Synthesis and Characterization of the Bipolar Phosphorescence Host Material 3-(4-(9H-carbazol-9-yl)phenyl)-1methyl-4-phenylquinolin-2(1H)-one

doi:10.7517/j.issn.1674-0475.2010.06.408

Imaging Science and Photochemistry ›› 2010, Vol. 28 ›› Issue (6): 408-415.DOI: 10.7517/j.issn.1674-0475.2010.06.408

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Synthesis and Characterization of the Bipolar Phosphorescence Host Material 3-(4-(9H-carbazol-9-yl)phenyl)-1methyl-4-phenylquinolin-2(1H)-one

HUANG Da^1,3, YE Jun^1,3, ZHAO Wei-ming², ZHENG Cai-jun^1,3, WANG Jing^1,3, TAO Si-lu⁴, OU Xue-mei¹, ZHANG Xiao-hong¹

1. Technical Institute of Physics and Chemistry of Chinese Academy of Sciences, Beijing 100190, P.R.China;
2. Dongguan LITEWELL(OLED) Technology Incorporation, Dongguan 523656, Guangdong, P.R.China;
3. Graduate University of the Chinese Academy of Sciences, Beijing 100049, P.R.China;
4. University of Electronic Science and Technology of China, Chengdu 610054, Sichuan, P.R.China

Revised:2010-05-26 Online:2010-11-23 Published:2010-11-23

Abstract

Abstract: A new bipolar phosphorescence host material carbostyril derivative 3-(4-(9H-carbazol-9-yl)phenyl)-1-methyl-4-phenylquinolin-2(1H)-one was designed and synthesized.Through theoretical calculations we found that the HOMO and LUMO obitals respectively localed in carbazole group and carbostyril group,that imply this compound is a good bipolar material.The compound phosphorescence emission is 515 nm(2.41 eV),meet the basic requirement of green phosphorescence host material(>2.40 eV).TGA and DSC results show the compound has high thermal stabilities,the decomposition temperature and glass transition temperature are 312 ℃ and 105 ℃ respectively.The results show that the new compound is a potential green phosphorescence host material with bipolar feature.

Key words: OLEDs, bipolar green phosphorescence host material, carbostyril derivatives

CLC Number:

HUANG Da, YE Jun, ZHAO Wei-ming, ZHENG Cai-jun, WANG Jing, TAO Si-lu, OU Xue-mei, ZHANG Xiao-hong. Synthesis and Characterization of the Bipolar Phosphorescence Host Material 3-(4-(9H-carbazol-9-yl)phenyl)-1methyl-4-phenylquinolin-2(1H)-one[J]. Imaging Science and Photochemistry, 2010, 28(6): 408-415.

References

[1] Tang C W,VanSlkes S A.Organic electroluminescent diodes[J]. Appl.Phys.Lett.,1987,51:913.
[2] Tang C W,VanSlyke S A,Chen C H.Electroluminescence of doped organic thin fil ms[J]. J.Appl.Phys.,1989,65:3610-3616.
[3] Steuber F,Staudigel J,et al.White light emissionfromorganic LEDs utilizing spiro compounds with high-tem-perature stability[J]. Adv.Mater.,2000,12:130-133.
[4] Baldo MA,O'Brien D F,et al.Highly efficient phosphorescent emissionfromorganic electroluminescent devices[J]. Nature,1998,395:151-154.
[5] Tao Y T,Wang Q,et al.Asi mple carbazole/oxadiazole hybrid molecule:an excellent bipolar host for greenand red phosphorescent OLEDs[J]. Angew.Chem.Int.Ed.,2008,47:8104-8107.
[6] Jeon S O,Yook KS,et al.Phenylcarbazole-based phosphine oxide host materials for high efficiencyin deep bluephosphorescent organic light-emitting diodes[J]. Adv.Funct.Mater.,2009,19:3644-3649.
[7] Xiao L X,Su S J,et al.Nearly 100%internal quantumefficiencyin an organic blue-light electrophosphorescentdevice using a weak electron transporting material with a wide energy gap[J]. Adv.Mater.,2009,21:1271-1274.
[8] Gao Z Q,Luo M M,et al.Newhost containing bipolar carrier transport moiety for high-efficiency electrophos-phorescence at lowvoltages[J]. Adv.Mater.,2009,21:688-692.
[9] Michael MR,Stephan H,et al.Donor-substituted 1,3,5-triazines as host materials for blue phosphorescent or-ganic light-emitting diodes[J]. Chem.Mater.,2010,22:2403-2410.
[10] Chen C T,Wei Y,et al.Doubly ortho-linked quinoxaline/diphenylfluorene hybrids as bipolar,fluorescent cha-meleons for optoelectronic applications[J]. J.Am.Chem.Soc.,2006,128:10992 10993.
[11] Dileep A K V,Joseph C D,et al.Acridinone/amine(carbazole)-based bipolar molecules:efficient hosts for flu-orescent and phosphorescent emitters[J]. Org.Lett.,2009,11:4310^-4313.
[12] Gribble G W,Smith MS.Metanolysis of phenyl-substituted benzhydryl chlorides[J]. J.Org.Chem.,1971,36:2724-2727.
[13] Park K,Lee J.Facile synthesis of 4-phenylquinolin-2(1 H)-one derivatives from N-acyl-o-aminobenzophenones[J]. Tetrahedron,2004,60:2993-2999.
[14] Glasnov T N,Stadlbauer W,et al.Microwave-assisted multistep synthesis of functionalized 4-arylquinolin-2(1h)-ones using palladium-catalyzed cross-coupling chemistry[J]. J.Org.Chem.,2005,70:3864-3870.
[15] Kresse G,Joubert D.From ultrasoft pseudopotentials to the projector augmented-wave method[J]. Phys.Rev.B,1999,59:1758.
[16] Kresse G,Furthmüller J.Efficient iterative schemes for ab initio total-energy calculations using a plane-wavebasis set[J]. Phys.Rev.B,1996,54:11169.
[17] 黄春辉,李富友,等.光电功能超薄膜[M]. 北京:北京大学出版社,2001.196-197.Huang C H,Li F Y,et al.Ultrathin Fil mfor Optics and Electronics[M]. Beijing:Peking University Press,2001.196-197.
[18] Baldo M A,Lamansky S,et al.Very high-efficiency green organiclight-emitting devices based on electrophos-phorescence[J]. Appl.Phys.Lett.,1999,75:4.

Synthesis and Characterization of the Bipolar Phosphorescence Host Material 3-(4-(9H-carbazol-9-yl)phenyl)-1methyl-4-phenylquinolin-2(1H)-one

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