녹색발광 6-알킬-3-크로몬알데히드(2,2-디알킬)하이드라존 유도체의 합성

정평진; 장홍준; Pyung Jin Chung; Hong Joon Chang

Applied Chemistry for Engineering, Vol.21, No.4, 424-429, August, 2010

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녹색발광 6-알킬-3-크로몬알데히드(2,2-디알킬)하이드라존 유도체의 합성

Synthesis of 6-Alkyl-3-Chromonealdehyde(2,2-dialkyl)hydrazone Derivatives for Green Light Emitting Materials

정평진^†, 장홍준

단국대학교 신소재공학과

Pyung Jin Chung^†, and Hong Joon Chang

Department of Materials Science and Engineering, Dankook University, Cheonan 330-714, Korea

E-mail:

초록

본 연구는 유기발광디바이스용(OLED) 녹색발광재료인 6-알킬-3-크로몬알데히드(2,2-디알킬)하이드라존 유도체의 합성에 관한 것으로서, 유도체들은 탈수축합반응으로 합성되었다. 이들은 전자흡인성의 6-알킬-3-크로몬알데히드류와 전자공여성의 2,2-디알킬하이드라존류의 공액구조를 가지고 있다. 합성된 물질들은 각각 FT-IR, 1H-NMR 스펙트럼으로부터 그의 구조적 특성을 확인하였고, 융점, 수득률에 의하여 열적 안정성, 반응성을 확인하였으며, 여기스펙트럼과 발광스펙트럼으로부터 자외가시광과 발광특성을 확인하였다.

6-Alkyl-3-chromonealdehyde (2,2-dialkyl)hydrazone derivatives were synthesized by dehydration condensation. They are green-emitting materials for organic light emitting device (OLED) composed of electron acceptor of 6-alkyl-3-chromonealdehydes and electron donor of 2,2-dialkylhydrazones in a conjugated structure. The structural properties of reaction products were analyzed by FT-IR and 1H-NMR spectroscopy. The thermal stabilities and reactivities were measured by melting points and yields. The UV-visibles and PL properties were also determined by excitation spectra and emission spectra, respectively.

Keywords:6-methyl-3-chromonealdehyde;6-isopropyl-3-chromenealdehyde;1,1-diphenylhydrazine;1-methyl-1-phenylhydrazine;1,1-dimethylhydrazine

[References]

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Adachi C, Tsutui T, Saito S, Appl. Phys. Lett., 55, 1489 (1989)
Kido J, Ohtaki C, Hongawa K, Okuyama K, Nagai K, JPN, J. Appl. Phys., 32, L917 (1993)
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Yoshino K, Love P, Onoda M, Sugimoto R, JPN, J. Appl. Phys., 27, L2388 (1998)
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[1] Hagler TW, Pakbaz K, Voss K, Heeger AJ, Phys. Rev., B, 44, 8652 (1992)

[2] Pope M, Kallmann HP, Magnante P, J. Chem. Phys., 38, 2042 (1962)

[3] Tang CW, VanSlyke SA, Appl. Phys. Lett., 51, 902 (1987)

[4] Helfrich W, Schneider WG, Phy. Rev. Lett., 14, 229 (1965)

[5] Adachi C, Tokito S, Tsutsui T, Saito S, JPN, J. Appl. Phys., 27, L713 (1988)

[6] Burroughes JH, Bradley DDC, Brown AR, Marks RN, Mackay K, Friend RH, Burnm PL, Holmes AB, Nature, 374, 539 (1990)

[7] Kido J, Hayase H, Hongawa K, Nagai K, Okuyama K, Appl. Phys. Lett., 65, 212 (1994)

[8] Kim DU, Tsutsui T, J. Appl. Phys., 80, 4785 (1996)

[9] Yang Z, Sokolik I, Karatz FE, Macromolecules, 26, 1188 (1993)

[10] Ding XB, Synthetic Matals, 142, 267 (2004)

[11] Tang CW, VanSlyke SA, Chen CH, J. Appl. Phys, 65, 3610 (1989)

[12] Saito S, Tsutsui T, Era M, Takada N, Adadhi C, Hamada Y, Yakimoto T, Proc. SPIE, 1910, 212 (1993)

[13] Tokito S, Tsutui T, Taga Y, J. Appl. Phys., 86, 2407 (1999)

[14] Hamada Y, Kanno H, Tsujioka T, Takahashi H, Usuki T, Appl. Phys. Lett., 75, 1682 (1999)

[15] Adachi C, Tsutui T, Saito S, Appl. Phys. Lett., 55, 1489 (1989)

[16] Kido J, Ohtaki C, Hongawa K, Okuyama K, Nagai K, JPN, J. Appl. Phys., 32, L917 (1993)

[17] Carrard M, Goncalves-Conto S, Si-Ahmed L, Ades D, Siove A, Thin Solid Films, 352(1-2), 189 (1999)

[18] Yoshino K, Love P, Onoda M, Sugimoto R, JPN, J. Appl. Phys., 27, L2388 (1998)

[19] Hayashi S, Etoh H, Saito S, JPN, J. Appl. Phys., 25, L773 (1986)