Abstract
Starting from N,N -diarylsubstituted
thioureas 20 and thioacetamides 21 a series of heterocyclic analogous of N,N′ -perarylated phenylene-1,4-diamines
and benzidines was obtained. These compounds represent, as studied
by DSC measurements, a new class of hole transporting materials
with high thermal stability and high tendency to form stable amorphous
states. Moreover, some of the new compounds are, as measured by
cyclic voltammetry, easily reversibly oxidized indicating the formation
of persistent radical ions. Such compounds, which are, in general,
completely substituted by aryl groups at their heterocyclic moieties,
have been successfully used as hole-transport materials in OLEDs.
Key words
heterocyclization - hole transport materials -
N -perarylated 2-aminothiophenes -
N -perarylated 2-aminothiazoles
References
1
Shirota Y.
SPIE
1990,
3148:
186 ; and references given therein
2
Koene BE.
Loy DE.
Thompson ME.
Chem. Mater.
1998,
10:
2235
3
Pai DM.
Yanus JF.
Stolka M.
J.
Phys. Chem.
1984,
88:
4714
4a
Rothberg LJ.
Lovinger AJ.
J. Mater. Res.
1996,
11:
3174
4b
Jüstel T.
Nikol H.
Ronda C.
Angew.
Chem., Int. Ed.
1998,
37:
3084 ; Angew. Chem . 1998 , 110 , 3250
5a
Garnier F.
Hajlaoui R.
Yassar A.
Srivastava P.
Science
1994,
265:
1684
5b
Brown AR.
Jarrett CP.
de Leeuw DM.
Matters M.
Synth.
Met.
1997,
88:
37
5c
Horowitz G.
Adv.
Mat.
1998,
10:
365
6a
Cariciftci NS.
Smilowitz L.
Heeger AJ.
Wudl F.
Science
1992,
258:
1474
6b
Halls JJM.
Walsh CA.
Greenham NC.
Marseglia EA.
Friend RH.
Moratti SC.
Holmes AB.
Nature
1995,
376:
498
7
Getautis V.
Stanisauskaité A.
Paliulis .
Uss S.
Uss V.
J. Prakt.
Chem.
2000,
342:
58
8
Ueta E.
Nakano H.
Shirota Y.
Chem. Lett.
1994,
2397
9a
Goodbrand HB.
Hu NX.
J. Org. Chem.
1999,
64:
670
9b
Abu-abdoun II.
Ledwith A.
Pure Appl.
Chem.
1998,
A35:
673
9c
Tanaka H.
Tokito S.
Okada A.
Chem. Commun.
1996,
2175
9d
Selby TD.
Blackstock SC.
J. Am.
Chem. Soc.
1998,
120:
12155
9e
Stickley KS.
Blackstock SC.
Mol.
Cryst. Liq. Cryst. Sci. Technol.
1995,
272:
81
9f
Stickley KS.
Blackstock SC.
Tetrahedron Lett.
1995,
36:
1585
9g
Ishikawa W.
Inada H.
Nakomo H.
Shirota Y.
Macromol. Symp.
1997,
125:
171
9h
Thelakkat M.
Bacher A.
Fink R.
Haubner F.
Schmidt HW.
Polym.
Prepr.
1997,
38:
396
9i
Thelakkat M.
Schmidt HW.
Adv. Mater.
1998,
10:
219
9j
Thelakkat M.
Schulz C.
Hohle C.
Strohriegl P.
Schmidt HW.
Hofmann U.
Schloter S.
Haarer J.
Phys. Chem. Chem. Phys.
1999,
1:
1693
9k
Kamiyama T.
Yasuda Y.
Shirota Y.
Polym.
J.
1999,
31:
1165
9l
Inada N.
Shirota Y.
J. Mater. Sci.
1993,
3:
219
10a
Thayumanavan S.
Barlow S.
Marder SR.
Chem. Mat.
1997,
9:
3231
10b
Koene BE.
Loy DE.
Thompson ME.
Chem. Mat.
1998,
10:
2235
10c
Bushby RJ.
Gooding D.
Vale ME.
Philos. Trans. R. Soc. London, Ser. A
1999,
357:
2939
10d
Yamamoto T.
Nishiyama M.
Koie Y.
Teterahedron
Lett.
1998,
39:
2367
10e
Yamamoto T.
Nishiyama M.
Koie Y.
Toso
Kankyu Hokoku
1997,
41:
49 ; Chem. Abstr. 1998 , 128 , 180
10f
Hartwig JF.
Goodson FE.
Luie J.
Hauck S.
Polym. Mater.
Sci. Eng.
1999,
80:
41
10g
Louie J.
Hartwig JF.
Frey A.
J.
Am. Chem. Soc.
1997,
119:
11695
11
Watanabe M.
Yamamoto T.
Nishiyama M.
Chem. Commun.
2000,
133
12a
Wong K.-T.
Hung TH.
Kao SC.
Chou CH.
Su YO.
Chem. Commun.
2001,
1628
12b
Gerstner,
P.; Hartmann, H.; Kanitz, A.; Rogler, W. patent submitted.
13
Becker HGO. In Organikum
19th
ed.:
Johann Ambrosius Barth;
Leipzig:
1993.
14a
Liebscher J. In
Thiazoles , Houben-Weyl, Methoden der Organischen Chemie
Vol.
E8b:
Georg Thieme;
Stuttgart:
1994.
p.1-398
14b
Wiley RH.
England DC.
Behr LC. In
The preparation
of thiazoles, Organic Reactions
Vol. 6:
;
:
1951.
p.367
15
Hartmann H.
Mayer R.
Z. Chem.
1966,
6:
28
16a 1-Naphdata: N ,N′ ,N′′ -tris(1-naphthyl)-1,3,5-trianilinoben-zene,
see: Shirota Y.
SPIE
1990,
186:
3148
16b α-NPD: N ,N′ -bis(1-naphtyl)-N ,N′ -diphenylbenzidine, see: Koene BE.
Loy DE.
Thompson ME.
Chem. Mater.
1998,
10:
2235
17 Kanitz, A.; Schumann, J.; Scheffel,
M.; Rajoelson, S.; Rogler, W.; Hartmann, H.; Rohde, D. Chem. Lett. 2002,
in press.
18
Lutz RE.
J.
Am. Chem. Soc.
1927,
49:
1106
19
Ruggli P.
Gassenmeier E.
Helv. Chim. Acta
1939,
22:
496
20
Hausknecht G.
Ber.
Dtsch. Chem. Ges.
1889,
22:
324
21
Neville RG.
McGee JJ.
Can. J. Chem.
1963,
41:
2123
22