9H-Fluoren-2-aMine, N-[1,1'-biphenyl]-4-yl-9,9-diMethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-

Product Name9H-Fluoren-2-aMine, N-[1,1'-biphenyl]-4-yl-9,9-diMethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-
CAS1242056-42-3
MFC51H38N2
MW678.86
EINECS
MOL File1242056-42-3.mol

Chemical Properties

Melting point	155-156 °C
Density	1.14
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
form	powder
pka	-2.80±0.40(Predicted)
color	white to yellow
InChIKey	GJWBRYKOJMOBHH-UHFFFAOYSA-N
SMILES	[n]2(c3c(c%10c2cccc%10)cc(cc3)c4ccc(cc4)N(c8ccc(cc8)c9ccccc9)c5cc6c(cc5)c7c(cccc7)C6(C)C)c1ccccc1

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Chemical Properties

Off-white powder

Uses

N-([1,1μ-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine (BCFN) is an electron-rich material, with the HOMO energy level of 5.3 eV, the LUMO energy level of 2.2 eV and high hole mobility of 5.43 * 10-5 cm2V-1s-1. As a result, it is used as a hole-transport and hole-injection material in organic light-emitting diodes. BCFN has shown its advantages in improving the hole mobility of polymer-based hole transport layer; lower driving voltage of device, better efficiency, and higher EQE due to exciplex formation by utilizing in EML; and better device lifetimes in the combination of Ir(piq)2(acac) to act as an electron scavenger layer for an reported device.
BCFN is a good morphologically stable material with Tg of 125 °C and Td of 375 °C.
With a ET of 2.58 eV, BCFN is also a very good charge transporting layer material due to its large band gap (Eg = 3.1 eV) 2 for green, red and white phosphorescent organic light-emitting diodes (PhOLEDs).
OLED Device Performance:
BCFN increase the hole transport mobility of PVK (pure PVK: 2.09*10-9 V cm-1 S-1; 30% of BCFN in PVK: 9.86*10-7 V cm-1 S-1; 50% of BCFN in PVK: 1.15*10-5 V cm-1 S-1):
1. ITO/PEDOT:PSS (40 nm)/PVK:BCFN (3:7, 20 nm)/BCFN:PFO (x:1-x, 80 nm)/CsF (1.5 nm)/Al (120 nm)
Color: Blue

BCFN in combination of ET1 to act as EML in forming exciplex and improve device performance:
2. ITO/HIL/HTL/(ET1+P1) or (ET1+BCFN+P1(doped)/ETL/ LiF/Al
Color: red
Device emission area of 81cm2, and at 1000 cd m-2, the efficiency exceeds 200 lm/W and the EQE exceeds 50 %.
lifespan@95: from 71h to 133h
BCFN in combination with Ir(piq)2(acac) as electron scavenger layer:
3. ITO/NDP series in BCFN (3wt.%, 10nm)/BCFN(160nm) or BCFN(130nm)+BCFN:Ir(piq)2(acac)(2wt.%, 10nm)+BCFN(20)/ [Ir(TMSBppy)ppy2]:BPTZBC (10 wt.%, 40nm))/ TPBi:Liq (1:1 wt. % ratio, 36nm)/ Liq (0.1nm)/Al (60 nm)
Color: yellow
Efficiencies are not affected.
lifespan@95: from 71h to 133h', 'N-([1,1μ-Biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine can be used in different application areas as an emissive layer or hole transport layer due the presence of π-conjugated structure and electron-donating/accepting groups. It is suitable to be used in R&D studies such as organic field-effect transistors (OFETs), molecular electronics, sensors, organic photovoltaics (OPVs), and organic light-emitting diodes (OLEDs).

Synthesis

N-(4-biphenyl)-(9,9-dimethylfluoren-2--yl)Amine

897671-69-1

1028647-93-9

9H-Fluoren-2-aMine, N-[1,1'-biphenyl]-4-yl-9,9-diMethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-

1242056-42-3

General procedure for the synthesis of N-biphenyl-4-yl-9,9-dimethyl-9H-fluoren-2-amine from N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine and 3-(4-bromophenyl)-9-phenylcarbazole: 3-(4-bromophenyl)-9-phenyl- 9H-carbazole (9.6 g, 24 mmol) was dissolved in toluene and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (7.2 g, 20 mmol), tris(dibenzylideneacetonato)dipalladium (Pd2(dba)3, 0.05 equiv.), triphenylphosphine (PPh3, 0.1 equiv.), and tert-butyl sodium ( NaOt-Bu, 3 eq.). The reaction mixture was heated to 100 °C and stirred at reflux for 24 hours. After completion of the reaction, the resulting organics were extracted, the organic layer was dried with anhydrous magnesium sulfate (MgSO4), purified by silica gel column chromatography (eluent: ethyl ether/water), and finally the target compound was obtained by recrystallization to 13.8 g (yield: 85%).

References

[1] Patent: KR101493482, 2015, B1. Location in patent: Paragraph 0126; 0202-0204
[2] Patent: KR2015/31892, 2015, A. Location in patent: Paragraph 0235-0237
[3] Patent: KR101614738, 2016, B1. Location in patent: Paragraph 0401-0403
[4] Patent: KR101857632, 2018, B1. Location in patent: Paragraph 0334; 0341-0343
[5] Patent: US2017/288147, 2017, A1. Location in patent: Paragraph 0132; 0133

Preparation Products And Raw materials

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