952514-79-3

Basic information

• Product Name: Boronic acid, B-[4-(1-phenyl-1H-benzimidazol-2-yl)phenyl]-
• Synonyms: Boronic acid, B-[4-(1-phenyl-1H-benzimidazol-2-yl)phenyl]-;4-(1-Phenyl-1H-benzimidazol-2-yl)phenylboronic acid;B-[4-(1-Phenyl-1H-benzimidazol-2-yl)phenyl]boronic acid;B(OH)2 4-(1-Phenyl-1H-benziMidazol -2-yl)phenylboronic acid;[3-(1-phenyl-1H-benziMidazol-2-yl)phenyl]Boronic acid;4-(1-phenyl-1H-benzo[d]iMidazol-2-yl)phenylboronic acid (PBIB);BIBA;1-phenyl-2-( phenyl-4-boromic acid)-benzimidazole
• CAS NO: 952514-79-3
• Molecular Formula: C₁₉H₁₅BN₂O₂
• Molecular Weight: 314.15
• Product Categories: Electronic Chemicals;OLED materials,pharm chemical,electronic
• Mol File: 952514-79-3.mol

Chemical Properties

• Boiling Point: 572.6±60.0 °C(Predicted)
• Appearance: /
• Density: 1.21±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: soluble in Methanol
• PKA: 8.47±0.17(Predicted)
• CAS DataBase Reference: Boronic acid, B-[4-(1-phenyl-1H-benzimidazol-2-yl)phenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Boronic acid, B-[4-(1-phenyl-1H-benzimidazol-2-yl)phenyl]-(952514-79-3)
• EPA Substance Registry System: Boronic acid, B-[4-(1-phenyl-1H-benzimidazol-2-yl)phenyl]-(952514-79-3)

Safety Data

• Hazardous Substances Data: 952514-79-3(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

Synthetic route

triethyl borate (150-46-9) + 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole (2620-76-0) → (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3)

Conditions	Yield
Stage #1: 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole With n-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Inert atmosphere; Stage #2: triethyl borate In tetrahydrofuran; cyclohexane at 20℃; for 12h; Inert atmosphere;	80%

Triisopropyl borate (5419-55-6) + 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole (2620-76-0) → (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;	74%
Stage #1: 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃;	58.3%

Triisopropyl borate (5419-55-6) + water (7732-18-5) + 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole (2620-76-0) → (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3)

Conditions	Yield
Stage #1: Triisopropyl borate; 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; Stage #2: water With hydrogenchloride In tetrahydrofuran; hexane	74%

hydrogenchloride (7647-01-0) + Trimethyl borate (121-43-7) + 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole (2620-76-0) → (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3)

Conditions	Yield
Stage #1: 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole In tetrahydrofuran at -78℃; for 0.5h; Stage #2: With n-butyllithium at -78℃; for 0.5h; Stage #3: hydrogenchloride; Trimethyl borate Further stages;	70%

Trimethyl borate (121-43-7) + water (7732-18-5) + 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole (2620-76-0) → (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3)

Conditions	Yield
Stage #1: 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: Trimethyl borate In tetrahydrofuran for 2h; Stage #3: water In tetrahydrofuran for 0.333333h;	65%
Stage #1: 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: Trimethyl borate In tetrahydrofuran for 2h; Stage #3: water With hydrogenchloride In tetrahydrofuran for 0.833333h;	60%

2-(4-bromophenyl)-1-phenyl-1H-benzimidazole (2620-76-0) → (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3)

Conditions	Yield
Stage #1: 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole With n-butyllithium; Trimethyl borate Stage #2: With hydrogenchloride In water

4-Bromobenzoic acid (586-76-5) → (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: thionyl chloride / 1,2-dichloro-ethane / 3 h / Reflux 2.1: 1-methyl-pyrrolidin-2-one / 20 °C 3.1: acetic acid / 12 h / Reflux 4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 4.2: -78 - 20 °C View Scheme

4-chlorobenzoyl chloride (586-75-4) → (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 1-methyl-pyrrolidin-2-one / 20 °C 2.1: acetic acid / 12 h / Reflux 3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 3.2: -78 - 20 °C View Scheme
Multi-step reaction with 3 steps 1: triethylamine / 1-methyl-pyrrolidin-2-one / 20 °C 2: acetic acid / 12 h / Reflux 3: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: triethylamine / 1-methyl-pyrrolidin-2-one / 20 °C 2: acetic acid / 12 h / Reflux 3: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: N,N-dimethyl acetamide 2.1: acetic acid / 0.5 h / 115 °C 3.1: TEFLON / tetrahydrofuran / 0.5 h / -78 °C 3.2: 0.5 h / -78 °C View Scheme

4-bromo-N-(2-(phenylamino)phenyl)benzamide (359427-13-7) → (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: acetic acid / 12 h / Reflux 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 2.2: -78 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: acetic acid / 12 h / Reflux 2: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: acetic acid / 12 h / Reflux 2: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: acetic acid / 0.5 h / 115 °C 2.1: TEFLON / tetrahydrofuran / 0.5 h / -78 °C 2.2: 0.5 h / -78 °C View Scheme

4-formylphenylboronic acid, (87199-17-5) → (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 130 °C / Molecular sieve; Inert atmosphere 2: potassium iodide / N,N-dimethyl-formamide / 80 °C 3: sodium hydroxide / N,N-dimethyl-formamide; water / 0.5 h / 20 °C View Scheme

(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)boronic acid MIDA ester → (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3)

Conditions	Yield
With sodium hydroxide In water; N,N-dimethyl-formamide at 20℃; for 0.5h;

4-formylphenylboronic acid (1072960-66-7) → (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium iodide / N,N-dimethyl-formamide / 80 °C 2: sodium hydroxide / N,N-dimethyl-formamide; water / 0.5 h / 20 °C View Scheme

N-phenyl-1,2-benzenediamine (534-85-0) → (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / 1-methyl-pyrrolidin-2-one / 20 °C 2: acetic acid / 12 h / Reflux 3: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: triethylamine / 1-methyl-pyrrolidin-2-one / 20 °C 2: acetic acid / 12 h / Reflux 3: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: N,N-dimethyl acetamide 2.1: acetic acid / 0.5 h / 115 °C 3.1: TEFLON / tetrahydrofuran / 0.5 h / -78 °C 3.2: 0.5 h / -78 °C View Scheme

4-chlorobenzoyl chloride (586-75-4) + N-phenyl-1,2-benzenediamine (534-85-0) → (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / tetrahydrofuran 2: n-butyllithium View Scheme

Trimethyl borate (121-43-7) + 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole (2620-76-0) → (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3)

Conditions	Yield
Stage #1: 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole With n-butyllithium Stage #2: Trimethyl borate Stage #3: With hydrogenchloride In water

2-bromo-1-phenyl-1H-benzo[d]imidazole → (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / 10 h / 85 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C / Inert atmosphere 2.2: 12 h / 20 °C / Inert atmosphere View Scheme

2-bromo-1H-1,3-benzodiazole (54624-57-6) → (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3)

Conditions

Yield

Multi-step reaction with 3 steps 1.1: copper(l) iodide; 18-crown-6 ether; potassium carbonate / N,N-dimethyl acetamide / 12 h / 165 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / 10 h / 85 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C / Inert atmosphere 3.2: 12 h / 20 °C / Inert atmosphere View Scheme

iodobenzene (591-50-4) → (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3)

Conditions

Yield

Multi-step reaction with 3 steps 1.1: copper(l) iodide; 18-crown-6 ether; potassium carbonate / N,N-dimethyl acetamide / 12 h / 165 °C / Inert atmosphere 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; ethanol; water / 10 h / 85 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C / Inert atmosphere 3.2: 12 h / 20 °C / Inert atmosphere View Scheme

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + 2',7'-dibromospiro[fluorene-9,9'-thioxanthene] → C63H40N4S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 5h; Suzuki Coupling; Inert atmosphere; Reflux;	95%

9-(2-chloroquinazolin-4-yl)-9H-carbazole (1262866-84-1) + (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) → 9-(2-(4-(1-phenyl-1H-indol-2-yl)phenyl)quinazolin-4-yl)-9H-carbazole

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In water; toluene at 100℃; for 4h; Inert atmosphere;	94%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + 2-amino-6-bromophenol (28165-50-6) → C25H19N3O

Conditions	Yield
With palladium diacetate; sodium carbonate In N,N-dimethyl-formamide at 80℃; for 2h;	92%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + 7-(4-bromophenyl)-7H-benzofuro[2,3-b]carbazole → FCBI

Conditions	Yield
With palladium diacetate; potassium carbonate; XPhos In ethanol; water; toluene Suzuki Coupling;	91.7%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + 3-bromo-2-(dibenzo[b,d]thiophen-4-yl)pyridine → C35H22N2S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 5h; Reflux;	91%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + C29H21BrN2 → C48H34N4

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 12h; Reflux; Inert atmosphere;	89%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + C38H22BrN → C57H35N3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water for 5h; Reflux; Inert atmosphere;	89%

3,5-bis(4-tert-butylphenyl)-1-bromobenzene (351029-50-0) + (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) → C45H42N2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12h; Inert atmosphere;	89%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + para-bromoacetophenone (99-90-1) → C27H20N2O

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 80℃; for 16h; Inert atmosphere;	88.5%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 20 - 80℃; for 16h; Inert atmosphere;	88.5%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + 2-bromo-5-chloro-1,3,4-thiadiazole → C40H26N6S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 85℃; for 14h; Inert atmosphere;	88%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + 3-bromo-2-(dibenzo[b,d]furan-4-yl)pyridine → C36H23N3O

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 5h; Reflux;	87%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + C32H20BrNO → C51H33N3O

Conditions	Yield
With palladium diacetate; potassium carbonate; XPhos In tetrahydrofuran; water for 4h; Inert atmosphere; Reflux;	87%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + 10-(4-Bromophenyl)-12,12-dimethyl-10,12dihydro-10-azaindeno[2,1-b]-fluorene (1361126-22-8) → ICBI

Conditions	Yield
With palladium diacetate; potassium carbonate; XPhos In ethanol; water; toluene Suzuki Coupling;	85.7%

(rac)-2,2'-diiodo-9,9'-spirobifluorene (790674-48-5) + (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) → C63H40N4 (1274565-72-8)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); tri-tert-butyl phosphine; sodium carbonate In toluene for 48h; Inert atmosphere; Reflux;	85%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + C31H20BrN (1290058-18-2) → 8,8-Diphenyl-6-[4-(1-phenyl-1H-benzoimidazol-2-yl)-phenyl]-8H-indolo[3,2,1-de]acridine (1290058-19-3)

Conditions	Yield
With potassium phosphate monohydrate; tris-(o-tolyl)phosphine; palladium diacetate In 1,4-dioxane; water; toluene for 5h; Reflux;	85%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + C34H21BrN2 → C53H34N4

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 5h; Inert atmosphere; Heating;	85%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + 6-bromobenzo[d]triphenyleno[2,3-b]thiophene → C43H26N2S

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water at 90℃; for 24h; Inert atmosphere;	85%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + C19H18F3NO5S → C37H31N3O2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 70℃; for 8h; Inert atmosphere;	84.9%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + 2,7-dibromo-9,9'-spirobi[fluorene] (171408-84-7) → C63H40N4 (1274565-70-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); tri-tert-butyl phosphine; sodium carbonate In toluene for 48h; Inert atmosphere; Reflux;	84%

9-Bromoanthracene (1564-64-3) + (4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) → 9-[4-(1-phenyl-1H-benzimidazol-2-yl)phenyl]anthracene (944801-79-0)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 6h; Inert atmosphere; Reflux;	83%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + C23H14ClN → C42H27N3

Conditions	Yield
With potassium phosphate; bis(tri-t-butylphosphine)palladium(0) In 1,4-dioxane; water for 5h; Reflux;	83%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + 2-phenyl-6-chloroimidazo<1,2-b>pyridazine (1844-53-7) → C31H21N5

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 10h; Reflux; Inert atmosphere;	83%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + C20H8Br2O4S2 → C58H34N4O4S2

Conditions	Yield
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); sodium carbonate In toluene at 75 - 90℃; Inert atmosphere;	83%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + C25H17BrN2 → C44H30N4

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 10h; Suzuki Coupling;	82.9%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + 12-bromo-pyrido[3',2':4,5]pyrrolo[1,2-f]phenanthridine → C38H24N4

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 24h; Reflux;	82%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + 3-(10-bromophenanthren-9-yl)-9-phenyl-9H-carbazole → 9-phenyl-3-(10-(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)phenanthren-9-yl)-9H-carbazole

Conditions	Yield
With palladium diacetate; potassium carbonate In tetrahydrofuran; water for 6h; Suzuki Coupling; Reflux; Inert atmosphere;	82%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + 3-bromo-9-(naphthalen-2-yl)-9H-carbazole (934545-80-9) → 9-(naphthyl-2-yl)-3-(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)-9H carbazole (1334036-93-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 48h; Suzuki coupling; Inert atmosphere; Reflux;	81.2%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + 5,10-dibromo-1,2-diphenyl-1H-phenanthro[9,10-d]imidazole → C65H42N6

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 5h; Inert atmosphere; Reflux;	81%

(4-(1-phenyl-1H-benzo [d]imidazole-2-yl) phenyl)boronic acid (952514-79-3) + C48H43Br → 2-(4-(2,6-di-tert-butyl-10-(4-(1,2,2-triphenylvinyl)phenyl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol; water; toluene at 110℃; for 12h; Suzuki Coupling; Inert atmosphere;	81%

Upstream product

• 2620-76-0 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole 
• 586-76-5 4-Bromobenzoic acid 
• 586-75-4 4-chlorobenzoyl chloride 
• 359427-13-7 4-bromo-N-(2-(phenylamino)phenyl)benzamide 
• 5419-55-6 Triisopropyl borate 
• 87199-17-5 4-formylphenylboronic acid, 
• 1072960-66-7 4-formylphenylboronic acid 
• 534-85-0 N-phenyl-1,2-benzenediamine 
• 121-43-7 Trimethyl borate 
• 7732-18-5 water 
• 7647-01-0 hydrogenchloride 
• 150-46-9 triethyl borate 
• 54624-57-6 2-bromo-1H-1,3-benzodiazole 
• 591-50-4 iodobenzene 

Downstream Products

• 1274565-72-8 C₆₃H₄₀N₄ 
• 1274565-70-6 C₆₃H₄₀N₄ 
• 1283598-73-1 9-[4-(1-phenyl-1H-benzimidazol-2-yl)-biphenyl-4'-yl]anthracene 
• 1226993-71-0 3,5-bis(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)vinylbenzene 
• 1226993-70-9 3,5-bis(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)benzaldehyde 
• 1294411-24-7 9-phenyl-3-(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)-9H-carbazole 
• 1334036-93-9 9-(naphthyl-2-yl)-3-(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)-9H carbazole 
• 1258780-50-5 9-phenyl-3,6-bis(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)-9H-carbazole 
• 1425793-65-2 9-[4-(1-phenyl-1H-benzo [d]imidazol-2-yl) phenyl]-11H-benzocarbazole 
• 1425793-66-3 11-(4,6-diphenyl-1,3,5-triazin-2-yl)-9-[4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl]-11H-benzo[a]carbazole 
• 1425793-69-6 12-[4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl]-7H-dibenzo[a,g]carbazole 
• 1425793-70-9 7-(4,6-diphenyl-1,3,5-triazin-2-yl)-12-[4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl]-7H-dibenzo[a,g]carbazole 
• 1425793-64-1 11-acetyl-9-[4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl]-11H-benzocarbazole 
• 1425793-68-5 7-acetyl-12-[4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl]-7H-dibenzo[a,g]carbazole 

Relevant articles and documents

Compound and organic electroluminescent device

The invention provides a novel compound, and particularly relates to a compound containing an anthracene structure connected with a heterocyclic structure and application of the compound in an organiclight-emitting device. The novel organic electroluminescent material, namely the compound of the invention is represented by a formula (I) which is described in the specification. The novel compoundprovided by the invention has optimized electron injection and transmission capability, good exciton blocking performance, and remarkable and excellent electron mobility, and shows good film-forming performance when being applied to an organic layer of the organic light-emitting device, so the efficiency and stability of an electron transmission layer can be improved. The device adopting the compound has the advantages of high luminous efficiency, low driving voltage and long service life.

Bipolar compounds based on 1,3,4-thiadiazole, and preparation method and application thereof

The invention provides novel bipolar compounds which are formed by using 1,3,4-thiadiazole with strong electron withdrawing ability as a core group and connecting the position 2 and the position 5 of1,3,4-thiadiazole to groups having electron donor/acceptor abilities respectively with arylene groups as Pi bridges. The parent nucleus structure, i.e., 1,3,4-thiadiazole, has symmetrical strong electron withdrawing ability, so the compounds extending via the Pi bridges present ordered closely-packed structures; bipolar benzoheterocycles endow the compounds with certain rigidity, so low optical loss caused by light near a negative pole can be realized, and optical extraction efficiency is improved; so the compounds are an ideal light-emitting layer material. Meanwhile, since the compounds haveparent nucleuses with strong electron withdrawing ability and the donor/acceptor groups, the compounds are allowed to have powerful charge balancing ability; conjugation broken by the Pi bridges effectively improves the problem of band gap reduction caused by intramolecular charge transfer of electron-donating and electron-withdrawing groups and endows a device with lower driving voltage, higherdevice efficiency and lower efficiency drop; so the compounds are also an excellent host material for luminescent layers.

A phenanthro imidazole symmetrical derivatives of the main material and electroluminescent device

The invention relates to a phenanthroimidazole symmetric derivative host material. The structure of the host material is represented by formula I, and can be used to form an organic electroluminescent device with the advantages of high luminescence efficiency, low driving voltage, long life, high brightness and high color purity. In the formula I, R1 and R2 are respectively independently selected from the hydrogen atom, substituted or unsubstituted C1-C30 alkyl groups, C1-C30 cycloalkyl groups, C1-C30 saturated alkyl groups, substituted or unsubstituted C1-C30 alkyloxy groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C6-C30 aryloxy groups, substituted or unsubstituted C6-C30 arylamino groups, substituted or unsubstituted C2-C30 heterocyclic groups, substituted or unsubstituted C6-C30 fused polycyclic groups, hydroxy groups, cyan groups or substituted or unsubstituted amino groups.

QUINAZOLINE DERIVED COMPOUNDS FOR ELECTRONIC FILMS AND DEVICES

The invention provides a composition comprising at least one compound selected from the group consisting of the following (A, B, C and D): A) wherein R1, R2 and R3 are each described herein; and wherein Formula 1 comprises at least three C-N double bonds; and wherein one or more hydrogens may be optionally substituted with deuterium; B) wherein R1’, R2’, R3’, R4’, R5’ and L are each described herein, and and wherein if R1’ comprises a biphenyl, it does not comprises a carbazole; and wherein one or more hydrogens may be optionally substituted with deuterium; C) wherein R1”, R2”, R3”, R4” and R5” are each described; and wherein if R1’ comprises a biphenyl, it does not comprises a carbazole; and wherein one or more hydrogens may be optionally substituted with deuterium; and D) a combination thereof.

Isoquinoline compound and its preparation method, the organic electroluminescent device

The invention provides isoquinoline compounds and a preparation method thereof, and an organic light emitting diode. The isoquinoline compounds are as shown in a molecular formula (I) in the specification. Compared with the prior art, the isoquinoline compounds provided by the invention are prepared by introducing Q1, Q2, Ar1, Ar2, Ar3 and Ar4 groups into benzo[g]isoquinoline compounds, so electronic density and skills can be improved; meanwhile, R1 can improve performances of the isoquinoline compounds, so the organic light emitting diode containing the isoquinoline compounds as shown in the molecular formula (I) has the characteristics of high brightness, good heat resistance, long service life, high efficiency, etc.

Synthesis and photophysical properties of new through-space conjugated luminogens constructed by folded tetraphenylethene

Through-space conjugation refers to a unique non-covalent electronic coupling interaction typically occurring between two face-to-face parallel aromatic units, which has shown great potential in constructing novel functional materials capable of multidimensional carrier and energy transportation. However, well-studied through-space conjugation systems are quite rare. In this work, a series of tailored through-space conjugated luminogens are readily constructed from the folded tetraphenylethene (TPE) core and common functional groups like fluorene, carbazole, imidazole and dimesitylborane. Systematic studies on their photophysical properties were conducted, and a deep insight into the structure-property relationship is gained. The new molecules show aggregation-enhanced emission (AEE) characteristics with high fluorescence quantum efficiencies of up to 54% in films. Through the binding experiments of fluoride ions with boron atoms, the impacts of through-space conjugation on the photophysical properties of the luminogens are carefully studied. All these results undoubtedly provide important clues to the rational design of efficient through-space conjugated materials with specific functions.

An organic electron transport compound

The invention provides an organic electronic transmission compound having a following structural formula (I) as shown in the specification. The organic electronic transmission compound is better in thermal stability, is high in luminous efficiency and purity, can be used for manufacturing an organic electroluminescence device and is applied to the field of organic solar batteries, organic thin film transistors or organic photoreceptors..

A benzimidazole-based electron transport compound

The invention provides a benzimidazole-based electron transport compound with a structure formula I. The compound has the advantages of relatively good thermal stability, high luminous efficiency and high luminous purity. The compound can be used for manufacturing an organic electroluminescent device and can be applied in the fields of organic solar cells, organic thin-film transistors or organic photoreceptors. The structure formula I is as shown in the specification.

Synthesis of Benzimidazoles bearing borionic acid functionality via metal-free aerobic oxidation

The present invention relates to benzimidazole derivative useful as a natural product, and as an intermediate product for synthesizing a medicine by having a boronic functional group in a molecule, and to a method to synthesize the benzimidazole derivative in an environment friendly way. More particularly, the present invention relates to a method to manufacture benzimidazole derivative having a boronic functional group in a molecule by using an aerobic oxidation cyclization reaction using air as an oxidizing agent under the presence of an alkaline metal halide or alkali earth metal halide catalyst in an anhydrous condition.COPYRIGHT KIPO 2016

A kind of organic compound and its use this organic compound electroluminescent device

The invention relates to an organic compound. The organic compound has a structure represented in a formula I, wherein R1, R2 and R3 are independently selected from hydrogen atom, substituted or non-substituted C1-C30 alkyl, substituted or non-substituted C1-C30 naphthenic base, substituted or non-substituted C1-C30 alkoxy, substituted or non-substituted C6-C30 aryl, substituted or non-substituted C6-C30 aryloxy, substituted or non-substituted C6-C30 arylamine, substituted or non-substituted C2-C30 heterocyclic ring, substituted or non-substituted C6-C30 condensed polycyclic group, hydroxyl, cyano group and substituted or non-substituted amino, respectively. Furthermore, the invention relates to an electroluminescent device, wherein the electroluminescent device comprises a hole injection layer and/or a hole transport layer using at least one of the compounds.