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Supporting Information Efficient deep-blue electroluminescence with CIEy (0.05–0.07) from phenanthroimidazole–acridine derivative hybrid fluorophores Shuo Chen, a Jiarong Lian, a Weigao Wang, b Yue Jiang, a Xuedong Wang, c Shuming Chen, b Pengju Zeng,* ,a Zhengchun Peng* ,a a Key Laboratory of Optoelectronic Devices and Systems of Ministry of Education and Guangdong Province, College of Optoelectronic Engineering, Shenzhen University, Shenzhen, Guangdong, 518060, P.R. China b Department of Electrical and Electronic Engineering, Southern University of Science and Technology, Shenzhen, Guangdong, 518055, P. R. China c Key Laboratory for Carbon-Based Functional Materials and Devices Institute of Functional Nano and Soft Materials (FUNSOM) of Jiangsu Province, Soochow University, Suzhou, Jiangsu, 215123, P.R. China *Email - [email protected] Index Content Page No. Figure S1 1 H NMR spectrum of compound PhImBr. 1 Figure S2 1 H NMR spectrum of compound PhImAc. 1 Figure S3 1 H NMR spectrum of compound PhImEn. 2 Figure S4 HR-MS spectrum of compound PhImBr. 2 Figure S5 HR-MS spectrum of compound PhImAc. 3 Figure S6 HR-MS spectrum of compound PhImEn. 3 Figure S7 Absorption spectra of PhImAc and PhImEn in neat film. 4 Figure S8 Solvatochromic shifts of PL spectra of PhImAc (a) and PhImEn (b). 4 Figure S9 Phosphorescence spectra of PhImAc and PhImEn at 77 K. 5 Figure S10 TGA and DSC thermograms of PhImAc and PhImEn 6 Figure S11 Cyclic voltammogram of compouds PhImAc and PhImEn in the anode scan. 7 Figure S12 Energy level diagrams of the WOLEDs C and D 8 Figure S13 Performance of WOLEDs C and D. 9 Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is © The Royal Society of Chemistry 2018

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Page 1: Supporting Information · Supporting Information Efficient deep-blue electroluminescence with CIEy ∈ (0.05–0.07) from phenanthroimidazole–acridine derivative hybrid fluorophores

Supporting Information

Efficient deep-blue electroluminescence with CIEy ∈ (0.05–0.07) from

phenanthroimidazole–acridine derivative hybrid fluorophores

Shuo Chen,a Jiarong Lian,a Weigao Wang,b Yue Jiang,a Xuedong Wang,c

Shuming Chen,b Pengju Zeng,*,a Zhengchun Peng*,a

a Key Laboratory of Optoelectronic Devices and Systems of Ministry of Education and Guangdong Province, College

of Optoelectronic Engineering, Shenzhen University, Shenzhen, Guangdong, 518060, P.R. China

b Department of Electrical and Electronic Engineering, Southern University of Science and Technology, Shenzhen,

Guangdong, 518055, P. R. China

c Key Laboratory for Carbon-Based Functional Materials and Devices Institute of Functional Nano and Soft Materials

(FUNSOM) of Jiangsu Province, Soochow University, Suzhou, Jiangsu, 215123, P.R. China

*Email - [email protected]

Index

Content Page No.

Figure S1 1H NMR spectrum of compound PhImBr. 1

Figure S2 1H NMR spectrum of compound PhImAc. 1

Figure S3 1H NMR spectrum of compound PhImEn. 2

Figure S4 HR-MS spectrum of compound PhImBr. 2

Figure S5 HR-MS spectrum of compound PhImAc. 3

Figure S6 HR-MS spectrum of compound PhImEn. 3

Figure S7 Absorption spectra of PhImAc and PhImEn in neat film. 4

Figure S8 Solvatochromic shifts of PL spectra of PhImAc (a) and PhImEn (b). 4

Figure S9 Phosphorescence spectra of PhImAc and PhImEn at 77 K. 5

Figure S10 TGA and DSC thermograms of PhImAc and PhImEn 6

Figure S11 Cyclic voltammogram of compouds PhImAc and PhImEn in the anode scan. 7

Figure S12 Energy level diagrams of the WOLEDs C and D 8

Figure S13 Performance of WOLEDs C and D. 9

Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.This journal is © The Royal Society of Chemistry 2018

Page 2: Supporting Information · Supporting Information Efficient deep-blue electroluminescence with CIEy ∈ (0.05–0.07) from phenanthroimidazole–acridine derivative hybrid fluorophores

1

Figure S1. 1H NMR spectrum of compound PhImBr.

Figure S2. 1H NMR spectrum of compound PhImAc.

Page 3: Supporting Information · Supporting Information Efficient deep-blue electroluminescence with CIEy ∈ (0.05–0.07) from phenanthroimidazole–acridine derivative hybrid fluorophores

2

Figure S3. 1H NMR spectrum of compound PhImEn.

Figure S4. HR-MS spectrum of compound PhImBr.

Page 4: Supporting Information · Supporting Information Efficient deep-blue electroluminescence with CIEy ∈ (0.05–0.07) from phenanthroimidazole–acridine derivative hybrid fluorophores

3

Figure S5. HR-MS spectrum of compound PhImAc.

Figure S6. HR-MS spectrum of compound PhImEn.

Page 5: Supporting Information · Supporting Information Efficient deep-blue electroluminescence with CIEy ∈ (0.05–0.07) from phenanthroimidazole–acridine derivative hybrid fluorophores

4

300 350 400 450 5000.0

0.2

0.4

0.6

0.8

1.0

Norm

aliz

ed A

bso

rbta

nce

Inte

nsi

ty

Wavelength(nm)

PhImAc in film

PhImEn in film

Figure S7. Stead-state absorption spectra of PhImAc and PhImEn in neat film at room

temperature.

350 400 450 500 550 600 650

0.0

0.2

0.4

0.6

0.8

1.0

Norm

aliz

ed Inte

nsi

ty

Wavelength (nm)

n-hexane

Toluene

1,4-dioxane

Ether

Ethyl acetate

THF

DCM

DMF

(a)

350 400 450 500 550 600 650

0.0

0.2

0.4

0.6

0.8

1.0

(b)

Norm

aliz

ed Inte

nsi

ty

Wavelength (nm)

n-hexane

Toluene

1,4-dioxane

Ether

Ethyl acetate

THF

DCM

DMF

Figure S8. Solvatochromic shifts of PL spectra of PhImAc (a) and PhImEn (b).

Page 6: Supporting Information · Supporting Information Efficient deep-blue electroluminescence with CIEy ∈ (0.05–0.07) from phenanthroimidazole–acridine derivative hybrid fluorophores

5

400 450 500 550 600 650

0.0

0.2

0.4

0.6

0.8

1.0

0→2

0→1

Norm

aliz

ed Inte

nsi

ty

Wavelength (nm)

PhInAc

PhImEn

0→0

Figure S9. Phosphorescence spectra of PhImAc and PhImEn in toluene at 77 K.

Page 7: Supporting Information · Supporting Information Efficient deep-blue electroluminescence with CIEy ∈ (0.05–0.07) from phenanthroimidazole–acridine derivative hybrid fluorophores

6

200 400 600 80020

40

60

80

100

(a)(a)

0 50 100 150 200 250Temperature (C)

1 st Heat

2 nd Heat

Endo

Heat Flo

w (

J/g)

0 50 100 150 200 250

Heat Flo

w (

J/g)

Temperature (C)

1 st Heat

2 nd HeatEndo

140C

454C

Weig

ht Lo

ss (

%)

Temperature (C)

PhImAc

PhImEn

328C

(a)

(b)

Figure S10. TGA thermograms of PhImAc and PhImEn measured at 10 oC min–1 under

nitrogen flushing. Insert: DSC spectra of the first and second heating cyclings for

PhImAc (a) and PhImEn (b), at a heating rate of 10 oC min–1 under nitrogen flushing.

Page 8: Supporting Information · Supporting Information Efficient deep-blue electroluminescence with CIEy ∈ (0.05–0.07) from phenanthroimidazole–acridine derivative hybrid fluorophores

7

0.0 0.3 0.6 0.9 1.2 1.5

Potential (V)

PhImAc

PhImEn

Curr

ent

(a.u

.)

Figure S11. Cyclic voltammogram of compouds PhImAc and PhImEn in the anode scan.

Page 9: Supporting Information · Supporting Information Efficient deep-blue electroluminescence with CIEy ∈ (0.05–0.07) from phenanthroimidazole–acridine derivative hybrid fluorophores

8

Figure 12. Energy level diagrams of the WOLEDs C and D based on PhImAc and PhImEn

as host and PO-01 as dopant.

-10.0

-9.0

-8.0

-7.0

-6.0

-5.0

-4.0

-3.0

-2.0

-1.0

Energ

y level (e

V)

HA

T-C

N (

15

nm

)

6.0

9.0

ITO

4.85.3

HTL

2.0

TA

PC

(30 n

m)

Ph

ImA

c/E

n(3

0 n

m)

2.9

EML

Tm

PyP

B(4

0 n

m)

ELT

6.66

3.04

LiF/Al

4.3

PO

-01

Ph

ImA

c/E

n(3

0 n

m)

5.1

Page 10: Supporting Information · Supporting Information Efficient deep-blue electroluminescence with CIEy ∈ (0.05–0.07) from phenanthroimidazole–acridine derivative hybrid fluorophores

9

Figure S13. (a) Electroluminescence spectra for WOLED C. (b) Electroluminescence

spectra for WOLED D at different voltages. (c) Current density–voltage–luminance

characteristics. (d) Efficiency versus luminance curves.

200 300 400 500 600 700 800

0.0

0.2

0.4

0.6

0.8

1.0

Norm

aliz

ed Inte

nsi

ty

Wavelength(nm)

6 V

7 V

8 V

9 V

10 V

200 300 400 500 600 700 800

0.0

0.2

0.4

0.6

0.8

1.0

Norm

aliz

ed Inte

nsi

ty

Wavelength(nm)

6 V

7 V

8 V

9 V

10 V

(a)

(d)

(b)

(c)

0 2 4 6 8 10 12 140

200

400

600

800

Curr

ent

denst

iny (

mA

cm

-2)

Voltage(V)

Device C

Device D

100

101

102

103

104

Lum

inance

(cd

m-2

)

0

5

10

15

20

0

5

10

15

0 5000 10000 15000 200000

5

10

Device C

Device D

C.E

. (cd

A-1

)

P.E

. (lm

W-1)

E.Q

.E. (

%)

Luminance (cd m-2)