Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-10822361-B2
Application number	US-201815890750-A
Country	US
Kind code	B2
Filing date	Feb 7, 2018
Priority date	Feb 22, 2017
Publication date	Nov 3, 2020
Grant date	Nov 3, 2020

Abstract

A compound having the formula Ir(L A ) n (L B ) 3−n , having the structure,

Formula I, is disclosed. In Formula I, Z 1 , Z 2 , Z 3 , and Z 4 each independently are N or CR 2 ; X is O, S, or Se; n is an integer from 1 to 3; R 1 , R 2 , R 3 , R 4 , and R 5 each independently represent mono- to a maximum possible number of substitutions, or no substitution; R 1 , R 2 , R 3 , R 4 , and R 5 are each independently selected from a variety of substituents; any two substitutions in R 1 , R 2 , R 3 , R 4 , and R 5 are optionally joined to form a ring; at least one pair of substitutions in R 1 , R 2 , R 3 , R 4 , and R 5 are joined together to form a bridge structure comprising a backbone structure that forms a fused first ring, which can be further substituted; and the backbone structure is saturated. Organic light emitting devices and consumer products containing the compounds are also disclosed.

First claim

We claim:

1. A compound having the formula Ir(L A ) n (L B ) 3−n , having the structure:

wherein Z 1 , Z 2 , Z 3 , and Z 4 each independently are N or CR 2 ;
wherein X is O, S, or Se;
wherein n is an integer from 1 to 3;
wherein R 1 , R 2 , and R 3 each independently represent mono- to a maximum possible number of substitutions, or no substitution;
wherein R 4 and R 5 each independently represent mono- to a maximum possible number of substitutions;
wherein R 1 , R 2 , R 3 , R 4 , and R 5 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, phosphino, and combinations thereof;
wherein any substitutions in R 1 , R 2 , R 3 , R 4 , and R 5 are optionally joined to form a ring;
wherein one R 4 substituent is joined together with one R 5 substituent to form a bridge structure comprising a backbone structure that forms a fused first ring, which can be further substituted; and
wherein the backbone structure is saturated.

2. The compound of claim 1 , wherein n is 1.

3. The compound of claim 1 , wherein the first ring is a 5-membered ring.

4. The compound of claim 1 , wherein the first ring is a 6-membered ring.

5. The compound of claim 1 , wherein the first ring is carbocyclic.

6. The compound of claim 1 , wherein the first ring is a heterocyclic.

7. The compound of claim 1 , wherein the first ring contains a heteroatom selected from the group consisting of N, O, S, and Si.

8. The compound of claim 1 , wherein X is O.

9. The compound of claim 1 , wherein Z 1 , Z 2 , Z 3 , and Z 4 each independently are CR 2 .

10. The compound of claim 1 , wherein at least one of Z 1 , Z 2 , Z 3 , and Z 4 is N.

11. The compound of claim 1 , wherein the bridge structure is selected from the group consisting of:

wherein each R A is 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, phosphino, and combinations thereof;
wherein m is an integer selected from 0 to 10; and
wherein one * represents the atom which bonds to the parent ring containing the R 4 substituent and the other * represents the atom which bonds to the parent ring containing the R 5 substituent.

12. The compound of claim 1 , wherein the bridge structure is selected from the group consisting of:

wherein one * represents the atom which bonds to the parent ring containing the R 4 substituent and the other * represents the atom which bonds to the parent ring containing the R 5 substituent.

13. An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having the formula Ir(L A ) n (L B ) 3−n , having the structure:

wherein Z 1 , Z 2 , Z 3 , and Z 4 each independently are N or CR 2 ;
wherein X is O, S, or Se;
wherein n is an integer from 1 to 3;
wherein R 1 , R 2 , and R 3 each independently represent mono- to a maximum possible number of substitutions, or no substitution;
wherein R 4 and R 5 each independently represent mono- to a maximum possible number of substitutions;
wherein R 1 , R 2 , R 3 , R 4 , and R 5 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, phosphino, and combinations thereof;
wherein any substitutions in R 1 , R 2 , R 3 , R 4 , and R 5 are optionally joined to form a ring;
wherein one R 4 substituent is joined together with one R 5 substituent to form a bridge structure comprising a backbone structure that forms a fused first ring, which can be further substituted; and
wherein the backbone structure is saturated.

14. The OLED of claim 13 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.

15. The OLED of claim 13 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

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

and combinations thereof.

17. A consumer product comprising an organic light-emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having the formula Ir(L A ) n (L B ) 3−n , having the structure:

wherein Z 1 , Z 2 , Z 3 , and Z 4 each independently are N or CR 2 ;
wherein X is O, S, or Se;
wherein n is an integer from 1 to 3;
wherein R 1 , R 2 , and R 3 each independently represent mono- to a maximum possible number of substitutions, or no substitution;
wherein R 4 and R 5 each independently represent mono- to a maximum possible number of substitutions;
wherein R 1 , R 2 , R 3 , R 4 , and R 5 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, phosphino, and combinations thereof;
wherein any substitutions in R 1 , R 2 , R 3 , R 4 , and R 5 are optionally joined to form a ring;
wherein one R 4 substituent is joined together with one R 5 substituent to form a bridge structure comprising a backbone structure that forms a fused first ring, which can be further substituted; and
wherein the backbone structure is sat

Assignees

• Universal Display Corp

Inventors

• Zeng Lichang
• Ji Zhiqiang
• Margulies Eric A
• Lahti Paul M
• Weaver Michael S

Classifications

• C07B2200/05

  Isotopically modified compounds, e.g. labelled · CPC title

• H10K85/615

  Polycyclic condensed aromatic hydrocarbons, e.g. anthracene · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• C09K2211/185

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