Giant domain formation in a thin film of bisstyrylanthracene derivatives by a simple melt process

Article abstract of DOI:10.1080/15421400490506432

Bisstyrylanthracene derivatives with long alkyl side chains (BSA), which were prepared into the thin films composed of giant anisotropic domains by simple melt process, showed interesting property. The derivatives that changed the chains length and chains

Full text of DOI:10.1080/15421400490506432

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Giant Domain Formation
in a Thin Film of
Bisstyrylanthracene Derivatives
by a Simple Melt Process
a
a
Misuzu Konishi , Katsuhiko Fujita & Tetsuo Tsutsui
a
a
Department of Applied Science for Electronics
and Materials, Interdisciplinary Graduate School of
Engineering Science , Kyushu University , Fukuoka,
Japan
Published online: 18 Oct 2010.
To cite this article: Misuzu Konishi , Katsuhiko Fujita & Tetsuo Tsutsui (2004)
Giant Domain Formation in a Thin Film of Bisstyrylanthracene Derivatives by a
Simple Melt Process, Molecular Crystals and Liquid Crystals, 425:1, 11-19, DOI:
10.1080/15421400490506432
To link to this article: http://dx.doi.org/10.1080/15421400490506432
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Mol. Cryst. Liq. Cryst., Vol. 425 , pp . 11 =[28 9] –1 9 =[29 7] , 200 4
Co py r ig h t # Ta yl or & F ra nc is I nc .
I SSN: 15 42- 140 6 p r int =1 563- 5287 onl ine
D O I : 10 .10 80 =15 421 400 490 506432
GI A N T D OMA IN FOR M AT ION IN A T HI N F IL M O F
B IS STYRY LA N THR A CEN E D ER I VAT IV ES B Y A
S IMP L E MELT P R OCESS
Misuzu Konishi, Katsuhiko Fujita, and Tetsuo Tsutsui
Department of Applied Science for Electronics and Materials,
Interdisciplinary Graduate School of Engineering Science,
Kyushu University, Kasuga, Fukuoka 816-8580, Japan
Bisstyrylanthracene derivatives with long alkyl side chains (BSA), which were
prepared into the thin films composed of giant anisotropic domains by simple
melt process, showed interesting property. The derivatives that changed the
chains length and chains form were synthesized. We introduced the film prep-
aration and investigated thermal properties of the films using differential
scanning calorimetry (DSC), polarization micrograph, and fourier transform
infrared spectroscopy (FT-IR). The phenomena of the giant domain formation
and phase transition in BSA films are discussed.
Keywords: a n iso tr op i c d oma in ; or g an ic f ilm p r ep a r at ion ; ph as e tr ans i tion
INTRODUCTION
T h e st ud y on de v i ce s co n sist in g o f o r gan ic t h in f ilms is in t h e sp o t ligh t ,
r e c e nt l y. In t ho se d ev ice s, o r gan ic ma t er ia ls ar e ex p e c t ed t o p la y v ar i ou s
imp or t an t r ol e s as n ot o nl y in su la to r s b ut al so se mic on d u c t or s. E sp ec ial l y
in or g a ni c t hi n fi lm f iel d ef f ec t t r an sist o r (FE T), wid e v ar ie t y of d ev i c e
st ru ct ur e ha s be e n d emo n st r a t ed [ 1] . Fo r ex a mp l e, it wa s f ab r ic a t ed on a
fl ex i bl e su bst r a t e [ 2,3 ] , w as em be d d ed el ec t r od es in t o p oly m er f ilms [4 ],
o r wa s i nt e g r a te d w it h a li gh t em it t in g d io de [5 ]. O n e of t h e su b st an t ia l
a d va nt a g e s of us in g o r gan ic mat e r ia ls is su c h wid e v ar i a t ion of d ev i c e
d e si g n.
Rec eiv ed 1 Oc t ober 200 3; ac ce p t ed 13 M ar c h . 200 4.
Ad d r ess c or r es p ond e nce t o Te tsu o Tsu t su i, De p ar t me nt of A ppl i ed Sc ie nc e for E le ctr on ics
a n d M a ter ia ls, In ter d i scip lin a r y Gr a d ua t e S ch o ol of En g in e er in g Sc ie nc e, Ky us hu Un ive r si ty,
K a su ga , Fu k u oka 81 6 -85 80, J ap a n . Te l.: þ 81- 92- 583- 7533, F ax : þ 81- 92– 575- 2318, E -ma il :
ts uigz @mb ox.n c .kyu sh u - u .ac .jp
11=[ 289]

1
2=[ 29 0]
M. Konishi et al.
G e ne r a l ly, t he f ilm p r ep ar a ti on p r oc es se s suc h a s v ac u u m d ep osi ti o n or
sp i n c oa t ing , a r e u sed , b ec au s e t h e amo r p h o u s f ilms p r ep a r ed b y t h ose
p r oc e sse s a r e sui ta b le t o min im i ze t h e d oma in b ou n d a r y ef f ec t s. Th ou gh
th e fe w ma te r i al s w hi ch t en d t o b e o r gan iz ed a s a p oly cr y st a lli n e f ilm su c h
a s pe n t ac e n e or o ti go t h iop h en e sh ow h ig h car r ie r mob il it y in FE Ts [6 ,7] ,
th e bo un da r y e ff e ct ca n b e r ed u ce d as t h e g r ain size is en la r ged , in id ea l
c ase t o a si ng l e cr y st al.
Si n ce i t i s qu ite d if fi c u lt t o o b t ain la r ge sin g le c r yst a l of or g an ic ma t er ia l,
it wou l d be a su b st a n t ial t ar g e t o f t h e r es ea r ch t o f ab r i c at e a d e v ic e wit h
h ig hl y or d e r e d m ol ecu l ar ar r a ng eme n t . I t h as b ee n r ep or t e d t h at t h e c ar-
r ie r t ra n spo r ta t io n w as imp r o ved o wi n g t o t h e h i gh or d er of or g an ic mol e -
c u le s i n l iq ui d c ry st als [ 8,9 ] .
0
0
we sy nt he s i z e d 9 ; 1 0 - Bis (4 ; 4 - alk y o xy st yr yl) a n th r a c en e (BS A ) wit h
lo ng a lk y l c ha i ns (Fi g. 1 ). Amo n g t h em, o nes h a vin g lon g a lkyl c h ain s
(n >10 ) sh owe d an is ot r o pi c d oma in f or m at io n in f ilm p r ep a r ed b y a simp le
me l t pr o ce s s. X - r ay d if fr a ct io n an al ysi s o f t h e BS A f ilms h a s a lr ea d y
r e v ea l e d t ha t t he f or m la ye r ed st r u ct u r e p ar a llel t o t h e su b st r a t e wit h a
la ye r sp ac i ng c or r es po n di n g t o t h e mo le cu l ar l en gt h . I n t h e p r ese n t st u d y,
we i nv e st i g a te d t h e t h er ma l p r op e r t ie s o f t h e ma t er ia ls a n d f ilms wit h d if -
fe r e nt i a l sc a nn in g ca lo r im et r y (D S C ), p ol ar iz at io n mic r og r a ph , a n d f ou r i er
tr an sfo r m i nfr a r ed sp ec tr o s co p y (FT- IR ), t o d is cu ss a b o u t t h e g ia n t d oma in
fo rm a ti on i n B SA f ilms.
EXPERIMENTAL SECTION
Synthesis
To e xa mi ne t he in f lu en c e o f sid e al ky l ch ai n on t h e p h ase b eh a v ior, we
sy nt he si z e d t he se r ies o f BS As w it h d i f fe r en t c h ain len g t h (F ig. 1).
F IGU RE 1 Sy nt hes is a n d c h em ic a l s t r uc t u r e of B SA .

Giant Domain Formation in a Thin Film
13=[ 291]
1- br o moa l ka n e an d 4 -h y dr o x yb e nz ald e h yd e we re d issol ve d in d r y a ce t-
o ne . Po ta ssi um c a r bo n at e an d p ot as siu m io d id e we re a d de d t o t h e sol ut ion ,
a n d r e fl ux e d un de r n it r og en f or 2 4 h . Fil t ra t ed f r om t h e h ot r ea c ti o n mix -
tu r e a nd t he sol v en t w as r emo v e d b y ev ap o r at i on . A ft e r, h ex a n e a n d wa t er
we r e a dd e d i nt o th e co n d en se d so lu t io n , t h e o r g an ic la yer wa s wa sh ed wit h
wa t e r se v e r a l t im es . Af t er p ur i fi cat io n b y a s ilic a- gel c olu mn c h r oma t o-
g r a ph y ( ch lo r ofo rm as el u a t e) , t h e (1 ) w as o b t ain ed . (S c h eme 1) I n t h e
sy n t he si s of B SA 6 1 0 h avi n g 2 -h e x yl de cy l gr o up , t h e h yd r ox yl gr o up of
2
-h e xy l -1 -d e ac n o l w as su b st it u te d b y b r o mid e b ef or e S c he me 1.
0
9
; 10 -b i sc hr ol o met h yl an t h r ace n e (p u r c h ase d f r om A ld r ic h ) wa s d is-
so lv e d i n m-x y le n e an d it w as r ef lu x ed w it h t r iet h yl p h osp h it e. Coo lin g
to t he r oom t emp er a t u re , t h e li gh t ye ll o w p r ec ip it a t e wa s ob t a i n ed . I t
wa s pu r ifi e d by re cr y st al liz at io n f r om cy cl o h ex a n e t o ob t a in p r od u c t (2) .
(S c he me 2)
Th e me t h a no li c so lu t io n o f so di um me t h ox id e wa s a d de d d r op w ise in t o
th e mi xt ur e of pr od u c t (1 ) an d (2 ) in D M F. Af t er of st ir r in g f or 12 h , t h e
p r ec i pi ta t e wa s fil te r ed o ff , w ash ed w it h w at er a n d d r ied in v ac u u m. Th e
c r ud e pr o du c t w as p ur i fi ed b y sil ica - ge l c olu mn c h r oma t og r ap h y
(
t o lu e ne : he x a ne ¼ 4 :1 ), an d r ec r yst a ll ize d f r om c yc loh ex a n e 3 t ime s. Th e
r e s ul t e d y e l low n ee dl e cr y st al (p r o du ct (3 ) ) wa s ob t a i n ed . (S c h eme 3)
1
HN M R sp e c tr u m w as me asu r ed ab o u t ea ch p r od u c t .
S C HEM E 1
S C HEM E 2

1
4=[ 29 2]
M. Konishi et al.
S C HEM E 3
S C HEM E 4
Differential Scanning Calorimetry (DSC) and Polarization
Microscograph
DS C wa s me a su r ed w it h S e ik o in st r u men t s DS C 22 a t a h e a t in g r a t e of
ꢀ
2 C =mi n by us e o f al u min u m p an . Th e mea su r emen t s we re r ep ea t ed
se v e r a l t ime s .
Th in fi lm s pr e p ar a t io n w as ca r r ie d o ut as f o ll ow s. E ac h BS A d er iv a t iv es
wa s he a te d a nd m elt . I t w as sa ck ed in b et w een t wo gla ss p la t es b y c ap il -
la r it y. Th e t em pe r at u r e w as ca r ef u lly co n t r ol led b y Me t tl er Tole d o FP82 H T
ꢀ
a t a r oun d t he me lt in g p oi nt an d gr a du a l ly lo w er ed a t t h e r a t e of 0.1 C =min .
Th e fi lm s we r e ob s er v ed u sin g a p ol a r iz at io n mic r osc o p e wit h a v ar i a b le
te mp e r a tu re ho t st ag e u nd e r cr o ssed n i co l co n d it ion .
Th e po la r i z e d ab so r p ti on sp e ct r a w er e mea su r ed on t h e h ot st a ge t o
me as ur e di c hr o ic r at io . L in ea r ly p ol ar iz ed li gh t wa s ir r a d iat e d t o t h e f ilm
a n d t he t ra n smi ssi on w as d e t ec te d. Th e an g le of t h e p ola r iz er, wh ic h ga v e
ꢀ
th e we a k e st t ra nsm i ssi on , w as d ef in ed as 0 .
Fourier Transform Infrared Spectroscopy (FT-IR)
FT-I R sp e ct r a w er e me a su r ed in Bi o- r ad FT S 60 00 wit h a n u n p ola r iz ed
in ci de n t be a m pe r p en d icu la r t o t h e sa mpl e f ilm p la n e . Th e BS A f ilms we r e
p r e pa r e d on K Br cr y st al p lat e s in st e ad o f gl asses a n d t h e mea s u r emen t
c ar r ie d ou t un de r co n t r o lle d t emp er a t u re b y C h in o D B10 00.

Giant Domain Formation in a Thin Film
15=[ 293]
F IGU RE 2D S C c u rv e s of B S A s (t h e s e co n d. h e a t ing )
RESULTS AND DISCUSSIONS
Thermal Property
In t he DS C me a su r eme nt s, BS A1 0 , 1 2, 1 3, 1 4, 15 , 16 , 18 , 20 sh o we d t wo
e n do th e rm i c pe ak s (Fi g. 2 ). Th os e p ha se w hic h in d ic at e t h at t h er e a r e
two ph a se s ( K1 , K2 ) b ef o r e iso t r op ic me lt in g. E ve n in t h e meso p ha se
b e tw e e n t wo pe a k s , it sh ow ed n o f lu id it y. Fig u r e 3 sh ow s t h e d ep en d en c e
o f ph a se t r a nsi t io n t em p er a tu r es o n t h e ch ai n le n gt h , n . Th e t emp er a t u r e of
K 1- K2 ph a se t ra n sit io n , w as ch an g e d li ne ar l y a lon g wit h a sol id lin e in
n ¼ 10 , 12 , 14 , 1 6, 1 8, 2 0 o r al o ng w it h a d ot t ed lin e in n ¼ 13 , 15 . Th is
o d d -e v e n e ffe c t s ug ge st s t h e d ir ec t io n o f t h e c h ain - en d c ou ld a ff e ct t h e
tr an si ti on be h a v i or. S in ce t h e f ilms h ave b ee n r ev ea led t o t a k e la yer st r u c-
tu r e wh e re t he ch ai n - en d s ar e f aci ng ea ch o th er, t h e c h ain - en d d ir ec t ion
m a y pl a y a n i mpo r t an t r o le f or in t e r la ye r in t er a c t ion .
0
Th e B SA 17 sh ow ed t h re e p ea ks; an o t he r p h ase (K2 ) wa s ob ser v ed
b et w e e n t he K 1 an d t h e K2 p ha se. S in ce it ma y b e c au se d b y imp u r it ies,
th e r e c ry s t a ll i za t io n w as r ep e at e d se ver a l t im es a n d t h e p u r it y wa s c h eck ed
1
b y HNM R a nd H PL C . N o sig n o f imp u r it ie s d et ec t ed . A b o u t BS A 6 10 , n o
p h a se wa s sh own f r om o ne cr y st all in e p ha se t o iso tr o p ic p h ase , ev e n if it
ꢀ
lo w e r e d t emp e r a tu r e t o ꢁ1 00 C, t h ou gh t h e meso p ha se of BS A 6 10 wa s

1
6=[ 29 4]
M. Konishi et al.
F IGU RE 3 Th e de p en d e nc e of p ha s e t r a ns it ion t e mp e r a t u r e on t h e c h a in le n g t h, n .
e x pe c te d t o be l ow er e d t o r o om t em p er a tu r e . I t sh ou ld b e c on c lu d ed t h at
th e br a nc h ed B SA h as n o me sop h a se as t h e BS A s wit h sh or t er c h ain len g th
(n < 10 ) .
Th e g i an t a ni s ot r o pi c d oma in s ap p ea r e d at t h e t r a n sit ion t emp er a t u r e
fr o m I t o K 2 ph ase u nd e r p ol a r iz ed mic r o sco p e . Mo r eo v er, wh en t h e t em -
p e r a tu r e wa s l ower e d mo r e gr a d ua lly, it w as o b ser v ed t h at a n u cl e a r in t o
a n mm -s ca l e mon o - do ma i n (Fi g. 4 ). At t h e K2 -K 1 t r a nsi t io n t em p er a t u re ,
th e a ng l e of t he p ol ar iz er w hi ch ga ve t h e d ar ke st ima ge of t h e d oma in
u nd e r t he c r osse d n ic o l co n d u ct io n ch an g ed in 8 d egr e e, a n d some c r a ck
a p pe a r e d i n t he f ilm. Th e ax is o f t h e r ef r ac t iv e in d ex ell ip so id of t h e BS A
F IGU RE 4P olar iz a tio n m ic rog r a p h of B S A 16 film u n d er c r .o s s e d n ic ol

Giant Domain Formation in a Thin Film
17=[ 295]
F IGU RE 5T em pe ra t u r e d ep e n de n c e of F T - IR s p e ct r a (B S A. 14 film )
fi lm mov e d a nd t he d oma in sh r un k at K1 - K2 p ha se t r a nsi t io n . O n t h e ot h er
h a nd , B SA 6 10 fi lm b ec ame t u r b id , w hi ch in d ica t es mic r oc r yst a lli n e f or m a -
tio n , a t t he t r a nsi ti on t emp er a t ur e f r om t h e iso tr o p ic t o t h e c r yst a ll in e
p ha se a s B SA s of sh or t ch ai n (n < 1 0) .
Th e FT-I R sp e ct r a o f BS A f ilms sh ow ed sig n if ic an t t emp er a t u r e d ep en -
d e nc e ( Fig . 5) . T he ab so r p ti on p ea ks as cr i b ed in a n ti sym met r ic V (CH )
a nd sy mme t r i c V (C H ) st r e t ch in g vi b r at io n ap p ea r e d a r ou n d 29 19– 29 26
as
2
s
2
ꢁ1
a nd 28 51– 28 55 c m r es pe c t ive ly.
Th e pe a k po si t io n p lo tt e d ag ai nst t h e t em p er at u r e a r e sh ow n in Figu r e 6.
B ot h t he V ( CH ) an d V (C H ) vi br at io n f r eq u en c ies we re ob se r v ed a t
a s
2
s
2
ꢁ
1
a r o un d 29 20 a nd 2 85 1 cm at K1 p ha se, wh ic h c or r esp o n d in g t o a n
a l l-t r a ns c onf or mat i o n [ 10 ]. Wh il e b ot h sh if t ed t o h igh er f r eq u en c y a t K2
F IGU RE 6 Tem per a t u r e d ep e n de n c e of t h e C H
fr eq u en ci es .
2
s t r e t c hin g a b s or p t ion b a n d

1
8=[ 29 6]
M. Konishi et al.
F IGU RE 7 Tem per a t u r e d ep e n de n c e of t h e C - O -C s t r e t c hin g a b s or p t ion b a n d
fr eq u en ci es .
ꢁ
1
p ha se ( at 29 22 a nd 2 85 3 cm r es pe c t ive ly ), in d ic a t in g t h e ga u ch e c on f or-
ma ti on c ont e nt be co me la r ge r. Bo t h sh if t ed t o f ar h igh er a t t h e I p h ase (a t
ꢁ
1
2
9 25 a nd 28 54c m
d iso r de r e d st a te [ 10 ,1 1] .
r es pe ct iv ely ), in d ic at in g a ll a lkyl c h ain s a r e in a
ꢁ
1
In t he sp ec tr a a t th e K2 p ha s e, a s ma l l p ea k w a s o bse rv ed a t 3 00 0 c m ,
w hi ch c a n b e as c ri b ed to ol ef in i c C H s tr e tc hi ng v ib ra tio n. I t is sug ge sti ng th a t
th e o r ie nta tio n o f ol ef in h ydr o car bo n b on d s in t he a ro m ati c c o re as c han ge d
at t h e K1 - K 2 p h as e tr an s itio n . Th e p e ak a ro un d 1 2 5 0 cm a s cr ib e d t o C-O -C
st r e tch i ng vi bra t io n s ho ws sig ni fi c a nt te mper a tur e d epen d ence (F i g . 7 ). It
shi f te d t o h i gh e r fr e que ncy at t he t r an sit io n fr o m K 1 t o K2 pha se , b ut s hi fte d
re ve rse ly to lo w er fr o m K2 t o I . I t in dic ate s t hat th e e nv i ro nme nt al co ndi ti o n
ar o und C O bo nd wa s dr as ti c a ll y ch a ng ed a t the K 2 phas e. Pro ba bly CO bo nd
s h o u ld s u f f er s t ra ng er s tr e ss at K2 p has e t h an a t t h e ot h e r p h as es .
ꢁ
1
CONCLUSIONS
It ha s be e n r e v ea le d t h at t h e t h in f ilm h avi n g h igh ly or d er ed mol e c u lar
a rr a n g e me n t c a n b e p r ep ar e d f r om t h e BS As ot h er t h an BS A 6 10 b y t h e
si mpl e me l t pr o c ess. Th ey sh o w ed me sop h a se b ef or e melt in g .
Th e a lk y l c ha i n s t oo k al l- tr a n s co n fo r mat i on a t K1 p h ase , a n d t h e ga u ch e
c on t e nt i nc r e a s e d at K2 p ha se.
In t hi s st ud y, we co n c lu d e t h at t h e me sop ha s e sh ou ld b e in d isp en sa b le
fo r t he g i an t do ma in f or ma t io n . Th e f ilm at t h e K2 p h ase sh ow ed n o f lu id it y
a n d t he do ma i n siz e d id n ot ch an g ed at t h e t r a nsi t io n f r om K2 t o K1 .
M or e de t a il st u dy su ch as t emp er a t ur e d ep en d en t X -r a y c r y st a llogr a p h y
is r e qu ir e d for mak in g a co n c lu sio n w he t h er K2 is liq u id c r yst a llin e st a t e or
c ry st a ll i ne st a t e .

Giant Domain Formation in a Thin Film
19=[ 297]
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