Host materials and organic electroluminescent devices containing same - Patents.com

By employing phenanthrooxazole and phenanthrothiazole-based host materials with triazine and pyrimidine derivatives, the efficiency and lifetime of organic electroluminescent devices are enhanced, addressing the limitations of existing technologies in achieving high luminous efficiency and long lifetime.

JP7609836B2Active Publication Date: 2025-01-07DUPONT SPECIALTY MATERIALS KOREA LTD

Patent Information

Application Number
JP2022172306
Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Priority Date
2018-02-21
Filing Date
2022-10-27
Publication Date
2025-01-07
Estimated Expiration
2038-02-23

AI Technical Summary

Technical Problem

Existing organic electroluminescent devices face challenges in achieving high luminous efficiency and long lifetime, particularly in medium- and large-sized OLED panels, with a need for host materials that provide thermal stability, electrochemical stability, and improved intermolecular stacking for efficient electron transport.

Method used

The use of phenanthrooxazole and phenanthrothiazole-based compounds as host materials, combined with triazine and pyrimidine derivatives, enhances intermolecular charge transitions and molecular orientation, leading to improved current and power efficiency, and low driving voltages in organic electroluminescent devices.

Benefits of technology

This combination results in organic electroluminescent devices with high efficiency, long lifetime, and fast driving voltage characteristics, maintaining high purity color and reducing the driving voltage.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure 0007609836000034
    Figure 0007609836000034
  • Figure 0007609836000001
    Figure 0007609836000001
  • Figure 0007609836000002
    Figure 0007609836000002
Patent Text Reader

Abstract

To provide an organic electroluminescent device that exhibits excellent life characteristics while maintaining high luminous efficiency. The present invention provides a plurality of host materials including at least one first host compound and at least one second host compound, wherein the first host compound is represented by Formula 1 below: TIFF2023011751000040.tif57157
Need to check novelty before this filing date? Find Prior Art

Description

[Technical field]

[0001] The present disclosure relates to a number of host materials and organic electroluminescent devices containing same. [Background technology]

[0002] Electroluminescent devices (EL devices) are self-emitting display devices that have the advantages of providing wider viewing angles, greater contrast ratios and faster response times. The first organic EL device was developed by Eastman Kodak in 1987 using small aromatic diamine molecules and aluminum complexes as materials to form the light-emitting layer (see Appl. Phys. Lett. 51, 913, 1987).

[0003] An organic electroluminescent device (OLED) converts electrical energy into light by applying electricity to an organic electroluminescent material, and typically includes an anode, a cathode, and an organic layer formed between the two electrodes. The organic layers of an organic EL device may include a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer (containing a host material and a dopant material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. The materials used in the organic layers can be classified into hole injection materials, hole transport materials, electron blocking materials, emitting materials, electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc. according to their functions. In an organic EL device, holes from the anode and electrons from the cathode are injected into the emitting layer by applying a voltage, and excitons having high energy are generated by the recombination of the holes and electrons. When an organic light-emitting compound returns from an excited state to a ground state, it transitions to an excited state by the energy and emits light from the energy.

[0004] The most important factor determining the luminous efficiency in an organic EL device is the luminescent material. The luminescent material is required to have the characteristics of high quantum efficiency, high mobility of electrons and holes, and uniformity and stability of the formed luminescent material layer. The luminescent material is classified into blue, green, and red luminescent materials according to the luminescent color, and further includes yellow or orange luminescent materials. Furthermore, the luminescent material is classified into host materials and dopant materials according to the function. In recent years, an urgent task is the development of organic EL devices with high efficiency and long life. In particular, considering the EL characteristics required for medium and large OLED panels, there is an urgent need to develop a very excellent luminescent material that surpasses conventional materials. For this purpose, preferably, as a solid-state solvent and energy transmitter, the host material should have high purity and suitable molecular weight for deposition under vacuum. In addition, the host material is required to have high glass transition temperature and thermal decomposition temperature to achieve thermal stability, high electrochemical stability to achieve long life, easy formability of amorphous thin film, good adhesion with adjacent layers, and no interlayer migration.

[0005] The combination of host and dopant can be used as luminescent material to improve color purity, luminous efficiency and stability.Generally, EL devices with excellent properties have a structure that includes a luminescent layer formed by doping dopant into host.When using such a dopant / host material system as luminescent material, host material has a great influence on the efficiency and life of EL device, so their selection is important.

[0006] JP 2001-23777 A discloses an organic electroluminescent device using a compound in which a nitrogen-containing 5-membered heteroaryl is condensed with a middle benzene ring of a phenanthrene skeleton as a host material. The organic electroluminescent device containing the compound disclosed in the document shows excellent blue color purity characteristics. However, the document does not disclose a mixed structure of the phosphorescent light-emitting layer, and the driving voltage, current efficiency, and driving life are still in need of improvement. Summary of the Invention [Problem to be solved by the invention]

[0007] An object of the present disclosure is to provide an organic electroluminescent device that has a long lifetime while maintaining high luminous efficiency. [Means for solving the problem]

[0008] As a result of intensive research to solve the above technical problems, the present inventors have found that the above-mentioned object can be achieved by a plurality of host materials including at least one first host compound represented by the following formula 1 or 2 and at least one second host compound represented by the following formula 3, and have completed the present invention. [ka] (In the formula, X 1 -N=, -NR 7 represents -, -O- or -S-; Y 1 -N=, -NR 8 -, -O- or -S-, except that X 1 When represents -N=, Y 1 -NR 8 represents -, -O- or -S-; X 1 Ga-NR 7 When expressing -, Y 1 represents -N=, -O- or -S-; R 1 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl; R 2 ~R 8are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 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 tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or may combine with adjacent substituents to form a substituted or unsubstituted (C3-C30)monocyclic or polycyclic, alicyclic, or aromatic ring, whose carbon atoms may be replaced by at least one heteroatom selected from nitrogen, oxygen, and sulfur; L 1 represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; a represents 1, b and c each independently represent 1 or 2, and d and e each independently represent an integer from 1 to 4; Heteroaryl(ene) contains at least one heteroatom selected from B, N, O, S, Si, and P. [ka] (In the formula, X 11 -N=, -NR 17 represents -, -O- or -S-; Y 11 -N=, -NR 18 -, -O- or -S-, except that X 11 When represents -N=, Y 11 -NR 18 represents -, -O- or -S-; X 11 Ga-NR 17 When expressing -, Y11 represents -N=, -O- or -S-; X represents N or CH; R 11 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl; R 12 ~R 18 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 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 tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or may combine with adjacent substituents to form a substituted or unsubstituted (C3-C30)monocyclic or polycyclic, alicyclic, or aromatic ring, whose carbon atoms may be replaced by at least one heteroatom selected from nitrogen, oxygen, and sulfur; L 2 represents a single bond, a substituted or unsubstituted (C6 to C30) arylene, or a substituted or unsubstituted (3 to 30 membered) heteroarylene; a' represents 1, b' and c' each independently represent 1 or 2, and d' represents an integer of 1 to 4; Heteroaryl(ene) contains at least one heteroatom selected from B, N, O, S, Si, and P.

[0009] Advantageous Effects of the Invention The phenanthroxazole-based and phenanthrothiazole-based compounds according to the present disclosure have inherently high electronegativity and electron-rich groups, and have rigid properties as structures in which phenanthrene and oxazole, or phenanthrene and thiazole, etc. are condensed, and the above compounds of the present disclosure promote intermolecular charge transfer. Furthermore, when such intermolecular stacking is strengthened, it is easy to introduce horizontal molecular orientation, and thus fast electron current characteristics can be introduced. Therefore, by using limited structures such as triazine and pyrimidine derivatives as luminescent materials, it is possible to provide an organic electroluminescent device that shows a relatively low driving voltage by improving current efficiency and power efficiency, as well as interface properties such as high purity color and excellent luminous efficiency, while maintaining the intermolecular stacking effect together with the electron transport layer.

[0010] Furthermore, when using a light-emitting material that mixes a hole-type amine substituted with a phenanthroxazole-based compound and a phenanthrothiazole-based compound as a first host and an electron-type azine material substituted with a phenanthroxazole-based compound and a phenanthrothiazole-based compound as a second host, an organic electroluminescent device with high efficiency, long life, and fast driving voltage can be introduced. In general, when a phosphorescent light-emitting material is substituted with other substituents such as a carbazole-based derivative with a high dihedral angle, the driving voltage increases due to the blocking of electronic current and the efficiency decreases. However, when using the light-emitting compound according to the present disclosure, an organic electroluminescent device with a relatively low driving voltage and excellent luminous efficiency, such as current efficiency and power efficiency, and high purity color, can be manufactured by improving the interface properties by improving the fast current injection characteristics and the intermolecular stacking and interaction. [Brief description of the drawings]

[0011] [Figure 1] 1 shows the current efficiency according to the luminance of the organic electroluminescent devices prepared in Comparative Example 2 and Device Example 1. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] The present disclosure will be described in detail below. 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.

[0013] The organic electroluminescent devices comprising the organic electroluminescent compounds represented by the above formulas 1, 2, or 3 are described in more detail as follows.

[0014] In the above formulas 1 and 2, X 1 -N=, -NR 7 represents -, -O- or -S-; Y 1 -N=, -NR 8 -, -O- or -S-, except that X 1 When represents -N=, Y 1 -NR 8 represents -, -O- or -S-; X 1 Ga-NR 7 When expressing -, Y 1 represents -N=, -O- or -S-. According to one embodiment of the present disclosure, X 1 and Y 1 One of them can be -N= and the other can be -NR 7 According to another embodiment of the present disclosure, X 1 and Y 1 One of X may be -N= and the other may be -O- or -S-. 1 and Y 1 Both cannot represent -O- or -S-, and X 1 and Y 1 When either of X can be -O-, the other cannot be -S-. For example, X 1 can be -N=, and Y 1 can be -O-, X 1 can be -O-, and Y 1 can be -N = or X 1 can be -S-, and Y 1can be -N=.

[0015] In the above formulas 1 and 2, R 1 represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl, preferably a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-25 membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-20 membered) heteroaryl, and may be, for example, unsubstituted phenyl, unsubstituted biphenyl, unsubstituted naphthyl, fluorenyl substituted with methyl, benzofluorenyl substituted with methyl, unsubstituted dibenzofuranyl, unsubstituted dibenzothiophenyl, spiro[fluorene-fluorenyl]yl, or spiro[fluorene-benzofluorenyl]yl.

[0016] In the above formulas 1 and 2, R 2 ~R 6are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 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 represents unsubstituted tri(C6-C30)arylsilyl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or may combine with adjacent substituents to form a substituted or unsubstituted (C3-C30)monocyclic or polycyclic, alicyclic, or aromatic ring, whose carbon atoms are replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur. Each of the substituents may be independently hydrogen, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (3-25 membered) heteroaryl, substituted or unsubstituted mono- or di-(C6-C25) arylamino, or may combine with adjacent substituents to form a substituted or unsubstituted (C3-C25) monocyclic or polycyclic, alicyclic, or aromatic ring, and these carbon atoms may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur, and more preferably each of the substituents may be independently hydrogen, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (C3-C25) monocyclic or polycyclic, alicyclic, or aromatic ring, and these carbon atoms may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur, or may combine with adjacent substituents to form a substituted or unsubstituted (C3-C25) monocyclic or polycyclic, alicyclic, or aromatic ring, the carbon atoms of which may be replaced with at least one heteroatom selected from nitrogen and oxygen, and the heteroaryl may contain at least one heteroatom selected from B, N, O, S, Si, and P. For example, R 5 and R 6may each independently be substituted or unsubstituted phenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, or substituted or unsubstituted benzofluorenyl.

[0017] In the above formulas 1 and 2, a represents 1 or 2, preferably 1; b and c each independently represent 1 or 2, preferably 1; d and e each independently represent an integer of 1 to 4, preferably 1 or 2.

[0018] In the above formulas 1 and 2, L 1 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene, preferably a single bond, or a substituted or unsubstituted (C6-C18) arylene, more preferably a single bond, or an unsubstituted (C6-C12) arylene, and can be, for example, a single bond, or an unsubstituted phenylene.

[0019] The compound represented by formula 1 or 2 is represented by any one of the following formulas 1-1 to 1-5: [ka]

[0020] In the above formulas 1-1 to 1-5, R 1 ~R 6 , L 1 and a to e are as defined in Formulas 1 and 2.

[0021] In the above formula 3, X 11 -N=, -NR 17 represents -, -O- or -S-; Y 11 -N=, -NR 18 -, -O- or -S-, except that X 11 When represents -N=, Y 11 -NR 18 represents -, -O- or -S-; X 11 Ga-NR17 When expressing -, Y 11 represents -N=, -O- or -S-. According to one embodiment of the present disclosure, X 11 and Y 11 One of them can be -N= and the other can be -NR 17 According to another embodiment of the present disclosure, X 11 and Y 11 One of X may be -N= and the other may be -O- or -S-. 11 and Y 11 Both cannot represent -O- or -S-, and X 1 and Y 1 When either one of can be -O-, the other cannot be -S-.

[0022] In the above formula 3, R 11 represents a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (3-30 membered) heteroaryl, preferably a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-25 membered) heteroaryl, more preferably a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-20 membered) heteroaryl, and may be, for example, unsubstituted phenyl, unsubstituted biphenyl, unsubstituted naphthyl, fluorenyl substituted with methyl, substituted or unsubstituted carbazolyl, benzofluorenyl substituted with methyl, unsubstituted dibenzofuranyl, unsubstituted dibenzothiophenyl, unsubstituted benzonaphthofuranyl, spiro[fluorene-fluorenyl]yl, or spiro[fluorene-benzofluorenyl]yl.

[0023] In the above formula 3, R 12 ~R 18are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 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-(C6-C30)arylamino, or substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, or may combine with adjacent substituents to form a substituted or unsubstituted (C3-C30)monocyclic or polycyclic, alicyclic, or aromatic ring, whose carbon atoms are replaced by at least one heteroatom selected from nitrogen, oxygen, and sulfur. Each of the substituents may be independently hydrogen, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (3-25 membered) heteroaryl, substituted or unsubstituted mono- or di-(C6-C25) arylamino, or may combine with adjacent substituents to form a substituted or unsubstituted (C3-C25) monocyclic or polycyclic, alicyclic, or aromatic ring, and these carbon atoms may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur, and more preferably each of the substituents may be independently hydrogen, substituted or unsubstituted (C6-C25) aryl, substituted or unsubstituted (C3-C25) aryl, alicyclic, or aromatic ring. represents hydrogen, substituted or unsubstituted (C6-C20) aryl, substituted or unsubstituted (5-25 membered) heteroaryl, substituted or unsubstituted di(C6-C18) arylamino, or can combine with adjacent substituents to form a substituted or unsubstituted (C3-C25) monocyclic or polycyclic, alicyclic, or aromatic ring, the carbon atoms of which may be replaced with at least one heteroatom selected from nitrogen and sulfur, and the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P. For example, R 15 and R 16may each independently be selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted benzocarbazole, and substituted or unsubstituted benzonaphthothiophene.

[0024] In the above formula 3, a' represents 1 or 2, preferably 1; b' and c' each independently represent 1 or 2, preferably 1; d' represents an integer of 1 to 4, preferably 1 or 2.

[0025] In the above formula 3, X represents N or CH.

[0026] In the above formula 3, L 2 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene, preferably a single bond, a substituted or unsubstituted (C6-C18) arylene, more preferably a single bond or an unsubstituted (C6-C12) arylene, and can be, for example, a single bond or unsubstituted phenylene.

[0027] The compound represented by formula 3 is represented by any one of the following formulas 3-1 to 3-6: [ka]

[0028] In the above formulas 3-1 to 3-6, R 11 ~R 18 , L 2 , X and a′ to d′ are as defined in Formula 3.

[0029] In this specification, "(C1-C30) alkyl" is intended to mean straight-chain or branched alkyl having 1 to 30 carbon atoms constituting the chain (the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10), and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. "(C2-C30) alkenyl" is intended to mean straight-chain or branched alkenyl having 2 to 30 carbon atoms constituting the chain (the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10), and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. "(C2-C30)alkynyl" is intended to mean straight-chain or branched alkynyl having 2-30 carbon atoms (preferably 2-20, more preferably 2-10 carbon atoms) constituting the chain, including ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, and the like. "(C3-C30)cycloalkyl" is intended to mean a monocyclic or polycyclic hydrocarbon having 3-30 ring skeletal carbon atoms (preferably 3-20, more preferably 3-7 carbon atoms), including cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. "(3-7 membered)heterocycloalkyl" is intended to mean a cycloalkyl having 3-7, preferably 5-7, ring skeletal atoms containing at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably O, S, and N, including tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, and the like. "(C6-C60)aryl(ene)" is intended to mean a monocyclic or fused ring group derived from an aromatic hydrocarbon having 6 to 60 ring carbon atoms (preferably 6 to 30, more preferably 6 to 20, ring carbon atoms), which may be partially saturated and may contain a spiro structure.The above aryl may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylethylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc. The term "(3-30 membered) heteroaryl (heteroarylene)" is intended to mean an aryl having 3-30 ring skeletal atoms and containing at least one, preferably 1-4 heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The above heteroaryl may be a monocyclic ring or a fused ring fused with at least one benzene ring, may be partially saturated, and may be formed by binding at least one heteroaryl or aryl group to a heteroaryl group via a single bond. Heteroaryl includes monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and the like, and condensed ring heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, naphthyridyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, and the like.The term "nitrogen-containing (5-30 membered) heteroaryl" is intended to mean an aryl group having at least one N and 5 to 30 ring skeletal atoms (the number of ring skeletal atoms is preferably 5 to 20, more preferably 5 to 15), preferably having 1 to 4 heteroatoms, which may be a monocyclic ring or a fused ring fused with at least one benzene ring, which may be partially saturated, and which may be formed by bonding at least one heteroaryl or aryl group to a heteroaryl group by a single bond, including monocyclic ring-type heteroaryls such as pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and the like, and fused ring-type heteroaryls such as benzimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, and the like. “Halogen” includes F, Cl, Br, and I.

[0030] Furthermore, the term "substituted" in the phrase "substituted or unsubstituted" means that a hydrogen atom in a particular functional group is replaced with another atom or another functional group (i.e., a substituent). 1 ~R 8 , R 11 ~R 18 , L 1 , and L 2The substituents of the substituted alkyl, substituted alkoxy, substituted cycloalkyl, substituted aryl(ene), substituted heteroaryl(ene), substituted trialkylsilyl, substituted triarylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted mono- or di-alkylamino, substituted mono- or di-arylamino, substituted alkylarylamino, and substituted monocyclic or polycyclic, alicyclic or aromatic ring in the formula (I) are each independently deuterium; halogen; cyano; carboxyl; nitro; hydroxy; (C1-C30) alkyl; halo(C1-C 30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (3-7 membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (C6-C30) aryl- or di(C6-C30) arylamino substituted or unsubstituted (3-30 membered) heteroaryl; cyano-, (3-30 membered) heteroaryl-, or tri(C6-C30) arylsilyl substituted or unsubstituted (C6-C30) aryl; tri(C1-C3 0)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;(C1-C30)alkyl(C6-C30)arylamino;(C1-C30)alkylcarbonyl;(C1-C30)alkoxycarbonyl;(C6-C30)arylcarbonyl;Di(C6-C30)arylboronyl;Di(C1-C30)alkyl at least one selected from the group consisting of arylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)aryl(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl, preferably each independently being (C1-C20)alkyl; (C6-C18)aryl-substituted or unsubstituted (3-25 membered)heteroaryl; cyano-, tri(C6-C18)arylsilyl-, or (3-20 membered)heteroaryl-, substituted or unsubstituted (C6-C20)aryl; tri(C6-C18)arylsilyl;and at least one selected from the group consisting of (C1-C20) alkyl and (C6-C20) aryl;

[0031] The compounds represented by formula 1 or 2 may more specifically be represented by, but are not limited to, the following compounds: [ka] [ka]

[0032] The compound represented by formula 3 may more specifically be represented by, but is not limited to, the following compounds: [ka] [ka] [ka] [ka]

[0033] The organic electroluminescent device according to the present disclosure comprises an anode, a cathode, and at least one organic layer between the anode and the cathode. The organic layer comprises an emitting layer comprising a host and a phosphorescent dopant. The host comprises a plurality of host compounds, at least a first host compound of the plurality of host compounds is represented by the above formula 1 or 2, and a second host compound is represented by the above formula 3.

[0034] In the present disclosure, the light-emitting layer is the layer that emits light, and can be a single layer, or can be a multi-layer in which two or more layers are stacked. In the light-emitting layer, the doping concentration of the dopant compound based on the host compound is preferably less than 20% by weight.

[0035] The organic layer may include an emitting layer, and may further include at least one layer selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer.

[0036] In the organic electroluminescent device of the present disclosure, the weight ratio of the first host compound to the second host compound ranges from 1:99 to 99:1.

[0037] The dopant that is included in the organic electroluminescent device according to the present disclosure is preferably at least one phosphorescent dopant.The phosphorescent dopant material that is included in the organic electroluminescent device according to the present invention is not particularly limited, but can be preferably selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) metallized complex compound, more preferably selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) ortho-metallized complex compound, and even more preferably can be ortho-metallized iridium complex compound.

[0038] Dopants included in the organic electroluminescent devices of the present disclosure can include, but are not limited to, compounds represented by the following formula 101: [ka] (wherein L is structure 1 or 2: [ka] Selected from R 100 ~R 103 each independently represents hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, cyano, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C1-C30) alkoxy; or R 100 ~R 103may combine with adjacent substituents to form a substituted or unsubstituted fused ring, such as substituted or unsubstituted quinoline, substituted or unsubstituted benzofuropyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuroquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline; R 104 ~R 107 each independently represents hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; or R 104 ~R 107 may combine with adjacent substituents to form a substituted or unsubstituted fused ring, such as substituted or unsubstituted naphthyl, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine, or substituted or unsubstituted benzothienopyridine; R 201 ~R 211 each independently represents hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) aryl; or R 201 ~R 211 may combine with an adjacent substituent to form a substituted or unsubstituted fused ring; and n represents an integer of 1 to 3.

[0039] Specific examples of dopant materials include: [ka] [ka] [ka] [ka]

[0040] The organic electroluminescent device of the present disclosure may further comprise at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds in the organic layer.

[0041] Furthermore, in the organic electroluminescent device of the present disclosure, the organic layer may further comprise at least one metal selected from the group consisting of Group 1 metals, Group 2 metals, Group 4 transition metals, Group 5 transition metals, lanthanides of the d-transition elements of the periodic table, and organometallics, and at least one complex compound containing the aforementioned metals.

[0042] In the organic electroluminescent device of the present disclosure, it may be preferable to dispose at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter, "surface layer") on the inner surface of one or both electrodes. Specifically, it is preferable to dispose a silicon or aluminum chalcogenide (including oxide) layer on the anode surface of the electroluminescent medium layer, and it is preferable to dispose a metal halide or metal oxide layer on the cathode surface of the electroluminescent medium layer. Such a surface layer can provide operational stability to the organic electroluminescent device. Preferably, the aforementioned chalcogenide is SiO X (1≦X≦2), AlO X (1≦X≦1.5), SiON, SiAlON, etc., and the aforementioned metal halides include LiF, MgF 2 , CaF 2 , rare earth metal fluorides, etc., and the aforementioned metal oxides include Cs 2 O, Li 2 Contains O, MgO, SrO, BaO, CaO, etc.

[0043] Between the anode and the light-emitting layer, a layer selected from a hole injection layer, a hole transport layer, or an electron blocking layer, or a combination thereof, may be used. The hole injection layer may be formed of multiple layers to lower 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 in each layer. Also, the hole transport layer or the electron blocking layer may be formed of multiple layers.

[0044] Between the light-emitting layer and the cathode, a layer selected from an electron buffer layer, a hole blocking layer, an electron transport layer, or an electron injection layer, or a combination thereof, may be used. The electron buffer layer may be formed of multiple layers to control the injection of electrons and to enhance the interface properties between the light-emitting layer and the electron injection layer. Two compounds may be used simultaneously in each layer. Also, the hole blocking layer or the electron transport layer may be formed of multiple layers, and each layer may contain two or more compounds.

[0045] Furthermore, in the organic electroluminescent device of the present disclosure, the mixed region of the electron transport compound and the reductive dopant or the mixed region of the hole transport compound and the oxidative dopant is preferably disposed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anion, so that the injection and transport of electrons from the mixed region to the electroluminescent medium is easier. Furthermore, the hole transport compound is oxidized to cation, so that the injection and transport of holes from the mixed region to the electroluminescent medium is easier. Preferably, the oxidative dopant comprises various Lewis acids and acceptor compounds, and the reductive dopant comprises alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof. The reductive dopant layer can be used as a charge generating layer to prepare an organic electroluminescent device having two or more light-emitting layers and emitting white light.

[0046] Dry deposition methods such as vacuum deposition, sputtering, plasma and ion plating, or wet deposition methods such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating and flow coating can be used to form each layer of the organic electroluminescent device of the present disclosure.

[0047] When using a wet film-forming method, a thin film can be formed by dissolving or diffusing the material forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent as long as the material forming each layer can be dissolved or diffused therein and there is no problem with film-forming ability.

[0048] Additionally, the first and second host compounds of the present disclosure may be co-vaporized or mixed-vaporized.

[0049] By using the organic electroluminescent devices of the present disclosure, display systems or lighting systems can be manufactured.

[0050] Hereinafter, the organic electroluminescent compound according to the present disclosure, the preparation method thereof and the luminescent properties of the organic electroluminescent device containing the same will be described in detail with respect to the representative compound of the present disclosure in order to understand the present disclosure in detail.

[0051] Example 1: Preparation of compound H1-1 [ka] Compound 1-1 (4 g, 12 mmol), bis(biphenyl-4-yl)[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaboran-2-yl)phenyl]amine (6.8 g, 13 mmol), palladium(II) acetate (0.3 g, 1 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.9 g, 2 mmol), cesium carbonate (11.5 g, 35 mmol), 60 mL of o-xylene, 15 mL of ethanol, and 15 mL of distilled water were added to a reactor and refluxed for 3 hours. After completion of the reaction, the organic layer was washed with distilled water and extracted with ethyl acetate. The organic layer was then dried over magnesium sulfate. The solvent was removed by rotary evaporator, and the resulting product was purified by column chromatography to obtain compound H1-1 (2.2 g, yield: 27%).

[0052] [Table 1]

[0053] Example 2: Preparation of Compound H1-42 [ka] Compound 2-1 (4.8 g, 11.34 mmol), N-(4-bromophenyl)-N-phenyl-[1,1'-biphenyl]-4-amine (5 g, 12.47 mmol), tetrakis(triphenylphosphine)palladium (0.4 g, 0.34 mmol), sodium carbonate (3.0 g, 28.35 mmol), 57 mL of toluene, 14 mL of ethanol, and 14 mL of distilled water were added to a reactor and stirred at 120°C for 4 hours. After the reaction was completed, methanol was added dropwise to the mixture, and the obtained solid was filtered. The obtained solid was purified and recrystallized by column chromatography to obtain compound H1-42 (1.4 g, yield: 20.0%).

[0054] [Table 2]

[0055] Example 3: Preparation of Compound H1-27 [ka] Compound 3-1 (4.5 g, 16.09 mmol), 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (5.5 g, 19.31 mmol), palladium(II) acetate (0.2 g, 0.80 mmol), tri-t-butylphosphine (0.8 mL, 1.60 mmol), sodium tert-butoxide (2.3 g, 24.14 mmol), and 80 mL of o-xylene were added to a reactor and refluxed at 120° C. for 2 hours. After completion of the reaction, the mixture was cooled to room temperature, and the obtained solid was filtered and washed with ethyl acetate. The filtrate was distilled under reduced pressure, and the obtained solid was purified and recrystallized by column chromatography to obtain compound H1-27 (2.4 g, yield: 28%).

[0056] [Table 3]

[0057] Example 4: Preparation of compound H2-1 [ka] Compound 2-1 (10 g, 23.7 mmol), 2-chloro-4,6-diphenyltriazine (CAS: 3842-55-5, 5.8 g, 21.6 mmol), tetrakis(triphenylphosphine)palladium (1.2 g, 1.0 mmol), potassium carbonate (7.5 g, 59 mmol), 90 mL of toluene, 30 mL of ethanol, and 30 mL of distilled water were added to a reactor and stirred at 120° C. for 4 hours. After the reaction was completed, methanol was added dropwise to the mixture, and the resulting solid was filtered. The resulting solid was purified and recrystallized by column chromatography to obtain compound H2-1 (5.7 g, yield: 50%).

[0058] [Table 4]

[0059] Example 5: Preparation of compound H2-2 [ka] Compound 2-1 (3.48 g, 8.3 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (CAS: 1472062-94-4, 3.53 g, 9.1 mmol), tetrakis(triphenylphosphine)palladium (0.48 g, 0.41 mmol), sodium carbonate (2.2 g, 20.7 mmol), 28 mL of toluene, 7 mL of ethanol, and 7 mL of distilled water were added to a reactor and stirred at 120°C for 5 hours. After the reaction was completed, methanol was added dropwise to the mixture, and the obtained solid was filtered. The obtained solid was purified and recrystallized by column chromatography to obtain compound H2-2 (3.7 g, yield: 74%).

[0060] [Table 5]

[0061] The LUMO (Lowest Unoccupied Molecular Orbital) energies, HOMO (Highest Occupied Molecular Orbital) energies, and triplet energies of compounds H1-1 and H1-27 synthesized in Examples 1 and 3 above were calculated using density functional theory (DFT) at the B3LYP / 6-31g(d) level and are shown in Table 1 below.

[0062] In principle, the LUMO and HOMO energy values ​​measured as described above have negative values; however, for convenience, they are expressed as absolute values. Furthermore, when comparing the magnitudes of the LUMO / HOMO energy values, one compares their absolute values.

[0063] [Table 6]

[0064] With reference to Table 1 above, the device characteristics of the first host compound according to one embodiment, that is, the compound H1-1 represented by formula 1 and the compound H1-27 represented by formula 2, can be compared and predicted. Specifically, the compound H1-27 has a HOMO energy value similar to that of the compound H1-1, and a LUMO energy value lower than that of the compound H1-1. Therefore, it is expected that the electron carriers are sufficiently confined when the compound H1-27 is used. Furthermore, it can be confirmed that when the host compounds H1-1 and H1-27 are combined with a host having strong electron current characteristics, the energy values ​​are such that there is no problem with exciplex formation. Furthermore, the triplet energy values ​​of the compounds H1-1 and H1-27 are 2.4 eV and 2.5 eV, respectively, which are sufficient to block the triplet energy of the dopant. That is, when the compound H1-1 or H1-27 is used as the first host compound according to one embodiment, it can be expected that the device containing one of them will show similar device characteristics to the device containing the other.

[0065] Therefore, in the following device examples, organic electroluminescent devices are fabricated by using only the compounds H1-1 and H1-42 represented by Formula 1 as representative first host compounds, and the properties of the devices are described.

[0066] Comparative Example 1: Preparation of a red-emitting organic electroluminescent device not according to the present disclosure An OLED device not according to the present disclosure was fabricated. First, a transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) of an OLED glass substrate (Geomatec Co., Ltd., Japan) was ultrasonically cleaned in acetone and isopropyl alcohol in sequence, and then stored in isopropanol. Next, the ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus. Compound HI-1 was introduced into the cell of the vacuum deposition apparatus, and then the pressure in the chamber of the apparatus was increased to 10 -7Torr. Then, a current was applied to the cell to evaporate the introduced material, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate. Next, compound HI-2 was introduced into another cell of the vacuum deposition apparatus, and a current was applied to the cell to evaporate the introduced material, thereby forming a second hole injection layer having a thickness of 5 nm on the first hole injection layer. Next, compound HT-1 was introduced into another cell of the vacuum deposition apparatus. Then, a current was applied to the cell to evaporate the introduced material, thereby forming a first hole transport layer having a thickness of 10 nm on the second hole injection layer. Next, compound HT-2 was introduced into another cell of the vacuum deposition apparatus, and a current was applied to the cell to evaporate the introduced material, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, the light-emitting layer was evaporated as follows. Compound H1-1 was introduced as a host into one cell of a vacuum evaporation apparatus, and compound D-39 was introduced as a dopant into another cell of the apparatus. The two materials were evaporated at different rates, and the dopant was evaporated with a doping amount of 3 wt% based on the total amount of the host and dopant to form a 40 nm thick light-emitting layer on the second hole transport layer. Then, compounds ETL-1 and EIL-1 were evaporated on the light-emitting layer as electron transport materials in a weight ratio of 50:50 to form a 35 nm thick electron transport layer. Then, compound EIL-1 was evaporated on the electron transport layer as an electron injection layer to a thickness of 2 nm, and then an 80 nm thick Al cathode was evaporated on the electron injection layer in another vacuum evaporation apparatus. In this way, an OLED device was fabricated. All materials used to fabricate the OLED device were evaporated in a 10 -6 It was purified by vacuum sublimation at torr.

[0067] Comparative Example 2: Preparation of a red-emitting organic electroluminescent device not according to the present disclosure An OLED device was fabricated in the same manner as in Comparative Example 1, except that compound H2-2 was used instead of H1-1 as the light-emitting material.

[0068] Comparative Example 3: Preparation of a red-emitting organic electroluminescent device not according to the present disclosure An OLED device was fabricated in the same manner as in Comparative Example 1, except that compound H2-1 was used instead of H1-1 as the light-emitting material.

[0069] Device Examples 1-3: Fabrication of Red-Emitting Organic Electroluminescent Devices According to the Present Disclosure In device examples 1 to 3, the OLED devices were fabricated in the same manner as in comparative example 1, except that the first host compound and the second host compound listed in Table 2 below were introduced into one cell of a vacuum deposition apparatus as the host, and compound D-39 was introduced into another cell of the apparatus as the dopant. The two host materials were evaporated simultaneously in the same ratio of 1:1, and the dopant was evaporated at different rates with a doping amount of 3 wt % based on the total weight of the host and the dopant to form a 40 nm thick light-emitting layer.

[0070] The driving voltage, luminous efficiency, and CIE color coordinates at a luminance of 1,000 nits of the organic electroluminescent devices of Comparative Example 1 to 3 and Device Example 1 to 3 prepared as above, and the time taken for the luminescence to decrease from 100% to 90% at a luminance of 5,000 nits (lifetime; T90) are shown in Table 2 below. Furthermore, the current efficiency according to the luminance of the organic electroluminescent devices prepared in Comparative Example 2 and Device Example 1 is shown in FIG.

[0071] [Table 7]

[0072] From the above device examples 1 to 3, it was confirmed that the combination of compounds of the present disclosure can significantly improve efficiency and life characteristics while maintaining a driving voltage similar to that of the comparative example. Specifically, referring to FIG. 1, the combination of the emitting layer as an organic electroluminescent device according to one embodiment shows a significant effect in improving roll-off compared to the comparative example, which is a combination of a single emitting layer.

[0073] The compounds used in the comparative examples and device examples are shown in Table 3 below.

[0074]

Table 8

Claims

1. A plurality of host materials including at least one first host compound and at least one second host compound, wherein the first host compound has the following formula 1-3: 【Chemistry 1】 (In the formula, R 1 represents a deuterium substituted or unsubstituted (C6-C30) aryl; R 2 ~R 4 each independently represents hydrogen, deuterium, halogen, cyano, unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted mono- or di-(C6-C30) arylamino; R 5 and R 6 each independently represents a substituted or unsubstituted (C6-C30) aryl, a deuterated or unsubstituted dibenzofuranyl, a deuterated or unsubstituted dibenzothiophenyl, or a deuterated or unsubstituted carbazolyl; L 1 represents a single bond or a deuterium-substituted or unsubstituted (C6-C30) arylene; a represents 1, b and c each independently represent 1 or 2, and d represents an integer from 1 to 4. and the second host compound is represented by the following formula 3-1: 【Chemistry 2】 (In the formula, X represents N or CH; R 11 represents a substituted or unsubstituted (C6-C30) aryl or a substituted or unsubstituted (3-30 membered) heteroaryl; R 12 ~R 16 each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 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 may combine with adjacent substituents to form a substituted or unsubstituted (C3-C30) monocyclic or polycyclic, alicyclic or aromatic ring, whose carbon atoms may be replaced by at least one heteroatom selected from nitrogen, oxygen, and sulfur; L 2 represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (3-30 membered) heteroarylene; a' represents 1, b' and c' each independently represent 1 or 2, and d' represents an integer from 1 to 4, the heteroaryl(ene) contains at least one heteroatom selected from B, N, O, S, Si, and P; R in the formula 3-1 12 ~R 16 and L 2 wherein the substituents of the substituted aryl(ene), the substituted heteroaryl(ene) and the substituted monocyclic or polycyclic aromatic ring are each independently selected from the group consisting of 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, (3-7 membered) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, (C6-C30) aryl-substituted or unsubstituted (3-30 membered) heteroaryl, cyano-, (3-30 membered) heteroaryl- or tri(C6-C30) ) arylsilyl--at least one selected from the group consisting of substituted or unsubstituted (C6-C30)aryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl). A plurality of host materials, represented by:

2. R 2 ~R 6 and the substituted alkyl, substituted alkoxy, substituted cycloalkyl, substituted aryl(ene), substituted heteroaryl(ene), substituted trialkylsilyl, substituted triarylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted mono- or di-alkylamino, substituted mono- or di-arylamino, substituted alkylarylamino, and substituted monocyclic or polycyclic, alicyclic, or aromatic ring substituents in R 11. are each independently 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; (3-7 membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (C6-C30)aryl- or di(C6-C30)aryla amino-substituted or unsubstituted (3-30 membered)heteroaryl; cyano-, (3-30 membered)heteroaryl- or tri(C6-C30)arylsilyl-substituted or unsubstituted (C6-C30)aryl; 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)aryl and at least one selected from the group consisting of: (C1-C30)alkylamino; (C6-C30)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl, R 12 ~R 16 The substituents of the substituted alkyl, substituted alkoxy, substituted cycloalkyl, substituted trialkylsilyl, substituted triarylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, and substituted monocyclic, polycyclic, and alicyclic ring are each independently selected from the group consisting of deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30) alkyl, halo(C1-C30) alkyl, halo(C1-C30) alkyl, and halo(C1-C30) alkyl. )alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (3-7 membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (C6-C30)aryl- or di(C6-C30)arylamino-substituted or unsubstituted (3-30 membered)heteroaryl; cyano-, (3-30 membered)heteroaryl- or Tri(C6-C30)arylsilyl-substituted or unsubstituted (C6-C30)aryl; 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; (C1-C30)alkyl(C6-C30)arylsilyl at least one selected from the group consisting of arylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; di(C6-C30) arylboronyl; di(C1-C30) alkylboronyl; (C1-C30) alkyl(C6-C30) arylboronyl; (C6-C30) ar(C1-C30) alkyl; and (C1-C30) alkyl(C6-C30) aryl, and R 12 ~R 16 and L 2 wherein the substituents of the substituted aryl(ene), the substituted heteroaryl(ene), and the substituted monocyclic or polycyclic aromatic ring are each independently selected from the group consisting of 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, (3-7 membered)heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (C6-C30)aryl-substituted or unsubstituted (3-30 membered)heteroaryl, cyano-, (3-30 membered)heteroaryl-, or tri(C6-C30)arylsilyl.

2. The host material of claim 1, wherein the at least one is selected from the group consisting of aryl-substituted or unsubstituted (C6-C30)aryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronyl; di(C1-C30)alkylboronyl; (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.

3. The compound represented by formula 1-3 is 【Chemistry 3】 The host material of claim 1 selected from the group consisting of:

4. The compound represented by formula 3-1 is 【Chemistry 4】 The host material of claim 1 selected from the group consisting of:

5. 13. An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, the light-emitting layer comprising a host and a phosphorescent dopant, the host comprising the host material of claim 1.

Citation Information

Patent Citations

  • Organic electroluminescence element

    JP2007110102A

  • Organic electroluminescence light emitting device

    JP2007200938A

  • Organic electroluminescence element

    JP2007221097A

  • Organic electroluminescent compound and organic electroluminescent device containing the same

    JP2018533200A

  • Organic electroluminescent compounds and organic electroluminescent device comprising the same

    WO2017030283A1

Cited By

  • Host materials and organic electroluminescent device including the same

    JP2025060731A