Diaminoanthracene Derivatives as High-Performance Green Host Electroluminescent Materials

Abstract

Diaminoanthracene derivatives 9,10-bis(1-naphthylphenylamino)anthracene (α-NPA), 9,10-bis(2-naphthylphenylamino)anthracene (β-NPA), 9,10-bis(m-tolylphenylamino)anthracene (TPA), and 9,10-bis(diphenylamino)anthracene (PPA) were conveniently synthesized from the corresponding diarylamine and 9,10-dibromoanthracene in the presence of Pd(OAc)2, tri-tert-butylphosphine, and sodium tert-butoxide in o-xylene. Electroluminescent devices using α-NPA, β-NPA, and PPA as the hole transporters and host emitters were made. Devices consisting of diaminoanthracene (α-NPA, β-NPA, or PPA)/Alq3 were shown to emit intensive green light from the diaminoanthracene layer instead of the Alq3 layer. The device performance can be further improved by employing CuPc as the hole-injection layer, α-NPB or m-MTDATA as the hole-transporting layer, and Alq3 or TPBI as the electron-transporting layer. Very high brightness, current, and power efficiencies and excellent CIE coordinates can be achieved by a suitable combination of these layers. For example, device K, which consists of m-MTDATA(20 nm)/β-NPA(40 nm)/TPBI(50 nm), emits green light at 530 nm and shows a maximum external quantum efficiency of 3.68%, current efficiency of 14.79 cd/A, power efficiency of 7.76 lm/W, and maximum brightness of 64991 cd/m2.

Crystal structure of 3-diphenylamino-benzo[de]anthracen-7-one, C29H19NO

“…Arylamines can be obtained either by the copper-catalyzed Ullmann condensation or palladium-catalyzed cross-coupling reactions [4][5][6][7][8][9]. Ullmann reactions involve rather high temperatures and prolonged reaction times and are limited to aryl iodides.…”

The synthesis and photophysical properties of novel triphenylamine derivatives containing α, β-diarylacrylonitrile

“…As a continuation of the author's long-standing interest in organic light emitting devices [15,16] and palladium-catalyzed coupling reactions [17,18], interest became focused on the preparation of novel, functionalised, triphenylamine derivatives as potential standard hole transport materials [19,20]. This paper reports the design and synthesis of several novel, triphenylamine derivatives with a, b-diarylacrylonitrile [21,22] that contain both a nitrile group and triphenylamine and which offer potential application as dyes, pigments and OLED materials.…”

Color Pure and Stable Blue Light Emitting Material Containing Anthracene and Fluorene for OLED

“…[4][5][6][7][8][9][10][11] Moreover, various bulky substituents at 9, 10 positions of anthracene can be easily introduced. Fluorene also has a number of advantages, including its capability to emit in the blue part of the visible spectrum, chemical and photochemical stability, easy synthesis with high purity, liquid crystalline properties and durability under operation in a LED.…”