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Crosslinkable host materials

A system and donor technology, applied in luminescent materials, electro-solid devices, semiconductor devices, etc., can solve the problems of short operating life, insoluble compounds, and difficult-to-purify materials processing and purification.

Inactive Publication Date: 2017-05-24
SAMSUNG DISPLAY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 1. Especially for blue or green emission, the operating lifetime is still short, so only simple applications are currently commercially available
[0004] 2. Some of the compounds used are difficult to dissolve in common organic solvents, so it is difficult to carry out purification during synthesis, processing of materials in solution and purification of devices during preparation of electronic equipment
[0005] 3. Materials used according to prior art generally have low triplet energy
When combined with materials that emit from the triplet state, this causes the emission to be quenched (quenched) and results in a decrease in efficiency

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0109] Example 1: Molecules according to the invention

[0110] All molecules with the crosslinkable group ethylene are shown in the list below. The person skilled in the art knows how to introduce alternative crosslinkable groups PG into molecules to obtain other molecules according to the invention.

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

Embodiment 2

[0122] Example 2: Synthetic sequence for the synthesis of molecules according to the invention such as 2-N-(carbazolyl)6-N-(3,6-divinylcarbazolyl)-pyridine (molecule 1)

[0123]

[0124] First replacement step:

[0125]Carbazole (10 mmol, 1.00 equiv) was mixed with sodium hydride (60% with paraffin, 500 mg, 13 mmol, 1.3 equiv) and dissolved in portions with a total of 110 mL of dioxane under nitrogen. The rate of addition was adapted to the formation of hydrogen to avoid foaming. After complete addition the reaction was stirred at room temperature for 15 minutes, then heated at reflux for 15 minutes. A clear yellow solution formed which fluoresced strongly under UV light (excitation at 366 nm). 2,6-Difluoropyridine (1.15 g, 10 mmol, 1.00 equiv) was added dropwise to the reaction mixture. Fluorescence was significantly reduced under ultraviolet light. The reaction mixture was heated at reflux until the reactants were completely reacted (reaction controlled by HPLC, GC-...

Embodiment 3

[0136] Example 3: Molecule 2

[0137] 2-N-(carbazolyl)-6-N-(3,6-di-(4-vinylphenyl)-carbazolyl)-pyridine (molecule 2).

[0138]

[0139] The synthesis was carried out similarly to the synthesis of molecule 1, but using (HO) 2 BPhCH=CH 2 as a boron derivative. Beige solid (50%). – 1 H NMR (500MHz, chloroform-d) δ=8.47–8.41(m,2H), 8.25–8.04(m,7H), 7.80–7.62(m,8H), 7.61–7.52(m,4H), 7.47(ddd ,J=8.5,7.2,1.3Hz,2H),7.38(td,J=7.5,1.0Hz,2H),6.82(dd,J=17.6,10.9Hz,2H),5.84(dd,J=17.5,0.9 Hz, 2H), 5.31 (dd, J = 10.9, 0.9Hz, 2H) ppm. – 13 C NMR (126MHz, chloroform-d) δ = 151.6, 151.41, 140.96, 139.49, 139.37, 136.51, 136.17, 134.37, 127.33, 127.0, 126.7, 126.7, 126.4, 125.8, 125.3, 124.6, 128.4, 120.4, 126.4, , 113.7, 112.5, 111.9ppm. –IR(ATR) 2922(vw), 1730(vw), 1625(vw), 1570(m), 1477(m), 1439(vs), 1375(m), 1324(m), 1220(m), 1186(m), 1029(w), 987(vw), 902(w), 841(w), 794(m), 747(s), 721(s), 668(vw), 640(vw), 597(vw),560(vw),499(vw),420(w)cm -1 . –.HRMS(FAB-MS,3-NBA,C 45 h ...

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Abstract

The invention relates to a crosslinkable organic molecule having a structure of the formula (1) and to the use thereof, wherein Ar is independently of one another, an unsaturated or aromatic carbo- or heterocyclic unit with 5 to 30 ring atoms, selected from the group consisting of naphthalene, anthracene, phenanthrene, pyrene, dihydropyrene, chrysene, perylene, fluoranthene, benzanthracene, tetracene, pentacene, benzpyrene, furan, benzofuran, isobenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazol, naphthimidazole, phenanthrimidazole, pyridimidazole, pyrazine-imidazole, quinoxalinimidazole, oxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, isothiazole, 1,3-thiazole, benzothiazole, pyridazine, benzopyridazine, pyrimidine, benzpyrimidine, quinoxaline, pyrazine, phenazine, naphthyridine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4-triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-triazine, 1,2,4-triazine, 1,2,3-triazine, tetrazole, 1,2,3,4- oxatriazole, 1,2,3,4-oxatriazole, 1,2,4,5-tetrazine, 1,2,3,4-tetrazine, 1,2,3,5-tetrazin, purine, pteridine, indolizine, benzothiadiazole, indenocarbazole, indenofluorene, spirobifluorene, and indolocarbazole; D1 is a donor group having a structure of the formula (1a); and D2 is a donor group having a structure of the formula (1b).

Description

technical field [0001] The present invention relates to organic molecules of the general formula 1 and their use as crosslinkable, liquid processable host materials in OLEDs (Organic Light Emitting Diodes) and other optoelectronic components. Background technique [0002] Organic electronic devices are increasingly used in commercial products or are about to enter market circulation. As examples of existing commercial products, mention is made of organic or polymeric light-emitting diodes (OLEDs, PLEDs) in display screen devices and display devices. Organic solar cell (O-SC), organic field effect transistor (O-FET), organic thin film transistor (O-TFT), organic switching element (O-IC), organic optical amplifier or organic laser diode (O-Laser) enter Advanced research stage and can realize great significance in the future. The general structure of organic electroluminescent devices is described, for example, in US 4539507 A, US 5151629 A, EP0676461 A and WO 98 / 27136 A. Bu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C07D401/14C07D413/14C07D417/14C07F9/6558C09K11/06H01L51/50H01L51/54
CPCC07D401/14C07D413/14C07D403/14C07D417/14C09K11/06C09K2211/1466C09K2211/1483C07F9/5728C07F9/65583Y02E10/549C08F26/06Y02P70/50H10K85/141H10K85/654H10K85/657H10K85/6572H10K50/11
Inventor D·沃尔兹
Owner SAMSUNG DISPLAY CO LTD
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