Organic electroluminescent materials and devices

Patent metadata

Field	Value
Publication number	US-9312499-B1
Application number	US-201514589471-A
Country	US
Kind code	B1
Filing date	Jan 5, 2015
Priority date	Jan 5, 2015
Publication date	Apr 12, 2016
Grant date	Apr 12, 2016

Abstract

Compounds having a structure of Formula I,

where G 1 has the formula

having the structure

are described. In the structure of Formula I: Z 1 to Z 24 are each independently selected from group consisting of carbon and nitrogen; p is an integer from 1 to 10; adjacent carbazole groups G 11 , G 12 , and G 13 are each bonded together either by a 9N-2C bond or a 9N-3C bond; G 1 can include at least one 9N-2C intercarbazole bond and at least one 9N-3C intercarbazole bond; L and G 2 are each independently selected from the group consisting of alkyl, aryl, or heteroaryl, which may be further substituted; m and n are both integers; and m+n ranges from 1 to the maximum number of possible substituents on L. Formulations and devices, such as an OLEDs, that include the compound of Formula I are also described.

First claim

What is claimed is:

1. A compound having a structure of Formula I:

Formula I;
wherein G 1 has the formula

having the structure:

wherein Z 1 to Z 24 are each independently selected from group consisting of carbon and nitrogen;
wherein when any of Z 1 to Z 24 are nitrogen, there is no substitution on that nitrogen;
wherein R 1 , R 3 , R 5 and R 6 each independently represent mono, di, tri, or tetra substitution, or no substitution;
wherein R 2 and R 4 each independently represent mono, di, or tri substitution, or no substitution;
wherein p is an integer from 1 to 10;
wherein, when p is greater than 1, each G 12 can be same or different;
wherein adjacent carbazole groups G 11 and G 12 are each bonded together either by a 9N-2C bond or a 9N-3C bond;
wherein G 1 comprises at least one 9N-2C intercarbazole bond;
wherein G 13 is bonded to G 12 by a 9N-3C intercarbazole bond;
wherein R 1 to R 6 are each 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 acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein L and G 2 are each independently selected from the group consisting of alkyl, benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinolone, isoquinoline, quinazoline, cinnoline, pyrrole, indole, carbazole, furan, thiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, benzothienobenzofuran, benzothienobenzothiophene, benzofluorenofuran, benzothienocarbazole, benzofuranocarbazole, indenofluorene, indenocarbazole, indenodibenzothiophene, indenodibenzofuran, indolocarbazole, aza-dibenzofuran, aza-dibenzothiophene, diaza-dibenzothiophene, aza-carbazole, aza-fluorene, oxadiazole, oxazole, imidazole, benzimidazole, triazole and purine;
wherein L and G 2 are each independently optionally further substituted with one or more moieties selected from the group consisting of deuterium, alkyl, alkyloxyl, halogen, benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinolone, isoquinoline, quinazoline, cinnoline, pyrrole, indole, carbazole, furan, thiophene, dibenzofuran, dibenzothiophene, dibenzoselenophene, oxadiazole, oxazole, imidazole, benzimidazole, triazole and purine, and combinations thereof;
wherein m is an integer 1 or larger representing the number of G 1 substituents bonded to L, wherein, when m is greater than 1, each G 1 can be the same or different;
wherein n is an integer 0 or larger representing the number of G 2 substituents bonded to L, wherein, when n is greater than 1, each G 2 can be the same or different; and
wherein m+n ranges from 1 to the maximum number of possible substituents on L.

2. A compound of claim 1 , wherein R 1 to R 6 are each independently selected from the group consisting of hydrogen, deuterium, benzene, biphenyl, terphenyl, pyridine, dibenzofuran, dibenzothiophene, triphenylene, halogen, alkyl and combinations thereof.

3. A compound of claim 1 wherein G 1 is selected from a group consisting of

wherein Z 9′ to Z 16′ are each independently selected from group consisting of carbon and nitrogen;
wherein when any of Z 9′ to Z 16′ are nitrogen, there is no substitution on that nitrogen;
wherein R 3′ represents mono, di, tri, or tetra substitution, or no substitution;
wherein R 4′ represents mono, di, or tri substitution, or no substitution; and
wherein R 3′ and R 4′ are each 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 acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

4. A compound of claim 1 , wherein L and G 2 are independently selected from a group consisting of

wherein X and Y are each independently selected from a group consisting of O, S, CR 9 R 10 and NR 11 ;
wherein R 9 , R 10 and R 11 are each independently selected from a group consisting of hydrogen, deuterium, alkyl, benzene, pyridine, biphenyl and terphenyl, and combinations thereof; and
wherein R 9 and R 10 are optionally jointed to form a ring.

5. A compound of claim 1 , wherein the combination L-G 2 is selected from a group consisting of

6. A compound of claim 1 , wherein Z 1 to Z 24 are carbon.

7. A compound of claim 1 , wherein the compound comprises a structure selected from a group consisting of

8. A device comprising one or more organic light emitting devices, at least one of the one or more organic light emitting devices 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:

Formula I;
wherein G 1 has the formula

having the structure:

wherein Z 1 to Z 24 are each independently selected from group consisting of carbon and nitrogen;
wherein when any of Z 1 to Z 24 are nitrogen, there is no substitution on that nitrogen;
wherein R 1 , R 3 , R 5 and R 6 each independently represent mono, di, tri, or tetra substitution, or no substitution;
wherein R 2 and R 4 each independently represent mono, di, or tri substitution, or no substitution;
wherein p is an integer from 1 to 10;
wherein when p is greater than 1, each G 12 can be same or different;
wherein adjacent carbazole groups G 11 and G 12 are each bonded together either by a 9N-2C bond or a 9N-3C bond;
wherein G 1 comprises at least one 9N-2C intercarbazole bond;
wherein G 13 is bonded to G 12 by a 9N-3C intercarbazole bond;
wherein R 1 to R 6 are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alk

Assignees

• Universal Display Corp

Inventors

• Zeng Lichang

Classifications

• C09K2211/185

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

• C09K11/025 Primary

  non-luminescent particle coatings or suspension media · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• H01L51/0085

  Electricity · mapped topic

• H01L51/5096

  Electricity · mapped topic