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KR-102961379-B1 - A PLURALITY OF HOST MATERIALS AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME

KR102961379B1KR 102961379 B1KR102961379 B1KR 102961379B1KR-102961379-B1

Abstract

The present invention relates to multiple types of host materials and organic electroluminescent devices comprising the same. By including distinct compounds represented by the following complementary chemical formulas 1 and 2 in the light-emitting layer, the present invention can provide multiple types of host materials having a composition favorable for thermal degradation by having a low deposition temperature while improving the hole and electronic characteristics of HOMO and LUMO. Furthermore, by including multiple types of host materials according to the present invention, an organic electroluminescent device having low driving voltage, high luminous efficiency, and/or long lifespan characteristics can be provided. [Chemical Formula 1] [Chemical Formula 2] The definitions of the substituents in the above chemical formulas 1 and 2 are as defined in the specification.

Inventors

  • 김빛나리
  • 이수현
  • 정소영
  • 박효순
  • 한태준
  • 조영준
  • 조상희

Assignees

  • 듀폰스페셜티머터리얼스코리아 유한회사

Dates

Publication Date
20260511
Application Date
20240610
Priority Date
20170922

Claims (7)

  1. A plurality of host materials comprising a first host material comprising a compound represented by the following chemical formula 1, and a second host material comprising a compound represented by the following chemical formula 2: [Chemical Formula 1] In the above chemical formula 1, L1 and L2 are each independently a single-bonded, substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3-30)heteroarylene; Ar 1 and Ar 2 are each independently a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3-30)heteroaryl, an amino, 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; A and B are each a benzene ring or a naphthalene ring, provided that at least one of A and B is a naphthalene ring; R1 to R3 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (3-30)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 It is a mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; each of R1 to R3 may be connected to form a substituted or unsubstituted (3-30) single or polycyclic ring; a is an integer from 1 to 4 when A is a benzene ring, and an integer from 1 to 6 when A is a naphthalene ring; b is 1 or 2 if B is a benzene ring, and an integer from 1 to 4 if B is a naphthalene ring; c is an integer from 1 to 4; If a to c are each integers of 2 or more, each R1 to R3 may be the same or different from each other; [Chemical Formula 2] In the above chemical formula 2, HAr is a substituted or unsubstituted, nitrogen-containing (3-10-membered) heteroaryl; L3 is a single bond, or a substituted or unsubstituted (C6-C30)arylene; Ar 3 is a substituted or unsubstituted (C6-C30)aryl; However, L3 - Ar3 does not contain N; d is an integer from 1 to 3, and if d is an integer greater than or equal to 2, each (L 3 -Ar 3 ) may be the same or different from each other.
  2. In claim 1, a plurality of host materials, wherein the compound represented by Chemical Formula 1 is represented by one or more of the following Chemical Formulas 3 and 4: [Chemical Formula 3] [Chemical Formula 4] In the above chemical formulas 3 and 4, L1 , L2 , Ar1 , Ar2 , R1 to R3 , and a to c are as defined in claim 1.
  3. In claim 1, a plurality of host materials, wherein the compound represented by Chemical Formula 2 is represented by one or more of the following Chemical Formulas 5 and 6: [Chemical Formula 5] [Chemical Formula 6] In the above chemical formulas 5 and 6, X 1 to X 6 are each independently CR 4 or N, and at least one of X 1 to X 4 is N; R4 is hydrogen, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C2-C30)alkenyl, or a substituted or unsubstituted (C1-30)alkyl; two adjacent R4s may be connected to each other to form a substituted or unsubstituted (3-30) single or polycyclic ring; L3 , Ar3 , and d are as defined in paragraph 1.
  4. In claim 1 , the aryl(len), substituted heteroaryl(len), substituted mono- or di - alkylamino , substituted mono- or di- arylamino , substituted alkylarylamino, substituted alkyl, substituted alkenyl, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, or substituted single-ring or polycyclic ring substituents are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxy, (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl, (C3-C30)cycloalkenyl, (3-7)heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (5-30)heteroaryl, (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)arylamino, (C1-C30)alkylcarbonyl, A plurality of host materials, one or more selected from the group consisting of (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.
  5. A plurality of host materials, wherein the compound represented by Chemical Formula 1 is selected from the group consisting of the following compounds.
  6. A plurality of host materials, wherein the compound represented by Chemical Formula 2 is selected from the group consisting of the following compounds.
  7. 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 of the light-emitting layers comprises a plurality of host materials as described in claim 1.

Description

A plurality of host materials and an organic electroluminescent device comprising the same The present invention relates to a plurality of host materials and an organic electroluminescent device comprising the same. Since Tang et al. at Eastman Kodak first developed a TPD/Alq3 bilayer small molecule green organic electroluminescent device (OLED) consisting of an emissive layer and a charge transport layer in 1987, research on organic electroluminescent devices has progressed rapidly and has now reached commercialization. An organic electroluminescent device (OLED) is a device that converts electrical energy into light by applying electricity to an organic light-emitting material, and typically has a structure including an anode and a cathode and an organic layer between them. The organic layer of an organic electroluminescent device may include a hole injection layer, a hole transport layer, a hole assist layer, a light assist layer, an electron blocking layer, an emissive layer, an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. The materials used in the above organic layer can be classified according to their function into hole injection materials, hole transport materials, hole assist materials, light emission assist materials, electron blocking materials, light emission materials (including host and dopant materials), electron buffer materials, hole blocking materials, electron transport materials, electron injection materials, etc. The light-emitting material of an organic electroluminescent device is the most critical factor determining the device's luminous efficiency; therefore, the light-emitting material must possess high quantum efficiency and high electron and hole mobilities, while the formed light-emitting layer must be uniform and stable. These materials are classified into blue, green, or red light-emitting materials based on their emission color, with additional yellow or orange light-emitting materials also available. Furthermore, light-emitting materials can be functionally categorized into host materials and dopant materials. Recently, the development of high-efficiency and long-life organic electroluminescent devices has emerged as an urgent task. Considering the EL characteristics required for medium to large-sized OLED panels, there is an urgent need to develop materials that are significantly superior to existing light-emitting materials. To this end, the desirable characteristics of the solid-state solvent and the host material, which acts as an energy carrier, include high purity and an appropriate molecular weight to enable vacuum deposition. In addition, thermal stability must be ensured by having a high glass transition temperature and thermal decomposition temperature, high electrochemical stability is required for long lifespan, it should be easy to form an amorphous thin film, and it is desirable to have good adhesion to materials of adjacent layers while not allowing interlayer migration. Korean Patent Registration Publication No. 1311934 and Korean Patent Publication No. 2015-124902 disclose an organic electroluminescent device comprising an indolocarbazole compound as one of a plurality of host compounds, but further development is still required to improve the performance of the OLED. The present invention is described in more detail below, but this is for illustrative purposes only and should not be interpreted as limiting the scope of the present invention. In the present invention, "organic electroluminescent material" refers to a material that can be used in an organic electroluminescent device, may include one or more compounds, and may be included in any layer constituting the organic electroluminescent device as needed. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light-emitting assist material, an electron blocking material, a light-emitting material (including a host material and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc. In this document, "multiple types of organic electroluminescent materials" refers to organic electroluminescent materials comprising a combination of two or more compounds that may be included in any layer constituting an organic electroluminescent device, and may refer to both the materials before (e.g., before deposition) and after (e.g., after deposition) inclusion in the organic electroluminescent device. For example, the multiple types of organic electroluminescent materials may be a combination of two or more compounds that may be included in one or more layers among a hole injection layer, a hole transport layer, a hole assist layer, a light-emitting assist layer, an electron blocking layer, a light-emitting layer, an electron buffer layer, a hole blocking layer, an electron transport l