4-arylpyrimidine derivative
Provided is a novel substance that can emit phosphorescence. Alternatively, provided is a novel substance with high emission efficiency. An organometallic complex in which a 4-arylpyrimidine derivative is a ligand and iridium is a central metal is provided. Specifically, an organometallic complex having a structure represented by a general formula (G1) is provided. In the general formula (G1), R 1 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, R 2 represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted phenyl group, R 3 represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and Ar 1 represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.
1. An organometallic complex comprising a structure represented by formula (G1),
wherein R 1 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms,
wherein the substituted aryl group having 6to 10 carbon atoms is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms,
wherein R 2 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted phenyl group,
wherein the substituted phenyl group is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms,
wherein R 3 represents hydrogen or an alkyl group having 1 to 4 carbon atoms,
wherein Ar 1 represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms, and
wherein the substituted arylene group having 6 to 10 carbon atoms is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms.
2. The organometallic complex according to claim 1 ,
wherein the structure is represented by formula (G2),
wherein R 4 , R 5 , R 6 , and R 7 individually represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, halogen, a haloalkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and
wherein, with respect to R 4 , R 5 , R 6 , and R 7 , the substituted aryl group having 6 to 10 carbon atoms is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms.
3. The organometallic complex according to claim 1 ,
wherein the structure represented by formula (G3),
wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 individually represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, halogen, a haloalkyl group having 1 to 4carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and
wherein, with respect to R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 , the substituted aryl group having 6 to 10 carbon atoms is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms.
4. The organometallic complex according to claim 1 , wherein R 1 is represented by any one of a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, and a tert-butyl group.
5. An organometallic complex represented by formula (G4),
wherein L is any one of formulas (L1), (L2), (L3), (L4), (L5), (L6), and (L7),
wherein R 71 , R 72 , R 73 , R 74 , R 75 , R 76 , R 77 , R 78 , R 79 , R 80 , R 81 , R 82 , R 83 , R 84 , R 85 , R 86 , R 87 , R 88 , R 89 , R 90 , R 91 , R 92 , R 93 , R 94 , R 95 , R 96 , R 97 , R 98 , R 99 , R 100 , R 101 , R 102 , R 103 , R 104 , R 105 , R 106 , R 107 , R 108 , and R 109 individually represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, a halogen, a vinyl group, a haloalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and an alkylthio group having to 4 carbon atoms,
wherein A 1 , A 2 , and A 3 individually represent any of nitrogen, sp 2 hybridized carbon bonded to hydrogen, and sp 2 hybridized carbon bonded to a substituent R,
wherein the substituent R represents any of an alkyl group having 1 to 4 carbon atoms, a halogen, a haloalkyl group having 1 to 4 carbon atoms, and a phenyl group,
wherein R 1 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms,
wherein the substituted aryl group having 6 to 10 carbon atoms is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms,
wherein R 2 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted phenyl group,
wherein the substituted phenyl group is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms,
wherein R 3 represents hydrogen or an alkyl group having 1 to 4 carbon atoms,
wherein Ar 1 represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms, and
wherein the substituted arylene group having 6 to 10 carbon atoms is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms.
6. The organometallic complex according to claim 5 ,
wherein the organometallic complex is represented by formula (G5),
wherein R 4 , R 5 , R 6 , and R 7 individually represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, halogen, a haloalkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and
wherein, with respect to R 4 , R 5 , R 6 , and R 7 , the substituted aryl group having 6 to 10 carbon atoms is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms.
7. The organometallic complex according to claim 5 ,
wherein the organometallic complex is represented by formula (G6),
wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 individually represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, halogen, a haloalkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and
wherein, with respect to R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 , the substituted aryl group having 6 to 10 carbon atoms is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms.
8. The organometallic complex according to claim 5 ,
wherein the organometallic complex is represented by formula (100),
9. The organometallic complex according to claim 5 , wherein the organometallic complex is represented by any one of formulae (101), (119), (123), (134), (140), (190), (194), (195), and (199),
10. The organometallic complex according to claim 5 , wherein R 1 is represented by any one of a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, and a tert-butyl group.
11. An organometallic complex represented by formula (G7),
wherein R 1 represents an alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms,
wherein the substituted aryl group having 6 to 10 carbon atoms is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms,
wherein R 2 represents any of hydrogen, an alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted phenyl group,
wherein the substituted phenyl group is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms,
wherein R 3 represents hydrogen or an alkyl group having 1 to 4 carbon atoms,
wherein Ar 1 represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms, and
wherein the substituted arylene group having 6 to 10 carbon atoms is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms.
12. The organometallic complex according to claim 11 ,
wherein the organometallic complex is represented by formula (G8),
wherein R 4 , R 5 , R 6 , and R 7 individually represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, halogen, a haloalkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and
wherein, with respect to R 4 , R 5 , R 6 , and R 7 , the substituted aryl group having 6 to 10 carbon atoms is substituted by one or more alkyl groups each having 1 to 4 carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms.
13. The organometallic complex according to claim 11 ,
wherein the organometallic complex is represented by formula (G9),
wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 individually represent any of hydrogen, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, halogen, a haloalkyl group having 1 to 4carbon atoms, and a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and
wherein, with respect to wherein R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , and R 12 , the substituted aryl group having 6 to 10 carbon atoms is substituted by one or more alkyl groups each having 1 to 4carbon atoms, one or more alkoxy groups each having 1 to 4 carbon atoms, one or more alkylthio groups each having 1 to 4 carbon atoms, one or more aryl groups each having 6 to 10 carbon atoms, one or more halogen groups, or one or more haloalkyl groups each having 1 to 4 carbon atoms.
14. The organometallic complex according to claim 11 , wherein the organometallic complex is represented by any one of formulae (152), (178), and (200),
15. The organometallic complex according to claim 11 , wherein R 1 is represented by any one of a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, and a tert-butyl group.