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Molecular orientation of a new anthracene derivative for highly-efficient blue fluorescence OLEDs
Sohn, S.,Kim, M.J.,Jung, S.,Shin, T.J.,Lee, H.K.,Kim, Y.H. Elsevier Science 2015 ORGANIC ELECTRONICS Vol.24 No.-
A new anthracene derivative of 9,10-bis(2,5-dimethyl-4-(naphthalen-2-yl)phenyl)-2,3-diphenylanthracene (BDNPA) was designed and synthesized as a non-doped blue emitter in organic light emitting diodes (OLEDs). BDNPA has highly rigid structure and thermal stability with decomposition temperature (corresponding to 5% weight loss) of 490<SUP>o</SUP>C, because p-naphthyl xylene groups in 9,10-positions were highly twisted to anthracene core due to steric hindrance of xylene groups, and because the 2,3-diphenyl groups were also twisted about 45-49<SUP>o</SUP> to anthracene. OLEDs with BDNPA non-doped emitter showed high efficiency of 5.21cd/A due to the carrier mobility with well-aligned π-stacking structure toward out-of-plane by the face-on orientation by grazing incidence X-ray diffraction.
Liu Cheng,Zhang Dongdong,Duan Lian 한국정보디스플레이학회 2020 Journal of information display Vol.21 No.3
The stability of blue organic light-emitting diodes (OLEDs) is highly restricted by both the low electron transport mobility and the stability of the electron transport materials (ETMs). Anthracene-derivative-type ETMs have been proven to be potential materials for solving the aforementioned problem, but their performance still needs to be improved. In this study, a novel anthracene derivative with an asymmetric structure was developed as an ETM in deep-blue devices, realizing a 10.41 cd/A current efficiency, a low driving voltage of 4.04 V, (0.139, 0.047) Rec. 2020 CIE coordinates, and a long T99 lifetime of over 100 h at the 20 mA/cm2 current density. Single-crystal diffraction showed that ET-01 has a face-to-face π-π stack, which is the reason for its good performance. Notably, when the lithium quinolate (Liq) doping ratio was further tuned, one of the devices showed no obvious degradation after 140 h of continuous operation at 20 mA/cm2, representing the champion data in the scientific literature.
A First Synthesis and Physical Properties of Asymmetric Anthracenes-Thiophenes Bridged with Ethylene
Min Ji Hwang,Ji Hee Park,Eun Bin Jeong,Il Kang,Dong Hoon Lee,박찬언,O. M. Singh,Hojune Choi,김윤희,윤용진,권순기,이상경 대한화학회 2012 Bulletin of the Korean Chemical Society Vol.33 No.11
Here we report our recent result of a new semiconductor material, which has an asymmetric structure. The synthesized molecules consist of anthracene and thiophene connected by bridged ethylene and substituted with hexyl or dodecyl groups as pendants. The semiconductors were synthesized using a McMurry coupling reaction between anthracene-2-carbaldehyde and corresponding 5-hexyl(or dodecyl)thiophene-2-carbaldehyde. A first investigation of synthesized asymmetry AVHT (9a) and AVDT (9b) for the physical properties showed that they have high oxidation potential and thermal stability. The devices prepared by using AVHT (9a) and AVDT (9b) showed the mobility of 2.6 × 10−2 cm2/Vs and 4.4 × 10−3 cm2/Vs, respectively, in solution processed OTFTs.
A First Synthesis and Physical Properties of Asymmetric Anthracenes-Thiophenes Bridged with Ethylene
Hwang, Min Ji,Park, Ji Hee,Jeong, Eun Bin,Kang, Il,Lee, Dong Hoon,Park, Chan Eon,Singh, O.M.,Choi, HoJune,Kim, Yoon-Hi,Yoon, Yong Jin,Kwon, Soon-Ki,Lee, Sang-Gyeong Korean Chemical Society 2012 Bulletin of the Korean Chemical Society Vol.33 No.11
Here we report our recent result of a new semiconductor material, which has an asymmetric structure. The synthesized molecules consist of anthracene and thiophene connected by bridged ethylene and substituted with hexyl or dodecyl groups as pendants. The semiconductors were synthesized using a McMurry coupling reaction between anthracene-2-carbaldehyde and corresponding 5-hexyl(or dodecyl)thiophene-2-carbaldehyde. A first investigation of synthesized asymmetry AVHT (9a) and AVDT (9b) for the physical properties showed that they have high oxidation potential and thermal stability. The devices prepared by using AVHT (9a) and AVDT (9b) showed the mobility of $2.6{\times}10^{-2}cm^2/Vs$ and $4.4{\times}10^{-3}cm^2/Vs$, respectively, in solution processed OTFTs.
Optical Properties of Organic Semiconductor Thin Films: 2,6,9,10-Tetrakis(phenylethynyl)anthracene
이호석,이호선,허정아,조민주,최동훈,강태동 한국물리학회 2013 THE JOURNAL OF THE KOREAN PHYSICAL SOCIETY Vol.62 No.6
Two kinds of anthracene derivative thin films, 2,6-bis((4-hexylphenyl)ethynyl)-9,10-bis(phenyl ethynyl)anthracene (B-ant-THB) and 9,10-bis((4-hexyl phenyl)ethynyl)-2,6-bis (phenyl ethynyl)anthracene (HB-ant-TB) were synthesized to investigate their optical properties. The difference between the two anthracene derivatives consisted of the position of 1-ethynyl-4-hexylbenzene group substitutions into an anthracene ring. We measured the optical properties of the anthracene derivatives using photoluminescence (PL), transmittance spectroscopies, and spectroscopic ellipsometry. The dielectric functions of the two films were similar with respect to transition energies, but were different in terms of amplitudes. Optical band gap energies of B-ant-THB and HB-ant-TB film states were estimated to be 2.45 and 2.34 eV, respectively, whereas DFT calculations of isolated molecular states showed the same value of 2.42 eV. The large bathochromic shift of the HB-ant-TB film state compared to the DFT calculation is attributed to strong intermolecular coupling between the HB-ant-TB molecules in the crystalline film because HB-ant-TB film has higher crystallinity than B-ant-THB film. The symmetric structures of the transmittance and PL spectra of the anthracene derivative films were observed as distinct peaks having similar vibrational energy levels of singlet ground state and first excited state.
Solution Processable Symmetric 4-Alkylethynylbenzene End-Capped Anthracene Derivatives
Sang Hun Jang,Hyun Jin Kim,Min Ji Hwang,Eun Bin Jeong,Hui-Jun Yun,Dong Hoon Lee,김윤희,박찬언,윤용진,권순기,이상경 대한화학회 2012 Bulletin of the Korean Chemical Society Vol.33 No.2
New candidates composed of anthracene and 4-alkylethynylbenzene end-capped oligomers for OTFTs were synthesized under Sonogashira coupling reaction conditions. All oligomers were characterized by FT-IR, mass,UV-visible, and PL emission spectrum analyses, cyclic voltammetry (CV), differential scanning calorimetry (DSC), thermal gravimetric analysis (TGA), 1H-NMR, and 13C-NMR. Investigation of their physical properties showed that the oligomers had high oxidation potential and thermal stability. Thin films of DHPEAnt and DDPEAnt were characterized by spin coating them onto Si/SiO2 to fabricate top-contact OTFTs. The devices prepared using DHPEAnt and DDPEAnt showed hole field-effect mobilities of 4.0 × 10.3 cm2/Vs and 2.0 ×10.3 cm2/Vs, respectively, for solution-processed OTFTs.
Solution Processable Symmetric 4-Alkylethynylbenzene End-Capped Anthracene Derivatives
Jang, Sang-Hun,Kim, Hyun-Jin,Hwang, Min-Ji,Jeong, Eun-Bin,Yun, Hui-Jun,Lee, Dong-Hoon,Kim, Yun-Hi,Park, Chan-Eon,Yoon, Yong-Jin,Kwon, Soon-Ki,Lee, Sang-Gyeong Korean Chemical Society 2012 Bulletin of the Korean Chemical Society Vol.33 No.2
New candidates composed of anthracene and 4-alkylethynylbenzene end-capped oligomers for OTFTs were synthesized under Sonogashira coupling reaction conditions. All oligomers were characterized by FT-IR, mass, UV-visible, and PL emission spectrum analyses, cyclic voltammetry (CV), differential scanning calorimetry (DSC), thermal gravimetric analysis (TGA), $^1H$-NMR, and $^{13}C$-NMR. Investigation of their physical properties showed that the oligomers had high oxidation potential and thermal stability. Thin films of DHPEAnt and DDPEAnt were characterized by spin coating them onto Si/$SiO_2$ to fabricate top-contact OTFTs. The devices prepared using DHPEAnt and DDPEAnt showed hole field-effect mobilities of $4.0{\times}10^{-3}cm^2$/Vs and $2.0{\times}10^{-3}cm^2$/Vs, respectively, for solution-processed OTFTs.
한재필,이의진,허수원,송호준,문두경 한국공업화학회 2014 한국공업화학회 연구논문 초록집 Vol.2014 No.1
In conventional structure polymer solar cells (PSCs), PEDOT:PSS is the most commonly used material as the hole transporting layer on ITO anode. However, PEDOT:PSS can cause lowering performance and long-term stability of PSCs due to their acidity and hygroscopicity. For those weaknesses, inverted structure PSCs have received a lot of attentions. Metal oxides such as ZnO and TiOx are usually used as the electron collecting layer in inverted structure PSCs because of their high transmittance and good carrier mobility. However, inorganic electron collecting layer could have poor interfacial contact with photoactive layer, resulting in low carrier mobility. In this study, we synthesized anthracene derivative which has good alcohol-water solubility, electron collection and interfacial contact with photoactive layer, and it was introduced as the electron transporting layer in low bandgap polymer- based inverted solar cells. As a result, the power conversion efficiency (PCE) and stability were enhanced compared with conventional structure PSCs.
Pure blue emission from undoped organic light emitting diode based on anthracene derivative
Bangdong Ding,Wenqing Zhu,Xueyin Jiang,Zhilin Zhang 한국물리학회 2008 Current Applied Physics Vol.8 No.5
This paper presents organic light emitting diodes (OLEDs) which were fabricated by using undoped 9,10-di(2-naphthyl)anthracene (ADN) as the emitting layer, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-amine (TPD) as the hole transporting layer, and one of tris-(8-hydroxy-quinolinato) aluminum (Alq3), 4,7-diphenyl-1,10-phenanthroline (Bphen) and 2-tert-butylphenyl-5-biphenyl- 1,3,4-oxadiazole (PBD) as the electron transporting layer. By optimization for the thickness of device, efficient pure blue organic light emitting diodes were obtained, which is attributed to the synergy of both the hole transporting layer and the electron transporting layer. This paper presents organic light emitting diodes (OLEDs) which were fabricated by using undoped 9,10-di(2-naphthyl)anthracene (ADN) as the emitting layer, N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-amine (TPD) as the hole transporting layer, and one of tris-(8-hydroxy-quinolinato) aluminum (Alq3), 4,7-diphenyl-1,10-phenanthroline (Bphen) and 2-tert-butylphenyl-5-biphenyl- 1,3,4-oxadiazole (PBD) as the electron transporting layer. By optimization for the thickness of device, efficient pure blue organic light emitting diodes were obtained, which is attributed to the synergy of both the hole transporting layer and the electron transporting layer.
Effect of the Length of Side Group Substitution on Optical and Electroluminescene Properties
Hwangyu Shin,Hyeonmi Kang,Beomjin Kim,Youngil Park,Young-Jun Yu,박종욱 대한화학회 2014 Bulletin of the Korean Chemical Society Vol.35 No.10
Blue emitting materials, 9,10-bis-biphenyl-4-yl-anthracene (AC-P), 9,10-bis-[1,1';4',1'']terphenyl-4-yl-anthracene (AC-DP), and 9,10-bis[3'',5''-deiphenyltriphenyl-4'-yl]anthracene (AC-TP) were synthesized through boration and Suzuki aryl-aryl coupling reaction. EL performance of blue light-emitters was optimized and improved by varying the chemical structures of the side groups. In the thin film state, the three materials exhibit PLmax values in the range of 442-456 nm. EL device with the synthesized compounds in the following configuration was fabricated: ITO/4,4',4''-tris(N-(2-naphthyl)-N-phenylamino)triphenylamine (2-TNATA) 60nm/N,N'-bis (naphthalene-1-yl)-N,N'-bis(phenyl)benzidine (NPB) 15nm/synthesized blue emitting materials (30nm)/1,3,5- tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi) 20nm/LiF 1nm/Al 200nm. The current efficiency and C.I.E. value of AC-TP were 3.87 cd/A and (0.15, 0.12). A bulky and non-planar side group helps to prevent π-π* stacking interaction, which should lead to the formation of more reliable amorphous film. This is expected to have a positive effect on the high efficiency of the operating OLED device.