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7/31/2019 Leclere Oral Session 5
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White Light EmittingWhite Light EmittingSupramolecularSupramolecular PolymersPolymers
PhilippePhilippe LECLERELECLERE
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Recent challenge: towards lighting Recent challenge: towards lighting
IntroductionIntroduction
Philips
Siemens
UDC
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IntroductionIntroduction
http://www.oled-display.net/oled-lighting
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IntroductionIntroduction
How toHow to produceproduce white light ?white light ?
MixingMixing of of threethree REDRED,, GREENGREEN, and, and BLUEBLUEemittingemitting chromophoreschromophores
Blends
Multilayers
Block Copolymers Quantum dots
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IntroductionIntroduction
SupramolecularSupramolecular PolymersPolymers
o o a ggrega evan der Waals interactions Covalent bonds
Supramolecular PolymerNon-covalent interactions
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SupramolecularSupramolecular Polymers Polymers
TwoTwo approachesapproaches ......
SupramolecularSupramolecular polymerpolymer chainchain
SupramolecularSupramolecular oligomeroligomer stackstack
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Quadruple HydrogenQuadruple Hydrogen- -Bonded UnitBonded Unit
NN
O
N HH
RN
N
NH HC
NHO
R
R'
SupramolecularSupramolecular PolymersPolymers
C N HO
R'O
Intramolecular H-bond
Intermolecular H-bonds
Science, 278, 1601 (1997)J. Polym. Sci., Part A: Polym. Chem. 37, 3657 (1999)Chem. Comm. 1847 (1998)
UreidopyrimidinoneUreidopyrimidinone ( (UPyUPy))
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SupramolecularSupramolecular PolymersPolymers
FirstFirst ApproachApproach
NN
O
N HHC
N HO
R
R'
NN
O
NH HC
NHO
R
R'
RR RRUPyUPy
HH -- bondingbonding
MixingMixing
UV Excitation
n m p q
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SupramolecularSupramolecular Polymers Polymers
PerylenePerylene - - PERYPERY
M.M. PouderoijenPouderoijen
para para --PhenylenePhenylene vinylenevinylene OPV5OPV5
FluoreneFluorene F3F3
Ch. GrenierCh. Grenier
R.R. AbbelAbbel
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Purification by recycling GPCPurification by recycling GPC
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SupramolecularSupramolecular PolymersPolymers
In SolutionIn Solution
0.50
0.75
1.00
r m .
P L i n t .
0.50
0.75
1.00
r m .
A b s .
0.50
0.75
1.00
r m .
P L i n t .
0.50
0.75
1.00
r m .
A b s .
Absorption Photoluminescence
400 500 600 700 800
0.00
0.25 n o
(nm)
300 400 500 600 700 800
0.00
0.25
n
(nm)
400 500 600 700 800
0.00
0.25 n o
(nm)
300 400 500 600 700 800
0.00
0.25
n
(nm)
n
n
nPERYF3
OPV5
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SupramolecularSupramolecular PolymersPolymers
InIn SolidSolid StateState
0.50
0.75
1.00
r m .
P L i n t .
0.50
0.75
1.00
r m .
A b s .
0.50
0.75
1.00
r m .
P L i n t .
0.50
0.75
1.00
r m .
A b s .
Absorption Photoluminescence
400 500 600 700 800
0.00
0.25 n o
(nm)
300 400 500 600 700 800
0.00
0.25
n
(nm)
400 500 600 700 800
0.00
0.25 n o
(nm)
300 400 500 600 700 800
0.00
0.25
n
(nm)
n
n
n
OPV5
F3 PERY
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SupramolecularSupramolecular PolymersPolymers
InIn SolidSolid StateState
nn
= 0.783 nm= 0.783 nm = 0.452 nm= 0.452 nm
SmoothSmooth surfacessurfaces
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SupramolecularSupramolecular PolymersPolymers
InIn SolidSolid StateState
0.25
0.50
0.75
1.00
E L i n t . n o
r m .
ITOPEDOT:PSS
emissive layerAl
nOPV5
nF3
nPERY
400 500 600 700
0.00
0.25
0.50
0.75
1.00
1.25
P L i n t . ( a r b . u
n i t s
)
((((nm )
400 500 600 700
.
(nm)
Glass
W.W. StouwdamStouwdam
85 : 10 : 5
exc = 365 nm
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SupramolecularSupramolecular PolymersPolymers
InIn SolidSolid StateState 8585 :: 1010 :: 55
= 0.754 nm= 0.754 nm
No phaseNo phase separationseparation
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SupramolecularSupramolecular OligomerOligomer StackStack
SecondSecond ApproachApproach
FFF =FFF = FluoreneFluoreneFNF =FNF = NaphtaleneNaphtaleneFQF =FQF = QuinoxalineQuinoxalineFBF =FBF = BenzothiadiazoleBenzothiadiazole
FTF =FTF = ThienopyrazineThienopyrazine
FFF FNF FQF FBF FTF
R. Abbel
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5
1.5x10 5
C12-F1-C12C12-F3-C12C12-FNF-C12
a b
5
1.5x10 5
C12-F1-C12C12-F3-C12C12-FNF-C12
a b
SupramolecularSupramolecular OligomerOligomer StackStack
Absorption Photoluminescence
F1F1F3FNF
300 400 500 600 7000.0
5.0x104
.C12-FQF-C12C12-FBF-C12C12-FTF-C12
( M - 1 c m -
1 )
(nm)
400 500 600 700 800
P L i n t
.
(nm)300 400 500 600 700
0.0
5.0x104
.C12-FQF-C12C12-FBF-C12C12-FTF-C12
( M - 1 c m -
1 )
(nm)
400 500 600 700 800
P L i n t
.
(nm)
R. Abbel
FQFFBFFTF
Small changes Small changes bigbig effectseffects on the photoluminescenceon the photoluminescence propertiesproperties
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MolecularMolecular ModellingModelling
FFF
FTF
DreidingDreiding Force FieldForce Field M. Surin
FNF
FBF
FQF
FNF FFF, FQF, FBF, FTFFNF FFF, FQF, FBF, FTF
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SupramolecularSupramolecular OligomerOligomer StackStack
FFFFFF
2.0 m 300 nm
HeightHeight = 4.3 nm= 4.3 nm
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Annealed @ 125C
SupramolecularSupramolecular PolymersPolymers
ExtrudedExtruded filamentfilamentFFFFFF
30C
W. PisulaLamellarLamellar organizationorganization perpendicularperpendicular to the filament axisto the filament axis
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MolecularMolecular ModellingModelling
SupramolecularSupramolecular OligomerOligomer StackStack
M. SurinPeriodicPeriodic BoundaryBoundary ConditionsConditions
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Hierarchical OrganizationHierarchical Organization
FFFFFF
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OrganogelsOrganogels
Spin coatingDrop Casting
FTFFTF
2.0 m400 nm
MCHMCH
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OrganogelsOrganogels
FFFFFF FTFFTF
MCHMCH
Gel
Sol
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White EmittingWhite Emitting OrganogelsOrganogels
exc = 375 nm= 375 nm
FFF : FQF : FBF : FTF4.47 : 0.65 : 0.23 : 0.1 mM
POMPOM AFMAFM
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SupramolecularSupramolecular approachapproach c combinesombines the purity of the purity of oligomersoligomers with thewith the processabilityprocessability of polymers :of polymers :
Self Self--complementarycomplementary UPyUPy group equippinggroup equipping chromophoreschromophores; ; --stacking and Hstacking and H- -bonding.bonding.
ThisThis modularmodular a roacha roach isis aa romisinromisin a roacha roach toto
SummarySummary
createcreate multicomponentmulticomponent systemssystems. . EasyEasy toto processprocess and noand no macrophasemacrophase separation isseparation is
observed.observed.
ColorColor tuningtuning by simpleby simple mixingmixing of chromophores.of chromophores. MechanismsMechanisms of (whiteof (white- -lightlight emittingemitting) ) organogelorganogel
formation.formation.
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AcknowledgementsAcknowledgements
Service de Chimie des Matriaux Nouveaux
Universit de MonsMons (Belgium)
M. Surin
R. Lazzaroni
Eindhoven University of Technology
Eindhoven (The Netherlands)
R. Abbel
Ch. GrenierW. StouwdamM. PouderoijenA.P.H.J. Schenning
E.W. Meijer
Max Planck Institute fr PolymerforschungMainz (Germany)
W. Pisula
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AcknowledgementsAcknowledgements
European Commission.
Belgian Federal Government Office of Science Policy.
Fonds National pour la Recherche Scientifique (FNRS, Belgium).
overnmen o e g on a onne.
Communaut franaise de Belgique.
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Thank you for attention !!Thank you for attention !!