') (R ") -or-Se-. According to one embodiment of the present disclosure, X represents-N (R) -, C (R') (R ") -or-Se-.
R, R 'and R' each independently represent 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, -L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 ) The method comprises the steps of carrying out a first treatment on the surface of the Or R ' and R ' may be linked to each other to form one or more rings, and R ' may be the same or different. According to one embodiment of the present disclosure, R, R ', and R' each independently represent a substituted or unsubstituted (C1-C20) alkyl, -L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 ). According to another embodiment of the present disclosure, R, R 'and R' each independently represent unsubstituted (C1-C10) alkyl, -L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 ). For example, R may be-L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 ) And R' may be methyl.
In formula 1, R 1 To R 13 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, one or more (C3-C30) aliphatic rings, and a substituted or unsubstituted fused ring group of one or more (C6-C30) aromatic rings, -L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to one or more adjacent substituents to form one or more rings. For example, R 1 To R 13 Each independently can be hydrogen, deuterium, -L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 )。
In formula 1, R, R ', R' and R ', R' are 1 To R 13 At least one of them represents-L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 ). According to one embodiment of the present disclosure, R, R', R ", and R 1 To R 13 Either or both of them independently represent-L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 )。
In formula 1, L 1 And L 2 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. According to one embodiment of the present disclosure, L 1 And L 2 Each independently represents a single bond, a substituted or unsubstituted (C6-C25) arylene group, or a substitutionOr unsubstituted (5-to 25-membered) heteroarylene. According to another embodiment of the present disclosure, L 1 And L 2 Each independently represents a single bond, a substituted or unsubstituted (C6-C18) arylene group, or an unsubstituted (5-to 20-membered) heteroarylene group. The one or more substituents of the substituted arylene and substituted heteroarylene may each independently be at least one selected from the group consisting of deuterium, (C6-C30) aryl and di (C6-C30) arylamino. For example, L 1 And L 2 Each independently may be a single bond, a substituted or unsubstituted phenylene group, an unsubstituted naphthylene group, an unsubstituted dibenzofuranylene group, or the like, wherein one or more substituents of the substituted phenylene group may be at least one selected from the group consisting of: deuterium, phenyl, naphthyl, diphenylamino and phenylbiphenylamino, unsubstituted or substituted by deuterium.
In formula 1, L 3 Represents 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 3 Represents a substituted or unsubstituted (C6-C25) arylene group, or a substituted or unsubstituted (5-to 25-membered) heteroarylene group. According to another embodiment of the present disclosure, L 3 Represents a (C6-C18) arylene group which is unsubstituted or substituted by at least one of deuterium and one or more (C6-C30) aryl groups. For example, L 3 May be unsubstituted or phenylene substituted with at least one of deuterium and one or more phenyl groups, and the like.
In formula 1, ar 1 To Ar 5 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted condensed ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, 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 To Ar 5 Each independently represents a substituted or unsubstituted (C6-C25) aryl group, or a substituted or unsubstituted (5-to 25-membered) heteroaryl group. According to another embodiment of the present disclosure, ar 1 To Ar 5 Each independently represents a substituted or unsubstituted (C6-C18) aryl group,Or a (5-to 20-membered) heteroaryl group which is unsubstituted or substituted by one or more (C6-C18) aryl groups. The one or more substituents of the substituted aryl group may be at least one selected from the group consisting of: deuterium, (C1-C30) alkyl, (C6-C30) aryl, (3-to 30-membered) heteroaryl and (C6-C30) aryl (C1-C30) alkyl. Specifically, ar 1 To Ar 5 Each independently may be a substituted or unsubstituted phenyl, naphthyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothienyl, fluorenyl, spirobifluorenyl, tetrabiphenyl, cumenyl, carbazolyl, phenanthryl, benzophenanthryl,a group, triphenylene, benzocarbazolyl, benzonaphthalenyl, benzonaphthathiophenyl, benzofluorenyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, naphthooxazolyl, benzonaphthazolyl, naphthazolyl, benzonaphthazolyl, or naphthaimidazolyl. For example, ar 1 To Ar 5 Each independently may be a substituted or unsubstituted phenyl group, naphthyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, naphthylphenyl group, phenylnaphthyl group, phenanthryl group, dimethylfluorenyl group, diphenylfluorenyl group, spirobifluorenyl group, o-terphenyl group, m-terphenyl group, o-tetraphenyl group, dibenzofuranyl group, dibenzothienyl group, phenylcarbazolyl group, dibenzoselenophenyl group, benzonaphthofuryl group, or the like, wherein the one or more substituents of the substituted phenyl group may be at least one selected from the group consisting of deuterium, dibenzofuranyl group, carbazolyl group, isopropyl group substituted with one or more phenyl groups, and cumene group, wherein the substituents may be further substituted with deuterium.
According to one embodiment of the present disclosure, formula 1 is represented by at least one of the following formulas 1-1 to 1-28:
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x, R in the formulae 1-1 to 1-28 1 To R 13 、L 1 To L 3 And Ar 1 To Ar 5 The definition and preferred embodiment of (2) are the same as in formula 1.
According to another embodiment, the second host compound (which is a host material) may be represented by formula 2.
In formula 2, X 1 To X 3 Each independently represents-N=or-C (R 20 ) =, provided that X 1 To X 3 Is N. According to one embodiment of the present disclosure, X 1 To X 3 Is N. According to another embodiment of the present disclosure, X 1 To X 3 Are all N.
R 20 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, or a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic and one or more (C6-C30) aromatic rings. For example, R 20 May be hydrogen or deuterium.
In formula 2, L 4 To L 6 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. According to one embodiment of the present disclosure, L 4 To L 6 Each independently represents a single bond, a substituted or unsubstituted (C6-C25) arylene group, or a substituted or unsubstituted (5-to 25-membered) heteroarylene group. According to another embodiment of the present disclosure, L 4 To L 6 Each independently represents a single bond, a substituted or unsubstituted (C6-C18) arylene group, or a substituted or unsubstituted (5-to 20-membered) heteroarylene group. For example, L 4 To L 6 Each independently may be a single bond, a substituted or unsubstituted phenylene group, a naphthylene group, a biphenylene group, a naphthylene phenyl group, a phenylene naphthyl group, a fluorenylene group, a phenanthrylene group, a pyridylene group, a carbazole group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzonaphthothiophenylene group, a naphthooxazolylene group, a naphthothiazolylene group, or a benzonaphthofuranyl group.
In formula 2, ar 6 To Ar 8 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, one or more (C3-C30) aliphatic rings, and one or more (C6-C30) aromatic ring substituted or unsubstituted fused ring groups or-N- (R) 21 )(R 22 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to one or more adjacent substituents to form one or more rings; provided that Ar is 6 To Ar 8 Represents 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 6 To Ar 8 Each independently represents a substituted or unsubstitutedSubstituted (C6-C25) aryl, substituted or unsubstituted (5-to 25-membered) heteroaryl, or substituted or unsubstituted tri (C6-C25) arylsilyl. According to another embodiment of the present disclosure, ar 6 To Ar 8 Each independently represents 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.
For example, ar 6 To Ar 8 At least one of which may be a substituted or unsubstituted (5-to 30-membered) heteroaryl group, and preferably Ar 6 To Ar 8 May be substituted or unsubstituted (5-to 30-membered) heteroaryl.
For example, ar 6 To Ar 8 May be a substituted or unsubstituted (C6-C30) aryl group.
Specifically, ar 6 To Ar 8 Each independently may be a substituted or unsubstituted phenyl, naphthyl, p-biphenyl, m-biphenyl, o-terphenyl, m-terphenyl, p-terphenyl triphenylsilyl, triphenylgermanium, dibenzofuran, dibenzothiophene, benzoselenophene, fluorenyl, spirobifluorenyl, carbazolyl, phenanthryl, benzophenanthryl, and benzophenanthryl, A group, triphenylene, benzocarbazolyl, benzonaphthalenyl, benzonaphthathiophenyl, benzofluorenyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, naphthooxazolyl, benzonaphthazolyl, naphthazolyl, benzonaphthazolyl, or naphthaimidazolyl. For example, ar 6 To Ar 8 Each independently may be a substituted or unsubstituted phenyl, naphthyl, p-biphenyl, m-biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, triphenylsilyl, triphenylgermanium, dibenzofuranyl, dibenzothienyl, dibenzoselenophenyl, fluorenyl, benzofluorenyl, spirobifluorenyl, phenanthryl, or a combination thereof>A group, triphenylene group, carbazole group, benzonaphthofuran group, benzonaphthothiophene group, benzonaphthooxazolyl group, benzonaphthothiazolyl group, or naphthoselenazolyl group. Herein, one or more substituents of the above substituents 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 of the present disclosure, ar 6 To Ar 8 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, C (R) 17 )(R 18 )、N(R 19 ) Or Se;
Y 1 and Y 2 Each independently represents-n=, -N (R 21 ) -, -O-, -S-; or-Se-; provided that Y 1 And Y 2 One of them represents-n=, Y 1 And Y 2 The other of (B) represents-N (R) 21 ) -, -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) arylsilylSubstituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted fused ring groups of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, or-N- (R) 22 )(R 23 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to one or more adjacent substituents to form one or more rings;
R 22 and R is 23 Each independently represents 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 19 And R is 21 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 one or more 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 represent integers from 1 to 5, b, e ', f, i and o ' represent integers from 1 to 3, c, e, h, f ', l, i ' and o represent integers from 1 to 4, d ' represents integers from 1 to 6, g, j, k, m and n ' represent integers from 1 or 2, and g ', j ', m ' and n represent integers 1;
if a to m, o, d ' to f ', i ', n ' and o ' represent integers of 2 or more, each R 1 To each R 15 May be the same or different; and is also provided with
* Is the same as L in formula 2 4 To L 6 Is connected with the connecting position of the connecting rod.
For example, 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.
For example, the number of the cells to be processed,Y 1 and Y 2 One of them may be-n=, and Y 1 And Y 2 The other of them may be-O-, -S-, or-Se-.
For example, R 1 To R 15 Each independently represents 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 may be 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 may be 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 represents 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.
For example, 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. In this case, one or more substituents of these substituents may be selected from deuterium, cyano, methyl, phenyl, triphenylsilyl and triphenylgermaniumAt least one of the groups.
According to another embodiment of the present disclosure, the present disclosure provides an organic electroluminescent compound represented by formula 1', and an organic electroluminescent device including the same.
In the formula 1 'of the present invention, X represents-N (R) -, -C (R') (R ") -or-Se-. In formula 1', R, R', R ', and R' 1 To R 13 The definition and preferred embodiment of (2) are the same as in formula 1.
According to another embodiment of the present disclosure, the present disclosure provides an organic electroluminescent compound represented by any one of formulae 2'-1 to 2' -4, and an organic electroluminescent device including the same. The compound represented by formula 1 or 1' may be at least one selected from the group consisting of 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 group consisting of the following compounds, but is not limited thereto.
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The compound represented by any one of formulas 2'-1 to 2' -4 may be at least one selected from the group consisting of the following compounds, but is not limited thereto.
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The compound represented by formula 1 or 1' according to the present disclosure may be produced by a synthetic method known to those skilled in the art, for example, may be produced by referring to the following reaction schemes 1 to 6, but is not limited thereto.
Reaction scheme 1
Reaction scheme 2
Reaction scheme 3
Reaction scheme 4
Reaction scheme 5
Reaction scheme 6
In schemes 1 to 6, R', R ", L 1 To L 3 And Ar 1 To Ar 5 Is as defined in formula 1.
Although illustrative synthetic examples of the compounds represented by formula 1 or 1 'of the present disclosure 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 palps (Miyaura) boronation reaction, a suzuki cross-coupling reaction, an intramolecular acid-induced cyclization reaction, a Pd (II) catalyzed oxidative cyclization reaction, a Grignard reaction, a Heck reaction, a dehydrocyclization reaction, a SN1 substitution reaction, a SN2 substitution reaction, a phosphine-mediated reductive cyclization reaction, and the like, and that the above reactions proceed even if the substituents defined in formula 1 or 1' above but not specified in the specific synthetic examples are bonded.
The host compound represented by formula 2 according to the present disclosure may be produced by a synthetic method known to those skilled in the art, for example, by referring to the method disclosed in korean patent application laid-open No. 10-2020-0092879, etc., but is not limited thereto.
The host compounds represented by formulas 2'-1 to 2' -4 according to the present disclosure may be produced, for example, by referring to the methods disclosed in korean patent application laid-open No. 10-2014-0099082, international publication No. 2015/169412A1, korean patent application laid-open No. 10-2018-012962, etc., but are not limited thereto.
Hereinafter, an organic electroluminescent device to which various host materials and/or organic electroluminescent compounds are applied will be described.
According to one embodiment, an organic electroluminescent device includes 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 may comprise a plurality of host materials comprising at least one first host compound represented by formula 1 and at least one second host compound represented by formula 2. In this case, the weight ratio of the first host compound and the second host compound included 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 still more preferably about 50:50.
The various host materials of the present disclosure may be contained in the same organic layer (e.g., in the same light-emitting layer), or may be contained in different light-emitting layers.
According to another embodiment of the present disclosure, the organic electroluminescent compound represented by any one of formula 1' or formula 2' -1 to 2' -4 of the present disclosure may be included as a host material, 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 of the light emitting layer.
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 auxiliary layer, a light emitting auxiliary 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 materials of 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 assist layer, the light emitting assist layer, or the electron blocking layer may contain an amine-based compound (e.g., an arylamine-based compound, a styrylarylamine-based compound, or the like) as a hole injection material, a hole transport material, a hole assist material, a light emitting assist material, and an electron blocking material. In addition, the electron transport layer, the electron injection layer, the electron buffer layer, and the hole blocking layer may contain azine-based compounds as an electron transport material, an electron injection material, an electron buffer material, and 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 the metal.
A variety of host materials according to one embodiment may be used as a light emitting material for a white organic light emitting device. It has been proposed that a white organic light emitting device has 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. The various host materials according to one embodiment may also be used in organic electroluminescent devices comprising Quantum Dots (QDs).
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 depending on materials forming the first electrode and the second electrode.
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. An electron blocking layer may be disposed between the hole transport layer (or hole injection layer) and the light emitting layer, and excitons may be confined within the light emitting layer by blocking electrons from overflowing the light emitting layer to prevent light emission leakage. The hole transport layer or the electron blocking layer may also be a multilayer, wherein each of the multilayer may use a plurality of compounds.
An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof 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. The hole blocking layer is a layer that is located between the electron transport layer (or electron injection layer) and the light emitting layer and prevents holes from reaching the cathode, thereby improving the recombination probability of electrons and holes in the light emitting layer. A hole blocking layer or an electron transporting layer may use a plurality of layers, and 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, preferably, at least one layer (hereinafter, "surface layer") selected from the group consisting of a chalcogenide layer, a metal halide layer, and a metal oxide layer may be placed on one or more inner surfaces of one or both electrodes. In particular, a silicon or aluminum chalcogenide (including oxide) layer is preferably placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer is preferably placed on the cathode surface of the electroluminescent medium layer. Such a surface layer provides operational stability for the organic electroluminescent device. 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 metal halide 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 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. 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. The reducing dopant layer may be used as a charge generation layer to produce 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.
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 of the present disclosure is not particularly limited, but may be preferably selected from the group consisting of complex compounds of metallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably selected from the group consisting of complex compounds of orthometallized iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably orthometallized iridium complex compound.
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 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 substituted or unsubstituted rings, such as substituted or unsubstituted quinolines, benzofuropyridines, benzothienopyridines, indenopyridines, benzofuroquinolines, benzothienoquinolines, or indenoquinolines;
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 represents hydrogen, deuterium, halogen, unsubstituted or (C1-C30) alkyl substituted with 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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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. When the organic electroluminescent compounds or the first and second host compounds of the present disclosure are used to form a film, a co-evaporation process or a mixed evaporation process is performed.
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 according to the present disclosure and characteristics thereof, and light emitting characteristics of an organic electroluminescent device (OLED) including the organic electroluminescent compound according to the present disclosure and various host materials will be explained in detail with reference to representative compounds of the present disclosure. However, the following examples only describe the characteristics of an OLED including an organic electroluminescent compound or a plurality of host materials according to the present disclosure, and the present disclosure is not limited to the following examples.
Example 1: preparation of Compound C-1
1) Synthesis of Compound A-2
Compound A-1 (4 g,12 mmol), 4-bromo-2-iodobenzene (9.9 g,34.8 mmol), cuI (1.15 g,6 mmol), ethylenediamine (EDA) (1.4 g,23 mmol), K 3 PO 4 (7.6g，35.8mmol) and 60mL of toluene were added to the flask and stirred at 130 ℃ for 12 hours. After the reaction was completed, the reaction was cooled to room temperature, and the organic layer was extracted with ethyl acetate. After the remaining moisture was removed using magnesium sulfate, the residue was dried and separated by column chromatography to obtain compound a-2 (5 g, yield: 85%).
2) Synthesis of Compound C-1
Compound A-2 (3 g,6.2 mmol), compound A-3 (2.5 g,7.4 mmol), pd 2 (dba) 3 (283 mg,0.31 mmol), S-Phos (203 mg,0.496 mmol), naOtBu (1.2 g,124 mmol) and 126mL of o-xylene were added to the flask and stirred at 160℃for 12 hours. After the reaction was completed, the reaction was cooled to room temperature, and the organic layer was extracted with ethyl acetate. After the remaining moisture was removed using magnesium sulfate, the residue was dried and separated by column chromatography to obtain compound C-1 (2 g, yield: 44%).
Compounds of formula (I) MW Melting point
C-1 740.91 136.9℃
Example 2: preparation of Compound C-2
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Compound a-2 (2).0g,4.121 mol), diphenylamine (0.83 g,4.944 mmol), naOtBu (0.79 g,8.242 mmol), S-Phos (135 mg,0.329 mmol) and Pd 2 (dba) 3 (188 mg,0.206 mmol) was added to the flask, dissolved in 20mL of xylene, and stirred at 130℃under reflux for 12 hours. After the completion of the reaction, the organic layer was extracted with ethyl acetate. After the remaining moisture was removed using magnesium sulfate, the residue was dried and separated by column chromatography to obtain compound C-2 (1.4 g, yield: 66%).
Compounds of formula (I) MW Melting point
C-2 573.70 246.6℃
Example 3: preparation of Compound E-27
Compound A-4 (8.3 g,14.45 mmol), compound 2 (4.6 g,36.14 mmol), pd (OAc) 2 (0.32 g,1.445 mmol), S-Phos (1.2 g,2.891 mmol) and Cs 2 CO 3 (14.1 g,43.37 mmol) was added to the flask and dissolved in 80mL of o-xylene, 20mL of 1, 4-dioxane and 20mL of H 2 O and stirred at reflux for 3 hours. After the reaction was completed, the reaction was cooled to room temperature, and MeOH was added thereto. The solid was filtered, dissolved in chlorobenzene, and filtered through silica toCompound E-27 (2.5 g, yield: 28%) was obtained.
Compounds of formula (I) MW Melting point
E-27 615.6 211.4℃
Example 4: preparation of Compound E-43
Compound A-5 (15.7 g,37.35 mmol), compound 3 (11 g,29.88 mmol), pd (pph) 3 ) 4 (2.1 g,1.867 mmol) and K 2 CO 3 (15.4 g,112.0 mmol) was added to the flask and dissolved in 55mL EtOH, 55mL H 2 O and 220mL of toluene, and stirred at reflux for 2 hours. After the reaction was completed, the reaction was cooled to room temperature, and MeOH was added thereto. The solid was filtered, dissolved in chlorobenzene, and filtered through silica to obtain compound E-43 (4 g, yield: 17%).
Compounds of formula (I) MW Melting point
E-43 625.7 248.5℃
Device examples 1 and 2: production of a first host compound and a second host compound by co-deposition according to the present disclosure OLED
An OLED according to the present disclosure was produced. A transparent electrode Indium Tin Oxide (ITO) thin film (10Ω/sq) (Ji Aoma limited, japan) on a glass substrate for OLED was subjected to ultrasonic washing with acetone and isopropyl alcohol in this order, and then stored in isopropyl alcohol. The ITO substrate is then mounted on a substrate support of a vacuum vapor deposition apparatus. 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 of the vacuum vapor deposition apparatus. The two materials were evaporated at different rates, and the compound HI-1 was deposited at a doping amount of 3wt% based on the total amount of the compound HI-1 and the compound HT-1 to form a hole injection layer having a thickness of 10nm on the ITO substrate. Next, the compound HT-1 was deposited on the hole injection layer to form 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: 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-39 was introduced as a dopant into the other cell. The two host materials are evaporated at a rate of 1:1 and the dopant materials are evaporated simultaneously at different rates and the dopants are on a basis A doping amount of 3wt% of the total amount of host and dopant was deposited to form a light emitting layer having a thickness of 40nm on the second hole transport layer. The compound ET-1 and the compound EI-1 were evaporated at 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. Thereby, an OLED is produced. All materials used for producing the OLED are shown in 10 -6 Purification by vacuum sublimation was performed under the tray.
Comparative example 1: producing an OLED comprising a unitary body
An OLED was produced in the same manner as in device example 1, except that only the second host compound shown in table 1 below was used 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 nits, and the time taken for the luminance to decrease from 100% to 95% at a luminance of 10,000 nits (lifetime; T95) of the OLEDs produced in device examples 1 and 2 and comparative example 1 are provided in table 1 below.
TABLE 1
As shown in table 1 above, it can be confirmed that an OLED using a variety of host materials including the compound represented by formula 1 of the present disclosure and the compound represented by formula 2 of the present disclosure exhibits low driving voltage, high light emitting efficiency, and long life characteristics as compared to an OLED using the compound represented by formula 2 as a single host material.
Device examples 3 and 4: production of OLEDs by deposition of host compounds according to the present disclosure
An OLED according to the present disclosure was produced. A transparent electrode Indium Tin Oxide (ITO) thin film (10Ω/sq) (Ji Aoma limited, japan) on a glass substrate for OLED was subjected to ultrasonic washing with acetone and isopropyl alcohol in this order, andand then stored in isopropanol. The ITO substrate is then mounted on a substrate support of a vacuum vapor deposition apparatus. 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 of the vacuum vapor deposition apparatus. The two materials were evaporated at different rates, and the compound HI-1 was deposited at a doping amount of 3wt% based on the total amount of the compound HI-1 and the compound HT-1 to form a hole injection layer having a thickness of 10nm on the ITO substrate. Next, the compound HT-1 was deposited on the hole injection layer to form 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 host compounds shown in table 2 below were introduced as hosts into one cell of a vacuum vapor deposition apparatus, and compound D-39 was introduced as a dopant into the other cell. The dopant material was evaporated at different rates and the dopant was 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. The compound ET-1 and the compound EI-1 were evaporated at 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. Thereby, an OLED is produced. 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 example 3, except that the host compound shown in table 2 below was used 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 nits, and the time taken for the luminance to decrease from 100% to 95% at a luminance of 10,000 nits (lifetime; T95) of the OLEDs produced in device examples 3 and 4 and comparative example 2 are provided in table 2 below.
TABLE 2
As shown in table 2 above, it can be confirmed that an OLED using the compound represented by any one of formulas 2'-1 to 2' -4 of the present disclosure as a host material exhibits low driving voltage, high light emitting efficiency, and long life characteristics as compared to an OLED including the comparative compound as a host material.
The compounds used in the device examples and comparative examples are shown in table 3 below.
TABLE 3
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Claims (13)

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-, -S-, -N (R) -, C (R') (R ") -or-Se-;
r, R 'and R' each independently represent 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, -L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 ) The method comprises the steps of carrying out a first treatment on the surface of the Or R 'and R' may be linked to each other to form one or more rings,and R' may be the same or different;
R 1 to R 13 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, one or more (C3-C30) aliphatic rings, and a substituted or unsubstituted fused ring group of one or more (C6-C30) aromatic rings, -L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to one or more adjacent substituents to form one or more rings;
Provided that R, R ', R' and R 1 To R 13 At least one of them represents-L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 )；
L 1 And L 2 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;
L 3 represents a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group; and is also provided with
Ar 1 To Ar 5 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted condensed ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, 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,
X 1 to X 3 Each independently represents-N=or-C (R 20 ) =, provided that X 1 To X 3 Wherein at least one of them represents N;
R 20 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, or a substituted or unsubstituted fused ring group of one or more (C3-C30) aliphatic and one or more (C6-C30) aromatic rings;
L 4 To L 6 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 6 to Ar 8 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, one or more (C3-C30) aliphatic rings, and one or more (C6-C30) aromatic ring substituted or unsubstituted fused ring groups or-N- (R) 21 )(R 22 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to one or more adjacent substituents to form one or more rings; provided that Ar is 6 To Ar 8 Represents a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (C6-C30) aryl groupSubstituted (3-to 30-membered) heteroaryl; and is also provided with
R 21 And R is 22 Each independently represents 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 substituted alkyl, the substituted alkenyl, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, the substituted cycloalkyl, the substituted cycloalkylene, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, and the one or more substituents of the substituted fused ring groups of the one or more aliphatic and one or more aromatic rings 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 unsubstituted or substituted by one or more (C6-C30) aryl groups; (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 one or more (C6-C30) aryl groups; (C6-C30) aryl unsubstituted or substituted with at least one of one or more (C1-C30) alkyl groups and one or more (3-to 30-membered) heteroaryl groups; tri (C1-C30) alkylsilyl; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; a fused ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings; an amino group; mono-or di- (C1-C30) alkylamino; mono-or di- (C2-C30) alkenylamino; substituted or unsubstituted 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; 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.
3. The plurality of host materials of claim 1, wherein formula 1 is represented by at least one of the following formulas 1-1 to 1-28:
in formulas 1-1 to 1-28,
X、R 1 to R 13 、L 1 To L 3 And Ar 1 To Ar 5 Is as defined in claim 1.
4. The plurality of host materials of claim 1, whichAr in formula 1 1 To Ar 5 And Ar in formula 2 6 To Ar 8 Each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted tetrabiphenyl group, a substituted or unsubstituted cumene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted benzophenanthryl groupA 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.
5. 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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6. 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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7. an organic electroluminescent device comprising 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 the plurality of host materials of claim 1.
8. An organic electroluminescent compound represented by the following formula 1':
in the formula 1' of the present invention,
x represents-N (R) -, -C (R') (R ") -or-Se-;
r, R 'and R' each independently represent a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (3-to 30-membered) heteroaryl group, -L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 ) The method comprises the steps of carrying out a first treatment on the surface of the Or R ' and R ' may be linked to each other to form one or more rings, and R ' may be the same or different;
R 1 to R 13 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 A substituted or unsubstituted fused ring group of a tri (C6-C30) arylsilyl group, one or more (C3-C30) aliphatic rings, and one or more (C6-C30) aromatic rings, -L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 ) The method comprises the steps of carrying out a first treatment on the surface of the Or may be attached to one or more adjacent substituents to form one or more rings;
provided that R, R ', R' and R 1 To R 13 At least one of them represents-L 1 -N-(Ar 1 )(Ar 2 ) or-L 2 -N(Ar 3 )-L 3 -N-(Ar 4 )(Ar 5 )；
L 1 And L 2 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;
L 3 represents a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (3-to 30-membered) heteroarylene group; and is also provided with
Ar 1 To Ar 5 Each independently represents a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C2-C30) alkenyl group, a substituted or unsubstituted condensed ring group of one or more (C3-C30) aliphatic rings and one or more (C6-C30) aromatic rings, a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (3-to 30-membered) heteroaryl group.
9. The organic electroluminescent compound according to claim 8, wherein the organic electroluminescent compound represented by formula 1' is selected from the group consisting of:
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10. an organic electroluminescent device comprising the organic electroluminescent compound according to claim 8.
11. An organic electroluminescent compound represented by any one of the following formulas 2'-1 to 2' -4:
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in the formulae 2'-1 to 2' -4,
t represents O or S;
X 1 ' to X 4 ' each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-to 30-membered) heteroaryl;
L 4 ' to L 6 ' each independently represents a single bond, unsubstituted or deuterium-substituted phenylene, or unsubstituted or deuterium-substituted naphthylene; and is also provided with
Ar 7 ' and Ar 8 ' each independently represents an unsubstituted or deuterium-substituted phenyl group, an unsubstituted or deuterium-substituted biphenyl group, an unsubstituted or deuterium-substituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzonaphthofuryl group, or a substituted or unsubstituted benzonaphthothienyl group;
in the formula 2' -1 of the present invention,
X 6 ' to X 8 ' each independently represents hydrogen, deuterium or-L 7 -Ar 9 Provided that X 6 ' to X 8 At least one of' represents-L 7 -Ar 9 ；
If X 6 ' is-L 7 -Ar 9 L is then 7 Represents a single bond, unsubstituted or deuterium-substituted phenylene group, or unsubstituted or deuterium-substituted naphthylene group, and Ar 9 Represents unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, or unsubstituted or deuterium-substituted naphthyl; provided that if L 7 Is a single bond, ar 9 Represents unsubstituted or deuterium-substituted naphthyl;
if X 7 ' is-L 7 -Ar 9 L is then 7 Represents a single bond, unsubstituted or deuterium-substituted phenylene group, or unsubstituted or deuterium-substituted naphthylene group, and Ar 9 Represents unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, or unsubstituted or deuterium-substituted naphthyl;
if X 8 ' is-L 7 -Ar 9 L is then 7 Represents a single bond, unsubstituted or deuterium-substituted phenylene group, or unsubstituted or deuterium-substituted naphthylene group, and Ar 9 Represents phenyl which is unsubstituted or substituted by deuterium, or naphthyl which is unsubstituted or substituted by deuterium; and is also provided with
Provided that if X 8 ' is-L 7 -Ar 9 And phenyl, then Ar 7 ' and Ar 8 At least one of' represents a dibenzofuranyl or dibenzothienyl group;
in the formula 2' -2 of the present invention,
X 8 ' represents-L 7 -Ar 9 And X is 5 ' and X 7 ' each independently represents hydrogen or deuterium;
L 7 represents a single bond, unsubstituted or deuterium-substituted phenylene group, or unsubstituted or deuterium-substituted naphthylene group, and Ar 9 Represents hydrogen, unsubstituted or deuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, or unsubstituted or deuterium-or one or more phenyl-substituted naphthyl; and is also provided with
Provided that if L 7 Is a single bond, ar 9 Represents unsubstituted or deuterium-substituted naphthyl;
in the formula 2' -3 of the present invention,
X 5 '、X 6 ' and X 8 ' each independently represents hydrogen, deuterium or-L 7 -Ar 9 Provided that X 5 '、X 6 ' and X 8 At least one of' represents-L 7 -Ar 9 ；
L 7 Represents a single bond, unsubstituted or deuterium-substituted phenylene group, or unsubstituted or deuterium-substituted naphthylene group, and Ar 9 Represents phenyl which is unsubstituted or substituted by deuterium or one or more naphthyl groups, biphenyl which is unsubstituted or substituted by deuterium, or naphthyl which is unsubstituted or substituted by deuterium; and is also provided with
Provided that if X 5 ' is-L 7 -Ar 9 And naphthyl, ar 7 ' and Ar 8 At least one of' represents a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted dibenzofuranyl group;
in the formula 2' -4, the amino acid sequence,
X 5 ' to X 7 ' each independently represents hydrogen, deuterium, or-L 7 -Ar 9 Provided that X 5 ' to X 7 At least one of' represents-L 7 -Ar 9 The method comprises the steps of carrying out a first treatment on the surface of the And is also provided with
L 7 Represents a single bond, unsubstituted or deuterium-substituted phenylene group, or unsubstituted or deuterium-substituted naphthylene group, and Ar 9 Representing unsubstituted orDeuterium-substituted phenyl, unsubstituted or deuterium-substituted biphenyl, or unsubstituted or deuterium-substituted naphthyl.
12. The organic electroluminescent compound according to claim 11, wherein the organic electroluminescent compound represented by any one of formulae 2'-1 to 2' -4 is selected from the group consisting of:
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13. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 11.
CN202310990273.4A 2022-08-09 2023-08-08 Multiple host materials, organic electroluminescent compounds, and organic electroluminescent device comprising the same Pending CN117586271A (en)

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KR10-2022-0099113 2022-08-09
KR10-2023-0090920 2023-07-13
KR1020230090920A KR20240021108A (en) 2022-08-09 2023-07-13 A plurality of host materials, organic electroluminescent compound, and organic electroluminescent device comprising the same

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