Polymer for organic electroluminescent elements and organic electroluminescent element

A light-emitting element and organic electric field technology, which is applied in the field of polymers for organic electric field light-emitting elements, can solve problems such as insufficient materials, low molecular weight compounds, and difficult lamination and film formation, and achieve high performance, high luminous efficiency, and high driving stability. Effect

Pending Publication Date: 2021-11-09
NIPPON STEEL CHEM &MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

High luminous efficiency can be expected for luminescent materials using the TADF mechanism, but the compounds described in the literature are all low molecular weight, and it is difficult to perform lamination and film formation, etc., and they are not sufficient as materials for wet processes.

Method used

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  • Polymer for organic electroluminescent elements and organic electroluminescent element
  • Polymer for organic electroluminescent elements and organic electroluminescent element
  • Polymer for organic electroluminescent elements and organic electroluminescent element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0241] Polymer P-4 was synthesized via Intermediate A, Intermediate B, Intermediate C, Polymerized Intermediate A, Polymerized Intermediate B.

[0242] (Synthesis of Intermediate A)

[0243] [chemical 20]

[0244]

[0245] Under a nitrogen atmosphere, 5.13 g (20.0 mmol) of 5,12-dihydroindolo[3,2-a]carbazole, 2-(2-fluorophenyl)-4,6-diphenyl-1 , 7.21 g (22.0 mmol) of 3,5-triazine, 32.61 g (100.1 mmol) of cesium carbonate, and 100 ml of N-N-dimethylacetamide (dehydrated) were stirred. Then, it heated to 140 degreeC, and stirred for 24 hours. After cooling the reaction solution to room temperature, inorganic substances were separated by filtration. The filtrate was dried under reduced pressure and purified by column chromatography to obtain 8.1 g (14.4 mmol, yield 71.8%) of intermediate A as a pale yellow powder.

[0246] (Synthesis of Intermediate B)

[0247] [chem 21]

[0248]

[0249] Under nitrogen atmosphere, add intermediate A 2.00g (3.5mmol), 3,5-dibromoiodobenzen...

Embodiment 2

[0262] Polymer P-13 was synthesized via Intermediate D, Intermediate E, Intermediate F, Intermediate G, Intermediate H and Polymerized Intermediate C, Polymerized Intermediate D.

[0263] (Synthesis of Intermediate D)

[0264] [chem 24]

[0265]

[0266] Under nitrogen atmosphere, add 9-phenyl-9H, 9'H-3,3'-bicarbazole 8.15g (20.0mmol), 3,5-dibromoiodobenzene 9.38g (25.9mmol), copper iodide 0.11 g (0.6 mmol), 21.17 g (99.8 mmol) of tripotassium phosphate, 0.91 g (8.0 mmol) of trans-1,2-cyclohexanediamine, and 80 ml of 1,4-dioxane were stirred. Then, it heated to 120 degreeC, and stirred for 24 hours. After cooling the reaction solution to room temperature, inorganic substances were separated by filtration. The filtrate was dried under reduced pressure and purified by column chromatography to obtain 9.60 g (14.9 mmol, yield 74.9%) of intermediate D as a light yellow powder.

[0267] (Synthesis of Intermediate E)

[0268] [chem 25]

[0269]

[0270] Under nitrogen atm...

Embodiment 3～5、 comparative example 1、2

[0290] The following polymers were synthesized by a synthetic method similar to that described.

[0291] [chem 30]

[0292]

[0293]ΔE (eV) calculated from the following formula was calculated for the polymers obtained in the above examples, and 2-5 and 2-6 synthesized for comparison.

[0294] ΔE(A)=S1(A)-T1(A)

[0295] ΔE(B)=S1(B)-T1(B)

[0296] The calculation results are shown in Table 1, and the GPC measurement results and solubility evaluation results are shown in Table 2. The case where ΔE satisfies 0.5 eV or less is defined as ΔE(A), and the case where ΔE exceeds 0.5 eV is defined as ΔE(B).

[0297] [Table 1]

[0298] polymer ΔE(A) ΔE(B) Example 1 P-4 0.03 - Example 2 P-13 0.19 0.73 Example 3 P-1 0.20 - Example 4 P-7 0.17 0.73 Example 5 P-12 0.03 - Comparative example 1 2-5 - 0.73 / 0.72 Comparative example 2 2-6 - 0.51

[0299] [Table 2]

[0300] polymer mw mn Mw / Mn S...

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Abstract

The present invention provides a polymer for organic electroluminescent elements, which has high luminous efficiency, and which is able to be applied to a wet process. This polymer for organic electroluminescent elements is used in at least one organic layer of an organic electroluminescent element that is obtained by stacking a positive electrode, one or more organic layers, and a negative electrode on a substrate; and this polymer for organic electroluminescent elements is characterized by containing a polymer which has a polyphenylene main chain represented by general formula (1), and which has thermally activated delayed fluorescence characteristics (TADF characteristics). (In the formula, x represents a phenylene group or linked phenylene groups; L represents a single bond, an aromatic hydrocarbon group or an aromatic heterocyclic group; A represents an aromatic hydrocarbon group, an aromatic heterocyclic group or linked aromatic groups; and (S1(A) - T1(A)) <= 0.50 (eV) is satisfied.).

Description

technical field [0001] The present invention relates to a polymer for organic electroluminescent elements, and organic electroluminescent elements (hereinafter referred to as organic electroluminescence (EL) elements), in detail, the present invention relates to a polymer with specific condensation A material for an organic EL device made of polyphenylene having an aromatic ring structure. Background technique [0002] In addition to the characteristics of high contrast, high-speed response, and low power consumption, organic EL elements also have structural and / or design features such as thin and / or light weight, and flexibility. In the fields of displays and lighting, Practicalization is rapidly advancing. On the other hand, there is still room for improvement in brightness, efficiency, lifespan, cost, etc., and various researches and developments related to materials and device structures are being carried out. [0003] In order to maximize the characteristics of the or...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/10C09K11/06H05B33/10H01L51/50
CPCC09K11/06C08G61/10C09K2211/1466C08G2261/12C08G2261/148C08G2261/1434C08G2261/135C08G2261/76C08G2261/312C08G2261/1646C08G2261/1412C08G2261/411C08G2261/51C08G2261/512C08G2261/514C08G2261/52C08G2261/95C09D165/00H10K85/111H10K85/151H10K50/11H10K2101/20H05B33/10H10K50/00C08G61/124C08G2261/124C08G2261/149C08G2261/18C08G2261/228C08G2261/3221C08G2261/3241H10K2101/10
Inventor 林健太郎井上栋智
Owner NIPPON STEEL CHEM &MATERIAL CO LTD
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