Organic electroluminescent materials and devices
Provided are compounds useful in OLED application that have a structure of Formula I where: G D is a donor group and G A is an acceptor group; L 1 and L 2 are each independently an organic linker or a direct bond; G 1 is a non-conjugated moiety; m is an integer of at least 1; n is an integer of at least 1; and when m, n are more than 1, each G D , G A , L 1 , L 2 can be same or different.
1 . A compound having a structure of Formula I
wherein:
G D is a donor group and G A is an acceptor group, wherein at least one G A does not comprise pyridine;
L 1 and L 2 are each independently an organic linker or a direct bond;
G 1 is a non-conjugating moiety selected from the group consisting of
m is an integer of at least 1;
n is an integer of at least 1;
when m or n is more than 1, each G D , G A , L 1 , L 2 can be same or different;
wherein each G A independently comprises at least one of the chemical moieties selected from the group consisting of nitrile, isonitrile, borane, fluoride, pyridine, pyrimidine, pyrazine, triazine, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-triphenylene, imidazole, pyrazole, oxazole, thiazole, isoxazole, isothiazole, triazole, thiadiazole, and oxadiazole;
wherein, when G 1 is
then at least one phenyl of G 1 is directly bonded to at least two G A , wherein each of the at least two G A is independently nitrile or comprises at least one of the chemical moieties selected from the group consisting of isonitrile, borane, pyridine, pyrimidine, pyrazine, triazine, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-triphenylene, pyrazole, oxazole, thiazole, isoxazole, isothiazole, thiadiazole, and oxadiazole; and
at least one G D comprises at least one of the chemical moieties selected from the group consisting of indole, carbazole, benzothiophene, benzofuran, benzoselenophene, dibenzothiophene, dibenzofuran, dibenzoselenophene,
wherein each R can be same or different and is an organic linker L 1 bonded to G 1 , or a terminal group selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, aryl, heteroaryl, and combinations thereof.
2 . The compound of claim 1 , wherein G 1 is
3 . The compound of claim 1 , wherein m is 1 or 2, and n is 1 or 2.
4 . The compound of claim 1 , wherein at least one of m and n is at least 2, and at least two of the corresponding G D or G A are different.
5 . The compound of claim 1 , wherein each G D independently comprises at least one of the chemical moieties selected from the group consisting of indole, carbazole, benzothiophene, benzofuran, benzoselenophene, dibenzothiophene, dibenzofuran, and dibenzoselenophene.
6 . The compound of claim 1 , wherein each G A independently comprises at least one of the chemical moieties selected from the group consisting of nitrile, isonitrile, fluoride, and a six-membered aromatic ring having at least one nitrogens.
7 . The compound of claim 1 , wherein each G D independently comprises at least one of the chemical moieties selected from the group consisting of:
wherein X is selected from the group consisting of O, S, Se, and NR; and
wherein each R can be same or different and is an organic linker L 1 bonded to G 1 , or a terminal group selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, aryl, heteroaryl, and combinations thereof.
8 . The compound of claim 1 , wherein L 2 is phenyl.
9 . The compound of claim 1 , wherein each G D is independently selected from the group consisting of:
10 . The compound of claim 1 , wherein G 1 is
11 . The compound of claim 1 , wherein each G A is independently selected from the group consisting of
12 . The compound of claim 1 , wherein G 1 is
and at least one phenyl bonded to the Si is directly bonded to at least two G A that are CN.
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 a structure of Formula I
wherein:
G D is a donor group and G A is an acceptor group, wherein at least one G A does not comprise pyridine;
L 1 and L 2 are each independently an organic linker or a direct bond;
G 1 is a non-conjugating moiety selected from the group consisting of
m is an integer of at least 1;
n is an integer of at least 1;
when m or n is more than 1, each G D , G A , L 1 , L 2 can be same or different;
wherein each G A independently comprises at least one of the chemical moieties selected from the group consisting of nitrile, isonitrile, borane, fluoride, pyridine, pyrimidine, pyrazine, triazine, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-triphenylene, imidazole, pyrazole, oxazole, thiazole, isoxazole, isothiazole, triazole, thiadiazole, and oxadiazole;
wherein, when G 1 is
then at least one phenyl of G 1 is directly bonded to at least two G A , wherein each of the at least two G A is independently nitrile or comprises at least one of the chemical moieties selected from the group consisting of isonitrile, borane, pyridine, pyrimidine, pyrazine, triazine, aza-carbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, aza-triphenylene, pyrazole, oxazole, thiazole, isoxazole, isothiazole, thiadiazole, and oxadiazole; and
at least one G D comprises at least one of the chemical moieties selected from the group consisting of indole, carbazole, benzothiophene, benzofuran, benzoselenophene, dibenzothiophene, dibenzofuran, dibenzoselenophene,
wherein each R can be same or different and is an organic linker L 1 bonded to G 1 , or a terminal group selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, aryl, heteroaryl, and combinations thereof.
14 . The OLED of claim 13 , wherein the organic layer is an emissive layer and the compound is a host, and
wherein the organic layer further comprises a phosphorescent emissive dopant; wherein the 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 Y 1 to Y 13 are independently selected from the group consisting of carbon and nitrogen;
wherein Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , and GeR e R f ;
wherein R e and R f are optionally fused or joined to form a ring;
wherein each R a , R b , R c , and R d may independently represent from mono substitution to the maximum possible number of substitution, or no substitution;
wherein each R a , R b , R c , R d , R e , and R f is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof; and
wherein any two adjacent substituents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand.
15 . The OLED of claim 13 , wherein the organic layer is a blocking layer and the compound is a blocking material in the organic layer; or the organic layer is a transporting layer and the compound is a transporting material in the organic layer.
16 . The OLED of claim 13 , wherein the organic layer is an emissive layer and the compound is an emitter.
17 . The OLED of claim 13 , wherein the compound is a sensitizer and the OLED further comprises an acceptor; and wherein the acceptor is selected from the group consisting of fluorescent emitter, delayed fluorescence emitter, and combination thereof.
18 . A formulation comprising a compound according to claim 1 .
19 . A consumer product comprising a first device comprising 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 of claim 1 .