Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9978956-B2
Application number	US-201615208517-A
Country	US
Kind code	B2
Filing date	Jul 12, 2016
Priority date	Jul 15, 2015
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

A compound having a structure of Formula I:

is provided. In the structure of Formula I, each one of X 1 to X 16 is independently CR X or N; each R X and R are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, carbazole, azacarbazole, dibenzofuran, dibenzothiophene, dibenzoselenophene, azadibenzofuran, azadibenzothiophene, azadibenzoselenophene, triphenylene, azatriphenylene, and combinations thereof; and any adjacent R X can join to form fused or unfused rings. Formulations and devices, such as an OLEDs, that include the compound containing a structure of Formula I are also described.

First claim

We claim:

1. A compound having a structure of Formula I:

wherein each one of X 1 to 16 is independently CR X or N;
wherein each R X and R are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, carbazole, azacarbazole, dibenzofuran, dibenzothiophene, dibenzoselenophene, azadibenzofuran, azadibenzothiophene, azadibenzoselenophene, triphenylene, azatriphenylene, and combinations thereof; and
wherein any adjacent R X can join to form fused or unfused rings.

2. The compound of claim 1 , having the structure of Formula I-a:

wherein each one of R 1 to R 16 independently represents a substituent selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, carbazole, azacarbazole, dibenzofuran, dibenzothiophene, dibenzoselenophene, azadibenzofuran, azadibenzothiophene, azadibenzoselenophene, triphenylene, azatriphenylene, and combinations thereof,
wherein any adjacent R 1 -R 16 can join to form a fused or unfused ring.

3. The compound of claim 2 , having the structure of Formula II:

wherein n is an integer ≥1;
wherein R t is

wherein all rings are optionally independently substituted by a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, carbazole, azacarbazole, dibenzofuran, dibenzothiophene, dibenzoselenophene, azadibenzofuran, azadibenzothiophene, azadibenzoselenophene, triphenylene, azatriphenylene, and combinations thereof; and
wherein any adjacent substituents can join to form fused or unfused rings.

4. The compound of claim 2 , wherein R is selected from the group consisting of aryl, heteroaryl, substituted aryl, and substituted heteroaryl.

5. The compound of claim 2 , wherein at least one of R 1 to R 16 is selected from the group consisting of aryl, heteroaryl, substituted aryl, and substituted heteroaryl.

6. The compound of claim 2 , wherein R is a triarylamine containing group.

7. The compound of claim 2 , wherein R is a group containing at least one electron withdrawing group of CN, F, C m F 2m+1 , Si m F 2m+1 , NCO, NCS, OCN, SCN, OC m F 2m+1 , or SC m F 2m+1 , wherein m≥1.

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

wherein R e is CN, F, C m F 2m+1 , Si m F 2m+1 , NCO, NCS, OCN, SCN, OC m F 2m+1 , or SC m F 2m+1 , and m≥1; and
wherein R t is

wherein all rings of R t are optionally independently substituted by a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, carbazole, azacarbazole, dibenzofuran, dibenzothiophene, dibenzoselenophene, azadibenzofuran, azadibenzothiophene, azadibenzoselenophene, triphenylene, azatriphenylene, and combinations thereof; and
wherein any adjacent substituents on R t can join to form fused or unfused rings.

9. The compound of claim 2 , wherein R is a group containing pyrimidine or triazene.

10. The compound of claim 1 , wherein at least one of X 1 to X 16 is N.

11. The compound of claim 1 , wherein at least two of adjacent R 1 -R 16 are fused into

wherein Z is CR′R″, NR′, O, S, or Se;
wherein R′ and R″ are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, carbazole, azacarbazole, dibenzofuran, dibenzothiophene, dibenzoselenophene, azadibenzofuran, azadibenzothiophene, azadibenzoselenophene, triphenylene, azatriphenylene, and combinations thereof; and
wherein all of the rings are optionally substituted.

12. A first organic light emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having a structure of Formula I:

wherein each one of X 1 to X 16 is independently CR X or N;
wherein R X and R are independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, carbazole, azacarbazole, dibenzofuran, dibenzothiophene, dibenzoselenophene, azadibenzofuran, azadibenzothiophene, azadibenzoselenophene, triphenylene, azatriphenylene, and combinations thereof; and
wherein any adjacent R X can join to form fused or unfused rings.

13. The first organic light emitting device of claim 12 , wherein the organic layer is an emissive layer and the compound of Formula I is a host.

14. The first organic light emitting device of claim 12 , wherein the organic layer further comprises a phosphorescent emissive dopant wherein the phosphorescent emissive dopant is a transition metal complex having at least one ligand or part of the ligand if the ligand is more than bidentate, selected from the group consisting of:

wherein each X 1 to X 13 are independently selected from the group consisting of carbon and nitrogen;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO 2 , CR

Assignees

• Universal Display Corp

Inventors

• Tsang Kit Yee
• Lee Chi Hang
• Kwong Raymond

Classifications

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C07D403/10

  linked by a carbon chain containing aromatic rings · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C09K2211/1022

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title