Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9847498-B2
Application number	US-201514671162-A
Country	US
Kind code	B2
Filing date	Mar 27, 2015
Priority date	Apr 14, 2014
Publication date	Dec 19, 2017
Grant date	Dec 19, 2017

Abstract

A novel type of blue emitter is described based on the azaphenanthridine imidazole ligand. The preferred use of this moiety for generating blue phosphorescence is as part of a symmetric platinum tetradentate complex.

First claim

We claim:

1. A compound of Formula II:

wherein X and Y are independently selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, alkyl, aryl, SiR′R″, and GeR′R″;
wherein at least one of X and Y is present;
wherein M is Pt or Pd;
wherein R 1 and R 3 each independently represent mono, or di-substitution, or no substitution;
wherein R 2 represent mono, di, tri, or tetra-substitution;
wherein R 1 , R 2 , R 3 , R′, and R″ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphino; and
wherein any adjacent R 1 , R 2 , R 3 , R′, and R″ are optionally joined to form a ring.

2. The compound of claim 1 , wherein M is Pt.

3. The compound of claim 1 , wherein the compound has the formula:

wherein R is selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphino.

4. The compound of claim 3 , wherein R is selected from the group consisting of alkyl, cycloalkyl, silyl, aryl, and heteroaryl.

5. The compound of claim 3 , wherein R is selected from the group consisting of methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, cyclopentyl, cyclohexyl, phenyl, 2,6-dimethylphenyl, 2,4,6-trimethylphenyl, and 2,6-diisopropylphenyl.

6. The compound of claim 1 , wherein only one of X and Y is present.

7. The compound of claim 3 , wherein the compound is selected from the group consisting of:

wherein R 6 represents mono, di, tri, or tetra-substitution, or no substitution;
wherein R 4 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphino; and
wherein any adjacent R 4 , R 5 , and R 6 are optionally joined to form a ring.

8. A compound selected from the group consisting of:

9. A device comprising an organic light emitting device, the organic light emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, the organic comprising a compound of Formula II:

wherein X and Y are independently selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, alkyl, aryl, SiR′R″, and GeR′R″;
wherein at least one of X and Y is present;
wherein M is Pt or Pd;
wherein R 1 and R 3 each independently represent mono, or di-substitution, or no substitution;
wherein R 2 represent mono, di, tri, or tetra-substitution;
wherein R 1 , R 2 , R 3 , R′, and R″ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, and phosphino; and
wherein any adjacent R 1 , R 2 , R 3 , R′, and R″ are optionally joined to form a ring.

10. The device of claim 9 selected from the group consisting of a consumer product, an electronic component module, an organic light-emitting device, and a lighting panel.

11. The device of claim 9 , wherein the organic layer further comprises a host; wherein the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;
wherein any substituent in the host is an unfused substituent independently selected from the group consisting of C n H 2n+1 , OC n H 2n+1 , OAr 1 , N(C n H 2n+1 ) 2 , N(Ar 1 )(Ar 2 ), CH═CH—C n H 2n+1 , C≡CC n H 2n+1 , Ar 1 , Ar 1 —Ar 2 , C n H 2n —Ar 1 , or no substitution;
wherein n is from 1 to 10; and
wherein Ar 1 and Ar 2 are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

12. The device of claim 9 , wherein the organic layer further comprises a host, wherein the host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

13. The device of claim 9 , wherein the organic layer further comprises a host and the host is selected from the group consisting of:

and combinations thereof.

14. A formulation comprising the compound of Formula II:

wherein X and Y are independently selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR′R″, alkyl, aryl, SiR′R″, and GeR′R″;
wherein at least one of X and Y is present;
wherein M is Pt or Pd;
wherein R 1 and R 3 each independently represent mono, or di-substitution;
wherein R 2 represent mono, di, tri, or tetra-substitution;
wherein R 1 , R 2 , R 3 , R′, and R″ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryl

Assignees

• Universal Display Corp

Inventors

• Brooks Jason
• Szigethy Geza
• Beers Scott

Classifications

• H01L51/0087

  Electricity · mapped topic

• H01L51/5206

  Electricity · mapped topic

• H01L51/0052

  Electricity · mapped topic

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title