· Æw Dielectric Spectrometer (Novocontrol GmbH, Model: CONCEPT 40)- DE F = DÓ ×, . l 89 ×, 2...
Transcript of · Æw Dielectric Spectrometer (Novocontrol GmbH, Model: CONCEPT 40)- DE F = DÓ ×, . l 89 ×, 2...
HWAHAK KONGHAK Vol. 41, No. 4, August, 2003, pp. 485-490
��� ��� ��� �� �� � ����� �� ��
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������� �����305-600 �� ��� �� 100
*����� �������136-709 �� ��� ��� 5� 1
(2003� 1 15! "#, 2003� 3 25! $%)
Influence of Fluorination on Surface and Dielectric Characteristics of Polyimide Thin Film
Soo-Jin Park†, Ki-Sook Cho and Sung-Hyun Kim*
Advanced Materials Division, Korea Research Institute of Chemical Technology, 100 Jang-dong, Yuseong-gu, Daejeon 305-600, Korea*Department of Chemical Engineering, Korea University, 1, 5-ka, Anam-dong, Sungbuk-gu, Seoul 136-709, Korea
(Received 15 January 2003; accepted 25 March 2003)
� �
� ����� ��� � ��� ��� ���� � � �� � ����� X-ray photoelectron spectroscopy
(XPS)� ��� � � !" #$�%&, '(·)*( ��+ thermogravimetric analysis (TGA)� ,-./0 � �� &
$�%1. � 2345, ��� ��6 ��� � + ��789� :; ��<9 =7�%>?, 45(>@ ��
� 5 AB�� ��� C��%1. D6 45� EFG ��7 ���� �HIJ (electron polarization)� C�
KL&, M ��� NO@ ," H�NO0 =7KP>@Q ��� � � ���� C�KR ST6 ,H@ UV6 W
>@ XYG1. Z6 � 23�� ��� ��� � � '(·)*( ��� M [\� E] ^+ W� #$_ ` ab1.
Abstract − In this work, the effects of fluorine treatment of polyimide thin film on surface and dielectric characteristics were
studied using X-ray photoelectron spectroscopy (XPS) and dielectric constant, respectively. And, their thermal and mechanical
properties of the polyimide film were characterized by thermogravimetric analysis (TGA) and tensile strength, respectively.
The fluorine content of the polyimide film was increased with increasing the amount of the treatment gas, resulting in decreas-
ing the dielectric constant of the film. It was explained that the replacement of fluorine led to the decrease of the local electron
polarization of polyimide, or to the increase of the free volume which can be attributed to the relatively large volume of flu-
orine. Nevertheless, the fluorination didn’t significantly affect thermal or mechanical properties of the polyimide film under a
mild condition in this system.
Key words: Polyimide, Fluorination, Dielectric Constant, Thermal Properties, Mechanical Properties
1. � �
������ �� �� �� � ������ ��� ���
-O-, -NH-, -CO- �� ���� �� �� !"� �#, $%� &
300oC' �(�)* � +,�- ./0 12 34�5 �67� &
12 89:�; /<� �=� >?@ �=[1-2]. �A �� B�
�� CDE ������ 9!·9 F �� GH, I, J�K, L*
MF NO, �PQRF NO, STU ��� �F�� �=.
EA VW�F�X�) YZ [� \] .^$��/� �� L*M
& 9 VW2 N ' �� !_`a �b� c d�- e�f ag
h � �� ILD (interlayer dielectric) B#� i !_' `a� j�
�k�/� �=. ILD B#� ��) 89l� mn �8� op, �
q� r��) st/�' uN, vp, :t st�w (cross-talk) �/,
xp, st�w �/� r�y*' z.� C �q�$/NP$ .,
{p, NP$ �q�$� .|}u & ~ �' �!� �: ., c
�� =�p, 9!·9 F GH��� �Q� � �� ���� r�;
��h � ��0 3�� r��� & �y* J�- h � �� ���
& ��!!, �s��, '���, �� ��F 9 �� �� �F .
�8�=[3-4].
�L��� 89l�� 89M, � Q*M' 9!�C d�- ��
� mn d� ��� �N� ��� ���� � ��@ ��
+ − moment��2 bQ�) ¡ 9 "' ¢£�$� ¤¥� ¦§
(polarization)̈ =. �©ª bQ 9 "' �$� «w B# Q'†To whom correspondence should be addressed.E-mail: [email protected]
485
486 ���� ���� �
+ − moment. ¦§�� ,*; 89l�¬� ®h � �=[5]. �A
89l- U�D� nC2 op, N�$*' �$, vp, 8Q¯
(free volume)' �$, xp, ¦§' ,* (polarizability); [ � �=
[6]. �A �°� !CDE ±Z� ILDB#� �N; ²8³´���
� ��' µ2 ¦§�5 ¶ 8Q¯� Cw 12 89:�; ·
� }�B#� i ��. j� ¸� ��/� �=. df 12 89
l, �� ��¹!"� �#� Cw ILD B#�) �����; �
F �Nº»� i ��. j� �k� ¼=[7-9].
�N� � =½ � ¾ �¢DE ¸= ¶ 9 ¿$*¾ �($
potential- ./� ��0, .� À2 9! Á�*; ./� �� =½
$ÂB5' LÃ�� Ä� ÅD=. �L��� �N�Æ! D�) B#
- Ç�h È �N� � �N¾ º»DÉ �� �m�Â��
conjugated bond� �N� 'w) Ê$¨=. �A �N� =½ �N
¾ �ÂDE �� a��, Ë Ì}�, �� 9!� d�, �ST�,
�� �' d�- ��� Í Î2 �X�) �F��/� �=[10-12].
Ϭ) Ð ���)� �N$ Ç�� ' ����� GH' Ñd
�5 c� Ͻ 89l' �$; iÒDÓ=[13-14]. Ð °Ô�) Â�
¨ ��ÕÖV' ���$ ,*; Fourier Transform-IR (FT-IR); �
w iÒDÓ�0, �N$ Ç�� ' GH' Ñ & 89d�- XPS
¾ 89l ×,- �w ØCDÓ=. Ù ��·!"� d�2 TGA¾
C�Å* ×,- �DE �ÒDÓ=.
2. � �
2-1. ���� � ���
Ð °Ô� �F¨ dianhydride (3,3',4,4'-benzophenonetetracarboxylic
dianhydride; �D BTDA)¾ diamine (4,4'-oxydianiline; �DODA)2
Aldrich��) ÚV ÛÜM; Ý�Þ$ß�� ,U; DE �FDÓ=.
F� Aldrich�' N-methyl-1-pyrrolidinone (NMP, anhydrous quality);
�FDÓ�0, ÛÜM & FÄ' $% ��à- Fig. 1� ��á=.
�����' �N$ ÑÇ� �º� UµDE �FDÓ�0 �N�
F2 .â; �FDÓ=.
�����' 9�MC ��ÕÖV(polyamic acid; PAA) FI- Â�
D! Æw 3� ã¬âä; #N� purging å, NMP� diamine- æ
�� �ç' dianhydride; è9f æE 24³éê+ Lóë Â�DÓ
=. Â�¨ ��ÕÖV FI' �M#Ü�l2 15 wt%� �}DÓ=.
Â�¨ ��ÕÖV FI- substrate� �F¨ 8�ì Æ� applicator
(Sheen Instrument, S220403); �FDE í± îK' ïð. 50µm�
*ñ òâó å FÄ; za³ô! Æw 80oC�) 24³é ê+
prebakingDÓ=. Fig. 2� ��õ (*Û"� ��ÕÖV- ö$³ë
í± ����� îK- U� DÓ�0, ö$ Û"÷ $%��à- Fig. 3
� ��á=.
U�¨ ����� GH Ñ� �S �N$ Ç�D! 9� ����
� GH- øùú ^�) ûÁü ýþ!; �Fw ýþ å GH' ÿ
E��- U�D! Æw ���) Dk�: ��³ë) �FDÓ=. �
���� GH- �N$ ÑÇ�D! Æw �� #N.â� fluorination
reactor line- purging å <� boat� GH- �� reaction tube� <
� boat; �TDÓ=. <� boat; �- ³ reaction tube� [�.� V
N¾ ��- U�D! Æw =³ #N.â� purging =Á reaction
line- r9Ý���� 10−2 torr/ J!³=. GH- ÑÇ�D!
Æw reaction line� �N.â; 0 kPa(�D F0), 5 kPa(F5), 10 kPa(F10),
30 kPa(F30), 50 kPa(F50) ���� � DE �N .âÜ- �}DÓ
�0, :(�) 10� ê+ Ló� å r9Ý���� �� >k��
�- �5³ë 10−2 torr/ J!³=.
Fig. 1. Chemical structures of dianydride, dianiline, and solvent.
Fig. 2. Heating cycles for thermal imidization of polyamic acid.
Fig. 3. Preparation of polyimide via polyamic acid precuror solution.
���� �41� �4� 2003� 8�
�� �� ������ ��� 487
2-2. �� ��
Ð °Ô�) Â� �����' ���$ ,*; ØCD! Æw �
�ÕÖV FI5 ö$¨ ����� GH- KRS-5 reflection element
. QT¨ Digilab FTS-165 spectrometer; �Fw) wave number
4,000-400 cm−1' FT-IR â����� ��DÓ=.
2-3. �����
U�¨ GH- �N$ Ç�� Ͻ ����� GH' $%� ��2
XPS (ESCALAB MK-II); �DE ��DÓ�0, XPS ×,� �F¨
X-ray source� Mg Kα; �FDÓ�0, chamber' ��2 10−1-10−9
torr� �}DÓ=.
2-4. �� � ��� ��
����� GH' �N$ Ç� 9·å' 8�9�(*' �$� DSC
(Dupont 9,900: model 2,910); �FDE Þ(^* 10oC/min�� :(
�) 400oC/ ×,DÓ�0, �� d�' �$� #N�Æ! D�)
Þ(^* 10oC/min�� :(�) 800oC/ TGA (Dupont 9,900:
model 2,950); �FDE ×,DÓ=.
�N$ Ç�� Ͻ ����� C�Å*� �O� ³Ô!(Universal
Testing Machine, Lloyd LR5K); �FDE ASTM D412� �DE ³
¦- UµDÓ�0, cross head speed� 50 mm/min�� ×,DÓ=. ×
,�2 ��' ³¦� «DE 10r� ×,DE c ���- �FDÓ=.
2-5. �� ��
Ð °Ô�) �N$ Ç� 9·å' ����� GH' 89l �$;
×,D! Æw Dielectric Spectrometer (Novocontrol GmbH, Model:
CONCEPT 40)- �FDE ×,DÓ=. 89l ×, ��2 :(�)
�ü�; 101 HzQ� âò� �à�� 106 Hz/ �$³ôÑ) 89
l- ×,DÓ=.
3. �� �
3-1. �� ��
Fig. 4� �����' ���$ ,*; ØCD! Æw ��ÕÖV5
ö$�,- �� U�¨ ����� GH' FT-IR spectra �5�=. �
L��� ���KV' ���$ ³ =Á5 �2 ï Û"' �,- �
¿=. op, ï ÛÜM; FÄ� æ�Ñ BTDA' ��. ��Ñ) ODA
¾ `»m LÃ� ��� ��ÕÖV FI- Â�DÉ ¨=. vp, ̀
»mÂ� 'w Ú�¨ B� . �� 'w za��, ï ÛÜM� .¢
; �k� �����' �� ���$. ±��� Ý=[15].
�A 5,��Q� ��ÕÖV FI' FT-IR spectra; ��� Fig. 4(a)
; iÒDÑ, c��) ¸� �¾ �� `»LÃ� ' ��ÕÖV F
I' d� ¯äC � !³V' O-H (3,400-2,400 cm−1)¾ Õ"��'
N-H (3,500-3,100 cm−1); ØCh � ��0, dianydride' C=O (1,660,
1,535 cm−1)¾ C6H5' C=C (1,513 cm−1)� ' ¯ä. ��õ #-
ØCh � �á=[6, 16].
LÑ ��ÕÖV FI- 80oC�) 24³éê+ FÄ; za³ô�
prebaking �,- �¿ å 50oC�) 290oC/ Û"÷ ö$�,- �
¿ ����� GH' FT-IR spectra; Fig. 4(b)� ��á=. Ð °Ô
�5, ��ÕÖV�) ��õ O-H (3,400-2,400 cm−1)¾ N-H (3,500-
3,100 cm−1). $ÂLÃ� 'w B� ; Ú�³ô� �� 'w ���
$. Ý%�Ñ) ¯ä. �¬Ý #- ØCh � �á�0, �A 5,
�� Cw Ú�¨ ��� �� (725 cm−1); iÒh � �á=. Ù ,
���' 9P�C d�¯äC C=O (1,780, 1,720 cm−1), C-N (1,370 cm−1)
c�� (OC)2NC (1,100 cm−1)� ' ¯ä. Ú�¨ #- iÒh �
�á�0[6, 16], �A �5�Q� ���$. 100% Ý%�áÁ- Ø
Ch � �á=.
3-2. �����
�N$ Ç�9·å' ����� Ñ' i! ��- ýf &'¸
! ÆDE ����� GH' XPS spectra; Fig. 5� ��á=. c
�5 �Ç� �����' ö� �Â�(/ 285 eVQY�) ùN ¯ä,
404 eVQY�) #N¯ä c�� 532 eVQY�) VN ¯ä. ��õ
#- ØCh � �á=. LÑ �N$ Ç� ö� 694 eV QY�) �
N ¯ä. )*É ��+�0, �NÇ� .â��� z.h�ñ, � Ç
� .âÜ� z.h�ñ �����' �N ¯äý!. z.D� #-
iÒh � �á=. �A �����' $%��- Table 1� ���
�5, �N$ Ç�� 'w �����' ùN, #N, VN' ²Ü2 Ç
�.â ��� Ϭ uND� LÑ, �N' ²Ü2 z.D� #- ØC
Fig. 4. FT-IR spectra of polyamic acid and cured polyimide thin film.
Fig. 5. XPS survey scan spectra of polyimide thin film.
Table 1. Chemical composition of polyimide thin film
C1S N1S O1S F1S F1S /C1S
F00F50F10F30F50
69.755.056.049.549.1
10.308.05.74.64.7
20.024.021.716.013.0
013.016.629.933.2
023.629.660.467.6
HWAHAK KONGHAK Vol. 41, No. 4, August, 2003
488 ���� ���� �
h � �á=.
�L��� �N� � =½ � ¸= ¶ 9 ¿$*¾ �($
potential- ./� ��0, .� À2 9! Á�*; ./� ��,�
=½ $ÂB5' LÃ�� Ä� ÅD=. df F2 .â� LÃ�� -)
.^- ʲ «Q�' $ÂB5 LÃD0, df ùN$ÂB5� Ía
��� LÃD0 LÃ�- aÚ³�=. 5* LÃ�� aÚ�Ñ (*
:Þ�� Cw C-C �Â� �w��� \ äÉ � =� >?@ �
=[10-12]. �, �N�Æ! D�) B#- ÑÇ�DÑ B# Ñ' �
+, �Â� /�/� LÃ�� À2 ¬01� Ú��� �N¾ º
»DÉ �0, �m�Â�� conjugated bond� �N� 'w) Ê$ ¨
=� >?@ �=[12]. cA,� ����� GH Ñ� �N; ²8
µF!; 2 \ :ýf ��D! Æw) XPS carbon 1S core level
scan spectra� ��' !#- �¢ ��DE Fig. 6� ��á=.
Ð °Ô�5, �N$ Ç�D/ 32 ����� GHC Fig. 6(a)' ö�
284.6 eV (C=C), 285.6 eV (C-N), 286.2 eV (C-O-C) c�� 289.2 eV
(C=C)�) �����' 9P�C d�¯ä; ØCh � �á=. �N
$ Ç� ö� �����' �Nº»� 'w Fig. 6(b)¾ (c)�) )
*É 288.7 eV (C-F)¾ 291.1 eV (CF2)' ̄ ä. Ú�¨ #- ØCh � �
á�0, Ù Fig. 6(d)¾ (e)' ö� 288.7 eV¾ 291.1 eV�b� 290.5 eV
(CF2 in trifulorobenzene)�) ¯ä. Ú�¨ #- iÒh � �á=. �
A �5� F2.â; �FDE ����� GH- �N$ Ç� ³ :
!�) 45 �N' Là ø-<65 �� �����¾ �N� '
LÃ�� C-F Ù� CF2 �Â�� ������ º»¨ #- ØCh �
�á=. Ù Fig. 6(d)¾ (e)�) 7 � �ª� �N.â ��� 30 kPa
�:C ö��� ������ º»¨ �N²Ü� äÉ z.DE C=C
¯ä¸= C-F ̄ ä. \ äÉ a8D� �5; ��á�0 �È'
F1S/C1S�. Table 1�) ØCh � �ª� �� 60.4%¾ 67.6%� =
½ GH' ö�� �w ¶ �- ��� #- iÒh � �á=.
3-3. �� � ��� ��
�N$ Ç�� Ͻ �����' DSC9�- Fig. 7� ��á=.
c �5, �� �����' Tg (glass transition temperature). 283.6oC�
Fig. 6. High resolution C1S XPS spectra of polyimide thin film with fluori-nation concentration; (a) F0 (b) F5, (c) F10, (d) F30, and (e) F50.
Table 2. Mechanical properties of polyimide thin film
Tensile strength [MPa] Ultimate elongation [%]
F00F50F10F30F50
116±10.7115±13.5115±11.0118±14.5118±12.3
33±4.334±3.132±2.938±4.537±3.2
���� �41� �4� 2003� 8�
�� �� ������ ��� 489
��+�0 �N$ Ç� ö� F50' Tg. 282.7oC� uN �5;
ØCh � �á=. �L��� Tg� :�- �º� C �) � Ü, �
mÂM, �,$*, $%� ��, �� �� ��0, �A C [' �
$� Cw �� ' 8Q¯. z.DÑ c :�� 'w Tg. uN
=� >?@ �=[17]. :! XPS �5�) �Ò �¾ ��, ���
��� º»¨ �N� ' Q¯. �N� ùN¸= ä! È;� ��
' 8Q¯; z.³´��� Fig. 7�) ��õ �¾ �� Tg. u
N #�� ìÛ¨=.
Fig. 82 �����' TGA9�- ��� �5�=. �A TGA9
���Q� Table 3� IDT (initial decomposition temperature); ��
á=. c �5, F0' ö� IDT. 555oC� ��+�0 �N$ Ç�
ö� F5¾ F10' ö� ¶ ��; ��/ 3<�� F30' ö� =N
uNDÓ�0 F50' ö� û! ��w `³ (*. äÉ uN #-
ØCh � �á=. �L��� ������ �� �� � ����
�� ��� ��� -O-, -NH-, -CO- �� ���� �� �� !"
� �# & 300oC' �(�)* � +,�- ���=� >?@ �=
[1-2]. cA� 5Ü' �N¾ LÃ�� Cw :! �NLà ø-<6�
) 45DÓª� �����' � �� � �Â� =�/Ñ) F50
' º»¨ C-F ̄ ä. äÉ z.�� �� Cw û! ��w (*. ä
É uN #�� ìÛ¨=[6, 16, 18]. cA� F50- Ub =½ ��
���' ö�, �N$ Ç� ³ �N²Ü� 30% �D� º»¨ ���
��� �NÇ�� 'w � +,�� ¶ :�- �º/ 3/� �N²
Ü� 30% �:C �����' ö� � +,�� =N uN #- i
Òh � �á=.
�N$ Ç� 9·å' ����� GH' C�Å*(tensile strength)¾
üÛ sl(ultimate elongation)- Table 2� ��á=. Ð °Ô�5 �
Ç� �����C F0' C�Å*� 116 MPa, üÛ sl2 33%�
��á�0, �N$ Ç� ����� GH' ö� �Ç� GH'
�5 �¢DE ¶ �$; ��/ 32 #- ØCh � �á=. �A
�5� �S �N$ Ç�� 'w ������ * ¨ �N. ��
���' !"� B��� ¶ :�- �º/ 32 #�� ìÛ¨=
[6, 9, 19].
3-4. �� ��
89d�2 (* & �ü�� Ϭ c J�' ±£ & ®:� 8¬Ý
=� >?@ �=[5]. Ð °Ô�)� �NÇ� 9·å �����' 89
l- :(�) �ü�; 101 HzQ� 106 Hz/ �$³ôÑ) ×,D
Ó�0 c �5; Fig. 8� ��á=. Ð °Ô�5, �Ç� ����
�C F0' ö� 89l� �ü�>Æ� Ϭ 3.1-2.9��' �Ê; ¸
Ó�0 ×, ���� 3.04� 9P�C �����' �- ��á
=[13-14]. cA� �N$ Ç� GH' ö� :! Ñi! �5�
) �Ò �¾ �� Ç�.â ��� z.DE * ¨ �N²Ü� z
.h�ñ �5��� GH' 89l� uND� ö�- iÒh � �
á=. �, ×,¨ �ü� >Æ�) 89l ���� F5=2.99, F10=2.68,
F30=2.67 c�� F50=2.55� ®Ëf uN #- ØCh � �á=.
:! )?�) 45 �¾ �� 89l2 N�$*, 8Q¯, ¦§
�' ý ./ nC� äÉ :�- @�0 N�$*¾ ¦§�5� �A
D0 8Q¯¾� L�A =[6, 8-9]. Ð °Ô�) GH� �S �N
$ Ç�; ²��� * ¨ �N� Cw ����� � �� �
8Q¯� z.D� ¦§�2 uNDE �5��� 89l� uN #
�� ìÛ¨=. �A �8� op, DSC�5�) �Ò �¾ �� �
N$ Ç�� 'w ������ º»¨ �N� . �����' �
�� � 8Q¯; z.³ë 89l� uN #�� iÒ¨=[20].
vp, 9 . B�) C� D�@ �� � � 9 . B� ÅDÉ E
� �� � ¸= \ FÉ ¦§D,� 9 [� B� �G ÛÛDÉ E
��� �N� ' ¦§�2 µ=. Ù , ù$�N� �2 � Ü- .
Fig. 7. DSC diagrams of polyimide thin film.
Fig. 8. TGA thermograms of polyimide thin film.
Table 3. Thermal stability parameter of polyimide thin film
F0 F5 F10 F30 F50
IDT [oC] 555 549 550 533 395 Fig. 9. Dielectric constants of polyimide thin film.
HWAHAK KONGHAK Vol. 41, No. 4, August, 2003
490 ���� ���� �
i-
ri-
nd
on
i-
lu-
,”
ak-
ing
on
bon
t on
s;
yn-
vel
ub-
of
,
es
ohn
Ý ù$�N¾ �¢h È Ä� Hb��� I�J� 1�0 �A �
8� K) 45 «� �N� � Ä� 12 ¦§� È;� van der
Waals C�� Õ� µÕ/! È;�=. cA,� C-F �Â' 9 ¦§
� C-H �Â� �¢DE ¸= µ! È;� �N$ Ç� �����
' 89l� uN #�� ìÛ¨=[20].
4. � �
���)� ILD (interlayer dielectric) B#� L� �F�� ��
���' 89l- uN³ô! Æw �N$ Ç�DE GH' Ñd�
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