Multiple host materials and organic electroluminescent devices containing the same
By using multiple host materials combined with specific compounds in organic electroluminescent devices, the luminescence efficiency and service life of the device in long-term use and high-resolution display is solved, and higher performance performance is achieved.
Patent Information
- Application Number
- CN201980038446.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2019-04-16
- Filing Date
- 2019-05-09
- Publication Date
- 2025-03-28
- Estimated Expiration
- 2039-05-09
AI Technical Summary
Existing organic electroluminescent devices have problems with luminescence efficiency and service life in terms of long-term use and high-resolution display.
An organic electroluminescent device having long service life characteristics is formed by a plurality of host materials including at least one first host compound and at least one second host compound. Specific compounds are represented by Formula 1 and 2, and involve a variety of substituents and heterocyclic structures.
The long service life and high luminous efficiency of the organic electroluminescent device are achieved, showing significant improvements compared to the devices with a single conventional compound.
Smart Images

Figure BDA0002819570360000021 
Figure BDA0002819570360000022 
Figure BDA0002819570360000091
Abstract
Description
Technical Field
[0001] The present disclosure relates to a plurality of host materials and organic electroluminescent devices comprising the same. Background Art
[0002] In 1987, Tang et al. of Eastman Kodak first developed a small molecule green organic electroluminescent device (OLED) consisting of a TPD / Alq3 double layer consisting of a light-emitting layer and a charge transport layer. Since then, research on OLED has been rapidly developed and has been commercialized. Currently, phosphor materials provide excellent luminous efficiency in clear panels and are mainly used in organic electroluminescent devices. Displays with long-term use and high resolution require OLEDs with high luminous efficiency and / or long service life.
[0003] Korean Patent Application Publication No. 2018-0012709 discloses a diazadibenzoazulene fluorene derivative. However, the use as one of the plurality of host materials is not specifically disclosed, and the performance of the OLED device still needs to be improved. Summary of the invention
[0004] Issues to be resolved
[0005] An object of the present disclosure is to provide an organic electroluminescent device having a long lifespan characteristic by including a plurality of host materials including a specific compound combination.
[0006] Solution to the problem
[0007] The inventors of the present invention have found that the above objectives can be achieved by the following multiple host materials, wherein the multiple host materials include 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:
[0008]
[0009] in
[0010] X1 to X 13 Each independently represents N or CR1;
[0011] L1 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;
[0012] Ar represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, -NR5R6, or -SiR7R8R9; or may be linked to an adjacent substituent to form a ring;
[0013] R1 represents -L1-(Ar) a , hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR5R6, or -SiR7R8R9; or may be connected to an adjacent substituent to form a ring;
[0014] R5 to R9 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;
[0015] a represents an integer of 1 to 3, wherein if a is an integer of 2 or more, each Ar may be the same or different;
[0016]
[0017] in
[0018] HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group;
[0019] L2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group;
[0020] R 21 and R 22 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR5R6, or -SiR7R8R9; or may be linked to adjacent substituents to form a ring, provided that two adjacent R 21or two adjacent R 22 At least one of is connected to each other to form a ring; and
[0021] b represents an integer from 1 to 4, and c represents an integer from 1 to 6, wherein if b and c are integers of 2 or more, then R 21 Each and R 22 Each may be the same or different.
[0022] Effect of the Invention
[0023] By including a plurality of host materials disclosed herein, an organic electroluminescent device having a long lifespan characteristic is provided, and a display device or a lighting device can be manufactured using the organic electroluminescent device. DETAILED DESCRIPTION
[0024] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure and is not intended to limit the scope of the present disclosure in any way.
[0025] In the present disclosure, the term "organic electroluminescent compound" means a compound that can be used in an organic electroluminescent device and, if necessary, can be contained in any layer constituting the organic electroluminescent device.
[0026] In the present disclosure, the term "organic electroluminescent material" means a material that can be used for an organic electroluminescent device and can contain at least one compound. If necessary, the organic electroluminescent material can be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a luminescence auxiliary material, an electron blocking material, a luminescent material (host material or dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material.
[0027] In the present disclosure, the term "multiple host materials" means a host material including a combination of at least two compounds that can be included in any light-emitting layer constituting an organic electroluminescent device. It can mean both the material before being included in the organic electroluminescent device (for example, before vapor deposition) and the material after being included in the organic electroluminescent device (for example, after vapor deposition). For example, the multiple host materials of the present disclosure can be a combination of at least two host materials, and optionally, conventional materials contained in the organic electroluminescent material can be additionally included. By methods known in the art, at least two compounds included in the multiple host materials of the present disclosure can be simultaneously included in one light-emitting layer, or can be each included in a different light-emitting layer. For example, the at least two compounds can be mixed evaporated or co-evaporated, or evaporated separately.
[0028] Hereinafter, the compounds represented by Formulae 1 and 2 will be described in detail.
[0029] Here, the term "(C1-C30) alkyl" means a straight or branched alkyl having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 10, and more preferably 1 to 6. The above alkyl groups may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. Here, the term "(C3-C30) cycloalkyl" means a mono- or polycyclic hydrocarbon having 3 to 30 ring skeleton carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The above cycloalkyl groups may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. The term "(3- to 7-membered) heterocycloalkyl" means a cycloalkyl having 3 to 7 ring skeleton atoms and including at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, and preferably the group consisting of O, S, and N. The above heterocycloalkyl groups may include tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc. The term "(C6-C30) aryl" or "(C6-C30) arylene" means a monocyclic or condensed ring group derived from an aromatic hydrocarbon having 6 to 30 ring skeleton carbon atoms, wherein the number of carbon atoms in the ring skeleton is preferably 6 to 20, more preferably 6 to 15. The above aryl or arylene groups may be partially saturated. The above aryl groups may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, peryl, The above aryl groups may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthrenyl, 2-phenanthrenyl, 3-phenanthrenyl, 4-phenanthrenyl, 9-phenanthrenyl, naphthacenyl, pyrenyl, 1-chrysene, 2-chrysene, 3-chrysene, 4-chrysene, 5-chrysene, 6-chrysene, benzo[c]phenanthrenyl, benzo[g]phenanthrenyl, 1-triphenylenyl group, 2-triphenylenyl group, 3-triphenylenyl group, 4-triphenylenyl group, group), 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenyl, 3-biphenyl, 4-biphenyl, o-terphenyl group, 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-quaterphenyl group, 3-fluoranthene, 4-fluoranthene, 8-fluoranthene, 9-fluoranthene, benzofluoranthene, o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3- , 4-xylyl, 2,5-xylyl, mesityl, o-cumyl, m-cumyl, p-cumyl, p-tert-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, and 9,9-diphenyl -4-fluorenyl. The term "(3- to 30-membered) heteroaryl" or "(3- to 30-membered) heteroarylene" refers to an aryl group having 3 to 30 ring skeleton atoms, wherein the number of the ring skeleton atoms is preferably 3 to 20, more preferably 5 to 15, and includes at least one (preferably 1 to 4) heteroatom selected from the group consisting of B, N, O, S, Si, and P. The above heteroaryl or heteroarylene group may be a monocyclic ring, or a condensed ring condensed with at least one benzene ring; may be partially saturated; and may be obtained by separating at least one heteroaryl or Aryl is connected to heteroaryl via one or more single bonds to form heteroaryl or heteroarylene. The above heteroaryl can include monocyclic heteroaryl, such as furanyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl; and condensed ring heteroaryl, such as benzofuranyl, benzothiophenyl, isobenzofuranyl,dibenzofuranyl, dibenzothiophenyl, benzonaphthothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl and the like. More specifically, the above heteroaryl or heteroarylene group may include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidyl, 4-pyrimidyl, 5-pyrimidyl, 6-pyrimidyl, 1,2,3-triazine-4-yl, 1,2,4-triazine-3-yl, 1,3,5-triazine-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolyl, 2-indolyl, 3-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 8-indolyl, 2-imidazopyridyl, 3-imidazopyridyl, 5-imidazopyridyl, , 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 3-pyridinyl, 4-pyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furanyl, 3-furanyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl, 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl-1-yl, azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl group), 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl,3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl , 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-silafluorenyl group, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl group, 2-germafluorenyl, 3-germafluorenyl, and 4-germafluorenyl. In addition, the "halogen" includes F, Cl, Br, and I. ,
[0030] In addition, "ortho", "meta", and "para" represent the substitution positions of two substituents. The ortho position represents the position that is directly adjacent, and for example, represents the 1,2 position in the case of benzene. The meta position represents the position adjacent to the directly adjacent position, and for example, represents the 1,3 position in the case of benzene. The para position represents the position adjacent to the meta position, and for example, represents the 1,4 position in the case of benzene.
[0031] Here, in the expression "substituted or unsubstituted", "substituted" means that the hydrogen atom in some functional groups is replaced by another atom or functional group (i.e., a substituent). In the formula of the present disclosure, the substituents of substituted alkyl, substituted cycloalkyl, substituted cycloalkylene, substituted cycloalkenyl, substituted heterocycloalkyl, substituted aryl, substituted arylene, substituted heteroaryl, and substituted heteroarylene are each independently selected from at least one of the following groups, which consists of the following: deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; (C1-C30) alkyl; halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2 -C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (3- to 30-membered)heteroaryl, (C6-C30)aryl, or di(C6-C30)arylamino, which is unsubstituted or substituted with (C1-C30)alkyl; (C6-C30)alkylthio; (C3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (3- to 30-membered)heteroaryl, (C6-C30)aryl, or di(C6-C30)arylamino, which is unsubstituted or substituted with cyano )aryl, (3- to 30-membered)heteroaryl, or tri(C6-C30)arylsilyl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; mono- or di-(C1-C30)alkylamino; mono- or di-(C6-C30)arylamino; (C 1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylborylcarbonyl; di(C1-C30)alkylborylcarbonyl; (C1-C30)alkyl(C6-C30)arylborylcarbonyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl. Preferably, the substituents are each independently at least one selected from the group consisting of (C1-C6)alkyl, (C6-C20)aryl, and (3- to 20-membered)heteroaryl. For example, the substituents may be methyl, phenyl, naphthyl, biphenyl, or naphthylphenyl.
[0032] In the formula of the present disclosure, if a substituent is connected to an adjacent substituent to form a ring, the ring may be a substituted or unsubstituted, mono- or polycyclic, alicyclic or aromatic (3- to 30-membered) ring, or a combination thereof, wherein the formed ring may contain at least one heteroatom selected from nitrogen, oxygen and sulfur. For example, the condensed ring may be a substituted or unsubstituted dibenzothiophene ring, a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted phenanthrene ring, a substituted or unsubstituted fluorene ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted indole ring, a substituted or unsubstituted indene ring, a substituted or unsubstituted benzene ring, or a substituted or unsubstituted carbazole ring.
[0033] In the formula of the present disclosure, the heteroaryl group or the heteroarylene group may each independently contain at least one heteroatom selected from B, N, O, S, Si, and P. In addition, the heteroatom may be substituted with at least one substituent 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 (5- 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 (C1-C30) alkylsilyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5- to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri( ... substituted 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-(C6-C30)arylamino, and substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino.
[0034] In Formula 1, X1 to X 13 Each independently represents N or CR1. According to one embodiment of the present disclosure, X1 to X 13 All are CR1.
[0035] In Formula 1, L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (C3-C30)cycloalkylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene. According to one embodiment of the present disclosure, L1 represents a single bond, or an unsubstituted or (C1-C6)alkyl-substituted (C6-C15)arylene. According to another embodiment of the present disclosure, L1 represents a single bond or an unsubstituted (C6-C12)arylene. Specifically, L1 may represent a single bond, a phenylene, a naphthylene, a biphenylene, a dimethylfluorenylene, and the like.
[0036] In Formula 1, Ar represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR5R6, or -SiR7R8R9; or may be connected to adjacent substituents to form a ring. Here, R5 to R9 each independently represent a substituted or unsubstituted (C1-C30) alkyl, a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl. According to one embodiment of the present disclosure, Ar represents hydrogen, unsubstituted or (C1-C6) alkyl-substituted (C6-C20) aryl, unsubstituted or (C6-C12) aryl-substituted (5- to 25-membered) heteroaryl, or -NR5R6; and R5 and R6 each independently represent unsubstituted or (C1-C6) alkyl-substituted (C6-C20) aryl, or unsubstituted (5- to 15-membered) heteroaryl. According to another embodiment of the present disclosure, Ar represents unsubstituted (C6-C20) aryl, unsubstituted (5- to 20-membered) heteroaryl, or -NR5R6; and R5 and R6 each independently represent unsubstituted (C6-C20) aryl. Specifically, Ar can represent hydrogen, phenyl, naphthyl, biphenyl, naphthylphenyl, phenylnaphthyl, terphenyl, dimethylfluorenyl, dimethylbenzofluorenyl, dibenzofuranyl, benzonaphthofuranyl, dibenzothiophenyl, benzonaphthothiophenyl, carbazolyl, phenylcarbazolyl, benzocarbazolyl, phenylbenzocarbazolyl, dibenzocarbazolyl, -NR5R6, etc.; and R5 and R6 can each independently represent phenyl, naphthyl, biphenyl, naphthylphenyl, dimethylfluorenyl, dibenzofuranyl, etc.
[0037] According to one embodiment of the present disclosure, Ar may represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthylphenyl group, a substituted or unsubstituted phenylnaphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted dibenzocarbazolyl group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzonaphthothiophene group, or a substituted or unsubstituted terphenyl group. The amino group may be a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzonaphthofuranyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted diphenylamino, a substituted or unsubstituted phenylbiphenylamino, a substituted or unsubstituted naphthylbiphenylamino, a substituted or unsubstituted dibiphenylamino, a substituted or unsubstituted biphenylfluorenylamino, or a substituted or unsubstituted biphenyldibenzofuranylamino.
[0038] In Formula 1, R1 represents -L1-(Ar) a , hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR5R6, or -SiR7R8R9; or may be connected to an adjacent substituent to form a ring. According to one embodiment of the present disclosure, R1 represents hydrogen, unsubstituted (C6-C12) aryl, or unsubstituted (5- to 15-membered) heteroaryl; or may be connected to an adjacent substituent to form an unsubstituted monocyclic (6- to 12-membered) aromatic ring. Specifically, R1 may represent hydrogen, phenyl, dibenzofuranyl, dibenzothiophenyl, or the like, or may be connected to an adjacent substituent to form a benzene ring, or the like.
[0039] Formula 1 can be represented by the following formula 1-1:
[0040]
[0041] in
[0042] L1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene group;
[0043] Ar represents hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, or -NR5R6;
[0044] R5 and R6 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;
[0045] R 11 To R 14 Each is independently the same as defined in R1 in Formula 1; and
[0046] aa represents an integer of 1 to 3, ab and ac each independently represent an integer of 1 to 4, and ad represents 1 or 2, wherein if aa, ab, ac, and ad are integers of 2 or more, then R 11 Each, R 12 Each, R 13 Each, and R 14 Each may be the same or different.
[0047] In addition, Formula 1 may be represented by at least one of the following Formulas 1-11 to 1-40:
[0048]
[0049] in
[0050] L1 represents a single bond, or is represented by one of the following formulae L1-1 to L1-7, and
[0051]
[0052] Ar is represented by one of the following formulae Ar-1 to Ar-121.
[0053]
[0054]
[0055]
[0056] In Formula 2, HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group. According to one embodiment of the present disclosure, HAr represents a (3- to 15-membered) heteroaryl group substituted by one or more (C6-C20) aryl groups. According to another embodiment of the present disclosure, HAr represents a (3- to 15-membered) heteroaryl group substituted by one or more (C6-C12) aryl groups. Specifically, HAr may represent a pyridyl group substituted by one or more phenyl groups; a pyrimidyl group substituted by one or more phenyl groups; a triazine group substituted by one or more selected from phenyl, naphthyl, and biphenyl; a quinazolinyl group substituted by one or more selected from phenyl, naphthyl, biphenyl, and naphthylphenyl; a quinoxalinyl group substituted by one or more selected from phenyl, naphthyl, biphenyl, naphthylphenyl, etc.
[0057] According to one embodiment of the present disclosure, HAr may represent a substituted or unsubstituted triazine group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinazoline group, a substituted or unsubstituted benzoquinazoline group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted quinoline group, a substituted or unsubstituted benzoquinoline group, a substituted or unsubstituted isoquinoline group, a substituted or unsubstituted benzoisoquinoline group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted naphthyridinyl group, or a substituted or unsubstituted benzothienopyrimidinyl group.
[0058] In Formula 2, L2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene. According to one embodiment of the present disclosure, L2 represents a single bond, or an unsubstituted or (C1-C6)alkyl-substituted (C6-C20)arylene. According to another embodiment of the present disclosure, L2 represents a single bond, or an unsubstituted or (C1-C6)alkyl-substituted (C6-C15)arylene. Specifically, L2 may represent a single bond, a phenylene, a naphthylene, a biphenylene, a dimethylfluorenylene, a dimethylbenzofluorenylene, and the like.
[0059] In formula 2, R 21 and R 22 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR5R6, or -SiR7R8R9; or may be linked to adjacent substituents to form a ring, provided that two adjacent R 21 or two adjacent R 22 At least one of is connected to each other to form a ring. According to one embodiment of the present disclosure, R 21 and R 22 Each independently represents hydrogen, or unsubstituted (C6-C12) aryl, or two adjacent R 21 or two adjacent R 22 are connected to each other to form a polycyclic aromatic ring. Specifically, R 21 and R 22 They may each independently represent hydrogen, phenyl, etc., or two adjacent R 21 or two adjacent R 22They are connected to each other to form a benzene ring, an indole ring substituted with a phenyl group, a benzoindole ring substituted with one or more selected from a phenyl group and a biphenyl group, a benzofuran ring, a benzothiophene ring, or the like.
[0060] Formula 2 may be represented by at least one of the following Formulas 2-1 to 2-6:
[0061]
[0062]
[0063] in
[0064] HAr and L2 are defined as in Equation 2;
[0065] R 31 To R 44 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR5R6, or -SiR7R8R9; or may be connected to adjacent substituents to form a ring;
[0066] V and W each independently represent NR 16 , O, or S;
[0067] R 16 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered)heteroaryl group; and
[0068] d, h, i, j, l, n, o, p, and q each independently represent an integer of 1 to 4, and e, f, g, k, and m each independently represent an integer of 1 to 6, wherein if d to q are integers of 2 or more, then R 31 Each to R 44 Each may be the same or different.
[0069] In addition, Formula 2 can be represented by at least one of the following Formulas 2-11 to 2-38.
[0070]
[0071]
[0072] in
[0073] HAr is represented by one of the following formulas 2-40 to 2-58, and
[0074]
[0075] L2 is represented by one of the following formulae 3-1 to 3-47.
[0076]
[0077] The compound represented by Formula 1 includes the following compounds, but is not limited thereto.
[0078]
[0079]
[0080]
[0081] The compound represented by Formula 2 includes the following compounds, but is not limited thereto.
[0082]
[0083]
[0084]
[0085]
[0086]
[0087] The compound represented by Formula 1 according to the present disclosure can be prepared by a synthesis method known to those skilled in the art. For example, it can be prepared by referring to Korean Patent Application Publication No. 2018-0012709 (published on February 6, 2018), but is not limited thereto.
[0088] The compound represented by Formula 2 according to the present disclosure can be prepared by a synthesis method known to those skilled in the art. For example, it can be prepared by referring to Korean Patent Application Publication Nos. 2015-0032447 (published on March 26, 2015), 2015-0077513 (published on July 8, 2015), and 2015-0135109 (published on December 2, 2015), but is not limited thereto.
[0089] An organic electroluminescent device according to the present disclosure includes a first electrode; a second electrode; and at least one organic layer between the first and second electrodes.
[0090] One of the first and second electrodes may be an anode, and the other may be a cathode. The organic layer comprises a light-emitting layer, and may further comprise at least one layer selected from the following: a hole injection layer, a hole transport layer, a hole auxiliary layer, a light-emitting auxiliary layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. Here, the second electrode may be a semi-transmissive reflective electrode or a reflective electrode, and may be a top-emitting, bottom-emitting, or two-sided emitting type, depending on the material used. In addition, the hole injection layer may be further doped with a p-type dopant, and the electron injection layer may be further doped with an n-type dopant.
[0091] The organic electroluminescent device according to the present disclosure includes an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein at least one layer of the light-emitting layer includes a compound represented by Formula 1 and a compound represented by Formula 2.
[0092] The light-emitting layer includes a host and a dopant, and the host includes a plurality of host materials. The compound represented by Formula 1 may be included as a first host compound of the plurality of host materials, and the compound represented by Formula 2 may be included as a second host compound of the plurality of host materials. Here, the weight ratio of the first host compound to the second host compound is in the range of 1:99 to 99:1.
[0093] The light-emitting layer is a layer from which light is emitted, and may be a single layer or a multilayer in which two or more layers thereof are stacked. In the plurality of host materials according to the present disclosure, the first and second host materials may be simultaneously contained in one layer or may be respectively contained in different light-emitting layers. According to one embodiment of the present disclosure, the doping concentration of the dopant compound relative to the host compound of the light-emitting layer may be less than 20wt%.
[0094] The organic electroluminescent device of the present disclosure may further include at least one layer selected from the following: a hole injection layer, a hole transport layer, a hole auxiliary layer, a luminescent auxiliary layer, an electron transport layer, an electron injection layer, an intermediate layer, an electron buffer layer, a hole blocking layer, and an electron blocking layer. In one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may further include an amine-based compound other than the multiple main materials of the present disclosure as at least one of the hole injection material, the hole transport material, the hole auxiliary material, the luminescent material, the luminescent auxiliary material, and the electron blocking material. In addition, in one embodiment of the present disclosure, the organic electroluminescent device of the present disclosure may further include an azine-based compound other than the multiple main materials of the present disclosure as at least one of the electron transport material, the electron injection material, the electron buffer material, and the hole blocking material.
[0095] The dopant contained in the organic electroluminescent device according to the present disclosure may be at least one phosphorescent or fluorescent dopant, and 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 selected from metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), preferably ortho-metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and more preferably ortho-metallized iridium complex compounds.
[0096] The dopant included in the organic electroluminescent device of the present disclosure may include a compound represented by the following Formula 101, but is not limited thereto.
[0097]
[0098] In Formula 101, L is selected from the following structures 1 and 2:
[0099]
[0100] R 100 To R 103 each independently represents hydrogen, deuterium, halogen, unsubstituted or halogen-substituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, cyano, substituted or unsubstituted (3- to 30-membered)heteroaryl, or substituted or unsubstituted (C1-C30)alkoxy; or may be connected to an adjacent substituent to form a substituted or unsubstituted condensed ring with pyridine, such as a substituted or unsubstituted quinoline, substituted or unsubstituted benzofuranopyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranoquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline ring;
[0101] R 104 To R 107 Each independently represents hydrogen, deuterium, halogen, unsubstituted or halogen-substituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, cyano, or substituted or unsubstituted (C1-C30)alkoxy; or may be connected to an adjacent substituent to form a substituted or unsubstituted condensed ring with benzene, such as a substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuranopyridine, or substituted or unsubstituted benzothienopyridine ring;
[0102] R 201 To R 211 Each independently represents hydrogen, deuterium, halogen, unsubstituted or halogen-substituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, or substituted or unsubstituted (C6-C30)aryl; or may be connected to an adjacent substituent to form a substituted or unsubstituted condensed ring; and
[0103] r represents an integer of 1 to 3.
[0104] Specific examples of the dopant compound are as follows, but are not limited thereto.
[0105]
[0106]
[0107]
[0108]
[0109] In the organic electroluminescent device of the present disclosure, 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. Multiple hole injection layers may be used to reduce the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or the electron blocking layer. Two compounds may be used simultaneously for each layer. The hole transport layer or the electron blocking layer may also form multiple layers.
[0110] In addition, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used between the light-emitting layer and the cathode. Multiple electron buffer layers can be used to control electron injection and enhance the interface characteristics between the light-emitting layer and the electron injection layer. Two compounds can be used for each layer at the same time. The hole blocking layer or the electron transport layer can also be formed by multiple layers, and each layer can contain two or more compounds.
[0111] In addition, the organic electroluminescent compound or a plurality of host materials according to the present disclosure may also be used in an organic electroluminescent device including quantum dots (QDs).
[0112] To form each layer of the organic electroluminescent device of the present disclosure, a dry film forming method such as vacuum evaporation, sputtering, plasma and ion plating methods, or a wet film forming method such as inkjet printing, nozzle printing, slit coating, spin coating, dip coating, and flow coating methods can be used.
[0113] When a solvent is used in the wet film formation method, a thin film can be formed by dissolving or diffusing the materials forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent may be any solvent in which the materials forming each layer can be dissolved or diffused and in which there is no problem in film forming ability.
[0114] In addition, the first and second host compounds of the present disclosure can be subjected to film formation in the above-listed methods, typically by a co-evaporation method or a mixed evaporation method. Co-evaporation is a mixed deposition method in which two or more materials are placed in respective separate crucible sources and current is applied to both units simultaneously to evaporate the materials. Mixed evaporation is a mixed deposition method in which two or more materials are mixed in one crucible source before evaporating them, and current is applied to the units to evaporate the materials.
[0115] The present disclosure can provide a display device by using a plurality of host materials comprising a compound represented by Formula 1 and a compound represented by Formula 2. That is, it is possible to manufacture a display system or a lighting system by using a plurality of host materials of the present disclosure. Specifically, it is possible to produce a display system, such as a display system for a smart phone, a tablet computer, a notebook, a PC, a TV, or a car, or to produce a lighting system, such as an outdoor or indoor lighting system, by using a plurality of host materials of the present disclosure.
[0116] Hereinafter, it is described whether the luminous efficiency and / or service life characteristics of the OLED device can be improved by including multiple host materials of the present disclosure. However, the following examples are used to explain the performance of the OLED device including multiple host materials according to the present disclosure in order to understand the present disclosure in detail, and the present disclosure is not limited to the following examples.
[0117] Device Examples 1-13: Production of OLED Devices Comprising Multiple Host Materials According to the Disclosure
[0118] An organic light emitting diode (OLED) device containing multiple host materials according to the present disclosure was produced. A transparent electrode indium tin oxide (ITO) film (10Ω / sq) on a glass substrate for an OLED device (Geomatec, Japan) was ultrasonically cleaned sequentially with trichloroethylene, acetone, ethanol, and distilled water, and then stored in isopropanol. The ITO substrate was then mounted on a substrate holder of a vacuum vapor deposition device. Compound HI-1 was introduced into a unit of the vacuum vapor deposition device, and then the pressure in the device chamber was controlled to 10 -6Support. Thereafter, an electric current is applied to the unit to evaporate the above introduced materials, thereby forming a first hole injection layer with a thickness of 80nm on the ITO substrate. Compound HI-2 is then introduced into another unit of the vacuum vapor deposition device, and evaporated by applying an electric current to the unit, thereby forming a second hole injection layer with a thickness of 5nm on the first hole injection layer. Compound HT-1 is introduced into another unit of the vacuum vapor deposition device, and evaporated by applying an electric current to the unit, thereby forming a first hole transport layer with a thickness of 10nm on the second hole injection layer. The second hole transport material listed in Table 1 below is introduced into another unit of the vacuum vapor deposition device, and evaporated by applying an electric current to the unit, thereby forming a second hole transport layer with a thickness of 60nm on the first hole transport layer. After forming these hole injection layers and hole transport layers, the light-emitting layer is then deposited as follows. The first and second host compounds shown in Table 1 below are introduced into two units of a vacuum vapor deposition device as the main body, and compound D-39 is introduced into another unit. The two main materials are evaporated at a rate of 1:1, and the dopant materials are evaporated simultaneously at different rates, and these are deposited at a doping amount of 3wt% based on the total amount of the main body and the dopant to form a light-emitting layer with a thickness of 40nm on the second hole transport layer. Compound ET-1 and compound EI-1 are then introduced into two other units, evaporated at a rate of 1:1, and deposited to form an electron transport layer with a thickness of 35nm on the light-emitting layer. Then, after depositing compound EI-1 as an electron injection layer with a thickness of 2nm on the electron transport layer, an Al cathode with a thickness of 80nm is deposited on the electron injection layer by another vacuum vapor deposition device. An OLED device is thus produced.
[0119] The time it takes for the brightness of the OLEDs produced above to decrease from 100% to 90% (lifetime; T90) at a brightness of 5,000 nits at constant current is provided in Table 1 below.
[0120] [Table 1]
[0121]
[0122] *In Device Example 7, the first and second host materials were premixed and evaporated in a 1:1 ratio.
[0123] Comparative Examples 1 and 2: Production of OLED devices containing conventional compounds as hosts
[0124] An OLED device was produced in the same manner as in Device Example 1, except for the following: a material listed in the following Table 2 was introduced as a second hole transport material and a single compound listed in the following Table 2 was used as a host.
[0125] The time it takes for the brightness of the OLEDs produced above to decrease from 100% to 90% (lifetime; T90) at a brightness of 5,000 nits at constant current is provided in Table 2 below.
[0126] [Table 2]
[0127]
[0128] It is confirmed from Tables 1 and 2 that the organic electroluminescent device including the compounds represented by Formulae 1 and 2 of the present disclosure as a plurality of host materials has greatly improved lifespan characteristics compared to an organic electroluminescent device including a single conventional organic electroluminescent compound.
[0129] The compounds used in the device examples and comparative examples are shown in Table 3 below.
[0130] [Table 3]
[0131]
Claims
1. A plurality of host materials, the 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 at least one of the following formulas 2-1 to 2-6: in X1 to X 13 Each independently represents N or CR1; L1 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 represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C3-C30)cycloalkenyl, substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, -NR5R6, or -SiR7R8R9; or may be linked to an adjacent substituent to form a ring; R1 represents -L1-(Ar) a , hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR5R6, or -SiR7R8R9; or may be connected to an adjacent substituent to form a ring; R5 to R9 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; a represents an integer of 1 to 3, wherein if a is an integer of 2 or more, each Ar may be the same or different; in HAr represents a substituted or unsubstituted (3- to 30-membered) heteroaryl group; L2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (3- to 30-membered)heteroarylene group; R 31 To R 44 Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, -NR5R6, or -SiR7R8R9; or may be connected to adjacent substituents to form a ring; V and W each independently represent NR 16 , O, or S; R 16 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3- to 30-membered)heteroaryl group; and d, h, i, j, l, n, o, p, and q each independently represent an integer of 1 to 4, and e, f, g, k, and m each independently represent an integer of 1 to 6, wherein if d to q are integers of 2 or more, then R 31 Each to R 44 Each may be the same or different.
2. The plurality of host materials according to claim 1, wherein Formula 1 is represented by the following Formula 1-1: in L1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene group; Ar represents hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3- to 30-membered)heteroaryl, or -NR5R6; R5 and R6 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; R 11 To R 14 Each independently has the same definition as R1 in claim 1; and aa represents an integer of 1 to 3, ab and ac each independently represent an integer of 1 to 4, and ad represents 1 or 2, wherein if aa, ab, ac, and ad are integers of 2 or more, then R 11 Each, R 12 Each, R 13 Each, and R 14 Each may be the same or different.
3. The plurality of host materials according to claim 1, wherein in Formula 1, Ar represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthylphenyl group, a substituted or unsubstituted phenylnaphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted dibenzocarbazolyl group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzonaphthyl group, or a substituted or unsubstituted benzonaphthyl group. substituted or unsubstituted benzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted phenylbiphenylamino, substituted or unsubstituted naphthylbiphenylamino, substituted or unsubstituted dibiphenylamino, substituted or unsubstituted biphenylfluorenylamino, or substituted or unsubstituted biphenyldibenzofuranylamino.
4. A plurality of host materials according to claim 1, wherein in Formulas 2-1 to 2-6, HAr represents a substituted or unsubstituted triazine group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinazoline group, a substituted or unsubstituted benzoquinazoline group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinoxalinyl group, a substituted or unsubstituted quinoline group, a substituted or unsubstituted benzoquinoline group, a substituted or unsubstituted isoquinoline group, a substituted or unsubstituted benzoisoquinoline group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted naphthyridinyl group, or a substituted or unsubstituted benzothienopyrimidinyl group.
5. The plurality of host materials according to claim 1, wherein Formula 1 is represented by at least one of the following Formulas 1-11 to 1-40: in L1 represents a single bond, or is represented by one of the following formulae L1-1 to L1-7, and Ar is represented by one of the following formulae Ar-1 to Ar-121:
6. The plurality of host materials according to claim 1, wherein Formulas 2-1 to 2-6 are represented by at least one of the following Formulas 2-11 to 2-38: in HAr is represented by one of the following formulas 2-40 to 2-58, and L2 is represented by one of the following formulas 3-1 to 3-47:
7. The plurality of host materials according to claim 1, wherein the compound represented by Formula 1 is selected from the following compounds:
8. The plurality of host materials according to claim 1, wherein the compound represented by at least one of Formulae 2-1 to 2-6 is selected from the following compounds: 9 . An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein at least one layer of the light-emitting layer comprises a plurality of host materials according to claim 1 .
Citation Information
Patent Citations
Organic Electroluminescent Compound and Organic Electroluminescent Device Comprising the Same
KR1020180012709A